Carbocyclic Ring Bonded Directly To The -c(=x)- (e.g., 3-benzoyl Pyrrolidine, Etc.) Patents (Class 548/539)
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Patent number: 4751315Abstract: A new synthetic route to clausenamide having the formula ##STR1## has been found. It has been found that a compound of the formula ##STR2## can be oxidized to provide the stereochemically correctly configured product, clausenamide. A number of new compounds useful in the total synthesis of clausenamide have also been found. These compounds have the general formula ##STR3## wherein R is ##STR4## and CH.sub.2 OH.Type: GrantFiled: September 1, 1987Date of Patent: June 14, 1988Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical SciencesInventor: Wolfgang Hartwig
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Patent number: 4746677Abstract: A compound of formula (I): ##STR1## or a salt thereof; wherein Z represents a heterocyclic ring and R.sup.2 and R.sup.3 are independently selected from hydrogen, nitrile, CONH.sub.2, and SO.sub.2 R.sup.4 wherein R.sup.4 is optionally substituted aryl, optionally substituted alkyl, aralkyl or cycloalkyl or R.sup.2 and R.sup.3 together form an optionally substituted methylene group or a bond, intermediates, compositions, insecticidal and nematicidal use.Type: GrantFiled: July 1, 1987Date of Patent: May 24, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael D. Turnbull, Ian T. Kay
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Patent number: 4737513Abstract: Novel pyrrole derivatives of the formula ##STR1## wherein one of R.sub.2 and R.sub.3 is ##STR2## and the other of R.sub.2 and R.sub.3 as well as R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms, --CN, --CF.sub.3, --NO.sub.2, --COOAlk and Alk is alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, ##STR3## n is 0, 1 or 2, R', R.sub.1 ' and R.sub.2 ' are alkyl of 1 to 8 carbon atoms and R.sub.4 and R.sub.5 taken together with the carbon atoms to which they are attached may form an optionally further unsaturated carbon homocycle of up to 8 carbon atoms, Z is selected from the group consisting of hydrogen, --CN, --C.tbd.CH, --CF.sub.3 and alkyl of 1 to 3 carbon atoms, A is the residue of a pyrethrinoid acid, R.sub.Type: GrantFiled: August 13, 1985Date of Patent: April 12, 1988Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Laurent Taliani
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Patent number: 4731455Abstract: A process for the preparation of a C(3)-C(4)-transconfigurated .gamma.-butyrolactam of the formula (I) ##STR1## in which R.sup.1 represents hydrogen or alkyl, aryl or aralkyl with in each case up to 10 carbon atoms andR.sup.2 and R.sup.3 are identical or different and represent hydrogen, alkyl, aryl, aralkyl, alkoxy, aryloxy or aralkoxy with in each case up to 10 carbon atoms, acyl with up to 18 carbon atoms, trifluoromethyl, trifluoromethoxy, nitro, hydroxyl, halogen, amino, carboxyl, sulpho, dialkylamino with up to 4 carbon atoms in the alkyl groups or acylamino with up to 18 carbon atoms,in the form of their isomers, isomer mixtures, racemates or optical antipodes, comprising oxidizing a compound of the formula (II) ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the above-mentioned meanings, in an inert organic solvent in the presence of a base. Such .gamma.-butyrolactams have an antiamnesic action.Type: GrantFiled: October 1, 1986Date of Patent: March 15, 1988Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical SciencesInventor: Wolfgang Hartwig
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Patent number: 4731456Abstract: A new synthetic route to clausenamide having the formula ##STR1## has been found. It has been found that a compound of the formula ##STR2## can be oxidized to provide the stereochemically correctly configured product, clasuenamide. A number of new compounds useful in the total synthesis of clausenamide have also been found. These compounds have the general formula ##STR3## wherein R is ##STR4## and CH.sub.2 OH.Type: GrantFiled: October 3, 1986Date of Patent: March 15, 1988Assignees: Bayer Aktiengesellschaft, Chinese Academy of Medical SciencesInventor: Wolfgang Hartwig
