Hydroxy, Bonded Directly To Carbon, Or Ether In Substituent Q (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/89)
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Patent number: 4521619Abstract: Benzylidene derivatives of the formula: ##STR1## wherein n represents an integer from 1 through 4, R represents an amino radical, a monoalkylamino group containing 1 through 4 carbon atoms in the alkyl radical, a dialkylamino group containing 1 through 4 carbon atoms in each alkyl radical, or when n represents 2, 3 or 4 a group ##STR2## in which m represents 4 or 5, or a group --OM in which M represents an alkali metal or alkaline earth metal, and X.sub.1 X.sub.2, X.sub.3 and X.sub.4 each represent a hydrogen atom, a halogen atom, or an alkyl radical containing 1 through 6 carbon atoms, are new therapeutically useful compounds. They possess antidepressant, anticonvulsant, anxiolytic, analgesic, anti-inflammatory, ulcer-inhibiting, gastric antisecretory and antihypertensive properties.Type: GrantFiled: November 17, 1983Date of Patent: June 4, 1985Assignee: SynthelaboInventor: Jean-Pierre Kaplan
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Patent number: 4510325Abstract: N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formulaA is a C.sub.1 -C.sub.6 alkyl radical which is substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 haloalkylsulfinyl or C.sub.1 -C.sub.4 haloalkylsulfonyl, or a C.sub.2 -C.sub.6 -alkenyl radical which is unsubstituted or substituted by the above substituents, or is a C.sub.2 -C.sub.6 haloalkenyl radical,E is the methine group or nitrogen,X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is 1 or 2,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or a radical --Y--R.sub.5,R.sub.Type: GrantFiled: September 13, 1982Date of Patent: April 9, 1985Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fury
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Patent number: 4490555Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: March 19, 1982Date of Patent: December 25, 1984Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4487953Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.Type: GrantFiled: December 6, 1982Date of Patent: December 11, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
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Patent number: 4487961Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 16, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4487960Abstract: Novel compounds of the following formula: ##STR1##Type: GrantFiled: April 19, 1982Date of Patent: December 11, 1984Assignee: The Upjohn CompanyInventor: Chiu-Hong Lin
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Patent number: 4476321Abstract: N-Phenylsulfonyl-N'-pyrimidinyl- and triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties. In the above formulaA is a C.sub.1 -C.sub.6 haloalkyl radical,E is the methine group or nitrogen,X is oxygen, sulfur, a sulfinyl or sulfonyl bridge,Z is oxygen or sulfur,m is 1 or 2,R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl or a radical --Y--R.sub.5,R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.1 -C.sub.4 -haloalkyl, or a radical --Y--R.sub.5, --COOR.sub.6, --NO.sub.2 or --CO--NR.sub.7 --R.sub.8,R.sub.3 and R.sub.4, each independently of the other, are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, halogen or alkoxyalkyl of at most 4 carbon atoms,R.sub.5 and R.sub.Type: GrantFiled: September 24, 1982Date of Patent: October 9, 1984Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Fory
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Patent number: 4474806Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.Type: GrantFiled: May 10, 1982Date of Patent: October 2, 1984Assignee: Merck & Co., Inc.Inventors: Thomas R. Beattie, Shu S. Yang
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Patent number: 4447634Abstract: There is provided herbicidal arylsulfonamide derivatives of phenoxybenzoic acids. These compounds are particularly useful when applied in a post-emergence application to soybean fields containing broadleaf weeds.Type: GrantFiled: April 30, 1981Date of Patent: May 8, 1984Assignee: Rhone-Poulenc AgrochimieInventor: Guang-Huei Lee
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Patent number: 4443477Abstract: The invention provides sulphonamides of the formula ##STR1## wherein R is a hydrogen atom or a lower alkyl radical;R.sub.1 is alkyl, aryl, aralkyl or aralkenyl, the aryl moiety of which in each case can be optionally substituted one or more times by hydroxyl, halogen, trifluoromethyl, lower alkyl or alkoxy or by acyl, carboxy or alkoxycarbonyl;n is 1, 2 or 3; andW is a valence bond or a divalent aliphatic hydrocarbon linkageand the physiologically acceptable salts, esters and amides of such compound. These compounds have excellent pharmacological lipid depressing activity and inhibit thrombocyte aggregation.Type: GrantFiled: July 7, 1982Date of Patent: April 17, 1984Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hans P. Wolfe, Karlheinz Stegmeier, Egon Roesch
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Patent number: 4440943Abstract: 3,7-Substituted phenoxiodinin-5-ium compounds are effective against a variety of aerobic and anaerobic bacteria as well as fungi. The compounds of this invention may be prepared by the direct iodination of a suitably substituted diphenyl ether with iodosyl sulfate in concentrated sulfuric acid. The resulting bisulfate anion may be exchanged with a desired anion by standard metathetic processes.Type: GrantFiled: March 15, 1982Date of Patent: April 3, 1984Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
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Patent number: 4427685Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: a is 1 to 3;b is 0 to 2;c is 2 to 4;d is 1 to 5;X is sulphur, oxygen or --CH.sub.2 --;Y is oxygen, sulphur, NR.sub.4 or CHR.sub.5 wherein R.sub.4 is hydrogen, C.sub.1-4 alkyl, NO.sub.2 or CN, C.sub.1-4 alkylsulphonyl or phenylsulphonyl optionally substituted in the phenyl moiety by one or two substituents selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, fluorine, chlorine or bromine, and R.sub.5 is NO.sub.2, C.sub.1-4 alkylsulphonyl or optionally substituted phenylsulphonyl as defined for R.sub.4 ;R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1-4 alkyl, or C.sub.3-6 cycloalkyl; or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached represent a pyrrolidino or piperidino ring;R.sub.6 and R.sub.7 are independently hydrogen or C.sub.Type: GrantFiled: February 3, 1982Date of Patent: January 24, 1984Assignee: Beecham Group P.L.C.Inventor: Geoffrey Stemp
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Patent number: 4420632Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 13, 1983Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4413013Abstract: Novel pesticidal N-[[[arylformimidoyl]methylamino]thio]-N-substituted sulfonamides are disclosed with novel compositions thereof and methods for their use in controlling invertebrate arthropod pests, particularly insects, mites, and ticks.Type: GrantFiled: December 14, 1981Date of Patent: November 1, 1983Assignee: The Upjohn CompanyInventor: Victor L. Rizzo
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Patent number: 4401663Abstract: A compound, or pharmaceutically acceptable salt thereof, having the formula: ##STR1## wherein X is ##STR2## wherein R is C.sub.3 -C.sub.12 alkyl or aralkyl, branched or unbranched, unsubstituted aryl, haloaryl, or C.sub.3 -C.sub.22 alkenyl, branched or unbranched; wherein R.sub.1 is H, OH or OCH.sub.3, and wherein R.sub.2 is OH or H, at least one of R.sub.1 and R.sub.2 being OH or OCH.sub.3. These sulfonamides have analgesic and anti-irritant activity when administered to humans and lower animals.Type: GrantFiled: March 23, 1982Date of Patent: August 30, 1983Assignee: The Procter & Gamble CompanyInventors: Brian L. Buckwalter, Thomas R. LaHann
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Patent number: 4352760Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.Type: GrantFiled: December 29, 1980Date of Patent: October 5, 1982Assignee: The Upjohn CompanyInventor: Kirk M. Maxey
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Patent number: 4349689Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4338457Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.Type: GrantFiled: February 28, 1980Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4330542Abstract: The invention relates to novel aniline derivatives of the formula: ##STR1## wherein R.sub.1 and R.sub.2 represent a hydrogen or chlorine atom, an allyloxy, acetamide or carboxamide group, R.sub.3 represents a methyl or an optionally substituted phenyl group, R.sub.4 represents a hydrogen atom and R.sub.5 an isopropyl, terbutyl, 2-phenoxy-ethyl or 3-phenyl-propyl group or R.sub.3 and R.sub.5 taken together form with the nitrogen atom a substituted heterocyclic group.The compounds of the invention are useful for the treatment of angina pectoris.Type: GrantFiled: May 16, 1980Date of Patent: May 18, 1982Assignee: SanofiInventors: Marcel Descamps, Charles Goldenberg
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Patent number: 4268669Abstract: The present invention particularly relates to novel 9-deoxy-9-methylene-5,6-didehydro-PGF.sub.1 amides and methods for their preparation in pharmacological use.Type: GrantFiled: January 28, 1980Date of Patent: May 19, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4266078Abstract: Described herein are herbicidal compositions comprised of a thiocarbamate or haloacetanilide herbicide and an antidotally effective amount of an N-acylsulfonamide compound corresponding to the formula ##STR1## in which R is selected from the group consisting of hydrogen, methyl, chloro, acetamido, and 1-4 carbon alkoxyamido;R.sub.1 is selected from the group consisting of hydrogen, allyl, and metal ion;R.sub.2 is selected from the group consisting of 1-10 carbon alkyl, 1-4 carbon haloalkyl, 2-4 carbon alkenyl, 2-4 carbon haloalkenyl, acetonyl, 1-6 carbon alkoxy, 1-4 carbon alkoxycarbonyl, 1-4 carbon alkylthioalkyl, alkoxyalkyl, O,O-dialkylphosphorodithioylalkyl, phenyl, halophenyl, halophenylthioalkyl, cyclohexanedione, and dimethyl barbituric acid; orR.sub.1 and R.sub.2 together with the carbonyl group to which R.sub.2 is attached are selected from the group consisting of succinimide, substituted succinimide, phthalimide, and substituted phthalimide.Type: GrantFiled: April 20, 1979Date of Patent: May 5, 1981Assignee: Stauffer Chemical CompanyInventor: Ferenc M. Pallos
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Patent number: 4258058Abstract: Phenoxyalkylcarboxylic acid compounds of the formula ##STR1## wherein R is hydrogen or lower alkylR.sub.1 is alkyl or aryl, aralkyl or aralkenyl radical, the aryl moiety of which can be substituted one or more times by halogen, hydroxyl, trifluoromethyl or lower alkyl, alkoxy or acylR.sub.2 and R.sub.3 are individually selected from hydrogen or lower alkyl, andn is 0, 1, 2 or 3and the physiologically acceptable salts, esters and amides thereof; are outstandingly effective in inhibiting thrombocyte aggregation.Type: GrantFiled: February 26, 1979Date of Patent: March 24, 1981Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hans P. Wolff, Max Thiel, Karlheinz Stegmeier, Egon Roesch
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Patent number: 4244887Abstract: Substituted novel .omega.-pentanorprostaglandins and various novel intermediates and reagents used in their preparation.Type: GrantFiled: August 20, 1979Date of Patent: January 13, 1981Assignee: Pfizer Inc.Inventors: Jasjit S. Bindra, Michael R. Johnson
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Patent number: 4233061Abstract: A compound of the general formula ##STR1## wherein R.sub.0 represents an alkyl group optionally having a substituent selected from the class consisting of a cyano group, lower alkoxy groups and di-(lower alkyl)amino groups, a lower alkenyl group, or a lower alkynyl group; R.sub.1, R.sub.2 and R.sub.3, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, independently from each other, represent a hydrogen atom, a halogen atom, a lower alkyl group, or a lower alkoxy group; Y represents a group of the formula ##STR2## or a group of the formula ##STR3## in which one of R.sub.9 and R.sub.10 is a lower alkyl group and the other is a hydrogen atom or a lower alkyl group; with the proviso that when Y is the group ##STR4## and R.sub.0 represents an unsubstituted alkyl group, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 do not represent hydrogen atoms at the same time.Type: GrantFiled: December 29, 1978Date of Patent: November 11, 1980Assignee: Utsunomiya UniversityInventors: Tetsuo Takematsu, Makoto Konnai, Hiroyoshi Omokawa