Tricyclic compounds with antiviral activity

Info

Publication number: 20050075332
Type: Application
Filed: Jul 28, 2004
Publication Date: Apr 7, 2005
Applicant:
Inventors: Richard Booth (Ann Arbor, MI), Vara Nagendra Josyula (Ann Arbor, MI), Annette Meyer (Brighton, MI), Bruce Steinbaugh (Chelsea, MI)
Application Number: 10/901,953

Abstract

The present invention provides a compound of the formula (I) and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family. In said formula, X═O, (CH2)m, S, SO, SO2, NH, NR8, or a chemical bond; Y═O, (CH2)m, S, SO, SO2, NH, NR8; Z=NH, O, NR8, S, SO, SO2. The remaining substituents are described in the specification.

Description

Description

FIELD OF THE INVENTION

The present invention relates to compounds possessing antiviral activity against viruses of the herpes family, or a composition containing them. These compounds provide a method for treating herpes viral infections, including condition caused by herpes simplex I such as cold sores, herpes simplex II such as genital herpes, as well as shingles caused by herpes zoster and infections caused by cytomegalovirus, Epstein Barr Virus.

BACKGROUND OF THE INVENTION

Various subfamilies of herpes viruses (Herpes viridae) exist: α-herpesvirinae, β-herpesvirinae, γ-herpesvirinae and cercopithecing Herpes virus I (B virus); some specific viruses are: Herpes simplex virus-1(HSV-1), Herpes simplex virus-2 (HSV-2), Cytomegalovirus (CMV), Varicella Zoster virus (VZV), Epstein-Barr virus (EBV), human herpes virus-6(HHV-6), human herpes virus-7(HHV-7), human herpes virus-8(HHV) as well as others which may not yet be defined.

The incidence of infections by Herpes simplex virus is very high throughout the world. Serological studies showed that herpes viral infections affect a substantial percentage of the population. Reactivation of herpes virus infections may lead to recurrent infections. The risk of severe diseases increases with decreasing immunocompetence of the host. There is a pressing need for improved therapy for treating this disease. Currently, exclusive of vaccines, treatment involves primarily nucleoside drugs such as acyclovir, which target thymidine kinase and suffer from development of resistance.

SUMMARY OF THE INVENTION

The present invention provides a compound of the formula and its pharmaceutically acceptable salts, or the compound and its pharmaceutical composition having useful antiviral activity against viruses of the herpes family.
wherein:

- X═O, (CH₂)_m, S, SO, SO₂, NH, NR₈or a chemical bond;
- Y═O, (CH₂)_m, S, SO, SO₂, NH, NR₈;
- Z=N, NH, O, NHR₈, NR₈, S, SO, SO₂;
- n=an integer of from 0 to 2;
- m=an integer of 1,2, or 3;
- R₁, R₂, R₃, R₄, R₅independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF₃, OCF₃, aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O or S;
- Ar=phenyl,
  - substituted phenyl,
  - benzoheterocyclic ring,
  - substituted benzoheterocyclic ring,
  - heterocyclic ring, or
  - substituted heterocyclic ring, which have substitutions R₆or R₇;
- R₆and R₇are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF₃, aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S;
- R₆and R₇may also form a ring, optionally cycloalkyl or aryl or substituted aryl;
- R₈is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.

The invention also provides for a pharmaceutical composition for the treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises an amount of the compound of claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.

The invention also provides for a method of treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises administering to a subject in need of such treatment an effective antivirally dosage of a composition of formula I.

DESCRIPTION OF PREFERRED EMBODIMENTS

The present invention pertains to anti viral compounds. Preferred compounds are as follows:

One preferred compound is:

Another preferred compound is:

The term “alkyl” means a straight or branched hydrocarbon radical having from 1 to 12 carbon atoms unless otherwise specified and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl. The alkyl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected from F, Cl, Br, I, OH, NH₂, SH, CN, NO₂, OCH₃, OCH₂CH₂OH, NHCH₃, or N(CH₃)₂.

The term “cycloalkyl” means a hydrocarbon ring, which contains from 3 to 12 carbon atoms unless otherwise specified, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Where possible, the cycloalkyl group may contain double bonds. The cycloalkyl ring may be unsubstituted or substituted by from 1 to 3 substituents selected from alkyl, cycloalkyl, alkoxy, thioalkoxy all as defined herein, hydroxy, thiol, nitro, halogen, amino, formyl, carboxyl, nitrile, —NH—CO—R, —CO—NHR—, —CO₂R, —COR, aryl, or heteroaryl wherein alkyl (R), aryl, and heteroaryl are defined as herein.

The term “alkoxy” having 1-6 carbon atoms means a C₁-C₆alkyl-O-group or radical wherein C₁-C₆alkyl has the meaning as defined above. Illustrative examples of a straight or branched alkoxy group or radical having from 1 to 6 carbon atoms, also known as a C₁- C₆alloxy, include methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy, 2-methyl-1-propoxy, and 1,1-dimethylethoxy, 1-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, and 4-methyl-1-pentoxy.

The term “thioalkoxy” having 1-6 carbon atoms means a C₁-C₆alkyl-S-group or radical wherein C₁-C₆alkyl has the meaning as defined above. Illustrative examples of a straight or branched thioalkoxy group or radical having from 1 to 6 carbon atoms, also known as a C₁- C₆thioalkoxy, include methylthio, ethylthio, 1-propylthio, 2-propylthio, 1-butylthio and 2-butylthio, l-pentylthio, 2-pentylthio, 3-pentylthio, 2,2-dimethylpropylthio, 1-hexylthio, 2-hexylthio, 3-hexylthio, and 4-methyl-1-pentylthio.

The term “aryl” means an aromatic carbocyclic ring having from 6 to 10 carbon atoms. Illustrative examples of an aryl group or radical include phenyl, 1-naphthyl, and 2-napthyl. The aryl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH₂, SH, CN, NO₂, OCH₃, OCH₂CH₂OH, NHCH₃, or N(CH₃)₂.

The term “Oaryl” means an aryl-O-group or radical wherein aryl has the meaning as defined above. Illustrative examples of an Oaryl group or radical include phenoxy, 1-naphthyloxy, and 2-napthyloxy. Oaryl groups may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH₂, SH, CN, NO₂, OCH₃, OCH₂CH₂OH, NHCH₃, or N(CH₃)₂.

The term “halogen” means bromine, chlorine, fluorine or iodine.

The term “monoalkylamino” means an NH-alkyl group or radical wherein alkyl has the meaning as defined above.

The term “dialkylamino” means an N-(alkyl)₂group or radical wherein alkyl has the meaning as defined above.

The term “aminoalkyl” having 1-6 carbon atoms means an H₂N—(C₁-C₆alkyl)-group or radical wherein C₁-C₆alkyl has the meaning as defined above. The aminoalkyl group is a substituted C₁-C₆alkyl group or radical containing at least one substituent which is NH₂.

The term “aminoaryl” means an H₂N-aryl-group or radical wherein aryl has the meaning as defined above. The aminoaryl group is a substituted aryl group or radical containing at least one substituent which is NH₂.

The term “carbocycle” means cycloalkyl as defined above.

The term “heteroatom” means a nitrogen, sulfur, or oxygen.

The term “heterocycle” means a heterocyclic radical which are 5-7 atoms having 14 heteroatoms and are selected from: furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, piperazine, piperidine, morpholine, thiomorpholine, oxolane, dioxane, sulfolane, unsubstituted or substituted by 1 to 2 substituents selected from alkyl as defined above. For heterocycles containing sulfur, the oxidized sulfur heterocycles containing SO or SO₂groups are also included.

The term “benzoheterocyclic ring” (“fused heterocycle”) refers to a heterocycle that is adjoined at two consecutive positions with a phenyl ring or another heterocycle such rings may include 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolinyl, 2-, 3-, 4-, 5-, 6-, or 7-indolyl, 2-, 3-, 4-, 5-, 6-, or 7-benzo[b]thienyl, 2-, 4-, 5-, 6-, or 7-benzoxazolyl, 2-, 4-, 5-, 6-, or 7-benzimidazolyl, 2-, 4-, 5-, 6-, or 7-benzothiazolyl.

Some of the compounds of Formula I are capable of further forming pharmaceutically acceptable acid-addition and/or base salts. All of these forms are within the scope of the present invention.

Pharmaceutically acceptable acid addition salts of the compounds of Formula I include salts derived from nontoxic inorganic acids such as hydrochloric, nitric, phosphoric, sulfuric, hydrobromic, hydriodic, hydrofluoric, phosphorous, and the like, as well as the salts derived from nontoxic organic acids, such as aliphatic mono- and dicarboxylic acids, phenyl-substituted alkanoic acids, hydroxy alkanoic acids, alkanedioic acids, aromatic acids, aliphatic and aromatic sulfonic acids, etc. Such salts thus include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihyrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, trifluoroacetate, propionate, caprylate, isobutyrate, oxalate, malonate, succinates suberate, sebacate, fumarate, maleate, mandelate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, phthalate, benzenesulfonate, toluenesulfonate, phenylacetate, citrate, lactate, maleate, tartrate, methanesulfonate, and the like. Also contemplated are salts of amino acids such as arginate and the like and gluconate, galacturonate (see, for example, Berge S. M., et al., “Pharmaceutical Salts,” Journal of Pharmaceutical Science, 1977;66:1-19.

The acid addition salt of said basic compounds are prepared by contacting the free base form with a sufficient amount of the desired acid to produce the salt in the conventional manner.

Pharmaceutically acceptable base addition salts are formed with metals or amines, such as alkali and alkaline earth metals or organic amines. Examples of metals used as cations are sodium, potassium, magnesium, calcium, and the like. Examples of suitable amines are N,N′-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, dicyclohexylamine, ethylenediamine, N-methylglucamine, and procaine (see, for example, Berge, supra., 1977).

The base addition salts of said acidic compounds are prepared by contacting the free acid form with a sufficient amount of the desired base to produce the salt in the conventional manner.

Certain of the compounds of the present invention can exist in unsolvated forms as well as solvated forms, including hydrated forms. In general, the solvated forms, including hydrated forms, are equivalent to unsolvated forms and are intended to be encompassed within the scope of the present invention.

