Fully Saturated Quinolines Patents (Class 546/164)
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Patent number: 5585486Abstract: Disclosed are compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is (CR.sub.5 R.sub.6).sub.n, (CR.sub.5 R.sub.6).sub.n,-aryl, (CR.sub.5 R.sub.6).sub.n -heteroaryl, X-(CR.sub.5 R.sub.6).sub.n, X-(CR.sub.5 R.sub.6).sub.n -aryl or X-(CR.sub.5 R.sub.6).sub.n -heteroaryl wherein aryl and heteroaryl may be optionally substituted;X is 0 or NR.sub.5 ;R.sub.5 and R.sub.6 are independently H or lower alkyl;R.sub.2 is H, halo, lower alkyl or (CR.sub.5 R.sub.6).sub.n -aryl;R.sub.3 and R.sub.4 are independently H or alkyl;A is a D or L isomer of an amino acid selected from the group consisting of alanine, valine, leucine, isoleucine, proline, phenylalanine, glycine, tyrosine, methionine, asparagine, glutamine, aspartic acid, glutamic acid, lysine, arginine, histidine and .beta.-thienylalanine;Z is CH.sub.2 or O; andn is 0-4;pharmaceutical compositions containing the compounds; and a method for inhibiting interleukin-1.beta.Type: GrantFiled: May 12, 1995Date of Patent: December 17, 1996Assignee: Sterling Winthrop Inc.Inventors: Roland E. Dolle, Todd L. Graybill, Gary J. Speier, Catherine P. Prouty, Stanley J. Schmidt
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Patent number: 5519022Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: November 10, 1993Date of Patent: May 21, 1996Assignees: Imperial Chemical Industries Plc, ICI PharmaInventors: Philip N. Edwards, David Waterson
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Patent number: 5512560Abstract: HIV protease inhibitors containing hydroxypyrrolidine or hydroxypiperidine with one or more basic amines are disclosed.Type: GrantFiled: March 29, 1994Date of Patent: April 30, 1996Assignee: Merck & Co., Inc.Inventors: Byeong M. Kim, Joseph P. Vacca
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Patent number: 5506237Abstract: The invention relates to the compounds of formula (I): ##STR1## in which: A represents, with the carbon and nitrogen atoms to which it is attached, a heterocycle,B represents, with the nitrogen atom to which it is attached, a heterocycle,n is equal to 1, 2, 3 or 4,R represents phenyl substituted by at least one halogen or alkyl, hydroxyl, alkoxy, trifluoromethyl, nitro, amino, cyano, carboxyl or alkoxycarbonyl, benzyl, thienyl or pyridyl. The compounds may be used as medicaments.Type: GrantFiled: March 23, 1994Date of Patent: April 9, 1996Assignee: Adir et CompagnieInventors: Guillaume De Nanteuil, Bernard Protevin, Georges Remond, Jean Lepagnol, Veronique Heidet
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Patent number: 5496834Abstract: The present invention provides novel compound of the formulas (Ia) or (I): ##STR1## wherein Q is one or two amino acid residues which may be substituted; R.sup.3 is a carboxyl group which may be esterified or an acyl group; A is an alkylene group; B is hydrogen or an alkyl group which may be substituted or an acyl group; or a salt thereof; ##STR2## wherein R.sup.1 and R.sup.2 may be the same or different and each is hydrogen or a hydrocarbon residue which may be substituted; R.sup.3, A and B have the same definitions as those shown above; m and n each is 0 or 1; provided that where both m and n are both equal to 0, R.sup.3 is a carboxyl group which may be esterified or an acyl group having not less than 7 carbon atoms; or a salt thereof.The compound (Ia) or (I) shows cathepsin L inhibitory and bone resorption inhibitory activities and are useful as a prophylactic/therapeutic agent for osteoporosis.Type: GrantFiled: September 2, 1994Date of Patent: March 5, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Takashi Sohda, Yukio Fujisawa, Satoru Oi, Junji Mizoguchi
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Patent number: 5489583Abstract: 2-Substituted 3-(4-amidinophenyl)propionic acid derivatives of the formula ##STR1## in which A, Ar and B have the meanings stated in the description, and the preparation thereof are described. The compounds are suitable for controlling diseases.Type: GrantFiled: December 28, 1993Date of Patent: February 6, 1996Assignee: BASF AktiengesellschaftInventors: Helmut Mack, Thomas Pfeiffer, Hans W. Hoeffken, Hans-Joachim Boehm, Wilfried Hornberger
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Patent number: 5462939Abstract: Disclosed are compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is (CR.sub.5 R.sub.6).sub.n, (CR.sub.5 R.sub.6).sub.n -aryl, (CR.sub.5 R.sub.6).sub.n -heteroaryl, X-(CR.sub.5 R.sub.6).sub.n, X-(CR.sub.5 R.sub.6).sub.n -aryl or X-(CR.sub.5 R.sub.6).sub.n -heteroaryl wherein aryl and heteroaryl may be optionally substituted;X is O or NR.sub.5 ;R.sub.5 and R.sub.6 are independently H or lower alkyl;R.sub.2 is H, halo, lower alkyl or (CR.sub.5 R.sub.6).sub.n -aryl;R.sub.3 and R.sub.4 are independently H or alkyl;A is a D or L isomer of an amino acid selected from the group consisting of alanine, valine, leucine, isoleucine, proline, phenylalanine, glycine, tyrosine, methionine, asparagine, glutamine, aspattic acid, glutamic acid, lysine, arginine, histidine and .beta.-thienylalanine;Z is CH.sub.2 or O; andn is 0-4;pharmaceutical compositions containing the compounds; and a method for inhibiting interleukin-1.beta.Type: GrantFiled: May 7, 1993Date of Patent: October 31, 1995Assignee: Sterling Winthrop Inc.Inventors: Roland E. Dolle, Todd L. Graybill, Gary J. Speier, Catherine P. Prouty, Stanley J. Schmidt
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Patent number: 5459264Abstract: A method for reducing an .alpha.,.beta.-unsaturated ketone of the present invention includes the step of treating the .alpha.,.beta.-unsaturated ketone with a silyl compound in the presence of a Lewis acid and alcohol to selectively reduce the carbonyl group of the .alpha.,.beta.-unsaturated ketone. According to this method, a deoxy-compound can be obtained from the .alpha.,.beta.-unsaturated ketone by selectively reducing the carbonyl group without reducing an .alpha.,.beta.-unsaturated bond.Type: GrantFiled: December 17, 1993Date of Patent: October 17, 1995Assignee: Shionogi Seiyaku Kabushiki KaishaInventors: Mitsuru Imuta, Makoto Kobayashi, Teruo Iizuka
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Process for producing (E)-alkoxyimino or hydroxyimino-acetamide compounds and intermediates therefor
Patent number: 5442063Abstract: The present invention relates to a process for producing (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides and a process for producing (E)-hydroxyiminoacetamide compounds useful as intermediates for producing them. The present invention also relates to an industrial process for producing (E)-methoxyiminoacetamide compounds useful as agricultural fungicides. This process is advantageous in terms of the cost, safety and the like.Type: GrantFiled: November 2, 1993Date of Patent: August 15, 1995Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kuniyoshi Nishida -
Patent number: 5430150Abstract: Compounds of the formula I: ##STR1## wherein X, Y, Z, a, b, c, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are defined in the specification are provided. The compounds are useful as inhibitors of retroviral protease enzymes.Type: GrantFiled: December 16, 1992Date of Patent: July 4, 1995Assignee: American Cyanamid CompanyInventors: Michael P. Trova, Robert E. Babine, Nan Zhang, Steven R. Schow, Allan Wissner
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Patent number: 5430151Abstract: The present invention relates to new trifluoromethyl-containing pseudopeptides of the general formula (I) ##STR1## in which W, A, B, D, E, R.sub.1, R.sub.2 and R.sub.3 have the meaning as outlined of their making and use as pharmaceuticals.Type: GrantFiled: July 24, 1992Date of Patent: July 4, 1995Assignee: Bayer AktiengesellschaftInventors: Dieter Habich, Wolfgang Roben, Jutta Hansen, Arnold Paessens
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Patent number: 5413999Abstract: Compounds of formula ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen or optionally-substituted C.sub.1-4 alkyl or aryl, or R.sup.1 and R.sup.2 are joined together to form a monocyclic or bicyclic ring system, are HIV protease inhibitors. These compounds are useful in the treatment of infection by HIV and in the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of treating infection by HIV are also described.Type: GrantFiled: May 7, 1993Date of Patent: May 9, 1995Assignee: Merck & Co., Inc.Inventors: Joseph P. Vacca, Bruce D. Dorsey, James P. Guare, M. Katharine Holloway, Randall W. Hungate, Rhonda B. Levin
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Patent number: 5384322Abstract: The invention relates to the compounds of formula (I): ##STR1## in which: A represents, with the nitrogen and carbon atoms to which it is bound, a heterocycle,B represents, with the nitrogen atom to which it is bound, a heterocycle,R.sub.1 represents alkoxy, benzyloxy, phenoxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl or substituted or unsubstituted cycloalkyl,their enantiomers, diastereoisomers and epimers as well as their addition salts with a pharmaceutically acceptable acid, medicinal products containing the same.Type: GrantFiled: September 30, 1993Date of Patent: January 24, 1995Assignee: Adir et CompagnieInventors: Michel Vincent, Georges Remond, Bernard Portevin, Yolande Herve, Jean Lepagnol, Guillaume de Nanteuil
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Patent number: 5350754Abstract: The invention concerns a heterocyclic cycloalkane of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents orAr is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a (3-6C)alkylene group which, together with the carbon atom to which R.sup.2 and R.sup.3 are attached, defines a ring having 4 to 7 ring atoms, and which ring may bear one or two substituents; or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: March 1, 1993Date of Patent: September 27, 1994Assignees: Zeneca Limited, ICI PharmaInventors: Graham C. Crawley, Jean-Marc M. M. Girodeau
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Patent number: 5332822Abstract: Sulfonamide thrombin inhibitors are provided which have the structure ##STR1## including all stereoisomers thereof, wherein X is S or --CH.sub.2 --; m is 0, 1 or 2 when X is --S-- or m is 0 when X is --CH.sub.2 --; n is 1, 2 or 3; R.sup.1 and R.sup.2 are independently H, lower alkyl, cyclo-alkyl, aryl, heteroaryl or heteroarylalkyl, or R.sup.1 and R.sup.2 can be taken together with the N atom to which they are attached to form a 5- to 8-membered ring which may optionally contain an additional N, O or S atom in the ring; R.sup.3 is heteroaryl; and R.sup.4 is alkyl, cycloalkyl, aryl, heteroaryl, quinolinyl or tetrahydroquinolinyl, and pharmaceutically acceptable salts thereof.Type: GrantFiled: December 24, 1992Date of Patent: July 26, 1994Assignee: Bristol-Myers Squibb CompanyInventor: Raj N. Misra
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Patent number: 5310932Abstract: Novel compounds are disclosed having the formula ##STR1## wherein X, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are as defined herein.Type: GrantFiled: September 11, 1991Date of Patent: May 10, 1994Assignee: E. R. Squibb & Sons, Inc.Inventors: Karnail Atwal, George C. Rovnyak
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Patent number: 5294612Abstract: Novel 6-heterocyclyl-pyrazolo[3,4-d]pyrimidin-4-ones, useful in treating cardiovascular disease, are prepared by reacting a 5-amino-1H-pyrazole-4-carboxamide with heterocyclylcarboxaldehyde or by reacting a 5-amino-1H-pyrazole-4-carbonitrile with a heterocyclylcarboxamidine, followed by diazotization and hydrolysis of the resulting 4-amino-6-heterocyclyl-pyrazolo[3,4-d]pyrimidine.Type: GrantFiled: March 30, 1992Date of Patent: March 15, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Baldev Singh, George Y. Lesher, deceased
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Patent number: 5292755Abstract: Benzoylguanidines of the formula I ##STR1## where R(1) or R(2) is equal to R(6)--S(O).sub.n -- or R(7)R(8)N--O.sub.2 S--and the other substituent R(1) or R(2) is in each case equal to H, F, Cl, Br, I, alkyl, alkoxy or phenoxy, R(6)--S(O).sub.n or R(7)R(8)N--and R(6) is equal to alkyl, cycloalkyl, cyclopentylmethyl, cyclohexylmethyl or phenyl,R(7) and R(8) are equal to alkyl or phenylalkyl or phenyl,and in which R(7) and R(8) may also together be a C.sub.4 --C.sub.7 chain, and in which R(7) and R(8), together with the nitrogen atom to which they are bonded, may be a dihydroindole, tetrahydroquinoline or tetrahydroisoquinoline system,and where R(3), R(4) and R(5) are equal to hydrogen or alkyl, or R(3) and R(4) are together an alkylene chain or R(4) and R(4) are together an alkylene chain,and where n is equal to zero, 1 or 2and their pharmaceutically tolerable salts are outstanding antiarrhythmics.Type: GrantFiled: January 31, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Heinrich C. Englert, Hans-Jochen Lang, Wolfgang Linz, Bernward Scholkens, Wolfgang Scholz
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Patent number: 5286732Abstract: The invention relates to the compounds of formula (I): ##STR1## in which: A represents, with the nitrogen and carbon atoms to which it is bound, a heterocycle,B represents, with the nitrogen atom to which it is bound, a heterocycle,R.sub.1 represents alkoxy, benzyloxy, phenoxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl or substituted or unsubstituted cycloalkyl,their enantiomers, diastereoisomers and epimers as well as their addition salts with a pharmaceutically acceptable acid, medicinal products containing the same.Type: GrantFiled: September 25, 1992Date of Patent: February 15, 1994Assignee: Adir et CompagnieInventors: Michel Vincent, Georges Remond, Bernard Portevin, Yolande Herve, Jean Lepagnol, Guillaume de Nanteuil
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Patent number: 5217977Abstract: The invention concerns a heterocyclic cycloalkane of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl; and R.sup.2 and R.sup.3 together form a (3-6C)alkylene group which, together with the carbon atom to which R.sup.2 and R.sup.3 are attached, defines a ring having 4 to 7 ring atoms, and which ring may bear one or two substituents;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: November 15, 1991Date of Patent: June 8, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Jean-Marc M. M. Girodeau
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Patent number: 5204471Abstract: New .alpha.-trifluoromethyl-substituted, saturated bicyclic amines of the formula ##STR1## in which R.sup.1 represents hydrogen, C.sub.1 - to C.sub.8 -alkyl or C.sub.1 - to C.sub.8 -alkoxy,R.sup.2 represents hydrogen or C.sub.1 - to C.sub.4 -alkyl,n represents zero or 1,A represents ##STR2## B represents NH or ##STR3## and C represents ##STR4## in which A, B and C are either each different from one another or C represents ##STR5## and one of A and B represents NH and the other represents ##STR6## and R.sup.3 denotes hydrogen or C.sub.1 - to C.sub.4 -alkyl and the ring D is saturated.Type: GrantFiled: July 24, 1992Date of Patent: April 20, 1993Assignee: Bayer AktiengesellschaftInventors: Michael Negele, Dieter Habich, Christian Laue, Heinz Ziemann
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Patent number: 5196438Abstract: Compounds having the formula ##STR1## wherein R is benzyloxycarbonyl or 2-quinolylcarbonyl, and their pharmaceutically acceptable acid addition salts inhibit proteases of viral origin and can be used as medicaments for the treatment of prophylaxis of viral infections in mammals, humans or non-humans.Type: GrantFiled: November 19, 1990Date of Patent: March 23, 1993Assignee: Hoffmann-La Roche Inc.Inventors: Joseph A. Martin, Sally Redshaw
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Patent number: 5192799Abstract: Amine represented by the following formula (1), or their acid addition salts or their quaternary ammonium salts. ##STR1## The amines of formula (1) or their pharmaceutically acceptable acid addition salts or quaternary ammonium salts are useful for the treatment and prevention of heart diseases of animals, particularly arrhythima, myocardial infarction, angina pectoris and heart failure and psychoneurological diseases.Type: GrantFiled: June 5, 1992Date of Patent: March 9, 1993Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Ikuo Tomino, Masaharu Ishiguro, Takumi Kitahara, Keiichi Yokoyama, Noriaki Kihara, Joji Kamiya, Kanji Yoshihara, Masaaki Ishii, Akira Mizuchi, Kazutoshi Horikomi, Akira Awaya, Takuo Nakano
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Patent number: 5151436Abstract: Therapeutically useful thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Het represents pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]-pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]-pyridin-6-yl, Y represents ethylene, methylene or a valency bond, and X represents carbonyl, hydroxymethylene, >C.dbd.NOR.sup.1, >C.dbd.NN(R.sup.1).sub.2 or >C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2 in which R.sup.1 represents hydrogen or optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl, or two R.sup.1 substituents on the same nitrogen atom may together form an optionally substituted alkylene radical chain and salts thereof, processes for their preparation and compositions containing them are described.Type: GrantFiled: August 23, 1990Date of Patent: September 29, 1992Assignee: Rhone-Poulenc SanteInventors: David C. Cook, Terance W. Hart, Iain M. Mc Lay, Malcolm N. Palfreyman, Brian W. Sharp, Roger J. A. Walsh
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Patent number: 5134143Abstract: 7- or 8-Substituted, partially hydrogenated pyrazolo[3,4-g]quinoline, thiazolo[4,5-g]quinoline, oxazolo[4,5-g]quinoline, and pyrrolo[3,4-g]quinoline derivatives, and 8- or 9-substituted, partially hydrogenated pyrido[2,3-g]quinazoline derivatives are D-2 dopamine agonists. 6-Oxo-1-substituted-octahydroquinolines and 6-oxo-1-substituted-decahydroquinolines which are additionally substituted in the 3- or 4-position are intermediates useful in preparation of the dopamine agonists. Acetals of 4,6-dioxo-1-substituted-decahydroquinoline 3-carboxylic acid esters enable synthesis of the foregoing compounds.Type: GrantFiled: October 5, 1990Date of Patent: July 28, 1992Assignee: Eli Lilly and CompanyInventors: Diane L. Huser, John M. Schaus
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Patent number: 5124322Abstract: Novel compounds of formula (I), salts, solvates and hydrates thereof: ##STR1## in which: R.sub.1 and R.sub.2 are independently hydrogen; alkyl; alkoxy; halogen; or CF.sub.3 ;R.sub.3 is hydrogen; acyl, such as ##STR2## where Z is optionally substituted aryl; or a group R--S-- where R is an organic residue such that the group R--S-- provides an in vivo-cleavable disulphide bond;R.sub.4 is C.sub.3-6 alkyl;R.sub.5 is hydrogen; alkyl; --CH.sub.2 --R.sub.10 where R.sub.10 is optionally substituted phenyl or heteroaryl; or a group ##STR3## where R.sub.11 is hydrogen; alkyl; or --CH.sub.2 --Ph is optionally substituted phenyl; and R.sub.12 is hydrogen or alkyl; andR.sub.6 is hydrogen; alkyl; or a group ##STR4## where R.sub.13 is hydrogen; or alkyl; and R.sub.14 is hydroxy; alkoxy; or --NR.sub.7a R.sub.8 where each of R.sub.7a and R.sub.8 is hydrogen or alkyl, or R.sub.7a and R.sub.Type: GrantFiled: June 19, 1989Date of Patent: June 23, 1992Assignee: Beecham Group p.l.c.Inventor: Ian Hughes
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Patent number: 5104872Abstract: Compound of the general formula (I), which is useful as an agricultural and horticultural fungicide, an agricultural and horticultural fungicidal composition containing said compound, use of said composition for controlling plant disease, and process for the production of said compound: ##STR1## wherein ##STR2## shows a case in which R.sup.3 and R.sup.4 together form a cyclic substituent, and R.sup.1 and R.sup.4 are substituents disclosed in the specification.Type: GrantFiled: August 15, 1990Date of Patent: April 14, 1992Assignee: Nihon Hohyaku Co., Ltd.Inventors: Kenji Tsubata, Nobuyuki Niino, Katsutoshi Endo, Yoshinobu Yamamoto, Hideo Kanno
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Patent number: 5101034Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.Type: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5100904Abstract: A novel prolinal derivatives of the general formula: ##STR1## [wherein A represents alkylene or alkenylene group of from 1 to 8 carbon atom(s) or a saturated hydrocarbon ring of from 3 to 7 carbon atoms,R represents hydrogen atom, phenyl group, benzyl group, alkyl group of from 1 to 8 carbon atom(s) or cycloalkyl group of from 3 to 7 carbon atoms,B represents alkylene group of from 1 to 8 atom(s) unsubstituted or substituted by phenyl group or benzyl group, or a single bond,D represents carbocyclic or heterocyclic ring unsubstituted or substituted by from one to three of halogen atom, alkyl or alkoxy group of from 1 to 4 carbon atom(s), nitro group or trifluoromethyl group.]possess inhibitory activity on prolyl endopeptidase, and therefore are useful for treating and/or preventing agent as a amnesia.Type: GrantFiled: June 5, 1990Date of Patent: March 31, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Shuichi Ohuchida, Hiroyuki Ohno
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Patent number: 5047400Abstract: The invention relates to the compounds of general formula: ##STR1## in which: X denotes either an oxygen atom, or two hydrogen atoms;Y denotes either a hydrogen atom, or a hydroxyl group;or Y denotes an amino group on condition that X denotes two hydrogen atoms;R denotes a hydrogen atom, or a straight- or branched-chain alkyl group having 1 to 6 carbon atoms, optionally substituted with one or more hydroxy, amino, mercapto, methylthio or carboxy groups, or aryl groups such as phenyl, pyridyl or thienyl; ##STR2## denotes a polycyclic nitrogenous structure; their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base.Type: GrantFiled: June 16, 1988Date of Patent: September 10, 1991Assignee: Adir et CieInventors: Michel Vincent, Georges Remond, Bernard Portevin, Claude Cudennec
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Patent number: 5047539Abstract: Heterocyclic amidine derivatives of the general formula I ##STR1## in which the variables R.sup.1 are the same or different and denote hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl or chlorine,R.sup.2 to R.sup.5 denote hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.3 and R.sup.4 can together form a five-membered or six-membered ring,R.sup.6 denotes hydrogen or C.sub.1 -C.sub.8 -alkyl,R.sup.7 denotes cyano or --COOR.sup.8, --COR.sup.8, --CONHR.sup.8 or --CONR.sup.8.sub.2, in whichR.sup.8 is a straight-chain or branched-chain C.sub.1 -C.sub.12 -alkyl group which may be interrupted by oxygen atoms, a cyclopentyl or cyclohexyl group or a phenylalkyl group having from 1 to 3 carbon atoms in the alkyl moiety,A is a chemical bond or a methylene group which may additionally carry one or two C.sub.1 -C.sub.4 -alkyl radicals, andm and n are each 1 or 2.The said heterocyclic amidine derivatives I serve as UV stabilizers for organic materials.Type: GrantFiled: April 19, 1990Date of Patent: September 10, 1991Assignee: BASF AktiengesellschaftInventors: Peter Spang, Peter Neumann, Hubert Trauth
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Patent number: 5019650Abstract: Known and novel 4-aryl-4-piperidinecarbinols and heterocyclic analogs are useful as analgesics. Also provided are novel pyrrolidinecarbinols and hexhydroazepine carbinols which are useful as analgesics, antidepressants and, in some cases, as anorectic agents.Type: GrantFiled: August 28, 1989Date of Patent: May 28, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Engelbert Ciganek, Leonard Cook
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Patent number: 5017708Abstract: A compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each is hydrogen, hydroxy, oxo, halogen, azido, amino, C.sub.1 -C.sub.3 alkylamino, or aminomethyl, in which said amino, C.sub.1 -C.sub.3 alkylamino and aminomethyl each is optionally substituted by one or two members selected from the group consisting of C.sub.1 -C.sub.3 alkyl and amino-protecting group; n is an integer of 1 to 3; p and q each is an integer of 0 to 3 with proviso that p+q=1 to 4 or acid-addition salts thereof, being useful materials for preparing side chains of antibacterial quinolonecarboxylic acids, cephalosporines, or other antibiotics.Type: GrantFiled: September 8, 1989Date of Patent: May 21, 1991Assignee: Shionogi & Co., Ltd.Inventors: Masaru Ogata, Hiroshi Matsumoto, Sumio Shimizu, Shiro Kida
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Patent number: 5008276Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 4988810Abstract: Novel enantiomeric and diastereoisomeric forms of decahydroquinolines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom to which they are connected from a 5 to 6 member heterocycle optionally including another heteroatom and optionally substituted, A is selected from the group consisting of --(CH.sub.2).sub.n -- and alkylene substituted with an alkyl and having 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, naphthyl indenyl, monocyclic heterocycle of 5 to 6 members and a bicyclic heterocycle all being unsubstituted or substituted by one or more substituents and their non-toxic, pharmaceutically acceptable acid addition salts and quaternary ammonium salts having central analgesic properties.Type: GrantFiled: August 4, 1989Date of Patent: January 29, 1991Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin, Odile Le Martret, Francoise Delevallee
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Patent number: 4977160Abstract: 7- or 8-Substituted, partially hydrogenated pyrazolo[3,4-g]quinoline, thiazolo[4,5-g]quinoline, oxazolo[4,5-g]quinoline, and pyrrolo[3,4-g]quinoline derivatives, and 8- or 9-substituted, partially hydrogenated pyrido[2,3-g]quinazoline derivatives are D-2 dopamine agonists. 6-Oxo-1-substituted-octahydroquinolines and 6-oxo-1-substituted-decahydroquinolines which are additionally substituted in the 3- or 4-position are intermediates useful in preparation of the dopamine agonists. Acetals of 4,6-dioxo-1-substituted-decahydroquinoline 3-carboxylic acid esters enable synthesis of the foregoing compounds.Type: GrantFiled: February 16, 1989Date of Patent: December 11, 1990Assignee: Eli Lilly and CompanyInventors: Diane L. Huser, John M. Schaus
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Patent number: 4968700Abstract: Novel enantiomeric and diastereoisomeric forms of decahydroquinolines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom to which they are connected form a 5 to 6 member heterocycle optionally including another heteroatom and optionally substituted, A is selected from the group consisting of --(CH.sub.2).sub.n -- and alkylene substituted with an alkyl and having 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, naphthyl indenyl, monocyclic heterocycle of 5 to 6 members and a bicyclic heterocycle all being unsubstituted or substituted by one or more substituents and their non-toxic, pharmaceuically acceptable acid addition salts and quaternary ammonium salts having central analgesic properties.Type: GrantFiled: July 11, 1988Date of Patent: November 6, 1990Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin, Odile Le Martret, Francoise Delevallee
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Patent number: 4963548Abstract: Novel fungicidally active compounds of the formula ##STR1## in which R represents alkyl, cyanoalkyl or in each case optionally substituted alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl or phenylalkyl,R.sup.1 represents the --OR.sup.2 or --NR.sup.3 R.sup.4 groups, andR.sup.3 and R.sup.4 have special special definitions.Type: GrantFiled: May 27, 1988Date of Patent: October 16, 1990Assignee: Bayer AktiengesellschaftInventors: Winfried Lunkenheimer, Wilhelm Brandes, Gerd Hanssler
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Patent number: 4963567Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms of a decahydroquinoline of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, A is selected from the group consisting of --(CH.sub.2).sub.n --, --CH.sub.2 O-- and alkylene substituted with alkyl having a total of 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, optionally substituted naphthyl, optionally substituted indenyl, optionally substituted heteromonocycle of 5 to 6 members and optionally substituted hetero-bicycle with the proviso that when Z is o-alkoxy-phenyl, A is not --(CH.sub.2).sub.n -- in which n is O, and their non-toxic, pharmaceutically acceptable acid addition salts and their quaternary ammonium salts and intermediates having analgesic, diuretic, hypotensive, anti-arrithmic and anti-cerebral-ischaemic properties.Type: GrantFiled: June 27, 1989Date of Patent: October 16, 1990Assignee: Roussel UclafInventors: Francois Clemence, Odile Le Martret, Francoise Delevallee, Michel Fortin
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Patent number: 4954518Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.Type: GrantFiled: October 7, 1988Date of Patent: September 4, 1990Assignee: Toyama Chemical Company, Ltd.Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
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Patent number: 4952573Abstract: Compounds which enhance the efficiency of the corneal endothelial fluid pump thereby promoting normal corneal function and deturgescence of swollen corneas, and methods for the compounds' synthesis are described. In addition, surgical irrigating solutions which include one or more of the compounds are discussed along with methods for their use.Type: GrantFiled: March 23, 1988Date of Patent: August 28, 1990Assignee: Laboratoirs Alcon S.A.Inventors: Gerard LeClerc, Beatrice Ruhland, Guy Andermann, Georges de Burlet, Michel Dietz
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Patent number: 4950760Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms of a decahydroquinoline of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, A is selected from the group consisting of --(CH.sub.2).sub.n --, --CH.sub.2 O-- and alkylene substituted with alkyl having a total of 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, optionally substituted naphthyl, optionally substituted indenyl, optionally substituted heteromonocycle of 5 to 6 members and optionally substituted heterobicycle with the proviso that when Z is o-alkoxy-phenyl, A is not --(CH.sub.2).sub.n -- in which n is O, and their non-toxic, pharmaceutically acceptable acid addition salts and their quaternary ammonium salts and intermediates having analgesic, diuretic, hypotensive, anti-arrithmic and anti-cerebral-ischaemic properties.Type: GrantFiled: May 8, 1989Date of Patent: August 21, 1990Assignee: Roussel UclafInventors: Francois Clemence, Odile Le Martret, Francoise Delevallee, Michel Fortin
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Patent number: 4933361Abstract: Disclosed are cis, exo- and trans-compounds of the formula I ##STR1## in which n denotes 0, 1 or 2, R.sub.1 denotes hydrogen, (C.sub.1 -C.sub.6)-alkyl which can optionally be substituted by amino, (C.sub.1 -C.sub.4)-acyl- or bezoylamino, (C.sub.2 -C.sub.6)-alkenyl, (C.sub.5 -C.sub.9)-cycloalkyl, (C.sub.5 -C.sub.9)-cycloalkenyl, (C.sub.5 -C.sub.7)-cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, aryl or partially hydrogenated aryl, which can, in each case, be substituted by (C.sub.1 -C.sub.2)-alkyl, (C.sub.1 -C.sub.2)-alkoxy or halogen, aryl-(C.sub.1 -C.sub.4)-alkyl, /which can be substituted as defined previously in the aryl radical/, a monocyclic or bicyclic sulfur or nitrogen and/or nitrogen heterocyclic radical, or a side chain of naturally occurring aminoacid, R.sub.2 denotes hydrogen, (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.6)-alkenyl or aryl-(C.sub.1 -C.sub.4)-alkyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen, X denotes (C.sub.1 -C.sub.6)-alkyl, (C.sub.2 -C.sub.Type: GrantFiled: April 28, 1989Date of Patent: June 12, 1990Assignee: Hoechst AktiengesellschaftInventors: Hansjorg Urbach, Rainer Henning, Volker Teetz, Rolf Geiger, Reinhard Becker, Holger Gaul
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Patent number: 4906643Abstract: N-(3-hydroxy-4-piperidinyl)substituted benzamides, their N-oxide forms and pharmaceutically acceptable acid-addition salts having gastrointestinal motility stimulating properties, compositions containing the same, and methods of treating warm blooded animals suffering from a decreased peristalsis of the gastrointestinal system.Type: GrantFiled: June 10, 1988Date of Patent: March 6, 1990Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Karel J. Van Loon
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Patent number: 4882339Abstract: Disclosed are compounds of the formula ##STR1## wherein R.sub.1 represents unsubstituted or lower alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, unsubstituted or lower alkyl substituted C.sub.7 -or C.sub.8 -bicycloalkyl, unsubstituted or lower alkyl-substituted adamantyl, 4-piperidinyl or N-lower alkyl or aryl-lower alkyl-substituted piperidinyl, 1- or 2-indanyl, 1- or 2-tetrahydronaphthyl, 1- or 2-perhydroindanyl, 1- or 2-perhydronaphthyl; R.sub.2 represents hydrogen, lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl, aryl-lower alkyl, C.sub.3 -C.sub.7 -cycloalkyl-lower alkyl, lower alkanoyl or aryl-lower alkanoyl; or R.sub.1 and R.sub.2 combined with the nitrogen to which they are attached represent pyrrolidino, piperidino, perhydroazepino, morpholino, thiomorpholino, tetrahydro- or perhydro-(isoquinolinyl or quinolinyl), dihydro- or perhydroindolyl, piperazino or N-lower alkyl-piperazino; R.sub.Type: GrantFiled: July 10, 1987Date of Patent: November 21, 1989Assignee: Ciba-Geigy CorporationInventor: Jan W. F. Wasley
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Patent number: 4877796Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms of a decahydroquinoline of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 5 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen and akyl of 1 to 5 carbon atoms, A is selected from the group consisting of --(CH.sub.2).sub.n --, --CH.sub.2 O-- and alkylene substituted with alkyl having a total of 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, optionally substituted naphthyl, optionally substituted indenyl, optionally substituted heteromonocycle of 5 to 6 members and optionally substituted heterobicycle with the proviso that when Z is o-alkoxy-phenyl, A is not --(CH.sub.2).sub.n -- in which n is O, and their non-toxic, pharmaceutically acceptable acid addition salts and their quaternary ammonium salts and intermediates having analgesic, diuretic, hypotensive, anti-arrithmic and anti-cerebral-ischaemic properties.Type: GrantFiled: August 12, 1987Date of Patent: October 31, 1989Assignee: Roussel UclafInventors: Francois Clemence, Odile Le Martret, Francoise Delevallee, Michel Fortin
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Patent number: 4831145Abstract: This invention provides a process for preparing trans 2-aminopyrimido[4,5-g]quinolines employing novel intermediates.Type: GrantFiled: May 23, 1988Date of Patent: May 16, 1989Assignee: Eli Lilly and CompanyInventors: Leland O. Weigel, Gilbert S. Staten
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Patent number: 4826986Abstract: 7- or 8-Substituted, partially hydrogenated pyrazolo[3,4-g]quinoline, thiazolo[4,5-g]quinoline, oxazolo[4,5-g]quinoline, and pyrrolo[3,4-g]quinoline derivatives, and 8- or 9-substituted, partially hydrogenated pyrido[2,3-g]quinazoline derivatives are D-2 dopamine agonists. 6-Oxo-1-substituted-octahydroquinolines and 6-oxo-1-substituted-decahydroquinolines which are additionally substituted in the 3- or 4-position are intermediates useful in preparation of the dopamine agonists. Acetals of 4,6-dioxo-1-substituted-decahydroquinoline 3-carboxylic acid esters enable synthesis of the foregoing compounds.Type: GrantFiled: June 16, 1986Date of Patent: May 2, 1989Assignee: Eli Lilly and CompanyInventors: Diane L. Huser, John M. Schaus
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Patent number: 4816465Abstract: Novel enantiomeric and diastereoisomeric forms of decahydroquinolines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken together with the nitrogen atom to which they are connected form a 5 to 6 member heterocycle optionally including another heteroatom and optionally substituted, A is selected from the group consisting of --(CH.sub.2).sub.n -- and alkylene substituted with an alkyl and having 2 to 8 carbon atoms, n is an integer from 0 to 5, Z is selected from the group consisting of optionally substituted phenyl, naphthyl indenyl, monocyclic heterocycle of 5 to 6 members and a bicyclic heterocycle all being unsubstituted or substituted by one or more substituents and their non-toxic, pharmaceutically acceptable acid addition salts and quaternary ammonium salts having central analgesic properties.Type: GrantFiled: January 13, 1987Date of Patent: March 28, 1989Assignee: Roussel UclafInventors: Francois Clemence, Michel Fortin, Odile Le Martret, Francoise Delevallee
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Patent number: 4778894Abstract: Tautomeric mixtures of trans-(.+-.)-3,5-dialkyloctahydropyrazolo[3,4-g]quinoline, of trans-(.+-.)-6-alkyloctahydropyrazolo[4,3-f]quinoline, and of trans-(.+-.)-1,6-dialkyloctahydropyrazolo[4,3-f]quinoline, individual enantiomer thereof, pharmaceutically-acceptable acid addition salts thereof, and intermediates useful in the preparation thereof, useful as hypotensive agents.Type: GrantFiled: April 23, 1986Date of Patent: October 18, 1988Assignee: Eli Lilly and CompanyInventors: John M. Schaus, Diane L. Huser, Richard N. Booher