The -c(=x)- Is Part Of A -c(=x)x- Group, Wherein The X's Are The Same Or Diverse Chalcogens Patents (Class 549/71)
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Patent number: 6492362Abstract: The present invention relates to novel selective cathepsin S inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.Type: GrantFiled: September 15, 2000Date of Patent: December 10, 2002Assignee: Axys Pharmaceuticals, Inc.Inventors: Michael Graupe, John O. Link, John W. Patterson, Sheila Zipfel
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Patent number: 6426359Abstract: This invention relates to the use of EP2 receptor subtype selective prostaglandin E2 agonists to augment bone mass including the prevention and treatment of skeletal disorders in mammals, including humans.Type: GrantFiled: June 11, 1999Date of Patent: July 30, 2002Assignee: Pfizer Inc.Inventors: Kimberly O. Cameron, Hua Z. Ke, Bruce A. Lefker, Robert L Rosati, David D. Thompson
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Patent number: 6403810Abstract: This invention relates to new retinoic acid receptor selective retinoid agonists, to pharmaceutical compositions containing such compounds, and to the use of such retinoic acid receptor agonists, particularly retinoic acid receptor &ggr; (RAR&ggr;) selective agonists, for the treatment of emphysema and related pulmonary diseases.Type: GrantFiled: June 15, 2001Date of Patent: June 11, 2002Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Jean-Marc Lapierre
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Patent number: 6376502Abstract: This invention relates to prostaglandin agonists, methods of using such prostaglandin agonists, pharmaceutical compositions containing such prostaglandin agonists and kits containing such prostaglandin agonists. The prostaglandin agonists are useful for the treatment of bone disorders including osteoporosis.Type: GrantFiled: February 22, 2000Date of Patent: April 23, 2002Assignee: Pfizer Inc.Inventors: Kimberly O. Cameron, Bruce A. Lefker, Robert L. Rosati
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Patent number: 6323214Abstract: The present invention relates to compounds of formulas (IA), (IB), and (IC): the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.Type: GrantFiled: September 17, 1998Date of Patent: November 27, 2001Assignee: Medco Research, IncInventor: Pier Giovanni Baraldi
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Patent number: 6265423Abstract: Novel aromatic polycyclic retinoid-type derivatives of general formula (I), wherein groupings R3 and R4 attached to the double bond between carbons 11 and 12 are cis groupings, and pharmaceutical and cosmetic compositions containing same, are disclosed.Type: GrantFiled: July 15, 1998Date of Patent: July 24, 2001Assignee: Centre Europeen de Bioprospective-CebInventors: Bertrand Leblond, Francis Darro, Abdallah Devine, Véronique Sales-Sallans, Pierre Duhamel, Robert Kiss, Alain-René Schoofs, Pierre Germain, Bernard Pourrias
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Patent number: 6150532Abstract: The present invention relates to novel protein tyrosine phosphatase modulating compounds having the general structure shown in Formula (A1), to methods for their preparation, to compositions comprising the compounds, to their use for treatment of human and animal disorders, to their use for purification of proteins or glycoproteins, and to their use in diagnosis. The invention relates to modulation of the activity of molecules with phosphotyrosine recognition units, including protein tyrosine phosphatases (PTPases) and proteins with Src-homology-2 domains, in in vitro systems, microorganism, eukaryoic cells, whole animals and human being. R' and R" are independently selected from the group consisting of hydrogen, halo, cyano, nitro, trihalomethyl, alkyl, arylalkyl. R'" is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, arylalkyl. X is aryl. Y is selected from hydrogen or ##STR1## wherein (*) indicates a potential point of attachment to X.Type: GrantFiled: December 11, 1998Date of Patent: November 21, 2000Inventors: Adnan Mjalli, Sepehr Sarshar, Xiaodong Cao, Farid Bakir
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Patent number: 6150413Abstract: Novel pharmaceutically/cosmetically-active triaromatic compounds have the structural formula (I): ##STR1## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: May 26, 1998Date of Patent: November 21, 2000Assignee: Centre International de Recherches DermatologiquesInventors: Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 6096901Abstract: A process for the preparation of the compound of the formula: ##STR1## wherein R.sup.1 is OH, which comprises the steps of a) treating the compound of the formula: ##STR2## with an inorganic fluoride, of the formula M.sup.2 F wherein M.sup.2 is an alkali metal cation, at an elevated temperature in the presence of a compound of the formula R.sup.4 P.sup.+ Z.sup.- and a compound of the formula R.sup.5 vic (COW).sub.2 wherein R.sup.4 and R.sup.5 are each selected from optionally substituted (C.sub.6 -C.sub.10) aryl and optionally substituted (C.sub.1 -C.sub.6) alkyl, and W is halo; to form the compound of the formula: ##STR3## and b) I) treating the compound of the formula IV with an aqueous solution of a base, of the formula MOH, wherein M is an alkali metal cation, andii) treating the product of step i) with a mineral acid. A compound of the formula: ##STR4## wherein R.sup.1 is selected from the group consisting of, halo, R.sup.7 O, R.sup.7 COO and N(R.sup.8).sub.2 wherein R.sup.7 is (C.sub.1 -C.sub.Type: GrantFiled: November 30, 1999Date of Patent: August 1, 2000Assignee: Pfizer Inc.Inventors: Anthony Marfat, Robert James Chambers
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Patent number: 6084108Abstract: Fungicides having thiophene rings may be made from the intermediate compound 3-carbomethoxy-4,5-dimethylthiophene. That compound, and related compounds, may be produced by reacting an alpha mercaptoketone, e.g., 3-mercapto-2-butanone, with an acrylate, e.g., methyl-3-methoxy acrylate, in the presence of an alkoxide base, e.g., NaOMe, to form the substituted tetrahydrothiophene, followed by conversion to the aromatic thiophene with an acid treatment. The substituted tetrahydrothiophene is a novel compound.Type: GrantFiled: October 13, 1998Date of Patent: July 4, 2000Assignee: Monsanto CompanyInventors: Thomas L. Fevig, Patrick H. Lau, Wendell G. Phillips
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Patent number: 6057342Abstract: The present application describes amidinophenyl-pyrrolidines, -pyrrolines, and -isoxazolidines and derivatives thereof of formula I: ##STR1## or pharmaceutically acceptable salt forms thereof, wherein one of D and D' may be C(.dbd.NH)NH.sub.2 and the other H, and J.sup.1 and J.sup.2 may be O or CH.sub.2, which are useful as inhibitors of factor Xa.Type: GrantFiled: July 7, 1997Date of Patent: May 2, 2000Assignee: Dupont Pharmaceutical Co.Inventors: John Matthew Fevig, Donald Joseph Phillip Pinto, Mimi Lifen Quan, Petrus Fredericus Wilhelmus Stouten
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Patent number: 6046220Abstract: The invention relates to novel propynyl or dienyl biaromatic compounds which have the general formula (I) ##STR1## as well as to the use of these compounds in pharmaceutical compositions intended for use in human or veterinary medicine (dermatological, rheumatic, respiratory, cardiovascular and ophthalmological complaints in particular), or alternatively in cosmetic compositions.Type: GrantFiled: January 26, 1998Date of Patent: April 4, 2000Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 6043379Abstract: A process for the preparation of the compound of the formula ##STR1## wherein R.sup.1 is OH, which comprises the steps of a) treating the compound of the formula ##STR2## with an inorganic fluoride, of the formula M.sup.2 F wherein M.sup.2 is an alkali metal cation, at an elevated temperature in the presence of a compound of the formula R.sup.4 P.sup.+ Z.sup.- and a compound of the formula R.sup.5 vic (COW).sub.2 wherein R.sup.4 and R.sup.5 are each selected from optionally substituted (C.sub.6 -C.sub.10)aryl and optionally substituted (C.sub.1 -C.sub.6)alkyl, and W is halo; to form the compound of the formula; ##STR3## and b) i) treating the compound of the formula IV with an aqueous solution of a base, of the formula MOH, wherein M is an alkali metal cation, andii) treating the product of step i) with a mineral acid. A compound of the formula ##STR4## wherein R.sup.1 is selected from the group consisting of, halo, R.sup.7 O, R.sup.7 COO and N(R.sup.8).sub.2 wherein R.sup.7 is (C.sub.1 -C.sub.6)alkyl or (C.Type: GrantFiled: July 26, 1999Date of Patent: March 28, 2000Assignee: Pfizer Inc.Inventors: Anthony Marfat, Robert James Chambers
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Patent number: 6034244Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification, have retinoid-like biological activity.Type: GrantFiled: October 15, 1998Date of Patent: March 7, 2000Assignee: Allergan Sales, Inc.Inventors: Min Teng, Tien T. Duong, Roshantha A. Chandraratna
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Patent number: 6025383Abstract: The invention relates to novel thiophene derivatives of the formula (I) ##STR1## in which X represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, nitro or cyano, or two substituents X, together with the carbon atoms to which they are attached, form a saturated or unsaturated, optionally substituted ring,n represents a number from 1 to 3, andZ represents one of the groups ##STR2## in which A, B, D, G, Q.sup.1, Q.sup.2 and Q.sup.3 have the meaning given in the description, to processes for their preparation and to their use as pesticides and herbicides.Type: GrantFiled: June 3, 1998Date of Patent: February 15, 2000Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Jacques Dumas, Thomas Bretschneider, Bernd Gallenkamp, Folker Lieb, Konrad Wernthaler, Christoph Erdelen, Ulrike Wachendorff-Neumann, Norbert Mencke, Andreas Turberg
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Patent number: 6013664Abstract: Novel microbicidal compositions based on thiophene-2-carboxylic acid derivatives, some of which are known, of the formula in whichR.sup.1, R.sup.2 and n have the meanings given in the description, and the use of these substances for controlling undesired microorganisms.Novel thiophene-2-carboxylic acid derivatives of the formula ##STR1## in which R.sup.1, R.sup.2 and p have the meanings given in the description, and a process for the preparation of the substances of the formula (I-a).Type: GrantFiled: May 26, 1999Date of Patent: January 11, 2000Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Norbert Lui, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5981748Abstract: The invention relates to methods of making compounds of the formula VII ##STR1## and their enantiomers, where Ar is a substituted or unsubstituted five- or six-membered aromatic group and B is either an amino acid linked through the amino portion to form an amide or a C.sub.1 -C.sub.6 alcohol linked through the alcohol portion to form an ester. These compounds are advantageously employed as intermediates to prepare optically pure compounds that are active GARFT inhibitors. In one method, a compound of the formula ##STR2## is reacted with a compound of the formula ##STR3## where X is a halogen.Type: GrantFiled: July 2, 1998Date of Patent: November 9, 1999Assignee: Agouron Pharmaceuticals, Inc.Inventors: Michael D. Varney, William H. Romines, Cynthia L. Palmer
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Patent number: 5968910Abstract: A composition and method for the prevention or treatment of HIV-1 infection comprising an HIV-1 reverse transcriptase-inhibiting heterocyclyl carb(ox/thio)anilide compound, a second HIV-1 reverse transcriptase inhibitor compound which does not select for the same HIV-1 mutant strain or strains selected for by the heterocyclyl carb(ox/thio)anilide compound, and, optionally, a third HIV reverse transcriptase inhibitor compound.Type: GrantFiled: November 30, 1994Date of Patent: October 19, 1999Assignee: Jan M. R. BalzariniInventor: Jan Maria Rene Balzarini
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Patent number: 5932595Abstract: The present invention relates to compounds of Formula I: ##STR1## that are matrix metalloprotease inhibitors, pharmaceutical compositions containing them, methods for their use and methods of preparing these compounds.Type: GrantFiled: December 18, 1996Date of Patent: August 3, 1999Assignees: Syntex (U.S.A.) Inc., Agouron Pharmaceuticals, Inc.Inventors: Steven Lee Bender, Chris Allen Broka, Jeffrey Allen Campbell, Arlindo Lucas Castelhano, Lawrence Emerson Fisher, Robert Than Hendricks, Keshab Sarma
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Patent number: 5922767Abstract: Disclosed herein are substituted benzylurea derivatives represented by the following general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are independently H, a halogen atom, or an alkyl or alkoxyl group, R.sup.3 is a phenyl or heterocyclic group which may be substituted, n is an integer of 1-6, and R.sup.4 is a phenyl group which may be substituted, or salts thereof, and medicines comprising such a derivative as an active ingredient. The derivatives or salts thereof strongly inhibit only ACAT in macrophages and are hence useful as prophylactic and therapeutic agents for arteriosclerosis.Type: GrantFiled: October 7, 1997Date of Patent: July 13, 1999Assignee: SS Pharmaceutical Co., Ltd.Inventors: Yoshihiko Kanamaru, Hiroyuki Hirota, Akihiro Shibata, Teruo Komoto, Hiroyuki Naito, Koichi Tachibana, Mari Ohtsuka, Fumio Ishii, Susumu Sato
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Patent number: 5892091Abstract: A catalyst composed of an organic phosphorus compound having a trivalent or pentavalent phosphorus atom and at least one carbon-phosphorus bonding or a combination of the organic phosphorus compound and a halogen atom-containing compound is effective for decarbonylation, that is, for releasing carbon monoxide from a compound containing a moiety of --CO--CO--O-- in its molecular structure.Type: GrantFiled: July 8, 1997Date of Patent: April 6, 1999Assignee: Ube Industries, Ltd.Inventors: Katsumasa Harada, Yoichi Imbe, Keigo Nishihira, Shuji Tanaka, Satoru Fujitsu, Ryoji Sugise, Koichi Kashiwagi, Toshihiko Sumida, Takashi Doi, Masayuki Nishio
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Patent number: 5861421Abstract: This invention relates to derivatives of 4,4-(disubstituted)cyclohexan-1-ones and related compounds which are useful for treating allergic and inflammatory diseases.Type: GrantFiled: June 23, 1997Date of Patent: January 19, 1999Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski, M. Dominic Ryan, Paul E. Bender
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Patent number: 5856323Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i. e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: June 7, 1995Date of Patent: January 5, 1999Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5837725Abstract: Bridged bicyclic aromatic compounds are provided having the structure ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and n are as defined herein. The novel compounds are useful for modulating gene expression of retinoic acid receptors, vitamin D receptors and thyroid receptors. Pharmaceutical compositions and methods for modulating gene expression are provided as well.Type: GrantFiled: May 24, 1995Date of Patent: November 17, 1998Assignees: SRI International, La Jolla Cancer Research FoundationInventors: Marcia I. Dawson, James F. Cameron, Peter D. Hobbs, Ling Jong, Magnus Pfahl, Xiao-kun Zhang, Jurgen M. Lehmann
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Patent number: 5834468Abstract: This invention relates to substituted and unsubstituted ???(aryl- and heteroaryl-) alkyl-, alkyloxy-, alkylthio-, oxo-, thio-, and alkylamino!- heteroaryl and aryl!- alkylamino-, aminoalkyl-, alkyloxy-, and alkylthio!- aryl and heteroaryl compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof, which are useful as antagonists of the pain enhancing effects of E-type prostaglandins, to processes for the preparation of such compounds, to pharmaceutical compositions comprising such compounds, and to methods for treating pain comprising the administration of such compounds.Type: GrantFiled: July 2, 1996Date of Patent: November 10, 1998Assignee: Zeneca LimitedInventors: Gloria Anne Breault, John Oldfield, Howard Tucker, Peter Warner
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Patent number: 5831100Abstract: The invention relates to methods of making compounds of the formula VII ##STR1## and their enantiomers, where Ar is a substituted or unsubstituted five- or six-membered aromatic group and B is either an amino acid linked through the amino portion to form an amide or a C.sub.1 -C.sub.6 alcohol linked through the alcohol portion to form an ester. These compounds are advantageously employed as intermediates to prepare optically pure compounds that are active GARFT inhibitors. In one method, a compound of the formula ##STR2## is reacted with a compound of the formula ##STR3## where X is a halogen.Type: GrantFiled: June 7, 1995Date of Patent: November 3, 1998Assignee: Agouron Pharmaceuticals, Inc.Inventors: Michael D. Varney, William H. Romines, Cynthia L. Palmer
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Patent number: 5808124Abstract: Compounds of the formula ##STR1## where the symbols have the meaning described in the application, have retinoid-like or retinoid antagonist-like biological activity.Type: GrantFiled: June 21, 1996Date of Patent: September 15, 1998Assignee: AllerganInventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5789437Abstract: New microbicidal compositions based on dibromo-thiophene-carboxylic acid derivatives which are known in some cases, of the formula ##STR1## in which R represents the groups --XR.sup.1, --NR.sup.2 R.sup.3, --NR.sup.4 OR.sup.5 or --NR.sup.4 --N(R.sup.5).sub.2, whereX represents oxygen or sulphur andR.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings indicated in the description, and the use of these substances for controlling undesired microorganisms.New dibromo-thiophene-carboxylic acid derivatives of the formula ##STR2## in which R.sup.9 represents the groups --SR.sup.1, --OR.sup.10, ##STR3## in which R.sup.1, R.sup.4, R.sup.5, R.sup.10, R.sup.11, R.sup.12 and R.sup.13 have the meaning indicated in the description, and processes for the preparation of the substances of the formula (I-A).Type: GrantFiled: October 4, 1996Date of Patent: August 4, 1998Assignee: Bayer AktiengesellschaftInventors: Hans-Ludwig Elbe, Lutz Assmann, Ralf Tiemann, Uta Ecker, Gerd Hanssler, Heinz-Wilhelm Dehne
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Patent number: 5786379Abstract: Novel pharmaceutically/cosmetically-active adamantyl-substituted biaromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a')-(f'): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular, bone and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 2, 1996Date of Patent: July 28, 1998Assignee: Centre International de Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5747518Abstract: The substituted thiophene derivative of the invention which is represented by the general formula (1) has a broad disease spectrum for a pathogenic fungus of various crops, exhibits an excellent controlling effect on disease such as gray mold, powdery mildew and rust in particular, and is also effective for a resistant fungus of conventional fungicides which has become a serious problem, and consequently is useful for an agricultural and horticultural fungicide.Type: GrantFiled: April 3, 1996Date of Patent: May 5, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yukihiro Yoshikawa, Kanji Tomiya, Hiroyuki Katsuta, Hideo Kawashima, Osamu Takahashi, Shunichi Inami, Yuji Yanase, Junro Kishi, Hitoshi Shimotori, Naofumi Tomura
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Patent number: 5739352Abstract: This invention relates to a process for preparing carboxylic acids by oxidizing an aldehyde with a peracid in the presence of an amine and/or amine N-oxide catalyst selected from the group consisting of a substituted or unsubstituted alkyl amine, alkyl amine N-oxide, aromatic amine, aromatic amine N-oxide, heterocyclic amine, heterocyclic amine N-oxide and mixtures thereof, to produce the carboxylic acid. Such carboxylic acids have utility for example as chemical intermediates.Type: GrantFiled: October 19, 1995Date of Patent: April 14, 1998Assignee: United Carbide Chemicals & Plastics Technology CorporationInventors: Bruce Armin Barner, Jonathan Joshua Kurland
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Patent number: 5716624Abstract: Novel pharmaceutically/cosmetically-active polyaromatic propynyl compounds have the structural formula (1): ##STR1## in which X is one of the radicals: ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: December 15, 1994Date of Patent: February 10, 1998Assignee: C.I.R.D. GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5712393Abstract: The present invention provides a compound of formula (1) ##STR1## in which: R.sub.4 represents a hydrogen atom, a halogen atom or a nitro group;R.sub.6 represents a hydrogen atom or a straight or branched (C.sub.1 -C.sub.6) alkyl group;R.sub.7 represents a chlorine atom or a hydroxyl group; andZ represents: a phenyl group optionally substituted with one or more halogen atoms, straight or branched (C.sub.1 -C.sub.4)alkyl groups, straight or branched (C.sub.1 -C.sub.4)alkoxy groups, or trifluoromethyl, formyl, --CH.sub.2 OR, --CH.sub.2 OCOR, --CH.sub.2 CONRR', --CH.sub.2 ONCOR, --COOR, nitro, --NHR, --NRR' or --NHCOR groups, wherein R and R' are each, independently, a hydrogen atom or a (C.sub.1 -C.sub.7) alkyl group; a heterocyclic group optionally substituted as defined above for phenyl; or a cyclo(C.sub.5 -C.sub.8)alkyl group; additionally, when R.sub.Type: GrantFiled: November 24, 1995Date of Patent: January 27, 1998Assignee: SynthelaboInventors: Jean Michel Altenburger, Gilbert Lassalle
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Patent number: 5709935Abstract: Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.Type: GrantFiled: February 23, 1996Date of Patent: January 20, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
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Patent number: 5710173Abstract: The present invention relates to molecules capable of modulating tyrosine signal transduction to prevent and treat cell proliferative disorders or cell differentiation disorders associated with particular tyrosine kinases by inhibiting one or more abnormal tyrosine kinase activities.Type: GrantFiled: June 7, 1995Date of Patent: January 20, 1998Assignee: Sugen, Inc.Inventors: Peng Cho Tang, Asaad S. Nematalla, Gerald McMahon
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Patent number: 5688969Abstract: The invention relates to a process for the preparation of thiophene-2,5-dicarboxylic acid by reacting thionyl chloride and adipic acid, with pyridine as catalyst, which process comprisesA) adding 1 part of adipic acid to 3 to 6 parts of thionyl chloride, mixed with a catalytic amount of pyridine,B) adding a further 4 to 7 parts of thionyl chloride in the temperature range from 85.degree. to 95.degree. C.,C) removing excess thionyl chloride and volatile by-products under reduced pressure, andD) bringing the reaction to completion in the temperature range from 140.degree. to 160.degree. C., andE) preparing a salt of thiophene-2,5-dicarboxylic acid by hydrolysing the chloride obtained with an aqueous solution of an alkaline earth metal hydroxide or an alkali metal hydroxide, andF) obtaining the free acid from this salt with a mineral acid.Type: GrantFiled: November 18, 1996Date of Patent: November 18, 1997Assignee: Ciba Specialty Chemicals CorporationInventor: Ivan Orban
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Patent number: 5648486Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes, 2,4-diaryl pyrrolidines, and 2,5-diaryl pyrrolidines are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i.e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase.A method to treat disorders mediated by PAF or leukotrienes is also disclosed, that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier.Type: GrantFiled: May 12, 1993Date of Patent: July 15, 1997Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5648502Abstract: 4-Chloro-2-thiophenecarboxylic acid is made by forming a compound of formula (Ia), disclosed herein, wherein R.sup.3 is (C.sub.1 -C.sub.6) alkyl, phenyl, or benzyl; converting the compound to a compound of formula (IVa), disclosed herein, and removing the silyl group R.sub.3 Si--. The product is useful as an intermediate in making pharmaceutical products.Type: GrantFiled: July 7, 1995Date of Patent: July 15, 1997Assignee: Pfizer Inc.Inventors: Laurence E. Burgess, Gary R. Schulte
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Patent number: 5618931Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning described in the specification have retinoid-like biological activity.Type: GrantFiled: December 29, 1994Date of Patent: April 8, 1997Assignee: AllerganInventors: Richard L. Beard, Min Teng, Alan T. Johnson, Vidyasagar Vuligonda, Roshantha A. Chandraratna
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Patent number: 5610319Abstract: The invention generally relates to compounds of the formula I, which are in equilibrium with their 4-hydroxy tautomers, and their pharmaceutically acceptable salts: ##STR1## where n is 0 to 2; A is S, CH.sub.2, O, NH or Se, and when n is 0, A is not CH.sub.2, and when n is 1, A is not CH.sub.2 or NH; X is a substituted or unsubstituted C.sub.1 -C.sub.3 alkyl, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl or amino, or sulfur or oxygen; Ar is a substituted or unsubstituted monocyclic carbocycle or heterocycle, or fused or nonfused polycyclic carbocycle or heterocycle; and R.sub.1 and R.sub.2 are hydrogen or a moiety that forms together with the attached CO.sub.2 a readily hydrolyzable ester group. These compounds and their salts are useful as inhibitors of GARFT or as antiproliferative agents. The invention also pertains to pharmaceutical compositions and methods employing such Compounds as GARFT inhibitors or antiproliferative agents.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: Agouron Pharmaceuticals, Inc.Inventors: Michael D. Varney, William H. Romines, Cynthia L. Palmer
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Patent number: 5604256Abstract: Compounds of formula (I): ##STR1## (in which: R is hydrogen, methyl or hydroxy; X is alkyl, alkenyl, cycloalkyl, aryl, aralkyl, or a heterocyclic group; A is a single bond, or an alkylene, alkenylene, alkynylene or alkadienylene group; Y is hydrogen, aryl, cycloalkyl or a heterocyclic group) have the ability to inhibit the biosynthesis of cholesterol, and can thus be used for the treatment and prophylaxis of diseases relating to high blood cholesterol levels.Type: GrantFiled: December 14, 1994Date of Patent: February 18, 1997Assignee: Sankyo Company, LimitedInventors: Hiroshi Kogen, Masaaki Kurabayashi, Teiichiro Koga, Toru Komai, Haruo Iwabuchi
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Patent number: 5602104Abstract: A polycyclic aromatic compound having the formula ##STR1## and its salts have useful therapeutic and cosmetic action particularly in psoriasis. In the formula,X represents --CH.dbd.CH--, O or S,R.sub.1 represents hydrogen, branched alkyl having 3-15 carbon atoms, alkoxy having 1-6 carbon atoms or 1-adamantyl, R.sub.2 represents hydroxy, hydrogen, linear or branched alkyl having 1-15 carbon atoms Or alkoxy having 1-6 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, or R.sub.1 and R.sub.2 together with the adjacent carbon atoms of the naphthalene ring form a 5 or 6 chain ring optionally substituted by at least one lower alkyl radical, or interrupted by an oxygen atom,R.sub.3 represents --CH.sub.2 OH or --COR.sub.4, or --CH.sub.3 when R.sub.1 and R.sub.2 taken together form a 5 or 6 chain ring,R.sub.4 represents --OR.sub.5 or ##STR2## R.sub.Type: GrantFiled: April 13, 1995Date of Patent: February 11, 1997Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Braham Shroot, Jacques Eustache, Oliver Watts, Jean-Michel Bernardon, Philippe Nedoncelle
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Patent number: 5597839Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: April 28, 1995Date of Patent: January 28, 1997Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5594152Abstract: This invention comprises a process for production of a compound of the formula: ##STR1## in which R.sup.1 is selected from the group consisting of H, lower alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3), bromo, chloro, fluoro, iodo, --COlower alkyl(C.sub.1 -C.sub.3), and --CF.sub.3 ;R.sup.2 is selected from the group consisting of H, lower alkyl(C.sub.1 -C.sub.3), alkoxy(C.sub.1 -C.sub.3), amino, bromo, chloro, fluoro, iodo, and --COlower alkyl(C.sub.1 -C.sub.3);or R.sup.1 and R.sup.2 taken together are methylenedioxy or ethylenedioxy;R.sup.3 is an aldehyde or carboxcylic acid moiety;the moiety ##STR2## wherein Z represents substituted or unsubstituted phenyl ring or an optionally substituted 5 or 6-membered aromatic heterocyclic ring.Type: GrantFiled: March 10, 1995Date of Patent: January 14, 1997Assignee: American Cyanamid CompanyInventors: Aranapakam M. Venkatesan, Jay D. Albright
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Patent number: 5591858Abstract: Compounds of the formula ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, R.sub.19, Y, A, B, m and o have the meaning described in the specification have retinoid like biological activity.Type: GrantFiled: February 27, 1996Date of Patent: January 7, 1997Assignee: AllerganInventors: Vidyasagar Vuligonda, Min Teng, Richard L. Beard, Alan T. Johnson, Tien T. Duong, Yuan Lin, Roshantha A. Chandraratna
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Patent number: 5591756Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH--, or --CH.dbd.N--;wherein R.sup.1 is --CO.sub.2 R.sup.2 or tetrazole;wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R is an alkyl of from 1 to 20 carbons, --(CH.sub.2).sub.p CF.sub.3 or --(CH.sub.2).sub.q R.sup.3 wherein R.sup.3 is alkoxy, phenoxy or alkoxy substituted phenoxy wherein the alkoxy group has from 1 to 8 carbons;wherein p and q are integers from 0 to 20;wherein n is 0 or 1; andwherein m is 0, 1, 2, or 3.Type: GrantFiled: May 19, 1995Date of Patent: January 7, 1997Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5543534Abstract: Compounds of Formula 1 ##STR1## wherein X is S or O; R.sub.1 -R.sub.5, m, o, X, Y, A, B are as defined in the specification.Type: GrantFiled: December 29, 1994Date of Patent: August 6, 1996Assignee: AllerganInventors: Vidyasagar Vuligonda, Min Teng, Richard L. Beard, Alan T. Johnson, Yuan Lin, Roshantha A. Chandraratna
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Patent number: 5527829Abstract: HIV protease inhibitors, obtainable by chemical synthesis, inhibit or block the biological activity of the HIV protease enzyme, causing the replication of the HIV virus to terminate. These compounds, as well as pharmaceutical compositions that contain these compounds and optionally other anti-viral agents as active ingredients, are suitable for treating patients or hosts infected with the HIV virus, which is known to cause AIDS.Type: GrantFiled: May 23, 1994Date of Patent: June 18, 1996Assignee: Agouron Pharmaceuticals, Inc.Inventor: Vincent J. Kalish
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Patent number: 5493047Abstract: The invention relates to a method of preparing an optically active cyanohydrin carboxylic acid ester from an optically active cyanohydrin of opposite configuration, wherein said starting cyanohydrin is converted with a carboxylic acid in the presence of a dialkyl azodicarboxylate and a triarylphosphine.The invention also relates to a method of preparing an optically active cyanohydrin of opposite configuration by a subsequent solvolysis of the ester obtained under conservation of the configuration.Type: GrantFiled: December 6, 1993Date of Patent: February 20, 1996Assignee: Duphar International Research B.V.Inventors: Johannes Brussee, Arne Van Der Gen, Erwin G. J. C. Warmerdam, Chris G. Kruse
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Patent number: 5475022Abstract: Compounds of Formula 1 ##STR1## wherein m is 1-4; R.sub.1 --R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, or I; R.sub.5 is hydrogen, lower alkyl of 1 to 6 carbons, Cl, Br, I, lower alkoxy or lower thioalkoxy of 1-6 carbons; R.sub.6 is hydrogen, lower alkyl, Cl, Br, I, OR.sub.11, SR.sub.11, OCOR.sub.11, SCOR.sub.11, NH2, NHR.sub.11, N(R.sub.11).sub.2, NHCOR.sub.11 OR NR.sub.11 --COR.sub.11 ; R.sub.20 is independently hydrogen or lower alkyl; Y is an aromatic group such as phenyl or naphthyl, or a heteroaryl group selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl and oxazolyl; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3-6 carbons, cycloalkyl having 3-6 carbons, alkenyl having 2-6 carbons and 1 or 2 double bonds, alkynyl having 2-6 carbons and 1 or 2 triple bonds; B is hydrogen, COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.Type: GrantFiled: October 18, 1993Date of Patent: December 12, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. Chandraratna