Certain of the compounds of the present invention possess one or more chiral centers and each center may exist in the R(D) or S(L) configuration. The present invention includes all enantiomeric and epimeric forms as well as the appropriate mixtures thereof. Configuration drawn is most preferred.

The compounds of the present invention can be prepared and administered in a wide variety of oral and parenteral dosage forms. Thus, the compounds of the present invention can be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally. Also, the compounds of the present invention can be administered by inhalation, for example, intranasally. Additionally, the compounds of the present invention can be administered transdermally. It will be obvious to those skilled in the art that the following dosage forms may comprise as the active component, either a compound of Formula I or a corresponding pharmaceutically acceptable salt of a compound of Formula I.

For preparing pharmaceutical compositions from the compounds of the present invention, pharmaceutically acceptable carriers can be either solid or liquid. Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules. A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material.

In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component.

In tablets, the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired.

The powders and tablets preferably contain from five or ten to about seventy percent of the active compound. Suitable carriers are magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, a low melting wax, cocoa butter, and the like. The term “preparation” is intended to include the formulation of the active compound with encapsulating material as a carrier providing a capsule in which the active component with or without other carriers, is surrounded by a carrier, which is thus in association with it. Similarly, cachets and lozenges are included. Tablets, powders, capsules, pills, cachets, and lozenges can be used as solid dosage forms suitable for oral administration.

For preparing suppositories, a low melting wax, such as a mixture of fatty acid glycerides or cocoa butter, is first melted, and the active component is dispersed homogeneously therein, as by stirring. The molten homogenous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify.

Liquid form preparations include solutions, suspensions, and emulsions, for example, water or water propylene glycol solutions. For parenteral injection, liquid preparations can be formulated in solution in aqueous polyethylene glycol solution.

Aqueous solutions suitable for oral use can be prepared by dissolving the active component in water and adding suitable colorants, flavors, stabilizing and thickening agents as desired.

Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or, synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, and other well-known suspending agents.

Also included are solid form preparations, which are intended to be converted, shortly before use, to liquid form preparations for oral administration. Such liquid forms include solutions, suspensions, and emulsions. These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like.

The pharmaceutical preparation is preferably in unit dosage form. In such form the preparation is divided into unit doses containing appropriate quantities of the active component. The unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself, or it can be the appropriate number of any of these in packaged form.

The quantity of active component in a unit dose preparation may be varied or adjusted from 0.1 mg to 100 mg preferably 0.5 mg to 100 mg according to the particular application and the potency of the active component. The composition can, if desired, also contain other compatible therapeutic agents.

In therapeutic use as antagonists of a virus, as agents for the treatment of infections caused by a virus or as agents for the treatment of diseases due to a virus, the compounds utilized in the pharmaceutical method of this invention are administered at the initial dosage of about 0.0 1 mg to about 100 mg/kg daily. A daily dose range of about 0.01-mg to about 10 mg/kg is preferred. The dosages, however, may be varied depending upon the requirements of the patient, the severity of the condition being treated, the compound being employed. Determination of the proper dosage for a particular situation is within the skill of the art. Generally, treatment is initiated with smaller dosages, which are less than the optimum dose of the compound. Thereafter, the dosage is increased by small increments until the optimum effect under the circumstances is reached. For convenience, the total daily dosage may be divided and administered in portions during the day, if desired.

General Procedure 1 (for Singleton Synthesis):

Reductive Amination of Aryl Amines with Aldehydes or Ketones.

Reagent 2 (1 eq.) was taken in a solvent (dichloromethane, 1,2-dichloroethane or tetrahydrofuran or diethyl ether) and to it reagent 1 (1 to 1.2 eq.) was added. To this solution cooled at 0° C. was added a reducing agent (sodium cyanoborohydride or sodium triacetoxyborohydride) (1 to 2 eq.). To it a drop of acetic acid was added and kept under stirring at room temperature for 6 to 24 hours. The excess hydride was quenched by adding methanol. The reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution, aqueous sodium bisulfite and brine; dried over anhydrous magnesium sulfate or sodium sulphate. Organic layer was concentrated and crude product was purified by flash silica gel chromatography to afford the final product. The products were characterized by spectral data. The compounds synthesized using this procedure are shown in Table 4.
General Procedure 2 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in trimethyl orthoformate (0.2 ml) followed by reagent 1 (0.05mmol) in trimethyl orthoformate (0.2 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot, 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (23 mg) was added manually to each vial. A solution of acetic acid (0.05 mmol) in dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromotography mass spec).
General Procedure 3 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in N,N-dimethylformamide (0.1 ml) followed by reagent 1 (0.05 mmol) in N,N-dimethylformamide (0.1 ml). Each vial was treated with trimethylorthoformate (0.2 ml) by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot, 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23 mg) was added manually to each vial. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).
General Procedure 4 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.5 mmol) in methanol (0.2 ml) followed by reagent 1 (0.2 mmol) in methanol (0.2 ml). To each vial was added, by Tecan™ liquid handling robot, a 1N solution of sodium cyanoborohydride in methanol (0.2 ml) and a 10% acetic acid in methanol (0.05 ml) solution. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General Procedure 5 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in 1,2-dichloroethane (0.2 ml) followed by reagent 1 (0.15 mmol) in 1,2-dichloroethane (0.1 ml). To each vial solid sodium triacetoxyborohydride (˜25mg) was added manually. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (S)₃H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General Procedure 6 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followed by reagent 1 (0.15 mmol) in methanol (0.1 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

General Procedure 7 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):

To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) followed by reagent 1 in N,N-dimethylformamide (0.32 ml) or methanol (0.2 ml). The vials were then concentrated overnight to dryness. Each vial was treated by Tecan™ liquid handling robot with reagent 1 (0.15 mmol) in methanol (0.1 ml) and methanol (0.2 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).

Synthesis of Compound 450: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added α,α′-dibromo-ortho-xylene (1.85 g, 7 mmol) followed by triethylamine (3.03 g, 30 mmol). The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (1.43 g).

Synthesis of Compound 451: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added phthaloyl dichloride (1.16 g, 6 mmol) followed by triethylamine (3.03 g, 30 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was quenched with sodium bicarbonate solution and the organic layer was separated. The crude product was purified by flash silica gel chromatography to give the title compound (0.51 g).

Synthesis of Compound 463: To compound 58 (0.25 g, 0.87 mmol) taken in tetrahydrofuran (10 mL) was added sodium hydride (60% in mineral oil, 0.035 g, 0.87 mmol). To it methyl iodide (0.25 g, 1.74 mmol) was added. The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (0.18 g).

Deprotection of t-butyloxycarbonyl group: The general procedure for the removal of tert-butyoxycarbonyl (Boc) group is as follows: To the compound taken a flask was added hydrochloric acid in an appropriate solvent (dioxane, methanol, 1,2-dichloromethane and the reaction was kept under shaking for 5 to 18 hours. Removal of volatiles furnished the corresponding product.

Reagents 1 are shown in Table 1.

TABLE 1 Aldehydes/ketones (reagent 1) No. Reagent 1 (aldehydes/ketones) 1 o-tolualdehyde 2 meta-tolualdehyde 3 para-tolualdehyde 4 2-fluorobenzaldehyde 5 3-fluorobenzaldehyde 6 4-fluorobenzaldehyde 7 4-tert-butylbenzaldehyde 8 α,α,α-Trilfluoro-o-tolualdehyde 9 α,α,α-Trilfluoro-m-tolualdehyde 10 α,α,α-Trilfluoro-p-tolualdehyde 11 o-anisaldehyde 12 m-anisaldehyde 13 p-anisaldehyde 14 Salicylaldehyde 15 3-hydroxybenzaldehyde 16 4-hydroxybenzaldehyde 17 2-chlorobenzaldehyde 18 3-chlorobenzaldehyde 19 4-chlorobenzaldehyde 20 3-benzyloxybenzaldehyde 21 4-benzyloxybenzaldehyde 22 2,3-dimethoxybenzaldehyde 23 2,4-dimethoxybenzaldehyde 24 2,5-dimethoxybenzaldehyde 25 2,6-dimethoxybenzaldehyde 26 3,4-dimethoxybenzaldehyde 27 3,5-dimethoxybenzaldehyde 28 1,4-Benzodioxan-6-carboxaldehyde 29 2,4-dimethylbenzaldehyde 30 2,5-dimethylbenzaldehyde 31 2,3-difluorobenzaldehyde 32 2,4-difluorobenzaldehyde 33 2,5-difluorobenzaldehyde 34 2,6-difluorobenzaldehyde 35 3,4-difluorobenzaldehyde 35 3,5-difluorobenzaldehyde 37 2,3,4-trifluorobenzaldehyde 38 2,3,6-trifluorobenzaldehyde 39 3-fluoro-2-methylbenzaldehyde 40 3-fluoro-p-anisaldehyde 41 2-pyridinecarboxaldehyde 42 3-pyridinecarboxaldehyde 43 4-pyridinecarboxaldehyde 44 4-pyridinecarboxaldehyde N-oxide 45 6-methyl-2-pyridinecarboixaldehyde 46 3-furaldehyde 47 2-furaldehyde 48 5-chloro-2-thiophenecarboxaldehyde 49 3-thiophenecarboxaldehyde 50 2-thiophenecarboxaldehyde 51 pyrrole-2-carboxaldehyde 52 1-methyl-2-pyrrolecarboxaldehyde 53 1-naphthaldehyde 54 2-naphthaldehyde 55 2-quinolinecarboxaldehyde 56 3-quinolinecarboxaldehyde 57 4-quinolinecarboxaldehyde 58 indole-3-carboxaldehyde 59 2-bromobenzaldehyde 60 2-chlorobenzaldehyde 61 2-ethoxybenzaldehyde 62 2-cyanobenzaldehyde 63 5-(2-chlorophenyl)furfural 64 5-(3-chlorophenyl)furfural 65 5-(4-chlorophenyl)furfural 66 2-thiazolecarboxaldehyde 67 2-imidazolecarboxaldehyde 68 4(5)-imidazolecaboxaldehyde 69 5-nitro-2-thiophenecarboxaldehyde 70 2-nitrobenzaldehyde 71 4-formyluracil 72 4-acetoxybenzaldehyde 73 4-(dimethylamino)benzaldehyde 74 1-acetyl-3-indolecarboxaldehyde 75 4-bromo-2-thiophenecarboxaldehyde 76 Piperonal 77 3-trifluoromethoxybenzaldehyde 78 4-chloro-3-nitro-benzaldehyde 79 Benzaldehyde 80 3-benzyloxybenzaldehyde 81 3-phenoxybenzaldehyde 82 2-butanone 83 2-Pentanone 84 3-Methyl-2-butanone 85 Tetrahydrothiophene-3-one 86 Tetrahydrothiopyran-4-one 87 Cycloheptanone 88 Cyclooctanone 89 Cyclohexylmethylketone 90 4-Methyl-2-pentanone 91 3-Pentanone 92 3-Hexanone 93 4-Hydroxy-3-methyl-2-butanon 94 2-Methoxyphenylacetone 95 4-nitrobenzaldehyde 96 4-(methylthio)benzaldehyde 97 Propionaldehyde 98 Isovaleraldehyde 99 3-(methylthio)propionaldehyde 100 1-phenyl-2-pentanone 101 Acetone 102 Cyclopropyl methyl ketone 103 Cyclohexanone 104 n-tert-butoxycarbonyl-4-piperidone 105 3,3,5,5-tetramethylcyclohexanone 106 1-decalone 107 4-cyclohexylcyclohexanone 108 2-norbornanone 109 4-tert-butylcyclohexanone 110 Cyclopentanone 111 2-adamantanone 112 Bicyclo[3,2,1]octan-2-one 113 1,1-dioxo-tetrahydro-thiopyran-4-one

Reagent 2 (amines) used in the above general procedures are shown in Table 2:

TABLE 2 No. Reagent 2 (amines) 1 Dibenzofuran-2-yl-methyl-amine 2 8-fluoro-dibenzofuran-2-yl-amine 3 8-chloro-dibenzofuran-2-yl-amine 4 8-amino-dibenzofuran-2-ol 5 3-methoxy-diebenzofuran-2-yl-amine 6 9H-Fluoren-3-yl-amine 7 9H-Fluorene-2-yl-amine 8 Dibenzofuran-4-yl-amine 9 Benzo[4,5]furo[2,3-H]pyridin-3-yl-amine 10 9-Ethyl-9H-carbazol-3-ylamine 11 3-Amino-carbazole-9-carboxylic acid tert-butyl ester 12 Dibenzofuran-2-yl-methyl-amine 13 Dibenzofuran-2-yl-dimethyl-amine 14 Dibenzothiophene-2-yl-amine 15 Dibenzothiophene-3-yl-amine 16 6-Amino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester 17 Dibenzo[1,4]dioxin-2-yl-amine 18 Phenoxanthiin-3-yl-amine 19 10-Oxa-9-thia-1-aza-anthracen-3-yl-amine 20 10H-Benzo-b]pyrido[2,3-e][1,4]oxazin-3-ylamine acetic acid, tert-butyl ester 21 Anthracen-2-yl-amine 22 10,111-Dihydro-5H-diebnzo[b,f]azepin-3-yl-amine 23 6,7,8,9-Tetrahydro-5H-carbazol-3-yl-amine 24 7-Amino-1-aza-phenoxathiin

The compounds of Formula I include:

1 (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3- yl)-amine 2 Cyclopentyl-(9H-fluoren-2-yl)-amine 3 (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine 4 N³-Cyclopentyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 5 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine 6 (2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran- 4-yl)-amine 7 Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine 8 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine 9 sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine 10 N²,N²-Dimethyl-N³-piperidin-4-yl-9H-fluorene-2,3- diamine 11 N³-(1-Benzyl-butyl)-N²,N²-dimethyl-9H-fluorene-2,3- diamine 12 (9H-Fluoren-2-yl)-piperidin-4-yl-amine 13 (1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine 14 sec-Butyl-(9H-fluoren-2-yl)-amine 15 (1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy- dibenzofuran-3-yl)-amine 16 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)- amine 17 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine 18 Adamantan-2-yl-dibenzofuran-2-yl-amine 19 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine 20 Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine 21 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine 22 Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine 23 Cyclopentyl-dibenzofuran-2-yl-amine 24 Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine 25 Cyclohexyl-(9H-fluoren-2-yl)-amine 26 Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine 27 Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine 28 Dibenzofuran-2-yl-dipropyl-amine 29 N³-(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N²,N²-dimethyl- 9H-fluorene-2,3-diamine 30 N³-Isopropyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 31 N²,N²-Dimethyl-N³-(tetrahydro-thiopyran-4-yl)-9H- fluorene-2,3-diamine 32 N³-Cyclohexyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 33 N³-Cycloheptyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 34 N³-(1-Ethyl-propyl)-N²,N²-dimethyl-9H-fluorene-2,3- diamine 35 N³-(1-Cyclopropyl-ethyl)-N²,N²-dimethyl-9H-fluorene-2,3- diamine 36 N³-sec-Butyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 37 (9H-Fluoren-2-yl)-isopropyl-amine 38 (9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine 39 Cycloheptyl-(9H-fluoren-2-yl)-amine 40 Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)- amine 41 Dibenzofuran-2-yl-piperidin-4-yl-amine 42 Dibenzofuran-2-yl-isopropyl-amine 43 Cyclohexyl-dibenzofuran-2-yl-amine 44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine 45 Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)- amine 46 Dibenzofuran-3-yl-piperidin-4-yl-amine 47 Dibenzoforan-3-yl-isopropyl-amine 48 Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine 49 Cyclohexyl-dibenzofuran-3-yl-amine 50 Cycloheptyl-dibenzofuran-3-yl-amine 51 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine 52 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine 53 Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine 54 Benzo[l,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine 55 Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6- ylmethyl)-amine 56 Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine 57 Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine 58 Dibenzoforan-2-yl-(2-methyl-benzyl)-amine 59 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine 60 Dibenzofuran-2-yl-(4-nitro-benzyl)-amine 61 Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine 62 Dibenzofuran-2-yl-(4-methyl-benzyl)-amine 63 Benzyl-dibenzofuran-2-yl-amine 64 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 65 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine 66 Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl- ethyl]-amine 67 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol 68 Dibenzofuran-2-yl-(1-ethyl-butyl)-amine 69 Dibenzofuran-2-yl-(1-ethyl-propyl)-amine 70 Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine 71 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine 72 Cyclooctyl-dibenzofuran-2-yl-amine 73 Cycloheptyl-dibenzofuran-2-yl-amine 74 Dibenzoforan-2-yl-(tetrahydro-thiopyran-4-yl)-amine 75 Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine 76 Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine 77 Dibenzofuran-2-yl-(1-methyl-butyl)-amine 78 sec-Butyl-dibenzofuran-2-yl-amine 79 Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine 80 Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine 81 Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine 82 N-(2-Fluoro-benzyl)-N′-methyl-dibenzoforan-2,8-diamine 83 N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8- diamine 84 N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8- diamine 85 N-(4-Methanesulfonyl-benzyl)-N′-methyl-diebnzofuran- 2,8-diamine 86 N-Methyl-N′-pyridin-4-ylmethyl-dibensofuran-2,8-diamine 87 N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine 88 Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine 89 (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine 90 (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 91 (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 92 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4- ylmethyl-amine 93 Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen- 6-yl)-amine 94 (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 95 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4- ylmethyl-amine 96 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen- 6-yl)-amine 97 Anthracen-2-yl-quinolin-4-ylmethyl-amine 98 Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine 99 Anthracen-2-yl-pyridin-4-ylmethyl-amine 100 Anthracen-2-yl-(2-methyl-benzyl)-amine 101 Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine 102 Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine 103 Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine 104 Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-amine 105 Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-benzyl)- amine 106 Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine 107 8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol 108 8-(2-Fluoro-benzylamino)-dibenzofuran2-ol 109 8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol 110 8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol 111 8-(2-Methyl-benzylamino)-dibenzofuran-2-ol 112 (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine 113 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 114 8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)- amine 115 (4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H- carbazol-3-yl)-amine 116 Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)- amine 117 Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)- amine 118 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine 119 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine 120 (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 121 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine 122 Diebnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine 123 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine 124 Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine 125 N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine 126 N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 127 N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 128 N-Benzyl-N′-methyl-dibenzofaran-2,8-diamine 129 2-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]- benzonitrile 130 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine 131 (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 132 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine 133 (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 134 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine 135 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine 136 Benzyl-phenoxathiin-3-yl-amine 137 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine 138 (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)- amine 139 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy- benzyl)-amine 140 Benzyl-(8-chloro-dibenzofuran-2-yl)-amine 141 (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine 142 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine 143 (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine 144 (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine 145 (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 146 (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine 147 Benzyl-(9H-fluoren-2-yl)-amine 148 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine 149 (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine 150 Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine 151 2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 152 Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine 153 Dibenzoforan-4-yl-(3,5-dimethoxy-benzyl)-amine 154 Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine 155 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine 156 Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine 157 N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 158 (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine 159 (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine 160 Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine 161 N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine 162 N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine 163 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine 164 Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine 165 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine 166 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine 167 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine 168 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine 169 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 170 (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 171 (8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2- ylmethyl)-amine 172 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine 173 (5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-3- yl)-amine 174 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine 175 (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine 176 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 177 (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine 178 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine 179 (9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine 180 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine 181 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine 182 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine 183 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 184 Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine 185 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine 186 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine 187 Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine 188 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine 189 Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine 190 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine 191 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine 192 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 193 N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8- diamine 194 N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8- diamine 195 N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 196 N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 197 N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 198 N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 199 N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 200 N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 201 N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl- dibenzofuran-2,8-diamine 202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine 203 (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)- amine 204 Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine 205 Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine 206 (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine 207 (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine 208 (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine 209 (2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine 210 (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine 211 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin- 3-yl-amine 212 Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)- amine 213 (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)- amine 214 (8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)- amine 215 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)- amine 216 (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)- amine 217 (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)- amine 218 (8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)- amine 219 (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)- amine 220 (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)- amine 221 (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 222 (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 223 (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 224 (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 225 (2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 226 (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 227 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H- carbazol-3-yl)-amine 228 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 229 (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)- amine 230 (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine 231 (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine 232 (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 233 (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 234 (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 235 (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 236 (2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 237 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren- 2-yl)-amine 238 (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)- amine 239 Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine 240 Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine 241 N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran- 2,8-diamine 242 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)- amine 243 (8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro- benzo[1,4]dioxin-6-ylmethyl)-amine 244 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 245 (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 246 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine 247 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine 248 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine 249 Anthracen-2-yl-(2-chloro-benzyl)-amine 250 Anthracen-2-yl-(2-fluoro-benzyl)-amine 251 Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine 252 (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine 253 2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol 254 Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine 255 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol 256 (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine 257 (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine 258 (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine 259 2-[(9H-Fluoren-2-ylamino)-methyl]-phenol 260 (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine 261 (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine 262 (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine 263 Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine 264 Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine 265 2-(Dibenzofuran-4-ylaminomethyl)-phenol 266 Dibenzoforan-4-yl-(2-methoxy-benzyl)-amine 267 (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)- amine 268 (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)- amine 269 (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 270 Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine 271 Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine 272 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine 273 (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)- amine 274 2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]- benzonitrile 275 (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 276 (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)- amine 277 (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 278 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine 279 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine 280 Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine 281 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl- amine 282 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl- amine 283 Dibenzofuran-2-yl-(2-nitro-benzyl)-amine 284 Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine 285 2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile 286 Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine 287 Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine 288 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine 289 Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine 290 (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 291 (2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 292 (4-Benzyloxy-benzyl)-(8-fluoro-dibenzoforan-2-yl)-amine 293 (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 294 (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 295 (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 296 (2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 297 4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 298 3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 299 Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine 300 (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine 301 (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 302 (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine 303 (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)- amine 304 (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)- amine 305 (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 306 (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 307 (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 308 (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 309 (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine 310 (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine 311 Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine 312 Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine 313 Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine 314 (4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 315 Dibenzofuran-2-yl-(3-methyl-benzyl)-amine 316 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine 317 3-(Dibenzoforan-2-ylaminomethyl)-phenol 318 (2-Chloro-benzyl)-dibenzofuran-2-yl-amine 319 Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine 320 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 321 (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine 322 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine 323 (8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine 324 (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 325 Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine 326 Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine 327 Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine 328 Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine 329 Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine 330 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine 331 Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine 332 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 333 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine 334 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine 335 (8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2- ylmethyl)-amine 336 (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl- benzyl)-amine 337 (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 338 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 339 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 340 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy- benzyl)-amine 341 Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine 342 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl- benzyl)-amine 343 (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)- amine 344 (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)- amine 345 (3,5-Difluoro-benzyl)-(8-fluoro-dibenzoforan-2-yl)- amine 346 (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 347 (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 348 (2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro- dibenzofuran-2-yl)-amine 349 (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 350 (2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 351 (2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 352 (2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 353 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro- dibenzofuran-2-yl)-amine 354 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 355 Dibenzofuran-2-yl-furan-2-ylmethyl-amine 356 Dibenzofuran-2-yl-furan-3-ylmethyl-amine 357 Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine 358 Dibenzoforan-2-yl-(4-methanesulfonyl-benzyl)-amine 359 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine 360 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine 361 Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine 362 Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 363 Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine 364 Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine 365 Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine 366 Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine 367 Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine 368 Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine 369 Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine 370 Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine 371 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine 372 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine 373 Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine 374 Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine 375 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine 376 Benzyl-dibenzothiohen-2-yl-amine 377 Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine 378 Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine 379 Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine 380 Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine 381 Dibenzothiohen-2-yl-(2,3,4-trifluoro-benzyl)-amine 382 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine 383 Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6- ylmethyl)-amine 384 Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 385 Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine 386 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine 387 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine 388 Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine 389 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine 390 Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine 391 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro- 2-methyl-benzyl)-amine 392 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl- benzyl)-amine 393 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4- dimethyl-benzyl)-amine 394 (4-tert-Butyl-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 395 (2-Chloro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 396 (2,6-Difluoro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 397 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2,3,6-trifluoro-benzyl)-amine 398 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2- fluoro-benzyl)-amine 399 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5- dimethoxy-benzyl)-amine 400 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 401 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4- methoxy-benzyl)-amine 402 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3- dimethoxy-benzyl)-amine 403 (2,5-difluoro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 404 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3- methoxy-benzyl)-amine 405 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,4- trifluoro-benzyl)-amine 406 (2-Bromo-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 407 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11- dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 408 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (3-fluoro-4-methoxy-benzyl)-amine 409 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2,5-dimethyl-benzyl)-amine 410 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- thiophen-3-ylmethyl-amine 411 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- naphthalen-1-ylmethyl-amine 412 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2-trifluoromethyl-benzyl)-amine 413 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- naphthalen-2-ylmethyl-amine 414 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2-ethoxy-benzyl)-amine 415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 416 (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 417 (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine 418 (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine 419 (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 420 (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine 421 (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 422 (3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 423 Benzyl-(10H-phenothiazin-2-yl)-amine 424 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 425 (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 426 (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine 427 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H- phenothiazin-2-yl)-amine 428 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)- amine 429 (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 430 (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine 431 (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)- amine 432 (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 433 (9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine 434 (9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine 435 (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine 436 (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine 437 (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine 438 (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 439 (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine 440 (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine 441 (9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine 442 (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 443 (9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin- 6-ylmethyl)-amine 444 (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine 445 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine 446 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine 447 Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6- ylmethyl)-amine 448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine 449 Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine 450 2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole 451 2-Dibenzofuran-2-yl--1H-isoindole-1,3-dione 452 Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine 453 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 454 Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine 455 Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine 456 Dibenzofuran-2-yl-(1-phenyl-butyl)-amine 457 Dibenzofuran-2-yl-phenethyl-amine 458 Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine

EXAMPLES

General proce- M + H MOLECULAR Example MOL STRUCTURE dure (APCI)⁻ FORMULA 1 7 282 C18H19NO2 2 7 250 C18H19N 3 7 250 C18H19N 4 7 293 C20H24N2 5 5 256 C16H17NO2 6 5 314 C18H19NO2S 7 5 310 C20H23NO2 8 5 284 C18H21NO2 9 5 270 C17H19NO2 10 7, 5 308 C20H25N3 11 5 371 C26H30N2 12 5, 7 265 C18H20N2 13 5 328 C24H25N 14 5, 7 238 C17H19N 15 5 346 C18H19NO4S 16 6 322 C22H27NO 17 6 320 C22H25NO 18 6 318 C22H23NO 19 6 348 C24H29NO 20 6 278 C19H19NO 21 6 322 C22H27NO 22 6 292 C20H21NO 23 6 252 C17H17NO 24 6, 5 296 C19H21NO2 25 6, 5 264 C19H21N 26 4 3609 C20H25NOS2 27 4 324 C22H29NO 28 4 268 C18H21NO 29 5 357 C20H24N2O2S 30 5, 7 267 C18H22N2 31 5, 7 325 C20H24N2S 32 5, 7 307 C21H26N2 33 5, 7 321 C22H28N2 34 5 295 C20H26N2 35 5 293 C20H24N2 36 5, 7 281 C19H24N2 37 5, 7 224 C16H17N 38 5 282 C18H19NS 39 5, 7 278 C20H23N 40 5 316 C17H17NO3S 41 5, 6 267 C17H18N2O 42 5, 6 226 C15H15NO 43 5, 6 266 C18H19NO 44 5 252 C17H17NO 45 5 316 C17H17NO3S 46 5 267 C17H18N2O 47 5 226 C15H15NO 48 5 284 C17H17NOS 49 5 266 C18H19NO 50 5 280 C19H21NO 51 5 308, 310 C19H14ClNO 52 2 353, 355 C19H13ClN2O3 53 2 358 C20H14F3NO2 54 2 318 C20H15NO3 55 2 332 C21H17NO3 56 2 334 C21H19NO3 57 2 342 C20H14F3NO 58 1, 2, 3 288 C20H17NO 59 2 280 C17H13NOS 60 2 319 C19H14N2O3 61 2 320 C20H17NOS 62 2 288 C20H17NO 63 2 274 C19H15NO 64 2 380 C26H21NO2 65 5 330 C23H23NO 66 5 332 C22H21NO2 67 5 270 C17H19NO2 68 5 268 C18H21NO 69 5 254 C17H19NO 70 5 268 C18H21NO 71 5 294 C20H23NO 72 5 294 C20H23NO 73 5, 6 280 C19H21NO 74 5, 6 284 C17H17NOS 75 5 270 C16H15NOS 76 5 254 C17H19NO 77 5 254 C17H19NO 78 5, 6 240 C16H17NO 79 3 293 C18H13FN2O 80 3 276 C17H13N2O 81 3 289 C19H16N2O 82 3 321 C20H17FN2O 83 3 354 C23H19N3O 84 3 353 C24H20N2O 85 3 381 C21H20N2O3S 86 3 304 C19H17N3O 87 3 317 C21H20N2O 88 3, 2 355 C23H18N2S 89 3 383 C20H18N2O2S2 90 3 339 C19H15FN2OS 91 3 325 C18H13FN2OS 92 3 358 C21H15N3OS 93 3 357 C22H16N2OS 94 3 385 C19H16N2O3S2 95 3 308 C17H13N3OS 96 3 321 C19H16N2OS 97 p 3 335 C24H18N2 98 3 362 C22H19NO2S 99 3 285 C20H16N2 100 3 298 C22H19N 101 3 322 C20H16FNO2 102 3 308 C19H14FNO2 103 3 341 C22H16N2O2 104 3 340 C23H17NO2 105 3 368 C20H17NO4S 106 3 291 C18H14N2O2 107 3 322 C20H16FNO2 108 3 308 C19H14FNO2 109 3 368 C20H17NO4S 110 3 291 C18H14N2O2 111 3 304 C20H17NO2 112 3 326, 328 C19H13ClFNO 113 3 359 C23H16ClNO 114 3 387 C20H16ClNO3S 115 3 355 C20H22N2O2S 124 2 292 C19H14FNO 125 2 333 C21H20N2O2 126 2 363 C22H22N2O3 127 2 359 C24H26N2O1 128 2 303 C20H18N2O1 129 2 328 C21H17N3O1 130 2 336 C20H17N1O2S1 116 3 278 C18H19N3 117 3 307 C19H15FN2O 118 2, 3 325 C22H16N2O 119 2 325 C22H16N2O 120 2 335 C21H19FN2O 121 2 317 C21H20N2O 122 2 325 C17H12N2O3S 123 2 281 C16H12N2OS 131 2 338, 340 C20H16N1O2Cl1 132 2 336 C20H17O2S1N1 133 2 366 C21H19O3N1S1 134 2 354 C20H16O2N1S1F1 135 2 362 C23H23O1N1S1 136 2 306 C19H15N1O1S1 137 2 350 C21H19N1O2S1 138 22 368, 370 C21H18N1O3Cl1 139 2 356, 358 C20H15N1O2Cl1F1 140 2 308, 310 C19H14NOCl 141 2 302 C21H19NO 142 2 315, 317 C15H11N2OClS 143 2 302 C21H19NO 144 2 332 C22H21NO2 145 2 320 C21H18NOF 146 2 328 C24H25N 147 2 272 C20H17N1 148 2 279 C 16H14N2S 149 2 316 C22H21NO 150 2 304 C20H17NO2 151 2 334 C20H13N2Ocl 152 2 304 C20H17NO2 153 2 334 C21H19NO3 154 2 322 C20H16NFO2 155 2 330 C23H23NO 156 2 318 C21H19NO2 157 2 333 C21H20N2O2 158 2 338, 340 C20H16NO2Cl 159 2 352, 354 C21H18NO2Cl 160 2 302 C21H19NO 161 2 309 C18H16N2OS 162 2 304 C19H17N3O 163 2 383, 385 C19H14BrNOS 164 2 357 C22H16N2OS 165 2 312 C17H13NOS2 166 2 321 C19H16H2OS 167 2 307 C18H14N2OS 168 2 307 C18H14N2OS 169 2 314, 316 C17H12ClNOS 170 2 379, 381 C21H19BrN2 171 2 323, 325 C19H15ClN2O 172 2 307 C19H18N2S 173 2 341, 342 C19H17ClN2S 174 2 302 C20H19N3 175 2 350, 352 C20H16BrN 176 2, 3 309, 311 C18H13ClN2O 177 2 323 C23H18N2 178 2 278 C18H15NS 179 2 287 C20H18N2 180 2 273 C19H16N2 181 2 273 C19H16N2 182 2 273 C19H16N2 183 2 309, 311 C18H13ClN2O 184 2 325 C22H16N2O 185 2 325 C22H16N2O 186 2 280 C17H13NOS 187 2 289 C19H16N2O 188 2 275 C18H14N2O 189 2 275 C18H14N2O 190 2 275 C18H14N2O 191 2 287, 289 C19H13BrClNO 192 2 309, 311 C18H13ClN2O 193 2 357 C20H15F3N2O 194 2 357 C20H15F3N2O 195 2 339 C20H16F2N2O 196 2 339 C20H16F2N2O 197 2 339 C20H16F2N2O 198 2 339 C20H16F2N2O 199 2 331 C22H22N2O 200 2 331 C22H22N2O 201 2 361 C22H20N2O3 202 2 338 C20H16FNOS 203 2 363 C19H11ClF3NO 204 2 360 C19H12F3NOS 205 2 360 C19H12F3NOS 206 2 342 C19H13F2NOS 207 2 342 C19H13F2NOS 208 2 342 C19H13F2NOS 209 2 342 C19H13F2NOS 210 2 334 C21H19NOS 211 2 364 C21H17NO3S 212 2 272 C16H14FNS 213 2 363 C19H11ClF3NO 214 2 345 C19H12ClF2NO 215 2 345 C19H12ClF2NO 216 2 345 C19H12ClF2NO 217 2 333 C22H21FN2 218 2 345 C19H12ClF2NO 219 2 355 C21H17F3N2 220 2 355 C21H17F3N2 221 2 337 C21H18F2N2 222 2 337 C21H18F2N2 223 2 337 C21H18F2N2 224 2 337 C21H18F2N2 225 2 329 C23H24N2 