Chalcogen Bonded Directly To The Oxazine Ring Patents (Class 544/97)
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Patent number: 4631276Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylamino-carbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.Type: GrantFiled: July 3, 1984Date of Patent: December 23, 1986Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
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Patent number: 4625028Abstract: This invention relates to selected hydrogenated 5,6-dihydro-6-aryluracils.Type: GrantFiled: July 11, 1983Date of Patent: November 25, 1986Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4595533Abstract: Esters of carbamic acids containing at least one hydrogen atom attached to the carbamic nitrogen atom are reacted with organic carbonates to produce esters of carbamic acids having a greater degree of organic substitution on the carbamic nitrogen atom than the reactant esters. Preferably, the reactant esters are alkylated using dialkyl carbonates.Type: GrantFiled: September 23, 1982Date of Patent: June 17, 1986Assignee: PPG Industries, Inc.Inventor: Ralph B. Thompson
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Patent number: 4585867Abstract: 1,2,3,4-Tetrahydro-4-quinolinones of the formula ##STR1## are prepared from a 3-anilinopropionic acid of general for formula ##STR2## which is treated successively with phosgene, with a base or by heating, and then with a Lewis acid or a strong acid. In the formulae (I) and (II), R denotes a hydrogen atom, a halogen atom, an alkyl radical (1 to 4 carbon atoms) or an alkoxy radical (1 to 4 carbon atoms), and R.sub.1 denotes a hydrogen atom or any alkyl radical (1 to 4 carbon atoms). The compounds of formula I are useful as intermediates in the production of known drugs.Type: GrantFiled: September 20, 1984Date of Patent: April 29, 1986Assignee: Rhone-Poulenc SanteInventors: Michel Arnaud, Jean-Pierre Corbet
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Patent number: 4578466Abstract: This invention relates to the use of 6-aryluracils as antiinflammatory and antiarthritic agents and also to both novel intermediates and novel processes for the preparation of selected 6-aryluracils.Type: GrantFiled: September 17, 1984Date of Patent: March 25, 1986Assignee: The Upjohn CompanyInventors: Harvey I. Skulnick, Herman W. Smith, Robert J. Smith, Wendell Wierenga
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Patent number: 4529544Abstract: Azetidines are prepared by decarboxylating a tetrahydro-1,3-oxazin-2-one.Type: GrantFiled: August 29, 1983Date of Patent: July 16, 1985Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4521599Abstract: This invention relates to the use of 6-aryluracils as antiinflammatory and antiarthritic agents and also to both novel intermediates and novel processes for the preparation of selected 6-aryluracils.Type: GrantFiled: September 17, 1984Date of Patent: June 4, 1985Assignee: The Upjohn CompanyInventors: Harvey I. Skulnick, Herman W. Smith, Robert J. Smith, Wendell Wierenga
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Patent number: 4495349Abstract: This invention relates to the use of 6-aryluracils as antiinflammatory and antiarthritic agents and also to both novel intermediates and novel processes for the preparation of selected 6-aryluracils.Type: GrantFiled: July 11, 1983Date of Patent: January 22, 1985Assignee: The Upjohn CompanyInventors: Harvey I. Skulnick, Herman W. Smith, Robert J. Smith, Wendell Wierenga
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Patent number: 4495355Abstract: A novel optically active diamide derivative represented by the following general formula is provided, which is useful as a starting material for asymmetric synthesis of optically active compounds, ##STR1## wherein R.sup.1 is an acyclic or cyclic, divalent atomic group containing at least one carbon atom which will, upon substitution of one of the heterocyclic groups in the formula with a nucleophilic reagent, stand as an asymmetric center in the substitution product; R.sup.2 is a substituent which has such a configuration and a molecular size that the regioselectivity in the substitution reaction of the heterocyclic group with the nucleophilic reagent can be determined by a stereo-chemical interaction thereof with the substituent R.sup.1, the steric configuration of the two asymmetric carbon atoms to which the R.sup.2 substituents are attached being identical; X is a sulfur atom or an oxygen atom; and n is an integer which is 1 or 2.Type: GrantFiled: December 9, 1982Date of Patent: January 22, 1985Assignee: Yamasa Shoyu Kabushiki KaishaInventors: Eiichi Fujita, Yoshimitsu Nagao, Takao Ikeda, Takehisa Inoue
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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: 4468395Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.Type: GrantFiled: May 20, 1982Date of Patent: August 28, 1984Assignee: Schering, AktiengesellschaftInventors: VorbruHelmut, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
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Patent number: 4384115Abstract: Tetrahydro-1,3-oxazin-2-ones are prepared by contacting a 1,3-dioxan-2-one with an acyclic carbamate at a temperature from about 100.degree. C. to about 250.degree. C. in the presence of a catalytic amount of an alkali metal salt.Type: GrantFiled: December 14, 1981Date of Patent: May 17, 1983Assignee: The Dow Chemical CompanyInventor: James M. Renga
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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: 4360696Abstract: A process is disclosed whereby acrylonitrile and diacetone alcohol are reacted in at least 93% sulfuric acid to form a novel intermediate reaction product which is recovered as a crystalline solid, washed with an organic solvent to remove colored oily impurities along with sulfuric acid, and hydrolyzed to produce diacetone acrylamide, a reactive monomer useful for preparing polymeric components of photographic films and adhesives. The intermediate reaction product is identified as 5,6-dihydro-6-hydroxy-4,4,6-trimethyl-2-vinyl-1,3(4H)-oxazine sulfate (1:1).Type: GrantFiled: June 2, 1980Date of Patent: November 23, 1982Assignee: American Cyanamid CompanyInventor: Henry Richmond
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Patent number: 4309425Abstract: Sulfonamides, such as N-[N-(2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-(trifluoromethy l)phenyl]aminothio]-N,4-dimethylbenzenesulfonamide, are useful for control of arthropod pests of plants and animals and fungus disease of plants.Type: GrantFiled: April 11, 1980Date of Patent: January 5, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Jiin-Duey Cheng
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Patent number: 4247689Abstract: The present invention relates to a new organic heterocyclic isocyanate which is the reaction product of an organic diisocyanate and an amino or hydroxy nitrile. The invention also relates to a process of producing such isocyanates by reacting an excess of the diisocyanate with the nitrile under conditions under which the nitrile will not decompose and then maintaining the reaction mixture at an elevated temperature until the isocyanate nitrile adduct cyclizes. The reaction may be carried out in the presence of a catalyst for isocyanate addition reactions. Additionally, the invention relates to a process for the production of polyurethane by the reaction of the heterocyclic isocyanates with compounds carrying at least two isocyanate reactive hydrogen atoms per molecule.Type: GrantFiled: June 11, 1979Date of Patent: January 27, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Kuno Wagner, Walter Uerdingen
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Patent number: 4239885Abstract: A process is disclosed whereby acrylonitrile and diacetone alcohol are reacted in at least 93% sulfuric acid to form a novel intermediate reaction product which is recovered as a crystalline solid, washed with an organic solvent to remove colored oily impurities along with sulfuric acid, and hydrolyzed to produce diacetone acrylamide, a reactive monomer useful for preparing polymeric components of photographic films and adhesives. The intermediate reaction product is identified as 5,6-dihydro-6-hydroxy-4,4,6-trimethyl-2-vinyl-1,3(4H)-oxazine sulfate (1:1).Type: GrantFiled: June 28, 1978Date of Patent: December 16, 1980Assignee: American Cyanamid CompanyInventor: Henry Richmond
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Patent number: 4173567Abstract: The present invention relates to a new organic heterocyclic isocyanate which is the reaction product of an organic diisocyanate and an amino or hydroxy nitrile. The invention also relates to a process of producing such isocyanates by reacting an excess of the diisocyanate with the nitrile under conditions under which the nitrile will not decompose and then maintaining the reaction mixture at an elevated temperature until the isocyanate nitrile adduct cyclizes. The reaction may be carried out in the presence of a catalyst for isocyanate addition reactions. Additionally, the invention relates to a process for the production of polyurethane by the reaction of the heterocyclic isocyanates with compounds carrying at least two isocyanate reactive hydrogen atoms per molecule.Type: GrantFiled: February 10, 1976Date of Patent: November 6, 1979Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Kuno Wagner, Walter Uerdingen
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Patent number: 4163848Abstract: Production of 2-alkyl- or cycloalkyl-4-methyl-6-hydroxypyrimidines by first neutralizing an alkyl imidate ester hydrochloride with a base in the presence of a water-immiscible solvent for the alkyl imidate ester to be freed thereby; condensing the alkyl imidate ester with diketene to form an oxazinone intermediate, which is then reacted in organic solution with gaseous ammonia and recovering the desired substituted 6-hydroxypyrimidine.Type: GrantFiled: August 8, 1978Date of Patent: August 7, 1979Assignee: Ciba-Geigy CorporationInventors: Joseph T. Blackwell, III, John T. Gupton, Teruko U. Miyazaki, James B. Nabors, Joseph R. Pociask
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Patent number: 4151279Abstract: N-carbamyloxy-6-oxotetrahydro-1,3-oxazines of the formula ##STR1## wherein R is hydrogen, alkyl or aryl,R.sup.1 and R.sup.2 are alkyl or aryl,X is halo,R.sup.3 and R.sup.4 are hydrogen, alkyl or halo, with the proviso that two R.sup.1 and R.sup.2 groups may together form a divalent alkylene group of 3 to 5 carbon atoms, have been round to be excellent plant fungicides, particularly for plant diseases caused by Phytophthora infestans and the fungal species of the Peronosporaceae family.Type: GrantFiled: June 19, 1978Date of Patent: April 24, 1979Assignee: Chevron Research CompanyInventor: Malcolm S. Singer
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Patent number: 4128558Abstract: Phosphonic acid esters of the formula ##STR1## in which R.sub.1 and R.sub.2 represent optionally halogen-substituted alkyl or together with --O--P--O-- form a five-membered to seven-membered heterocyclic structure,X represents oxygen or ##STR2## wherein R.sub.4 represents hydrogen or alkyl,R represents alkylene with 1 - 4 carbon atoms andA represents alkylene or 1,2-phenylene, which is optionally substituted by halogen, alkyl or halogenoalkyl and is required to complete a five-membered to seven-membered ring system,Are suitable as flameproofing agents for textiles, plastics and paper.Type: GrantFiled: July 11, 1975Date of Patent: December 5, 1978Assignee: Bayer AktiengesellschaftInventors: Udo W. Hendricks, Klaus Walz
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Patent number: 4107435Abstract: 1-N-(.omega.-Amino-2-hydroxyalkyl) derivatives of aminoglycoside antibiotics are prepared by reductive alkylation of the parent antibiotic, or a partially protected derivative thereof, with a 6-dihydroxymethyltetrahydro-1, 3-oxazin-2-one or 5-dihydroxymethyloxazolidin-2-one, followed by hydrolysis, and, if necessary, followed by removal of any remaining protecting groups. The products of the process of this invention are known antibacterial agents.Type: GrantFiled: February 10, 1977Date of Patent: August 15, 1978Assignee: Pfizer Inc.Inventor: Barry C. Ross
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Patent number: 4071512Abstract: The invention provides a novel process for opening the ring of 2-R-6-(1'-R.sup.1 -oxycarbonyl-2'-methyl-prop-1'-enyl)-1-oxa-3,6-diaza-4S,5R-bicyclo[3,2,0]h ept-2-en-7-one by treatment with a sulfonic acid salt thereby forming R.sup.1 2-(2'R-R-oxy-3'S-amino-4'-oxo)azetidinyl-3-methyl-2-butenoate sulphonic acid salts which can provide oxapenicillins by two different routes depending on the substituent desired on the carboxamido group of the 1-oxapenicillins. In the alternate processes, new intermediates are also provided.Type: GrantFiled: June 17, 1975Date of Patent: January 31, 1978Assignee: Queen's University at KingstonInventor: Saul Wolfe
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Patent number: 4042595Abstract: A ketonic heterocyclic compound having at least two heteroatoms in the ring is prepared by reacting a difunctional compound having the general formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are members of the group consisting of aliphatic, aromatic, cycloaliphatic and heterocyclic hydrocarbons which may contain functional groups selected from --OH, --OR.sub.5, --COOH, --COOR.sub.5, --CN, --Cl, --Br, --I, --F, and --CO--R.sub.5, wherein R.sub.5 is an aliphatic, aromatic, cycloaliphatic or heterocyclic hydrocarbon; X is oxygen or sulphur; Y is sulphur or nitrogen; n is an integer ranging from 1 to 3, or zero; R.sub.6 is a hydrogen or a hydrocarbon radical included in the above definition of R.sub.1 R.sub.2 R.sub.3 and R.sub.4 ; and m is the valence of Y, with carbon monoxide and oxygen in the presence of a catalyst selected from selenium, selenium compounds and complexes of copper, in the temperature range of from room temperature to 80.degree.Type: GrantFiled: February 4, 1976Date of Patent: August 16, 1977Assignee: Snam Progetti S.p.A.Inventors: Paolo Koch, Emilio Perrotti