Chalcogen Bonded Directly To Ring Carbon Of The Five-membered Hetero Ring (e.g., 3-indolols, Etc.) Patents (Class 548/484)
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Patent number: 6166040Abstract: Pharmaceutical compounds of the formula: ##STR1## in which n is 1 to 6, m is 1 or 2 and p is 1 or 2, R.sup.1 and R.sup.2 are each hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, HO--C.sub.1-4 alkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, C.sub.1-4 alkylthio, halo, optionally substituted phenyl, optionally substituted phenyl-C.sub.1-4 alkyl, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a C.sub.3-6 cycloalkyl group, >C.dbd.O, C.dbd.NOR' where R' is hydrogen or C.sub.1-4 alkyl,R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, halo, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkyl-CO--, where m is 0, 1 or 2, R'R"N--SO.sub.2 --, --COOR', --CONR'R", --NR'R", --N(OR')COOR", --COR', --NHSO.sub.2 R', where R' and R' are each hydrogen or C.sub.1-4 alkyl,R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl,X is oxygen or sulphur,the dotted line represents an optional double bond, and the fluorine atom is attached at the 6- or 7-position; and salts thereof.Type: GrantFiled: May 11, 1999Date of Patent: December 26, 2000Assignee: Eli Lilly and Company LimitedInventors: John Fairhurst, Peter Thaddeus Gallagher, Martin Victor Miles, William Martin Owton, Colin William Smith
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Patent number: 6150394Abstract: Compounds having a metalloproteinase inhibitory activity, represented by the formula (I), its optically active isomers, their pharmaceutically acceptable salts, or hydrates thereof.Type: GrantFiled: July 22, 1998Date of Patent: November 21, 2000Assignee: Shionogi & Co., Ltd.Inventors: Fumihiko Watanabe, Hiroshige Tsuzuki, Mitsuaki Ohtani
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Patent number: 6147105Abstract: Novel 2-phenyl indoles are disclosed of general formula (I), wherein: R.sup.1 represents one of the rests --(CH.sub.2).sub.n --S(O).sub.m --R.sup.4, --(CH.sub.2).sub.n --NR.sup.6 --SO.sub.2 --R.sup.4, (a), and n' being integers between 4 and 12 and m and m' are 0, 1 or 2; X represents a methylene group, an imino group .dbd.NR.sup.6, or an oxygen or sulphur atom; R.sup.2 and R.sup.3 independently of one another represent a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a benzyl, alkanoyl or alkanoyloxy, or carbarnoyl rest of formula --C(O)R.sup.5 or --C(O)NR.sup.6 R.sup.7 or a tetrahydropyranyl group; R.sup.4 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl, a completely or partially fluorinated alkyl group --(CH.sub.2).sub.o --(CF.sub.2).sub.p CF.sub.3, o and p being independently of one another integers between 0 and 6, an (alkyl)amino or (alkyl)carbamoyl group of formula (CH.sub.2).sub.q --Y--NR.sup.8 R.sup.Type: GrantFiled: May 14, 1997Date of Patent: November 14, 2000Assignee: Schering AktiengesellschaftInventors: Erwin Von Angerer, Christian Biberger, Martin Schneider
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Patent number: 6063806Abstract: A heterocyclic derivative of the formula (I) ##STR1## wherein each symbol is as defined in the specification, and pharmaceutically acceptable salts thereof. The compound (I) of the present invention and pharmaceutically acceptable salts thereof exhibit superior ACAT inhibitory activity and lipoperoxidation inhibitory activity in mammals, and are useful as ACAT inhibitors and lipoperoxidation inhibitors. Specifically, they are useful for the prophylaxis and treatment of arteriosclerosis, hyperlipemia, arteriosclerosis in diabetes, and cerebrovascular and cardiovascular ischemic diseases.Type: GrantFiled: April 3, 1998Date of Patent: May 16, 2000Assignee: Kyoto Pharmaceutical Industries, Ltd.Inventors: Shoji Kamiya, Hiroaki Shirahase, Hiroshi Matsui, Shohei Nakamura, Katsuo Wada
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Patent number: 6043257Abstract: The present application describes amidinoindoles, amidinoazoles, and analogs thereof of formula I: ##STR1## wherein W, W.sup.1, W.sup.2, and W.sup.3 are selected from CH and N, provided that one of W.sup.1 and W.sup.2 is C(C(.dbd.NH)NH.sub.2) and at most two of W, W.sup.1, W.sup.2, and W.sup.3 are N and one of J.sup.a and J.sup.b is substituted by --(CH.sub.2).sub.n --Z--A--B, which are useful as inhibitors of factor Xa or thrombin.Type: GrantFiled: October 21, 1998Date of Patent: March 28, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Celia Dominguez, Qi Han, Daniel Emmett Duffy, Jeongsook Maria Park, Mimi Lifen Quan, Karen Anita Rossi, Ruth Richmond Wexler
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Patent number: 6004933Abstract: The present invention relates to cysteine protease inhibitors of the general formula (I): ##STR1## wherein Z is a cysteine protease binding moiety; X and Y are S, O or optionally substituted N; and R.sub.1 is optionally substituted alkyl or aryl.Type: GrantFiled: April 23, 1998Date of Patent: December 21, 1999Assignee: Cortech Inc.Inventors: Lyle W. Spruce, Albert C. Gyorkos, John C. Cheronis, Val S. Goodfellow, Axel H. Leimer, John M. Young, James Ivan Gerrity
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Patent number: 6002018Abstract: The invention relates to N-substituted 4-hydroxyindoline derivatives, to their process of synthesis, to their use as couplers for the oxidation of dyeing of keratinous fibers, in combination with at least one oxidation base, and to the dyeing processes in which they are used.Type: GrantFiled: January 28, 1998Date of Patent: December 14, 1999Assignee: L'OrealInventors: Eric Terranova, Aziz Fadli, Alain Lagrange
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Patent number: 5994546Abstract: Disclosed are 4-(N,N-dialkylamino)aniline compounds having a 4-N substituent which is a polyethyleneoxy group and which forms a condensed ring with benzene ring, such as aniline compounds having the following structure, a processing composition containing such a compound and a method for forming a color image with the processing solution. The aniline compound is useful as a color developing agent capable of having a low fog density and sufficient yellow and cyan image densities and suitable for the rapid process.Type: GrantFiled: February 11, 1998Date of Patent: November 30, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Keizo Kimura, Shigeo Hirano, Hiroshi Kawamoto
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Patent number: 5948808Abstract: Provided in the present invention are compounds and compositions of substituted indole-3-carbinols and diindolylmethane suitable for treating estrogen-dependent tumors. Also provided are methods of treating such cancerous-conditions.Type: GrantFiled: March 7, 1997Date of Patent: September 7, 1999Assignee: The Texas A&M University SystemInventor: Stephen H. Safe
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Patent number: 5932731Abstract: The present invention provides a process for preparing an aromatic or heteroaromatic thiol represented by the formula (2), the process comprising hydrolyzing an aromatic or heteroaromatic halogenated methyl sulfide represented by the formula (1)Ar.paren open-st.SCH.sub.3-m X.sub.m).sub.n (1)Ar.paren open-st.SH).sub.n (2)wherein Ar is an aromatic or heteroaromatic ring which has no substituent or which has an optional substituent or substituents, X is a halogen atom, m is an integer of 1 to 3 and n is 1 or 2.Type: GrantFiled: December 22, 1997Date of Patent: August 3, 1999Assignee: Sumitomo Seika Chemicals Co., Ltd.Inventors: Hiroshi Goda, Mikio Yamamoto, Jun-ichi Sakamoto, Hitoshi Karino
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Patent number: 5925651Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.Type: GrantFiled: April 1, 1997Date of Patent: July 20, 1999Assignee: Merck & Co., Inc.Inventor: John H. Hutchinson
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Patent number: 5922716Abstract: Compounds of formula (I): ##STR1## wherein R represents a CR.sub.4 R.sub.5, CHR.sub.6, or C.dbd.R.sub.7 radical and R.sub.3 represents an oxygen atom, salts thereof, the preparation thereof and drugs containing same. The compounds of formula (I) have valuable pharmacological properties and are alpha-amino-3-hydroxy-5-methyl-4-osoxaziepropionic acid (AMPA) receptor antagonists, said receptor also being known as the quisqualate receptor. Furthermore, the compounds of formula (I) are non-competitive N-methyl-D-aspartate (NMDA) receptor antagonists, and particularly NMDA receptor glycine modulation site ligands.Type: GrantFiled: September 27, 1996Date of Patent: July 13, 1999Assignee: Rhone-Poulenc Rorer S.A.Inventors: Jean-Claude Aloup, Fran.cedilla.ois Audiau, Michel Barreau, Dominique Damour, Arielle Genevois-Borella, Patrick Jimonet, Serge Mignani, Yves Ribeill
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Patent number: 5885967Abstract: This invention relates to peptide derivatives, pharmaceutical formulations containing those compound and methods of their use as thrombin inhibitors.Type: GrantFiled: March 4, 1994Date of Patent: March 23, 1999Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
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Patent number: 5840984Abstract: Odor formation during storage of (hydrocarbylthio)aromatic amines due to formation and release of odoriferous sulfur-containing species such as dihydrocarbyldisulfides, is suppressed. To accomplish this, a small amount of N,N-dihydrocarbylhydroxylamine odor-inhibitor (e.g., N,N-diethylhydroxylamine) is blended with the (hydrocarbylthio)aromatic amine. This enables products such as a mixture of 3,5-di(methylthio)-2,4-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene) to be stored for long periods of time with significantly reduced formation and release of odoriferous sulfur-containing species.Type: GrantFiled: June 23, 1997Date of Patent: November 24, 1998Assignee: Albemarle CorporationInventors: Gregory H. Lambeth, Paul L. Wiggins, William R. Brown
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Patent number: 5817833Abstract: Compounds of formula (I) or a salt thereof: ##STR1## R.sup.1 is hydrogen, halogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, COC.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, hydroxyC.sub.1-6 alkyl, hydroxyC.sub.1-6 alkoxy, C.sub.1-6 alkoxyC.sub.1-6 alkoxy, acyl, nitro, trifluoromethyl, cyano, CHO, SR.sup.9, SOR.sup.9, SO.sub.2 R.sup.9, SO.sub.2 NR.sup.10 R.sup.11, CO.sub.2 R.sup.10, NR.sup.10 SO.sub.2 R.sup.11, CONR.sup.10 R.sup.11, CO.sub.2 NR.sup.10 R.sup.11, CONR.sup.10 (CH.sub.2).sub.p CO.sub.2 R.sup.11, (CH.sub.2).sub.p NR.sup.10 R.sup.11, (CH.sub.2).sub.p CONR.sup.10 R.sup.11, (CH.sub.2).sub.p NR.sup.10 COR.sup.11, (CH.sub.2).sub.p CO.sub.2 C.sub.1-6 alkyl, CO.sub.2 (CH.sub.2).sub.p OR.sup.10, CONHNR.sup.10 R.sup.11, NR.sup.10 R.sup.11, NR.sup.10 CO.sub.2 R.sup.11, NR.sup.10 CONR.sup.10 R.sup.11, CR.sup.10 .dbd.NOR.sup.11, CNR.sup.10 .dbd.NOR.sup.11, where R.sup.10 and R.sup.11 are independently hydrogen or C.sub.1-6 alkyl and p is 1 to 4;R.sup.2 and R.sup.3 are independently hydrogen, halogen, C.sub.Type: GrantFiled: February 21, 1997Date of Patent: October 6, 1998Assignee: SmithKline Beecham p.l.c.Inventor: Laramie Mary Gaster
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Patent number: 5817690Abstract: A compound of the formula I: ##STR1## in which Y is hydrogen, halogen or lower alkoxy; R.sub.1 is hydrogen, lower alkyl or aryl(lower)alkyl; R.sub.2 is hydrogen, lower alkyl or --(CH.sub.2).sub.n X.sub.p Ar, where X is oxygen or carbonyl; Ar is cycloalkyl, aryl or arylaryl, oxindolyl, benzimidazolyl, indolyl, 2-oxobenzimidazolyl or 2-thioxobenzimidazolyl; or R.sub.1 and R.sub.2, taken together with the nitrogen atom to which they are attached, complete a 3,4-dihydro-1H-isoquinolinyl or 1,3-dihydro-isoindolyl; n is one of the integers 1,2,3,4,5 or 6; p is one of the integers 0 or 1; or a pharmaceutically acceptable salt thereof are inhibitors of dopamine synthesis and release, useful in the treatment of schizophrenia, Parkinson's Disease, Tourette's Syndrome, alcohol addiction, cocaine addiction, and addiction to analogous drugs.Type: GrantFiled: August 12, 1997Date of Patent: October 6, 1998Assignee: American Home Products CorporationInventor: Richard Eric Mewshaw
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Patent number: 5776497Abstract: A mineral or organic particle-based product comprising an indoline product, a method for preparing same, and the use thereof in cosmetics. The product is a powder consisting of mineral or organic particles smaller than 200 microns, and comprises, in and/or on the particles, an indoline product obtained by oxidative polymerization using at least one indoline.Type: GrantFiled: June 7, 1995Date of Patent: July 7, 1998Assignee: L'OrealInventors: Alain Lagrange, Herve Andrean, Alex Junino
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Patent number: 5760248Abstract: A description is given of tachykinin receptor antagonists having general formula (I) ##STR1## their preparation and use in pharmaceutical formulations.Type: GrantFiled: May 31, 1996Date of Patent: June 2, 1998Assignee: A.Menarini Industrie Farmaceutiche Riunite S.r.l.Inventors: Alessandro Sisto, Christopher Fincham, Edoardo Potier, Stefano Manzini, Federico Arcamone, Paolo Lombardi
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Patent number: 5728723Abstract: The invention relates to 1-Benzenesulfonyl-1,3-dihydroindol-2-one derivatives of the formula ##STR1## and their salts, where appropriate, to their preparation and to pharmaceutical compositions in which they are present. These compounds have an affinity for the vasopressin and/or ocytocin receptors.Type: GrantFiled: June 7, 1995Date of Patent: March 17, 1998Assignee: SanofiInventors: Alain Di Malta, Loic Foulon, Georges Garcia, Dino Nisato, Richard Roux, Claudine Serradeil-Legal, Gerard Valette, Jean Wagnon
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Patent number: 5726319Abstract: There are disclosed certain compounds identified as substituted dipeptide analogs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. Growth promoting compositions containing such substituted dipeptide analogs as the active ingredient thereof are also disclosed.Type: GrantFiled: August 1, 1995Date of Patent: March 10, 1998Assignee: Merck & Co., Inc.Inventors: Peter Lin, William R. Schoen, Judith M. Pisano, Matthew J. Wyvratt
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Patent number: 5719144Abstract: Fibrinogen receptor antagonists having the formula ##STR1## where L is L is (CH.sub.2).sub.p, where p is 1 or 2; and Z is --CR.sup.1 .dbd.CR.sup.Type: GrantFiled: February 22, 1995Date of Patent: February 17, 1998Assignee: Merck & Co., Inc.Inventors: George D. Hartman, John H. Hutchinson, Wasyl Halczenko
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Patent number: 5717108Abstract: The present invention relates to a novel process for the preparation of a monohydroxyindole or dihydroxyindole compound by a single step of placing in contact, in a solvent medium, at least one hydrolase with at least one indole compound bearing one or two radicals connected by an ester function to the benzene ring.Type: GrantFiled: December 5, 1996Date of Patent: February 10, 1998Assignee: L'OrealInventors: Alain Lagrange, Michel Philippe, Remy Tuloup
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Patent number: 5684033Abstract: This invention provides a novel series of non-peptidyl compounds which are useful in the treatment or prevention of a physiological disorder associated with an excess of tachykinins. This invention also provides methods for the treatment of such physiological disorders as well as pharmaceutical formulations which employ these novel compounds.Type: GrantFiled: June 5, 1995Date of Patent: November 4, 1997Assignee: Eli Lilly and CompanyInventors: Sung Y. Cho, Thomas A. Crowell, Bruce D. Gitter, Philip A. Hipskind, J. Jeffry Howbert, Joseph H. Krushinski, Jr., Karen L. Lobb, Brian S. Muehl, James A. Nixon
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Patent number: 5674811Abstract: A cyanoketone derivatives of the following formula (1) ##STR1## which are characterized by excellent herbicidal activity and effectiveness against a variety of broad leafed weeds, including barnyard grass, green foxtail, velvet leaf, livid amaranth and hairy beggar ticks.Type: GrantFiled: October 6, 1994Date of Patent: October 7, 1997Assignee: Tokuyama CorporationInventors: Toshio Kitajima, Tadashi Kobutani, Shozo Kato, Masao Yamaguchi, Masahiko Ishizaki, deceased
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Patent number: 5635527Abstract: A novel carboxylic acid compound having a condensed ring, which is represented by the formula (I) ##STR1## wherein each symbol is as defined in the specification, a pharmacologically acceptable salt thereof, a pharmaceutical composition thereof and pharmaceutical use thereof. The novel carboxylic acid compound having a condensed ring and pharmacologically acceptable salt thereof of the present invention have superior GPIIb/IIIa antagonism in mammals inclusive of human; can be administered orally; have long life in blood and low toxicity; and show less side-effects. Accordingly, they are extremely useful for the prophylaxis and treatment of thrombotic diseases and other diseases.Type: GrantFiled: February 6, 1996Date of Patent: June 3, 1997Assignee: The Green Cross CorporationInventors: Shinichiro Ono, Tomohiro Yoshida, Atsuyuki Ashimori, Keigo Kosaka, Takehiro Okada, Kazuhiro Maeda, Masahiro Eda, Fumio Mori, Yoshihisa Inoue, Hajime Ebisu, Teruaki Imada, Ruriko Ikegawa, Feng Wang, Norifumi Nakamura
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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: 5629265Abstract: Disclosed herein are cyanoketone derivatives of the following formula (1) ##STR1## such as 1-cyano-1-piperidinocarbonyl-3-[4-(2-chloro-4-trifluoromethylphenoxy)pheno xy]-2-butanone, 1-cyano-1-piperidinocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy )phenoxy]-2-butanone, 1-cyano-1-(N-methyl-N-dichlorophenyl)aminocarbonyl-3-[4-(2-quinoxalyloxy)p henoxy]-2-butanone, 1-cyano-1-(N,N-dibutyl)aminocarbonyl-3-[4-(3-chloro-5-trifluoromethyl-2-py ridyloxy)phenoxy-2-butanone, and the like, which are characterized by excellent herbicidal activity and effectiveness against a variety of gramineous weeds.Type: GrantFiled: June 22, 1994Date of Patent: May 13, 1997Assignee: Tokuyama CorporationInventors: Masahiko Ishizaki, Seiji Nagata, Junji Takenaka
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Patent number: 5622983Abstract: Novel unnatural dipeptoids of .alpha.-substituted Trp-Phe derivatives useful as agents in the treatment of obesity, hypersecretion of gastric acid in the gut, gastrin-dependent tumors, colorectal tumors, or as antipsychotics are disclosed. Further the compounds are antianxiety agents, antiulcer agents, antidepressant agents, and are agents useful for preventing the withdrawal response produced by chronic treatment or use followed by chronic treatment followed by withdrawal from nicotine, diazepam, alcohol, cocaine, caffeine, or opiods. Also disclosed are pharmaceutical compositions and methods of treatment using the dipeptoids as well as processes for preparing them and novel intermediates useful in their preparation. An additional feature of the invention is the use of the subject compounds to prepare pharmaceutical and diagnostic compositions.Type: GrantFiled: May 22, 1995Date of Patent: April 22, 1997Assignee: Warner-Lambert CompanyInventors: David C. Horwell, Martyn C. Pritchard, Edward Roberts, Reginald S. Richardson, Julian Aranda
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Patent number: 5578633Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: June 2, 1995Date of Patent: November 26, 1996Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5567827Abstract: The subject of the invention is 4-hydroxyphenylthio derivatives of general formula: ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, each represent hydrogen, a methyl or ethyl radical or a halogen atom,R represents a (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) cycloalkyl or phenyl radical,R.sub.3 represents hydrogen or a halogen atom,X represents --O--, --S-- or --NR.sub.4 -- in which R.sub.4 represents hydrogen or a (C.sub.1 -C.sub.4) alkyl group,useful as synthetic intermediates, especially for the preparation of aminoalkoxyphenylsulphonyl derivatives which are pharmaceutically active compounds.Type: GrantFiled: June 7, 1995Date of Patent: October 22, 1996Assignee: Elf SanofiInventors: Jean Gubin, Henri Inion
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Patent number: 5565484Abstract: The invention relates to use of at least one indole derivative of general formula: ##STR1## or of one of the pharmaceutically acceptable salts thereof, in which: Am is selected from radical (a) and (b) defined as follows: ##STR2## R is a C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl radical R.sub.1 represents hydrogen or a C.sub.1 -C.sub.4 alkyl radicalR.sub.2 and R.sub.3, which may be identical or different, represent hydrogen, the methyl or ethyl radical or a halogenR.sub.4, R.sub.5 and R.sub.6, which may be identical or different, represent hydrogen, a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy radical or a halogenR.sub.7 represents hydrogen or a halogenR.sub.8 represents hydrogen or a C.sub.1 -C.sub.4 alkyl radicalR.sub.9 represents hydrogen or, when R.sub.8 and R.sub.9 are taken together, form the methylene radicalm represents 1 or 2n represents 2, 3 or 4for preventing or treating diseases involving a proliferation of smooth muscle cells.Type: GrantFiled: July 29, 1994Date of Patent: October 15, 1996Assignee: SanofiInventors: Jean-Marc Herbert, Pierre Chatelain
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Patent number: 5554642Abstract: A compound which is selected from those of formula (I): ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description,its optical isomers and its addition salts thereof with a pharmaceuticaliy-accepable acid or base,and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: May 22, 1995Date of Patent: September 10, 1996Assignee: Adir et CompagnieInventors: Michel Langlois, Pierre Renard, G erard Adam
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Patent number: 5510379Abstract: .beta.-Carboxy sulfonates of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is -O-, -S-, or -NR.sub.2 -, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.Type: GrantFiled: December 19, 1994Date of Patent: April 23, 1996Assignee: Warner-Lambert CompanyInventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5508431Abstract: The subject of the invention is 4-hydroxyphenylthio derivatives of general formula: ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, each represent hydrogen, a methyl or ethyl radical or a halogen atom,R represents a (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) cycloalkyl or phenyl radical,R.sub.3 represents hydrogen or a halogen atom,X represents --O--, --S-- or --NR.sub.4 -- in which R.sub.4 represents hydrogen or a (C.sub.1 -C.sub.4) alkyl group, useful as synthetic intermediates, especially for the preparation of aminoalkoxyphenylsulphonyl derivatives which are pharmaceutically active compounds.Type: GrantFiled: September 8, 1994Date of Patent: April 16, 1996Assignee: Elf SanofiInventors: Jean Gubin, Henri Inion
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Patent number: 5506243Abstract: Since sulfonamide derivatives of the present invention show strong inhibitory activity against cysteine protease such as calpain papain, cathepsin B, cathepsin H, cathepsin L, they can be used as remedies for muscular dystrophy, cataract, myocardial infarction, stroke, Alzheimer's disease, amyotrophia, osteoporosis, hypercalcemia or the like.Type: GrantFiled: April 28, 1994Date of Patent: April 9, 1996Assignee: Mitsubishi Kasei CorporationInventors: Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura
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Patent number: 5502187Abstract: The pharmaceutically active bicyclic heterocyclic amines (XXX) ##STR1## where W.sub.1 is --N.dbd. or --CH.dbd.; W.sub.3 is --N.dbd. or --CH.dbd.; W.sub.5 is --N.dbd. or --CR.sub.5 -- with the proviso that W.sub.5 is --CR.sub.5 -- when both W.sub.1 and W.sub.3 are --N.dbd. which are useful as pharmaceuticals in treating mild and/or moderate to severe head injury, subarachnoid hemorrhage and subsequent ischemic stroke, asthma and reduction of mucous formation/secretion in the lung and other diseases and injuries.Type: GrantFiled: October 3, 1994Date of Patent: March 26, 1996Assignee: The Upjohn CompanyInventors: Donald E. Ayer, Gordon L. Bundy, Eric J. Jacobsen
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Patent number: 5494928Abstract: The invention releates to indole derivatives of the formula ##STR1## wherein R.sup.1 to R.sup.4 are, independently, hydrogen, halogen, lower-alkyl, cycloalkyl or trifluoromethyl, R.sup.5 and R.sup.6 are, independently, hydrogen, halogen, lower-alkyl, cycloalkyl, trifluoromethyl, hydroxy or lower-alkoxy and R.sup.7 is hydrogen or lower-alkyl, andpharmaceutically acceptable acid addition salts thereof.The compounds of formula I bind to serotonin receptors and are therefore useful in the treatment and/or prevention of central nervous system disorders, such as depression.Type: GrantFiled: October 3, 1994Date of Patent: February 27, 1996Assignee: Hoffmann-La Roche Inc.Inventor: Michael Bos
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Patent number: 5482960Abstract: Novel indole and indoline nonpeptide antagonists of endothelin I are described, as well as novel intermediates used in their preparation, methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, essential renovascular malignant and pulmonary hypertension, cerebral infarction, cerebral ischemia, congestive heart failure and subarachnoid hemorrhage.Type: GrantFiled: November 14, 1994Date of Patent: January 9, 1996Assignee: Warner-Lambert CompanyInventors: Kent A. Berryman, Amy M. Bunker, Annette M. Doherty, Jeremy J. Edmunds
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Patent number: 5481002Abstract: There are disclosed compounds ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently of one another hydrogen, a C.sub.1 -C.sub.12 alkyl group, a C.sub.1 -C.sub.12 alkoxy group, a C.sub.5 -C.sub.8 cycloalkyl group, a C.sub.5 -C.sub.8 cycloalkoxy group, a C.sub.5 -C.sub.8 cycloalkylthio group, a C.sub.6 -C.sub.10 aryl group, a C.sub.6 -C.sub.10 aryloxy group, a C.sub.6 -C.sub.10 arylthio group, nitro, halogen, cyano, --COOH, --COOR.sub.7, --NR.sub.8 R.sub.9 or --CONR.sub.8 R.sub.9, where R.sub.7 is C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.8 acycloalkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl, and R.sub.8 and R.sub.9 are each independently of the other hydrogen, C.sub.1 -C.sub.8 alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 alkyl, X is nitrogen or CR.sub.4, Y is nitrogen or CR.sub.5 and Z is nitrogen or CR.sub.6, and R.sub.4, R.sub.5 and R.sub.6 are each independently of one another hydrogen, a straight-chain or branched C.sub.1 -C.sub.12 alkyl group or a C.sub.6 -C.sub.Type: GrantFiled: December 14, 1993Date of Patent: January 2, 1996Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Beat Schmidhalter, Heinz Wolleb
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Patent number: 5472978Abstract: Compounds of formula (I), and salts and prodrugs thereof, wherein Q represents optionally substituted phenyl, naphthyl, indolyl, benzothiophenyl, benzofuranyl, benzyl or indazolyl; Z represents O, S or NR.sup.8 ; X and Y are H or are together .dbd.O; R.sup.1 and R.sup.2 are H; optionally substituted C.sub.1-6 alkyl; optionally substituted phenyl(C.sub.1-4 alkyl); COR.sup.c ; CO.sub.2 R.sup.c ; CONR.sup.c R.sup.d ; CONR.sup.c COOR.sup.d ; or SO.sub.2 R.sup.c ; R.sup.3 is H or C.sub.1-6 alkyl, R.sup.4 is H , C.sub.1-6 alkyl or optionally substituted phenyl; and R.sup.5 represents optionally substituted phenyl; are tachykinin antagonists. They and compositions thereof are useful in therapy.Type: GrantFiled: December 10, 1993Date of Patent: December 5, 1995Assignee: Merck Sharp & Dohme Ltd.Inventors: Raymond Baker, Angus M. MacLeod, Kevin J. Merchant, Christopher J. Swain
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Patent number: 5463061Abstract: A glycide derivative represented by the following general formula (I) is produced by reacting a hydroxyaryl or heteroaryl represented by A-OH with glycidyl tosylate in the presence of a cesium base as a base. Thereby, an aryl glycidyl ether derivative, which is an important intermediate for drug production, can be produced easily and reliably. Particularly when optically active glycidyl tosylate is used, said compound can be obtained at a high optical purity. ##STR1## wherein A represents an aryl group or a heteroaryl group.Type: GrantFiled: January 13, 1994Date of Patent: October 31, 1995Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Nobuyuki Fukazawa, Tsuneji Suzuki, Nobuya Kawauchi, Hironori Komatsu, Kengo Otsuka, Yuki Nakajima
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Patent number: 5461063Abstract: Compounds of formula (I), and salts and prodrugs thereof: ##STR1## wherein X represents O or S;Y represents (CH.sub.2).sub.m, where m is 0 or 1;Z represents (CH.sub.2).sub.n, where n is 0 or 1;R.sup.1 represents optionally substituted phenyl;R.sup.2 is phenyl, naphthyl, indazolyl, thienyl, furyl, pyridyl, thiazolyl, tetrazolyl, quinolyl, benzhydryl or benzyl;R.sup.3 is H, COR.sup.a, CO.sub.2 R.sup.a C(COOR).sub.2, C(CONR.sup.a R.sup.b).sub.2, COCONR.sup.a R.sup.b, COCO.sub.2 R.sup.a, C.sub.1-6 alkyl optionally substituted by a group selected from (CO.sub.2 R.sup.a, CONR.sup.a R.sup.b, hydroxy, cyano, COR.sup.a, NR.sup.a R.sup.b, C(NOH)NR.sup.a R.sup.b, CONHphenyl(C.sub.1-4 alkyl), COCO.sub.2 R.sup.a, C(.dbd.NR.sup.a)NR.sup.b NR.sup.c CO.sub.2 R.sup.d, CONHNR.sup.a R.sup.b, C(S)NR.sup.a R.sup.b, CONR.sup.a C.sub.1-6 alkylR.sup.12, CONR.sup.13 C.sub.2-6 alkynyl, CONR.sup.13 C.sub.2-6 alkenyl, COCONR.sup.a R.sup.b, CONR.sup.a C(NR.sup.b)NR.sup.c R.sup.d, CONR.sup.13 SO.sub.2 R.sup.a, SO.sub.2 R.sup.13 COR.sup.Type: GrantFiled: August 5, 1993Date of Patent: October 24, 1995Assignee: Merck Sharp & Dohme LimitedInventors: Fintan Kelleher, Richard T. Lewis
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Patent number: 5434271Abstract: Disclosed are a novel class of 1-hydroxy-6-organosulphonylindoles and a process for the preparation thereof.Type: GrantFiled: May 16, 1994Date of Patent: July 18, 1995Assignee: Eastman Chemical CompanyInventor: Raymond Fisher
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Patent number: 5424329Abstract: 3-Substituted-indole-2-carboxamides are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases. Certain of these compounds are novel and methods of manufacture are also described.Certain of the indole-2-carboxamides also inhibit the activation of human immunodeficiency virus (HIV), latent in infected humans.Type: GrantFiled: August 18, 1993Date of Patent: June 13, 1995Assignee: Warner-Lambert CompanyInventors: Diane H. Boschelli, David T. Connor, Paul C. Unangst
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Patent number: 5420289Abstract: This invention relates to substituted indole derivatives possessing lipoxygenase inhibitory, phospholipase A.sub.2 inhibitory and leukotriene antagonist activity, which are useful as anti-inflammatory, antiallergic and cytoprotective agents.Type: GrantFiled: March 10, 1993Date of Patent: May 30, 1995Assignee: American Home Products CorporationInventors: John H. Musser, Anthony F. Kreft, III, Amedeo A. Failli, Christopher A. Demerson, Uresh S. Shah, James A. Nelson
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Patent number: 5403933Abstract: The invention relates to indolizine derivatives of general formula: ##STR1## in which: X denotes an --S or --SO.sub.2 -- group, each of R.sub.1 and R.sub.2, which are identical or different, denotes hydrogen, the methyl or ethyl radical or a halogen atom,R.sub.3 denotes hydrogen or a C.sub.1 -C.sub.4 alkyl radical,R.sub.4 denotes a precursor radical of a carboxyl group,R denotes a C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or phenyl radical, and their use as intermediates for the preparation of pharmaceutically active aminoalkoxybenzenesulphonylindolizine derivatives.Type: GrantFiled: June 23, 1993Date of Patent: April 4, 1995Assignee: Elf SanofiInventors: Jean Gubin, Michel Renard
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Patent number: 5401855Abstract: The subject of the invention is 4-hydroxyphenylthio derivatives of general formula: ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, each represent hydrogen, a methyl or ethyl radical or a halogen atom,R represents a (C.sub.1 -C.sub.6) alkyl, (C.sub.3 -C.sub.6) cycloalkyl or phenyl radical,R.sub.3 represents hydrogen or a halogen atom, X represents --O--, --S-- or --NR.sub.4 -- in which R.sub.4 represents hydrogen or a (C.sub.1 -C.sub.4) alkyl group, useful as synthetic intermediates, especially for the preparation of aminoalkoxyphenylsulphonyl derivatives which are pharmaceutically active compounds.Type: GrantFiled: June 23, 1993Date of Patent: March 28, 1995Assignee: Elf SanofiInventors: Jean Gubin, Henri Inion
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Patent number: 5397801Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: May 10, 1994Date of Patent: March 14, 1995Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5395817Abstract: Substituted N-arylindoles, a process for producing them and their use as herbicides. In particular, substituted N-arylindoles of the formula ##STR1## are disclosed in which: R is hydrogen; halogen; nitro; cyano; alkyl; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; carbonylalkoxy; alkyloxyalkoxy; cyanoalkoxy; benzyloxy; alkoxycarbonylalkoxy; alkylcarbonylalkoxy; haloalkyl; hydroxyalkyl; formyl; azido; carboxy or a salt thereof; amino; substituted amino; carboxyamido; substituted carboxyamido; sulfonamido wherein the N is substituted with hydrogen and/or alkyl; or YR.sup.4 wherein Y is O or S(O).sub.m and R.sup.4 is hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxycarbonylalkyl, hydroxycarbonylalkyl or aminocarbonylalkyl; R.sup.1 is hydrogen, alkyl, halogen, cyano, haloalkyl, alkoxy, or carboxy or a salt thereof; X is hydrogen, halogen, cyano, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl or alkoxy; R.sup.3 is hydrogen, haloalkyl, haloalkoxy, cyano, halogen, or SO.sub.y R.sup.5 wherein R.sup.Type: GrantFiled: December 9, 1992Date of Patent: March 7, 1995Assignee: Imperial Chemical Industries PLCInventors: Ference M. Pallos, Christoper J. Mathews
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Patent number: 5384402Abstract: Methine transfer dyes have the formula ##STR1## where L is a bridge member which does not permit any conjugation of .pi.-electrons between Z and Y,X is cyano, C.sub.1 -C.sub.6 -alkoxycarbonyl or C.sub.1 -C.sub.6 -monoalkylcarbamoyl, wherein alkyl may in each case be interrupted by oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkoxycarbonyl, C.sub.5 -C.sub.7 -monocycloalkylcarbamoyl, phenoxycarbonyl or monophenylcarbamoyl, andY and Z are each independently of the other aminophenylene, which may be benzo-fused, or heterocyclyl.Type: GrantFiled: June 7, 1994Date of Patent: January 24, 1995Assignee: BASF AktiengesellschaftInventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens