Oxy, Bonded Directly To A Ring, In Same Side Chain As Carboxyl, Or Salt Thereof Patents (Class 562/471)
  • Patent number: 5463059
    Abstract: A process for preparing compounds of the formula ##STR1## where a, b, c, R.sub.1, R.sub.2, and R.sub.3 are as defined herein including the step of alkylating a phenol of formula ##STR2## with an acetylene of formula ##STR3## where X is chlorine; bromine; --OC(O)--R.sub.5, where R.sub.5 is alkyl, aryl or substituted aryl; or --OCO.sub.2 R.sub.6, where R.sub.6 is alkyl or ##STR4## in the presence of a catalytic amount of a cuprous or cupric salt. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.
    Type: Grant
    Filed: October 1, 1993
    Date of Patent: October 31, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jollie D. Godfrey, Jr., Richard H. Mueller, Thomas C. Sedergran, Nachimuthu Soundararajan
  • Patent number: 5462954
    Abstract: Antagonists having a substituted phenyl phenol or a substituted phenolic biphenyl structure, and various derivatives thereof, are specific leukotriene antagonists. Their structures, use and synthesis are disclosed. Also, pharmaceutical formulations are disclosed for use in applications treating diseases or conditions characterized by excessive release of leukotriene B.sub.4, one of the metabolites of arachidonic acid.The primary LTB.sub.
    Type: Grant
    Filed: November 1, 1994
    Date of Patent: October 31, 1995
    Assignee: Eli Lilly and Company
    Inventors: S. Richard Baker, Robert D. Dillard, Paul E. Floreancig, J. Scott Sawyer, Michael J. Sofia
  • Patent number: 5458678
    Abstract: There are described novel alkaline earth metal salts, transition metal salts and transition metal complexes of compounds of the formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are, independently of one another, hydrogen, halogen, nitro, cyano, CF.sub.3, C.sub.1 -C.sub.15 alkyl, C.sub.5 -C.sub.12 cycloalkyl, C.sub.2 -C.sub.15 alkenyl, C.sub.1 -C.sub.12 haloalkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.12 alkylthio, C.sub.6 -C.sub.10 aryl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; C.sub.6 -C.sub.10 aryloxy which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; C.sub.7 -C.sub.12 arylalkyl which is unsubstituted or substituted on the aryl radical by from 1 to 3 C.sub.1 -C.sub.4 alkyl groups; --CO.sub.2 R.sub.6, --COR.sub.6 or ##STR2## where at least one of the radicals R.sub.1 to R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.15 alkyl, in addition the radicals R.sub.1 and R.sub.2, R2 and R.sub.3, R.sub.3 and R.sub.4 or R.sub.4 and R.sub.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: October 17, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: William P. Armstrong, Adalbert Braig, Markus Frey, Andreas Kramer
  • 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: 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: 5352701
    Abstract: 1. Leukotriene-B.sub.4 antagonists of formula I ##STR1## are described, in which X is a CH.sub.2 group or an oxygen atom,Y is C.sub.1 -C.sub.4 -alkoxy or --S(O).sub.p --C.sub.1 -C.sub.4 -alkyl,p is 0, 1 or 2Z is a hydrogen atom or the radical A-B-COOH with A being a hydroxymethylene group or a carbonyl group and B being an alkylene group with 1-6 atoms in the chain or a radical ##STR2## with the exception that B cannot mean the radical ##STR3## if X is a CH.sub.2 group, R.sub.1 is the radical OH, --O--(C.sub.1 --C.sub.4) -alkyl, --O--(C.sub.3-C.sub.6) -cycloalkyl, --O--(C.sub.7-C.sub.12) -aralkyl or the radical NHR.sub.4 with R.sub.4 being hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.6)-cycloalkyl, C.sub.6 -C.sub.10 -aryl or (C.sub.7 -C.sub.12)-aralkyl as well as their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their use as pharmaceutical agents.
    Type: Grant
    Filed: May 5, 1993
    Date of Patent: October 4, 1994
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5334753
    Abstract: A novel process for the synthesis of ortho-substituted benzoic acid by lithiating an unprotected benzoic acid and a number of novel orth-substituted benzoic acids are described.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: August 2, 1994
    Assignee: Rhone-Poulenc Agriculture Ltd
    Inventors: Bernard Bennetau, Paul A. Cain
  • Patent number: 5324857
    Abstract: Reaction of amine-containing substrates with hydrogen peroxide can suffer from certain problems, especially in the presence of transition metals. These problems include both in situ generation of impurities and particularly nitrosamines, which are allegedly carcinogenic, and also impaired product formation. The problems can be ameliorated by employing in the reaction mixture free radical scavengers, including in particular phenols and polyhydroxy-substituted aromatic compounds. The scavengers are advantageously employed in conjunction with a metal chelating agent such as polycarboxylic acid or an organopolyphosphonic acid.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: June 28, 1994
    Assignee: Solvay Interox
    Inventor: Noel S. Shehad
  • Patent number: 5290812
    Abstract: Phenoxyalkylcarboxylic acid derivatives represented by the following formula (I) ##STR1## having a strong and selective leukotriene antagonistic action and useful for prophylaxis and therapy of allergic diseases as asthma and processes of preparing the same.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: March 1, 1994
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Mitsuo Ohashi, Toshio Tanaka, Norihisa Ishikawa, Tetsuya Kishi
  • 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: 5250325
    Abstract: Coating composition comprising:A) an organic film-forming binder; andB) a corrosion-inhibiting amount of a water-insoluble salt of i) a carboxylic acid having the formula (I): ##STR1## and ii) a base selected from a) a cation of Group Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, VIa, VIIa or VIIIa of the Periodic Table of Elements, b) an amine of formula II: ##STR2## c) a guanidine of formula III:R.sub.7 --N.dbd.C(NH.sub.2).sub.2 IIId) an amidine of formula IV:R.sub.7 --C(.dbd.NH)NH.sub.2 IVor e) melamine.
    Type: Grant
    Filed: January 21, 1993
    Date of Patent: October 5, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Emyr Phillips, William P. Armstrong
  • Patent number: 5235092
    Abstract: A phenoxycetic acid derivative of the formula: ##STR1## wherein R is a hydroxyl group, an alkoxy group, a group of the formula OM wherein M is an alkali metal ion, an alkaline earth metal ion, a transition metal ion, an ammonium ion or an organic ammonium ion, or a group of the formula NHR.sub.1 wherein R.sub.1 is a hydrogen atom, a hydroxyl group, an amino group, an allyloxy group or an ethoxycarboxylmethoxy group.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: August 10, 1993
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Tetsuo Takematsu, Makoto Konnai
  • 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: 5183925
    Abstract: The invention relates to leukotriene-B.sub.4 derivatives of formula I, ##STR1## in which n=1-10,R.sub.1 means radical CH.sub.2 OH, radical COOR.sub.4, radical CONHR.sub.5 or radical CONR.sub.6 R.sub.7,A means a cis, trans or trans, trans--CH.dbd.CH--CH.dbd.CH group or tetramethylene group,B means an alkylene group with up to 10 C atoms,D means a direct compound, oxygen, sulfur, a --C.tbd.C group or a --CH.dbd.CR.sub.8 group,B and D together mean a direct bond,R.sub.2 means a hydrogen atom or an acid radical of an organic acid with 1-15 C atoms andR.sub.3 means a hydrogen atom, an optionally substituted alkyl radical with 1-10 C atoms,a cycloalkyl radical with 3-10 C atoms, an optionally substituted aryl radical with 6-10 C atoms or a 5-6 member heterocyclic radical and if R.sub.4 means a hydrogen atom, their salts with physiologically compatible bases and their cyclodextrin clathrates, process for their production and their pharmaceutical use.
    Type: Grant
    Filed: November 19, 1990
    Date of Patent: February 2, 1993
    Assignee: Schering Aktiengesellschaft
    Inventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Rolalnd Ederdt
  • 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: 5175349
    Abstract: The present invention relates to the use of nucleus-substituted 4-hydroxyphenyl propionic acid compounds for stabilizing organic polyisocyanates.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: December 29, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pramod Gupta, Christian Konig, Hans-Jurgen Rabe, Hans-Wilhelm Engels, Wilfried Nolte, Chiraranjan Podder
  • 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: 5155260
    Abstract: The invention relates to an improved process for the preparation of 2,2-dimethyl-5-(2,5-dimethylphenoxy)-pentanoic acid of Formula (I) ##STR1## which comprises reacting an ester of the general Formula (X) ##STR2## wherein X represents halogen and Z stands for a straight or branched chain C.sub.1-8 alkylene group optionally substituted by one or two 2,2-dimethyl-5-halopentanoyloxy group(s), wherein halo represents chlorine or bromine, and in which alkylene group one or two methylene group(s) may be optionally replaced either by hetero atom(s) or by a bivalent heterocyclic group--with an alkali salt of 2,5-dimethylphenol of Formula (II) ##STR3## or with an ester of the latter formed with a lower alkanoic acid, and hydrolizing the aryloxy-substituted ester of the general Formula (XI) thus obtained. Furthermore the invention relates to intermediate compounds of the general Formula (X), wherein X and Z are as stated above, and to a process for the preparation thereof.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: October 13, 1992
    Assignee: Egis Gyogyszergyar
    Inventors: Zoltan Zubovics, Gabor Feher, Lajos Toldi, Gabor Kovacs, Antal Simay, Eva Kovacs nee Bozo, Imre Moravcsik, Ferenc Szederkenyi, Gyorgy Krasznai, Gyorgyi Vereczkey nee Donath, Kalman Nagy
  • Patent number: 5145992
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: September 8, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis
  • Patent number: 5140046
    Abstract: Novel phenylene derivatives shown by the general formula ##STR1## where A represents a hydrogen atom, a phenyl group or a phenoxy group, n represents an integer of 3 to 10, R.sub.1 represents a hydrogen atom or a lower alkoxy group, X.sub.1 represents --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CONH--, B represents ##STR2## wherein R.sub.2 represents a hydrogen atom, a halogen atom, a nitro group, etc.), ##STR3## (wherein R.sub.3 represents a hydrogen atom, a hydroxyl group or a lower alkoxy group), X.sub.2 represents --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, etc. and D represents a carboxy group, a lower alkoxycarbonyl group or ##STR4## which are useful as drugs, particularly SRS-A(slow reacting substance of anaphylaxis) antagonist, i.e. they are useful as prophylaxis and treatment for various allergic diseases (e.g. bronchial asthma, allergic rhinitis, urticaria) or, ischemic heart diseases, inflammation, etc. induced by SRS-A.
    Type: Grant
    Filed: August 13, 1990
    Date of Patent: August 18, 1992
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Toshiyasu Mase, Kiyoshi Murase, Hiromu Hara, Kenichi Tomioka
  • Patent number: 5098613
    Abstract: This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: March 24, 1992
    Assignee: Eli Lilly and Company
    Inventors: Nancy G. Bollinger, Theodore Goodson, Jr., David K. Herron
  • Patent number: 5043257
    Abstract: Azo dyes of the formula ##STR1## where X is alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, X' is hydrogen, alkyl or alkoxy each of 1 to 4 carbon atoms or halogen, Y and Y' are independently of each other hydrogen or halogen, Z is hydrogen, alkyl or alkoxy or alkylthio each of 1 to 4 carbon atoms, or halogen, M is a 1-, 2- or 3-valent metal cation, ammonium or an organic ammonium compound, m is 1, 2 or 3 and n is 2 to 10, are suitable for use as image dyes in photographic silver dye bleach materials.The dyes of the invention can also be used to dye textile materials.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 27, 1991
    Assignee: Ilford Limited
    Inventors: Kurt Baettig, Gerald C. Jan
  • Patent number: 5041640
    Abstract: An improved process for the preparation of mono-, di-, or trisubstituted acetic acids including 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid by a novel synthesis is described where a carboxylic acid is converted to a soluble metalated magnesium or zinc carboxylate containing a ligand and subsequent alkylation of this intermediate in the presence of an alkali amide to afford the desired product in two steps.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: August 20, 1991
    Assignee: Warner-Lambert Company
    Inventor: Paul L. Creger
  • 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: 5028733
    Abstract: Bicyclooctane and bicycloheptane prostaglandin intermediates have been synthesized.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: July 2, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 5013482
    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 I: ##STR1## as well as salts or esters thereof, wherein R.sup.1 is C.sub.4 -C.sub.20 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl;R.sup.2 is C.sub.1 -C.sub.12 linear or branched alkyl, phenyl or C.sub.7 -C.sub.20 alkylphenyl, or arylalkyl containing 7-20 carbon atoms;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)--.Some of the compounds of formula I are new.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: May 7, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert M. O'Neil
  • Patent number: 5013864
    Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: May 7, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
  • Patent number: 5004832
    Abstract: Compounds are described of formula ##STR1## in which: Ar represents an aryl, possibly substituted;R represents a C.sub.1 -C.sub.4 alkyl;R' represents a hydroxyl, an alkoxy, an amino group possibly mono or di-alkyl substituted, or an O.sup.-- M.sup.+ group where M.sup.+ represents the cation of an alkaline metal;X represents a hydrogen, chlorine, bromine or iodine atom, a hydroxyl, or an acyloxy, alkylsulphonyloxy or arylsulphonyloxy group.The compounds of formula I can be easily transformed into alpha-arylalkanoic acids of formula ##STR2## in which Ar and R have the aforesaid meanings.
    Type: Grant
    Filed: February 6, 1989
    Date of Patent: April 2, 1991
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4981998
    Abstract: A process for the preparation of D-hydroxyphenoxypropionic acid and its purification from its reaction mixture containing the acid, together with inorganic salts and various organic impurities, by crystallization of D-hydroxyphenoxypropionic acid by cooling followed by washing the crystals of D-hydroxyphenoxypropionic acid by elution.
    Type: Grant
    Filed: July 20, 1989
    Date of Patent: January 1, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventor: Jose Moyne
  • Patent number: 4960536
    Abstract: The invention relates to novel carboxyalkylated derivatives of alkyl and alkenyl catechol ethoxylates and to their use as surface active agents. The novel carboxyalkylated derivatives are especially useful as self-sequestering surfactants in detergent compositions.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 2, 1990
    Assignee: Sandoz Ltd.
    Inventor: Robert V. Casciani
  • Patent number: 4952724
    Abstract: A process for producing aryloxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R-OH wherein R is aryl or substituted aryl with a base in an aprotic organic solvent to give an aryloxide followed by removal of the organic solvent and reaction of the aryloxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding aryloxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the aryloxyacetate salt with an acid.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: August 28, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A, Partis
  • Patent number: 4950782
    Abstract: Polycarbonate resins are chain-terminated with a group selected from those of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently selected from the group consisting of hydrogen, halogen, hydrocarbyl of from 1 to 12 carbon atoms, inclusive; and halogen-substituted hydrocarbyl of 1 to 12 carbon atoms, inclusive; R.sub.1 is attached to a ring carbon atom at one of the 4, 5 or 6 positions; and R.sub.2 and R.sub.3 when taken together represent the divalent moiety of formula: --CH.dbd.CH.sub.2 --CH.sub.2 .dbd.CH--which effectively creates an additional fused aromatic ring structure. The resins exhibit a low plate-out when processed thermally.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: August 21, 1990
    Assignee: General Electric Company
    Inventors: Daniel W. Fox, Edward N. Peters, Paul D. Sybert
  • Patent number: 4935540
    Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, thallium and carbon to form the corresponding alkali metal ester and contacting the alkali metal ester with a mineral acid.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: June 19, 1990
    Inventor: Charles E. Sumner, Jr.
  • Patent number: 4933367
    Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: June 12, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
  • Patent number: 4917817
    Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.
    Type: Grant
    Filed: July 21, 1988
    Date of Patent: April 17, 1990
    Assignee: Canon Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
  • Patent number: 4910309
    Abstract: The optical purity of an optically active 2-(4-aryloxyphenoxy)propionic acid is enriched by formation of the hydrate of the enantiomer in excess and its removal from solution.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: March 20, 1990
    Assignee: The Dow Chemical Company
    Inventors: Larry D. Kershner, Jimmy J. Tai
  • Patent number: 4908476
    Abstract: A method for synthesizing 2-(4-hydroxyphenoxy)alkanoic acids by reacting a hydroxyaromatic ketone derivative with a 2-substituted alkanoic acid under basic conditions and thereafter oxidizing the intermediate with subsequent hydrolysis.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: March 13, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Varadaraj Elango, Kenneth G. Davenport
  • Patent number: 4849530
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 18, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Gerhard Zol, Gerhard Pfarrhofer
  • Patent number: 4845264
    Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: July 4, 1989
    Assignee: Teijin Limited
    Inventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
  • Patent number: 4837342
    Abstract: A prostacyclin analogue having the formula: ##STR1## wherein R.sup.1 is --CO.sub.2 R.sup.5 (wherein R.sup.5 is a hydrogen atom, a straight chain or branched alkyl group having from 1 to 12 carbon atoms, an aralkyl group having from 7 to 12 carbon atoms, a cycloalkyl group having from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl group, or one equivalent of a cation), or --CONR.sup.6 R.sup.7 (wherein each of R.sup.6 and R.sup.7 is a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom, form a 5- or 6-membered substituted or unsubstituted hetero ring which may contain a hetero atom other than said nitrogen atom); A is --CH.sub.2 CH.sub.2 CH.sub.2 --, CH.sub.2 --O--CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --O--CH.sub.2 -- or --CH.dbd.CHCH.sub.2 CH.sub. 2 --; B is trans --CH.dbd.CH-- or --C.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: June 6, 1989
    Assignees: Sagami Chemical Research Center, Toa Eiyo Ltd.
    Inventors: Masakatsu Shibasaki, Atsuo Takahashi, Tuyoshi Aoki, Kentaro Kogi, Yozo Nishimiya, Takeshi Nara, Takashi Yamaguchi
  • Patent number: 4833247
    Abstract: A process for the production of 2-benzyl fatty acids and esters thereof corresponding to the following formula ##STR1## comprising reacting 2-fatty alkyl-4,4-dimethyl-2-oxazolines with benzaldehydes corresponding to the formula R.sup.2 --C.sub.6 H.sub.4 --CHO to form 2-(1-benzylidene)-fatty alkyl-4,4-dimethyl-2-oxazolines, catalytically hydrogenating the products of this reaction to the 2-(1-benzyl)-fatty alkyl-4,4-dimethyl oxazolines and converting the products thus formed by acid-catalyzed hydrolysis or solvolysis with an alcohol of the formula R.sup.5 OH into the 2-benzyl fatty acids or esters thereof. Amidosulfonic acid gives particularly high yields as catalyst for the reaction of the 2-fatty alkyl-4,4-dimethyl-2-oxazolines with the benzaldehydes.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: May 23, 1989
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventor: Horst-Juergen Krause
  • 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
  • Patent number: 4804777
    Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalky, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, silver and optionally antimony, and carbon to form the corresponding alkali metal ester and contacting the alkali metal with a mineral acid.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: February 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4803301
    Abstract: There is provided a process for producing an optically active 2-phenoxypropionic acid, which comprises allowing an optically active lactic ester represented by the following formula (I) to react with a phenol represented by the following formula (II) in the copresence of a reagent A and a reagent B defined below to form an optically active 2-phenoxypropionic ester represented by the following formula (III), and liberating an optically active 2-phenoxypropionic acid represented by the following formula (IV) from the optically active 2-phenoxypropionic ester: ##STR1## wherein R.sup.1 represents a group to form a monovalent ester, which can be eliminated from the compound (III) under weakly basic to acidic conditions and R.sup.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: February 7, 1989
    Assignee: Kirin Beer Kabushiki Kaisha
    Inventors: Masayuki Sakakibara, Yasushi Nii
  • Patent number: 4791224
    Abstract: Process for the preparation of an aryloxyacetic acid/hydroxyethyl ether by oxidation of aryloxyethanol of the formula: ##STR1## wherein R either individually or independently of one another represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, bismuth, and carbon in the presence of a phenol corresponding to the structure: ##STR2## wherein R is as described above and p is 0, 1 or 2, to form the corresponding alkali metal ester/hydroxyethyl ether after catalyst removal the alkali metal ester is contacted with a mineral acid.
    Type: Grant
    Filed: April 7, 1988
    Date of Patent: December 13, 1988
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4767784
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 30, 1988
    Inventors: Gerhard Zolss, Gerhard Pfarrhofer
  • Patent number: 4766220
    Abstract: The invention relates to the preparation of optically active aryloxyalkanoic acid derivatives of the formula ##STR1## in which Ar represents an optionally substituted phenyl, naphthyl, phenoxy or pyridyloxy radical, R represents a C.sub.1 -C.sub.4 -alkyl radical and A represents a --COOR.sub.1, ##STR2## or --CO--Z radical, Z being halogen. It consists in reacting an aqueous or aqueous-organic solution of an optically active alkali metal salt of a 2-halogeno-alkanoic acid with an aqueous solution of an alkali metal salt of the phenol of the formula Ar-OH at an elevated temperature under a pressure less than the vapor pressure of water at the chosen temperature.It permits the preparation of aryloxyalkanoic acid derivatives with a very high content of the isomer having the D configuration, which can be used as herbicides.
    Type: Grant
    Filed: July 30, 1985
    Date of Patent: August 23, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Gras
  • Patent number: 4764521
    Abstract: This invention provides novel compounds which are leukotriene antagonists, certain novel intermediates to the compounds, formulations of the compounds, and a method of using the compounds for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: May 7, 1986
    Date of Patent: August 16, 1988
    Assignee: Eli Lilly and Company
    Inventor: David K. Herron
  • Patent number: 4759931
    Abstract: Liquid iodophors are provided containing as surface-active agent a product of the formula RO--(C.sub.3 H.sub.6 O).sub.m --(C.sub.2 H.sub.4 O).sub.n --CH.sub.2 COOM, wherein RO is the residue of an alcohol of at least 8 carbon atoms or of an alkylphenol of at least 10 carbon atoms which is substantially free of olefinic unsaturation, m is a number having an average value of 0-10, n is a number having an average value of 2-20 and M is hydrogen or a monovalent cation. Preferably the iodophors contain at least 20% of iodine. The novel iodophors are prepared by dissolving at room temperature the desired amount of iodine in the surface-active agent.
    Type: Grant
    Filed: April 10, 1984
    Date of Patent: July 26, 1988
    Assignee: 501 Stamicarbon B.V.
    Inventor: Nicolaas A. I. van Paassen
  • Patent number: 4760172
    Abstract: A process for the preparation of optically active 2-(4-methoxyphenoxy)propionic acid of at least 75 percent enantiomeric excess of the desired optical isomer comprised of contacting 2-chloropropionic acid or a lower alkyl ester or an alkali metal salt thereof, having an optical purity greater than 85 percent of the opposite configuration, with from 3 to 10 molar equivalents of 4-methoxyphenol in an aqueous base.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: July 26, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jimmy J. Tai