Chalcogen Bonded Directly At 5-position Of The Oxazole Ring Patents (Class 548/228)
  • Patent number: 4523030
    Abstract: Substituted benzophenones of the formula ##STR1## in which Ph represents unsubstituted or substituted phenyl and R represents free, esterified or amidated carboxy, have anti-inflammatory and/or analgesic properties and can be used as active ingredients in medicaments. They are manufactured, for example, as follows:a compound or a mixture of compounds of the formula ##STR2## in which X.sub.1 and X.sub.2 together represent a group of the formula --C(.dbd.O)--O that is bonded via the carbonyl group to the radical Ph and X.sub.3 represents hydrogen, or one of the radicals X.sub.1 and X.sub.3 represents a group of the formula --C(.dbd.O)--Z, the other represents hydrogen and X.sub.2 represents a group R'O-- in which R' represents hydrogen or a hydroxy-protecting group, is subjected to acid treatment and the primary product is decomposed solvolytically.
    Type: Grant
    Filed: June 7, 1984
    Date of Patent: June 11, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Georges Haas, Andreas von Sprecher, Pier G. Ferrini
  • Patent number: 4508921
    Abstract: A process for preparing .alpha.-alkyl amino acids by enantioretentive .alpha.-alkylation of .alpha.-amino acids is described. The products are bioactive compounds including some useful as therapeutic agents.
    Type: Grant
    Filed: June 28, 1984
    Date of Patent: April 2, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Joseph S. Amato, Leonard M. Weinstock, Sandor Karady
  • Patent number: 4499101
    Abstract: The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. Two compounds of this invention are N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]thiourea and N,N'-bis[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-cyanoguanidine.
    Type: Grant
    Filed: February 4, 1983
    Date of Patent: February 12, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4492597
    Abstract: A compound of 1,5-disubstituted 1,2,4-triazole-3-carboxamide represented by the general formula; ##STR1## wherein R.sup.1 is alkyl of one to three carbon atoms, chloro, fluoro, iodo, trifluoromethyl or nitro, R.sup.2 is hydrogen, methyl or chloro, R.sup.3 is hydrogen or methyl is provided in the invention, which shows an excellent herbicidal activity.
    Type: Grant
    Filed: May 19, 1982
    Date of Patent: January 8, 1985
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Katsumichi Aoki, Yoichi Kanda, Keigo Satake, Hiroyasu Shinkawa
  • Patent number: 4485236
    Abstract: Azlactone-functional compounds, which are liquid above 20.degree. C., and their method of preparation from alkenyl azlactones and nucleophilic group-substituted compounds are disclosed. The azlactone-functional compounds of the invention cure in the presence of nucleophilic chain-extending or crosslinking agents to form linear or crosslinked polyamide resin systems.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: November 27, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
  • Patent number: 4465505
    Abstract: This invention relates to ortho-heterocyclic benzene sulfonylureas which are useful as herbicides and growth regulants.
    Type: Grant
    Filed: October 7, 1982
    Date of Patent: August 14, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Anthony D. Wolf
  • Patent number: 4414404
    Abstract: A process for preparing a racemic mixture of N-acyl-D,L-phenylalanine ester by reacting the azlactone of N-acyl-acetaminocinnamic acid with hydrogen at a hydrogen pressure of at least about 100 psig at a temperature within the approximate range of about 50.degree.-200.degree. C. in the presence of a nickel hydrogenation catalyst, a lower alkanol and an alkali metal or an alkaline earth metal alkoxide.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: November 8, 1983
    Assignee: Ethyl Corporation
    Inventor: Jerry M. Roper
  • Patent number: 4388326
    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: May 7, 1980
    Date of Patent: June 14, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4388475
    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: May 7, 1980
    Date of Patent: June 14, 1983
    Assignee: Merck & Co., Inc.
    Inventor: Raymond A. Firestone
  • Patent number: 4378357
    Abstract: This invention relates to novel heterocyclic fungicides which are effective in controlling a broad spectrum of phytopathogenic fungi found in the four main classes of fungi namely Phycomycetes, Ascomycetes, Fungi Imperfecti, and Basidiomycetes. Certain of these compounds are especially effective in controlling sclerotial forming fungi such as Whetzelinia sclerotiorum=(Sclerotinia sclerotiorium) and Botrytis cinerea.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: March 29, 1983
    Assignee: Rohm and Haas Company
    Inventors: George A. Miller, Lendon N. Pridgen
  • Patent number: 4375472
    Abstract: Amidinosulphonic acid derivatives carrying an unsaturated nitrogen heterocycle-containing substituent, representative of which are N-methyl-N'[2-(5-methyl-4-imidazolylmethylthio)- ethyl] amidinosulphonic acid and N-methyl-N'-[2-(3-chloropyrid-2-ylmethylthio) ethyl] amidinosulphonic acid, are histamine H.sub.2 -receptor antagonists.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: March 1, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Rodney C. Young, Zev Tashma
  • Patent number: 4372963
    Abstract: Bisamidines carrying one unsaturated nitrogen heterocyclo-containing substituent, representative of which i; 1-[N'-(2-(5-methyl-4-imidazolyl)methylthio)ethyl)guanidino]-8-[N'-methylgu anidino]octane, are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: March 27, 1981
    Date of Patent: February 8, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4365066
    Abstract: Oxazoleacetic acid derivatives of the formula ##STR1## and salts thereof wherein R.sup.1 is a higher alkyl group having 10 to 20 carbon atoms, a higher alkenyl group, a benzyl group or a halogen substituted benzyl group; X is O, S or NH; R.sup.2 is a lower alkyl group, a phenyl group or a halogen-substituted phenyl group and R.sup.3 is a hydrogen atom or a lower alkyl group, having a hypolipidemic activity.
    Type: Grant
    Filed: July 28, 1981
    Date of Patent: December 21, 1982
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Tsutomu Yamanaka, Mitsuharu Sano, Hiroshi Yasuda
  • Patent number: 4355033
    Abstract: 2-Imino-imidazolidine derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as hereinafter set forth, and pharmaceutically acceptable acid addition salts thereof, are described. The 2-imino-imidazolidine derivatives are useful in the treatment of hypertension.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: October 19, 1982
    Assignee: Hoffman-La Roche Inc.
    Inventor: Henri Ramuz
  • Patent number: 4350628
    Abstract: A preparation of azlactones represented by the formula ##STR1## wherein R is a substituted or unsubstituted alkyl, aryl or nitrogen containing heterocyclic group, and R.sup.1 is an N-blocked amino acid residue or peptide chain, and stereoisomers thereof, by oxidizing the corresponding saturated azlactone with a benzoquinone oxidizing agent in the presence of a base is disclosed. The unsaturated azlactones, some of which are novel, can be converted to dehydro peptides, which are useful as intermediates for preparing novel biologically active compounds, or themselves have biological activity.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: September 21, 1982
    Assignee: Research Corporation
    Inventor: Charles H. Stammer
  • Patent number: 4339589
    Abstract: Manufacture of 4-substituted oxazolinone-(5) compounds, which are intermediates for substituted aminoacids, by alkylation of 2-substituted or 3,4-disubstituted oxazolinone-(5) compounds in an aprotic solvent in the presence of a tertiary amine.
    Type: Grant
    Filed: August 5, 1980
    Date of Patent: July 13, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
  • Patent number: 4304780
    Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof,in which Y represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl;R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: December 8, 1981
    Assignee: Glaxo Group Limited
    Inventors: Michael Martin-Smith, Barry Price, John Bradshaw, John W. Clitherow
  • Patent number: 4293691
    Abstract: A method for preparing image-forming color couplers containing a thioether group at the coupling active position is disclosed which comprises reacting a compound of the formula A-H where A is a cyan, magenta or yellow coupler residue in which a hydrogen atom at the coupling off position is removed with a disulfide of the formula (IIa) or (IIb): ##STR1## where R is a straight chain, branched chain or cyclic alkyl group, a cyclic alkenyl group, or an aralkyl group or a ##STR2## group, B is Y, -D-Y or ##STR3## where D is an oxygen atom or >N--R.sub.4, R.sub.4 is a hydrogen atom, an alkyl group or an aryl group, Y is a straight chain, branched chain or cyclic alkyl group, a straight chain, branched chain or cyclic alkenyl group, an aralkyl group, an aryl group, or a heterocyclic group, Q is a non-metallic atomic group necessary for completing a 5- or 6-membered nitrogen-containing heterocyclic group and R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: August 10, 1979
    Date of Patent: October 6, 1981
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuo Furutachi, Nobuo Seto
  • Patent number: 4267340
    Abstract: An oxoazetidine derivative compound of the formula: ##STR1## wherein R.sub.1 represents a substituted or unsubstituted amino radical and R.sub.3 represents a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and --SR.sub.2 is a residue of a thiophilic sulphur nucleophile.
    Type: Grant
    Filed: November 16, 1977
    Date of Patent: May 12, 1981
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takashi Kamiya, Yoshihisa Saito, Tsutomu Teraji, Osamu Nakaguti, Teruo Oku, Hitoshi Nakamura, Masashi Hashimoto
  • Patent number: 4264771
    Abstract: Manufacture of 4-substituted oxazolinone-(5) compounds, which are intermediates for .alpha.-substituted aminoacids, by alkylation of 2-substituted or 3,4-disubstituted oxozolinone-(5) compounds in an aprotic solvent in the presence of a tertiary amine.
    Type: Grant
    Filed: March 29, 1978
    Date of Patent: April 28, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
  • Patent number: 4257780
    Abstract: Described are fuel compositions containing oxazolonium hydroxides as detergent and corrosion inhibitor additives.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: March 24, 1981
    Assignee: Texaco Inc.
    Inventors: Rodney L. Sung, Peter Dorn
  • Patent number: 4251665
    Abstract: Amino resins, e.g., urea-formaldehyde and melamine-formaldehyde thermosetting resin systems, are cured with thermally-decomposable adducts of aromatic sulfonic acids and oxa-azacyclopentanes. The resin products cured with these adducts provide surface coatings having superior water resistance properties. The cured compositions can include other conventional ingredients capable of co-reacting with the amino resins, such as polyols, polyacids, alkyd resins, polyester resins, epoxies, acrylics and the like, to provide compositions curable to products having a wide range of properties.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: February 17, 1981
    Assignee: King Industries, Inc.
    Inventor: Leonard J. Calbo
  • Patent number: 4244969
    Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.
    Type: Grant
    Filed: February 13, 1975
    Date of Patent: January 13, 1981
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
  • Patent number: 4230865
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: October 28, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4228291
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: October 14, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Genellin
  • Patent number: 4221584
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R.sup.5 and R.sup.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Stephen D. Ziman
  • Patent number: 4216008
    Abstract: The present invention is directed to compounds of the formula ##STR1## wherein R.sub.1 is lower alkyl and R.sub.2 is lower alkyl or aryl. Also provided are methods for preparation of these compounds. The compounds of formula I above are useful as plant growth regulants.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: August 5, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Manfred Weigele, Dennis D. Keith
  • Patent number: 4197305
    Abstract: The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitrometylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)ethyl)isothiour eido]propane. The compounds of this invention are inhibitors of H-2 histamine receptors.
    Type: Grant
    Filed: September 11, 1978
    Date of Patent: April 8, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4176121
    Abstract: Compounds having the formula ##STR1## in which R is phenyl, phenylthio, phenoxy, or lower aklylthio; R.sub.1 is lower alkoxy; R.sub.2 is lower alkyl or lower alkoxy; R.sub.3 is lower alkyl; and X is sulfur or oxygen. The compounds have utility as insecticides and miticides.The compounds can be prepared through novel intermediates having the formula ##STR2## by a novel process of reacting a methyl ketone oxime with a haloacetyl chloride in the absence of an acid acceptor.
    Type: Grant
    Filed: October 25, 1978
    Date of Patent: November 27, 1979
    Assignee: Stauffer Chemical Company
    Inventor: Arnold D. Gutman
  • Patent number: 4175130
    Abstract: Oxazole- and thiazole-alkanoic acid compounds useful as drugs for the treatment of atherosclerosis with lipid metabolism disorder, and having the formula: ##STR1## wherein R is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aralkyl group, a pyridylmethyl group or a tocopheryl group; each of R.sup.1 and R.sup.2 is a hydrogen atom or a halogen atom; R.sup.3 is a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.4 is a hydrogen atom, a halogen atom, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a trifuloromethyl group; each of X and Y is an oxygen atom or a sulfur atom; and A is a straight or branched alkylene group having 1 to 4 carbon atoms, and pharmaceutically acceptable salts thereof are disclosed.
    Type: Grant
    Filed: March 22, 1978
    Date of Patent: November 20, 1979
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tsutomu Yamanaka, Hiroshi Yasuda, Kunio Osuga
  • Patent number: 4174443
    Abstract: Novel aza-bis-lactams having the formula: ##STR1## wherein n is an integer from 1 to 3; p is 0 or 1; R.sup.2 and R.sup.4 are independently hydrogen, alkyl having from 1 to 4 carbon atoms, or phenyl; X is methylene, an oxygen atom or --N<.sup.R.spsp.2 ; Y is methylene or, when X is methylene, then Y can also be --N<.sup.R.spsp.2 ; and R, R.sup.1 and R.sup.3 are independently alkylene having from 2 to 6 carbon atoms.
    Type: Grant
    Filed: December 30, 1977
    Date of Patent: November 13, 1979
    Assignee: GAF Corporation
    Inventor: Philip B. Dalton
  • Patent number: 4168379
    Abstract: New pyridin-3-ols and their N-oxides and acid addition salts, which are useful as intermediates, especially for the preparation of pharmacologically active compounds, and their preparation.
    Type: Grant
    Filed: March 10, 1978
    Date of Patent: September 18, 1979
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter Boell, Horst Koenig