Chalcogen Bonded Directly To Ring Carbon Of The Five-membered Hetero Ring (e.g., 3-indolols, Etc.) Patents (Class 548/484)
  • Patent number: 6166040
    Abstract: 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: Grant
    Filed: May 11, 1999
    Date of Patent: December 26, 2000
    Assignee: Eli Lilly and Company Limited
    Inventors: John Fairhurst, Peter Thaddeus Gallagher, Martin Victor Miles, William Martin Owton, Colin William Smith
  • Patent number: 6150394
    Abstract: Compounds having a metalloproteinase inhibitory activity, represented by the formula (I), its optically active isomers, their pharmaceutically acceptable salts, or hydrates thereof.
    Type: Grant
    Filed: July 22, 1998
    Date of Patent: November 21, 2000
    Assignee: Shionogi & Co., Ltd.
    Inventors: Fumihiko Watanabe, Hiroshige Tsuzuki, Mitsuaki Ohtani
  • Patent number: 6147105
    Abstract: 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: Grant
    Filed: May 14, 1997
    Date of Patent: November 14, 2000
    Assignee: Schering Aktiengesellschaft
    Inventors: Erwin Von Angerer, Christian Biberger, Martin Schneider
  • Patent number: 6063806
    Abstract: 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: Grant
    Filed: April 3, 1998
    Date of Patent: May 16, 2000
    Assignee: Kyoto Pharmaceutical Industries, Ltd.
    Inventors: Shoji Kamiya, Hiroaki Shirahase, Hiroshi Matsui, Shohei Nakamura, Katsuo Wada
  • Patent number: 6043257
    Abstract: 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: Grant
    Filed: October 21, 1998
    Date of Patent: March 28, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Celia Dominguez, Qi Han, Daniel Emmett Duffy, Jeongsook Maria Park, Mimi Lifen Quan, Karen Anita Rossi, Ruth Richmond Wexler
  • Patent number: 6004933
    Abstract: 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: Grant
    Filed: April 23, 1998
    Date of Patent: December 21, 1999
    Assignee: Cortech Inc.
    Inventors: Lyle W. Spruce, Albert C. Gyorkos, John C. Cheronis, Val S. Goodfellow, Axel H. Leimer, John M. Young, James Ivan Gerrity
  • Patent number: 6002018
    Abstract: 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: Grant
    Filed: January 28, 1998
    Date of Patent: December 14, 1999
    Assignee: L'Oreal
    Inventors: Eric Terranova, Aziz Fadli, Alain Lagrange
  • Patent number: 5994546
    Abstract: 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: Grant
    Filed: February 11, 1998
    Date of Patent: November 30, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keizo Kimura, Shigeo Hirano, Hiroshi Kawamoto
  • Patent number: 5948808
    Abstract: 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: Grant
    Filed: March 7, 1997
    Date of Patent: September 7, 1999
    Assignee: The Texas A&M University System
    Inventor: Stephen H. Safe
  • Patent number: 5932731
    Abstract: 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: Grant
    Filed: December 22, 1997
    Date of Patent: August 3, 1999
    Assignee: Sumitomo Seika Chemicals Co., Ltd.
    Inventors: Hiroshi Goda, Mikio Yamamoto, Jun-ichi Sakamoto, Hitoshi Karino
  • Patent number: 5925651
    Abstract: 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: Grant
    Filed: April 1, 1997
    Date of Patent: July 20, 1999
    Assignee: Merck & Co., Inc.
    Inventor: John H. Hutchinson
  • Patent number: 5922716
    Abstract: 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: Grant
    Filed: September 27, 1996
    Date of Patent: July 13, 1999
    Assignee: 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
  • Patent number: 5885967
    Abstract: This invention relates to peptide derivatives, pharmaceutical formulations containing those compound and methods of their use as thrombin inhibitors.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: March 23, 1999
    Assignee: Eli Lilly and Company
    Inventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
  • Patent number: 5840984
    Abstract: 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: Grant
    Filed: June 23, 1997
    Date of Patent: November 24, 1998
    Assignee: Albemarle Corporation
    Inventors: Gregory H. Lambeth, Paul L. Wiggins, William R. Brown
  • Patent number: 5817833
    Abstract: 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: Grant
    Filed: February 21, 1997
    Date of Patent: October 6, 1998
    Assignee: SmithKline Beecham p.l.c.
    Inventor: Laramie Mary Gaster
  • Patent number: 5817690
    Abstract: 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: Grant
    Filed: August 12, 1997
    Date of Patent: October 6, 1998
    Assignee: American Home Products Corporation
    Inventor: Richard Eric Mewshaw
  • Patent number: 5776497
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 7, 1998
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Herve Andrean, Alex Junino
  • Patent number: 5760248
    Abstract: A description is given of tachykinin receptor antagonists having general formula (I) ##STR1## their preparation and use in pharmaceutical formulations.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: June 2, 1998
    Assignee: A.Menarini Industrie Farmaceutiche Riunite S.r.l.
    Inventors: Alessandro Sisto, Christopher Fincham, Edoardo Potier, Stefano Manzini, Federico Arcamone, Paolo Lombardi
  • Patent number: 5728723
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: March 17, 1998
    Assignee: Sanofi
    Inventors: Alain Di Malta, Loic Foulon, Georges Garcia, Dino Nisato, Richard Roux, Claudine Serradeil-Legal, Gerard Valette, Jean Wagnon
  • Patent number: 5726319
    Abstract: 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: Grant
    Filed: August 1, 1995
    Date of Patent: March 10, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Peter Lin, William R. Schoen, Judith M. Pisano, Matthew J. Wyvratt
  • Patent number: 5719144
    Abstract: 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: Grant
    Filed: February 22, 1995
    Date of Patent: February 17, 1998
    Assignee: Merck & Co., Inc.
    Inventors: George D. Hartman, John H. Hutchinson, Wasyl Halczenko
  • Patent number: 5717108
    Abstract: 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: Grant
    Filed: December 5, 1996
    Date of Patent: February 10, 1998
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Michel Philippe, Remy Tuloup
  • Patent number: 5684033
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: November 4, 1997
    Assignee: Eli Lilly and Company
    Inventors: 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
  • Patent number: 5674811
    Abstract: 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: Grant
    Filed: October 6, 1994
    Date of Patent: October 7, 1997
    Assignee: Tokuyama Corporation
    Inventors: Toshio Kitajima, Tadashi Kobutani, Shozo Kato, Masao Yamaguchi, Masahiko Ishizaki, deceased
  • Patent number: 5635527
    Abstract: 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: Grant
    Filed: February 6, 1996
    Date of Patent: June 3, 1997
    Assignee: The Green Cross Corporation
    Inventors: 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
  • Patent number: 5631381
    Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: May 20, 1997
    Assignee: Rhone-Poulenc Inc.
    Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
  • Patent number: 5629265
    Abstract: 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: Grant
    Filed: June 22, 1994
    Date of Patent: May 13, 1997
    Assignee: Tokuyama Corporation
    Inventors: Masahiko Ishizaki, Seiji Nagata, Junji Takenaka
  • Patent number: 5622983
    Abstract: 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: Grant
    Filed: May 22, 1995
    Date of Patent: April 22, 1997
    Assignee: Warner-Lambert Company
    Inventors: David C. Horwell, Martyn C. Pritchard, Edward Roberts, Reginald S. Richardson, Julian Aranda
  • Patent number: 5578633
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: November 26, 1996
    Assignee: Sanofi
    Inventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
  • Patent number: 5567827
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: October 22, 1996
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Henri Inion
  • Patent number: 5565484
    Abstract: 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: Grant
    Filed: July 29, 1994
    Date of Patent: October 15, 1996
    Assignee: Sanofi
    Inventors: Jean-Marc Herbert, Pierre Chatelain
  • Patent number: 5554642
    Abstract: 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: Grant
    Filed: May 22, 1995
    Date of Patent: September 10, 1996
    Assignee: Adir et Compagnie
    Inventors: Michel Langlois, Pierre Renard, G erard Adam
  • Patent number: 5510379
    Abstract: .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: Grant
    Filed: December 19, 1994
    Date of Patent: April 23, 1996
    Assignee: Warner-Lambert Company
    Inventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
  • Patent number: 5508431
    Abstract: 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: Grant
    Filed: September 8, 1994
    Date of Patent: April 16, 1996
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Henri Inion
  • Patent number: 5506243
    Abstract: 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: Grant
    Filed: April 28, 1994
    Date of Patent: April 9, 1996
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura
  • Patent number: 5502187
    Abstract: 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: Grant
    Filed: October 3, 1994
    Date of Patent: March 26, 1996
    Assignee: The Upjohn Company
    Inventors: Donald E. Ayer, Gordon L. Bundy, Eric J. Jacobsen
  • Patent number: 5494928
    Abstract: 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: Grant
    Filed: October 3, 1994
    Date of Patent: February 27, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Bos
  • Patent number: 5482960
    Abstract: 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: Grant
    Filed: November 14, 1994
    Date of Patent: January 9, 1996
    Assignee: Warner-Lambert Company
    Inventors: Kent A. Berryman, Amy M. Bunker, Annette M. Doherty, Jeremy J. Edmunds
  • Patent number: 5481002
    Abstract: 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: Grant
    Filed: December 14, 1993
    Date of Patent: January 2, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Beat Schmidhalter, Heinz Wolleb
  • Patent number: 5472978
    Abstract: 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: Grant
    Filed: December 10, 1993
    Date of Patent: December 5, 1995
    Assignee: Merck Sharp & Dohme Ltd.
    Inventors: Raymond Baker, Angus M. MacLeod, Kevin J. Merchant, Christopher J. Swain
  • Patent number: 5463061
    Abstract: 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: Grant
    Filed: January 13, 1994
    Date of Patent: October 31, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Tsuneji Suzuki, Nobuya Kawauchi, Hironori Komatsu, Kengo Otsuka, Yuki Nakajima
  • Patent number: 5461063
    Abstract: 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: Grant
    Filed: August 5, 1993
    Date of Patent: October 24, 1995
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Fintan Kelleher, Richard T. Lewis
  • Patent number: 5434271
    Abstract: Disclosed are a novel class of 1-hydroxy-6-organosulphonylindoles and a process for the preparation thereof.
    Type: Grant
    Filed: May 16, 1994
    Date of Patent: July 18, 1995
    Assignee: Eastman Chemical Company
    Inventor: Raymond Fisher
  • Patent number: 5424329
    Abstract: 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: Grant
    Filed: August 18, 1993
    Date of Patent: June 13, 1995
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Paul C. Unangst
  • Patent number: 5420289
    Abstract: 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: Grant
    Filed: March 10, 1993
    Date of Patent: May 30, 1995
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Anthony F. Kreft, III, Amedeo A. Failli, Christopher A. Demerson, Uresh S. Shah, James A. Nelson
  • Patent number: 5403933
    Abstract: 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: Grant
    Filed: June 23, 1993
    Date of Patent: April 4, 1995
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Michel Renard
  • Patent number: 5401855
    Abstract: 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: Grant
    Filed: June 23, 1993
    Date of Patent: March 28, 1995
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Henri Inion
  • Patent number: 5397801
    Abstract: 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: Grant
    Filed: May 10, 1994
    Date of Patent: March 14, 1995
    Assignee: Sanofi
    Inventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
  • Patent number: 5395817
    Abstract: 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: Grant
    Filed: December 9, 1992
    Date of Patent: March 7, 1995
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ference M. Pallos, Christoper J. Mathews
  • Patent number: 5384402
    Abstract: 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: Grant
    Filed: June 7, 1994
    Date of Patent: January 24, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens