Two Of The Cyclos Share At Least Three Ring Carbons (e.g., Benzomorphans, Etc.) Patents (Class 546/97)
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Patent number: 6251916Abstract: The present invention provides novel compounds and pharmaceutical compositions thereof useful in the treatment of pain. The compounds of the present invention are azaadamantanes, azanoradamantanes and azahomoadamantanes.Type: GrantFiled: May 9, 2000Date of Patent: June 26, 2001Assignee: UCB, S. A.Inventors: Gurmit Grewal, Anna Toy-Palmer, Xiong Cai, George Mark Latham
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Patent number: 6245777Abstract: The present invention relates to N-(5-phenyl-tetrahydrofuranyl)methyl- and N-(6-phenyl-tetrahydropyranyl)methyl-substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-10-ols of general formula 1, processes for preparing such compounds, pharmaceutical compositions containing such compounds and methods for using such compounds for the treatment of various diseases caused by a functional disorder resulting from overstimulation.Type: GrantFiled: February 22, 2000Date of Patent: June 12, 2001Assignee: Boehringer Ingelheim Pharma KGInventors: Matthias Grauert, Hans Briem, Matthias Hoffmann, Adrian Carter, Thomas Weiser, Wolf-Dietrich Bechtel, Rainer Palluk
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Patent number: 6211372Abstract: A compound of the formula: wherein X′ is nitrogen or carbon bonded to a substituent species characterized as having a sigma m value greater than 0, less than 0 or 0; X is nitrogen or carbon bonded to a substituent species characterized as having a sigma m value equal to 0; A, A′ and A″ are individually substituent species characterized as having a sigma m value greater than 0, less than 0 or 0; Z′ is a substituent other than hydrogen; j is an integer from 0 to 5; and the wavy line in the structure indicates that the compound can exist in the form of an enantiomer or a diasteromer; Z″ is hydrogen or a substituent other than hydrogen; Y is C═O, C(OH)R′ or C—A, where R′ is hydrogen or lower alkyl is provided.Type: GrantFiled: July 21, 1999Date of Patent: April 3, 2001Inventors: Peter Anthony Crooks, Niranjan Madhukar Deo
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Patent number: 6159986Abstract: Therapies and compounds for the inhibition of memory loss. In one embodiment, a combination of Huperzine A and hypericin is employed.Type: GrantFiled: November 2, 1999Date of Patent: December 12, 2000Inventor: David A. Altman
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Patent number: 6140502Abstract: A process for the re-racemisation of a (-)-2-phenylmethyl-3,3-dimethyl-piperidin-4-on derivative wherein a (-)-2-phenylmethyl-3,3-dimethyl-piperidin-4-on derivative of the formula 8.sub.BwhereinR.sub.2 denotes hydrogen C.sub.1 -C.sub.6 -alkyl, halogen, C.sub.1 -C.sub.8 -alkoxy, a benzoyl group bound via an oxygen or an alkylcarboxyl group having a straight chained or branched C.sub.1 -C.sub.6 -lower alkyl group--wherein the alkyl group may optionally be substituted by one or more halogen atoms which may be identical or different;is heated to yield a racemic mixture of compounds of the formulae 8.sub.A and 8.sub.Type: GrantFiled: November 18, 1999Date of Patent: October 31, 2000Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Hanfried Baltes
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Patent number: 6136980Abstract: The present invention relates to new processes for preparing norbenzomorphan, the central intermediate step in the preparation of pharmaceutically useful benzomorphan derivatives of general formula 1 ##STR1## especially (-)-(1R,5S,2"R)-3'-hydroxy-2-(2-methoxypropyl)-5,9,9-trimethyl-6,7-benzomo rphan or [(-)-(2R, 6S,2'R)-3-(2-methoxypropyl)-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-me thano-benzo[.alpha.]oxacin-9-ol] (BIII 277).Type: GrantFiled: November 18, 1999Date of Patent: October 24, 2000Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Hanfried Baltes
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Patent number: 6124459Abstract: The present invention relates to a new process for preparing norbenzomorphane derivatives of general formula 1 ##STR1##Type: GrantFiled: May 17, 1999Date of Patent: September 26, 2000Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Hanfried Baltes, Juergen Schnaubelt
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Patent number: 6124312Abstract: The present invention provides heterocyclic 2-aza-bicyclo[2.2.1]heptane compounds which are useful for modulating a muscarinic ptor.Type: GrantFiled: June 1, 1999Date of Patent: September 26, 2000Assignee: Eli Lilly and CompanyInventors: Charles H Mitch, Steven J Quimby, Jon K Reel, Celia A Whitesitt
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Patent number: 6057446Abstract: A compound having the formula: ##STR1## wherein X' is nitrogen or carbon bonded to a substituent species characterized as having a sigma m value greater than 0, less than 0 or 0; X is nitrogen or carbon bonded to a substituent species characterized as having a sigma m value greater than 0, less than 0, but not equal to 0; A, A' and A" are individually substituent species characterized as having a sigma m value greater than 0, less than 0 or 0; Z' is a substituent other than hydrogen; j is an integer from 0 to 5; and the wavy line in the structure indicates that the compound can exist in the form of an enantiomer or a diasteromer; Z" is hydrogen or a substituent other than hydrogen; Y is C.dbd.O, C(OH)R' or C--A, where R' is hydrogen or lower alkyl.Type: GrantFiled: April 2, 1998Date of Patent: May 2, 2000Inventors: Peter Anthony Crooks, Haeil Park, Balwinder Singh Bhatti, William Scott Caldwell, Gary Maurice Dull
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Patent number: 5990104Abstract: Polycyclic alkaloids of formula (I), wherein R.sub.1 is H, C.sub.1-6 alkyl, or C.sub.6-12 aryl optionally substituted with polar groups; R.sub.2 and R.sub.3 are independently H, OH, C.sub.1-6 alkyl, --C(NH)--NH.sub.2, a positively charged group, or C.sub.7-13 aralkyl optionally substituted with NH.sub.2, OH, C.sub.1-6 alkyl, or halogen; or R.sub.2 and R.sub.3 together form a 5 to 6 member ring optionally incorporating a heteroatom; R.sub.4 is H, C.sub.1-6 alkyl, OR.sub.6, SR.sub.6, or N(R.sub.6).sub.2, wherein each R.sub.6 is independently H, C.sub.1-3 alkyl; X ix O, S, SO, SO.sub.2, or N--R.sub.5, wherein each R.sub.5 is independently H, C.sub.1-6 alkyl, or C.sub.7-13 aralkyl optionally interrupted with one or more heteroatom; n is an integer from 0 to 2; and m is an integer from 0 to 3. These compounds act as antagonists at the ionotropic NMDA (N-methyl-(D)-aspartic acid) receptor.Type: GrantFiled: March 25, 1998Date of Patent: November 23, 1999Assignee: Biochem Pharma, Inc.Inventors: John Dimaio, Dilip M. Dixit
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Patent number: 5945535Abstract: The present invention relates to a new process for preparing norbenzomorphan, the central intermediate step in the preparation of pharmaceutically useful benzomorphan derivatives of general formula 1 ##STR1## especially (-)-(1R,5S,2"R)-3'-hydroxy-2-(2-methoxypropyl)-5,9,9-trimethyl-6,7-benzomo rphan or ?(-)-(2R,6S,2'R)-3-(2-methoxypropyl)-6,11,11-trimethyl-1,2,3,4,5,6 -hexahydro-2,6-methano-benzo?.alpha.!oxacin-9-ol! (BIII 277).Type: GrantFiled: May 1, 1998Date of Patent: August 31, 1999Assignee: Boehringer Ingelheim KGInventors: Matthias Grauert, Herbert Merz, Hanfried Baltes
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Patent number: 5929084Abstract: The present invention relates to novel huperzine A derivatives of formula (II), wherein Y is ##STR1## or R" and Y together form .dbd.CH; R is (C.sub.1 -C.sub.5) alkyl, ##STR2## wherein n is 0 or 1, X is H, (C.sub.1 -C.sub.5) alkyl; (C.sub.1 -C.sub.5) alkyloxy; nitro, halogen, carboxy, alkyloxycarbonyl, hydroxymethyl, hydroxy, amino substituted by bis-(C.sub.1 -C.sub.5) alkyl; --(CH.sub.2).sub.m COOZ, wherein m=0-5, Z is H or (C.sub.1 -C.sub.5) alkyl; --CH.dbd.CH--G, wherein G is phenyl, furanyl, carboxy, alkyloxycarbonyl; and dihydro- or tetrahydro-pyridyl substituted by (C.sub.1 -C.sub.5) alkyl at the nitrogen atom; R' is H, (C.sub.1 -C.sub.5) alkyl, pyridoyl, benzoyl substituted by (C.sub.1 -C.sub.5) alkyloxy; R" is H or (C.sub.1 -C.sub.5) alkyl; processes for their use as acetylcholinesterase inhibitor.Type: GrantFiled: June 27, 1997Date of Patent: July 27, 1999Assignee: Shangahi Institute of Materia Medica Chinese Academy of SciencesInventors: Dayuan Zhu, Xican Tang, Jinlai Lin, Cheng Zhu, Jingkang Shen, Guansong Wu, Shanhao Jiang, Takuji Yamaguchi, Kazuhiro Tanaka, Takeshi Wakamatsu, Hiroaki Nishimura
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Patent number: 5783584Abstract: The present invention provides cholinesterase inhibitors of general formula (I): ##STR1## wherein R is H or (C.sub.1 -C.sub.4)alkyl, Y is a linking group and Z is an alkyl or aryl group, including heteroaryl groups, and the pharmaceutically acceptable salts thereof.Type: GrantFiled: December 11, 1995Date of Patent: July 21, 1998Assignee: Mayo Foundation for Medical Education and ResearchInventors: Yuan-Ping Pang, Stephen Brimijoin
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Patent number: 5731318Abstract: Novel benzomorphan derivatives of the formula ##STR1## wherein R.sup.1 -R.sup.8 are as defined herein. The benzomorphan derivatives are useful for treating cerebral ischaemia of various origins, epilepsy and neurodegenerative diseases.Type: GrantFiled: August 1, 1996Date of Patent: March 24, 1998Assignee: Boehringer Ingelheim KGInventors: Adrian Carter, Helmut Ensinger, Matthias Grauert, Franz Josef Kuhn, Herbert Merz, Enzio Mueller, Werner Stransky, Ilse Streller
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Patent number: 5717098Abstract: A process for the preparation of a .gamma.-lactone of the formula ##STR1## which can be used to produce a single enantiomer of aminoazanoradamantane which is coupled to aromatic acid moieties to produce compounds useful as 5-HT agonists or antagonists.Type: GrantFiled: July 22, 1996Date of Patent: February 10, 1998Assignee: G. D. Searle & Co.Inventors: Daniel Paul Becker, Daniel Lee Flynn, Alan Edward Moormann, Clara Ines Villamil
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Patent number: 5663344Abstract: The present invention relates to a method for the synthesis of certain bridged fused ring pyridines. Such bridged fused ring pyridines can be converted to huperzine A and analogs of huperzine A. The present invention also covers such bridged fused ring pyridines, compounds utilized for the preparation of the bridged fused ring pyridines and analogs of huperzine A. The compounds are capable of inhibiting cholinesterase enzymes and, therefore, are useful as pharmaceutical agents for treatment of disorders involving cholinesterase enzymes. Examples of such disorders include myasthenia gravis, Alzheimer's dementia and the improvement of senile memory loss.Type: GrantFiled: July 22, 1994Date of Patent: September 2, 1997Assignee: Mayo Foundation for Medical Education and ResearchInventors: Alan Paul Kozikowski, Yan Xia
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Patent number: 5650406Abstract: A compound represented by general formula (1) or an innocuous salt thereof, a process for producing the same, and a schizophrenia remedy containing the same as the active ingredient (wherein the nitrogeneous ring B represents 3-azabicyclo [3.2.2] nonan-3-yl or 4-azatricyclo [4.3.1.1.sup.3.8 ] undecan-4-yl; and R represents hydrogen, lower alkyl, lower alkoxy, hydroxy or halogen). The above compound and salt have a high affinity for sigma-binding sites and are useful as an antischizophrenic drug.Type: GrantFiled: October 8, 1996Date of Patent: July 22, 1997Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Nobuyuki Takahashi, Daisuke Mochizuki
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Patent number: 5607941Abstract: Novel benzomorphan derivatives of the formula ##STR1## wherein R.sup.1 -R.sup.8 are as defined herein. The benzomorphan derivatives are useful for treating cerebral ischaemia of various origins, epilepsy and neurodegenerative diseases.Type: GrantFiled: June 5, 1995Date of Patent: March 4, 1997Assignee: Boehringer Ingelheim KGInventors: Herbert Merz, Enzio Mueller, Werner Stransky, Ilse Streller
