Sulfoxy Patents (Class 562/429)
  • Patent number: 4990660
    Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.
    Type: Grant
    Filed: December 21, 1988
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4985585
    Abstract: Phenoxyalkylcarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1 indicates hydrogen atom, methyl group or ethyl group, m is an integer from 2 to 5, and n is an integer from 3 to 8, X.sup.1 and X.sup.2 each independently represent sulfur atom, oxygen atom, sulfinyl group or sulfonyl group, proviso X.sup.1 and X.sup.2 are not simultaneously oxygen atom; their alkali salts and hydrates thereof are useful as antiallergic agents.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: January 15, 1991
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Mitsuo Ohashi, Katsuya Awano, Toshio Tanaka, Tetsuya Kimura
  • Patent number: 4980499
    Abstract: Compounds are described of formula (1) ##STR1## in which n is 1 or 2;M is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --, or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, C.sub.1-6 alkyl or C.sub.7-10 phenalkyl,Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl,and their salts.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: December 25, 1990
    Assignee: Glaxo Group Limited
    Inventor: Eric W. Collington
  • Patent number: 4966731
    Abstract: There is disclosed a process for preparing sulfonyl acids from mercaptans in a single reactor. The mercaptan is converted to mercaptide and reacted with a lactone or lactam in an organic solvent which is removed after formation of a thioether containing acid. Water is provided as a solvent for the oxidation of the thioether to the sulfone. Mild conditions and readily available starting materials render the method capable of preparing such acids in large scale amounts.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: October 30, 1990
    Assignee: Monsanto Company
    Inventor: Yueting Chou
  • Patent number: 4963578
    Abstract: There are described compounds of formula ##STR1## in which n is 0, 1 or 2, R.sup.1 is a hydrocarbyl group optionally substituted with an optionally substituted phenyl group and containing from 5 to 30 carbon atoms, R.sup.2 is optionally substituted phenyl or C.sub.1-10 alkyl optionally substituted by one or more substituents selected from optionally protected hydroxyl, optionally protected carboxyl, nitrile, optionally protected tetrazolyl, --COR.sup.6 where R.sup.6 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.7 where each R.sup.7 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.8 where R.sup.8 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.9 where R.sup.9 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and R.sup.3, R.sup.4 and R.sup.5 are each selected from hydrogen, carboxyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkyl, C.sub.
    Type: Grant
    Filed: November 1, 1989
    Date of Patent: October 16, 1990
    Assignee: Lilly Industries Limited
    Inventors: Stephen R. Baker, William B. Jamieson, deceased, Alec Todd
  • Patent number: 4959383
    Abstract: Phenylsulfone alkenoic acids and derivatives thereof are provided which have the structure ##STR1## wherein Ar represents an aryl group including phenyl or naphthyl which may or may not include one or more substituents, X is COOR wherein R is hydrogen, alkali metal or lower alkyl or X is 5-tetrazolyl or ##STR2## wherein R' is lower alkyl or aryl; n is 2, 3 or 4 and m is 2, 3 or 4. These compounds are cardiovascular agents which exhibit thromboxane antagonist activity and thus are useful in the treatment of thrombotic and vasospastic disease.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: September 25, 1990
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Steven E. Hall
  • 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: 4954165
    Abstract: An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2 is discosed.In addition, the herbicidally effective benzoyl derivative having the formula: ##STR2## wherein: X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2;L is C.sub.1 -C.sub.4 alkylene is disclosed.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
  • Patent number: 4943310
    Abstract: The invention relates to new 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexenecarboxylic acid derivatives of general formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.2 and R.sup.3 have the meanings given in the description, and their use as plant growth regulants.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: July 24, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Alfred Angermann, Helga Franke, Gerhard Johann
  • 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: 4914231
    Abstract: Disclosed is a method for purifying a crude diphenylsulfone tetracarboxylic acid which comprises the steps of dissolving a crude diphenyolsulfone tetracarboxylic acid in a solvent mixture of water and acetic acid and recrystallizing the crude to obtain a highly purifed diphenylsulfone tetracarboxylic acid.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: April 3, 1990
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Hiroshi Manami, Shigeo Miki, Mikio Nakazawa
  • Patent number: 4910282
    Abstract: There is provided an aromatic polyamide having repeating units of the formula: ##STR1## wherein X is -O-, -S-, -CO- or -SO.sub.2 - and y has a value of 1 or 2. Also provided is an aromatic polyamide having repeating units of the formula: ##STR2## and a new composition of matter 3-[4-(3-aminophenoxy benzoyl)phenoxy] benzoic acid.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: March 20, 1990
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Tonson Abraham, Robert C. Evers, Edward J. Soloski
  • Patent number: 4906658
    Abstract: Compounds of Formula I ##STR1## the pharmaceutically acceptable salts, and the gamma-lactone form thereof are described. They are antagonists of leukotrienes and SRS-A.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: March 6, 1990
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Haydn W. R. Williams, Robert N. Young
  • Patent number: 4898973
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: February 6, 1990
    Assignee: ICI Americas Inc.
    Inventor: David L. Lee
  • Patent number: 4883887
    Abstract: A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.
    Type: Grant
    Filed: July 1, 1988
    Date of Patent: November 28, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
  • Patent number: 4874777
    Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: April 10, 1987
    Date of Patent: October 17, 1989
    Assignee: Eli Lilly and Company
    Inventors: F. Patrick Carr, Robert D. Dillard, Doris E. McCullough
  • Patent number: 4874792
    Abstract: This invention relates to alkanoic acid compounds having phenyl and thio substituents which are useful as leukotriene antagonists and pharmaceutical compositions containing such compounds. This invention also relates to treating diseases in which leukotrienes are a factor by administration of an effective amount of the above compounds or compositions.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: October 17, 1989
    Assignee: Smithkline Beckman Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Thomas W. Ku, Carl D. Perchonock
  • Patent number: 4871756
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
  • Patent number: 4857659
    Abstract: The present invention relates to a stereo-selective synthesis of leukotriene antagonists. More particularly, this invention relates to the stereo-selective synthesis of (.beta.S,.gamma.R) and (.beta.R,.gamma.S)-4-((3-(4-acetyl-3-hydroxy-2-propyl(phenoxy)propyl)-thio -.gamma.-hydroxy-.beta.-methylbenzenebutanoic acid, and related compounds. These compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular, disorders, inflammation and pain in mammals, especially humans. The compounds are also useful for inducing cytoprotection in mammals, especially humans.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: August 15, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Richard Frenette, Jacques-Yves Gauthier, Robert N. Young, Robert Zamboni, Masatoshi Kakushima, Thomas R. Verhoeven
  • 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: 4853398
    Abstract: This invention provides benzene derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: April 13, 1987
    Date of Patent: August 1, 1989
    Assignee: Eli Lilly and Company
    Inventors: F. P. Carr, Robert D. Dillard, Doris E. McCullough
  • Patent number: 4853403
    Abstract: A 3-phenylthiomethylstyrene derivative having the general formula (1): ##STR1## or salt thereof with a base, when X is hydroxyl group, R.sup.1 is hydrogen atom or R.sup.2 is hydrogen atom, a process for preparing the 3-phenylthiomethylstyrene derivative (1), and an antiallergic agent and a tyrosinekinase inhibiting agent containing the 3-phenylthiomethylstyrene derivative (1) as an effective component. The compound (1) of the present invention is a useful intermediate for preparing various organic compounds, and has excellent antiallergic and tyrosinekinase inhibiting activities.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: August 1, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Tadayoshi Shiraishi, Naohiro Imai, Takeshi Domoto, Keiji Kameyama, Ikuo Katsumi, Takayoshi Hidaka, Kazunori Hosoe, Kiyoshi Watanabe
  • 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: 4837363
    Abstract: Compounds are described of formula (1) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 CH.sub.2 --, or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, C.sub.1-6 alkyl or C.sub.7-10 phenalkyl,Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl,and their salts.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.
    Type: Grant
    Filed: April 23, 1985
    Date of Patent: June 6, 1989
    Assignee: Glaxo Group Limited
    Inventor: Eric W. Collington
  • Patent number: 4824993
    Abstract: Compounds are described of formula (I) ##STR1## in which n is 1 or 2;m is 2-5 and X is --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; or m is 1-4 and X is --CH.dbd.C.dbd.CH--;R.sup.1 is --H, alkyl, phenalkyl, phenyl, substituted phenyl or naphthyl;Y substituted or unsubstituted 3-phenoxy-2-hydroxypropyl.These compounds inhibit gastric acid secretion and provide gastrointestinal cytoprotection, and may be formulated for use in the treatment of ulcers.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: April 25, 1989
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Harry Finch, Duncan B. Judd
  • Patent number: 4820719
    Abstract: This invention relates to alkanoic acid compounds having phenyl and thio substituents which are useful as leukotriene antagonists and pharmaceutical compositions containing such compounds. This invention also relates to methods of treating diseases in which leukotrienes are a factor by administration of an effective amount of the above compounds or compositions.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: April 11, 1989
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Ralph F. Hall, Thomas Wen-Fu Ku, Carl D. Perchonock
  • Patent number: 4814166
    Abstract: Anionic oligomers of the general formula: ##STR1## in which T denotes the radical ##STR2## optionally in a mixture with the OH radical; u=0 or 1; p=1 or 2; M=H, Na, K, ammonium or a mono-, di- or tri-(alkyl or hydroxyalkyl)ammonium group, the alkyl part containing 1 to 4 carbon atoms; n=5-30; z=1-6; and R denotes an aliphatic, alicyclic, aryl, alkylaryl or aralkyl radical of valency z, which can contain 1 or more oxygen atoms, it being possible for the formula (I) to contain minor proportions of intermolecular or intra-molecular branches originating from a bis-epoxide.These oligomers are prepared by the addition of n mols of epihalogenohydrin, and optionally of a minor proportions of bis-epoxide, to 1 mol of compoundsR(OH).sub.z (II),in the presence of a Lewis acid, the polyhalogen compounds obtained then being converted into polythiocarboxylic compounds by reaction with a salt or an ester of thiloactic acid, thioglycolic acid or .alpha.-mercaptopropionic or .beta.
    Type: Grant
    Filed: May 20, 1986
    Date of Patent: March 21, 1989
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Henri Sebag
  • Patent number: 4778804
    Abstract: New nitro aliphatic compounds and their pharmaceutically acceptable salts are disclosed.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: October 18, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masanori Okamoto, Morita Iwami, Shigehiro Takase, Itsuo Uchida, Kazuyoshi Umehara, Masanobu Kohsaka, Hiroshi Imanaka
  • Patent number: 4760067
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: July 26, 1988
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4755524
    Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R.sub.3 represents CO.sub.2 H, CO.sub.2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: January 15, 1987
    Date of Patent: July 5, 1988
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis, James R. Deason
  • Patent number: 4752616
    Abstract: Arylthioalkylphenylcarboxylic acids are provided which have the structure ##STR1## wherein Ar represents an aryl group including phenyl or naphthyl which may or may not include one or more substituents, A is ##STR2## R is hydrogen, alkali metal or lower alkyl, m is 0, 1, 2, or 3, n is 0, 1, or 2, p is 1 to 5, q, is 0, 1, 2, or 3, r is 0, 1, 2, or 3. These compounds are cardiovascular agents which exhibit thromboxane antagonist activity and thus are useful in the treatment of thrombotic disease.
    Type: Grant
    Filed: June 29, 1987
    Date of Patent: June 21, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Steven E. Hall, Philip D. Stein
  • Patent number: 4748271
    Abstract: A process is described for the preparation of cis-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-indene-3-acetic acid that consists in reacting a lower alkyl ester of 5-fluoro-2-methylindene-3-acetic acid with a substantially equimolecular amount of 4-methylthio-benzaldehyde in a solid-liquid two-phase system in which the solid phase is a potassium alcoholate or hydroxide and the liquid phase is a solution of the reagents in an organic solvent inert in the reaction conditions, in the presence of a phase transfer catalyst and at a temperature comprised between -20.degree. and +20.degree. C.
