Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Hetero Ring Patents (Class 549/64)
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Patent number: 4668800Abstract: There is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.Type: GrantFiled: March 4, 1985Date of Patent: May 26, 1987Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner F/o/ ry, Werner T/o/ pfl
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Patent number: 4638075Abstract: Sulfonamides derived from substituted 2-amino-1,2,4-triazolo[1,5-a]pyrimidines are prepared by reacting a desired sulfonamide with dimethyl N-cyanodithioiminocarbonate in the presence of a base followed by reaction with an excess of hydrazine and then a 1,3-dicarbonyl compound.The resulting products have a variety of herbicidal uses.Type: GrantFiled: December 23, 1985Date of Patent: January 20, 1987Assignee: The Dow Chemical CompanyInventors: William A. Kleschick, Anna P. Vinogradoff, Joseph E. Dunbar
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Patent number: 4599350Abstract: Novel fungicidal active thiolane-2,4-dione-3-carboxamides of the formula ##STR1## in which R is alkyl, cycloalkyl, optionally substituted aralkyl or optionally substituted aryl, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, aralkyl or aryl.Type: GrantFiled: November 27, 1984Date of Patent: July 8, 1986Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
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Patent number: 4568691Abstract: The invention concerns novel esters of 4-(1-hydroxy-2-[(acylamino)alkylamino]ethyl)phenols of the formula: ##STR1## and salts thereof, wherein R.sup.1 and R.sup.2 are (3-5C)alkyl, R.sup.3 and R.sup.4 are hydrogen or methyl, A is a direct bond or methylene, and Q is various heteroaromatic containing groups. The esters possess topical anti-inflammatory properties and the invention provides pharmaceutical compositions containing the esters and processes for their chemical manufacture.Type: GrantFiled: December 20, 1984Date of Patent: February 4, 1986Assignee: Imperial Chemical Industries, PLCInventors: Peter R. Marsham, David S. Thomson
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Patent number: 4565826Abstract: This invention relates to a novel class of heterocyclic amidinourea and heterocyclic amidinothiourea compounds wherein the heterocyclic substitution is at the 1-N urea nitrogen atom. These compounds exhibit pharmaceutical activity and may be incorporated into pharmaceutical preparations for producing anti-ulcerogenic, antisecretory, antispasmodic, antimotility, cardiovascular, antidiarrheal or antiparasitic action.Type: GrantFiled: February 24, 1984Date of Patent: January 21, 1986Assignee: William H. Rorer, Inc.Inventors: William L. Studt, Harry K. Zimmerman, George H. Douglas
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Patent number: 4520027Abstract: The invention concerns novel esters of 4-(1-hydroxy-2-[(acylamino)alkylamino]ethyl)phenols of the formula: ##STR1## and salts thereof, wherein R.sup.1 and R.sup.2 are (3-5C)alkyl, R.sup.3 and R.sup.4 are hydrogen or methyl, A is a direct bond or methylene, and Q is various heteroaromatic containing groups. The esters possess topical anti-inflammatory properties and the invention provides pharmaceutical compositions containing the esters and processes for their chemical manufacture.Type: GrantFiled: December 23, 1982Date of Patent: May 28, 1985Assignee: Imperial Chemical Industries PLCInventors: Peter R. Marsham, David S. Thomson
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Patent number: 4486444Abstract: (Hydroxybenzoyl)thiophenesulfonamide and acyl derivatives thereof are useful for the topical treatment of elevated intraocular pressure in ophthalmic compositions including drops and inserts.Type: GrantFiled: June 20, 1983Date of Patent: December 4, 1984Assignee: Merck & Co., Inc.Inventor: Kenneth L. Shepard
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Patent number: 4454131Abstract: This invention relates to new thiophene derivatives and their use as fungicides in agriculture and horticulture.Type: GrantFiled: April 26, 1983Date of Patent: June 12, 1984Assignees: Ube Industries, Ltd., Hokko Chemical Industry Co., Ltd.Inventors: Yojiro Hirota, Koichi Shinhama, Katsumi Sato, Takuo Wada
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Patent number: 4447624Abstract: Process for the preparation of thiophenes having the structure ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can be various substituents. The compounds can be converted to the corresponding 2-amino compounds from which azo dyes can be prepared.Type: GrantFiled: June 21, 1982Date of Patent: May 8, 1984Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Robert J. Maleski
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Patent number: 4421761Abstract: Thiophene derivatives of the formula ##STR1## wherein X, Y and Z are as herein defined, said compounds being useful as fungicides, are described.Type: GrantFiled: January 27, 1981Date of Patent: December 20, 1983Assignees: Hokko Chemical Industry Co. Ltd., Ube Industries, Ltd.Inventors: Shigeki Nagai, Takashi Yorie, Hisao Sugiura, Toru Hibi, Katsumi Sato, Takuo Wada, Masahiko Miyahara
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Patent number: 4417072Abstract: Substituted hydroquinone compounds of the formula ##STR1## wherein R.sub.1 to R.sub.4 are hydrogen or alkyl and Z is an aromatic ring or a group of the formula --X--Y--X--, wherein X is an aromatic ring and Y is an electron withdrawing group, are incorporated as developers into photographic materials. These materials are suitable for activation processings.Type: GrantFiled: September 29, 1981Date of Patent: November 22, 1983Assignee: Ciba-Geigy AGInventors: Stephen R. Postle, Patrick D. P. Thomas, Brian R. D. Whitear
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Patent number: 4412856Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.Type: GrantFiled: May 22, 1981Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4352819Abstract: The disclosure is directed to novel 1-[3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl]-3-phenyl-1-propanones and their salts. The compounds of the invention have the structural formula ##STR1## in which R and R.sub.1 are independently hydrogen or methyl and R.sub.2 is n-propyl, n-butyl, isobutyl or tert-butyl. The compounds have an outstanding antiarrhytmical activity already in low doses.Type: GrantFiled: November 25, 1981Date of Patent: October 5, 1982Assignee: Laevosan-Gesellschaft mbH & Co. KGInventor: Dieter Binder
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Patent number: 4331680Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: August 25, 1980Date of Patent: May 25, 1982Assignee: The Boots CompanyInventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
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Patent number: 4304941Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a clay.Type: GrantFiled: August 1, 1980Date of Patent: December 8, 1981Assignee: Hoechst Roussel Pharmaceuticals, Inc.Inventors: Thomas B. K. Lee, Gregory M. Jobin
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Patent number: 4297489Abstract: Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-ca rboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.Type: GrantFiled: June 27, 1975Date of Patent: October 27, 1981Assignee: Bristol-Myers CompanyInventors: William J. Gottstein, Murray A. Kaplan, Alphonse P. Granatek
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Patent number: 4271171Abstract: Aroylureas of the formula ##STR1## where A denotes a phenyl, thienyl or pyridyl-3 radical which is mono- or polysubstituted by halogen, linear or branched alkyl of 1 to 4 carbon atoms, or linear or branched alkoxy of 1 to 4 carbon atoms, R denotes linear or branched alkyl of 1 to 4 carbon atoms or linear or branched alkoxy of 1 to 4 carbon atoms, and n denotes one of the integers 0,1 and 2, which have an insecticidal and acarididal action, and a process for combating insects and mites with these active ingredients.Type: GrantFiled: May 2, 1980Date of Patent: June 2, 1981Assignee: BASF AktiengesellschaftInventors: Annegrit Baumann, Karl Kiehs, Heinrich Adolphi, Karl-Heinz Koenig
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Patent number: 4266066Abstract: Ketones are prepared by reacting carboxylic acid halides, in particular carboxylic acid chlorides, with aluminum-alkyl compounds, optionally in the presence of an aluminum trihalide, in methylene chloride as the solvent, at a temperature between about 20.degree. and about 100.degree. C., preferably between about 30.degree. and about 60.degree. C., more preferably of about 40.degree. C. which is the reflux temperature of the methylene chloride. When operating at a temperature above approximately 40.degree. C., pressure higher than atmospheric is applied. The reaction mixture is worked up in usual manner, suitably by decomposition with water followed by distillation.Type: GrantFiled: November 26, 1979Date of Patent: May 5, 1981Assignee: Hoechst AktiengesellschaftInventors: Werner Spielmann, Georg Schaeffer
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Patent number: 4239897Abstract: New thiophene compounds and a new process for the manufacture of thiophene compounds by dehydrogenating dihydrothiophene with certain halogen compounds. The products are starting materials for the manufacture of pharmaceuticals, dyes and plant protection agents and, in particular, for the manufacture of additives to foodstuffs, feeds, beverages and pharmaceuticals.Type: GrantFiled: September 15, 1978Date of Patent: December 16, 1980Assignee: BASF AktiengesellschaftInventors: Phillip Rossy, Werner Hoffmann
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Patent number: 4230872Abstract: Novel 9-substituted or unsubstituted thienyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives, useful as antitumor agents as well as processes for their preparation and novel intermediates are disclosed.Type: GrantFiled: May 11, 1978Date of Patent: October 28, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Klaus, Beverly A. Pawson
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Patent number: 4230873Abstract: The invention relates to sulphothiophene-carboxylic acids of the following formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## and the broken line represents the double bond present in group (a), R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group; and the halides and lower alkyl esters thereof.Type: GrantFiled: March 2, 1977Date of Patent: October 28, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Otto Hromatka, Dieter Binder
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Patent number: 4230707Abstract: Oxo-pyrido[1,2-a]thienopyrimidine compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds and methods for treating allergies using said compositions are disclosed.Type: GrantFiled: August 27, 1979Date of Patent: October 28, 1980Assignee: Warner-Lambert CompanyInventors: Francis J. Tinney, David T. Connor, Wiaczeslaw A. Cetenko, Joseph J. Kerbleski, Roderick J. Sorenson
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Patent number: 4224445Abstract: The present invention relates to compounds of the formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## and the broken line represents the double bond in group (a); R.sub.1 represents a lower alkyl group; R.sub.2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group.Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and anti-rheumatic activity.Type: GrantFiled: October 30, 1978Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Otto Hromatka, Dieter Binder, Rudolf Pfister, Paul Zeller
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Patent number: 4221815Abstract: Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.Type: GrantFiled: January 2, 1976Date of Patent: September 9, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Werner Pfaff
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Patent number: 4219656Abstract: This application discloses novel substituted 4-(alkoxy or alkanoyloxy)-3-thiophenecarboxylic acids, esters, and amides which possess analgesic and antipyretic activity in warm-blooded animals.Type: GrantFiled: October 24, 1978Date of Patent: August 26, 1980Assignee: American Cyanamid CompanyInventors: Jeffery B. Press, Sidney R. Safir
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Patent number: 4214092Abstract: A method of preparing acyloxy furans and thiophenes from butenolides comprising reacting a pre-selected butenolide with an acylating agent in the presence of a base to provide an acyloxy furan intermediate, which in turn undergoes rearrangement in the presence of Lewis Acids by cleavage of a carbon-oxygen bond, and addition of the cleaved moiety to the furan ring forming a carbon-carbon bond on the ring. The result is a heretofore unknown group of lactone type compounds which are biologically active, in and of themselves, and in addition offer use as versatile synthesis intermediates to achieve, by conventional synthesis methods heretofore unavailable compounds.Type: GrantFiled: February 21, 1979Date of Patent: July 22, 1980Assignee: Iowa State University Research Foundation, Inc.Inventor: George A. Kraus
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Patent number: 4211878Abstract: Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(2-thenamidoacetamido)ethylaminopropan-2-ol.Type: GrantFiled: October 5, 1977Date of Patent: July 8, 1980Assignee: Imperial Chemical Industries LimitedInventor: Leslie H. Smith
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Patent number: 4182775Abstract: Benzoic acids of the general formula I ##STR1## in which R, R.sup.1, R.sup.2 and Y have the meanings as mentioned in the following, and which in the form of the free compounds or in the form of the physiologically tolerated salts and esters possess valuable pharmacological properties, processes for preparing them, pharmaceutical preparations containing them, and their use as or in medicaments.Type: GrantFiled: September 1, 1977Date of Patent: January 8, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Ernold Granzer
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Patent number: 4177193Abstract: The present invention relates to compounds of the formula ##STR1## wherein A together with the two carbon atoms to which it is attached forms the group ##STR2## and the broken line represents the double bond in group (a); R.sub.1 represents a lower alkyl group; R.sub.2 represents the residue of an aromatic heterocyclic ring containing from 1 to 4 hetero atoms, which may be substituted by one or two lower alkyl groups, or a phenyl group which may be substituted by halogen, hydroxy, lower alkyl, trifluoromethyl or lower alkoxy and R.sub.3 and R.sub.4 each represent a hydrogen atom or a lower alkyl group.Also provided are methods for their preparation. The thienothiazine derivatives provided by this invention have anti-flammatory, analgesic and anti-rheumatic activity.Type: GrantFiled: October 30, 1978Date of Patent: December 4, 1979Assignee: Hoffman-La Roche Inc.Inventors: Otto Hromatka, Dieter Binder, Rudolf Pfister, Paul Zeller