Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/289)
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Patent number: 6632945Abstract: The present invention relates to inhibitors of p38, a mammalian protein kinase involved cell proliferation, cell death and response to extracellular stimuli. The invention also relates to methods for producing these inhibitors. The invention also provides pharmaceutical compositions comprising the inhibitors of the invention and methods of utilizing those compositions in the treatment and prevention of various disorders.Type: GrantFiled: December 21, 2000Date of Patent: October 14, 2003Assignee: Vertex Pharmaceuticals IncorporatedInventors: Francesco Salituro, Vincent Galullo, Steven Bellon, Guy Bemis, John Cochran
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Patent number: 6632823Abstract: In accordance with the present invention, a novel class of substituted pyridine compounds (optionally containing ether, ester, amide, ketone or thioether substitutions) that promote the release of ligands involved in neurotransmission have been discovered. In a particular aspect compounds of the present invention are capable of modulating acetylcholine receptors. The compounds of the present invention are capable of modulating acetylcholine receptors. Invention compounds may act as agonists, partial agonists, antagonists or allosteric modulators of acetylcholine receptors.Type: GrantFiled: December 22, 1997Date of Patent: October 14, 2003Assignee: Merck & Co., Inc.Inventors: Jean-Michel Vernier, Nicholas D. P. Cosford, Ian A. McDonald
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Publication number: 20030119881Abstract: Compounds of the formula I: 1Type: ApplicationFiled: September 12, 2002Publication date: June 26, 2003Applicant: Medivir ABInventors: Christer Salhberg, Rolf Noreen, Marita Hogberg, Per Engelhardt
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Patent number: 6583161Abstract: The invention provides compounds, compositions and methods relating to novel aromatic derivatives and their use as pharmacologically active agents. The compositions find particular use as pharmacological agents in the treatment of disease states, particularly cancer, psoriasis, vascular restenosis, infections, atherosclerosis and hypercholesterolemia, or as lead compounds for the development of such agents.Type: GrantFiled: December 12, 2000Date of Patent: June 24, 2003Assignee: Tularik Inc.Inventor: Julio C. Medina
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Patent number: 6537999Abstract: This invention discloses pyrimidine derivatives, and pharmaceutically acceptable salts and prodrugs thereof, of the following formula: wherein L and M are selected from the group consisting of carbon and CH, the chemical bond between L and M is selected from the group consisting of a single bond and a double bond, wherein Z4 and Z5 are different and are selected from the group consisting of R14 and where Z4 is R14 when Z5 is and Z4 is when Z5 is R14; wherein A1 is CH; wherein B1 is CH; wherein R17 is selected from the group consisting of aryl, diaryl, triaryl, mono-, di- or tri-substituted aryl, mono-, di- or tri-substituted diaryl, mono-, di- or tri- substituted triaryl, a substituted or unsubstituted heteroaryl and p-aroyl-L-glutamate; wherein R18 is a lower akyl group; and said compound capable of inhibiting dihydrofolate reductase and thymidylate synthase.Type: GrantFiled: March 9, 2001Date of Patent: March 25, 2003Assignee: Duquesne University of the Holy GhostInventor: Aleem Gangjee
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Patent number: 6486183Abstract: Compounds of formula (I): wherein Rx is cyano or bromo; R1 is halo; R2 is C1-C3 alkyl, and pharmaceutically acceptable salts and prodrugs thereof have activity as antiretrovirals.Type: GrantFiled: November 13, 2000Date of Patent: November 26, 2002Assignee: Medivir ABInventors: Christer Salhberg, Rolf Noréen, Marita Högberg, Per Engelhardt
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Publication number: 20020165412Abstract: N-(Aryl)-2-arylethenesulfonamides and pharmaceutically acceptable salts and compositions thereof are useful as antiproliferative agents, including, for example, anticancer agents. They are also useful as radioprotective agents.Type: ApplicationFiled: February 28, 2002Publication date: November 7, 2002Inventors: E. Premkumar Reddy, M.V. Ramana Reddy, Stanley C. Bell
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Publication number: 20020072500Abstract: The present invention relates to a class of compounds represented by the Formula I.Type: ApplicationFiled: September 26, 2001Publication date: June 13, 2002Inventors: Thomas Rogers, Thomas D. Penning, Lan Jiang, Balekudru Devadas, Peter Ruminiski, Jennifer VanCamp, Chester Yuan
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Patent number: 6372907Abstract: The present invention provides novel, water-soluble, red-emitting fluorescent rhodamine dyes and red-emitting fluorescent energy-transfer dye pairs, as well as labeled conjugates comprising the same and methods for their use. The dyes, energy-transfer dye pairs and labeled conjugates are useful in a variety of aqueous-based applications, particularly in assays involving staining of cells, protein binding, and/or analysis of nucleic acids, such as hybridization assays and nucleic acid sequencing.Type: GrantFiled: September 14, 2000Date of Patent: April 16, 2002Assignee: Apptera CorporationInventors: Linda G. Lee, Ronald J. Graham, William E. Werner, Elana Swartzman, Lily Lu
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Patent number: 6191278Abstract: The present invention provides novel, water-soluble, red-emitting fluorescent rhodamine dyes and red-emitting fluorescent energy-transfer dye pairs, as well as labeled conjugates comprising the same and methods for their use. The dyes, energy-transfer dye pairs and labeled conjugates are useful in a variety of aqueous-based applications, particularly in assays involving staining of cells, protein binding, and/or analysis of nucleic acids, such as hybridization assays and nucleic acid sequencing.Type: GrantFiled: November 3, 1999Date of Patent: February 20, 2001Assignee: PE CorporationInventors: Linda G. Lee, Ronald J. Graham, William E. Werner, Elana Swartzman, Lily Lu
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Patent number: 6130226Abstract: Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor .alpha., nuclear factor .kappa.B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.Type: GrantFiled: March 18, 1999Date of Patent: October 10, 2000Assignee: Celgene CorporationInventors: George W. Muller, Mary Shire
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Patent number: 6107299Abstract: Compounds of formula I, N-oxides or salts, thereof ##STR1## in which q is 0, 1 or 2A is CH and D is N.sup.+ R.times.1/n Q.sup.n- or A is N and D is N.sup.+ R.times.1/n Q.sup.n- or A is CH or N and D is Nor A is N.sup.+ R.times.1/n Q.sup.n- and D is N, R is CR.sup.6 R.sup.7 D.sup.a R.sup.8,Q.sup.n- is an inorganic or organic anion, n being 1, 2, 3 or 4;X is NH, O or S(O).sub.q, (q is 0, 1 or 2); and the R groups have various meanings as defined in the claims are useful pesticidal, especially insecticidal activity.Type: GrantFiled: May 18, 1999Date of Patent: August 22, 2000Assignee: Hoechst Schering AgrEvo GmbHInventors: Harald Jakobi, Matthias Eckhardt, Wolfgang Schaper, Ralf Braun, Gerhard Krautstrunk, Oswald Ort, Ulrich Sanft, Maria-Theresia Thonessen, Werner Bonin
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Patent number: 6022884Abstract: Selected novel substituted pyridine compounds are effective for prophylaxis and treatment of diseases, such as TNF-.alpha., IL-1.beta., IL-6 and/or IL-8 mediated diseases, and other maladies, such as pain and diabetes. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving inflammation, pain, diabetes, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.Type: GrantFiled: November 3, 1998Date of Patent: February 8, 2000Assignee: Amgen Inc.Inventors: Nathan B. Mantlo, Stephen T. Schlachter, John A. Josey
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Patent number: 5972975Abstract: Substituted 2-aminopyridine compounds of Formula (I) and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders.Type: GrantFiled: May 22, 1997Date of Patent: October 26, 1999Assignee: Merck & Co., Inc.Inventors: Craig Esser, William Hagmann, William Hoffman, Shrenik Shah, Kenny Wong, Renee Chabin, Ravindra Guthikonda, Malcolm Maccoss, Charles Caldwell, Philippe Durette
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Patent number: 5925596Abstract: Substituted aminomethylphenylsulfonylureas, their preparation, and their use as herbicides and plant growth regulatorsCompounds of the formula (I) and salts thereof ##STR1## where R.sup.1 to R.sup.7 and A are as defined in claim 1 and, inter alia, F.sup.5 is an acyl radical or NR.sup.4 R.sup.5 together are a heterocyclic radical, are useful as herbicides and plant growth regulators. They can be prepared by the methods of known processes, using novel intermediates of the formula (II), (IV), (VI) or (VII) (cf. claim 5).Type: GrantFiled: April 24, 1997Date of Patent: July 20, 1999Assignee: Hoechst-Schering AgrEvo GmbHInventors: Klaus Lorenz, Lothar Willms, Klaus Bauer, Hermann Bieringer, Christopher Rosinger
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Patent number: 5852042Abstract: The invention relates to novel substituted N-(4-pyridyl)carboxamides of the formula ##STR1## in which Q is substituted 4-pyridyl, A is hydrogen, alkyl, acyl or aralkyl and Y-Z is an optionally modified hydrocarbon radical or Y is a bond or a bivalent radical and Z is aryl, O-aryl, cycloalkyl, cycloalkenyl or heterocyclyl, all of which are optionally substituted, to processes for their preparation, to intermediates during their preparation, and to their use as pesticides, in particular as insecticides, acaricides and nematicides, and also as fungicides.Type: GrantFiled: September 26, 1995Date of Patent: December 22, 1998Assignee: Hoechst Schering AgrEvo GmbHInventors: Harald Jakobi, Werner Knauf, Ulrich Sanft, Manfred Kern, Dieter Bernd Reuschling, Adolf Heinz Linkies, Werner Bonin
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Patent number: 5763638Abstract: A process for the preparation of nitriles of formula ##STR1## wherein X is CH or N, and R.sub.1 and R.sub.2 are each independently of the other hydrogen, chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, CN, phenyl, phenoxy, dimethylamino, piperidyl, morpholinyl or pyrrolidyl, or R.sub.1 and R.sub.2 together form a fused benzene ring, by reacting an aldehyde of formula ##STR2## with hydroxylaminosulfate in the presence of a tertiary amine base of formula ##STR3## wherein R.sub.3 and R.sub.4 are each independently of the other hydrogen, methyl or ethyl, R.sub.5 is branched C.sub.3 -C.sub.5 alkyl or phenyl, and R.sub.6 and R.sub.7 are methyl or ethyl,in the temperature range from 100.degree. to 160.degree. C., while distilling the released water of reaction off concomittantly at a pressure in the range of 0.02 to 1.5 bar, with subsequent removal of the ammonium salts, and isolating the nitrile so obtained by customary methods.Type: GrantFiled: February 4, 1997Date of Patent: June 9, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Richard Breitschuh
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Patent number: 5760063Abstract: The subject invention, provides arylhydrazone compounds having the Formula 1: ##STR1## wherein A and B are independently aryl or heteroaryl and A and B independently are substituted with at least one group selected from alkyl, halogen, CN, COOR.sup.7, NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, NO.sub.2, SR.sup.7, SOR.sup.7, SO.sub.2 R.sup.7, NHCOR.sup.7, NHSO.sub.2 R.sup.7, OR.sup.7, hydroxyalkyl, and aminoalkyl. The compounds of this invention are useful for treating a wide variety of bacterial infections, including diseases of the skin, e.g., acne and skin ulcers, gastroenteritis, colitis, meningitis, keratinitis, conjunctivitis, diseases of the urinary and genital tracts, etc.Type: GrantFiled: September 13, 1996Date of Patent: June 2, 1998Assignee: Scriptgen Pharmaceuticals, Inc.Inventors: Kelvin T. Lam, David G. Powers
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Patent number: 5756524Abstract: A compound of formula I ##STR1## X is O or S; A is 6-alkoxy-3-pyridyl optionally substituted by halogen;Y is hydrogen or alkyl;R.sup.3 is alkyl or a metal salt complex thereof. This invention contains fungicidal compositions and are used to combat cytopathogenic fungi.Type: GrantFiled: September 18, 1996Date of Patent: May 26, 1998Assignee: Agrevo UK LimitedInventors: Peter Dominic Riordan, Susan Elizabeth Osbourn, Ian Kenneth Boddy
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Patent number: 5716971Abstract: Pyridine derivatives of the formula ##STR1## wherein the ring A stands for an optionally further substituted benzene ring; the ring B stands for an optionally substituted pyridine ring; Q stands for hydroxyl group, or OQ.sup.1 or Q.sup.1 wherein Q.sup.1 stands for an optionally substituted aliphatic hydrocarbon group; and n denotes 0 or 1, or their salts, which have potassium.channel opening activity and are useful as therapeutic agents of circulatory diseases such as angina pectoris, hypertension, etc.Type: GrantFiled: August 9, 1996Date of Patent: February 10, 1998Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Toshifumi Watanabe
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Patent number: 5696140Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for ##STR1## where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice for treating asthma, allergy, CNS disorders, or cancer.Type: GrantFiled: October 3, 1996Date of Patent: December 9, 1997Assignee: Leo Pharmaceutical Products Ltd.Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5670525Abstract: The application relates to substituted 4-phenyl-6-amino-nicotinic acid derivatives for therapeutic use, to novel active compounds and to their use as cerebrally active agents. The active compounds are prepared by oxidizing appropriately substituted dihydropyridines according to customary methods.Type: GrantFiled: August 22, 1995Date of Patent: September 23, 1997Assignee: Bayer AktiengesellschaftInventors: Klaus Urbahns, Siegfried Goldmann, Hans-Georg Heine, Bodo Junge, Rudolf Schohe-Loop, Henning Sommermeyer, Thomas Glaser, Reilinde Wittka, Jean-Marie Viktor De Vry
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Patent number: 5654429Abstract: A process for the preparation of a 3-amino-2-chloro-4-alkylpyridine of the formula: ##STR1## wherein R1 is a linear, branched or cyclic hydrocarbon of from one to eight carbon atoms, optionally substituted with one or more electron stabilizing groups,an intermediate in the preparation of certain 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine compounds useful in the prevention and treatment of HIV infection.Type: GrantFiled: June 7, 1995Date of Patent: August 5, 1997Inventor: Laurence John Nummy
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Patent number: 5654321Abstract: The present invention relates to a novel 2-chloro-3-arylamino-1,4-naphthoquinone derivative represented by the following formula (I), which has a potent inhibitory activity against platelet aggregation: ##STR1## in which X represents nitrogen (N) or carbon (C) atom andR represents cyano, orR can further represent alkyl, carboxyl or acyl when X represents nitrogen (N) atom,and to a process for preparing thereof and to a pharmaceutical composition for inhibiting blood coagulation which comprises the compound of formula (I) as an active ingredient.Type: GrantFiled: January 30, 1996Date of Patent: August 5, 1997Assignee: Dong Kook Pharmaceutical Co. Ltd.Inventors: Chang-Kiu Moon, Chung-Kyu Ryu
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Patent number: 5652251Abstract: The present invention relates to the new use of 6-amino-5-nitro- and -5-cyano-1,4-dihydropyridines of the general formula (I) ##STR1## in which A, D and R.sup.1 -R.sup.4 have the meaning given in the description, new 6-acylamino-dihydropyridines, processes for their preparation and their use as medicaments as selective potassium channel modulators, in particular for treatment of the central nervous system.Type: GrantFiled: August 18, 1995Date of Patent: July 29, 1997Assignee: Bayer AktiengesellschaftInventors: Klaus Urbahns, Siegfried Goldmann, Hans-Georg Heine, Bodo Junge, Rudolf Schohe-Loop, Henning Sommermeyer, Thomas Glaser, Reilinde Wittka, Jean-Marie-Viktor De Vry
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Patent number: 5631381Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.Type: GrantFiled: June 28, 1996Date of Patent: May 20, 1997Assignee: Rhone-Poulenc Inc.Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
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Patent number: 5604230Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1) compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifluoromethyl; R.sup.4 is trifluoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical --Alk--R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy; Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.Type: GrantFiled: May 2, 1995Date of Patent: February 18, 1997Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5587387Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1)compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifiuoromethyl; R.sup.4 is trifiuoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical -Alk-R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy; Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.Type: GrantFiled: May 2, 1995Date of Patent: December 24, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5569765Abstract: A process for controlling pests in which the pests or the plants threatened by attack with pests are treated with a 2-anilinopyridine of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, substituted cycloalkyl, alkoxy, haloalkoxy, substituted alkyl, alkenyloxy, alkynyloxy, halogen, CN, SCN, formyl, CH.dbd.NOR.sub.5, CH.dbd.NR.sub.6, CH.sub.2 NHR.sub.6R.sup.5 is hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, COR.sup.7 or unsubstituted or substituted phenyl,R.sup.6 is hydrogen, alkyl, unsubstituted or substituted cycloalkyl, alkenyl, alkynyl or unsubstituted or substituted phenyl,R.sup.2 is alkyl, alkenyl, alkynyl, haloalkyl or cycloalkylR.sup.3 is hydrogen, CN, S(O).sub.n R.sup.8 or COR.sup.9,R.sup.8 is alkyl or substituted phenyl,R.sup.9 is hydrogen, alkyl, haloalkyl, cycloalkyl, phenyl or benzyl,R.sup.Type: GrantFiled: April 17, 1995Date of Patent: October 29, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5563160Abstract: The present invention relates to hitherto unknown compounds of formula or their tautomeric forms, the attachment to the pyridine ring being in the 3- or 4-position, in which R', R" are the same or different and stand for hydrogen, halogen, or trifluoromethyl, hydroxy, C.sub.1 -C.sub.4 alkyl or alkoxy, nitro, or cyano groups. Alkylene stands for a straight or branched C.sub.1 -C.sub.8 carbon chain, which may be substituted by hydroxy or halogen, nitro or cyano groups. X stands for oxygen, for --S(O).sub.n -- where n stands for an integer from 0 to 2, or for .dbd.N--R.sub.1 where R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl. R stands for hydrogen or for one or more C.sub.1 -C.sub.4 alkyl or alkoxy, hydroxy, halogen, trifluoromethyl, cyano, carboxamido, sulfamoyl or nitro radicals. The present compounds are of value in the human and veterinary practice as selective serotonin receptor antagonists.Type: GrantFiled: March 15, 1995Date of Patent: October 8, 1996Assignee: Leo Pharmaceutical Products Ltd. A/S (L.o slashed.vens Kemiske Fabrik Produktionsaktieselskab)Inventors: Erik Bramm, Hans J.o slashed.rgen Petersen
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Patent number: 5550135Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1) compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifluoromethyl; R.sup.4 is trifluoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical -Alk-R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy;Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.Type: GrantFiled: May 2, 1995Date of Patent: August 27, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5536840Abstract: A process for preparing diaminopyridines of the formula ##STR1## where one of the two radicals X.sup.1 and X.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or nitro and the other is cyano,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, andR.sup.5 is optionally substituted C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.5 -C.sub.7 -cycloalkyl,by reacting dichloropyridines of the formula ##STR2## in a first step with an amine of the formula R.sup.5 -NH.sub.2 at from 10.degree. to 80.degree. C. in the presence of a base and of an inert organic diluent and/or water, then removing the diluent and thereafter, with or without prior intermediate isolation of the reaction product, comprises carrying out the second step in a melt at from 90.degree. to 165.degree. C. and at a pH from 3.5 to 6.5 using from 1.Type: GrantFiled: June 17, 1994Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Gunther Lamm, Hermann Loeffler, Helmut Reichelt
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Patent number: 5534528Abstract: The present invention relates to therapeutically active azacyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrain and hippocampus of mammals and especially in the treatment of Alzheimer's disease, severe painful conditions and glaucoma.Type: GrantFiled: June 7, 1995Date of Patent: July 9, 1996Assignee: Novo Nordisk A/SInventors: Per Sauerberg, Preben H. Olesen
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Patent number: 5532245Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, straight or branched chain alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2## wherein R.sub.9 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, mono- or dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano, carboxyl, chloro, bromo, fluoro or iodo; n is an integer from 0 to 6; R.sub.3 and R.sub.4, independent from each other, are hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, perfluoroalkyl, hydroxyalkyl, alkoxyalkyl, fluoro, or, when taken together, form a spirocyclic ring; R.sub.5 and R.sub.Type: GrantFiled: June 7, 1995Date of Patent: July 2, 1996Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane, Bradford H. Hirth
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Patent number: 5516786Abstract: Combating fungi with substituted amine acid derivatives of the formula ##STR1## in which R.sup.1 represents alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cycloalkyl or cycloalkenyl,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen, cycloalkyl or alkyl, orR.sup.3 and R.sup.4, together with the carbon atom to which they are bonded, form a cycloalkyl ring, andR.sup.6 represents hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, unsubstituted or substituted phenylalkyl, unsubstituted or substituted phenyl or unsubstituted or substituted cycloalkyl, or represents unsubstituted or substituted heterocyclyl or heterocyclylalkyl,orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a heterocyclyl radical, which can contain further hetero atoms.Type: GrantFiled: November 21, 1994Date of Patent: May 14, 1996Assignee: Bayer AktiengesellschaftInventors: Detlef Wollweber, Thomas Seitz, Wilhelm Brandes
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Patent number: 5512585Abstract: The compound of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are, independent from each other, hydrogen, C.sub.1-10 straight chain alkyl, C.sub.1-10 branched alkyl, or C.sub.3-10 cyclic or bicyclic alkyl;R.sub.3 is an acyl substituent selected from the group consisting of formyl, alkanoyl of 2 to 7 carbon atoms, alkenoyl of 3 to 7 carbon atoms, alkylsulfonyl of 1 to 7 carbon atoms, aroyl of 7 to 12 carbon atoms, arylalkenoyl of 9 to 20 carbon atoms, arylsulfonyl of 6 to 12 carbon atoms, arylalkanoyl of 8 to 12 carbon atoms or arylalkylsulfonyl of 7 to 12 carbon atoms;A is selected from the group consisting of: ##STR2## wherein: R.sub.4 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkoxy, C.sub.1-6 perfluoroalkoxy, amino, C.sub.1-6 alkylamino, C.sub.2-12 dialkylamino, C.sub.1-6 alkylsulfonamido, alkylcarboxamido containing 2 to 7 carbon atoms, nitro, cyano or carboxyl;or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: June 2, 1995Date of Patent: April 30, 1996Assignee: American Home Products CorporationInventors: Madelene M. Antane, John A. Butera, Bradford H. Hirth, Schuyler A. Antane
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Patent number: 5480995Abstract: 6-Amino-nicotinonitriles of the formula ##STR1## can be prepared by reacting methylene-glutacononitriles of the formula ##STR2## with nitrogen compounds of the formulaR.sup.1 --NH.sub.2 (III)at 0.degree. to 200.degree. C. in the presence or absence of an inert solvent. The ratio of nitrogen compound to glutacononitrile is 1 to 100:1. The substituents R.sup.1 and R.sup.4 have the meanings given in the description.Type: GrantFiled: January 11, 1994Date of Patent: January 2, 1996Assignee: Bayer AktiengesellschaftInventor: Helmut Kraus
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Patent number: 5480997Type: GrantFiled: May 12, 1994Date of Patent: January 2, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5478944Abstract: 2-Amino-5-aminomethyl-pyridine, of the formula ##STR1## can be prepared by reacting substituted methylene-glutaconic acid dinitrile of the formula ##STR2## having the meaning of R.sup.1 as given in the general description, at from 50.degree. to 200.degree. C., initially with from 3 to 20 mol of ammonia and then, in the presence of a hydrogenation catalyst, with hydrogen. The hydrogen is present an a partial pressure of from 10 to 250 bar. The reaction can be carried out with or without solvent.Type: GrantFiled: January 11, 1994Date of Patent: December 26, 1995Assignee: Bayer AktiengesellschaftInventor: Helmut Kraus
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Patent number: 5459148Abstract: Compounds of formula (I): ##STR1## [wherein: A represents a group (IIa), (IIb) or (IIc): ##STR2## R.sup.1 is alkyl, alkenyl, cycloalkyl or a group of formula R.sup.4 --Y--R.sup.5 --, where: R.sup.4 is hydrogen, alkyl, or cycloalkyl, R.sup.5 is a single bond or alkylene, and Y is oxygen, sulfur or imino group; R.sup.2 is hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, hydroxy, amino, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkoxy, alkylthio, cyano or nitro; R.sup.3 is hydrogen, alkyl, carboxy, protected carboxy, carbamoyl or tetrazol-5-yl; X is of formula --CH.dbd., --N.dbd. or --C(COOR.sup.6).dbd., where R.sup.Type: GrantFiled: October 27, 1994Date of Patent: October 17, 1995Assignee: Sankyo Company, LimitedInventors: Hiroaki Yanagisawa, Yoshiya Amemiya, Takuro Kanazaki, Yasuo Shimoji, Hiroyuki Koike, Toshio Sada
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Patent number: 5438065Abstract: Diaminoethylene derivatives of the formula: ##STR1## wherein R.sup.1 is a heterocyclic group which may be substituted, R.sup.2, R.sup.3 and R.sup.4 are a hydrogen atom or a hydrocarbon group which may be substituted or R.sup.3 and R.sup.4 are combined to form a cyclic amino group together with the adjacent nitrogen atom; R.sup.5 is hydrogen atom or a hydrocarbon group or heterocyclic group which may be substituted; X is an electron attractive group; Y is a hydroxyl or substituted hydroxyl group, amino or substituted amino group or mercapto or substituted mercapto group; n is 0 or 1; or their salts, which are useful as insecticides.Type: GrantFiled: April 12, 1990Date of Patent: August 1, 1995Assignee: Takeda Chemical IndustriesInventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi
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Patent number: 5432282Abstract: The present invention relates to new 2-amino-5-cyano-4-quinoline-1,4-dihydropyridines, processes for their preparation and their use in medicaments, in particular in agents for the treatment of cardiovascular diseases.Type: GrantFiled: August 30, 1994Date of Patent: July 11, 1995Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Siegfried Goldmann, Alexander Straub, Horst Boshagen, Martin Bechem, Rainer Gross, Siegbert Hebisch, Joachim Hutter, Howard-Paul Rounding
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Patent number: 5418245Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: March 17, 1994Date of Patent: May 23, 1995Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.Inventors: Alfred P. Spada, Paul E. Persons
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Patent number: 5354763Abstract: The compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is an N-heterocycle which may be substituted by alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano or carboxyl;or, A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl;or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: November 17, 1993Date of Patent: October 11, 1994Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane
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Patent number: 5354500Abstract: Use of optically active carboxylic esters of oxygen-containing heterocycles as doping substances in liquid crystal mixtures and liquid crystal mixtures containing them.Optically active 1,3-dioxolane-4-carboxylic esters and oxirane-2-carboxylic esters of the general formula (I)R(--A.sup.1).sub.j (--M.sup.1).sub.k (--A.sup.2).sub.l (--M.sup.2).sub.m (--A.sup.3).sub.n --X--Acin whichR.sup.1 is, for example, (C.sub.1 -C.sub.16)-alkyl or (C.sub.1 -C.sub.16)-alkoxy,A.sup.1, A.sup.2, A.sup.3 are, for example, phenyl or pyrimidine-2, 5-diyl,M.sup.1, M.sup.2 are, for example, CO--O, CH.sub.2 --CH.sub.2,j, l are 0, 1, 2,k, m are 0, 1,n is 0, 1, 2,X is O, S andAc is ##STR1## in which R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 for example, H or methyl, are particularly suitable doping substances for liquid crystalline mixtures, since they induce a high spontaneous polarization and effect a substantial decrease in the melting point.Type: GrantFiled: April 17, 1992Date of Patent: October 11, 1994Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hemmerling, Ingrid Muller, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
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Patent number: 5346912Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein A, B and E are individually selected from the group consisting of .dbd.CH-- and .dbd.N-- with at least one being .dbd.N--, R is selected from the group consisting of cycloalkyl of 3 to 6 carbon atoms, and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.2 and R.sub.3 together are --O--CH.sub.2 --O-- or are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.4, --(CH.sub.2).sub.m --CX.sub.3, --O--(CH.sub.2).sub.m --CX.sub.3, --S--(CH.sub.2).sub.m --CX.sub.3, --O--(CX.sub.2).sub.m --CX.sub.3 and --S--(CX.sub.2).sub.m --CX.sub.3, R.sub.Type: GrantFiled: December 20, 1993Date of Patent: September 13, 1994Assignee: Roussel-UclafInventor: Elizabeth A. Kuo
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Patent number: 5342958Abstract: Compounds of the formula ##STR1## wherein A is a hydrogen atoms, a halogen atom, a methyl group, or a methoxy group;B is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, with the proviso that A and B ar not both a hydrogen atom;X and Y each are an oxygen atom or a sulfur atom;R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonyl group;R.sub.1 is a hydrogen atom, an alkyl group, a halogen substituted alkyl group, an alkoxy substituted alkyl group, an alkylthio substituted alkyl group, a cyano substituted alkyl group, a 1-cycloalkenyl group, a benzyl group, a halogen substituted benzyl group, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsulfonyl group, while furthermore R and R.sub.1 together with the group ##STR2## indicated in the above formula may form a ring system; and R.sub.Type: GrantFiled: August 11, 1993Date of Patent: August 30, 1994Assignee: Solvay Duphar International Research B.V.Inventors: Kobus Wellinga, Rudolf Mulder
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Patent number: 5336772Abstract: N-fluoropyridinium salts of the following formula are prepared by reacting a pyridine compound with a Br nsted acid and fluorine, wherein the reaction solvent contains a greater than equimolar amount of the pyridine compound relative to an amount of the Br nsted acid. ##STR1## The method can produce N-fluoropyridinium salts with a high yield.Type: GrantFiled: December 26, 1991Date of Patent: August 9, 1994Assignee: Onoda Cement Co., Ltd.Inventors: Yukinori Saiki, Kazunori Nukui
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Patent number: 5334722Abstract: Fungicidal compounds of formula (I): ##STR1## in which X and Y are independently O or S, and A and R.sup.1 to R.sup.4 have various specified values.Type: GrantFiled: April 7, 1992Date of Patent: August 2, 1994Assignee: Imperial Chemical Industries PLCInventors: Patrick J. Crowley, Alasdair T. Glen, Rosamund A. Spence, Kevin R. Lawson
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Patent number: 5326868Abstract: The present invention encompasses structures of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## and X represents hydrogen, halogen, or hydroxy;W represents an aryl group unsubstituted or substituted with various organic and inorganic substituents;A, B, C, D, and E represent carbon or nitrogen substituted with hydrogen or various organic and inorganic substituents; andR.sub.3, and R.sub.4 are variables representing various 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 disorders, overdose with benzodiazepine drugs, and enhancement of memory.Type: GrantFiled: August 12, 1993Date of Patent: July 5, 1994Assignee: Neurogen CorporationInventors: Andrew Thurkauf, Alan Hutchison