    Type: Grant
    Filed: June 17, 1986
    Date of Patent: May 31, 1988
    Assignee: Zambon S.p.A.
    Inventor: Mariano Meneghin
  • Patent number: 4744812
    Abstract: Substituted diphenyl ethers of the formula ##STR1## where Z.sub.1, Z.sub.2 and Z.sub.3 are hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, Z.sub.4 is hydrogen, cyano, alkyl, alkoxy, acetoxy or alkylmercapto, Y is hydrogen, halogen, cyano or nitro, X is oxygen, sulfur, sulfinyl or sulfonyl, and A is hydrogen, unsubstituted or substituted alkyl ##STR2## and can also be sulfonyl ##STR3## when X is oxygen, and, when Z.sub.4 is alkoxy or alkylmercapto, can also be a methylene chain --(CH.sub.2).sub.m -- by which the radicals Z.sub.4 --CH--X-- are bonded to form a ring, R.sub.1 is hydrogen, methyl, ethyl or n-propyl, R.sub.2 is cyano, methoxy, ethoxy or ##STR4## where B is OH, ONa, O--alkyl, unsubstituted or substituted phenoxy, --NH.sub.2, --NH--alkyl or --N(alkyl).sub.2, n is 1, 2 or 3, R.sub.3 and R.sub.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
  • Patent number: 4730005
    Abstract: The compounds represented by the following structural formula (I) ##STR1## wherein m is 1 or 2; n is 1, 2 or 3; R' is hydrogen or methyl; R is a radical selected from the group consisting of: ##STR2## wherein R.sub.1 is C.sub.8 to C.sub.13 alkyl, C.sub.7 to C.sub.12 alkoxy, C.sub.7 to C.sub.12 thioalkyl, C.sub.10 to C.sub.12 1-alkynyl, 11-dodecynyl, 1-trans-dodecenyl, 5-(4-acetyl-3-hydroxy-2-propylphenoxypentoxy, 2(Z), 5(Z)-undecadienyloxy, phenyl-C.sub.4 to C.sub.10 alkyl with the phenyl optionally mono substituted with bromo, chloro, trifluoromethyl, methoxy, methylthio or trifluoromethylthio, phenylthio-C.sub.3 to C.sub.9 alkyl with the phenyl optionally mono substituted with bromo, chloro, trifluoromethyl, methoxy, methylthio or trifluoromethylthio, phenyl-CH.dbd.CH--(CH.sub.2).sub.2-8, phenyl-C.sub.3 to C.sub.9 alkoxy, trifluoromethyl-C.sub.7 to C.sub.12 alkyl, cyclohexyl- C.sub.4 to C.sub.10 alkyl or ##STR3## wherein each q is 0, 1, 2 or 3 but the sum of both q's does not exceed 3, and R.sub.
    Type: Grant
    Filed: May 16, 1986
    Date of Patent: March 8, 1988
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Carl D. Perchonock
  • Patent number: 4723016
    Abstract: One-step process for preparing anhydrous, organic acid alkali or alkaline earth metal salts by contacting and reacting an organic or polymeric acid fluoride, anhydride or ester and an organic alkali or alkaline earth metal silanolate.
    Type: Grant
    Filed: February 13, 1986
    Date of Patent: February 2, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Bertrand L. Chenard, Evan D. Laganis
  • Patent number: 4720505
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: November 13, 1984
    Date of Patent: January 19, 1988
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Patrice C. Belanger, John W. Gillard, Joshua Rokach
  • Patent number: 4711903
    Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different and independently represent tert-alkyl or phenyl; A represents methylene or methylene substituted by alkyl, dialkyl or hydroxy, provided that when A includes hydroxymethylene, the hydroxymethylene group is not adjacent to a heteroatom; B represents sulfur, sulfoxide, sulfone, oxygen, --NH-- or nitrogen substituted by alkyl, phenyl, benzyl, substituted phenyl or substituted benzyl; C represents methylene or methylene substituted by alkyl; R.sub.3 represents CO.sub.2 H, CO.sub.2 -alkyl or a tetrazole group; m is 0 or 1, n is 2, 3 or 4 and p is 1, 2 or 3; amd the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: January 31, 1986
    Date of Patent: December 8, 1987
    Assignee: G. D. Searle & Co.
    Inventors: Richard A. Mueller, Richard A. Partis, James R. Deason
  • Patent number: 4698364
    Abstract: Benzoic acid derivatives of the formula: ##STR1## wherein n is an integer of 0 to 2; R.sub.1 to R.sub.3 which may be the same or different each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or nitro group; R.sub.4 is a hydroxyl group or the group --NHZ (Z is hydrogen atom or a lower alkyl group), or an alkali metal salts thereof are useful as an infection control agent.These derivatives excepting compounds of the formula above wherein n is 0 or 1; any one of R.sub.1 to R.sub.3 is 5-chloro, 5-methoxy or 5-nitro and the remainder is a hydrogen atom; and R.sub.4 is a hydroxyl group; and compounds of the formula wherein n is 0 or 1; two of R.sub.1 to R.sub.3 are 3,5-dichloro or 3,5-dinitro and the remainder is a hydrogen atom; and R.sub.4 is a hydroxy group) are novel, and they were first prepared in this invention.
    Type: Grant
    Filed: October 18, 1985
    Date of Patent: October 6, 1987
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Mitsuru Tanemura, Isao Matsunaga, Masami Saitou
  • Patent number: 4697037
    Abstract: The preparation of dibenzo[b,f]thiepin compounds by a process comprising the direct carboxylation of an ortho-toluyl-aryl sulfide to introduce a phenylacetic acid side chain is disclosed.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: September 29, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Thomas R. Verhoeven
  • Patent number: 4686235
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: August 11, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
  • Patent number: 4684744
    Abstract: Stilbene derivatives of the formula ##STR1## wherein X is chlorine or bromine, R.sub.1 is hydrogen, carboxyl, cyano, C.sub.1 -C.sub.6 -alkyl or a non-chromophorically esterified carboxyl group, and R.sub.2 and R.sub.3 independently of one another are each hydrogen, unsubstituted or non-chromophorically substituted C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.4 -alkenyl, or a non-chromophoric substituent of the 2nd order.They are valuable intermediates for producing optical brighteners of the 4,4'-disubstituted stilbene series.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: August 4, 1987
    Assignee: Ciga-Geiby Corporation
    Inventors: Klaus Artz, Hans R. Meyer, Dieter Reinehr, Kurt Weber
  • Patent number: 4678665
    Abstract: Products of formula (I) ##STR1## in which R=C.sub.6-18 aromatic or alkylaromatic of valency z, R'=H, C.sub.1-16 alkyl or phenyl, A=CH.sub.2 or CH.sub.2 --O-- and, in the latter case, R'.noteq.H, x=1-8, y=1-20, z=1-3 and T denotes one or more anionic groups or a mixture of anionic groups and non-ionic groups are disclosed.These compounds are prepared by the reaction of a phenol R(OH).sub.z with an epoxide ##STR2## and an epihalogenohydrin ##STR3## in which X=Cl or Br, this being followed by replacement of X with one or more hydrophilic groupsThese compounds can be used as surface-active agents.
    Type: Grant
    Filed: August 2, 1984
    Date of Patent: July 7, 1987
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Henri Sebag
  • Patent number: 4673690
    Abstract: The acylated enamide compounds are acylated enamides corresponding to the general formula ##STR1## in which Z represents an electron donor group,n is 1, 2 or 3, andR.sup.1 represents hydrogen, a halogen or any organic group,or salts, complexes, alkylated derivatives or acylated derivatives of these compounds.Typical acylated enamide compounds according to the invention correspond to the formula ##STR2## These acylated enamide compounds and the pharmaceutical compositions containing the compounds are useful in the prevention and treatment of cancers.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: June 16, 1987
    Assignee: Biotec
    Inventors: Marcel B. Roberfroid, Heinz G. Viehe, Francoise M. Hervens
  • Patent number: 4670470
    Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4668509
    Abstract: Polythioalkanecarboxylic products of formula: ##STR1## in which R.sub.1 =C.sub.6-30 aromatic or alkylaromatic radical; R.sub.2 =C.sub.4 -C.sub.18 alkyl; A=C.sub.1-3 alkylene; M=H, alkali metal or alkaline earth metal, an ammonium ion or a substituted ammonium ion; z=1-6; m=1-10; n=1-20; and u=zero or 1 are disclosed.A process of preparation comprising, in a first stage, reacting an alcohol or phenol of formula R.sub.1 (OH) .sub.z (II) with an epihalogenohydrin of formula ##STR2## in which X=Cl or Br, in the presence of a Lewis acid, to give the intermediates of the formula: ##STR3## and in a second stage, the two compounds of formulae R.sub.2 SH (V) and HS--A--COOH (VI), in which R.sub.2 and A have the meanings indicated above, are reacted simultaneously or successively with the compound of the formula (IV) is also disclosed.The compounds of the formula (I) are used in cosmetic compositions.
    Type: Grant
    Filed: August 2, 1984
    Date of Patent: May 26, 1987
    Assignee: L'Oreal
    Inventors: Guy Vanlerberghe, Henri Sebag
  • Patent number: 4667055
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: May 19, 1987
    Assignee: Merck Frosst Canada, Inc.
    Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger
  • Patent number: 4661515
    Abstract: Novel compounds possessing both angiotensin enzyme inhibitory activity and diuretic activity are disclosed. The compounds are represented by the general formula ##STR1## in which X is ##STR2## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, and cycloalkyl, and may be the same or different; n is an integer from 0 to 4 inclusive; M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cyloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, or M and R.sub.6 taken together with the nitrogen to which M is bonded and the carbon to which R.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: April 28, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John J. Piwinski
  • Patent number: 4652303
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: March 24, 1987
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4643994
    Abstract: This invention relates to novel organic trithio oxides of the formula:R.sup.1 --X --R--X.sup.1 --R.sup.1wherein R is selected from --CH.sub.2 CH.dbd.CH--, ##STR1## and (CH.sub.2).sub.3 ; X is selected from ##STR2## X.sup.1 is selected from --S--S, ##STR3## and, each R.sup.1 is independently selected from carboxyalkyl, alkoxy, alkylthio, amino, alkylamino and acyl substituted and unsubstituted lower alkyl, lower alkenyl, lower alkynyl, phenyl and lower alkylphenyl; provided when R is --CH.sub.2 CH.dbd.CH--, X is ##STR4## and X.sup.1 is --S--S--, then R.sup.1 is not in both instances --CH.sub.2 CH.dbd.CH.sub.2.This invention also relates to a method of preparing the above-identified compounds by heating and further oxidizing various oxides of organic disulfides and to antithrombotic uses of the compounds.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: February 17, 1987
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Saleem Ahmad
  • Patent number: 4642372
    Abstract: A process for the preparation of cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein Z is selected from the group consisting of --CN, --COOH and --COOR.sub.1, R.sub.1 is alkyl of 1 to 6 carbon atoms and R.sub.2 and R.sub.3 are alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms comprising reacting at low temperatures in a solvent in the presence of a strong base a compound of the formula ##STR2## wherein Z has the above definitions and R is alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms with a sulfone of the formula ##STR3## wherein R.sub.2 and R.sub.3 have the above definitions and Y is an aromatic group followed by aqueous treatment to obtain a compound of the formula ##STR4## wherein Y, R, R.sub.2, R.sub.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: February 10, 1987
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute