Chalcogen Bonded Directly At 5-position Of The Oxazole Ring Patents (Class 548/228)
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Patent number: 4523030Abstract: 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: GrantFiled: June 7, 1984Date of Patent: June 11, 1985Assignee: Ciba-Geigy CorporationInventors: Georges Haas, Andreas von Sprecher, Pier G. Ferrini
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Patent number: 4508921Abstract: 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: GrantFiled: June 28, 1984Date of Patent: April 2, 1985Assignee: Merck & Co., Inc.Inventors: Joseph S. Amato, Leonard M. Weinstock, Sandor Karady
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Patent number: 4499101Abstract: 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: GrantFiled: February 4, 1983Date of Patent: February 12, 1985Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin
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Patent number: 4492597Abstract: 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: GrantFiled: May 19, 1982Date of Patent: January 8, 1985Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Katsumichi Aoki, Yoichi Kanda, Keigo Satake, Hiroyasu Shinkawa
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Patent number: 4485236Abstract: 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: GrantFiled: September 27, 1982Date of Patent: November 27, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
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Patent number: 4465505Abstract: This invention relates to ortho-heterocyclic benzene sulfonylureas which are useful as herbicides and growth regulants.Type: GrantFiled: October 7, 1982Date of Patent: August 14, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Anthony D. Wolf
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Patent number: 4414404Abstract: 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: GrantFiled: March 11, 1982Date of Patent: November 8, 1983Assignee: Ethyl CorporationInventor: Jerry M. Roper
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Patent number: 4388326Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: May 7, 1980Date of Patent: June 14, 1983Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4388475Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: May 7, 1980Date of Patent: June 14, 1983Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4378357Abstract: 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: GrantFiled: December 16, 1977Date of Patent: March 29, 1983Assignee: Rohm and Haas CompanyInventors: George A. Miller, Lendon N. Pridgen
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Patent number: 4375472Abstract: 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: GrantFiled: November 24, 1980Date of Patent: March 1, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Rodney C. Young, Zev Tashma
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Patent number: 4372963Abstract: 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: GrantFiled: March 27, 1981Date of Patent: February 8, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Peter D. Miles
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Patent number: 4365066Abstract: 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: GrantFiled: July 28, 1981Date of Patent: December 21, 1982Assignee: Yoshitomi Pharmaceutical Industries Ltd.Inventors: Tsutomu Yamanaka, Mitsuharu Sano, Hiroshi Yasuda
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Patent number: 4355033Abstract: 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: GrantFiled: August 14, 1980Date of Patent: October 19, 1982Assignee: Hoffman-La Roche Inc.Inventor: Henri Ramuz
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Patent number: 4350628Abstract: 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: GrantFiled: March 24, 1981Date of Patent: September 21, 1982Assignee: Research CorporationInventor: Charles H. Stammer
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Patent number: 4339589Abstract: 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: GrantFiled: August 5, 1980Date of Patent: July 13, 1982Assignee: BASF AktiengesellschaftInventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
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Patent number: 4304780Abstract: 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: GrantFiled: June 6, 1980Date of Patent: December 8, 1981Assignee: Glaxo Group LimitedInventors: Michael Martin-Smith, Barry Price, John Bradshaw, John W. Clitherow
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Patent number: 4293691Abstract: 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: GrantFiled: August 10, 1979Date of Patent: October 6, 1981Assignee: Fuji Photo Film Co., Ltd.Inventors: Nobuo Furutachi, Nobuo Seto
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Patent number: 4267340Abstract: 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: GrantFiled: November 16, 1977Date of Patent: May 12, 1981Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Yoshihisa Saito, Tsutomu Teraji, Osamu Nakaguti, Teruo Oku, Hitoshi Nakamura, Masashi Hashimoto
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Patent number: 4264771Abstract: 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: GrantFiled: March 29, 1978Date of Patent: April 28, 1981Assignee: BASF AktiengesellschaftInventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
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Patent number: 4257780Abstract: Described are fuel compositions containing oxazolonium hydroxides as detergent and corrosion inhibitor additives.Type: GrantFiled: December 10, 1979Date of Patent: March 24, 1981Assignee: Texaco Inc.Inventors: Rodney L. Sung, Peter Dorn
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Patent number: 4251665Abstract: 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: GrantFiled: October 5, 1979Date of Patent: February 17, 1981Assignee: King Industries, Inc.Inventor: Leonard J. Calbo
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Patent number: 4244969Abstract: 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: GrantFiled: February 13, 1975Date of Patent: January 13, 1981Assignee: Aktiebolaget HassleInventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
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Patent number: 4230865Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.Type: GrantFiled: September 8, 1978Date of Patent: October 28, 1980Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
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Patent number: 4228291Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.Type: GrantFiled: October 4, 1978Date of Patent: October 14, 1980Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, John C. Emmett, Charon R. Genellin
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Patent number: 4221584Abstract: 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: GrantFiled: February 9, 1979Date of Patent: September 9, 1980Assignee: Chevron Research CompanyInventor: Stephen D. Ziman
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Patent number: 4216008Abstract: 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: GrantFiled: May 22, 1978Date of Patent: August 5, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Manfred Weigele, Dennis D. Keith
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Patent number: 4197305Abstract: 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: GrantFiled: September 11, 1978Date of Patent: April 8, 1980Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin
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Patent number: 4176121Abstract: 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: GrantFiled: October 25, 1978Date of Patent: November 27, 1979Assignee: Stauffer Chemical CompanyInventor: Arnold D. Gutman
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Patent number: 4175130Abstract: 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: GrantFiled: March 22, 1978Date of Patent: November 20, 1979Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Tsutomu Yamanaka, Hiroshi Yasuda, Kunio Osuga
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Patent number: 4174443Abstract: 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: GrantFiled: December 30, 1977Date of Patent: November 13, 1979Assignee: GAF CorporationInventor: Philip B. Dalton
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Patent number: 4168379Abstract: 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: GrantFiled: March 10, 1978Date of Patent: September 18, 1979Assignee: BASF AktiengesellschaftInventors: Walter Boell, Horst Koenig