Oxy, Not Bonded Directly To A Ring, In Same Side Chain As Carboxyl, Or Salt Thereof Patents (Class 562/470)
  • Patent number: 5440044
    Abstract: The present invention relates to a leukotriene-B.sub.4 analog according to formula I ##STR1## in which R.sup.1 is a COOR.sup.2 group, wherein R.sup.2 is a C.sub.2-4 -alkyl group;B is a C.sub.1-3 -alkylene group, a radical ##STR2## wherein R.sup.3 is a hydrogen atom or a carboxy or methoxycarbonyl group; ##STR3## . . . is a single or double bond; or optionally, their salts with physiologically compatible bases. The present invention also relates to the production of the latter leukotriene-B.sub.4 analogs and their use as pharmacological agents.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: August 8, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5428162
    Abstract: Novel compounds of the formula (1), ##STR1## in which R.sub.1 is hydrogen or acyl, R.sub.2 to R.sub.5 are independently hydrogen, chloro, alkyl phenylalkyl, aryl, cycloalkyl, alkoxy, alkylthio, hydroxy, amino or substituted amino, R.sub.6 is hydrogen, R.sub.7 to R.sub.10 are independently hydrogen, alkyl or alkoxy, R.sub.17 or R.sub.19 is hydrogen or alkyl, and R.sub.18 is hydrogen, alkyl, aralkyl or aryl, are described for use as stabilizers for organic materials against thermal, oxidative or light-induced degradation.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: June 27, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Nesvadba
  • Patent number: 5412112
    Abstract: Novel 3-substituted derivatives of 2,2-dimethyl-5-substituted phenoxy-pentanoic acids of formula (I) are prepared. These compouds are prepared from 2,2-dimethyl-5-substituted phenoxy-3-hydroxy-pentanoic acid-.beta.-lactones (formula II). The .beta.-lactones are prepared by condensing relevant phenoxypropanals with dimethylketene.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: May 2, 1995
    Assignee: Industrial Technology Research Institute
    Inventors: Hui-Po Wang, On Lee, Chin-Tsai Fan
  • Patent number: 5403952
    Abstract: Novel substituted cyclic 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, dystrophic epidermolysis bullosa, and coronary thrombosis associated with atherosclerotic plaque rupture. 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 be useful as novel birth control agents by preventing ovulation or implantation.
    Type: Grant
    Filed: October 8, 1993
    Date of Patent: April 4, 1995
    Assignee: Merck & Co., Inc.
    Inventors: William Hagmann, Charles G. Caldwell, Paul R. Gooley
  • Patent number: 5376683
    Abstract: The invention relates to .DELTA..sup.8 - and .DELTA..sup.9 -prostaglandin derivatives of formula I, ##STR1## in which means the radicals or , R.sup.1 means ##STR2## COOR.sup.4 or CONHR.sup.5, R.sup.2 and R.sup.3 respectively mean a hydrogen atom or a hydroxy group, and the OH group can be respectively in alpha- or beta- position,means a CH.sub.2 group, an O or S atom,W means hydrogen, --OR.sup.6, halogen, --CN--, --NO.sub.2, trifluoromethyl or COOR.sup.6, and if R.sup.4 means hydrogen, their salts with physiologically compatible bases, the alpha-, beta- or gamma- cyclodextrin clathrates, as well as the compounds of formula I encapsulated with liposomes, process for their production and their pharmaceutical use.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: December 27, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Ulrich Klar, Hartmut Rehwinkel, Helmut Vorbruggen, Karl H. Thierauch, Claus S. Sturzebecher
  • Patent number: 5371284
    Abstract: Phenyl acetylenic acetals and thioacetals and their use in the treatment of allergy, asthma, inflammation, arthritis, hyperproliferative skin disease, psoriasis or contact dermatitis are disclosed. Also disclosed are intermediates useful for producing said phenyl acetylenic acetals and thioacetals.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: December 6, 1994
    Assignee: Schering Corporation
    Inventors: Richard J. Friary, Michael J. Green, Anil K. Saksena, Vera A. Seidl
  • Patent number: 5362907
    Abstract: The present invention relates to novel 2-arylpropenoic acids, derivatives thereof, processes for their preparation and their use in the preparation of S-ketoprofen.
    Type: Grant
    Filed: August 21, 1992
    Date of Patent: November 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Laue, Georg Schroder, Dieter Arlt
  • Patent number: 5354897
    Abstract: Preparation process for orthohydroxymandelic acid, as well as its salts, in which glyoxylic acid is reacted with phenol in the presence of a tertiary amine and catalytic quantities of trivalent metal cations, in order to obtain the expected product which is isolated and, if desired, salified.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: October 11, 1994
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5348727
    Abstract: A compound of the formula: ##STR1## wherein Z.dbd.H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, alkoxycarbonyl, cyano, wherein thealkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.dbd.C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl; each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p -(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C-Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, or lower-alkyl, optionally substituted with halo;x is 1-4;n is [1-5]1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, these compounds are useful as X-ray contrast agents or aryl-lower alkyl.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: September 20, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef
  • Patent number: 5332857
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: July 26, 1994
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5310538
    Abstract: R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 =CR.sub.4).sub.m Q ,or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2 and R.sub.3 and R.sub.4 are independently H, or lower-alkyl, optionally substituted with halo;x is 1-4;n is 1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkylThese compounds are combined in a polymer for use as an X-ray contrast agent.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: May 10, 1994
    Assignee: Sterling Winthrop Inc.
    Inventors: Edward R. Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef
  • Patent number: 5301693
    Abstract: This invention provides smoking compositions which contain a novel .beta.-hydroxycarboxylate flavorant-release additive. Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as calcium bis(2,2-diethyl-3-hydroxy-4-phenylmethylenedecanoate) pyrolyzes and releases .alpha.-hexylcinnamaldehyde as a volatile flavorant component of the cigarette smoke.
    Type: Grant
    Filed: July 9, 1992
    Date of Patent: April 12, 1994
    Assignees: Philip Morris Incorporated, Philip Morris Products Inc.
    Inventors: W. Geoffrey Chan, William B. Edwards, III, Harvey J. Grubbs, Yoram Houminer, Charles R. Howe, John D. Naworal, John B. Paine, III, Kenneth F. Podraza, Edward B. Sanders, Jeffrey I. Seeman, Everett W. Southwick
  • Patent number: 5286895
    Abstract: An acyclic tricarboxylic compound has been isolated from a culture of MF5453. The compound and its derivatives are active as squalene synthetase inhibitors and are useful in the treatment of hypercholesterolemia.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 15, 1994
    Assignee: Merck & Co., Inc.
    Inventors: Guy H. Harris, Henry Joshua, Deborah L. Zink
  • Patent number: 5274155
    Abstract: A process for the preparation of compounds of formula ##STR1## and pharmaceutically acceptable salts thereof; wherein X is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or --CH.sub.2 O-- (where O is linked to Z); Z is a hydrophobic anchor R.sub.1 is hydrogen, alkyl, cycloalkyl or aryl; comprising the steps of:(A) reacting a compound of formula ##STR2## with a compound of formula ##STR3## or a compound of formula ##STR4## in the presence of an amine base or an alkali metal hydride in an organic solvent to form a compound having the formula ##STR5## (B) heating the compound of formula IX at a temperature of from about 100.degree. C. to about 200.degree. C., to form a compound of formula ##STR6## and (C) quenching the compounds of formula VIII with an acid provides the compounds of formula I.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: December 28, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: John K. Thottathil, David Kronenthal
  • Patent number: 5254727
    Abstract: Two acyclic tricarboxylic acid compounds have been isolated from the fermentation of Sporormiella intermedia. The compounds and their derivatives may be used as antifungal agents, cholesterol lowering agents and as anticancer agents.
    Type: Grant
    Filed: October 19, 1992
    Date of Patent: October 19, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Claude Dufresne, E. Tracy T. Jones, Leslie A. Ferrell
  • Patent number: 5248816
    Abstract: A method for the preparation of a 2-hydroxymandelic acid of the formula ##STR1## wherein R represents an alkyl radical containing from 7 to 12 carbon atoms which comprises reacting glyoxylic acid with a phenol of the formula: ##STR2## under acid conditions. Oxidation of the 2-hydroxymandelic acid to the corresponding 2-hydroxybenzaldehyde is also described.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ralph Shuttleworth, Jan M. Fielden, Daniel Levin
  • Patent number: 5246966
    Abstract: The new substituted alkenoic acid derivatives can be prepared by reacting the appropriate aldehyde with a phosphonium compound. The compounds have leukotriene antagonistic properties and can be incorporated into pharmaceutical compositions.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: September 21, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Meier, John E. B. Ransohoff, Trevor S. Abram, Peter Norman, Tudhope Stephen R., Phillip J. Gardiner, Nigel J. Cuthbert, Hilary P. Francis
  • 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: 5216024
    Abstract: The present invention discloses new and useful compounds including methyl p-hydroxyphenyllactate, its analogues, chemical derivatives and chemically related compounds and their use as antitumor agents, as inhibitors of proliferative cell growth and as prophylactic agents to inhibit and prevent cancer and non-malignant cell growth.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: June 1, 1993
    Assignee: Baylor College of Medicine
    Inventors: Barry M. Markaverich, James H. Clark, Rebecca Gregory, Mary Alejandro, Brian S. Middleditch, Gregory A. Johnson, Rajender S. Varma
  • Patent number: 5176850
    Abstract: The present invention provides a composition in contact with a corrodable metal surface, comprising a functional fluid and, as corrosion inhibitor, a compound having the formula 1A ##STR1## as well as salts or esters thereof, wherein R.sup.3 is C.sub.9 -C.sub.20 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl;R.sup.4 is C.sub.1 -C.sub.3 alkyl;X is CH.sub.2, O or S;Y is O or S; andZ is--(CH.sub.2).sub.n -in which n is 1,2,3,4 or 5, or Z is--CH.sub.2 --CH(CH.sub.3)-.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: January 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert M. O'Neil
  • Patent number: 5166377
    Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: November 24, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett
  • Patent number: 5166171
    Abstract: 6-Phenoxymethyl-4-hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, processes for the preparation of these compounds, their use as pharmaceuticals, pharmaceutical preparations and novel phenols and thiophenols Compounds of the general formula I ##STR1## and the corresponding open-chain dihydroxycarboxylic acids of the formula II ##STR2## in which X, Y and Z have the meanings given, and pharmacologically tolerated salts thereof with bases and pharmacologically tolerated esters thereof, processes for the preparation of these compounds, their use as pharmaceuticals and pharmaceutical preparations are described. Novel phenols and thiophenols of the formula III ##STR3## in which X, Y and Z have the meanings given, are also described.
    Type: Grant
    Filed: April 2, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Jendralla, Gunther Wess, Wilhelm Bartmann, Gerhard Beck
  • Patent number: 5151545
    Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: September 29, 1992
    Assignee: Pfizer Inc.
    Inventors: Peter A. McCarthy, Frederick J. Walker
  • Patent number: 5145611
    Abstract: Carboxylic acid derivatives of the formula ##STR1## R.sub.1 is alkoxy, alkylthio, alkylsulphinyl, alkulsulphonyl, alkylamino, cycloalkyl, or cycloalkoxy or optionally substituted aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl or arylamino. R.sub.2 is optionally substituted aryl or, when B is alkylene also a hydrogen atom. A is a straight-chained or branched, saturated or unsaturated alkylene containing 3 to 10 carbon atoms which is optionally interrupted by a heteratom attached to a saturated carbon and has a chain length of at least 3 atoms. Y is S(O).sub.n group or oxygen, n being 0, 1 or 2. B is a valency bond or a straight-chained or branched, saturated or unsaturated alkylene containing 1 to 18 carbon atoms. Physiologically acceptable salts, esters and amides thereof are also included. The compounds are useful in the treatment of metabolic diseases.
    Type: Grant
    Filed: January 12, 1988
    Date of Patent: September 8, 1992
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuehnle
  • Patent number: 5142063
    Abstract: The present invention describes novel chiral rhodium-diphosphine complexes having the formula[Rh(X) (Y) (Lp)]owherein X represents a residue of the formula X--COO.sup.- in which Z signifies a group ##STR1## aryl or substituted aryl, wherein R.sup.1, R.sup.2, R.sup.3 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro-C.sub.1-20 -alkyl, aryl, substituted aryl, the group --OR.sup.7, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n, with the proviso that at least one of R.sup.1, R.sup.2, and R.sup.3 represents --OR.sup.7, aryl or substituted aryl,R.sup.4, R.sup.5, R.sup.6 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro--C.sub.1-20 -alkyl, aryl, substituted aryl, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n,R.sup.7 =hydrogen, lower alkyl, partially or completely halogenated lower alkyl, aryl, substituted aryl or aryl-lower alkyl,A=The residue --OR or NR'.sub.
    Type: Grant
    Filed: November 20, 1990
    Date of Patent: August 25, 1992
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Emil A. Broger, Yvo Crameri
  • Patent number: 5116981
    Abstract: This invention encompasses novel analogs of Leukotriene B.sub.4 which are selected from a compound of formula I, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--Y--C(M.sub.1)--A, or formula II, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--P--R.sub.5 --A: wherein Y is: ##STR1## wherein P is: ##STR2## Patentable intermediates, process for making the novel analogs and intermediates and preparation of useful pharmacological agents comprising the analogs and intermediates are part of this invention.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: May 26, 1992
    Assignee: The Upjohn Company
    Inventor: Joel Morris
  • Patent number: 5093363
    Abstract: A 2,4,6-substituted phenol having the formula (I): ##STR1## wherein X is S or CH.sub.2 ; R.sup.1 and R.sup.2 are the same or different from each other and each is a lower alkyl group; R.sup.3 is a group of the formula: ##STR2## in which R.sup.4 is hydrogen atom or a lower alkyl group; R.sup.5 and R.sup.6 are the same or different from each other and each is hydrogen atom, a lower alkyl group, or a phenyl group which may be substituted,or a pharmaceutically acceptable salt thereof is useful as an active agent in a pharmaceutical composition. The pharmaceutical composition comprises a therapeutically effective amount of a compound having the formula (I), as an effective ingredient, in association with a pharmaceutically acceptable substantially nontoxic carrier or excipient. The pharmaceutical composition can be useful in the treatment of lipemia of mammals. Additionally the compounds can be used as antiatherosclerotic agents and antilipenic agents.
    Type: Grant
    Filed: August 14, 1990
    Date of Patent: March 3, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Toru Kita, Hiroshi Harada, Eiichi Ohsugi, Toshiro Konoike
  • Patent number: 5091113
    Abstract: R is a straight or branched chain C.sub.4 -C.sub.30 alkyl group, a straight or branched chain C.sub.4 -C.sub.30 alkyl group interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C.sub.5 -C.sub.12 cycloalkyl group, a C.sub.6 -C.sub.10 aryl group, C.sub.6 -C.sub.10 aryl group substituted by one, two or three C.sub.1 -C.sub.12 alkyl groups, a C.sub.7 -C.sub.13 aralkyl group or a C.sub.7 -C.sub.13 aralkyl group which is substituted by a hydroxyl group;R.sub.1 is H or a straight- or branched chain C.sub.1 -C.sub.4 alkyl group;R.sub.2 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group or CO.sub.2 H;R.sub.3 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, --CH.sub.2 CO.sub.2 H or --CH.sub.2 CH.sub.2 CO.sub.2 H;R.sub.4 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl or CO.sub.2 H;R.sub.5 is H, a straight or branched chain C.sub.1 -C.sub.4 alkyl group, CH.sub.2 CO.sub.2 H or CH.sub.2 CH.sub.2 CO.sub.
    Type: Grant
    Filed: July 27, 1990
    Date of Patent: February 25, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Brian G. Clubley
  • Patent number: 5072008
    Abstract: The invention concerns a novel process for the stereospecific manufacture of novel hydroxymethyl lactols of the formula I by a one step reduction of a corresponding lactone carboxylic ester of the formula II (many of which esters are novel) using a reducing agent such as diisobutylaluminium hydride at about ambient temperature. The lactols of formula I are intermediates for the production of pharmacologically active 1,3-dioxane alkenoic acids useful in the treatment of certain cardiovascular and pulmonary medical conditions. Certain of the esters of formula II are novel and are also included in the invention.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: December 10, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Gregory D. Harris
  • Patent number: 5066815
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 19, 1991
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 5041638
    Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
  • Patent number: 5004754
    Abstract: The invention relates to a biofungicidal composition characterized by its capacity to arrest the growth and/or destroy the cell wall of pathogenic fungi, comprises a composition of a compound of the formula I ##STR1## wherein R.sub.1 is selected from the group consisting of ##STR2## and R.sub.2 is --H or --OH and mixtures thereof in association with an inert carrier, and to a method for arresting the growth and/or destroying the cell wall of pathogenic fungi by applying thereto a biofungicidal amount of the composition of a compound of formula I in association with an inert carrier.
    Type: Grant
    Filed: June 5, 1989
    Date of Patent: April 2, 1991
    Assignee: Universite Laval
    Inventors: J. Andre Fortin, Kelvin K. Ogilvie, Youla S. Tsantrizos, Harry H. Kope
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4992563
    Abstract: This invention relates to several intermediates useful in preparing thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)-thioxomethyl]hydrazono]ethyl]-1.alpha ., 4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha., 7a.alpha.-4.alpha.,7.alpha.-methano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: February 12, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • Patent number: 4983766
    Abstract: An aldehyde (R.sup.1 CHO) and optically active 3-hydroxybutyric acid (CH.sub.3 CH(OH)CH.sub.2 COOH) are reacted to form an optically active dioxanone. This dioxanone is reacted with a compound R.sup.2 --X to form an intermediate (R.sup.1 R.sup.2 CHOCH(CH.sub.3) CH.sub.2 COOH) which is then subjected to elimination to form an optically active secondary alcohol (R.sup.1 R.sup.2 CHOH) in good yield and purity.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: January 8, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Rene Imwinkelried, Dieter Seebach
  • Patent number: 4978784
    Abstract: This process is characterized by the fact that glyoxylic acid in aqueous solution is reacted with an excess of phenol in the presence of a tertiary amine, insoluble or slightly soluble in water and liquid at ambient temperature, in particular tributylamine or triisooctylamine, then the parahydroxymandelic acid thus obtained is salified with sodium hydroxide in aqueous solution.The reaction of the glyoxylic acid with phenol is carried out at a temperature between 15.degree. C. and 80.degree. C.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: December 18, 1990
    Assignee: Societe Francaise Hoechst
    Inventor: Yani Christidis
  • Patent number: 4968837
    Abstract: Racemic 2-(N-propylamino)-5-methoxytetralin is resolved by treating it with a chiral diaroyltartaric acid in an organic solvent at an elevated temperature to form a salt of the amine and chiral diaroyltartaric acid which is soluble in the solvent at the elevated temperature, cooling to precipitate the salt, isolating it, and converting it to the free amine. The product is useful as an intermediate in the synthesis of optionally-active pharmaceutical, such as N-0437.
    Type: Grant
    Filed: July 28, 1989
    Date of Patent: November 6, 1990
    Assignee: Ethyl Corporation
    Inventors: Thanikavelu Manimaran, Fred J. Impastato
  • Patent number: 4956474
    Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: September 11, 1990
    Assignee: Mochida Pharmaceutical Co., Ltd.
    Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
  • Patent number: 4922010
    Abstract: There are disclosed a process for preparing 2-hydroxy-2-(6-methoxy-2-naphthyl)propionic acid or 2-hydroxy-(4-substituted phenyl)propionic acid derivative which comprises reacting 2-methoxynaphthalene or substituted benzene derivatives with pyruvic acid in the presence of a Lewis acid and then, if necessary, hydrolyzing the obtained product, and a process for preparing 2-(6-methoxy-2-naphthyl)propionic acid or 2-(4-substituted phenyl)propionic acid derivative which comprises reducing 2-hydroxy-2-(6-methoxy-2-naphthyl)propionic acid or 2-hydroxy-2-(4-substituted phenyl)propionic acid derivative in a lower aliphatic acid in the presence of an inorganic acid under hydrogen atmosphere by using a metal catalyst.
    Type: Grant
    Filed: December 7, 1988
    Date of Patent: May 1, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Mikito Kashima, Hideo Ishikawa, Kouichi Kashiwagi, Yumiki Noda
  • Patent number: 4904822
    Abstract: A process for the optical resolution of (.+-.)-2-hydroxy-4-phenylbutanoic acid which comprises treating (.+-.)-2-hydroxy-4-phenylbutanoic acid with an optically active 1-(p-tolyl)ethylamine or an optically active N-(2-hydroxy)ethyl-.alpha.-methylbenzylamine as a resolving agent is provided by the present invention.According to the invention, (-)-2-hydroxy-4-phenylbutanoic acid, which is useful as a starting substance for the synthesis of angiotensin converting enzyme-inhibiting pharmaceuticals, can especially be obtained in a highly pure state and in a high yield.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: February 27, 1990
    Assignee: Kuraray Co., Ltd.
    Inventors: Hiroyuki Nohira, Shinichi Yoshida
  • Patent number: 4904823
    Abstract: There is described a process for the manufacture of hydroquinone derivatives of the formulae ##STR1## which are valuable intermediates in the synthesis of natural vitamin E.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: February 27, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4902709
    Abstract: Novel antihypercholesterolemic compounds of structure (I) or (II), ##STR1## pharmaceutically acceptable salts, thereof and a novel process for preparing compounds of structure I, are disclosed.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: February 20, 1990
    Assignee: Merck & Co., Inc.
    Inventor: Gerald E. Stokker
  • Patent number: 4857551
    Abstract: A method of killing or controlling insect, mite or nematode pests which method comprises applying to the insect or to the locus thereof an effective amount of a compound of the formula (I): ##STR1## wherein R is hydrogen or C.sub.1-4 alkyl; and X, Y and Z are independently selected from hydrogen, halogen, or OR.sup.1 where R.sup.1 is optionally substituted aryl or heteroaryl group. Certain of the compounds are new.
    Type: Grant
    Filed: August 31, 1987
    Date of Patent: August 15, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: David J. Tapolczay, Mark A. Spinney
  • Patent number: 4855320
    Abstract: The present invention provides 5-arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR1## wherein the oxygen atoms on C-5 and C-.alpha., relative to one another, are in the threo-position, with the exclusion of those compounds of the formula (I) wherein R.sup.2 is H or CH.sub.3 when n=0 or 2, R.sup.o =H, R.sup.1 =CH.sub.3, R.sup.3 =H and R.sup.4 =H.The present invention also provides processes for their preparation, as well as new 3-alkoxy-5-(subst.)-phenyl-2(E), 4(E)-pentadienoates as reactive intermediates for the preparation of the new furanone derivatives.The new furanone derivatives of the threo series are active as anticonvulsives/anti-epileptics. Therefore, the present invention also provides medicaments which contain these new furanone derivatives, as well as known furanones, the anticonvulsive/anti-epileptic effectiveness of which has been found for the first time.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: August 8, 1989
    Assignee: Dr. Willmar Schwabe GmbH & Company
    Inventors: Shyam S. Chatterjee, Klaus Klessing
  • Patent number: 4855324
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or .dbd.O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.
    Type: Grant
    Filed: February 18, 1988
    Date of Patent: August 8, 1989
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Stella S. Yu
  • Patent number: 4855323
    Abstract: Leukotriene antagonists, a process for the preparation thereof, and the use thereof for the treatment of diseases ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and X have the indicated meanings, a process for the preparation of these compounds, the use thereof as pharmaceuticals, and pharmaceutical products based on these compounds, are described.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: August 8, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Wess, Wilhelm Bartmann, Gerhard Beck, Hiristo Anagnostopulos
  • Patent number: 4851440
    Abstract: Leukotriene antagonists, processes for the preparation thereof, the use thereof for the treatment of diseases, and precursors.Compounds of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the indicated meanings, processes for the preparation of these compounds, the use thereof as pharmaceuticals, and pharmaceutical products based on these compounds are described. In addition, precursors for the preparation of compounds of the formula I are described.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: July 25, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Beck, Peter Below, Andreas Bergmann
  • Patent number: 4837354
    Abstract: Disclosed herein is a novel compound, (L)-menthyl 2-oxo-4-phenylbutyrate, and an improved process for making and isolating a substantially pure compound of the structural formula: ##STR1## wherein Y is hydrogen or (L)-menthyl the improvement which comprises: (a) stereoselectively reducing (L)-menthyl 2-oxo-4-phenylbutyrate by contacting said compound with S-B-(3-pinanyl)-9 horabicyclo[3,3,1]nonone,(b) stereoselectively isolating (L)-menthyl-(R)-2-hydroxy-4-phenylbutyrate by crystallization, and optionally hydrolyzing the so obtained ester;and further comprises optionally esterifying the so obtained acid by contacting said acid with a C.sub.1 -C.sub.6 alkanol in presence of acid.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: June 6, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Gary A. Flynn, Douglas W. Beight
  • Patent number: 4831147
    Abstract: Racemic mixtures of 2-(4-aryloxyphenoxy)propionic acids are resolved into their optically active enantiomers by dissolving the racemate with at least one equivalent of a cinchona alkaloid in a halogenated hydrocarbon solvent and by extracting with a polyhydroxylic solvent.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: May 16, 1989
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell