Plural Ring Nitrogens In The Tricyclo Ring System Patents (Class 546/81)
  • Patent number: 6071947
    Abstract: The present invention relates to substituted (1H-indol-2-yl)-5[(2H-pyrrol-2-ylidene) methyl]-1H-pyrrole compounds and their use as immunomodulating agents, to the preparation of the compounds and to pharmaceutical compositions comprising them.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: June 6, 2000
    Assignee: Pharmacia & Upjohn S.p.A.
    Inventors: Roberto D'Alessio, Marcellino Tibolla, Alberto Bargiotti, Anna Maria Isetta, Mario Ferrari, Francesco Colotta
  • Patent number: 6017924
    Abstract: Non-steroidal compounds that are high affinity, high selectivity modulators for androgen receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring androgen receptor agonist, partial agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the androgen receptor modulator compounds.
    Type: Grant
    Filed: August 12, 1999
    Date of Patent: January 25, 2000
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: James P Edwards, Robert Higuchi, Todd K Jones, Lawrence G Hamann
  • Patent number: 6017926
    Abstract: The present invention relates to compounds and derivatives thereof, their synthesis, and their use as integrin receptor antagonists. More particularly, the compounds of the present invention are antagonists of the integrin receptors .alpha.v.beta.3, .alpha.v.beta.5 and/or .alpha.v.beta.6 and are useful for inhibiting bone resorption, treating and preventing osteoporosis, and inhibiting vascular restenosis, diabetic retinopathy, macular degeneration, angiogenesis, atherosclerosis, inflammation, wound healing, viral disease, and tumor growth and metastasis.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: January 25, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Ben C. Askew, Paul J. Coleman, Mark E. Duggan, Wasyl Halczenko, John H. Hutchinson, Robert S. Meissner, Michael A. Patane, Jiabing Wang
  • Patent number: 6008215
    Abstract: Compounds of formula (I) in which R1, R2, R3 and R4 have the meanings indicated in the description, are novel active bronchial therapeutics
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: December 28, 1999
    Assignee: Byk Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Dieter Flockerzi
  • Patent number: 5998619
    Abstract: A process for preparing 1H-imidazo[4,5-c]quinolin-4-amines is disclosed. The process involves reacting a 6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline with triphenylphosphine and hydrolyzing the product thereof.
    Type: Grant
    Filed: April 16, 1998
    Date of Patent: December 7, 1999
    Assignee: 3M Innovative Properties Company
    Inventors: John F. Gerster, Kyle J. Lindstrom
  • Patent number: 5998594
    Abstract: A chromogenic receptor comprises a self-assembled chromogenic compound having at least one intrinsic binding site. The chromogenic compound is characterized by the property of producing a reversible color change responsive to binding a target substrate to the receptor. The chromogenic compound has a transition metal ion and at least one ligand bound to the transition metal ion. The ligand is selected from the group consisting of substituted phenanthroline, substituted 2,2'-bipyridine and substituted 2,2':6',2"-terpyridine. The transition metal is selected from the group consisting of Cu(I), Cu(II), Ag(I), Ni(II), Fe(II), Fe(III), Ru(II), Co(III), and Os(II). Self-assembly can be effected in the presence of Cu(I) to form receptors for dicarboxylic acids, carbohydrate, amino acids, steroids and pyrophosphates. The receptors are characterized by the formation of a 2:1 complex of the target substrate with the receptor producing a visible color change from orange to red and a measurable change in its luminescence.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: December 7, 1999
    Assignee: University of Pittsburgh of the Commonwealth System of Higher Education
    Inventors: M. Scott Goodman, Andrew D. Hamilton
  • Patent number: 5994365
    Abstract: Novel diazaanthracenes of formula wherein the dotted line in the central ring indicates that either the central ring is aromatically unsaturated, and in this case either R.sup.3 or H is absent from the 10-position and either R.sup.4 or H is absent from the 5-position, or the central ring is saturated and R.sup.3 and H and R.sup.4 and H are present, and the corresponding 5,10-diones, N-oxides, N-halides, N-amine, salts, dimers, Diels-Alder adducts, carbene adducts and complexes with transition metal compounds display valuable antibacterial, anticancer and antifungal properties. The compounds of formulae (I) and (II) in which R.sup.1 and R.sup.2 are both methyl groups can be obtained by subjecting 3,5-lutidine to the effect of a strong reducing agent, for example molten sodium.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: November 30, 1999
    Assignee: Diazans Limited
    Inventors: Michael John Zaworotko, Subramanian Sethuraman Iyer
  • Patent number: 5994366
    Abstract: The present invention relates to certain tetrahydroimidazo[2,1-a]isoquinoline derivatives according to formula I wherein X is a group (A) or (B) ##STR1## R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent one or more substituents selected from hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.4-6 cycloalkenyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl and halogen;R.sup.4, R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, are each selected from hydrogen, C.sub.1-6 alkoxyC.sub.1-6 alkyl, C.sub.4-6 cycloalkenyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl and C.sub.1-6 alkyl; n is 1 or 2; or a pharmaceutically acceptable salt or solvate thereof, to processes for their preparation, to pharmaceutical formulations containing them and to their use in medical therapy, particularly in the treatment of depression.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: November 30, 1999
    Assignee: Akzo Nobel NV
    Inventors: Dirk Leysen, Gerardus Stephanus Franciscus Ruigt
  • Patent number: 5968252
    Abstract: Compounds of formula ##STR1## wherein R and R' are each independently of the other hydrogen, C.sub.1 -C.sub.18 alkyl, COR.sub.1, COR.sub.2 or COOR.sub.1,X and X' are each independently of the other hydrogen, halogen, OH, NH.sub.2, COOH, C.sub.1 -C.sub.18 -alkyl, isocyclic or heterocyclic aromatic radicals, OR.sub.3, OCOR.sub.3, OCOR.sub.4, OCOR.sub.3, NHR.sub.3, N(R.sub.3).sub.2, NHCOR.sub.3, NHCOR.sub.4 or NHCOOR.sub.3,Y and Y' are each independently of the other hydrogen, halogen, OH, NH.sub.2, nitro, cyano, C.sub.1 -C.sub.18 alkyl, isocyclic or heterocyclic aromatic radicals, COR.sub.5, COR.sub.6, COOR.sub.5, COOR.sub.6, CONH.sub.2, SO.sub.2 R.sub.5, SO.sub.2 R.sub.6, SO.sub.2 NH.sub.2, SO.sub.3 H, PO(OR.sub.5).sub.2 or PO(OH).sub.2, andZ and Z' are each independently of the other hydrogen, halogen, OH, NH.sub.2, COOH, cyano, C.sub.1 -C.sub.18 alkyl, isocyclic or heterocyclic aromatic radicals, OR.sub.7, OR.sub.8, OCOR.sub.7, OCOR.sub.8, OCOOR.sub.7, NHR.sub.7, N(R.sub.7).sub.2, NHR.sub.8, CONH.sub.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: October 19, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Robert Moretti, Gary Wooden
  • Patent number: 5958970
    Abstract: This invention provides cancer-active tricyclic and tetracyclic oxypyrones and a method of synthesizing these compounds. Preferred compounds have aryl groups at the 3-position of the oxypyrone ring. The tricyclic oxyprone synthetic method is a simple condensation reaction of pyrones with cyclohexenecarboxaldehydes, providing high yields and using few steps. The tetracyclic oxypyrone synthetic method is a simple condensation reaction of carvones with pyrones.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: September 28, 1999
    Assignee: Kansas State University Research Foundation
    Inventors: Duy H. Hua, Jean-Pierre Perchellet
  • Patent number: 5929085
    Abstract: There are provided novel compounds of formula (I) ##STR1## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as defined in the specification and optical isomers and racemates thereof and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.
    Type: Grant
    Filed: January 22, 1997
    Date of Patent: July 27, 1999
    Assignee: Astra Aktiebolag
    Inventors: James MacDonald, James Matz, William Shakespeare
  • Patent number: 5914402
    Abstract: The present invention relates to a process for preparing 1-aryl-4-oxopyrrolo?3,2-c!quinoline derivatives through reaction of 4-oxofuro?3,2-c! quinoline compounds with aniline compounds under mild conditions in a single step, wherein 1-aryl-4-oxopyrrolo?3,2-c!quinoline derivatives having various substituents may be prepared in high yield, so that the 1-aryl-4-oxopyrrolo?3,2-c!quinoline derivatives may be utilized as an intermediate for producing a reversible inhibitor of gastric acid secretion.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: June 22, 1999
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Joong Kwon Choi, Sung Soo Kim, Eul Kyun Yum, Sung Yun Cho, Seung Kyu Kang
  • Patent number: 5861411
    Abstract: A novel 4-acylaminopyridine derivative represented by the following formula (I) is disclosed. ##STR1## The 4-acylaminopyridine derivative of the present invention is useful as a medicine for treating disturbances of memory such as senile dementia and Alzheimer's disease, since it has an action of directly activating malfunctioned cholinergic neuron.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: January 19, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kunihiro Ninomiya, deceased, Ken-ichi Saito, Mamoru Sugano, Akihiro Tobe, Yasuhiro Morinaka, Tomoko Bessho, Haruko Harada
  • Patent number: 5859006
    Abstract: A compound of formula (I) ##STR1## and salts and solvates thereof, in which: R.sup.0 represents hydrogen, halogen or C.sub.1-6 alkyl;R.sup.1 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, haloC.sub.1-6 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkylC.sub.1-3 alkyl, arylC.sub.1-3 alkyl or heteroarylC.sub.1-3 alkyl; R.sup.2 represents an optionally substituted monocyclic aromatic ring selected from benzene, thiophene, furan and pyridine or an optionally substituted bicyclic ring ##STR2## attached to the rest of the molecule via one of the benzene ring carbon atoms and wherein the fused ring A is a 5- or 6-membered ring which may be saturated or partially or fully unsaturated and comprises carbon atoms and optionally one or two heteroatoms selected from oxygen, sulphur and nitrogen; andR.sup.3 represents hydrogen or C.sub.1-3 alkyl, or R.sup.1 and R.sup.3 together represent a 3- or 4-membered alkyl or alkenyl chain.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: January 12, 1999
    Assignee: ICOS Corporation
    Inventor: Alain Claude-Marie Daugan
  • Patent number: 5856334
    Abstract: Specified imidazoquinoline derivatives represented by the formula (I): ##STR1## where Q represents an optionally substituted phenyl, pyridyl or furyl group; Y represents either a hydrogen atom or, when taken together with Z, an oxygen atom and a methylene group; Z represents a hydrogen atom, a hydroxymethyl group, a carboxymethyl group, a 2-oxo-1-pyrrolidinyl group or the following formula (III):--A--R.sup.2 (III)(where A represents an oxygen atom, a sulfur atom or the group --NH--);or salts of such derivatives inhibit the increase of eosinophils and are useful as agents for preventing and/or treating diseases that manifest the increase of eosinophils.
    Type: Grant
    Filed: January 28, 1997
    Date of Patent: January 5, 1999
    Assignee: Mochida Pharmaceutical Co., Ltd.
    Inventors: Hidenori Mochizuki, Kazuo Kato, Ichiro Yamamoto, Kiyoshi Mizuguchi
  • Patent number: 5741908
    Abstract: A process for preparing 1H-imidazo?4,5-c!quinolin-4-amines is disclosed. The process involves reacting a 6H-imidazo?4,5-c!tetrazolo?1,5-a!quinoline with triphenylphosphine and hydrolyzing the product thereof.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: April 21, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: John F. Gerster, Kyle J. Lindstrom
  • Patent number: 5723413
    Abstract: Naphthyridines of the formula I ##STR1## where R.sup.1 is an unsubstituted or substituted phenyl ring or heteroaromatic radical and R.sup.2 -R.sup.6 are hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, alkoxyalkyl, aminoalkyl, unsubstituted or substituted phenyl, benzyl, unsubstituted or substituted heteroaryl linked via a carbon, cyano, nitro, carboxyl, sulfonylmethyl, alkoxycarbonyl, carbamoyl, alkylcarbamoyl, dialkylcarbamoyl, alkanoyl, benzoyl, it being possible for R.sup.4 and R.sup.5 or R.sup.5 and R.sup.6 to be bonded by a methylene chain or by a CH.dbd.CH--CH.dbd.CH group.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Bratz, Norbert Meyer, Hartmann Konig, Helmut Walter, Matthias Gerber, Karl-Otto Westphalen
  • Patent number: 5716963
    Abstract: Said derivatives have the general formula (I) and are: ##STR1## (I-A) 4,6,7-trimethyl-5,8,8a,10a-tetrahydro-1H-1-azaanthracen-2,9,10-trione; (I-B) 2-ethoxy-3-methyl-1-azaanthracen-9,10-dione; (I-C) 3-ethyl-1,8-dihydro-1H-1,8-diazaanthracen-2,7,9,10-tetraone; (I-d) 2-acethoxy-3-methyl-1,8-diazaanthracen-2,9,10-trione; (I-e) 6-fluor-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-f) 6-dimethylamino-4-methyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-g) 4-methyl-5-(2-nitrophenyl)-5,8-dihydro-1H-1,8-diazaanthracen-2,9,10-trione ; (I-h) 3,5-dimethyl-1,8-dihydro-1,8-diazaanthracen-2,7,9,10-tetraone; (I-i) 3,6-difluor-1,8-diazaanthracen-9,10-dione; (I-j) 6-methyl-3-phenyl-1H-1,8-diazaanthracen-2,9,10-trione; (I-k) 3-fluor-4-methyl-1-dihydro-1-azaanthracen-9,10-dione; 3-fluor-1-azaanthracen-1,10-dione. Application as antitumor agents.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: February 10, 1998
    Assignee: Universidad Complutense De Madrid
    Inventors: Carmen Avendano Lopez, Dolores Garcia Gravalos
  • Patent number: 5700761
    Abstract: Compounds of Formula I having herbicidal utility are disclosed: ##STR1## wherein Q, R.sup.1, R.sup.2, V, m and p are defined in the text, including compositions containing such compounds, and a method for controlling weeds employing such compounds.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: December 23, 1997
    Assignees: E. I. Du Pont de Nemours and Company, Degussa Aktiengesellschaft
    Inventor: John Jolly Kilama
  • Patent number: 5698568
    Abstract: Quinuclidine derivatives of the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein m, P, Z, Y, R.sup.1, R.sup.2 and R.sup.3 are as defined below. The compounds are substance P antagonists and, therefore, are useful in treating gastrointestinal disorders, central nervous system disorders, inflammatory diseases, pain and migraine.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: December 16, 1997
    Assignee: Pfizer Inc.
    Inventor: John Adams Lowe, III
  • Patent number: 5696130
    Abstract: Non-steroidal compounds which are high affinity, high selectivity modulators for steroid receptors are disclosed. Also disclosed are pharmaceutical compositions incorporating such compounds, methods for employing the disclosed compounds and compositions for treating patients requiring steroid receptor agonist or antagonist therapy, intermediates useful in the preparation of the compounds and processes for the preparation of the steroid receptor modulator compounds.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 9, 1997
    Assignee: Ligand Pharmaceuticals Incorporated
    Inventors: Todd K. Jones, David T. Winn, Mark E. Goldman, Lawrence G. Hamann, Lin Zhi, Luc J. Farmer, Robert L. Davis
  • Patent number: 5688791
    Abstract: Disclosed are an aryl group- or heterocyclic group-substituted aminoquinolone compound represented by the formula (Ia), (Ib) or (Ic): ##STR1## wherein each of the substitutents are defined in the specification, or a salt of the compound, and an AIDS curing agent containing the same as an effective ingredient.
    Type: Grant
    Filed: September 11, 1995
    Date of Patent: November 18, 1997
    Assignee: UBE Industries, LTD.
    Inventors: Tomio Kimura, Tetsushi Katsube
  • Patent number: 5686459
    Abstract: Novel dioxopyrrolo-pyrrole derivatives of the formula ##STR1## as well as hydrates or solvates thereof, which inhibit thrombin-induced or Factor Xa-induced platelet aggregation and fibrinogen clotting in blood plasma. The derivatives can be manufactured from the corresponding maleimides which are N-substituted by .alpha.-amino carboxylic acids of the formula HN(R.sup.2)CH(R.sup.4)COOH, or functional derivatives thereof; and ketones or aldehydes of the formula R.sup.5 C(O)R.sup.6.
    Type: Grant
    Filed: February 26, 1996
    Date of Patent: November 11, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Francois Diederich, Ulrike Obst, Sabine Wallbaum, Lutz Weber
  • Patent number: 5624933
    Abstract: Method of preparation of 6-fluoro-2-halogen quinoline of general formula (I) wherein R is a hydrogen atom or an alkyl radical and Hal and Hal' are identical or different halogen atoms. The invention is characterized in that a halogenating agent is made to act on hydroxy-1 quinoline of general formula (II) wherein Hal is defined as above and R.sub.1 is defined as R excepting a hydrogen atom, the acid function being optionally released if a 6-fluoro-2-halogen quinoline is to be obtained for which R is a hydrogen atom.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 29, 1997
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Herve Garcia, Roland Jacquot, Patrick Leon
  • Patent number: 5609867
    Abstract: This invention provides novel antitumor agents having the formula: ##STR1## wherein A, B, G, W, R.sup.1, R.sup.2, R.sup.3, n, m and Z are described in the specification which have activity as anticancer agents and inhibit leukemia and solid tumor growth in a mammal.
    Type: Grant
    Filed: August 29, 1995
    Date of Patent: March 11, 1997
    Assignee: American Cyanamid Company
    Inventor: Hwei-Ru Tsou
  • Patent number: 5605905
    Abstract: Azaanthracene-triones of the formula: ##STR1## (in which: R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are the same or are different and each is a hydrogen atom or a lower alkyl group;R.sup.3 is a hydrogen atom, a lower alkyl group, a phenyl group or an amino-substituted phenyl group; andX is a --CH--, .dbd.N-- or --NH--, whereby the ring containing the group X is a benzene, pyridine or dihydropyridene ring)have antitumoral activity.
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: February 25, 1997
    Assignee: Universidad Complutense de Madrid
    Inventors: Carmen Avendano, Miguel A. Alonso, Modesta Espada, Dolores Garcia-Gravalos, Jose C. Mendendez, Blanca Ocana, Jose M. Perez
  • Patent number: 5580888
    Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, wherein R.sup.1 is an optionally substituted alkyl group; X is --O--, --S-- or --N(R.sup.6)--, where R.sup.6 is a hydrogen atom or an alkyl group; R.sup.2 is an optionally substituted alkyl, alkenyl, cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a group --(CH.sup.2).sub.n Ar, where Ar is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms and n is zero or an integer 1, 2 or 3; R.sup.5 is a hydrogen atom or an optionally substituted alkyl group; and the salts, solvates, hydrates and N-oxides. Compounds according to the invention are potent, selective and orally active PDE IV inhibitors and are useful in the prophylaxis and treatment of asthma.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 3, 1996
    Assignee: Celltech Therapeutics Limited
    Inventors: Graham J. Warrellow, Ewan C. Boyd, Rikki P. Alexander
  • Patent number: 5567710
    Abstract: In accordance with the present invention, there is provided a class of polycyclic fused ring compounds which are modulators of acetylcholine receptors. The compounds of the invention displace acetylcholine receptor ligands from their binding sites. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors.
    Type: Grant
    Filed: October 13, 1994
    Date of Patent: October 22, 1996
    Assignee: SIBIA Neurosciences, Inc.
    Inventors: Jeffrey P. Whitten, Ian A. McDonald, Jean-Michel Vernier
  • Patent number: 5561232
    Abstract: Compounds of formulaA(B).sub.x, (I),whereinx is an integer from 1 to 4,A is the radical of a chromophore of the quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, isoindoline, dioxazine, phthalocyanine or azo series, which radical contains x N-atoms attached to B, preferably with at least one directly adjacent or conjugated carbonyl group,B is a group of formula ##STR1## and, if x is 2, 3 or 4, may also be one, two or three hydrogen atoms. The symbols Q, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X, Y, Z, m and n, are as defined in claim 1. These carbamate group-containing soluble chromophores am distinguished by outstanding solid state fluorescence in the UV range as well as the by ease with which they can be converted to the corresponding pigments in the substrate in which they are incorporated.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: October 1, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Zhimin Hao, John S. Zambounis, Abul Iqbal
  • Patent number: 5556861
    Abstract: This invention relates to a novel 1,8 benzo[b]naphythyridine derivative of general formula (I), ##STR1## wherein R is H or a hydroxy, amino or alkylamino radical optionally substituted by amino or hydroxy, or R is dialkylamino of which the alkyl portions may form, with the nitrogen atom, a 5- or 6-membered heterocyclic ring which optionally contains a further heteroatom chosen from nitrogen, oxygen or sulphur, or R is C.sub.3-6 cycloalkylamino or an alkanylamino, N-alkyl N-alkanylamino or aminoalkylphenylamino radical; R.sub.1 and R.sub.2, which are the same or different, are in positions 2 and 3 and represent H, alkyl, C.sub.2-4 alkenyl, phenyl, or substituted phenyl, or R.sub.1 and R.sub.2 are in position 2 and represent alkyl; R.sub.3 is H or alkyl, fluoroalkyl, carboxyalkyl, C.sub.3-6 cycloalkyl, fluorophenyl, difluorophenyl, alkyloxy or alkylamino; and R.sub.4 is H or F, wherein the C.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 17, 1996
    Assignee: Laboratoire Roger Bellon
    Inventors: Eric Bacque, Michel Barreau, Jean-Francois Desconclois, Philippe Girard, Michel Kryvenko, Marc P. Lavergne, Jean-Marc Paris, Guy Picaut
  • Patent number: 5512564
    Abstract: The present invention concerns thiazolo- 2,3-a!pyrrole and oxazolo- 1,2-a!pyrrole derivatives of formula I ##STR1## in which HET represents a heterocyclic ring with 3-7 ring atoms which can be substituted by one, two or three residues R.sup.1 which can be the same or different,Y represents an oxygen or sulphur atom, or a SO or SO.sub.2 group,X can be an oxygen or sulphur atom,R denotes an aliphatic residue with 1-9 C-atoms which can be substituted by phenyl or denotes a phenyl ring or a carbocyclic ring with 7-15 C atoms or a heterocyclic ring system each having 5 or 6 ring atoms,in which the aforementioned phenyl rings, carbocyclic rings or heterocyclic ring system can be substituted once or several times, if desired, and R1-R5 denote hydrogen or an aliphatic residue, as well as their tautomers, enantiomers, diastereomers and physiologically tolerated salts.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: April 30, 1996
    Assignee: Boehringer Mannheim GmbH
    Inventors: Harald Zilch, Herbert Leinert, Alfred Mertens
  • Patent number: 5489603
    Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5484921
    Abstract: This invention relates to a method for the preparation of benzo[b]naphthyridines having the general formula (I) ##STR1## comprising: 1) condensation of an amine having the formula R'--NH--CH.sub.2 --CH.sub.2 --R" with a chlorofluoroquinoline of formula (II) ##STR2## 2) cyclization of the obtained fluoroquinoline of formula (IV) ##STR3## and; 3) oxidation of tetrahydro-1,2,3,4benzo[b]naphthyridine-1,8 of formula (V) ##STR4## is effected, and then, optionally, the ester obtained is transformed into an acid and optionally into a salt.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: January 16, 1996
    Assignee: Laboratoire Roger Bellon
    Inventors: Christophe Daubie, Jean-Jacques Legrand, Clive Pemberton
  • Patent number: 5439916
    Abstract: Novel polycyclic quinoline, naphthyridine and pyrazinopyridine derivatives are disclosed which are useful for treating allergic reactions, inflammation, peptic ulcers, hypertension, and hyperproliferative skin diseases and for suppressing the immune response in mammals. Methods for preparing said compounds are also disclosed.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: August 8, 1995
    Assignee: Schering Corporation
    Inventors: Ashit K. Ganguly, Richard J. Friary, John H. Schwerdt, Marvin I. Siegel, Sidney R. Smith, Edmund J. Sybertz
  • Patent number: 5389629
    Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: February 14, 1995
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Gregory M. Shutske, Richard C. Effland
  • Patent number: 5359066
    Abstract: A compound represented by the following general formula: ##STR1## which is useful as an intermediate for production of a clinically excellent synthetic antibacterial, a salt thereof, and a process for producing the same.In said formula,R.sup.1 is a hydrogen atom or a carboxyl-protecting group;R.sup.2 is a hydrogen atom or a lower alkyl group;X.sup.1 is a hydrogen atom or a halogen atom;X.sup.2 is a halogen atom;X.sub.a.sup.5 is a hydrogen atom or a halogen atom;A is a methylene group; a group of >CH--COOR.sup.4, etc.,in which R.sup.4, R.sup.5 and R.sup.6 each are a hydrogen atom or a carboxyl-protecting group;B is a methylene group or a carbonyl group;provided that both A and B must not be methylene groups at the same time.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: October 25, 1994
    Assignees: Wakunaga Pharmaceutical Co., Ltd., Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Hideo Tsutsumi, Takeshi Terasawa, David Barrett, Masayoshi Murata, Kazuo Sakane, Akira Yazaki, Satoshi Inoue
  • Patent number: 5346904
    Abstract: Compound of the formula I ##STR1## wherein the substituents have the meanings given in the description, are new active bronchodilators.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: September 13, 1994
    Assignee: BYK Gulden Lomberg Chemische Fabrik GmbH
    Inventors: Dieter Flockerzi, Kurt Klemm
  • Patent number: 5328908
    Abstract: Antimicrobial quinolone thiourea compounds of the general formula: ##STR1## wherein (1) A.sup.1, A.sup.2, A.sup.3, R.sup.1, R.sup.3, R.sup.4, and R.sup.6 form any of a variety of quinolone and related heterocyclic structures similar to those known in the art to have antimicrobial activity; and(2)(1) R.sup.1 is X, R.sup.3 is X, or both R.sup.1 and R.sup.3 are X; and(2) X is --R.sup.15 --N(R.sup.16)(R.sup.17) or --R.sup.15 --R.sup.18 --N(R.sup.19)(R.sup.17), where(a)(1) R.sup.15 is nil, alkyl, a carbocyclic ring, or a heterocyclic ring; and(2) R.sup.16 is hydrogen; alkyl; alkenyl; a carbocyclic ring; a heterocyclic ring; or(3) when X is R.sup.15 --N(R.sup.16)(R.sup.17), R.sup.16 and R.sup.15 may together comprise a heterocyclic ring including the nitrogen atom to which R.sup.15 and R.sup.16 are bonded;(b) R.sup.17 is C(.dbd.S)--NR.sup.20 R.sup.21 ; where R.sup.20 is, hydrogen, alkyl, alkenyl, a carbocyclic ring or a heterocyclic ring; and R.sup.21 is R.sup.20 or N(R.sup.20)(R.sup.20); or R.sup.20 and R.sup.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: July 12, 1994
    Assignee: Procter & Gamble Pharmaceuticals, Inc.
    Inventors: Thomas P. Demuth, Jr., Ronald E. White
  • Patent number: 5264575
    Abstract: Novel 2,6-methano-1,3-benzodiazocines, intermediates, processes for the preparation thereof, and methods for alleviating pain and for alleviating various memory dysfunctions characterized by a decreased cholinergic function, such as Alzheimer's disease, utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: November 23, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Richard C. Allen, Marc N. Agnew, David M. Fink
  • Patent number: 5254595
    Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: October 19, 1993
    Assignee: Elf Sanofi
    Inventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
  • Patent number: 5250681
    Abstract: A piperidine compound of the formula (I): ##STR1## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.dbd.CH--, --C.dbd.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.2 -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.dbd.CH--, --C.dbd.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: October 5, 1993
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masataka Shoji, Kozo Toyota, Chikahiko Eguchi, Ryota Yoshimoto, Yoshikatsu Koyama, Hideki Domoto, Akira Kamimura
  • Patent number: 5242918
    Abstract: A compound having the formula ##STR1## wherein R.sup.4 and R.sup.5 independently are hydrogen, halogen, CF.sub.3, CN, NO.sub.2 or SO.sub.2 NR.sup.1 R.sup.2 whereinR.sup.1 is hydrogen or straight, C.sub.1-6 -alkyl which may be branched or cyclic,R.sup.2 is hydrogen or straight, C.sub.1-6 -alkyl which may be branched or cyclic,or wherein R.sup.1 and R.sup.2 together represent --(CH.sub.2).sub.n --A--(CH.sub.2).sub.m --, wherein A is O, S, CH.sub.2 or NR.sup.I, wherein R.sup.I is H, C.sub.1-6 -alkyl which may be straight, branched or cyclic, n is 0, 1, 2, 3, 4, 5 and m is 0, 1, 2, 3, 4, 5;Q is NOH or O;Z=O, S, N--R.sup.II, ##STR2## wherein R.sup.II, R.sup.III, R.sup.IV and R.sup.V independently are hydrogen, benzyl, C.sub.1-6 carboxylic acid-acyl, C.sub.1-6 -alkoxy which may be branched or cyclic, or C.sub.1-6 -alkyl which may be branched or cyclic;X is --(CH.sub.2).sub.o -- wherein o is 0, 1, 2, or 3;Y is --(CH.sub.2).sub.p -- wherein p is 0, 1, 2 or 3;.alpha. and .beta.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: September 7, 1993
    Assignee: NeuroSearch A/S
    Inventors: Frank Watjen, Bjarne H. Dahl, Jorgen Drejer, Leif H. Jensen
  • Patent number: 5208330
    Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: May 4, 1993
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Gregory M. Shutske, Richard C. Effland
  • Patent number: 5202440
    Abstract: Compounds selected from the group consisting of 9-amino-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-2-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-8-fluoro-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-4-oxa-1,2,3,4,5,6,7,8-octahydro-acridine or a pharmaceutical acceptable salt thereof are useful treating Alzheimer's disease.
    Type: Grant
    Filed: April 27, 1990
    Date of Patent: April 13, 1993
    Assignee: Pfizer Inc.
    Inventor: Manoj C. Desai
  • Patent number: 5190951
    Abstract: Quinoline derivatives of the formula, ##STR1## wherein > A represents a group >N--(CH.sub.2).sub.n --, >C.dbd., >C.dbd.CH(CH.sub.2).sub.n --, or >CH(CH.sub.2).sub.n --, wherein n is an integer of 0-7; Y represents a group >C.dbd.O or >CHOH, R.sup.1 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group, R.sup.2 is a hydrogen atom, a halogen atom, an alkyl group, a hydroxy group, an alkoxy group, a phenyl group which may have a substituent, a phenoxy group, an alkanoyloxy group, or an amino group which may have a substituent, R.sup.3 is a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group, and m is an integer of 1-3. The compounds and their salts exhibit a superior antiacetylcholinesterase activity with no side effects and are effective for the prevention or cure of senile dementia or memory disturbance.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: March 2, 1993
    Assignee: SS Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Hasegawa, Kazuo Isomae, Takeshi Kotsugai, Noriaki Shioiri, Kumiko Sekine, Naokata Taido, Susumu Sato, Tadayuki Kuraishi
  • Patent number: 5177210
    Abstract: 2,7-Diazabicyclo[3.3.0]octanes, suitable for 7-position substituents or antibacterially active quinolone carboxylic acids, of the formula ##STR1## in which R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.7 and R.sup.8 may be identical or different and in each case denote H, C.sub.1 -C.sub.5 -alkyl (optionally substituted by halogen, hydroxyl or C.sub.1 -C.sub.3 -alkoxy), C.sub.1 -C.sub.3 -alkoxycarbonyl or C.sub.6 -C.sub.12 -aryl,R.sup.4 additionally denotes halogen,R.sup.2 and R.sup.6 may be identical or different, denote H, C.sub.1 -C.sub.6 -alkyl, benzyl, C.sub.6 -C.sub.12 -aryl, C.sub.1 -C.sub.3 -alkanoyl, benzoyl or C.sub.1 -C.sub.5 -alkoxycarbonyl, orR.sup.2 and R.sup.3 together denote a bridge of the structure (CH.sub.2).sub.n, n=2-4, CH.sub.2 --CHOH--CH.sub.2, CH.sub.2 --S--CH.sub.2 or C(CH.sub.3).sub.2 --S--CH.sub.2,excluding 2,7-diazabicyclo[3.3.0]octane.Also their preparation by the reaction ##STR2## Intermediates II are also new.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: January 5, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Schenke, Uwe Petersen
  • Patent number: 5118688
    Abstract: The present invention comprises certain quinoline lactams of formula I; pharmaceutically acceptable salts of the compounds of formula I; pharmaceutical compositions containing a compound of formula I, or a pharmaceutically acceptable salt thereof, for use in the treatment of anxiety; and processes for the manufacture of the compounds of formula I, as well as intermediates for use in such manufacture.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: June 2, 1992
    Assignee: ICI Americas Inc.
    Inventor: James B. Campbell
  • Patent number: 5101032
    Abstract: Cycloalkylidene dyes have the formula ##STR1## where m is 0 or 1,L is a chemical bond or C.sub.1 -C.sub.2 -alkylene, which may be substituted,R.sup.1 is hydrogen, C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl or C.sub.3 -C.sub.7 -cycloalkyl,Y is oxygen or two hydrogens,X.sup.1 is oxygen andX.sup.2 is C.sub.1 -C.sub.8 -alkanoyloxy, substituted or unsubstituted benzoyloxy, C.sub.1 -C.sub.6 -trialkylsilyloxy or a radical of the formula OR.sup.1 or NR.sup.2 R.sup.3, where R.sup.1 is as defined above and R.sup.2 and R.sup.3 are identical or different and each is independently of the other C.sub.1 -C.sub.20 -alkyl, which may be phenyl-substituted, substituted or unsubstituted phenyl, naphthyl, or C.sub.3 -C.sub.7 -cycloalkyl or R.sup.2 and R.sup.3 together with the nitrogen atom joining them are saturated heterocyclyl, or else one of R.sup.2 and R.sup.3 is hydrogen, or X.sup.1 and X.sup.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Dieter Martin, Bernhard Albert, Knut Kessel
  • Patent number: 5091535
    Abstract: An organic photochromic compound with improved long term preservability, thermal stability, the repetition character of the record and the like and useful as recording-memory materials or photosensitizers, comprising dimers of the compounds selected from the group consisting of pyrido[3,4-g]isoquinoline, pyrido[2,3-g]quinoline, pyrido[3,2-g]quinoline and pyrido[3,2-g]quinoline derivatives.
    Type: Grant
    Filed: April 24, 1990
    Date of Patent: February 25, 1992
    Assignee: Seikisui Kagaku Kogyo Kabushiki Kaisha
    Inventors: Shigeru Nomura, Takahiro Hidaka
  • Patent number: 5086179
    Abstract: This invention is directed to certain dibenzofurancarboxamides and dibenzofurancarboxamide acids and their use as 5HT.sub.3 antagonists having unique CNS, anti-emetic and gastric prokinetic activity void of any significant D.sub.2 receptor binding properties. Further, this invention relates to a process for the synthesis of stereoisomeric compounds having such CNS, anti-emetic and gastric prokinetic activity.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: February 4, 1992
    Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.
    Inventors: Matthew R. Powers, Raymond D. Youssefyeh, William L. Studt, Frederick A. Golec