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Patent number: 4693745Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.3 -C.sub.6 cycloalkyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy; orR.sub.3 and R.sub.Type: GrantFiled: October 9, 1985Date of Patent: September 15, 1987Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4652303Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.Type: GrantFiled: July 2, 1984Date of Patent: March 24, 1987Assignee: ICI Australia LimitedInventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
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Patent number: 4644009Abstract: Provided are new compounds having valuable therapeutic activity. These compounds are of the formula: ##STR1## and salts thereof, whereinX=O, S or NR.sub.2 ;Z=(CHR.sub.3).sub.n C(R.sub.3))OH)--, ##STR2## --CH.sub.3 .dbd.CH.sub.3 CR.sub.3 (OH)--, or --(CHR.sub.3).sub.n', M=--O--, --S--, or ##STR3## Z.sub.1 is an alkylene chain of 0-5 carbon atoms in the principal chain and a total of 7 carbon atoms;R.sub.1 is H, phenyl, naphthyl or a sulfur, nitrogen or oxygen-heterocyclic ring;R.sub.2 is H, alkyl, aryl or aralkyl;R.sub.3 is H or CH.sub.3 ;n=0-5; andn'=1-5.Type: GrantFiled: October 29, 1984Date of Patent: February 17, 1987Assignee: USV Pharmaceutical CorporationInventors: Fu-chih Huang, Joseph Auerbach
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Patent number: 4640706Abstract: Novel cyclohexenonecarboxylic acid derivatives exhibit herbicidal and plant growth regulating activity.The cyclohexenonecarboxylic derivatives are of the formula I ##STR1## wherein A is an aliphatic or aromatic alcohol, or is an amino group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano, or is a heterocyclic amino group which is unsubstituted or substituted,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,B is an aliphatic or aromatic radical or is an aliphatic or aromatic carbonyl or sulfonyl group which may be substituted by halogen, lower alkoxy, lower alkylthio, nitro or cyano.The compounds are suitable for selectively controlling grasses in crops of useful plants.Type: GrantFiled: March 20, 1985Date of Patent: February 3, 1987Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4629739Abstract: Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.Type: GrantFiled: September 23, 1985Date of Patent: December 16, 1986Assignee: Schering A.G.Inventors: David D. Davey, William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4623382Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloaklyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 -alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.Type: GrantFiled: October 16, 1985Date of Patent: November 18, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4618360Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkythio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.Type: GrantFiled: November 19, 1984Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4588727Abstract: There are described novel pyrrolo[1,2-b][1,2,5]triazepines of the general formula ##STR1## where R is hydrogen, loweralkyl, loweralkylaminoloweralkyl or diloweralkylaminoloweralkyl; X is hydrogen, halogen (fluorine, chlorine, bromine or iodine), trifluoromethyl or nitro; and Y is hydrogen, halogen or loweralkyl. Also described are derivatives of 1-amino-2-benzoylpyrrole having the general formula ##STR2## where R, X and Y are as defined above, and R.sub.1 is hydrogen, ##STR3##Compounds I and II are useful as analgesic, anxiolytic and/or anticonvulsant agents, and many of Compounds II are useful as intermediates for synthesizing Compounds I.Type: GrantFiled: February 4, 1985Date of Patent: May 13, 1986Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Richard C. Effland, Joseph T. Klein, R. Richard L. Hamer
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Patent number: 4585784Abstract: Novel pyrrole-2-acetylamino compounds of the formula: ##STR1## and salts thereof, wherein R" is H, alkyl, (CH.sub.2).sub.n CO.sub.2 H, CH.sub.2 CH.sub.2 SCH.sub.3, (CH.sub.2).sub.4 NH.sub.2 or (CH.sub.2).sub.2 CONH.sub.2 ; and n is 1 or 2, which have the same analgesic and antiinflammatory utility as zomepirac, but with reduced liability toward gastrointestinal irritation, and esters of the compounds of the above formula which are useful as intermediates to make said compounds.Type: GrantFiled: January 26, 1983Date of Patent: April 29, 1986Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4584013Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.Type: GrantFiled: May 14, 1984Date of Patent: April 22, 1986Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4578481Abstract: N-monosubstituted and N,N-disubstituted amides of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid, which are active as antiinflammatory, analgesic, antipyretic, antisecretive and antitussive agents, are disclosed.These amides are prepared by reacting an amine with an activated derivative of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid of formula ##STR1## wherein X is an activating group suitable for promoting the formation of an amide bond.Type: GrantFiled: April 30, 1985Date of Patent: March 25, 1986Assignees: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A., Medosan Industrie Biochimie Riunite S.p.A.Inventor: Alessandro Baglioni
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Patent number: 4571399Abstract: A new therapeutic agent with anti-platelet aggregant activity is described, with the chemical formula of 7-(1-methyl-5-p-methylbenzoylpyrrole-2-acetamidoethyl)-theophylline: ##STR1##Type: GrantFiled: July 26, 1984Date of Patent: February 18, 1986Assignee: Medosan Industrie Biochimiche Riunite S.p.A.Inventor: Alessandro Baglioni
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Patent number: 4568690Abstract: The anilide derivates of 1-methyl-5-p-methylbenzoylpyrrole-2-acetamidoacetic acid are described, with general formula ##STR1## in which R, R', R" and R"' may be hydrogen, halogen, alkyl, alkoxyl or a trifluoromethyl group. The compounds show useful antiinflammatory analgesic, anti-pyretic and antiplatelet aggregant activities.Type: GrantFiled: July 26, 1984Date of Patent: February 4, 1986Assignee: Medosan Industrie Biochimide Riunite S.P.A.Inventor: Alessandro Baglioni
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Patent number: 4549016Abstract: Novel 2-(hydroxyphenylamino)benzamides and oxidation products thereof, useful as inhibitors of lipoxygenase, are of the formulas ##STR1## wherein R is hydrogen, lower-alkyl, halo or lower-alkoxy; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and N.dbd.Z is amino or substituted amino. The compounds of Formula I are prepared by de-etherification of the corresponding alkyl or benzyl ethers; and the compounds of Formula II are prepared by oxidation of the compounds of Formula I where R' is hydrogen and OH is in the 4-position.Type: GrantFiled: January 9, 1985Date of Patent: October 22, 1985Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4544654Abstract: Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.Type: GrantFiled: March 20, 1984Date of Patent: October 1, 1985Assignee: Schering A.G.Inventors: David D. Davey, William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4528382Abstract: Novel compounds, which are aryl-pyrrolyl-imine derivatives of the Formula I ##STR1## and acid addition salts thereof are disclosed; which compounds may be prepared by the acid catalyzed condensation of an imidoyl chloride with a lower alkyl pyrrole-2-acetate; and which compounds are useful as intermediates to form by hydrolysis, the known useful ketone analogs which have anti-inflammatory and analgesic activity; and certain of which compounds have antisecretory, anti-irritable bowel, antidiarrheal and general behavior effect on the CNS properties.Type: GrantFiled: November 16, 1982Date of Patent: July 9, 1985Assignee: McNeilab, Inc.Inventor: John E. Mills
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Patent number: 4521538Abstract: 1-methyl-5-p-toluoylpyrrole-2-acetic acid guaiacyl ester, which possesses antiinflammatory, antipyretic, mucolytic and antitussive properties, is disclosed.This ester is prepared by reacting guaiacol with an activated derivative of the 1-methyl-5-p-toluoylpyrrole-2-acetic acid of formula ##STR1## wherein X is an activating group suitable for promoting the formation of an ester bond.Type: GrantFiled: March 4, 1983Date of Patent: June 4, 1985Assignee: Medosan Industrie Biochimiche Riunite S.p.A.Inventor: Alessandro Baglioni
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Patent number: 4511725Abstract: N-acyl-2,5-dimethylpyrroles and a process for their preparation. The process involves heating a mixture of acetonylacetone and an amide. The ensuing reaction is a condensation reaction with water being split out.Type: GrantFiled: January 17, 1983Date of Patent: April 16, 1985Assignee: Borg-Warner Chemicals, Inc.Inventors: Ingenuin Hechenbleikner, William P. Enlow
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Patent number: 4510139Abstract: Novel 2-(hydroxyphenylamino)benzamides and oxidation products thereof, useful as inhibitors of lipoxygenase, are of the formulas ##STR1## wherein R is hydrogen, lower-alkyl, halo or lower-alkoxy; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and N.dbd.Z is amino or substituted amino. The compounds of Formula I are prepared by de-etherification of the corresponding alkyl or benzyl ethers; and the compounds of Formula II are prepared by oxidation of the compounds of Formula I where R' is hydrogen and OH is in the 4-position.Type: GrantFiled: January 6, 1984Date of Patent: April 9, 1985Assignee: Sterling Drug Inc.Inventor: Denis M. Bailey
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Patent number: 4500341Abstract: Phenoxycarboxylic acid amide compound of the formula ##STR1## wherein R.sup.1 and R.sup.2 are individually selected from hydrogen and methyl,R.sup.3 is hydrogen or alkyl with from 1 to 5 carbon atomsR.sup.4 is optionally substituted alkoxycarbonylalkyl, aminocarbonylalkyl or dialkylaminocarbonylalkyl, phenyl, or substituted phenyl wherein the substituent is at least one of the group consisting of alkyl, alkoxy or alkylthio of from 1 to 4 carbon atoms, carbalkoxy of from 2 to 4 carbon atoms, halogen, and nitro; orR.sup.3 and R.sup.Type: GrantFiled: October 21, 1981Date of Patent: February 19, 1985Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Ludwig Eue, Robert R. Schmidt
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Patent number: 4499094Abstract: Compounds with the formula: ##STR1## in which R.sub.1 and R.sub.2 represent independently, a linear or branched alkyl, cycloalkyl, phenylalkyl or cycloalkylalkyl group. R.sub.1 and R.sub.2 may also represent an alkenyl or alkynyl group. R.sub.1 and R.sub.2 may also represent a group of the formula --R.sub.3 --Z--R.sub.4 in which R.sub.3 represents an alkylene group, on condition that at least 2 carbon atoms separate the nitrogen atom from the group Z; R.sub.4 represents an alkyl group, and Z an atom of oxygen, sulphur or the group >N--R.sub.5, R.sub.5 representing a hydrogen atom or an alkyl group. R.sub.1 and R.sub.2 may form, with the nitrogen atom to which they are attached, a heterocyclic ring. Ar represents a phenyl, pyridyl or thienyl group, or a substituted phenyl group, A and B representing independently, N or CH--, the group C representing the residue of a benzene or thiophene ring. These compounds can be used as medicaments, in particular, for the various applications of benzodiazepines.Type: GrantFiled: April 5, 1983Date of Patent: February 12, 1985Assignee: Pharmuka LaboratoiresInventors: Marie-Christine Dubroeucq, Christian Renault, Gerard Le Fur
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Patent number: 4497813Abstract: Derivatives of 3-aminopropane-1,2-diol of the formula ##STR1## in which Ar represents optionally substituted aryl,n represents the number 0 or 1, andalk represents alkylene having 2 to 5 carbon atoms, the nitrogen atom and the oxygen atom, or, if n is zero, the phenyl radical, being separated from one another by at least two carbon atoms, andR.sub.1 and R.sub.2, independently of one another, each represents hydrogen or lower alkyl, or together they represent lower alkylene, oxa-lower alkylene, thia-lower alkylene, aza-lower alkylene or N-lower alkyl-aza-lower alkylene,and salts of such compounds, processes for their manufacture, medicaments containing the new compounds and their use for the treatment of Angina pectoris and cardiac arrhythmia, and as blood pressure-reducing agents, as well as for the treatment of reactive or endogenic states of depression.Type: GrantFiled: May 14, 1982Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventors: Franz Ostermayer, Markus Zimmermann
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Patent number: 4486349Abstract: Process for preparing a para-quinone or ortho-quinone derivative, possibly alkoxylated or aryloxylated, which consists in oxidizing respectively the corresponding hydroquinone or pyrocatechic derivative, by means of the complex prepared, in situ or separately, by combining a cuprous salt, a hydrocarbon substituted by a cyano group and molecular oxygen, the oxidation being possibly carried out in the presence of an alkoxylating or aryloxylating agent of the hydroxylated derivative type.Type: GrantFiled: November 12, 1982Date of Patent: December 4, 1984Assignee: Delalande, S.A.Inventors: Michel Maumy, Patrice J. G. Capdevielle, Philippe L. Dostert, Michel Langlois
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Patent number: 4478836Abstract: The present invention concerns new derivatives of 1-aryl 2-aminomethyl cyclopropane carboxamides (Z) of general formula I: ##STR1## in which: R represents a hydrogen or halogen atom, a lower alkyl group, a lower alkoxy group, or a hydroxy. nitro or amino group;n represents the value 1 or 2;R.sub.1 and R.sub.2 represent a hydrogen atom, a lower alkyl group, an aryl or lower alkaryl group, possibly substituted, preferably in para position, by a halogen atom, preferably a chlorine atom;R.sub.1 and R.sub.2 may also form a heterocycle having 5 or 6 members with the adjacent nitrogen atom;R.sub.3 and R.sub.4 represent a hydrogen atom or a lower alkyl group;R.sub.3 and R.sub.Type: GrantFiled: June 22, 1982Date of Patent: October 23, 1984Assignee: Pierre Fabre S.A.Inventors: Gilbert Mouzin, Henri Cousse, Bernard Bonnaud, Michel Morre, Antoine Stenger
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Patent number: 4465843Abstract: The derivatives of 2-pyrrole-acetic acid having the formula: ##STR1## in which R.sub.1 is methyl or ethyl and X is hydrogen or chlorine, have a powerful anti-inflammatory action.These derivatives are prepared from ethyl 3,5-diethoxycarbonyl-4-methyl-2-pyrrole-acetate by alkylation, saponification, esterification, decarboxylation, benzoylation and saponification.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: Laboratories Pharmedical SAInventor: Margarita E. del Valle
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Patent number: 4462821Abstract: The present invention is directed to a class of novel 1-benzoyl-3-thiosemicarbazides which are useful as plant growth regulants. The present invention is also directed to methods and formulations for plant growth regulation.Type: GrantFiled: March 2, 1981Date of Patent: July 31, 1984Assignee: Gulf Oil CorporationInventors: Jerry L. Rutter, James L. Ahle
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Patent number: 4451658Abstract: Alkyl 1,4-dialkylpyrrole-2-alkanoates are prepared by the selective decarboxylation of a 1,4-dialkyl-3-carboxypyrrole-2-alkanoic acid or an alkyl ester or alkali metal salt thereof under moderate conditions with a mixture of a strong mineral acid, an alkanol, and water. The products are useful for the preparation of anti-inflammatory agents.Type: GrantFiled: December 9, 1982Date of Patent: May 29, 1984Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4440940Abstract: This disclosure describes 2- or 3-[(unsaturated or cyclopropylated alkyl)amino]phenyl compounds and derivatives useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: November 19, 1981Date of Patent: April 3, 1984Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4434175Abstract: 5-Aroyl-4-RO-, 5-aroyl-4-RS-, 5-aroyl-4-RSO-, 5-aroyl-4-RSO.sub.2 -, or 5-pyrrylcarbonyl-pyrrole alkanoic acid have been prepared via hydrolysis of a precursor-ester after high temperature decarboxylation or from direct acidic decarboxylation of a precursor diacid. The compounds are analgesic and anti-inflammatory agents of high activities but low ulcerogenic side effects.Type: GrantFiled: May 3, 1982Date of Patent: February 28, 1984Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Michael N. Chang, Conrad P. Dorn
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Patent number: 4418074Abstract: 3,5-Di(t-butyl)-4-(2'-pyrrolyl)phenol has pharmacological activity as an antiinflammatory agent.Type: GrantFiled: November 23, 1981Date of Patent: November 29, 1983Assignee: Riker Laboratories, Inc.Inventor: George G. I. Moore
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Patent number: 4398938Abstract: This invention relates to compounds of the formula: ##STR1## wherein X is halogen or trifluoromethyl; hydrogen, halogen or cyano; Z is halogen, cyano or nitro; R is alkyl; m is an integer from 0 to 6; and n is an integer from 3 to 5.Type: GrantFiled: May 20, 1982Date of Patent: August 16, 1983Assignee: Velsicol Chemical CorporationInventors: Leonard J. Stach, Frank Wu
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Patent number: 4396626Abstract: Compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts and pro-drugs thereof, wherein: Ar is a phenyl group optionally substituted by one or two moieties selected from halogen, C.sub.1-4 alkyl, methoxy, methylthio or trifluoromethyl, or a 2-thienyl group or N-methyl-2-pyrryl group optionally substituted by one or two C.sub.1-4 alkyl groups;R is hydrogen or methyl; andn is 0 or 1having useful anti-inflammatory and/or analgesic activity, pharmaceutical compositions containing them, and processes for their preparation.Type: GrantFiled: September 28, 1981Date of Patent: August 2, 1983Assignee: Beecham Group LimitedInventors: Robert W. Ward, Alexander C. Goudie
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Patent number: 4391816Abstract: Herein disclosed are N-(naphthalenylthioxomethyl)aminoacid derivatives having aldose reductase inhibiting activity. The derivatives are useful for treating diabetic complications.Type: GrantFiled: November 13, 1981Date of Patent: July 5, 1983Assignee: Ayerst, McKenna & Harrison Inc.Inventors: Kazimir Sestanj, Nedumparambil A. Abraham, Francesco Bellini, Adi Treasurywala
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Patent number: 4383112Abstract: Chiral Schiff bases according to the general formula: ##STR1## and transition metal complexes thereof, wherein C.sup.* is an asymmetric carbon atom, R.sup.1 and R.sup.2, which may be the same or different are alkyl, aralkyl, aryl or alkaryl, R.sup.3 is hydrogen, alkyl, aralkyl, aryl or alkaryl, R.sup.4 and R.sup.5, which may be the same or different, are hydrogen or lower alkyl or, where n is 1, may with the cyclic ring to which CR.sup.4 R.sup.Type: GrantFiled: July 8, 1980Date of Patent: May 10, 1983Assignee: Imperial Chemical Industries LimitedInventors: Dale A. Laidler, David J. Milner
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Patent number: 4379793Abstract: 4'-acetamidophenyl-2-(5'-p-toluyl-1'-methylpyrrole)acetate and related compounds exhibiting anti-inflammatory, analgesic and antipyretic activity are disclosed.Type: GrantFiled: July 20, 1981Date of Patent: April 12, 1983Assignee: Calzada y Cia, S.R.C.Inventors: Jose-Maria Calzada Badia, Antonio Boleda Vila, Jose Sabater Sanmartin, Maria J. Villazon Meneses
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Patent number: 4374997Abstract: Zomepirac and its analogs have been prepared from a 5-aroyl-3-hydroxycarbonyl-4-substituted pyrrole-2-acetic acid via acidic decarboxylation.Type: GrantFiled: June 4, 1981Date of Patent: February 22, 1983Assignee: Merck & Co., Inc.Inventors: James B. Doherty, Debra L. Allison
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Patent number: 4374254Abstract: A process for preparing 5-aroylpyrrole compounds and recovering them from crude solutions by extracting with a mixed organic extractant such as an aromatic hydrocarbon-alkanol mixture followed by aqueous extraction with a base, decolorizing, and recovering the 5-aroylpyrrole compound for final purification.Type: GrantFiled: January 23, 1981Date of Patent: February 15, 1983Assignee: Ethyl CorporationInventors: James T. F. Kao, Wayne D. Jensen
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Patent number: 4369139Abstract: 1-(p-methoxybenzoyl)-2-pyrrolidinone and intermediates useful in its preparation are described. The 1-(p-methoxybenzoyl)-2-pyrrolidinone is useful in the prevention of cerebral insufficiency.Type: GrantFiled: July 14, 1980Date of Patent: January 18, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Emilio Kyburz, Werner Aschwanden
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Patent number: 4347186Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen or lower alkyl; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl;are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.Type: GrantFiled: October 20, 1980Date of Patent: August 31, 1982Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse
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Patent number: 4347187Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen, lower alkyl, chloro or bromo; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl; are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.Type: GrantFiled: June 11, 1981Date of Patent: August 31, 1982Assignee: Syntex (U.S.A.) Inc.Inventors: Joseph M. Muchowski, Robert Greenhouse