Oxy In Acid Moiety Patents (Class 560/53)
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Patent number: 5373092Abstract: This invention relates to the production of derivatives of hydroxymethoxy mandelic acid (HMMA) and homvanillic acid (HVA), to their use in raising antibodies, and in the production of labelled compounds, and to the use of such materials in immunoassays for HMMA and HVA.Type: GrantFiled: September 15, 1993Date of Patent: December 13, 1994Assignee: Cancer Research Campaign Technology LimitedInventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
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Patent number: 5360924Abstract: Process for preparing aromatic olefins of the formula (1) ##STR1## in which R.sup.1 -R.sup.3 are hydrogen, alkyl (C.sub.1 -C.sub.8) , alkoxy-(C.sub.1 -C.sub.5), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO, --COalkyl(C.sub.1 -C.sub.4) , --COphenyl, --COOalkyl (C.sub.1 -C.sub.4) , --OCOalkyl(C.sub.1 -C.sub.4), --NHCOalkyl(C.sub.1 -C.sub.4) , --CF.sub.3, --NH.sub.2, --NH--alkyl(C.sub.1 -C.sub.4) or --N(alkyl(C.sub.1 -C.sub.4)).sub.2 and R.sup.4 is hydrogen, alkyl(C.sub.1 -C.sub.8), phenyl, fluorine, chlorine, bromine, --OH, --NO.sub.2, --CN, --CHO or --OCOalkyl (C.sub.1 -C.sub.4) , and X is, inter alia, alkenyl(C.sub.2 -C.sub.12) or cycloalkenyl(C.sub.4 -C.sub.8) or the group ##STR2## in which R.sup.5 and R.sup.6 are, independently of one another, hydrogen or methyl, and Y is --phenyl, --CN, --COOH, --COOalkyl(C.sub.1 -C.sub.12), --COOphenyl, ##STR3## --CON (phenyl).sub.2, --COalkyl(C.sub.1 -C.sub.12), --COphenyl, --Oalkyl(C.sub.1 -C.sub.12) , --Ophenyl or the radical ##STR4## in which R.Type: GrantFiled: January 6, 1994Date of Patent: November 1, 1994Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Hartmut Fischer, Heinz Strutz
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Patent number: 5359126Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.Type: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5356919Abstract: 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; and wherein m is 0, 1, 2, or 3.Type: GrantFiled: May 30, 1991Date of Patent: October 18, 1994Assignee: G. D. Searle & Co.Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
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Patent number: 5334748Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2 CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.tbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1 S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: September 9, 1988Date of Patent: August 2, 1994Assignee: Imperial Chemical Industries PLCInventors: Alan J. Buckley, Michael G. Huchings, Ian Ferguson, Kevin Beautement, John M. Clough, Patrick J. Crowley, Christopher R. A. Godfrey, Paul J. deFraine, Vivienne M. Anthony, Stephen P. Heaney
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Patent number: 5326900Abstract: Compounds of the general formula I ##STR1## and drugs and cosmetics prepared therefrom are described.Type: GrantFiled: December 4, 1992Date of Patent: July 5, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Bernd Janssen
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Patent number: 5322794Abstract: Fluorescence probes are described comprising coronene fluorophores chemically attached to lipids or membrane-mimetic molecules via hydrocarbon spacers of defined length. Also described is a method for determining lipid packing and dynamics in membranes, a method for estimating hydrodynamic properties of macromolecules and macromolecular complexes, and a method for measuring changes in Ca.sup.+2 concentrations in or near membranes.Type: GrantFiled: February 16, 1993Date of Patent: June 21, 1994Inventor: Lesley Davenport
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Patent number: 5304672Abstract: A method for the preparation of compounds of the formula ##STR1## wherein X represents a group of the formula OR.sub.1 or NR.sub.1 R.sub.2, wherein R.sub.1 and R.sub.2 independently represent H or an organic group that forms a stable covalent bond with the N or 0 of said X; Y is H or an organic group that forms a stable ester with the adjacent COO group; R is an alkyl or aryl group optionally substituted with one or more stable organic substituents; each R.sub.3 independently represents a stable organic group; and n is an integer from 0 to 3;the method using new intermediates of the formula ##STR2## wherein R.sub.3 and Y have the foregoing meanings;W is either F or Cl; andR.sub.9 is a hydrocarbon such as a C.sub.1 -C.sub.4 alkyl or alkenyl group.Type: GrantFiled: November 9, 1992Date of Patent: April 19, 1994Assignees: Orsan, OrsemInventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
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Patent number: 5288742Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: March 18, 1992Date of Patent: February 22, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, David Waterson
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Patent number: 5283359Abstract: The preparation of arylethanolamines, and in particular albuterol (salbutamol), together with their novel boron, acetal and hemi-acetal intermediates is described.Type: GrantFiled: March 1, 1993Date of Patent: February 1, 1994Assignee: Schering Corp.Inventors: Chou-Hong Tann, T. K. Thiruvengadam, John Chiu, Michael Green, Timothy L. McAllister, Cesar Colon, Junning Lee
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Patent number: 5278333Abstract: A process for the .alpha.-monoalkylation of arylacetonitriles, arylacetoesters and arylacetic acids with dialkyl carbonates in liquid phase, in the presence of bases at temperatures ranging from about 100.degree. C. to about 270.degree. C.Type: GrantFiled: July 30, 1992Date of Patent: January 11, 1994Assignee: Tessenderlo Chemie N.V.Inventors: Pierre C. Loosen, Pietro Tundo, Maurizio Selva
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Patent number: 5266720Type: GrantFiled: July 8, 1991Date of Patent: November 30, 1993Assignee: Cancer Research Campaign Technology LimitedInventors: Gerard Gallacher, Geoffrey W. Mellor, Yee-Ping Ho
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Patent number: 5264611Abstract: A process for preparing a trans-.beta.-aroylacrylic ester which comprises reacting an aryl methyl ketone and an alkyl acetal of alkyl glyoxylate in the presence of an acid catalyst with heating.This process is excellent in operability, safety and ecomony and therefore is industrially advantageous process.Type: GrantFiled: January 6, 1992Date of Patent: November 23, 1993Assignee: Kanegafuchi Kagaku Kabushiki KaishaInventors: Yoshifumi Yanagida, Shingo Matsumoto, Satomi Takahashi
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Patent number: 5262559Abstract: A process for producing a 1,4-dihydro-4-oxo-quinoline-3-carboxylic acid by reacting an acctophenone with a dialkoxycarbonate to obtain the corresponding .beta.-ketoester, treating the .beta.-ketoester with a trialkylorthoformate in the presence of an acid anhydride followed by treatment with a substituted or unsubstituted amine to obtain the corresponding enaminoketoester, and then reacting the enaminoketoester with a strong base to obtain the corresponding quinoline-3-carboxylic acid ester. The acid ester may then be hydrolyzed, if desired, to obtain the quinoline-3-carboxylic acid. Also disclosed herein are compounds useful as intermediates useful in the production of quinoline-3-carboxylic acid.Type: GrantFiled: January 17, 1991Date of Patent: November 16, 1993Assignee: Abbott LaboratoriesInventor: Daniel T. Chu
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Patent number: 5262565Abstract: Compounds of the formula: ##STR1## where R.sup.1 is a hydrogen atom or a lower alkyl group;R.sub.2 is a lower alkoxy group;R.sub.3 is a hydroxyl or lower alkoxy group;Z is represented by the formula: ##STR2## where R.sub.2 and R.sub.3 may be the same or different from each other and each stands for a hydrogen atom or a lower alkyl;Y is represented by the formula: --(CH.sub.2).sub.n -- where n is 0 or an integer of 1 to 2 or a group represented by the formula: ##STR3## where R.sup.2 and R.sup.3 may be the same or different from each other and each stands for a lower alkyl group; andR.sup.4 represents a group of the formula: ##STR4## where p is 0 or an integer of 1 to 3 and R.sup.12 is hydrogen, a halogen atom, a lower alkyl or a lower alkoxy group a hydrogen atom, R.sup.2 is a methoxy group, R.sup.3 is a hydroxy group and R.sup.4 is a benzyl group having anti-inflammatory activity.Type: GrantFiled: November 12, 1991Date of Patent: November 16, 1993Assignee: Eisai Co., Ltd.Inventors: Hiroyuki Yoshimura, Shinya Abe, Tetsuya Kawahara, Takashi Inoue, Hiroshi Shirota, Kenichi Chiba, Kenichi Kusube, Toru Horie, Takeshi Suzuki, Isao Yamatsu, Naoyuki Shimomura, Kazuo Okano, Richard S. J. Clark, Takashi Mori, Shuhei Miyazawa, Ryoichi Hashida, Kenzo Muramoto, Koukichi Harada
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Patent number: 5256694Abstract: Novel diarylacetylenes of the formula I ##STR1## where A, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the meanings stated in the description, are useful for the treatment of disorders.Type: GrantFiled: May 22, 1992Date of Patent: October 26, 1993Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Fritz-Frieder Frickel, Axel Nuerrenbach
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Patent number: 5254708Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: October 19, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5252707Abstract: There are disclosed a novel inositol-1,4,5-triphosphoric acid derivative, inositol-1,3,4-triphosphoric acid derivative, inositol-1,3,4,5-tetraphosphoric acid derivative, and a bonded substance of the same and a protein. They control the metabolic process of an organism concerned with calcium ions to thereby exert a medicinal virtue.Type: GrantFiled: May 15, 1991Date of Patent: October 12, 1993Assignee: Mitsui Toatsu Chemicals IncorporatedInventors: Shoichiro Ozaki, Yutaka Watanabe, Masato Hirata, Akira Awaya
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Patent number: 5237091Abstract: The present invention relates to a naphthalene derivative. More particularly, it relates to a naphthalene derivative exhibiting an excellent activity as a drug.Type: GrantFiled: May 29, 1992Date of Patent: August 17, 1993Assignee: Eisai Co., Ltd.Inventors: Hiroyuki Yoshimura, Shinya Abe, Tetsuya Kawahara, Naoyuki Shimomura, Kazuo Okano, Richard S. J. Clark, Takashi Mori, Shuhei Miyazawa, Ryoichi Hashida, Kenzo Muramoto, Koukichi Harada, Takashi Inoue, Hiroshi Shirota, Kenichi Chiba, Kenichi Kusube, Toru Horie, Takeshi Suzuki, Isao Yamatsu
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Patent number: 5227512Abstract: An optically active stilbene compound of formula (I): ##STR1## wherein R is an alkoxy group with 20 or less carbon atoms; n is an integer of 1 or 2; and R* is an optically active group, a substituted benzylphosphonate compound of formula (II) serving as an intermediate for preparing the above active stilbene compound, ##STR2## wherein X represents ##STR3## R' is an alkyl group having 1 to 5 carbon atoms, or an unsubstituted or substituted aryl group; and R* is the same as in formula (I), a method of producing the optically active stilbene compound of formula (I), and a liquid crystal composition containing the optically active stilbene compound of formula (I) are disclosed.Type: GrantFiled: December 20, 1990Date of Patent: July 13, 1993Assignee: Ricoh Company, Ltd.Inventor: Masayuki Shoshi
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Patent number: 5227505Abstract: The present invention relates to substituted cyclopentanone and cyclohexanone derivatives and substituted cyclopentenone and cyclohexenone derivatives, which are useful as intermediates for pharmaceutical products and agricultural chemicals and especially useful for the synthesis of prostaglandins, and also to a process for producing the same.Type: GrantFiled: December 14, 1990Date of Patent: July 13, 1993Assignee: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Kazutaka Arai, Katsuaki Miyaji
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Patent number: 5221762Abstract: E-oxime ethers of phenylglyoxylic esters of the formula I ##STR1## where X and Y are each halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or trifluoromethyl;m is an integer from 0 to 4;n is an integer from 0 to 3;are prepared.Type: GrantFiled: December 13, 1991Date of Patent: June 22, 1993Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Bernd Wolf, Remy Benoit, Hubert Sauter, Michael Hepp, Wassilios Grammenos, Thomas Kuekenhoehner
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Patent number: 5210315Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.Type: GrantFiled: October 18, 1991Date of Patent: May 11, 1993Assignee: Takasago International CorporationInventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
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Patent number: 5206389Abstract: These acrylates are those of formulae: ##STR1## where R=C.sub.1 -C.sub.12 alkyl, C.sub.5 -C.sub.12 cycloalkyl, aryl, arylalkyl or alkylaryl; Y=C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.12 aryl, heterocyclic radical whose ring contains from 5 to 10 members and whose heteroatom is chosen from N, O and S, an alkylaryl in which the alkyl part contains from 1 to 4 carbon atoms, Y not being able to denote 1,4-phenylene when R denotes methyl; and Z=hydrocarbon radical containing at least 2 C forming with O and the 2 adjacent Cs a ring containing from 4 to 8 members.To prepare them, an acrylate of formula CH.sub.2 .dbd.CH--COOR is reacted with a dialdehyde OHC--Y--CHO in the presence of an effective quantity of at least one functionalisation catalyst.The invention also relates to the preparation of new polymers and copolymers from the said acrylates.Type: GrantFiled: June 27, 1991Date of Patent: April 27, 1993Assignee: AtochemInventors: Marie-Christine Berthe, Paul Caubere, Yves Fort
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Patent number: 5200535Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: April 6, 1993Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5194664Abstract: Compounds of the general formula I ##STR1##Type: GrantFiled: November 12, 1991Date of Patent: March 16, 1993Assignee: BASF AktiengesellschaftInventors: Hans-Heiner Wuest, Bernd Janssen
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Patent number: 5194663Abstract: An aromatic derivative of butyric acid has the formula ##STR1## These aromatic derivatives of butyric acid are useful in human and veterinary medicines as well as in cosmetic compositions.Type: GrantFiled: August 9, 1991Date of Patent: March 16, 1993Assignee: Societe Anonyme Dite: L'OrealInventors: Jean Maignan, Gerard Malle, Gerard Lang
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Patent number: 5183891Abstract: A method for the preparation of compounds of the formula ##STR1## wherein X represents a group of the formula OR.sub.1 or NR.sub.1 R.sub.2, wherein R.sub.1 and R.sub.2 independently represent H or an organic group that forms a stable covalent bond with the N or O of said X; Y is H or an organic group that forms a stable ester with the adjacent COO group; R is an alkyl or aryl group optionally substituted with one or more stable organic substituents; each R.sub.3 independently represents a stable organic group; and n is an integer from 0 to 3;the method using new intermediates of the formula ##STR2## wherein R.sub.3 and Y have the foregoing meanings; W is either F or Cl;and R.sub.9 is a hydrocarbon such as a C.sub.1 -C.sub.4 alkyl or alkenyl group.Type: GrantFiled: November 9, 1989Date of Patent: February 2, 1993Assignees: Orsan, OrsemInventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
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Patent number: 5182401Abstract: A process for the preparation of a 3-amino-2-(het)aroyl-acrylic acid derivative fo the formula ##STR1## in which Y represents a nitrile, or an ester group, --COOR.sub.1, or an acetyl group, whereR.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, andR denotes optionally substituted alkyl, cyclopropyl, alkoxy, phenyl or amino,A represents nitrogen or C--R.sub.2, whereR.sub.2 denotes hydrogen, methyl, halogen, nitro, methoxy or cyano,X.sub.1 and X.sub.2 are identical or different and denote halogen, andX.sub.3 denotes hydrogen, halogen or nitro andX.sub.4 denotes halogen, nitro, methoxy or methylthio, which comprises reacting a 3-dialkylamino-2-(het)aroyl-acrylic acid derivative of the formula ##STR2## in which R.sub.3 and R.sub.4 are the same or different and represent an alkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which they are bonded, form a ring,with a primary amine of the formula R--NH.sub.2 in the presence of at least one equivalent of an acid HX in a solvent or in excess acid.Type: GrantFiled: May 2, 1991Date of Patent: January 26, 1993Assignee: Bayer AktiengesellschaftInventor: Klaus Grohe
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Patent number: 5177222Abstract: 1,1-Dialkoxy-2-oxo-6-aryl-3,5-alkadienes of the general formula I ##STR1## where Ar is a phenyl, biphenyl or naphthyl radical which may be substituted by one, two or three C.sub.1 -C.sub.4 -alkyl groups, C.sub.1 -C.sub.4 -alkoxy groups, hydroxyl groups, phenoxy groups, amino groups which may be mono- or di-C.sub.1 -C.sub.4 -alkyl-substituted, halogen atoms or a methylenedioxy group, the substituents being identical or different,R.sup.1 is hydrogen or C.sub.1 -C.sub.8 -alkyl,R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.10 -alkoxycarbonyl or C.sub.1 -C.sub.10 -acyl,the radicals R.sup.3 are C.sub.1 -C.sub.8 -alkyl groups which may be bonded to one another with formation of a five-membered or six-membered ring andR.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, are used as sunscreen agents in cosmetic preparations.Type: GrantFiled: November 5, 1990Date of Patent: January 5, 1993Assignee: BASF AktiengesellschaftInventors: Helmut Guembel, Joachim Paust, Karin Sperling-Vietmeier, Rainer Becker
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Patent number: 5177259Abstract: 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: August 27, 1991Date of Patent: January 5, 1993Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn
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Patent number: 5171882Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, intermediates for preparing the derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.Type: GrantFiled: October 16, 1990Date of Patent: December 15, 1992Assignee: Eli Lilly and CompanyInventor: D. Mark Gapinski
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Patent number: 5166167Abstract: A compound of the formula ##STR1## wherein Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, methylenedioxy, phenoxy, phenyl, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, chlorine, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are individually alkyl of 1 to 6 carbon atoms and the exocyclic double bond has (Z) or (E) configuration having fungicidal activity.Type: GrantFiled: March 16, 1992Date of Patent: November 24, 1992Assignee: Roussel UclafInventors: Jean-Louis Brayer, Jean-Pierre Demoute, Gilles Mourioux
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Patent number: 5164527Abstract: Acylation or sulphonylation of aromatic compounds, one of which is selected from aromatic carboxylic and sulphonic acids and esters and anhydrides thereof, using an aluminosilicate catalyst having acidic sites.Type: GrantFiled: April 3, 1991Date of Patent: November 17, 1992Assignee: Imperial Chemical Industries PLCInventor: Alan B. Newton
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Patent number: 5164412Abstract: A Derivative of 5-hetero-6-oxo-PGE A derivative of 5-hetero-6-oxo-PGE of the formula: ##STR1## wherein R.sup.1 is (1) a group of the formula: COOR11(2) hydroxymethylcarbonyl,(3) hydroxymethyl or(4) a group of the formula:CO--AAwherein AA is an amino acid-residue,Z is oxygen, sulfur or a group of the formula: NR21 wherein R21 is hydrogen or alkyl of C1--4;R2 is a single-bond or alkylene of C1--4;R3 isi) alkyl of C1-7,ii) cycloalkyl of C4-7 or cycloalkyl of C4-7 substituted by alkyl of C1-7,iii) phenyl, phenoxy, phenyl or phenoxy substituted by one group selected from alkyl of C1-4, halogen and trihalomethyl, is single-bond or a double bond.Possess PG-like activity, especially cytoprotection, and therefore are useful for treatment for and/or prevention of cytodamage.Type: GrantFiled: April 8, 1991Date of Patent: November 17, 1992Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Yoshitaka Konishi, Masanori Kawamura
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Patent number: 5162571Abstract: Novel phenol derivatives of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, Y and n are as defined in the specification, which have therapeutic and prophylactic activities against cerebral, cardiac, renal and pulmonary circulatory system diseases, respiratory diseases, allergy, anaphylactic shock, endotoxin shock, inflammation and the like as well as inhibiting activities against vascularization by oncocytes.Type: GrantFiled: June 8, 1988Date of Patent: November 10, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsuru Shiraishi, Kohei Mishikawa
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Patent number: 5157048Abstract: An improved method for the decarbalkoxyation 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: November 12, 1991Date of Patent: October 20, 1992Assignee: 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: 5155244Abstract: A method of solubilizing a first compound in a second medium where the first compound has a limited solubility in the second medium. In particular, the method comprises reacting the first compound with the second medium. By this reaction, a product is formed whereby an active component of the first compound is covalently incorporated into the second medium.The first compound and second medium each contain at least one reactive group which will react with a reactive group of the other. In addition, the first compound comprises at least one antioxidant which will be covalently bonded to and thus effectively solubilized in the second medium by the reaction.The second medium comprises glyceride derivatives, silicones, fluorocarbons and alkoxylates containing reactive groups such as hydroxy, amino, carboxyl, ester, or amides.Type: GrantFiled: February 28, 1990Date of Patent: October 13, 1992Assignee: Karlshamns ABInventors: George H. Greene, James C. Phillips, Jerry F. Stults, Jan P. E. Tellings
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Patent number: 5152826Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5149859Abstract: A naphthalene derivative having the formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group or a non-toxic salt moiety; R.sup.2 and R.sup.3 independently represent a hydrogen atom or --OR.sup.4 where R.sup.4 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group;A represents a group: ##STR2## [where X.sup.1 and X.sup.2 represents an oxygen atom or N--OR.sup.5 (where R.sup.5 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group)], a group: ##STR3## [where Y.sup.1 and Y.sup.2 independently an oxygen atom or a group N--OR.sup.6 (where R.sup.6 represents a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group)], or a group: ##STR4## (where n is 0 or 1); and B represents --(CH.sub.2).sub.m --wherein m is an integer of 1, to 8,--(CH.sub.2).sub.m.sbsb.1 --O--(CH.sub.2).sub.m.sbsb.2 --wherein m.sub.1 and m.sub.2 are independently 1 or 2, or ##STR5## wherein m.sub.3 is 0 or 1.Type: GrantFiled: September 14, 1990Date of Patent: September 22, 1992Assignee: Teijin LimitedInventors: Atsuo Hazato, Takumi Takeyasu, Koji Tomimori, Yoshinori Kato
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Patent number: 5145874Abstract: Provided are cyclic hydrocarbons of Formula I ##STR1## with an aminoalkyl sidechain that are useful for treating phospholipase A2 mediated conditions, diabetes, and obesity.Type: GrantFiled: February 25, 1991Date of Patent: September 8, 1992Assignee: The Upjohn CompanyInventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
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Patent number: 5142091Abstract: The present invention provides an .alpha., .beta.-unsaturated ketone and ketoxime derivative represented by the formula ##STR1## wherein Y is oxygen atom or hydroxyimino group, Z is cyano or alkoxycarbonyl group, R.sup.1 and R.sup.2 are the same or different and are each hydrogen atom or lower alkoxyl group.The .alpha., .beta.-unsaturated ketones and ketoxime derivatives of the invention are useful as an intermediate for preparing a (3,4-diarylisoxazol-5-yl)acetic acid derivatives which is useful as an anti-inflammatory agent, analgesic and antipyretic.Type: GrantFiled: July 10, 1991Date of Patent: August 25, 1992Assignee: Taiho Pharmaceutical Company LimitedInventors: Motoaki Tanaka, Yu-ichi Hagiwara, Makoto Kajitani, Mitsugi Yasumoto
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Patent number: 5142095Abstract: 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: August 17, 1989Date of Patent: August 25, 1992Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn
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Patent number: 5137036Abstract: This invention provides smoking compositions which contain a novel di-vanillyl ester flavorant-release additive.Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as di-ethylvanillyl oxalate pyrolyzes and releases ethylvanillin as a volatile flavorant component of the cigarette smoke.Type: GrantFiled: August 10, 1990Date of Patent: August 11, 1992Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventor: Everett W. Southwick
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Patent number: 5135940Abstract: Compounds of the Formulae: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.Type: GrantFiled: March 20, 1991Date of Patent: August 4, 1992Assignee: Merck Frosst Canada, Inc.Inventors: Patrice C. Belanger, Joshua Rokach, Rejean Fortin, Christiane Yoakim, Yvan Guindon
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Patent number: 5136081Abstract: The invention provides a process for the preparation of fungicidally active cyclopentene derivatives of the general formula ##STR1## cyclopentane derivatives of the general formula ##STR2## and cyclohexane derivatives of the general formula ##STR3## in which n, R, R.sup.1, R.sup.2, R.sup.5, X and Y are as herein defined. Compounds of formula II and III are also provided which are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: September 11, 1989Date of Patent: August 4, 1992Assignee: Shell Internationale Research Maatschappij B.V.Inventor: Paul H. Briner
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5128479Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5120862Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the and present invention ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 ll and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present ivnention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.Type: GrantFiled: October 4, 1991Date of Patent: June 9, 1992Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 5117042Abstract: A method of treatment for improving encephalic function which comprises administering, to a subject in need of such treatment, a 15-keto-prostaglandin compound in an amount effective for improvement of encephalic function.Type: GrantFiled: November 21, 1990Date of Patent: May 26, 1992Assignee: K.K. Ueno Seiyaku Oyo KenkyujoInventors: Ryuji Ueno, Hiroyoshi Osama, Tomio Oda