Aldehyde Or Ketone Group In Acid Moiety Patents (Class 560/51)
  • Patent number: 5304672
    Abstract: 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: Grant
    Filed: November 9, 1992
    Date of Patent: April 19, 1994
    Assignees: Orsan, Orsem
    Inventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
  • Patent number: 5292946
    Abstract: The present invention is directed to in-situ preparation of diisopinocamphenylchloroborane, and the use of same in the reduction of prochiral ketones to optically active alcohols such as those of formula B. ##STR1## The compound of Formula B is useful in the production 2,5-diaryltetrahydrofurans useful as PAF antagonists.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: March 8, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Pamela M. Simpson, David M. Tschaen, Thomas R. Verhoeven
  • Patent number: 5278338
    Abstract: 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: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5276154
    Abstract: The present invention provides optically active esters of 7-substituted 3,5-difunctionalized 6-heptenoic acids represented by the following formula: ##STR1## wherein R is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group or a substituted vinyl group;Ar is a condensed aromatic group;X.sup.1 and Y.sup.1 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.1 and Y.sup.1 are attached; andX.sup.2 and Y.sup.2 are not the same and each is a hydrogen atom or a hydroxyl group, or may be combined to represent an oxygen atom which forms a carbonyl group together with the carbon atom to which X.sup.2 and Y.sup.2 are attached,or enantiomers thereof.The present invention further provides processes for preparing the above optically active esters and 7-substituted (3R, 5S, 6E)-3,5-dihydroxy-6-hepten-1,5-olides.
    Type: Grant
    Filed: August 21, 1991
    Date of Patent: January 4, 1994
    Assignee: Sagami Chemical Research Center
    Inventors: Tamejiro Hiyama, Tatsuya Minami, Takeshi Hanamoto, Guntoori B. Reddy
  • Patent number: 5264611
    Abstract: 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: Grant
    Filed: January 6, 1992
    Date of Patent: November 23, 1993
    Assignee: Kanegafuchi Kagaku Kabushiki Kaisha
    Inventors: Yoshifumi Yanagida, Shingo Matsumoto, Satomi Takahashi
  • Patent number: 5262559
    Abstract: 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: Grant
    Filed: January 17, 1991
    Date of Patent: November 16, 1993
    Assignee: Abbott Laboratories
    Inventor: Daniel T. Chu
  • Patent number: 5258404
    Abstract: Disclosed is a 3-(unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivative as represented by the general formula (I): ##STR1## where R.sup.1 and R.sup.2 are each a lower alkyl group;X is a halogen atom, a cyano group, an alkyl group, a haloalkyl group, a phenyl group or a nitro group; andm is 0 or an integer from 1 to 5 and when m is greater than 1 each X can be the same or different.Further, disclosed is a method for the preparation of the compound (I) by carrying out the benzylation, rearrangement, and alkylation from the 2-oxocyclopentane carboxylic acid alkyl ester derivative without isolation of any intermediate compound. In addition, a fungicide is provided in which the 3-(unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivatives (I) is contained as an active ingredient.
    Type: Grant
    Filed: September 16, 1992
    Date of Patent: November 2, 1993
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Isao Ichinose, Masanori Minoguchi, Satoru Kumazawa, Eyji Yoshida
  • Patent number: 5247122
    Abstract: Disclosed are certain novel 2,2'-bisacetoacetates useful as crosslinking agents and a process for the preparation therefor. Also provided are novel enamel compositions containing the crosslinkers and coatings and articles coated with thermosetting coating compositions crosslinked with these novel crosslinkers.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: September 21, 1993
    Assignee: Eastman Kodak Company
    Inventors: J. Stewart Witzeman, Allen L. Crain, Robert J. Clemens
  • Patent number: 5243064
    Abstract: The present invention relates to novel chromophore-containing compounds useful as sunscreen agents which have the ability to absorb both UVA and UVB wavelength radiation. These compounds comprise a specific type of UVA-absorbing chromophore covalently bonded to a specific type of UVB-absorbing chromophore. The chromophore moieties are covalently bonded together such that the electron systems of these moieties are directly coupled to thereby form a new chromophore.The present invention further relates to sunscreen compositions containing the hereinbefore described type of sunscreen agents. Furthermore, the present invention relates to methods for protecting the skin of humans or lower animals from the effects of UVA and UVB wavelength radiation. This method comprises topically applying to the skin an effective coating of a sunscreen composition of the present invention.
    Type: Grant
    Filed: July 31, 1992
    Date of Patent: September 7, 1993
    Assignee: The Procter & Gamble Company
    Inventor: Anthony D. Sabatelli
  • Patent number: 5238602
    Abstract: Compounds of the formula ##STR1## wherein n stands for the number 0 or 1; the rings A.sup.1, A.sup.2 and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; X.sup.1 represents a single covalent bond, --COO--, --OOC--, --CH.sub.2 CH.sub.2 --, p--C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p-- C.sub.6 H.sub.4 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 -- or, insofar as the rings A.sup.1 and A.sup.2 represent 1,4-phenylene, also --NON--; R.sup.2 represents 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or alkenyloxy, with the proviso that the oxygen atom in alkenyloxy is linked with a saturated carbon atom; and R.sup.1 signifies 1E-alkenyl, 2Z-alkenyl, 3E-alkenyl, 4-alkenyl or, insofar as R.sup.2 represents alkenyloxy, also alkyl, their manufacture, as well as liquid crystalline mixtures and the use for electro-optical purposes.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: August 24, 1993
    Assignee: Hoffmann La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt
  • Patent number: 5231113
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where the R groups are independently hydrogen, or lower alkyl; A is --C(O)O--, --OC(O)--, --C(O)S--, or --SC(O)--; n is 0-5; and Z is H, --COB where B is --OH or a pharmaceutically acceptable salt, or B is --OR.sub.1 where R.sub.1 is an ester-forming group, or B is --N(R).sub.2 where R is hydrogen or lower alkyl, or Z is --OE where E is hydrogen or an ether-forming group or --COR.sub.2 where R.sub.2 is hydrogen, lower alkyl, phenyl or lower alkyl phenyl, or Z is --CHO or an acetal derivative thereof, or Z is --COR.sub.3 where R.sub.3 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4 and the sum of n and m does not exceed 4.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: July 27, 1993
    Assignee: Allergan, Inc.
    Inventors: Roshantha A. S. Chandraratna, Robert J. Weinkam
  • Patent number: 5229375
    Abstract: Phosphine oxide-terminated allene-ene-yne compounds are disclosed that possess DNA-cleaving, antimicobial and tumor growth-inhibiting properties. Methods of making and using those compounds are also disclosed.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: July 20, 1993
    Assignee: Scripps Clinic and Research Foundation
    Inventors: Peter E. Maligres, Kyriacos C. Nicolaou
  • Patent number: 5225436
    Abstract: Certain aryl substituted naphthalene, benzoxepine, benzazepine and henzocycloheptene derivatives are disclosed. The compounds are useful in treating hyperproliferative skin disease, allergic reactions and inflammation.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: July 6, 1993
    Assignee: Schering Corporation
    Inventors: Neng-Yang Shih, Pietro Mangiaracina, Michael J. Green, Ashit K. Ganguly
  • Patent number: 5221765
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; 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.2 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 75.degree. C. to about 200.degree. C.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 22, 1993
    Assignee: Ethyl Corporation
    Inventors: Deepak R. Patil, Azfar A. Choudhury, Abbas Kadkhodayan
  • Patent number: 5221762
    Abstract: 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: Grant
    Filed: December 13, 1991
    Date of Patent: June 22, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Bernd Wolf, Remy Benoit, Hubert Sauter, Michael Hepp, Wassilios Grammenos, Thomas Kuekenhoehner
  • Patent number: 5210272
    Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: May 11, 1993
    Assignee: Prototek, Inc.
    Inventor: James T. Palmer
  • Patent number: 5202458
    Abstract: Compounds of the formula I or II ##STR1## in which R, R.sup.0, R.sup.1 and R.sup.2 are as defined in claim 1. The compounds, some of which are novel, are light stabilizers for color photographic recording materials.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: April 13, 1993
    Assignee: Ciba-Geigy AG
    Inventor: David G. Leppard
  • Patent number: 5194663
    Abstract: 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: Grant
    Filed: August 9, 1991
    Date of Patent: March 16, 1993
    Assignee: Societe Anonyme Dite: L'Oreal
    Inventors: Jean Maignan, Gerard Malle, Gerard Lang
  • Patent number: 5194671
    Abstract: The invention relates to a process for the preparation of .beta.-ketocarboxylic acid esters of the general formula ##STR1## in which R.sup.1 is an alkyl radical having 1 to 4 C atoms, R.sup.2 is an alkyl radical or alkenyl radical having 2 to 15 C atoms or a phenyl radical and R.sup.3 is hydrogen or an alkyl or alkenyl radical having 1 to 6 C atoms, characterized in that acetocarboxylic acid esters of the general formula ##STR2## in which R.sup.1 and R.sup.3 are as defined, are reacted with calcium hydroxide or calcium oxide in the presence of an organic solvent and in the absence of water, the calcium chelate complexes formed are acylated with carboxylic acid chloride and the products are then cleaved with aqueous ammonium salt solution to form the .beta.-ketocarboxylic acid esters of formula (I).The .beta.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: March 16, 1993
    Assignee: Wacker-Chemie GmbH
    Inventor: Josef Meier
  • Patent number: 5183891
    Abstract: 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: Grant
    Filed: November 9, 1989
    Date of Patent: February 2, 1993
    Assignees: Orsan, Orsem
    Inventors: Jeffrey Labovitz, William J. Guilford, Lawrence Fang, Yi Liang
  • Patent number: 5182401
    Abstract: 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: Grant
    Filed: May 2, 1991
    Date of Patent: January 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 5179092
    Abstract: A compound having the formula (I): ##STR1## wherein A is --CH.sub.2 --, --O--, or --S--; R.sup.1 is CH.sub.3 or OCH.sub.3 ; R.sup.2 is hydroxy or carboxy which may be optionally esterized or amidated; R.sup.3 is H or a lower alkyl; and n is 0 or an integer of 1 to 6 or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: January 12, 1993
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Fumio Satoh, Seiji Miyano, Kunihiro Sumoto
  • Patent number: 5179229
    Abstract: A process for the preparation of 2,2-diorgano-3-arylpropionic acids is disclosed by the carbonylation of corresponding 2,2-diorgano-1-aryl ethanol in the presence of a Lewis acid catalyst. Furthermore, a process for the production of 2,2-diorgano-3-arylpropionic esters is disclosed by reacting a corresponding 2,2-diorgano-1-aryl ethanol with carbon monoxide and an alcohol in the presence of a Lewis acid catalyst.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: January 12, 1993
    Assignee: Hoechst Celanese Corporation
    Inventor: Varadaraj Elango
  • Patent number: 5177204
    Abstract: This relates to substances represented by formula (I), wherein X stands for represented by either OR in which R is an alkyl of 1 to 4 carbon atoms, or NHR in which is an alkyl of 1 to 4 carbon atoms, or a (CH.sub.2).sub.n NR.sub.2 group wherein n is 2 or 3 while R.sup. is an methyl or an ethyl group; eventually X may represent morpholinyl. Also considered are salts of 4-(2,4-difluorbiphenylyl)-2-methyl-4-oxobutanoic acid with appropriate inorganic or organic bases represented by formula (II) wherein B.sup.+ is either an alkaline metal cation, alkaline earth metal cation, cyclohexylamine cation, or lysine cation. Said substances are characterized by antiinflamatory properties comparable to (and greater than) the initial acid while simultaneously said modifications of their physico-chemical properties broaden the posibilities of their therapeutic application.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: January 5, 1993
    Assignee: Vyzkumng, USTAV pro farmacii a biochemii, Statni podnik
    Inventors: Miroslav Kuchar, Marie Poppova, Jaroslava Grimova, Eva Maturova
  • Patent number: 5169975
    Abstract: Binary azulenesquaric acid dyes of the formula ##STR1## where X is a bridging member, Y is hydrogen, cyano or formula CO--OR.sup.5, CO--NHR.sup.5, OR.sup.5, O--CO--OR.sup.5, NH--CO--R.sup.5, NH--CO--OR.sup.5 or NH--SO.sub.2 --R.sup.5, where R.sup.5 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.5 -C.sub.7 -cycloalkyl or unsubstituted or substituted phenyl, L.sup.1 and L.sup.2 are each, independently of one another, a chemical bond or unsubstituted or substituted C.sub.1 -C.sub.12 -alkylene and R.sup.1, R.sup.2, R.sup.3, R.sup.4, Q.sup.1, Q.sup.2, Q.sup.3 and Q.sup.4 are each, independently of one another, hydrogen or unsubstituted or substituted C.sub.1 -C.sub.12 -alkyl, their intermediates and an optical recording medium containing the novel dyes are described.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: December 8, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Schmitt, Bernhard Albert, Sibylle Brosius, Klaus D. Schomann, Harald Kuppelmaier
  • Patent number: 5164388
    Abstract: A renin inhibiting compound of the formula ##STR1## wherein X is N, O or CH; R.sub.1 is absent or a functional group; A and L are independently selected from absent, C.dbd.O, SO.sub.2 and CH.sub.2 ; D is C.dbd.O, SO.sub.2 or CH.sub.2 ; Y is N or CH; R.sub.2 is hydrogen, loweralkyl or substituted alkyl; Z is a functional group; R.sub.3 is loweralkyl or substituted alkyl; n is 0 or 1; and T is a mimic of the Leu-Val cleavage site of angiotensinogen; or a pharmaceutically acceptable salt, ester or prodrug thereof.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: November 17, 1992
    Assignee: Abbott Laboratories
    Inventors: Biswanath De, Thomas N. Zydowsky, William R. Baker, Joseph F. Dellaria, Saul H. Rosenberg, Hwan S. Jae
  • Patent number: 5146001
    Abstract: In the preparation of benzyl ketones of the formula ##STR1## a benzyl chloride of the formula ##STR2## is reacted with an acid chloride of the formulaR.sup.6 --CO--Cl (III)a) in a first stage with an excess of zinc powder in the presence of a diluent at a temperature between 80.degree. C. and 200.degree. C. under an inert gas atmosphere, and separating off the excess zinc powder, thereby to obtain a benzyl derivative of the formula ##STR3## and b) in a second stage reacting the benzyl derivative of the formual (IV) with an acid chloride of the formula (III) in the presence of a palladium catalyst and in the presence of a diluent at a temperature between 0.degree. C. and 150.degree. C. under an inert gas atmosphere.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: September 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Himmler, Udo Kraatz, Wolfgang Kramer, Klaus Stroech
  • Patent number: 5145874
    Abstract: 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: Grant
    Filed: February 25, 1991
    Date of Patent: September 8, 1992
    Assignee: The Upjohn Company
    Inventors: Roy A. Johnson, Gordon L. Bundy, Gilbert A. Youngdale, Douglas R. Morton, Donald P. Wallach, deceased, by Vera M. Wallach, legal representative
  • Patent number: 5144057
    Abstract: 3-Oxocarboxylic acid esters are produced by acylation of the magnesium enolates of acetoacetic acid esters with carboxylic acid chlorides and cleavage of the acetyl group from the acylacetoacetic acid esters formed as the intermediate product. The yields and purity of the products are considerably improved by adding a tertiary amine during the acylation.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: September 1, 1992
    Assignee: Lonza Ltd.
    Inventor: Martin Eyer
  • Patent number: 5142091
    Abstract: 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: Grant
    Filed: July 10, 1991
    Date of Patent: August 25, 1992
    Assignee: Taiho Pharmaceutical Company Limited
    Inventors: Motoaki Tanaka, Yu-ichi Hagiwara, Makoto Kajitani, Mitsugi Yasumoto
  • Patent number: 5136081
    Abstract: 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: Grant
    Filed: September 11, 1989
    Date of Patent: August 4, 1992
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventor: Paul H. Briner
  • Patent number: 5128479
    Abstract: 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: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5124083
    Abstract: There are disclosed 3-substituted and 3,3-disubstituted all-trans-4-oxoretinoic acids and 3-substituted and 3,3-disubstituted 13-cis-4-oxoretinoic acids and their lower alkyl esters.
    Type: Grant
    Filed: August 30, 1990
    Date of Patent: June 23, 1992
    Assignee: Southern Research Institute
    Inventor: Y. Fulmer Shealy
  • Patent number: 5118833
    Abstract: The invention provides a novel process for produing .alpha. -keto-carboxylic acid esters that are useful as intermediates for the preparation of pharmaceutical drugs in high yield by oxidizing .alpha. -hydroxycarbocylic acid esters with hypochlorous acid in the presence of nitroxy radical.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: June 2, 1992
    Assignee: Kuraray Company, Ltd.
    Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5112864
    Abstract: This invention relates to novel compounds for treating inflammatory conditions by inhibition of phospholipase A.sub.2 activity of the formula ##STR1## wherein X is oxygen, sulfur or --CH.dbd.CH--; wherein R.sup.1 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R.sup.2 is phenoxy, alkoxy, methyl, trifluoromethyl or phenyl;wherein n is an integer from 1 to 20;compositions comprised of the novel compounds; and methods of treating inflammatory conditions with these compositions.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: May 12, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Richard A. Haack
  • Patent number: 5106407
    Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: April 21, 1992
    Assignee: The Dow Chemical Company
    Inventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
  • Patent number: 5093515
    Abstract: A 2-chloro-4,5-difluorobenzoyl compound of the formula: ##STR1## wherein R.sup.2 is a lower alkyl group, and R.sup.7 is a 2,4-difluorophenyl group or a 4-fluorophenyl group.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: March 3, 1992
    Assignees: Asahi Glass Company Ltd., Katayama Seiyakusho Co., Ltd.
    Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki, Ryonosuke Yoshida, Yoshiyuki Murakami
  • Patent number: 5086067
    Abstract: 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.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: Grant
    Filed: December 18, 1989
    Date of Patent: February 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Patent number: 5077429
    Abstract: The invention relates to 7-amino-1-cyclo-propyl-4-oxo-1,4-dihydro-naphthyridine (or quinoline)-3-carboxylic acids of Formula I as defined in the specification. Also included in the invention is a process for the preparation of said compounds of Formula I and Ia. Further, the invention includes compositions containing the compounds of Formula I or Ia and the use of said compounds and compositions as antibacterial agents.
    Type: Grant
    Filed: April 1, 1986
    Date of Patent: December 31, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Hans-Joachim Zeiler, Karl G. Metzger
  • Patent number: 5075319
    Abstract: Fluorinated 1-cyclopropyl-7-(substituted-pyridinyl)-1,4-dihydro-4-oxo-3-quinolinecarbo xylic acids of the formula ##STR1## wherein R is hydrogen, R' and R" are hydrogen or fluoro, or other groups and Z is 3- or 4-pyridinyl substituted by alkyl groups or substituted alkyl groups, are superior antibacterial agents. They are prepared via a coupling reaction between the corresponding esters (R=alkyl) having a halo group in the 7-position and a substituted (trialkylstannyl)pyridine.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: December 24, 1991
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh, Michael Reuman
  • Patent number: 5068393
    Abstract: An aromatic deviative of butyric acid has the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, each independently, represent hydrogen or alkyl, with at least two of R.sub.1 -R.sub.4 being other than hydrogen,A represents methylene or dimethylene; when A represents dimethylene, R.sub.1 and R.sub.3 can together form methylene or dimethylene,R.sub.5 and R.sub.6 represent hydrogen, halogen, alkyl, alkoxy or hydroxy,R' represents hydrogen, hydroxy, alkoxy or acyloxy,R" represents hydrogen or alkoxy, or R' and R" taken together form oxo or hydroxyimino,R.sub.8 represents hydrogen or alkyl andR.sub.7 represents --OR.sub.9 or ##STR2## R.sub.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: November 26, 1991
    Assignee: Societe Anonyme Dite: L'Oreal
    Inventors: Jean Maignan, Gerard Malle, Gerard Lang
  • Patent number: 5055472
    Abstract: The present invention provides a compound of the formula: ##STR1## process for their production, pharmaceutical compositions containing them and their pharmaceutical uses, and intermediates useful for their production and processes for the production of such intermediates.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: October 8, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Yoshihiro Fujikawa, Mikio Suzuki, Hiroshi Iwasaki, Mitsuaki Sakashita, Masaki Kitahara
  • Patent number: 5051527
    Abstract: The invention lies in novel ferroelectric liquid crystal compounds particularly represented by the general formulae, having a good responsibility in relation to the applied electric field and a wide range of phase transition points inclusive of the room temperature so as to be useful alone as the liquid crystal material but also to be mixed with other liquid crystal compounds for expanding the phase transition points to a desired range and making the response speed of the liquid crystal composition faster. ##STR1## In the formulae, m and n are same or different with each other and represent an integral of 1-20.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: September 24, 1991
    Assignee: Showa Shell Sekiyu K.K.
    Inventors: Yoshiichi Suzuki, Takashi Hagiwara, Hiroyuki Mogamiya
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base 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.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5041681
    Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.2 X' in the presence of a base, wherein X' is a leaving group.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: August 20, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Glynn Mitchell
  • Patent number: 5039672
    Abstract: Certain spirocyclic heterocyclic compounds, and their pharmaceutically-acceptable salts, are inhibitors of the aldose reductase enzyme, and so are useful for the control of diabetic complications. Exemplary compounds include compounds of the formula ##STR1## wherein Y is ##STR2## X is --O-- or ##STR3## R.sub.1 and R.sub.2 are each independently H, alkyl C.sub.1 -C.sub.6,aryl or arylalkyl (C.sub.1 -C.sub.6);W.sub.1 and W.sub.2 are each independently hydrogen, halogen or nitro; andthe pharmaceutically acceptable base addition salts thereof.
    Type: Grant
    Filed: April 5, 1990
    Date of Patent: August 13, 1991
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Eric R. Larson
  • Patent number: 5026898
    Abstract: A process for regioselectively preparing phosphorylated cyclitols, in particular phosphorylated inositols such as myo-inositol 1,4,5-tris(phosphate) and muo-inositol 1,3,4,5-tetrakis(phosphate). Novel cyclitols produced by means of this process are also described.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: June 25, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Frank W. Hobbs, James L. Meek
  • Patent number: 5011944
    Abstract: .alpha.-Pyrones of the formula I ##STR1## in which R.sup.1 is --CF.sub.3 or --COOR.sup.3 and R.sup.3 is the radical of a C.sub.1 -C.sub.18 alcohol diminished by a hydroxyl group, and R.sup.2 is --F, --Br, --Cl, --CN, --CF.sub.3, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.2 -C.sub.18 alkynyl, C.sub.1 -C.sub.18 alkoxy, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 alkylsulfonyl, C.sub.6 -C.sub.16 aryl, C.sub.7 -C.sub.24 alkaryl, C.sub.7 -C.sub.12 aralkyl, C.sub.8 -C.sub.24 alkaralkyl, C.sub.6 -C.sub.16 aryloxy, C.sub.6 -C.sub.16 arylthio, C.sub.6 -C.sub.16 arylsulfonyl, C.sub.7 -C.sub.24 alkaryloxy, C.sub.7 -C.sub.24 alkarylthio, C.sub.7 -C.sub.24 alkarylsulfonyl, C.sub.7 -C.sub.12 aralkyloxy, C.sub.7 -C.sub.12 aralkylthio, C.sub.7 -C.sub.12 aralkylsulfonyl, C.sub.8 -C.sub.24 alkaralyloxy, C.sub.8 -C.sub.24 alkaralylthio, C.sub.8 -C.sub.24 alkaralylsulfonyl, secondary amine having 2 to 24 C atoms or trialkylsilyl or trialkoxysilyl each of which has 3 to 18 C atoms.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: April 30, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Vratislav Kvita, Marcus Baumann, Walter Fischer, Carl W. Mayer, Thomas Allmendinger
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 5001253
    Abstract: A fluorescent brightener is proposed which consists of 51-99% of an unsymmetrically substituted compound of the formula ##STR1## in which R and R.sub.1 are identical or different and, if R and R.sub.1 are identical, R.sub.1 must occupy a position in the phenyl ring to which it is bonded which differs from the position occupied by R in its phenyl ring, and in which R and R.sub.1 independently of one another are CN or a corboxylic acid ester group, and 49-1% of a symmetrically substituted compound of the formula ##STR2## in which R is as defined above and the two R's are bonded to identical positions in their phenyl rings, as are also agents which contain these fluorescent brighteners and the use of these fluorescent brighteners for the fluorescent brightening of, in particular, textile materials, preferably made of polyester.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: March 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Leonardo Guglielmetti