The Chalcogen, X, Is In A -c(=x)- Group Patents (Class 549/498)
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Patent number: 5703017Abstract: 3-(Het)arylcarboxylic acid derivatives of the formula I ##STR1## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and the other substituents have the following meanings:R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio;X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms an alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;R.sup.4 is phenyl or naphthyl, each of which is unsubstituted or substituted or an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom;R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or phenyl;R.sup.6 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.Type: GrantFiled: October 19, 1995Date of Patent: December 30, 1997Assignee: BASF AktiengesellschaftInventors: Ernst Baumann, Joachim Rheinheimer, Uwe Josef Vogelbacher, Matthias Bratz, Hans Theobald, Matthias Gerber, Karl-Otto Westphalen, Helmut Walter, Wilhelm Rademacher
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Patent number: 5684206Abstract: Novel .beta.-aminovinyl ketones of the general formula ##STR1## wherein R.sup.1 is, in particular, an alkenyl, alkynyl, cycloalkyl or cycloalkenyl group; R.sup.2 is, in particular, an electron-attracting substituent such as nitro, acyl, ester, alkylthio, carbamoyl, thiocarbamoyl or haloalkyl; R.sup.3 is, in particular, an alkyl or alkoxy group or a halogen atom; n is 1 or 2 and m is 0, 1, 2 or 3. A method for preparing such compounds by carrying out a condensation reaction between ketone R.sup.1 --CO--CH.sub.3 and, in particular, benzonitrile substituted by (R.sup.2).sub.n and optionally (R.sup.3).sub.m, in the presence of a strong base, as well as a process employing said .beta.-aminovinyl ketones of general formula (VI) for preparing the corresponding .beta.-diketones, are also disclosed.Type: GrantFiled: March 20, 1996Date of Patent: November 4, 1997Assignee: Rhone-Poulenc ArgochimieInventors: Michel Casado, Pierre Le Roy, Virginie Pevere
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Patent number: 5681848Abstract: The invention relates to 7-?5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxycyclopentyl(enyl)!heptanoic or heptenoic acids and derivatives of said adds, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.Type: GrantFiled: November 4, 1996Date of Patent: October 28, 1997Assignee: AllerganInventor: Robert M. Burk
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Patent number: 5672583Abstract: Novel Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. The matrix metalloendoproteinases are a family of zinc-containing proteinases including but not limited to stromelysin, collagenase, and gelatinase, that are capable of degrading the major components of articular cartilage and basement membranes. The inhibitors claimed herein may also be useful in preventing the pathological sequelae following a traumatic injury that could lead to a permanent disability. These compounds may also have utility as a means for birth control by preventing ovulation or implantation.Type: GrantFiled: May 17, 1995Date of Patent: September 30, 1997Assignee: Merck & Co., Inc.Inventors: Kevin Chapman, William Hagmann, Philippe Durette, Craig Esser, Ihor Kopka, Charles Caldwell
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Patent number: 5663367Abstract: Compounds of Formula 1 ##STR1## wherein Z is selected from the group consisting of the radicals shown in Formula 2 and in Formula 3, ##STR2## Y is cycloalkyl or cycloalkenyl of 3 to 8 carbons optionally substituted with one or two R.sub.4 groups, or Y is selected from phenyl, pyridyl, thienyl, furyl, pyrrolyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, oxazolyl, and imidazolyl, said groups being optionally substituted with one or two R.sub.4 groups, the divalent Y radical being substituted by the Z and --CR.sub.1 .dbd.CR.sub.1 --CR.sub.1 .dbd.CR.sub.1 groups on adjacent carbons; X is S, O, or NR.sub.5 ; n is 1 or 2; R.sub.1 and R.sub.2 independently are H, lower alkyl or fluoroalkyl; R.sub.3 is hydrogen, lower alkyl, Cl or Br; R.sub.4 is lower alkyl, fluoroalkyl or halogen; R.sub.5 is H or lower alkyl, and 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.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.Type: GrantFiled: May 31, 1996Date of Patent: September 2, 1997Assignee: AllerganInventors: Vidyasagar Vuligonda, Roshantha A. Chandraratna
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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: 5618943Abstract: Compounds of the formula ##STR1## 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: Vidyasagar Vuligonda, Alan T. Johnson, Richard L. Beard, Min Teng, Tae K. Song, Harold N. Wong, Roshantha A. Chandraratna
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Patent number: 5607976Abstract: Substituted benzenesulfonylureas and -thioureas, processes for their preparation, their use for the production of pharmaceutical preparations, and pharmaceutical preparations containing them.Substituted benzenesulfonylureas and -thioureas of the formula I ##STR1## exhibit effects on the cardiovascular system.Type: GrantFiled: February 8, 1996Date of Patent: March 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Heinrich Englert, Uwe Gerlach, Peter Crause, Dieter Mania, Heinz G ogelein, Joachim Kaiser
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Patent number: 5514679Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano;Y is alkylene of 3 to 9 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo;R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle;or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.Type: GrantFiled: May 13, 1994Date of Patent: May 7, 1996Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz
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Patent number: 5510538Abstract: A process for the selective oxidation of a primary or secondary alcohol to an aldehyde or ketone and for the oxidation of a 1,2-diol to an .alpha.-ketol or .alpha.-diketone, which comprises contacting the alcohol or 1,2-diol with o-iodoxybenzoic acid. This process is suited for selective oxidation of alcohols containing easily oxidizable groups, such as amino or thioether groups and easily oxidizable heterocycles.Type: GrantFiled: December 16, 1994Date of Patent: April 23, 1996Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Marco Frigerio, Simona Sputore, Marco Santagostino
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Patent number: 5498795Abstract: Compounds of the formula ##STR1## wherein R.sub.1 -R.sub.3 and R.sub.5 independently are hydrogen, lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons, lower alkyl substituted cycloalkyl of 3 to 15 carbons; R.sub.4 is lower alkyl of 1 to 6 carbons, branched chain alkyl or cycloalkyl of 3 to 15 carbons or lower alkyl substituted cycloalkyl of 3 to 15 carbons; X is S or O; Y is a phenyl group, or heteroaryl selected from a group consisting of pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, imidazolyl and oxazolyl, said groups being substituted with the R.sub.5 group defined above; 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.11, CH.sub.2 OCOR.sub.Type: GrantFiled: December 29, 1994Date of Patent: March 12, 1996Assignee: Allergan, Inc.Inventors: Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5484949Abstract: The present invention relates to a method for the synthesis of .alpha., .beta.-unsaturated ketones which comprises, in the method for the synthesis of .alpha., .beta.-unsaturated ketones represented by general formula ##STR1## reacting aldehydes represented by general formulaR.sup.1 CHO(where R.sup.1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula ##STR2## (where M.sup..sym. is an alkali metal ion), in the presence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) ##STR3## a cyclic secondary amine represented by general formula (2) ##STR4## (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R.sup.3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and ##STR5## is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3)CH.sub.3 NHCH.Type: GrantFiled: March 2, 1994Date of Patent: January 16, 1996Assignee: Nippon Soda Co., Ltd.Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
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Patent number: 5463083Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes 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. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes 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, to a patient in need of such therapy.Type: GrantFiled: January 6, 1994Date of Patent: October 31, 1995Assignee: Cytomed, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
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Patent number: 5457237Abstract: Certain dihydroxyindanone compounds, and their pharmaceutically-acceptable salts, are inhibitors of tyrosine kinase enzymes, and so are useful for the control of tyrosine kinase dependent diseases (e.g., cancer, atherosclerosis).Type: GrantFiled: November 23, 1993Date of Patent: October 10, 1995Assignee: Pfizer Inc.Inventor: Robert L. Dow
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Patent number: 5455265Abstract: Process of treatment of mammals, including humans to treat diseases or conditions of the type which are normally treated with retinoid-like compounds is disclosed, with pharmaceutical compositions containing an active compound which is a selective agonist of the RXR retinoid receptor sites in preference to the RAR retinoid receptor sites. A compound is defined to be a selective agonist of the RXR receptor site if the compound is at least approximately ten times more effective as an agonist in the RXR receptor sites than in the RAR receptor sites.Type: GrantFiled: February 11, 1993Date of Patent: October 3, 1995Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5434151Abstract: 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: August 24, 1992Date of Patent: July 18, 1995Assignee: CytoMed, Inc.Inventors: Xiong Cai, Sajjat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5399724Abstract: Novel acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the following general formula (I): ##STR1## [wherein R.sup.1 is a hydrogen atom, 1-alkoxyalkyl group, tetrahydrofuryl group, tetrahydropyranyl group or acyl group; R.sup.2 is a group of formula: --CHO, --CH.sub.2 OR.sup.3 or ##STR2## (wherein R.sup.3 is a hydrogen atom, 1-alkoxyalkyl group, tetrahydrofuryl group, tetrahydropyranyl group or acyl group; and R.sup.4 is C.sub.1 to C.sub.4 alkyl group) with the proviso that R.sup.1 and R.sup.3 do not represent the same substituents simultaneously; when R.sup.1 is a hydrogen atom, R.sup.3 is not acetyl group or tetrahydropyranyl group; and when R.sup.2 is a group of formula: ##STR3## R.sup.1 is not a hydrogen atom).Type: GrantFiled: September 28, 1993Date of Patent: March 21, 1995Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5387594Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## 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: August 4, 1992Date of Patent: February 7, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5358938Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl terahydrothiophenes, 2,4-diaryl tetrahydrofurans, 2,4-diaryl tetrahydrothiphenes, 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: July 13, 1992Date of Patent: October 25, 1994Assignee: CytoMed, Inc.Inventors: Xiong Cai, Saijat Hussoin, San-Bao Hwang, David Killian, T. Y. Shen
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Patent number: 5304661Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: April 9, 1993Date of Patent: April 19, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5288750Type: GrantFiled: January 31, 1991Date of Patent: February 22, 1994Assignee: Orion-yhtyma OyInventors: Pentti Pohto, Paivi A. Aho, Reijo J. Backstrom, Erkki J. Honkanen, Inge-Britt Y. Linden, Erkki A. O. Nissinen
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace
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Patent number: 5274136Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordance with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: July 1, 1992Date of Patent: December 28, 1993Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr.
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Patent number: 5264456Abstract: Retinoid like activity is exhibited by compounds of the formula ##STR1## where R.sub.1 -R.sub.3 independently are hydrogen, lower alkyl, cycloalkyl or lower alkenyl, A and B independently are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, SR.sub.4 or OR.sub.4 where R.sub.4 is lower alkyl, cycloalkyl or lower alkenyl; Y is selected from a group consisting of furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; E is lower alkenyl, lower alkynyl, lower cycloalkyl, lower branched chain alkyl, or is characterized by the formula (CH.sub.2).sub.n where n is 0-5, and Z is H, OH, OR.sub.5, OCOR.sub.5, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH, CH.sub.2 OR.sub.6, CH.sub.2 OCOR.sub.6, or --CHO, CH(OR.sub.7).sub.2, CHOR.sub.8 O, or COR.sub.9, CR.sub.9 (OR.sub.7).sub.2, CR.sub.9 OR.sub.8 O where R.sub.5 is lower alkyl, phenyl or lower alkylphenyl, R.sub.6 is lower alkyl, phenyl or lower alkylphenyl, R.sub.7 is lower alkyl, R.sub.Type: GrantFiled: October 28, 1992Date of Patent: November 23, 1993Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5208353Abstract: This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.Type: GrantFiled: July 15, 1992Date of Patent: May 4, 1993Assignee: SmithKline Beecham Corp.Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
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Patent number: 5196532Abstract: Compounds of formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or methyl, A is an ethylene or methylene radical which is unsubstituted or substituted by methyl, hydroxyl or oxo,L is a saturated or unsaturated five-membered or six-membered heterocyclic structure which is unsubstituted or substituted by hydroxyl, mercapto, C.sub.1 -C.sub.6 -alkyl, or C.sub.1 -C.sub.4 -alkanoyl and has from 1 to 3 heteroatoms from the group consisting of N, O and S, the second and third heteroatoms being a nitrogen atom,R.sup.3 is hydrogen, a hydroxy or C.sub.1 -C.sub.6 -alkoxy group,R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or methoxy,R.sup.5 is hydrogen or methoxy or tert-butyl,R.sup.6 is hydrogen methyl, nitrile or a C.sub.2 -C.sub.10 -ketal group or the radical --CHR.sup.7 OR.sup.8 --CHR.sup.7 --NR.sup.9 R.sup.10, --COR.sup.11, --SR.sup.12, ##STR2## in which R.sup.7 is hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sup.8 is hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.Type: GrantFiled: June 18, 1991Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Bernd Janssen, William V. Murray, Michael P. Wachter, Stanley Bell
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Patent number: 5179123Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxgen, sulfur, --CH.dbd.CH--or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.Type: GrantFiled: November 4, 1991Date of Patent: January 12, 1993Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5169958Abstract: A process for the preparation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.10 -alkoxy or aryloxy,R.sup.2 is aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen andR.sup.3 is tetrahydrofuranyl or aryl which is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl and/or halogen, which comprises reacting 3-amino-2-propen-1-ones of the formula II ##STR2## where R.sup.1 and R.sup.2 have the abovementioned meanings, and R.sup.4 and R.sup.5 are, independently of one another, hydrogen, C.sub.1 -C.sub.10 -alkyl or aryl, with a magnesium halide of the formula IIIR.sup.3 --Mg--Y (III)where Y is halogen, at from -20.degree. to 100.degree. C., and novel .alpha.,.beta.-unsaturated carbonyl compounds and novel 3-amino-2-propen-1-ones are described.Type: GrantFiled: October 1, 1991Date of Patent: December 8, 1992Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Norbert Goetz, Thomas Kuekenhoehner
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Patent number: 5112977Abstract: Substituted naphthacenediones of the formula I ##STR1## in which R.sup.1 to R.sup.8 are H and at least one of R.sup.1 to R.sup.8, for example R.sup.2 and R.sup.3 or R.sup.2 and R.sup.6, are, for example, C.sub.1 -C.sub.20 alkoxy, C.sub.1 -C.sub.20 alkenoxy, C.sub.1 -C.sub.20 -alkylsulfinyl, --CN, --CF.sub.3, --NO.sub.2, --Si(CH.sub.3).sub.3 or --COO(C.sub.1 -C.sub.12 alkyl), are suitable, when incorporated into polymers having hydroxyalkyl groups, for currentless deposition of metals onto the polymer surface. They are in some cases suitable as photoinitiators.Type: GrantFiled: May 24, 1989Date of Patent: May 12, 1992Assignee: Ciba-Geigy CorporationInventors: Walter Fischer, Marcus Baumann, Jurgen Finter, Vratislav Kvita, Carl W. Mayer, Wolfgang Wernet
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Patent number: 5099033Abstract: The present invention is directed to a process of making tetrahydrofuran of the formula (D) ##STR1## resulting in 2,5-diaryltetrahydrofuran PAF antagonists of pharmaceutically acceptable purity.Type: GrantFiled: June 29, 1990Date of Patent: March 24, 1992Assignee: Merck & Co., Inc.Inventors: Ichiro Shinkai, Andrew S. Thompson, Thomas R. Verhoeven
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Patent number: 5034537Abstract: This invention relates to (R)-.alpha.-methyl-4-halobenzenemethanamine salts of epimers of acids of the formula ##STR1## and the use of these salts to separate these epimers. These acids are leukotriene antagonists.Type: GrantFiled: February 8, 1990Date of Patent: July 23, 1991Assignee: SmithKline Beecham CorporationInventor: James S. Frazee
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Patent number: 5013854Abstract: An improved process for preparing trialkylsilyl ester and acid halide derivatives of carboxylic acids is provided along with novel trialkylsilyl ester intermediates of 2-(2-furyl)-2-methoximinoacetic acid.Type: GrantFiled: February 2, 1989Date of Patent: May 7, 1991Assignee: Eli Lilly and CompanyInventor: Charles A. Bunnell
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Patent number: 5012005Abstract: 4-oxaaldehydes of the formula ##STR1## are prepared by catalytic isomerization of 1,3-dioxanes by a process in which a 1,3-dioxane of the formula ##STR2## where R.sup.1, R.sup.2, R.sup.4 and R.sup.5 are identical or different and are each hydrogen, a straight-chain or branched alkyl, alkenyl or alkynyl radical of not more than 18 carbon atoms, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, aralkyl, aralkenyl or alkenylaryl radical of 5 to 16 carbon atoms or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 and/or R.sup.4 and R.sup.5 together with the carbon atoms to which they are bonded may form a cycloalkane, a cycloalkene or a heterocyclic structure, and the stated radicals may furthermore carry substituents which are inert under the reaction conditions, and R.sup.3 is hydrogen or straight-chain or branched alkyl, is isomerized using a metal oxide catalyst, which has been treated with an acid, and/or a silica phase having a zeolite structure.Type: GrantFiled: July 27, 1989Date of Patent: April 30, 1991Inventors: Wolfgang Hoelderich, Franz Merger
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Patent number: 5011847Abstract: The present invention is directed to a specifically substituted tetrahydrofuran of the formula (I) ##STR1## wherein Ar is a pyridyl, dimethoxy-pyridyl or a dimethoxy-pyrazinyl group, R.sup.4 is an alkylthio, alkylsulfinyl or alkylsulfonyl containing group, Y is an alkyl or substituted alkyl group, R.sup.6 is an alkyl or a substituted alkyl and the substituents at positions 3, 4 and 5 are acyclic.Type: GrantFiled: June 8, 1989Date of Patent: April 30, 1991Assignee: Merck & Co., Inc.Inventors: Tesfaye Biftu, Mitree M. Ponpipom, Nirindar N. Girotra
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Patent number: 5010100Abstract: The present invention is directed to a specifically substituted tetrahydrofuran of the formula (I) ##STR1## wherein R.sup.4 is an alkylthio, alkylsulfinyl or alkylsulfonyl containing group, Y is an alkyl or substituted alkyl group and R.sup.6 is an alkoxy or a substituted alkoxy or alkyl group.Type: GrantFiled: June 8, 1989Date of Patent: April 23, 1991Assignee: Merck & Co. Inc.Inventors: Tesfaye Biftu, John C. Chabala, Robert L. Bugianesi, Mitree M. Ponpipom, Soumya P. Sahoo
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Patent number: 4973696Abstract: A stereoselective process is described for preparing optically active alpha,beta-disubstituted carbonyl compounds, comprising forming an acetal between an alpha,beta-unsaturated aldehyde or ketone and tartaric acid or a derivative thereof, halogenating the product thus obtained, and restoring the carbonyl compound.Type: GrantFiled: January 17, 1989Date of Patent: November 27, 1990Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli, Francesco Minisci
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Patent number: 4929751Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.Type: GrantFiled: October 19, 1987Date of Patent: May 29, 1990Assignee: Yale UniversityInventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
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Patent number: 4927947Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## wherein A is pyridyl, furyl, thienyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-5; and B is H, --COOH and its esters, amides and pharmaceutically acceptable salts, --CHO and its acetal derivatives, --COR.sub.1 and its ketal derivatives where R.sub.1 is --(CH.sub.2).sub.n CH.sub.3 where n is defined above, or --CH.sub.2 OH and its ether and acyl ester derivatives; or a pharmaceutically acceptable salt.Type: GrantFiled: January 30, 1989Date of Patent: May 22, 1990Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4920232Abstract: Known and novel substituted acroleins of the general formula I ##STR1## where R.sup.1 is alkoxy, phenoxy, halogen, haloalkyl, haloalkoxy, haloalkylthiyl or nitro, n is an integer from 1 to 5, in the case of n being greater than 1 the R.sup.1 s being identical or different and in the event of nitro substitution the aromatic ring carrying not more than 3 nitro groups, and where R.sup.2 is alkyl, cycloalkyl, unsubstituted or substituted aryl or hetaryl or a nonaromatic heterocyclic radical, are prepared by reacting a phenylacetaldehyde of the general formula II ##STR2## with an aldehyde of the general formula III[R.sup.2 -CHO] IIIin the presence of a base and a solvent. These acroleins are useful to prepare hydroxymethyloxiranes which are intermediates in the synthesis of antimycotic and fungicidal azoylmethyloxiranes.Type: GrantFiled: June 27, 1988Date of Patent: April 24, 1990Assignee: BASF AktiengesellschaftInventors: Norbert Goetz, Stefan Karbach, Hans-Gert Recker
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Patent number: 4897397Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.Type: GrantFiled: December 16, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Neng Y. Shih, David J. Blythin
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Patent number: 4829091Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordane with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: May 27, 1987Date of Patent: May 9, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr
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Patent number: 4810716Abstract: The present invention is novel diarylalkanoids having activity as lipoxygenase inhibitors, novel pharmaceutical compositions therefor, and novel methods of use in treating asthma, allergies, cardiovascular diseases, migraines, psoriasis and immunoinflammatory diseases for diarylalkanoids. The compounds of this invention are also useful as cytoprotective agents.Type: GrantFiled: March 3, 1987Date of Patent: March 7, 1989Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn
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Patent number: 4772714Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##Type: GrantFiled: July 7, 1986Date of Patent: September 20, 1988Assignee: Agency of Industrial Science & TechnologyInventors: Masato Tanaka, Toshiyasu Sakakura
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Patent number: 4709097Abstract: 4-oxa-aldehydes are prepared by catalytic isomerization of a 1,3-dioxane using an acidic zeolite catalyst.Type: GrantFiled: April 14, 1986Date of Patent: November 24, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Rolf Fischer
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Patent number: 4696941Abstract: Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent a straight-chain or branched alkyl group of 1 to 15 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a 2-furyl, 3-furyl, 3-pyridyl, 4-pyridyl or 2-thienyl group or an aromatic group of the formula ##STR2## wherein X, Y and Z are the same or different and represent hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, alkoxy with 1 to 4 carbon atoms, halogen, nitro or hydroxy groups are useful as pharmaceutical, veterinary and cosmetic agents.Type: GrantFiled: June 28, 1985Date of Patent: September 29, 1987Assignee: Groupement d'Interet Economique dit: Centre International 'de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan
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Patent number: 4692513Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.Type: GrantFiled: December 20, 1985Date of Patent: September 8, 1987Assignee: The Procter & Gamble CompanyInventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
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Patent number: 4686291Abstract: A process for the preparation of a methyl ketone of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, optionally substituted aryl or optionally substituted heteroaryl,R.sup.2 is alkyl,R.sup.3 is alkyl orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, from a cycloalkyl ring,comprising reacting a methyl sec.-alkyl ketone of the formula ##STR2## with a halide of the formulaR.sup.1 --CH.sub.2 --Xin whichX is halogen,in the presence of a base, a diluent, and a phase-transfer catalyst.Type: GrantFiled: November 26, 1985Date of Patent: August 11, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hans-Ludwig Elbe
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Patent number: 4681952Abstract: A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C.Type: GrantFiled: November 7, 1984Date of Patent: July 21, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4650885Abstract: A process is provided for preparing a derivative of naphthazarin represented by the general formula (I) of: ##STR1## wherein X.sub.1, X.sub.2 and X.sub.3 each stands for an atom or a group consisting of hydrogen, a hydroxyl group, organic residues and halogens; and R.sub.1 to R.sub.6 each stands for an atom or a group selected from the group consisting of hydrogen and hydrocarbon groups. The derivative of naphthazarin is prepared by the step of reacting, in the presence of an acid catalyst, the following compounds represented by the general formulae (II) and (III): ##STR2## wherein R is an atom or a group selected from the group consisting of hydroxyl, oxyhydrocarbon, siloxy and acyloxy groups and halogen atoms.Type: GrantFiled: April 30, 1986Date of Patent: March 17, 1987Assignee: Nippon Oil Co., Ltd.Inventors: Yoshihiro Kobori, Tetsuya Takezono
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Patent number: 4644009Abstract: Provided are new compounds having valuable therapeutic activity. These compounds are of the formula: ##STR1## and salts thereof, whereinX=O, S or NR.sub.2 ;Z=(CHR.sub.3).sub.n C(R.sub.3))OH)--, ##STR2## --CH.sub.3 .dbd.CH.sub.3 CR.sub.3 (OH)--, or --(CHR.sub.3).sub.n', M=--O--, --S--, or ##STR3## Z.sub.1 is an alkylene chain of 0-5 carbon atoms in the principal chain and a total of 7 carbon atoms;R.sub.1 is H, phenyl, naphthyl or a sulfur, nitrogen or oxygen-heterocyclic ring;R.sub.2 is H, alkyl, aryl or aralkyl;R.sub.3 is H or CH.sub.3 ;n=0-5; andn'=1-5.Type: GrantFiled: October 29, 1984Date of Patent: February 17, 1987Assignee: USV Pharmaceutical CorporationInventors: Fu-chih Huang, Joseph Auerbach