One Of The Cyclos Is Five-membered Patents (Class 546/84)
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Patent number: 6136819Abstract: Compound of general formula I ##STR1## wherein A denotes a benzo, indolo or thienyl group;B denotes the group --O--, --S-- or --CHR.sup.5 --, wherein R.sup.5 is hydrogen, (C.sub.1 -.sub.6)alkyl, phenyl or benzyl;R.sup.3 denotes 2- or 3-thienyl, (C.sub.4 -.sub.7)cycloalkyl, (C.sub.4 -.sub.6)cycloalkyl(C.sub.1 -.sub.5)alkyl or ##STR2## wherein R is (C.sub.1 -.sub.4)alkyl, hydroxy, --N.sub.3, halogen (F, Cl, Br, I), CF.sub.3 or (C.sub.1 -.sub.4)alkoxy,u is 0, 1, 2 or 3, andm, R.sup.2, R.sup.4, R.sup.7, R.sup.8 and R.sup.9 are as defined in the specification, as well as pharmaceutical preparations containing these compounds and the pharmaceutical use thereof.Type: GrantFiled: June 10, 1999Date of Patent: October 24, 2000Assignee: Boehringer Ingelheim GmbHInventors: Otto Roos, Walter Losel, Dietrich Arndts
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Patent number: 6127542Abstract: 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 cyloalkyl, 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: GrantFiled: September 21, 1999Date of Patent: October 3, 2000Assignee: ICOS CorporationInventor: Alain Claude-Marie Daugan
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Patent number: 6121278Abstract: A compound of formula I: ##STR1## or a pharmaceutically acceptable salt, hydrate, ester, solvate, prodrug, metabolite, stereoisomer, or mixtures thereof, wherein:Y represents the atoms necessary to form a fused 5- to 6-membered, aromatic or non-aromatic, heterocyclic ring containing at least one nitrogen heteroatom in a 1,3-relationship with the nitrogen atom depicted in formula I, wherein Y may be unsubstituted or substituted with at least one alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, double bonded oxygen, or --COOR.sup.5 group, or a moiety selected from the group consisting of: ##STR2## wherein R.sup.5 and R.sup.7 are independently hydrogen or alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl, or aryl.Type: GrantFiled: September 1, 1998Date of Patent: September 19, 2000Assignee: Guilford Pharmaceuticals, Inc.Inventors: Paul F. Jackson, Keith M. Maclin, Jie Zhang
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Patent number: 6117881Abstract: Carboline derivatives of formula (I), are potent and selective inhibitors of cyclic guanosine 3',5'-monophosphate specific phosphodiesterase (cGMP specific PDE) and have utility in a variety of therapeutic areas where such inhibition is thought to be beneficial, including the treatment of cardiovascular disorders.Type: GrantFiled: April 23, 1999Date of Patent: September 12, 2000Assignee: Icos CorporationInventor: Agnes Bombrun
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Patent number: 6110929Abstract: Thiazolo-, oxazolo- and selenazolo[4,5-c]quinolin-4-amines and analogs thereof are described including methods of manufacture and the use of novel intermediates. The compounds are immunomodulators and induce cytokine biosynthesis, including interferon and/or tumor biosynthesis, necrosis factor, and inhibit the T-helper-type 2 immune response. The compounds are further useful in the treatment of viral and neoplastic diseases.Type: GrantFiled: July 27, 1999Date of Patent: August 29, 2000Assignee: 3M Innovative Properties CompanyInventors: John F. Gerster, Kyle J. Lindstrom, Gregory J. Marszalek, Bryon A. Merrill, John W. Mickelson, Michael J. Rice
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Patent number: 6083505Abstract: An immunogen/vaccine adjuvant composition containing an immunogen in an amount effective to stimulate an immune response and as a vaccine adjuvant a 1H-imidazo[4,5-c]quinolin-4-amine in an amount effective to increase the immune response to the immunogen.Type: GrantFiled: March 24, 1994Date of Patent: July 4, 2000Assignee: 3M Innovative Properties CompanyInventors: Richard L. Miller, Mark A. Tomai, David I. Bernstein, Christopher J. Harrison
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Patent number: 6071947Abstract: 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: GrantFiled: November 12, 1998Date of Patent: June 6, 2000Assignee: Pharmacia & Upjohn S.p.A.Inventors: Roberto D'Alessio, Marcellino Tibolla, Alberto Bargiotti, Anna Maria Isetta, Mario Ferrari, Francesco Colotta
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Patent number: 6060432Abstract: Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation ##STR1## wherein X, Y, J, R.sup.1, and R.sup.2 are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.Type: GrantFiled: October 24, 1996Date of Patent: May 9, 2000Assignees: E. I. du Pont de Nemours and Company, Degussa AktiengesellschaftInventors: Edward John Adams, Karlheinz Drauz, Wonpyo Hong, Balreddy Kamireddy, Wallace Christian Petersen, Matthias Schaefer, Christoph Weckbecker
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Patent number: 6025494Abstract: 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: GrantFiled: August 12, 1998Date of Patent: February 15, 2000Assignee: ICOS CorporationInventor: Alain Claude-Marie Daugan
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Patent number: 6011044Abstract: The present invention relates to a novel pyrrolo[3,2-c]quinoline derivatives containing haloalkoxy group, represented by Formula I, their pharmaceutically acceptable salts; process for preparation thereof; and pharmaceutical composition thereof for treating gastric ulcer. ##STR1## in which R.sub.1 is haloalkoxy group of C.sub.1 -C.sub.6 including trifluoromethoxy, difluoromethoxy and trifluoroethoxy group.R.sub.2 and R.sub.3, which are the same or different, are each hydrogen, halogen, hydroxy, benzyloxy, alkyl group of C.sub.1 -C.sub.6, alkoxy group of C.sub.1 -C.sub.6.A is --CH.sub.2 --CH.sub.2 -- or --CH.dbd.CH--, andR.sub.4 is hydrogen, halogen, amino, alkylamino group of C.sub.1 -C.sub.6, and NH(CH.sub.2).sub.n OH in which n is 1-6. Pyrrolo[3,2-c]quinoline derivatives having haloalkoxy group, and their pharmaceutically acceptable salts, which reversibly inhibit gastric acid secretion of mammal, are usefully utilized for gastric ulcer therapeutics.Type: GrantFiled: August 7, 1998Date of Patent: January 4, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Joong-Kwon Choi, Sung-Soo Kim, Eul-Kyun Yum, Seung-Kyu Kang, Yea-Kang Yoo, Hyae-Gyeong Cheon, Hyo-Jung Kim
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Patent number: 5994366Abstract: 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: GrantFiled: June 25, 1998Date of Patent: November 30, 1999Assignee: Akzo Nobel NVInventors: Dirk Leysen, Gerardus Stephanus Franciscus Ruigt
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Patent number: 5958942Abstract: Tricyclic compound of the formula: ##STR1## wherein ring A is a nitrogen-containing heterocyclic ring, having two nitrogen atoms as the hetero-atoms, which is optionally substituted with oxo or thioxo; ring Q may optionally be substituted; Y is an optionally substituted hydrocarbon group, an optionally substituted hydroxyl group or an optionally substituted mecapto group, excluding for methyl group as Y; R.sup.1 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group or an acyl group, or a salt thereof, having excellent PDGF-inhibiting activities, antihypertensive activities, activities of ameliorating renal diseases and activities of lowering lipid level.Type: GrantFiled: January 14, 1997Date of Patent: September 28, 1999Assignee: Takeda Chemical Industries, Ltd.Inventors: Muneo Takatani, Yumiko Shibouta, Kiminori Tomimatsu, Tetsuji Kawamoto
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Patent number: 5952498Abstract: The invention relates to a process and intermediates for the preparation of enantiomerically pure cycloalkanoindolecarboxylic acids and azaindolecarboxylic acids and pyrimido?1,2a!indolecarboxylic acids and their activated derivatives, characterized in that the tolyl acetic acid is first esterified with a chiral alcohol, then diastereoselective substitution at .alpha.-carbon atoms is carried out and this product is halogenated in the tolyl group and then reacted with appropriate cycloalkanoindoles, cycloalkanoazaindoles or pyrimido?1,2a!indoles. It is possible by this method to prepare specifically, in high purity, the enantiomerically pure carboxylic acids which are intermediates for valuable medicaments.Type: GrantFiled: March 31, 1997Date of Patent: September 14, 1999Assignee: Bayer AktiengesellschaftInventors: Jan-Bernd Lenfers, Peter Fey, Paul Naab, Kai Van Laak
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Patent number: 5929085Abstract: 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: GrantFiled: January 22, 1997Date of Patent: July 27, 1999Assignee: Astra AktiebolagInventors: James MacDonald, James Matz, William Shakespeare
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Patent number: 5908932Abstract: This invention encompasses compounds of formula (I), and pharmaceutically acceptable non-toxic salts thereof wherein X and Y are the same or different and represent oxygen or H.sub.2 with the proviso that not both X and Y are H.sub.2 ; W represents phenyl, thienyl, or pyridyl, each of which may be unsubstituted or mono or disubstituted with organic or inorganic substituents; and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are variables representing organic and inorganic substituents. These compounds are highly selective agonists, antagonists or inverse agonists for GABAs brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine drugs, and enhancement of memory.Type: GrantFiled: February 13, 1997Date of Patent: June 1, 1999Assignee: Neurogen CorporationInventors: Kenneth Shaw, Jun Yuan
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Patent number: 5866587Abstract: Compound of formula (I): ##STR1## in which: m, n, which are identical or different, represent 0, 1 or 2,R.sub.1, R.sub.2, which are identical or different, represent hydrogen, optionally substituted alkyl, aryl, or form with the carbon atom carrying them carbonyl or (C.sub.3 -C.sub.7)cycloalkyl,R.sub.3 represents hydrogen, alkyl, hydroxyl or aryl,R.sub.4 represents any of the groups as defined in the description,X represents --SO.sub.2 --, --CO-- or --SO.sub.2 NH--,R.sub.5 represents optionally substituted alkyl, (C.sub.3 -C.sub.7)cycloalkyl, aryl or heterocyclic,A represents an aryl ring or a heterocycle,its isomers as well as its addition salts with a pharmaceutically acceptable acid or base and medicinal products containing the same are useful as metalloprotease inhibitors.Type: GrantFiled: April 25, 1997Date of Patent: February 2, 1999Assignee: Adir Et CompagnieInventors: Guillaume de Nanteuil, Joseph Paladino, Georges Remond, Ghanem Atassi, Alain Pierre, Gordon Tucker, Jacqueline Bonnet, Massimo Sabatini
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Patent number: 5854275Abstract: The invention relates to a compound of the formula I ##STR1## wherein R.sup.1 is a cyclic imide group and X, Y, R.sup.2, and R.sup.3 are as defined herein. The invention further relates to pharmaceutical compositions containing, and methods of using, compounds of the formula I. Compounds of the formula I are useful in the treatment of diseases related to the production of matrix metalloproteinases and tumor necrosis factor.Type: GrantFiled: May 13, 1997Date of Patent: December 29, 1998Assignee: Pfizer Inc.Inventor: Ralph P. Robinson
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Patent number: 5843955Abstract: The present invention relates to compound LK6-A represented by the formula: ##STR1## which has immunosuppressive activity, and pharmaceutically acceptable salts thereof.Type: GrantFiled: September 30, 1996Date of Patent: December 1, 1998Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Tatsuya Tamaoki, Hiroyuki Nagata, Isami Takahashi, Mayumi Yoshida, Yumiko Aotani, Katsuhiko Ando, Keiko Ochiai
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Patent number: 5834481Abstract: Heterotricyclically substituted phenyl-cyclohexanecarboxylic acid derivatives are prepared by reacting the heterocyclic compounds with cyclohexanecarboxylic acid derivatives which are substituted by benzyl halide radicals. The compounds can be employed as active compounds in medicaments.Type: GrantFiled: July 8, 1997Date of Patent: November 10, 1998Assignee: Bayer AktiengesellschaftInventors: Ulrich E. Muller, Jurgen Dressel, Peter Fey, Rudolf H. Hanko, Walter Hubsch, Thomas Kramer, Matthias Muller-Gliemann, Martin Beuck, Stanislav Kazda, Stefan Wohlfeil, Andreas Knorr, Johannes-Peter Stasch, Siegfried Zaiss
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Patent number: 5801174Abstract: The present patent application discloses compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof whereinR.sup.1 is hydrogen, alkyl or benzyl;X is O or NOR.sup.2, wherein R.sup.2 is hydrogen, alkyl or benzyl;Y is N--R.sup.4 wherein R.sup.4 is hydrogen, OH or alkyl;n is 0 or 1;R.sup.6 is phenyl which is substituted one or more times with substituents selected from the group consisting of SO.sub.2 NR'R", CONR'R", and COR'"wherein R' and R" each independently are hydrogen, alkyl, or --(CH.sub.2).sub.p --W, wherein p is 0, 1, 2, 3, 4, 5, or 6, and W is hydroxy, amino, alkoxycarbonyl, or phenyl which may be substituted one or more times with substituents selected from the group consisting of halogen, CF.sub.3, NO.sub.2, amino, alkyl, alkoxy or methylenedioxy; or wherein R' and R" together is (CH.sub.2).sub.r Z(CH.sub.2).sub.s wherein r and s each independently are 0, 1, 2, 3, 4, 5, or 6 and Z is O, S, CH.sub.2 or NR"" wherein R"" is hydrogen, alkyl, or --(CH.sub.2).sub.Type: GrantFiled: May 20, 1997Date of Patent: September 1, 1998Assignee: Neurosearch A/SInventors: Peter Moldt, Frank Watjen
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Patent number: 5780480Abstract: Fibrinogen receptor antagonists of the general formula:X-A-Y-Z-B Iand which includes, for example, the compounds of formula ##STR1## are useful for inhibiting the binding of fibrinogen to blood platelets, inhibiting the aggregation of blood platelets, treating thrombus formation or embolus formation, and preventing thrombus or embolus formation.Type: GrantFiled: February 26, 1997Date of Patent: July 14, 1998Assignee: Merck & Co., Inc.Inventors: John Wai, Thorsten E. Fisher, Mark E. Duggan, George D. Hartman, James J. Perkins
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Patent number: 5780493Abstract: The present patent application discloses compounds having formula (I) or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, alkyl or benzyl; X is O or NOR.sup.2, wherein R.sup.2 is hydrogen, alkyl or benzyl; Y is N--R.sup.4 wherein R.sup.4 is hydrogen, OH or alkyl; n is 0 or 1; R.sup.6 is phenyl, naphthyl, thienyl, pyridyl, all of which may be substituted one or more times with substituents selected from the group consisting of halogen; CF.sub.3, NO.sub.2, amino, alkyl, alkoxy and phenyl; A is a ring of five to seven atoms fused with the benzo ring at the positions marked a and b. The compounds are useful in the treatment of cerebrovascular disorders for example.Type: GrantFiled: October 16, 1997Date of Patent: July 14, 1998Assignee: NeuroSearch A/SInventors: Frank Watjen, Jorgen Drejer
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Patent number: 5744478Abstract: The present invention relates to new thiazolo?3,2-a!quinoline and thiazolo?3,2-a!naphthyridine derivatives of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, Z and X have the meaning indicated in the description, processes for their preparation and their use in antibacterial compositions.Type: GrantFiled: February 21, 1997Date of Patent: April 28, 1998Assignee: Bayer AktiengesellschaftInventors: Thomas Jaetsch, Werner Hallenbach, Thomas Himmler, Klaus-Dieter Bremm, Rainer Endermann, Franz Pirro, Michael Stegemann, Heinz-Georg Wetzstein
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Patent number: 5731322Abstract: Tricyclic derivatives of octahydroisoquinoline of formula (I), wherein n is zero or 1 and if n is zero, one of X or Y is NH, oxygen or sulphur, and the other is NH, CH or a R.sub.4 - or R.sub.5 -substituted carbon atom; if n is 1, then X and Y are both nitrogen, or one of them is nitrogen and the other is CH or an R.sub.4 - or R.sub.5 -substituted carbon atom, have selective receptor agonist or antagonist activity, and are of potential therapeutic utility as analgesics or immunomodulating and/or cardiovascular agents.Type: GrantFiled: April 18, 1996Date of Patent: March 24, 1998Assignee: SmithKline Beecham S.p.A.Inventors: Giulio Dondio, Silvano Ronzoni
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Patent number: 5708003Abstract: Heterotricyclically substituted phenyl-cyclohexane-carboxylic acid derivatives are prepared by reacting the heterocyclic compounds with cyclohexanecarboxylic acid derivatives which are substituted by benzyl halide radicals. The compounds can be employed as active compounds in medicaments.Type: GrantFiled: September 8, 1995Date of Patent: January 13, 1998Assignee: Bayer AktiengesellschaftInventors: Ulrich E. Muller, Jurgen Dressel, Peter Fey, Rudolf H. Hanko, Walter Hubsch, Thomas Kramer, Matthias Muller-Gliemann, Martin Beuck, Stanislav Kazda, Stefan Wohlfeil, Andreas Knorr, Johannes-Peter Stasch, Siegfried Zaiss
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Patent number: 5698559Abstract: Compounds of Formula I have been shown to enhance the release of the neurotransmitter acetylcholine, and thus may be useful in the treatment of diseases of man, such as in Alzheimer's disease and other conditions involving learning and cognition, where subnormal levels of this neurochemical are found.The compounds of this invention can be described as shown in Formula I ##STR1## where Q is ##STR2## R.sup.1 is 4-, 3-, or 2-pyridyl, pyrimidyl, pyrazinyl, or fluoro-4-pyridyl;R.sup.2 and R.sup.3 are independently H, F, Cl, Br, NO.sub.2, OH, --R.sup.4, --O--R.sup.4, --CO.sub.2 R.sup.4, --COR.sup.4, --CONH.sub.2, --CONHR.sup.4, --CONR.sub.4 R.sup.4', --S(O).sub.m2 --R.sup.4, NH.sub.2, CF.sub.3, NHR.sup.4, NR.sup.4 R.sup.4' ;R.sup.4 and R.sup.4' are independently H, alkyl of 1 to 4 carbons, CH.sub.2 Phe-W or Phe-W;Phe is a phenyl group;R.sup.5 is --(CH.sub.2).sub.n --Y or --OCOR.sup.4 ;Y is H, OH, NH.sub.2, NHR.sup.4, NR.sup.4 R.sup.4', NHCOR.sup.4, NHCO.sub.2 R.sup.4, NHS(O).sub.2 R.sup.4 ; F, Cl, Br, OR.sup.Type: GrantFiled: March 25, 1996Date of Patent: December 16, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Wendell Wilkie Wilkerson, Christopher Allan Teleha
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Patent number: 5696130Abstract: 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: GrantFiled: June 5, 1995Date of Patent: December 9, 1997Assignee: Ligand Pharmaceuticals IncorporatedInventors: Todd K. Jones, David T. Winn, Mark E. Goldman, Lawrence G. Hamann, Lin Zhi, Luc J. Farmer, Robert L. Davis
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Patent number: 5688803Abstract: Compounds of general formula (Ia), (Ib) and (II), wherein R.sup.1 and R.sup.2 each independently signify hydrogen, lower alkyl, lower alkoxy, nitro, trifluoromethyl, amino, halogen, cyano or R.sup.3 R.sup.4 NS(O).sub.2 -- and R.sup.3 and R.sup.4 signify lower alkyl, and R.sup.2 can additionally signify morpholino or thiomorpholino, a 5- or 6-membered heterocycle with 1-3N atoms optionally substituted by lower alkyl, hydroxy, amino or the group --CH.sub.2 NHCH.sub.3, a bicyclic heterocycle with 1-3N atoms or a group --NR.sup.5 R.sup.6 or --OR.sup.5 in which R.sup.5 and R.sup.6 can be the same or different and signify hydrogen, lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, amino-lower alkyl or lower alkylamino-lower alkyl, and X in formula (II) signifies --CH.dbd.CH--, --CH.dbd.N--, --NH--, --CO-- or --O--, as well as pharmaceutically usable salts of compounds of general formula (Ia), (Ib) and (II).Type: GrantFiled: November 15, 1996Date of Patent: November 18, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Bernd Buttelmann, Thierry Godel, Laurence Gross, Marie-Paule Heitz Neidhart, Claus Riemer, Rene Wyler
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Patent number: 5688791Abstract: 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: GrantFiled: September 11, 1995Date of Patent: November 18, 1997Assignee: UBE Industries, LTD.Inventors: Tomio Kimura, Tetsushi Katsube
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Patent number: 5643919Abstract: Compound of general formula I ##STR1## wherein A is a benzo or thieno group;R.sub.1 is (C.sub.4-6)cycloalkyl, (C.sub.4-6)cycloalkyl-(C.sub.1-5)alkyl or ##STR2## R.sup.2, m, R.sup.3, R.sup.4, R and u are defined as in the specification, and pharmaceutical preparations containing this compound and the new pharmaceutical uses thereof.Type: GrantFiled: June 7, 1995Date of Patent: July 1, 1997Assignee: Boehringer Ingelheim KGInventors: Dietrich Arndts, Walter Losel, Otto Roos
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Patent number: 5631374Abstract: The present invention is directed to derivatives of aroyl-2-quinoline-carboxaldehyde and their use in detection and quantification of minute amounts of primary amines.Type: GrantFiled: October 28, 1993Date of Patent: May 20, 1997Assignee: Research Corporation Technologies, Inc.Inventors: Milos V. Novotny, Donald Wiesler, Jinping Liu, You-Zung Hsieh
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Patent number: 5607943Abstract: A compound of formula I ##STR1## wherein A denotes a benzo, indolo or thieno group;R.sup.1 denotes thienyl or the group ##STR2## whereinR.sup.7, R.sup.8 and R.sup.9 independently of one another may represent methyl, ethyl, propyl, phenyl or benzyl, whilst not more than 2 of the substituents can simultaneously represent phenyl or benzyl;R.sup.2, m, R.sup.3 and R.sup.4 are defined as in the specification, as well as pharmaceutical preparations containing this compound and the new pharmaceutical uses thereof.Type: GrantFiled: December 21, 1994Date of Patent: March 4, 1997Assignee: Boehringer Ingelheim GmbHInventors: Walter L osel, Otto Roos, Dietrich Arndts
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Patent number: 5604235Abstract: This invention encompasses compounds of formula (I), and pharmaceutically acceptable non-toxic salts thereof wherein X and Y am the same or different and represent oxygen or H.sub.2 with the proviso that not both X and Y are H.sub.2 ; W represents phenyl, thienyl, or pyridyl, each of which may be unsubstituted or mono or disubstituted with organic or inorganic substituents; and R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are variables representing organic and inorganic substituents. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorder overdose with benzodiazepine drugs, and enhancement of memory.Type: GrantFiled: February 27, 1995Date of Patent: February 18, 1997Assignee: Neurogen CorporationInventors: Kenneth Shaw, Jun Yuan
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Patent number: 5602134Abstract: The present invention relates to novel positive inotropic and lusitropic compounds of formula ##STR1## the pharmaceutical acceptable acid addition salts thereof and the stereochemically isomeric forms thereof wherein L is a radical of formula --O-Alk-(NH).sub.p -C(.dbd.O)-R.sup.1, pharmaceutical compositions thereof, methods of preparing said compounds and intermediates in the preparation thereof.Type: GrantFiled: November 29, 1995Date of Patent: February 11, 1997Assignee: Janssen Pharmaceutica N.V.Inventors: Eddy J. E. Freyne, Alfons H. M. Raeymaekers
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Patent number: 5602142Abstract: Hypoxia selective cytotoxins having the structural formula ##STR1## wherein D, E, F and G, independently, are carbon or nitrogen, with the proviso that three or more of D, E, F and G are carbon; R.sub.1 and R.sub.2, independently, are selected from the group consisting of methyl, halo, hydro, trifluoromethyl, methoxy, cyano, and methylsulfo; R.sub.3 and R.sub.4, independently, are selected from the group consisting of methyl, ethyl, phenyl, naphthyl, tertiary butyl, halo, halomethylene, hydro, trifluoromethyl, cyano and methylsulfo, or R.sub.3 and R.sub.4 taken together are a substituted or unsubstituted five or six-membered nonaromatic ring system; n is an integer 1 through 5; X is carbon or nitrogen; and Z is a physiologically acceptable anion, are disclosed. The compounds are useful as radiosensitizers or chemosensitizers, especially in the treatment of cancer patients.Type: GrantFiled: December 21, 1994Date of Patent: February 11, 1997Assignee: Evanston Hospital CorporationInventors: Maria V. Papadopoulou-Rosenzweig, William D. Bloomer
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Patent number: 5594140Abstract: Imidazo[1,5-a]quinolines of formula (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.Type: GrantFiled: May 13, 1996Date of Patent: January 14, 1997Assignee: The Upjohn CompanyInventors: Eric J. Jacobsen, Ruth E. TenBrink
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Patent number: 5567710Abstract: 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: GrantFiled: October 13, 1994Date of Patent: October 22, 1996Assignee: SIBIA Neurosciences, Inc.Inventors: Jeffrey P. Whitten, Ian A. McDonald, Jean-Michel Vernier
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Patent number: 5563272Abstract: Novel 5,6-dihydro-4H-imidazo[4,5,1-ij]quinolines, intermediates and processes for the preparation thereof, and methods for alleviating pain utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: May 31, 1995Date of Patent: October 8, 1996Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Edward J. Glamkowski, Brian S. Freed
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Patent number: 5532249Abstract: Compounds of Formula I have been shown to enhance the release of the neurotransmitter acetylcholine, and thus may be useful in the treatment of diseases of man, such as in Alzheimer's disease and other conditions involving learning and cognition, where subnormal levels of this neurochemical are found.The compounds of this invention can be described as shown in Formula I ##STR1## where Q is ##STR2## R.sup.1 is 4-,3-, or 2-pyridyl, pyrimidyl, pyrazinyl, or fluoro-4-pyridyl; R.sup.2 and R.sup.3 are independently H, F, Cl, Br, NO.sub.2, OH, --R.sup.4, --O--R.sup.4, --CO.sub.2 R.sup.4, --COR.sup.4, --CONH.sub.2, --CONHR.sup.4, --CONR.sup.4 R.sup.4', --S(O).sub.m2 -- R.sup.4, NH.sub.2, CF.sub.3, NHR.sup.4, NR.sup.4 R.sup.4' ;R.sup.4 and R.sup.4' are independently H, alkyl of 1 to 4 carbons, CH.sub.2 Phe-W or Phe-W;and hydrates and physiologically suitable salts thereof.Type: GrantFiled: September 26, 1994Date of Patent: July 2, 1996Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Wendell W. Wilkerson, Christopher A. Teleha
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Patent number: 5500423Abstract: Novel 5,6-dihydro-4H-imidazo[4,5,1-ij]quinolines, intermediates and processes for the preparation thereof, and methods for alleviating pain utilizing compounds or compositions thereof are disclosed.Type: GrantFiled: September 9, 1994Date of Patent: March 19, 1996Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Edward J. Glamkowski, Brian S. Freed
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Patent number: 5461061Abstract: A compound of Formula I ##STR1## or pharmaceutically acceptable salts of Formula I, where R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, --(CH.sub.2).sub.n CONH.sub.2 where n is 2 to 6, (CH2).sub.n -1-(4,4-dimethylpiperidine-2,6-dione-yl), or cyclopropylmethyl;R.sup.2 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl or combined with R.sup.1 to form a C.sub.3 -C.sub.8 cycloalkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 akynyl, (CH.sub.2).sub.n --X--Ar where X is O, S, or NH, 3,3,3-trifluoropropyl, --(CH.sub.2).sub.m --R.sup.9 where m is 2 or 3 and R.sup.9 is phenyl, 2-thiophenyl or 3-thiophenyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, formyl, CN, halogen, CH.sub.2 OR.sup.2, C(O)C(O)OR.sup.1, C(O)CO NR.sup.1 R.sup.2, --(CH.sub.2).sub.q --NR.sup.1 R.sup.2 where q is 0 to 5, C.dbd.NOR.sup.2, 2(4,5-dihydro)oxazolyl, or COR.sup.10 where R.sup.10 is H, R.sup.1, NR.sup.1 R.sup.2 or CF.sub.3 ; R.sup.4 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: October 28, 1993Date of Patent: October 24, 1995Inventors: Hakan V. Wikstrom, Per A. E. Carlsson, Bengt R. Andersson, Kjell A. I. Svensson, Stig T. Elebring, Nils P. Stjernlof, Arthur G. Romero, Susanne R. Haadsma-Svensson, Chiu-Hong Lin, Michael D. Ennis
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Patent number: 5439916Abstract: 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: GrantFiled: August 31, 1990Date of Patent: August 8, 1995Assignee: Schering CorporationInventors: Ashit K. Ganguly, Richard J. Friary, John H. Schwerdt, Marvin I. Siegel, Sidney R. Smith, Edmund J. Sybertz
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Patent number: 5436250Abstract: 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 C.sub.1-6 -alkyl which may be straight, branched or cyclic,R.sup.2 is hydrogen or C.sub.1-6 -alkyl which may be straight, 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;R.sup.II is hydrogen, benzyl, (C.dbd.O)CF.sub.3, 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 straight, branched or cyclic, CH.sub.2 CO.sub.2 R.sup.VI wherein R.sup.VI is hydrogen or C.sub.Type: GrantFiled: July 7, 1993Date of Patent: July 25, 1995Assignee: NeuroSearch A/SInventors: Frank Watjen, Bjarne H. Dahl, Jorgen Drejer, Lein H. Jensen
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Patent number: 5414001Abstract: The invention discloses certain antitumor pyrrolo[4,3,2-de]quinolin-8(1H)-ones isolated from the Fijian marine sponge Z. cf. marsailis and structurally modified compounds thereof and pharmaceutical compositions.Type: GrantFiled: April 16, 1993Date of Patent: May 9, 1995Assignee: American Cyanamid CompanyInventors: Chris M. Ireland, Derek C. Radisky, Louis R. Barrows, Robert Kramer
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Patent number: 5391762Abstract: The compounds of the formula I ##STR1## in which Y and Y.sub.1 are each, independently of one another, O, S, NH or N-alkyl, N-cycloalkyl, N-phenyl or N-benzyl, or Y and Y.sub.1 are together N-alkylene-N,R and R.sub.1 are each, independently of one another, H, alkyl, cycloalkyl, aralkyl or aryl,R.sub.2 and R.sub.3 are each, independently of one another, H, or R.sub.2 forms, together with R.sub.6 and the N and C atoms linking them, a 5- or 6-membered ring and R.sub.3 is H, or R.sub.3 forms, together with R.sub.7 and the N and C atoms linking them, a 5- or 6-membered ring and R.sub.2 is H,R.sub.4 and R.sub.5 are each, independently of one another, H, R.sub.4 forms, together with R.sub.8 and the N and C atoms linking them, a 5- or 6-membered ring and R.sub.5 is H, or R.sub.5 forms, together with R.sub.9 and the N and C atoms linking them, a 5- or 6-membered ring and R.sub.4 is H,R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are each, independently of one another, H, alkyl, cycloalkyl, aralkyl or aryl, or R.sub.6 and R.Type: GrantFiled: September 14, 1993Date of Patent: February 21, 1995Assignee: Ciba-Geigy CorporationInventors: Rudolf Naef, Beat Schmidhalter, Hanspeter Preiswerk
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Patent number: 5360799Abstract: Compounds of formula ##STR1## in which R.sub.1 represents OH, (C.sub.1 -C.sub.12)alkyl, (C.sub.1 -C.sub.12)alkoxy, benzyloxy, benzyl, phenyl, (C.sub.1 -C.sub.4)alkylNZ.sub.1 Z.sub.2 or NZ.sub.1 Z.sub.2 ; R.sub.2 represents OH, SH, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.4)alkylthio or NZ.sub.1 Z.sub.2 ; R.sub.3 represents H, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkylthio, (C.sub.1 -C.sub.4)alkoxy, phenyl or benzyl; A represents N and R represents H or (C.sub.1 -C.sub.4)alkyl which can be substituted by phenyl or NZ.sub.1 Z.sub.2 ; B represents phenyl which is coupled to the pyridyl ring and is optionally substituted by one or more groups chosen from halo, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, CF.sub.3, CH.sub.2 NZ.sub.1 Z.sub.2 or NZ.sub.1 Z.sub.2 ; and Z.sub.1 and Z.sub.2 represent, independently of each other, H, (C.sub.1 -C.sub.6) alkyl, formyl or benzyl, or they form with the nitrogen atom to which they are attached an optionally substituted saturated heterocycle and their salts.Type: GrantFiled: August 19, 1993Date of Patent: November 1, 1994Assignee: Elf SanofiInventors: Andre Bachy, Laurent Fraisse, Peter Keane, Etienne Mendes, Jean-Claude Vernieres, Jacques Simiand
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Patent number: 5332740Abstract: Novel DC-89 derivatives represented by general formula (I): ##STR1## wherein X represents Cl or Br; R.sup.1 represents hydrogen, CONR.sup.2 R.sup.3 (in which R.sup.2 and R.sup.3 independently represent hydrogen, a straight-chain or branched alkyl group having 1 to 4 carbon atoms or phenyl group), ##STR2## (in which n represents an integer of 4 to 7), ##STR3## (in which R.sup.4 represents oxygen, N--CH.sub.3 or N--CH.sub.2 CH.sub.2 NH.sub.2), ##STR4## (in which R.sup.5 R.sup.6 and R.sup.7 independently represent a straight-chain or branched alkyl group having 1 to 4 carbon atoms); and ##STR5## (in which Y represents hydrogen or CO.sub.2 CH.sub.3); provided that when R.sup.1 is hydrogen, CONR.sup.2 R.sup.3 or SiR.sup.5 R.sup.6 R.sup.7, ##STR6## and pharmaceutically acceptable salts thereof have an excellent anti-tumor activity and are expected to be useful as anti-tumor compositions.Type: GrantFiled: April 13, 1993Date of Patent: July 26, 1994Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hiromitsu Saito, Satoru Nagamura, Akira Asai, Eiji Kobayashi, Katsushige Gomi
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Patent number: 5326768Abstract: The present invention concerns 3,4-annelated benzimidazol-2(1H)-one 1-carboxylic acid derivatives of the formula ##STR1## wherein R.sub.0, Z, A, B and C are as defined herein. Such derivatives are useful in the treatment of symptoms which are caused by over-excitation of 5-hydroxytryptamine receptors.Type: GrantFiled: September 28, 1992Date of Patent: July 5, 1994Assignee: Duphar International Research B.V.Inventors: Ineke Van Wijngaarden, Derk Hamminga, Wouter Wouters
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Patent number: 5288725Abstract: A pyrroloquinoline compound of the following formula is disclosed: ##STR1## wherein H,C.sub.1-6 alkyl,R.sup.1 is: ##STR2## wherein R is H, C.sub.1-10 alkyl, or C.sub.1-6 alkyloxycarbonyl; R.sup.2 is:H,C.sub.1-6 alkyl, ##STR3## wherein R.sup.5 is C.sub.1-10 alkyl, aryl, or aryl C.sub.1-10 alkyl; R.sup.3 is:(CH.sub.2).sub.n NHR wherein R is H, C.sub.1-6 alkyl, or C.sub.1-6 alkyloxycarbonyl; ##STR4## R.sup.4 is: H,C.sub.1-6 alkyl,C.sub.1-6 alkyloxycarbonyl,RCH.sub.2 --, wherein R is H, C.sub.1-6 alkyl or aryl, or ##STR5## X is O, or NR.sup.6 wherein R.sup.6 is equal to H or C.sub.1-6 alkyl and n is an integer from 1-3.The compounds of the invention exhibit bradykinin antagonist activity as well as activity with .alpha.-adrenergic, histaminergic, and muscarinic receptors.Type: GrantFiled: October 15, 1992Date of Patent: February 22, 1994Assignee: Merck & Co., Inc.Inventors: Keith M. Witherup, Richard W. Ransom, Sandor L. Varga, Steven M. Pitzenberger, Victor J. Lotti, William J. Lumma
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Patent number: RE35840Abstract: The present invention is to imidazo?1,5-a!quinolines (I) which are useful pharmaceutical agents for the treatment of anxiety, sleep disorders, panic states, convulsions and muscle disorders.Type: GrantFiled: June 17, 1997Date of Patent: July 7, 1998Assignee: Pharmacia & Upjohn CompanyInventors: Eric Jon Jacobsen, Ruth Elizabeth TenBrink