226 2 329 C23H24N2 227 2 359 C23H22N2O2 228 2 304 C21H18FN 229 2 337 C21H18ClNO 230 2 326 C20H14F3N 231 2 326 C20H14F3N 232 2 308 C20H15F2N 233 2 308 C20H15F2N 234 2 308 C20H15F2N 235 2 300 C22H21N 236 2 300 C22H21N 237 2 330 C22H19NO2 238 2 336, 338 C21H18ClNO 239 2 302 C21H19NO 240 2 306 C20H16FNO 241 2, 3 335 C21H19FN2O 242 2, 3 341 C20H15ClFNO 243 2 367 C21H16ClNO3 244 2 366 C21H19NO3S 245 2 366 C21H19NO3S 246 2 340, 342 C19H14ClNOS 247 2 336 C20H17NO2S 248 2 320 C20H17NOS 249 2 318, 320 C21H16ClN 250 2 302 C21H16FN 251 2 350 C21H19NO4 252 2 324, 326 C19H14ClNO2 253 2 306 C19H15NO3 254 2 320 C20H17NO3 255 2 317 C21H20N2O 256 2 319 C21H19FN2 257 2 315 C22H22N2 258 2 306, 308 C20H16ClN 259 2 288 C20H17NO 260 2 302 C21H19NO 261 2 340 C21H16F3N 262 2 290 C20H16FN 263 2 334 C21H19NO3 264 2 334 C21H19NO3 265 2 290 C19H15NO2 266 2 304 C20H17NO2 267 2 364 C22H21NO4 268 2 364 C22H21NO4 269 2 334 C21H19NO3 270 2 334 C21H19NO3 271 2 304 C20H17NO2 272 2 351, 353 C19H14BrNO 273 2 282 C16H12FN3O 274 2 317 C20H13FN2O 275 2 336 C21H18FNO2 276 2 338 C20H16FNOS 277 2 369, 371 C19H13BrFNO 278 2 343 C11H15FN2O 279 2 343 C22H15FN2O 280 2, 3 324 C23H17NO 281 2 342 C23H16FNO 282 2 342 C23H16FNO 283 2 319 C19H14N2O3 284 2 264 C16H13N3O 285 2 299 C20H14N2O 286 2 318 C21H19NO2 287 2 342 C20H14F3NO 288 2 330 C23H23NO 289 2 292 C19H14FNO 290 2 352 C21H18FNO3 291 2 352 C21H18FNO3 292 2 398 C26H20FNO2 293 2 398 C26H20FNO2 294 2 326, 328 C19H13ClFNO 295 2 326, 328 C19H13ClFNO 296 2 326, 328 C19H13ClFNO 297 2 308 C19H14FNO2 298 2, 3 308 C19H14FNO2 299 2 292 C19H14FNO 300 2 322 C20H16FNO2 301 2 322 C20H16FNO2 302 2 322 C20H16FNO2 303 2 360 C20H13F4NO 304 2 360 C20H13F4NO 305 2 348 C23H22FNO 306 2 310 C19H13F2NO 307 2 310 C19H13F2NO 308 2, 3 310 C19H13F2NO 309 2 306 C20H16FNO 310 2 306 C20H16FNO 311 2 334 C21H19NO3 312 2 334 C21H19NO3 313 2 334 C21H19NO3 314 2 380 C26H21NO2 315 2 288 C20H17NO 316 2 308, 310 C19H14ClNO 317 2 290 C19H15NO2 318 2 308, 310 C19H14ClNO 319 2 304 C20H17NO2 320 2 304 C20H17NO2 321 2 286 C21H19N 322 2 288 C20H17NO 323 2, 3 323 C20H16ClNO 324 2 319 C20H18N2S 325 2, 3 304 C20H17NO2 326 2 310 C19H13F2NO 327 2 310 CX19H13F2NO 328 2 310 C19H13F2NO 329 2 310 C19H13F2NO 330 2 298 C17H12FNOS 331 2 302 C21H19NO 332 2 298 C17H12FNOS 333 2 282 C17H12FNO2 334 2 282 C17H12FNO2 335 2 307 C19H15FN2O 336 2 370 C20H16FNO3S 337 2, 3 293 C18H13FN2O 338 2 293 C18H13FN2O 339 2 293 C18H13FN2O 340 2 340 C20H15F2NO2 341 2 302 C21H19NO 342 2, 3 324 C20H15F2NO 343 2 346 C19H11F4NO 344 2 346 C19H11F4NO 345 2 328 C19H12F3NO 346 2 328 C19H12F3NO 347 2 328 C129H12F3NO 348 2 328 C19H12F3NO 349 2 328 C19H12F3NO 350 2 328 C19H12F3NO 351 2 320 C21H19FNO 352 2 320 C21H18FNO 353 2 350 C21H16FNO3 354 2 352 C21H18FNO3 355 2 264 C17H13NO2 356 2 264 C17H13NO2 357 2 289 C19H16N2O 358 2, 3 352 C20H17NO3S 359 2, 3 275 C18H14N2O 360 2 275 C18H14N2O 361 2 275 C18H14N2O 362 2 322 C20H16FNO2 363 2, 3 306 C20H16FNO 364 2 328 C19H12F3NO 365 2 328 C19H12F3NO 366 2 310 C19H13F2NO 367 2 310 C19H13F2NO 368 2 334 C21H19NO3 369 2 304 C20H17NS 370 2 318 C21H19NS 371 2 346 C23H23NS 372 2 323, 325 C19H14ClNS 373 2 326 C19H13F2NS 374 2 344 C19H12F3NS 375 2 308 C19H14FNS 376 2 290 C19H15NS 377 2 320 C20H17NOS 378 2 350 C21H19NO2S 379 2 326 C19H13F2NS 380 2 320 C20H17NOS 381 2 344 C19H12F3NS 382 2 369 C19H14BrNS 383 2 348 C21H17NO2S 384 2 338 C20H16FNOS 385 2 318 C21H19NS 386 2 296 C17H13NS2 387 2 340 C23H17NS 388 2 358 C20H14F3NS 389 2 340 C23H17NS 390 2 334 C21H19NOS 391 2 333 C22H21FN2 392 2 315 C22H22N2 393 2 329 C23H24N2 394 2 357 C25H28N2 395 2 334, 336 C21H19ClN2 396 2 337 C21H18F2N2 397 2 355 C21H17F3N2 398 2 319 C21H19FN2 399 2 361 C23H24N2O2 400 2 301 C21H20N2 401 2 331 C22H22N2O 402 2 361 C23H24N2O2 403 2 337 C21H18F2N2 404 2 331 C22H22N2O 405 2 355 C21H17F3N2 406 2 380 C21H19BrN2 407 2 359 C23H22N2O2 408 2 349 C22H21FN2O 409 2 329 C23H24N2 410 2 307 C19H18N2S 411 2 351 C25H22N2 412 2 369 C22H19F3N2 413 2 351 C25H22N2 414 2 345 C23H24N2O 415 2 337 C20H17FN2S 416 2 333 C21H20N2S 417 2 361 C23H24N2S 418 2 338, 340 C19H15ClN2S 419 2 341 C19H14F2N2S 420 2 359 C19H13F3N2S 421 2 323 C19H15FN2S 422 2 365 C21H20N2O2S 423 2 305 C19H16N2S 424 2 335 C20H18N2OS 425 2 341 C19H14F2N2S 426 2 359 C19H13F2N2S 427 2 363 C21H18N2O2S 428 2 353 C20H17FN2O2 429 2 333 C21H20N2S 430 2 311 C17H14N2S2 431 2 373 C10H15F3N2S 432 2 305 C20H17FN2 433 2 287 C20H18NM2 434 2 301 C21H20N2 435 2 329 C23H24N2 436 2 306, 308 C19H15ClN2 437 2 309 C19H14F2N2 438 2 327 C19H13F3N2 439 2 333 C21H20N2O2 440 2 333 C21H20N2O2 441 2 309 C19H14F2N2 442 2 327 C19H13F3N2 443 2 331 C21H18N2O2 444 2 301 C21H20N2 445 2 323 C23H18N2 446 2 323 C23H18N2
*Analysis was done by LCMS. Number shown is M + 1. In all cases mass shown agrees with the expected mass for the compound shown.

The following compounds were prepared according to the general procedure 1:

MS (M + H) ¹H-NMR in CDCl₃unless Mp Example Structure APCI otherwise noted (δ) (° C.) 26 360 7.90 (1H, d); 7.51 (1H, d); 7.44-7.26 (4H, m); 6.95 (1H, d); 3.46 (4H, t); 2.58 (4H, t); 2.12 (6H, s); 1.91 (4H, quintet) — 55 332 7.87 (1H, d); 7.52 (1H, d); 7.38-7.46 (2H, quartet); 7.25-7.35 (1H, t); 7.14 (1H, s); 6.97-6.86 (3H, m); 6.76-6.81 (1H, d); 4.31 (2H, s) 4.25 (4H, br s) — 447 480 7.81 (1H, d); 7.48 (1H, d); 7.34-7.41 (2H, m); 7.22-7.28 (2H, t); 6.88-6.92 (1H, d); 6.74-6.86 (6H, m); 4.56 (4H, br s); 4.23 (8H, br s) — 448 376 7.85 (1H, d); 7.51 (1H, d); 7.26-7.42 (6H, m); 7.08 (2H, br s); 6.99-7.06 (3H, m); 4.60 (4H, br s) 109-110 59 280 7.86 (1H, d); 7.52 (1H, d); 7.38-7.44 (2H, m); 7.25-7.35 (3H, m); 7.19 (1H, s); 7.14 (1H, s); 6.81 (1H, s); 4.43 (2H, s) 62-63 56 334 7.86 (1H, d); 7.52 (1H, d); 7.29-7.42 (3H, m); 7.12 (1H, s); 6.78 (1H, d); 6.60 (2H, s); 6.41 (1H, t); 4.35 (2H, s); 3.79 (6H, s) 87-88 63 274 7.89 (1H, d); 7.53 (1H, d); 7.31-7.48 (8H, m); 7.18 (1H, s); 6.81 (1H, d); 4.43 (2H, s); 4.10 (1H, br s) 81-82 61 320 IN DMSO 7.93 (1H, d); 7.54 (1H, d); 7.17-7.42 (8H, m); 6.81 (1H, d); 6.22 (1H, t); 4.30 (2H, d); 2.41 (3H, s) 103-104 73 294 7.90 (1H, d); 7.51 (1H, d); 7.36-7.44 (2H, quartet); 7.26-7.33 (1H, t); 7.09 (1H, s); 6.72 (1H, d); 3.60 (2H, br m); 1.95 (2H, br m); 1.61 (12H, br m) 50-52 57 342 7.86 (1H, d); 7.63 (2H, d); 7.54 (3H, t); 7.43 (2H, quartet); 7.32 (1H, t); 7.11 (1H, s); 6.77 (1H, d); 4.46 (2H, s) 4.15 (1H, br s) 89-90 449 364 7.90 (1H, d); 7.53 (1H, d); 7.30-7.45 (7H, m); 7.03-7.18 (6H, m); 6.81 (1H, d); 4.39 (2H, s); 4.08 (1H, br s) 91-93 450 286 7.96 (1H, d); 7.31-7.55 (8H, m); 7.15 (1H, s); 6.83 (1H, d); 4.73 (4H, s) 193-195 451 314 IN DMSO 8.22 (1H, s); 8.13 (1H, d); 7.84-8.01 (5H, m); 7.75 (1H, d); 7.57 (2H, m); 7.43 (1H, t) 217-218 58 288 7.95 (1H, d); 7.57 (1H, d); 7.28-7.41 (4H, m); 7.12-7.20 (4H, m); 6.87 (1H, d); 6.03 (1H, t); 4.28 (2H, d); 2.36 (3H, s) 84-85 452 358 7.85 (1H, d); 7.37-7.53 (5H, m); 7.20-7.31 (3H, m); 7.14 (1H, s); 6.90 (1H, d); 4.43 (2H, s); 4.22 (1H, br s) 75-77 453 290 7.86 (1H, d); 7.55 (1H, d); 7.41-7.47 (3H, t); 7.18-7.34 (4H, m); 6.89-7.02 (3H, m); 4.52 (2H, s) 145-147 454 366 7.85 (1H, d); 7.51 (1H, d); 7.26-7.44 (6H, m); 7.17 (1H d); 7.06-7.13 (3H, m); 6.99-7.02 (2H, m); 6.95 (1H, s); 6.77 (1H, dd) 4.40 (2H, s); 4.17 (1H, s) 93-94 54 316 7.86 (1H, d); 7.51 (1H, d); 7.26-7.43 (3H, m); 7.14 (1H, s); 6.87-6.92 (2H, m); 6.77-6.81 (2H, m); 5.96 (2H, s); 4.32 (2H, s); 4.12 (1H, br s) 85-86 455 302 7.99 (1H, d); 7.52 (1H, d); 7.44-7.39 (2H, m); 7.32-7.15 (6H, m); 6.89 (1H, s); 4.52 (2H, s); 3.09 (3H, s); 2.37 (3H, s) 456 316 7.77 (1H, d); 7.48-7.21 (9H, m); 7.00 (1H, d); 6.70 (1H, dd); 4.40 (1H, t); 4.13 (1H, br s) 1.88-1.78 (2H, m); 1.51-1.38 (2H, m); 0.97 (3H, t) — 457 392 7.87 (1H, d); 7.53-7.26 (9H, m); 7.16 (1H, d); 6.77 (1H, dd); 3.50 (2H, t); 3.00 (2H, t) — 458 288 7.76 (1H, d); 7.48-7.21 (9H, m); 6.99 (1H, d); 6.70 (1H, dd); 4.57 (1H, q); 4.07 (1H, br s); 1.57 (3H, d) 94-95 202 338 7.09 (4H, m), 7.09 (3H, m), 6.96 (1H, d), 6.30 (2H, m), 4.26 (sH, s), 2.26 (3H, s) — 210 334 7.26 (1H, s), 7.18 (1H, d), 7.09 (s, 1H), 7.07 (1H, s), 7.02 (1H, s), 6.95 (1H, s), 6.97 (2H, s), 6.96 (1H, s), 6.87 (1H, d), 6.36 (1H, s), 6.34 (1H, d), 4.2 (2H, s), 2.31 (6H, s). — 135 362 7.26 (1H, s), 7.18 (1H, d), 7.09 (s, 1H), 7.07 (1H, s), 7.02 (1H, s), 6.95 (1H, s), 6.97 (2H, s), 6.96 (1H, s), 6.87 (1H, d), 6.36 (1H, s), 6.34 (1H, d), 4.2 (2H, s), 1.3 (9H, s). — 146 328 7.61 (d, 1H), 7.58 (d, 1H), 7.45 (d, 1H), 7.39 (d, 1H), 7.37 (s, 1H), 7.34 (s, 1H), 7.32 (s, 1H), 7.28 (d, 1H), 7.16 (t, 1H), 6.86 (s, 1H), 6.68 (dd, 1H), 4.35 (s, 3H), 3.8 (s, 2H), 1.31 (s, 9H). — 90 339 8.15 (d, 1H), 7.22 (s, 1H), 7.05 (m, 3H), 6.98 (m, 2H), 6.88 (d, 1H), 6.32 (d, 1H), 6.29 (s, 1H), 4.3 (s, 2H), 2.3 (s, 3H). —

Antiviral Activity Assays:

Screening assays: Anti-herpes simplex virus-1 (HSV) activity is determined in a yield reduction assay utilizing a recombinant HSV (HSV US3::pgC-lacZ) which expresses E. coli β-galactosidase (β-gal) under the control of an HSV late gene promoter (Fink, D. J.; Sternberg, L. R.; Weber, P. C.; Mata, M.; Goins, W. F.; Glorioso, J. C. Human Gene Therapy 3:11-19, 1992). Vero (African Green Monkey kidney) cells are infected at a multiplicity of infection of 0.01 with the virus, and serial dilutions of the compound in dimethyl sulfoxide (DMSO) are added. The final concentration of DMSO in all wells is 1%. DMSO is added to control wells. The infection is allowed to proceed for 2 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC₅₀is defined as the concentration of drug that produces a 50% reduction in β-gal production relative to control wells.

Anti-human cytomegalovirus (HCMV) activity is determined in a yield reduction assay utilizing a recombinant HCMV (RC256) that produces β-gal (Spaete, R. R.; Mocarski, E. S. Proceedings of the National Academy of Sciences USA 84:7213-7217, 1987). Primary human diploid fibroblasts (HFF cells) are infected at an moi of 0.01 with RC256, and serial dilutions of the compound in DMSO are added. The final concentration of DMSO in all wells is 1%. The infection is allowed to proceed for 7 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC₅₀is defined as the concentration of compound that produces a 50% reduction in β-gal production relative to control wells. TC₅₀is defined as concentration of compound that produces cytotoxicity in 50% of uninfected cells.

Secondary yield reduction assays: To determine the activity of compounds against HSV, Vero cells are plated in 6 well dishes at a density of 5×105 cells/well. Cells are infected at a multiplicity of infection of 0.01 with HSV (strain Syn17+). 30μL of one of six threefold serial dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 2 days. Aliquots of the supernatant are harvested, and the virus titer determined. Vero cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the monolayer for 1.5 hours, after which it is aspirated and replaced with growth medium containing 0.5% methylcellulose. Plaques are allowed to develop for 5 days, at which time the medium aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.

To determine the activity of compounds against CMV, HFF cells, plated in 24 well plates at 1×10⁵cells/well, are infected with CMV (strain AD169) at an moi of 0.01. 10 μL of one of six threefold dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 7 days. Aliquots of the supernatant of infected cells are harvested and the virus titer determined. HFF cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the cells for 2 hours, at which time the inoculum is aspirated and replaced with growth medium containing 0.5% methylcellulose. The plaques are allowed to develop for 7-10 days, at which time the medium is aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.

Cellular toxicity assays: Cellular toxicity is measured in Ad cells. Cells are plated in 96 well plates at 1×10⁴cells/ well. Serial dilutions of compounds are added to the wells in DMSO, with the final concentration of DMSO in all wells at 1%, in a total volume of 200 μL. The plates are maintained in a 37° C. incubator for 7 days. 50 μL of a solution of XTT (sodium-3[1-phenyl-amino-carbonyl)-3,-tetrazolium]-bis(bis(4-methoxy-6-nitro)-benzene sulfonic acid hydrate) (3×10⁻⁴mg/ml) is added to each well, and the plates returned to the incubator for 4 hours, after which the A₄₅₀(absorbance at wavelength of 450 nm) for each well is measured in a plate reader. (Roehm, N. W., et al J. Immunol. Meth. 142:257-265, 1991). Toxicity is determined by comparison of the OD (optical density) of a well containing compound to the OD of wells containing DMSO only.

The effect of test compounds on cellular DNA synthesis is measured in a ¹⁴C-thymidine incorporation assay, utilizing scintillation proximity assay technology. Cells are plated at 2×10⁴cells/well in Amersham Cytostar 96 well scintillating microplates. The following day, serial dilutions of test compounds in DMSO are added to the wells, along with 0.1 μCi/well of [methyl-¹⁴C]-thymidine (specific activity 50-62 mCi/mmol). The plates are counted immediately in a μBeta scintillation counter (Wallac), to determine background, then placed in a 37° C. incubator for 7 days. The plates are removed from the incubator at intervals and the thymidine incorporation into the cellular DNA determined by scintillation counting. Percent inhibition is determined by comparing ¹⁴C incorporation in wells containing test compound to incorporation in wells containing DMSO only.

Table 3 contains the results of the antiviral efficacy (ISV: EC₅₀, TC₅₀and TI) screening results, where TI is the therapeutic index (TC₅₀/EC₅₀).

TABLE 3 Antiviral Efficacy in a Yield Reduction Assay (HSV-1) Antiviral Efficacy (Vero Cells) Example EC₅₀(μM) TC₅₀(μM) TI (EC₅₀/TC₅₀) 60 0.5 >100 >200 57 0.81 >100 >124 56 0.7 >100 >143 208 0.26 >100 >385 217 0.32 >100 >313 139 0.4 >100 >250 150 0.85 >100 >118 93 1.3 >100 >77 Reference 0.2 >100 >500 Agent (Acyclovir)

Table 4 contains the results of the antiviral efficacy (HSV: EC₅₀, TC₅₀and TI) screening results, where TI is the therapeutic index (TC₅₀/EC₅₀).

TABLE 4 Antiviral Efficacy in a Yield Reduction Assay (CMV) Antiviral Efficacy (HFF Cells) Example EC₅₀(μM) TC₅₀(μM) TI (EC₅₀/TC₅₀) 61 2.9 >100 >35 57 1.7 >100 >59 65 3.0 >100 >33 60 1.3 >100 >77 Reference 2.6 >100 >39 Agent (Ganciclovir)

Tables 3 and 4 indicates that the compounds of the present invention have good to excellent activity in HSV infected cells from HSV pathogenecity at μM to sub-μconcentrations.

While the forms of the invention herein disclosed constitute presently preferred embodiments, many others are possible. It is not intended herein to mention all of the possible equivalent forms or ramifications of the invention. It is understood that the terms used herein are merely descriptive, rather than limiting, and that various changes may be made without departing from the spirit or scope of the invention.

Claims

1. A compound of Formula I or a pharmaceutically acceptable salt thereof wherein:

X═O, (CH2)m, S, SO, SO2, NH, NR8 or a chemical bond;

Y═O, (CH2)m, S, SO, SO2, NH, NR8;

Z=N, NH, O, NHR8, NR8, S, SO, SO2;

n=an integer of from 0 to 2;

m=an integer of 1,2, or 3;

R1, R2, R3, R4, R5 independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF3, OCF3, aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O or S;

Ar=phenyl, substituted phenyl, benzoheterocyclic ring, substituted benzoheterocyclic ring, heterocyclic ring, or substituted heterocyclic ring, which have substitutions R6 or R7;

R6 and R7 are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF3, aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S;

R6 and R7 may also form a ring, optionally cycloalkyl or aryl or substituted aryl;

R8 is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.

2. The compound of claim 1 having Formula II.

3. The compound of claim 1 having Formula III.

4. The compound of claim 1 having Formula IV.

5. The compound of claim 1 having Formula V.

6. The compound of claim 1 having Formula VI.

7. The compound of claim 1 having Formula VII.

8. A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.

9. A pharmaceutical composition for the treatment of infection or disease caused by a virus, which comprises an amount of the compound of claim 1 in the range of about 1 to about 50 mg/kg-day or up to 3 g per day and a pharmaceutically effective carrier.

10. A method of treatment of infection or disease caused by a virus, which comprises administering to a subject in need of such treatment a composition of claim 1.