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Patent number: 5594002Type: GrantFiled: October 25, 1994Date of Patent: January 14, 1997Assignee: Pfizer IncInventor: Yuhpyng L. Chen
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Patent number: 5587481Abstract: Methods for preparing (S)-N-tert-butyl-1,2,3,4-tetrahydro-3-isoquinoline-carboxamide ("tic-c"), and converting tic-c to (S)-decahydroisoquinoline-3-carboxylic acid t-butylamide ("tic-d") are disclosed. The initial step in the formation of tic-c involves the phosgenation of a substituted tetrahydroisoquinoline to form an N-carboxy anhydride. Tic-d is used as an intermediate in the synthesis of known compounds having pharmaceutical activity.Type: GrantFiled: February 20, 1996Date of Patent: December 24, 1996Assignee: The Monsanto CompanyInventors: David R. Allen, Scott Jenkins, Loraine Klein, Robert Erickson, Diane Froen
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Patent number: 5567818Abstract: This invention relates to processes for preparing 2-(1-azabicyclo[2.2.2]oct-3-yl)-2,3,3a,4,5,6-tetrahydro-1H-benz[de]isoquin olin-1-one, particularly 2-(1-azabicyclo[2.2.2]oct-3S-yl)-2, 3,3aS,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one, and to intermediates useful in such processes.Type: GrantFiled: July 8, 1994Date of Patent: October 22, 1996Assignee: Syntex (U.S.A.) Inc.Inventors: Bruce A. Kowalczyk, Charles A. Dvorak
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Patent number: 5462960Abstract: The present invention relates to novel pyrazole-3-carboxamide derivatives of the formula ##STR1## in which the substituents are as defined in the specification. The present invention further relates to a process for the preparation of these novel derivatives and to the pharmaceutical compositions in which they are present.Type: GrantFiled: December 16, 1994Date of Patent: October 31, 1995Assignee: SanofiInventors: Francis Barth, Pierre Casellas, Christian Congy, Serge Martinez, Murielle Rinaldi
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Patent number: 5420136Abstract: A class of predominantly hydrophobic non-azo N-substituted 1,8-naphthalimide compounds, each bearing, at its 3-position, a nucleofuge and, at its 4-position, a heteroatomic electron-releasing group. The heteroatomic electron-releasing group is being characterized as having a heteroatom directly linked to the 4-position of the ring, and having at least one hydrogen directly attached to the heteroatom. Upon activation by an activating agent in an environment independent of the presence or absence of oxygen, these compounds generate activated species. The activated species initiate chemical changes in lipid bilayer membranes of viruses and other target cells. These changes can eradicate viruses and other target cells. The activated species can also cause structural changes in lipid and any associated proteins and polypeptides at a level beneath the surface of the membrane, leading to polymerization and crosslinking.Type: GrantFiled: August 9, 1993Date of Patent: May 30, 1995Assignee: MicroBioMed CorporationInventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
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Patent number: 5399562Abstract: This invention relates to compounds of the formula: ##STR1## which are useful as 5-HT.sub.4 agonists or antagonists and 5-HT.sub.3 antagonists.Type: GrantFiled: February 4, 1994Date of Patent: March 21, 1995Assignee: G. D. Searle & Co.Inventors: Daniel P. Becker, Daniel L. Flynn, Clara I. Villamil
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Patent number: 5387590Abstract: Compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X, m, n, o, p, q and r are as defined below. The compounds are memory enhancing cholinesterase inhibitors useful in enhancing memory, novel intermediates used in their synthesis, and analgesic agents.Type: GrantFiled: February 28, 1992Date of Patent: February 7, 1995Assignee: Pfizer Inc.Inventor: Yuhpyng L. Chen
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Patent number: 5354758Abstract: Compounds of the formula I ##STR1## are disclosed. In this formula, R is a member selected from the group consisting of --CR.sub.1 R.sub.2 R.sub.3, hydroxy, an alkoxy group having 1 to 4 carbon atoms and --NR.sub.4 R.sub.5, in which at most one of R.sub.1, R.sub.2 and R.sub.3 is hydrogen and the remainder are each independently selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, a cycloalkylalkyl having 4 to 9 carbon atoms and a 3 to 6 membered cyclic ether; R.sub.4 and R.sub.5 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms; R.sub.6 and R.sub.7 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms; and R.sub.8 is hydrogen, an alkyl group having 1 to 4 carbon atoms, hydroxy, an alkoxy group having 1 to 4 carbon atoms or halogen. Salts of these compounds are also disclosed.Type: GrantFiled: December 16, 1992Date of Patent: October 11, 1994Assignee: Japan Tobacco Inc.Inventors: John A. Lawson, Itsuo Uchida
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Patent number: 5240935Abstract: Novel substituted 2-azabicyclo[2.2.2]octane derivatives, pharmaceutical compositions containing them, methods for treating central nervous system disorders utilizing them, and processes for synthesizing them.Type: GrantFiled: November 20, 1992Date of Patent: August 31, 1993Assignee: Sterling Winthrop Inc.Inventors: Diane L. DeHaven-Hudkins, John P. Mallamo, William F. Michne, Martha R. Heimann
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Patent number: 5235045Abstract: A class of predominantly hydrophobic non-azo N-substituted 1,8-naphthalimide compounds, each bearing, at its 3-position, a nucleofuge and, at its 4-position, a heteroatomic electron-releasing group. The heteroatomic electron-releasing group is being characterized as having a heteroatom directly linked to the 4-position of the ring, and having at least one hydrogen directly attached to the heteroatom. Upon activation by an activating agent in an environment independent of the presence or absence of oxygen, these compounds generate activated species. The activated species initiate chemical changes in lipid bilayer membranes of viruses and other target cells. These changes can eradicate viruses and other target cells. The activated species can also cause structural changes in lipid and any associated proteins and polypeptides at a level beneath the surface of the membrane, leading to polymerization and crosslinking.Type: GrantFiled: March 19, 1992Date of Patent: August 10, 1993Assignee: MicroBioMed CorporationInventors: David E. Lewis, Ronald E. Utecht, Millard M. Judy, J. Lester Matthews
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Patent number: 5177082Abstract: The invention relates to compounds of the formulas ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or lower alkyl, and the dotted ( . . . ) line is an optional double bond, and their pharmaceutically acceptable acid addition salts. The compounds of formulas I, II and III possess marked anticholinesterase activity and are useful as analeptic agents and as agents for the treatment of senile dementia and myasthenia gravis.Type: GrantFiled: October 18, 1990Date of Patent: January 5, 1993Inventors: Chao-mei Yu, Xi-can Tang, Jia-sen Liu, Yan-yi Han
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Patent number: 5145965Abstract: Novel 2,6-methanopyrrolo-3-benzazocines, intermediates, processes for the preparation thereof, and methods for alleviating pain utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: March 11, 1991Date of Patent: September 8, 1992Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Richard C. Allen, David G. Wettlaufer
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Patent number: 5106979Abstract: The present invention relates to a method for the synthesis of certain bridged fused ring pyridines. Such bridged fused ring pyridines can be converted to huperzine A and analogs of huperzine A. The present invention also covers such bridged fused ring pyridines, compounds utilized for the preparation of the bridged fused ring pyridines and analogs of huperzine A.Type: GrantFiled: March 23, 1990Date of Patent: April 21, 1992Assignee: University of PittsburghInventors: Alan P. Kozikowski, Yan Xia
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Patent number: 5104880Abstract: An acetylcholinesterase inhibitor is provided of the general formula (I): ##STR1## wherein R.sub.1 is H, (C.sub.1 -C.sub.8)alkyl or halo; R.sub.2 is H or (C.sub.1 -C.sub.8)alkyl; R.sub.3 and R.sub.4 are individually H, (C.sub.1 -C.sub.8)alkyl, NO.sub.2, hydroxy or halo; R.sub.5 and R.sub.6 are individually H, (C.sub.1 -C.sub.8)akyl, aryl or aralkyl; R.sub.7 is H, halo or (C.sub.1 -C.sub.8)alkyl, R.sub.8 is halo or (C.sub.1 -C.sub.8)alkyl; R.sub.9 is absent or is H; and the bonds represented by--are individually absent or, together with the adjacent bond, form the unit C.dbd.C, with the proviso that if both of the bonds represented by--are present, R.sub.3 and R.sub.4 cannot both be H unless R.sub.7 or R.sub.8 is halo; and the pharmaceutically acceptable salts thereof.Type: GrantFiled: May 1, 1991Date of Patent: April 14, 1992Assignee: Mayo Foundation for Medical Education and ResearchInventor: Alan P. Kozikowski
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Patent number: 4985430Abstract: There are disclosed a 9-acylamino-tetrahydroacridine derivative represented by the following formula (I): ##STR1## wherein R ##STR2## are as defined in the specification, its optical antipode or pharmaceutically acceptable acid addition salt thereof and a memory enhancing agent containing the same as an active ingredient.Type: GrantFiled: December 2, 1988Date of Patent: January 15, 1991Assignee: Mitsubishi Kasei CorporationInventors: Shuji Morita, Ken-Ichi Saito, Kunihiro Ninomiya, Akihiro Tobe, Issei Nitta, Mamoru Sugano
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Patent number: 4929731Abstract: The present invention relates to a method for the synthesis of certain bridged fused ring pyridines. Such bridged fused ring pyridines can be converted to huperzine A and analogs of huperzine A. The present invention also covers such bridged fused ring pyridines, compounds utilized for the preparation of the bridged fused ring pyridines and analogs of huperzine A.Type: GrantFiled: February 21, 1989Date of Patent: May 29, 1990Assignee: University of PittsburghInventors: Alan P. Kozikowski, Yan Xia
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Patent number: 4871842Abstract: Novel compounds of the formula: ##STR1## [wherein A is an .alpha.-amino acid residue; B is a group represented by the formula: ##STR2## (wherein R.sup.4 is hydrogen, lower alkyl, aralkyl or amino-lower alkyl), whereby the linkage between the symbols A and B designates a peptide bond and the group R.sup.4 in B may be linked with A; R.sup.1 is hydrogen, lower alkyl or aralkyl; R.sup.2 is hydrogen, lower alkyl, aralkyl or acyl; X is alkylene] and salts thereof possess, for example, inhibitory activity on angiotensin converting enzyme, and are useful as an agent for diagnosis, prevention or treatment of hypertension as well as circulatory diseases such as cardiopathy and cerebral apoplexy.Type: GrantFiled: July 14, 1988Date of Patent: October 3, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Hirosada Sugihara, Kohei Nishikawa, Katsumi Ito
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Patent number: 4777254Abstract: Polycyclic 1,3-dione imides N-alkylated with variously N-substituted alkyl- or cycloalkyl amines afford histamine H.sub.1 -receptor antagonists of the formula ##STR1## wherein R is polycyclic alkyl moiety;R.sup.1 is hydrogen or alkyl;R.sup.4 is an aromatic amine or a cycloalkyl amine containing N-substitution;R.sup.7 and R.sup.8 are hydrogen, alkyl or form a spiro cycloalkyl group.Type: GrantFiled: December 2, 1986Date of Patent: October 11, 1988Assignee: American Home Products Corp.Inventors: Magid A. Abou-Gharbia, Susan T. Nielsen
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Patent number: 4767718Abstract: Fluorescent reagents useful as opioid receptor probes. Opioids labeled at the 3 position with fluorescers are useful in various in vivo and in vitro methods for the detection and quantification of receptor sites in tissue cells and subcellular particles.Type: GrantFiled: June 18, 1984Date of Patent: August 30, 1988Assignee: Southern Illinois University FoundationInventor: Vera K. Meyers
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Patent number: 4552881Abstract: Novel substituted and bridged pyridines useful as calcium channel blockers, pharmaceutical compositions thereof and methods of treatment are disclosed.Type: GrantFiled: August 1, 1984Date of Patent: November 12, 1985Assignee: Merck & Co., Inc.Inventor: David A. Claremon
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Patent number: 4542215Abstract: A method for preparing 8-acylthio-1,2,3,4,5,6-hexahydro-2,6-methano-3,6(e),11(a)-trimethyl-3-benz azocines represented by general formula (I) below ##STR1## wherein R represents an alkyl group, a phenyl group or a heterocyclic group, which comprises reacting 1,2,3,4,5,6-hexahydro-2,6-methano-3,6(e),11(a)-trimethyl-3-benzazocine represented by the formula (II) below ##STR2## or its salt with chlorosulfonic acid, heating the reaction product in the presence of a reducing agent, and reacting the reaction mixture with an acyl halide represented by the general formula (III)RCOX (III)wherein R has the same meaning as defined above and X represents a halogen atom is disclosed.Type: GrantFiled: May 19, 1983Date of Patent: September 17, 1985Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Mikio Hori, Hajime Fujimura
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Patent number: 4535085Abstract: A perfluorotricyclic amine compound which is usable as an oxygen carrier in an artificial blood, represented by the general formula ##STR1## wherein R denotes a perfluoroalkyl group having 1-4 carbon atoms; the ring A denotes a five- or six-membered ring, the ring B denotes a five-, six- or seven-membered ring, the ring C denotes a five- or six-membered ring any one of the rings A, B and C optionary being substituted by one or more lower perfluoroalkyl group in addition to the above-mentioned substituent R; and further f, g, h, i, j and k denote integers appropriately selected to construct the above-mentioned size of rings A, B, and C; is prepared by reacting the corresponding perhydrotricyclic amine with fluorine.Type: GrantFiled: March 29, 1983Date of Patent: August 13, 1985Assignee: The Green Cross CorporationInventors: Kazumasa Yokoyama, Chikara Fukaya, Yoshio Tsuda, Taizo Ono, Yoshio Arakawa, Yoshihisa Inoue, Youichiro Naito, Tadakazu Suyama
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Patent number: 4473576Abstract: 9,9-Dimethyl-6,7-benzomorphan derivatives having an oxygen-containing substituent on the nitrogen atom, optionally an alkyl or phenyl 5-substituent and optionally a hydroxy, alkoxy or acyloxy 2'-substituent have analgetic and/or morphine-antagonist properties.Type: GrantFiled: October 31, 1983Date of Patent: September 25, 1984Assignee: ACF Chemiefarma NVInventors: Antony M. Akkerman, Hermanus C. C. K. van Bakel
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Patent number: 4425353Abstract: 6,7-Benzomorphan derivatives of formula I, ##STR1## wherein R.sub.1 is hydrogen; optionally hydroxy- and/or alkoxy-substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl; alkenyloxyalkyl, aralkyl, arylhydroxyalkyl, aralkenyl or tetrahydrofurylalkyl; or optionally alkyl-substituted furylalkyl or isoxazolylalkyl, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, aralkyl, hydroxyalkyl of alkoxyalkyl and R.sub.4 is hydrogen, hydroxy, alkoxy or alkenyloxy, hydroxy groups in said compounds being each optionally acylated, having analgesic and luteinising hormone secretion inhibiting properties.Type: GrantFiled: July 13, 1981Date of Patent: January 10, 1984Assignee: ACF Chemiefarma NVInventors: Antony M. Akkerman, Hermanus C. C. K. van Bakel, Roelof C. K. Smit
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Patent number: 4363809Abstract: Method of inhibiting luteinising hormone secretion in a subject, said method comprising administering an optionally 5-alkyl- or -phenyl- and/or 2'-hydroxy-, -alkoxy- or -acyloxy-substituted 9,9-dimethyl-6,7-benzomorphan derivative having an oxygen containing substituent at the N-atom.Type: GrantFiled: July 13, 1981Date of Patent: December 14, 1982Assignee: Sandoz Ltd.Inventors: Magda Marko, Hendricus B. A. Welle
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Patent number: 4335243Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.Type: GrantFiled: March 12, 1981Date of Patent: June 15, 1982Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4296238Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.Type: GrantFiled: May 7, 1980Date of Patent: October 20, 1981Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4294840Abstract: The method of producing anesthesia in a mammal comprising administering intravenously to the mammal an anesthetically effective amount of a pharmaceutically acceptable salt of racemic ketazocine or levo-ketazocine with or without diazepam premedication and the method of producing analgesia in a human which comprises administering intramuscularly to the human an anesthetically effective amount of at least 1 mg. of a pharmaceutically acceptable salt of racemic ketazocine or levo-ketazocine are disclosed.Type: GrantFiled: August 31, 1979Date of Patent: October 13, 1981Assignee: Sterling Drug Inc.Inventor: Alfred E. Farah
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Patent number: 4293556Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is methyl, ethyl or propyl;R.sub.2 is hydrogen, methyl or ethyl; andR.sub.3 is ##STR2## where R.sub.4 is hydrogen or methyl,R.sub.5 is methyl, ethyl or propyl, andn is 1 or 2,and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as analgesics.Type: GrantFiled: May 28, 1980Date of Patent: October 6, 1981Assignee: Boehringer Ingelheim GmbHInventors: Herbert Merz, Klaus Stockhaus
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Patent number: 4288444Abstract: The invention is concerned with certain new 6,7-benzomorphan derivatives having pharmacological, in particular analgesic and/or morphine-antagonistic properties, of the formula ##STR1## wherein R.sup.1 is a substituted or unsubstituted phenyl or heteroaryl group; R.sup.2 is a hydrogen or halogen atom, or a hydroxy, alkoxy or acyloxy group; R.sup.3 is an alkyl or alkenyl group; R.sup.4 is a hydrogen atom or a hydroxy, alkoxy or acyloxy group; and R.sup.5 is an alkyl group or, when R.sup.2 is hydrogen in a trans-position to R.sup.3, R.sup.5 is a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, cycloalkenylalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, or a substituted or unsubstituted phenylalkyl, heteroarylalkyl or heterocycloalkylalkyl group; optical isomers and pharmaceutically acceptable salts thereof.The preferred compound is the .alpha.-isomer of 2,5-dimethyl-2'-hydroxy-9-phenyl-6,7-benzomorphan, in particular its (+)-enantiomer.Type: GrantFiled: April 25, 1980Date of Patent: September 8, 1981Assignee: ACF Chemiefarma N.V.Inventors: Antony M. Akkerman, Hermanus C. C. K. van Bakel, Henriette G. Van Breevoort-Uurbanus
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Patent number: 4268673Abstract: The invention is concerned with certain novel 6,7-benzomorphan derivatives having analgesic and/or morphine-antagonistic properties of the formula ##STR1## wherein each R is a lower alkyl group; R.sub.1 is a hydrogen atom, or an alkyl, haloalkyl, alkenyl, haloalkenyl, alkinyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkenylalkyl, cycloalkylidenealkyl, aralkyl, heteroarylalkyl or heterocycloalkylalkyl group; R.sub.2 is a hydrogen atom or a hydroxy, alkoxy, alkoxyalkoxy or acyloxy group.Such 6,7-benzomorphans may be in the form of their optically active enantiomers and/or their therapeutically acceptable salts. Methods for producing such 6,7-benzomorphan derivatives, and novel intermediates useful for such production are also disclosed and form part of the invention.Type: GrantFiled: July 28, 1978Date of Patent: May 19, 1981Assignee: ACF Chemiefarma N.V.Inventors: Antony M. Akkerman, Geertruida C. van Leeuwen
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Patent number: 4261990Abstract: N-(diphenylmethoxy-mono- or bicyclic-alkyleneiminoalkyl)-dicarboximides, e.g. those of the formula ##STR1## A=aliphatic or cycloaliphatic radical R,R'=H, alkyl, halogen or CF.sub.3R"=H or both are ethyleneq=2-4and salts thereof are antiallergics and antiasthmatics.Type: GrantFiled: March 9, 1979Date of Patent: April 14, 1981Assignee: Ciba-Geigy CorporationInventor: Robert M. Bowman