11. The composition of claim 8 wherein the virus is a Herpes virus.

12. The composition of claim 9 wherein the virus is a Herpes virus.

13. The method of claim 10 wherein the virus is a Herpes virus.

14. 1 (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)- amine 2 Cyclopentyl-(9H-fluoren-2-yl)-amine 3 (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine 4 N3-Cyclopentyl-N2,N2-dimethyl-9H-fluorene-2,3-diamine 5 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine 6 (2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-4- yl)-amine 7 Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine 8 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine 9 sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine 10 N2,N2-Dimethyl-N3-piperidin-4-yl-9H-fluorene-2,3-diamine 11 N3-(1-Benzyl-butyl)-N2,N2-dimethyl-9H-fluorene-2,3- diamine 12 (9H-Fluoren-2-yl)-piperidin-4-yl-amine 13 (1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine 14 sec-Butyl-(9H-fluoren-2-yl)-amine 15 (1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy- dibenzofuran-3-yl)-amine 16 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine 17 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine 18 Adamantan-2-yl-dibenzofuran-2-yl-amine 19 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine 20 Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine 21 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine 22 Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine 23 Cyclopentyl-dibenzofuran-2-yl-amine 24 Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine 25 Cyclohexyl-(9H-fluoren-2-yl)-amine 26 Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine 27 Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine 28 Dibenzofuran-2-yl-dipropyl-amine 29 N3-(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N2,N2- dimethyl-9H-fluorene-2,3-diamine 30 N3-Isopropyl-N2,N2-dimethyl-9H-fluorene-2,3-diamine 31 N2,N2-Dimethyl-N3-(tetrahydro-thiopyran-4-yl)-9H- fluorene-2,3-diamine 32 N3-Cyclohexyl-N2,N2-dimethyl-9H-fluorene-2,3-diamine 33 N3-Cycloheptyl-N2,N2-dimethyl-9H-fluorene-2,3-diamine 34 N3-(1-Ethyl-propyl)-N2,N2-dimethyl-9H-fluorene-2,3- diamine 35 N3-(1-Cyclopropyl-ethyl)-N2,N2-dimethyl-9H-fluorene- 2,3-diamine 36 N3-sec-Butyl-N2,N2-dimethyl-9H-fluorene-2,3-diamine 37 (9H-Fluoren-2-yl)-isopropyl-amine 38 (9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine 39 Cycloheptyl-(9H-fluoren-2-yl)-amine 40 Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4- yl)-amine 41 Dibenzofuran-2-yl-piperidin-4-yl-amine 42 Dibenzofuran-2-yl-isopropyl-amine 43 Cyclohexyl-dibenzofuran-2-yl-amine 44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine 45 Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4- yl)-amine 46 Dibenzofuran-3-yl-piperidin-4-yl-amine 47 Dibenzofuran-3-yl-isopropyl-amine 48 Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine 49 Cyclohexyl-dibenzofuran-3-yl-amine 50 Cycloheptyl-dibenzofuran-3-yl-amine 51 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine 52 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine 53 Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine 54 Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine 55 Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6- ylmethyl)-amine 56 Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine 57 Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine 58 Dibenzofuran-2-yl-(2-methyl-benzyl)-amine 59 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine 60 Dibenzofuran-2-yl-(4-nitro-benzyl)-amine 61 Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine 62 Dibenzofuran-2-yl-(4-methyl-benzyl)-amine 63 Benzyl-dibenzofuran-2-yl-amine 64 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 65 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine 66 Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl- ethyl]-amine 67 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol 68 Dibenzofuran-2-yl-(1-ethyl-butyl)-amine 69 Dibenzofuran-2-yl-(1-ethyl-propyl)-amine 70 Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine 71 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine 72 Cyclooctyl-dibenzofuran-2-yl-amine 73 Cycloheptyl-dibenzofuran-2-yl-amine 74 Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine 75 Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine 76 Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine 77 Dibenzofuran-2-yl-(1-methyl-butyl)-amine 78 sec-Butyl-dibenzofuran-2-yl-amine 79 Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine 80 Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine 81 Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine 82 N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 83 N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine 84 N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran- 2,8-diamine 85 N-(4-Methanesulfonyl-benzyl)-N′-methyl-diebnzofuran- 2,8-diamine 86 N-Methyl-N′-pyridin-4-ylmethyl-dibensofuran-2,8-diamine 87 N-Methyl-N'-(2-methyl-benzyl)-dibenzofuran-2,8-diamine 88 Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine 89 (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine 90 (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 91 (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 92 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4- ylmethyl-amine 93 Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen- 6-yl)-amine 94 (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza- anthracen-6-yl)-amine 95 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4- ylmethyl-amine 96 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen- 6-yl)-amine 97 Anthracen-2-yl-quinolin-4-ylmethyl-amine 98 Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine 99 Anthracen-2-yl-pyridin-4-ylmethyl-amine 100 Anthracen-2-yl-(2-methyl-benzyl)-amine 101 Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine 102 Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine 103 Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine 104 Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl- amine 105 Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl- benzyl)-amine 106 Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine 107 8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol 108 8-(2-Fluoro-benzylamino)-dibenzofuran2-ol 109 8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol 110 8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol 111 8-(2-Methyl-benzylamino)-dibenzofuran-2-ol 112 (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine 113 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 114 8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)- amine 115 (4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H- carbazol-3-yl)-amine 116 Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol- 3-yl)-amine 117 Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl- benzyl)-amine 118 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine 119 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine 120 (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 121 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine 122 Diebnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine 123 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine 124 Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine 125 N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran- 2,8-diamine 126 N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran- 2,8-diamine 127 N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran- 2,8-diamine 128 N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine 129 2-[(8-Methylamino-dibenzofuran-2-ylamino)- methyl]-benzonitrile 130 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine 131 (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 132 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine 133 (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 134 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine 135 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine 136 Benzyl-phenoxathiin-3-yl-amine 137 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine 138 (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)- amine 139 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy- benzyl)-amine 140 Benzyl-(8-chloro-dibenzofuran-2-yl)-amine 141 (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine 142 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine 143 (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine 144 (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine 145 (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 146 (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine 147 Benzyl-(9H-fluoren-2-yl)-amine 148 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine 149 (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine 150 Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine 151 2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]- benzonitrile 152 Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine 153 Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine 154 Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine 155 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine 156 Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine 157 N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 158 (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine 159 (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine 160 Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine 161 N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8- diamine 162 N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8- diamine 163 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine 164 Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine 165 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine 166 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine 167 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine 168 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine 169 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 170 (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 171 (8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2- ylmethyl)-amine 172 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine 173 (5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol- 3-yl)-amine 174 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine 175 (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine 176 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 177 (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine 178 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine 179 (9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine 180 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine 181 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine 182 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine 183 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 184 Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine 185 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine 186 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine 187 Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine 188 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine 189 Diberizofuran-4-yl-pyridin-3-ylmethyl-amine 190 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine 191 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine 192 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 193 N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8- diamine 194 N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8- diamine 195 N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 196 N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 197 N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 198 N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 199 N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 200 N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8- diamine 201 N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)- N′-methyl-dibenzofuran-2,8-diamine 202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine 203 (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)- amine 204 Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine 205 Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine 206 (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine 207 (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine 208 (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine 209 (2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine 210 (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine 211 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)- phenoxathiin-3-yl-amine 212 Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-amine 213 (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)- amine 214 (8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)- amine 215 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)- amine 216 (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)- amine 217 (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)- amine 218 (8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)- amine 219 (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)- amine 220 (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)- amine 221 (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 222 (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 223 (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 224 (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 225 (2,5-Dimethyl-benzyI)-(9-ethyl-9H-carbazol-3-yl)-amine 226 (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 227 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl- 9H-carbazol-3-yl)-amine 228 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 229 (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)- amine 230 (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine 231 (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine 232 (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 233 (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 234 (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 235 (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 236 (2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 237 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren- 2-yl)-amine 238 (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)- amine 239 Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine 240 Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine 241 N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran- 2,8-diamine 242 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl- benzyl)-amine 243 (8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro- benzo[1,4]dioxin-6-ylmethyl)-amine 244 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 245 (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 246 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine 247 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine 248 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine 249 Anthracen-2-yl-(2-chloro-benzyl)-amine 250 Anthracen-2-yl-(2-fluoro-benzyl)-amine 251 Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine 252 (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine 253 2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol 254 Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine 255 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol 256 (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine 257 (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine 258 (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine 259 2-[(9H-Fluoren-2-ylamino)-methyl]-phenol 260 (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine 261 (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine 262 (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine 263 Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine 264 Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine 265 2-(Dibenzofuran-4-ylaminomethyl)-phenol 266 Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine 267 (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)- amine 268 (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)- amine 269 (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 270 Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine 271 Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine 272 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine 273 (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)- amine 274 2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]- benzonitrile 275 (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 276 (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)- amine 277 (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 278 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine 279 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine 280 Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine 281 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl- amine 282 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl- amine 283 Dibenzoforan-2-yl-(2-nitro-benzyl)-amine 284 Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine 285 2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile 286 Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine 287 Dibenzoforan-2-yl-(3-trifluoromethyl-benzyl)-amine 288 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine 289 Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine 290 (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 291 (2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 292 (4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 293 (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 294 (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 295 (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 296 (2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 297 4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 298 3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 299 Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine 300 (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine 301 (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 302 (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine 303 (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl- benzyl)-amine 304 (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl- benzyl)-amine 305 (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 306 (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 307 (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 308 (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 309 (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine 310 (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine 311 Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine 312 Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine 313 Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine 314 (4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 315 Dibenzofuran-2-yl-(3-methyl-benzyl)-amine 316 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine 317 3-(Dibenzofuran-2-ylaminomethyl)-phenol 318 (2-Chloro-benzyl)-dibenzofuran-2-yl-amine 319 Dibenzoforan-2-yl-(3-methoxy-benzyl)-amine 320 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 321 (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine 322 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine 323 (8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine 324 (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 325 Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine 326 Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine 327 Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine 328 Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine 329 Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine 330 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine 331 Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine 332 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 333 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine 334 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine 335 (8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2- ylmethyl)-amine 336 (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl- benzyl)-amine 337 (8-Fluoro-dibenzofaran-2-yl)-pyridin-4-ylmethyl-amine 338 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 339 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 340 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy- benzyl)-amine 341 Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine 342 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl- benzyl)-amine 343 (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)- amine 344 (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)- amine 345 (3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 346 (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 347 (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 348 (2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro- dibenzofuran-2-yl)-amine 349 (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 350 (2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 351 (2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 352 (2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 353 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro- dibenzofuran-2-yl)-amine 354 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)- amine 355 Dibenzofuran-2-yl-furan-2-ylmethyl-amine 356 Dibenzofuran-2-yl-furan-3-ylmethyl-amine 357 Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine 358 Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine 359 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine 360 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine 361 Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine 362 Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 363 Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine 364 Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine 365 Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine 366 Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine 367 Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine 368 Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine 369 Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine 370 Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine 371 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine 372 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine 373 Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine 374 Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine 375 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine 376 Benzyl-dibenzothiohen-2-yl-amine 377 Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine 378 Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine 379 Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine 380 Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine 381 Dibenzothiohen-2-yl-(2,3,4-trifluoro-benzyl)-amine 382 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine 383 Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6- ylmethyl)-amine 384 Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)- amine 385 Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine 386 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine 387 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine 388 Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine 389 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine 390 Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine 391 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro- 2-methyl-benzyl)-amine 392 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl- benzyl)-amine 393 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4- dimethyl-benzyl)-amine 394 (4-tert-Butyl-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 395 (2-Chloro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 396 (2,6-Difluoro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 397 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2,3,6-trifluoro-benzyl)-amine 398 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2- fluoro-benzyl)-amine 399 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (3,5-dimethoxy-benzyl)-amine 400 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2- yl)-amine 401 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4- methoxy-benzyl)-amine 402 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3- dimethoxy-benzyl)-amine 403 (2,5-difluoro-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 404 (10,11-Dihydro-5H-dibenz[b,f)azepin-2-yl)-(3- methoxy-benzyl)-amine 405 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2,3,4-trifluoro-benzyl)-amine 406 (2-Bromo-benzyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 407 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H- dibenz[b,f]azepin-2-yl)-amine 408 (10,11-Dihydro-5H-dibenz[b,f)azepin-2-yl)-(3- fluoro-4-methoxy-benzyl)-amine 409 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5- dimethyl-benzyl)-amine 410 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen- 3-ylmethyl-amine 411 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- naphthalen-1-ylmethyl-amine 412 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- (2-trifluoromethyl-benzyl)-amine 413 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)- naphthalen-2-ylmethyl-amine 414 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2- ethoxy-benzyl)-amine 415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 416 (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 417 (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine 418 (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine 419 (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 420 (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine 421 (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 422 (3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 423 Benzyl-(10H-phenothiazin-2-yl)-amine 424 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 425 (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 426 (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine 427 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H- phenothiazin-2-yl)-amine 428 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)- amine 429 (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 430 (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine 431 (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine 432 (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 433 (9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine 434 (9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine 435 (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine 436 (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine 437 (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine 438 (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 439 (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine 440 (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine 441 (9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine 442 (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 443 (9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-6- ylmethyl)-amine 444 (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine 445 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine 446 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine 447 Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin- 6-ylmethyl)-amine 448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine 449 Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine 450 2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole 451 2-Dibenzofuran-2-yl--1H-isoindole-1,3-dione 452 Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine 453 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 454 Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine 455 Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine 456 Dibenzofuran-2-yl-(1-phenyl-butyl)-amine 457 Dibenzofuran-2-yl-phenethyl-amine 458 Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine