Acyclic Chalcogen Bonded Directly To Ring Carbon Of The Bicyclo Ring System Patents (Class 546/116)
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Patent number: 4772612Abstract: Novel circulation active dihydropyridines of the formula ##STR1## in which X is CO, SO.sub.2 or CONH,R.sup.4 is H, OH, alkyl, halogen, acyloxy, alkoxyalkoxy, aralkyloxy, or together with R.sup.5 forms a heterocyclic ring, andthe other radicals are conventional in the dihydropyridine art,and pharmaceutically acceptable salts thereof.Type: GrantFiled: June 3, 1986Date of Patent: September 20, 1988Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Jurgen Stoltefuss, Gerhard Franckowiak, Rainer Gross, Matthias Schramm, Gunter Thomas
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Patent number: 4766213Abstract: Compounds of the formula ##STR1## are disclosed wherein the variables are herein described. These compounds are intermediates to compounds which influence the influx of calcium into the cell.Type: GrantFiled: January 16, 1987Date of Patent: August 23, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Horst Juraszyk, Rolf Gericke, Inge Lues, Rolf Bergmann, Claus J. Schmitges
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Patent number: 4754033Abstract: A process for producing pyridine-2,3-dicarboxylic acid derivatives of the formula ##STR1## is described. The process is based on the cleavage of HNR.sub.10 R.sub.11 from 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives of the formula II ##STR2## to give 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives of the formula III ##STR3## and subsequent oxidation of these compounds to obtain pyridine-2,3-dicarboxylic acid derivatives of the formula I. According to one variant of the process, the 1,4-dihydropyridine-2,3-dicarboxylic acid derivatives of the formula III are obtained directly, without isolation of the intermediately formed 1-amino-1,2,3,4-tetrahydropyridine-2,3-dicarboxylic acid derivatives of the formula II, by reaction of .alpha.,.beta.-unsaturated hydrazones of the formula IV ##STR4## with ethene-1,2-dicarboxylic acid derivatives of the formula V ##STR5## and subsequently oxidized to pyridine-2,3-dicarboxylic acid derivatives of the formula I. In the above formulae, R.sub.1, R.Type: GrantFiled: August 2, 1985Date of Patent: June 28, 1988Assignee: Ciba-Geigy CorporationInventor: Adrian Waldner
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Patent number: 4752323Abstract: There are provided novel (2-imidazolin-2-yl)thieno and furo compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: January 21, 1987Date of Patent: June 21, 1988Assignee: American Cyanamid CompanyInventors: Marinus Los, David W. Ladner, Barrington Cross
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Patent number: 4749702Abstract: Novel substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines useful as anti-depressives, in the treatment of Parkinson's disease and in the treatment of diseases related with disturbed enterokinesia.Type: GrantFiled: June 23, 1987Date of Patent: June 7, 1988Assignee: Janssen Pharmaceutica N. V.Inventors: Frans E. Janssens, Theophilus T. J. M. Van Offenwert, Raymond A. Stokbroekx, Bernard R. Boar
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Patent number: 4748244Abstract: The invention relates to a process for the preparation of pyridine-2,3-dicarboxylic acid derivatives of formula ##STR1## which process comprises reacting a hydrazone of formula II ##STR2## with a maleic acid derivative of formula III ##STR3## to give a 1-amino-1,4-dihydropyridine-2,3-dicarboxylic acid derivative of formula IV ##STR4## and subsequently removing R.sub.9 R.sub.10 NH. In the above formulae, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.9, R.sub.10 and X are as defined in claim 1. The pyridine-2,3-dicarboxylic acid derivatives of formula I are intermediates for the preparation of herbicidal compounds.Type: GrantFiled: May 3, 1985Date of Patent: May 31, 1988Assignee: Ciba-Geigy CorporationInventors: Adrian Waldner, Achim Roloff, Daniel Bellus
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Patent number: 4735950Abstract: This invention relates to 1,3-dihydro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula I ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various hydrocarbon groups and therapeutically acceptable addition salts thereof; to a process for the preparation of the same comprising oxidizing the secondary alcohol .alpha..sup.4, 3-o-isopropylidene-1-methyl-5-(1-hydroxy-1-A.sub.1)-methyl pyridine by any usual technique, reacting the resultant ketone with a compound of the general formula XA.sub.2 wherein X stands for Br or I in the presence of magnesium in diethyl ether at the boil and treating the resultant tertiary alcohol with an acidic agent to provoke breaking of the isopropylidene ring and 3,4-cyclisation; and to pharmaceutical compositions containing these derivatives useful for example in diuresis.Type: GrantFiled: March 30, 1987Date of Patent: April 5, 1988Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S)Inventor: Andre Esanu
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Patent number: 4730042Abstract: Pyridine derivatives of the formula ##STR1## where R.sup.1 to R.sup.4 have the meanings stated in the description, and their preparation.The substances are useful for treating disorders.Type: GrantFiled: May 30, 1986Date of Patent: March 8, 1988Assignee: BASF AktiengesellschaftInventors: Hans-Guenther Hege, Gerhard Eisen, Horst Koenig, Gerda von Philipsborn
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Patent number: 4721719Abstract: Reducing blood sugar with the novel dihydropyridinelactols, or salts thereof, of the formula ##STR1## in which R.sup.1 represents a phenyl, naphthyl, thienyl, pyridyl, chromonyl, thiochromonyl or thiochromenyl radical, the stated radicals optionally containing 1 or 2 identical or different substituents from the group consisting of fluorine, chlorine and bromine, alkyl, alkoxy and alkylthio, each having 1 to 6 carbon atoms, and fluoroalkyl or fluoroalkoxy, each having up to 3 carbon atoms and 3 fluorine atoms, and nitro and cyano,R.sup.2 represents a straight-chain, branched or cyclic alkyl having up to 12 carbon atoms which is optionally interrupted by 1 or 2 oxygen or sulphur atoms and which is optionally substituted by fluorine, chlorine, phenyl, cyano, hydroxyl, amino, C.sub.1 -C.sub.3 -alkylamino, di-C.sub.1 -C.sub.3 -alkylamino or N-benzylmethylamino,R.sup.3 represents cyano or straight-chain or branched alkyl which has up to 4 carbon atoms and is optionally interrupted in the chain by N-C.sub.1 -C.sub.Type: GrantFiled: August 27, 1986Date of Patent: January 26, 1988Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Friedrich Bossert, Hans J. Ahr, Hilmar Bischoff, Walter Puls, Dieter Petzinna, Klaus Schlossmann, Joachim Bender
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Patent number: 4705794Abstract: Pyridinecarboxylic acid esters of the formula ##STR1## in which R is an optionally substituted aryl or heterocyclic radical,R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, aralkyl, acyloxyalkyl or hydroxyalkyl, or R.sup.1 with X forms a carbonyl-containing heterocyclic ring,X is --CN, --CO--R.sup.4, --COOR.sup.5 or --SO.sub.2 R.sup.6,R.sup.4, R.sup.5 and R.sup.6 are various optionally substituted radicals, andR.sup.3 is different from R.sup.5 and is a substituted or interrupted hydrocarbon radical,or pharmaceutically acceptable salts thereof control the otherwise negative effects of ischaemia and/or hypoxia.Type: GrantFiled: February 28, 1983Date of Patent: November 10, 1987Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Ulrich Benz
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Patent number: 4696694Abstract: A pyridine derivative having the formula: ##STR1## wherein one of A, B, D and E is oxygen, sulfur, --SO--, --SO.sub.2 --, --NR.sup.3 --, ##STR2## or .dbd.CH-- with the rest being all carbon atoms; X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthioalkyl, tetrahydrothiopyranyl, hydroxyl, CF.sub.3, phenyl or pyridyl; n is an integer of from 0 to 6,; W is oxygen or sulfur; R is hydrogen, di-lower alkylimino, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl, C.sub.4 or C.sub.5 oxacycloalkyl, C.sub.2 -C.sub.5 mono-, di- or tri-haloalkenyl, C.sub.2 -C.sub.5 haloalkynyl, glycidyl, furfuryl, alkylthioalkyl, C.sub.3 -C.sub.6 cycloalkyl or a cation R.sup.1 is C.sub.1 -C.sub.4 alkyl, R.sup.2 is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or R.sup.1 and R.sup.Type: GrantFiled: July 7, 1986Date of Patent: September 29, 1987Assignee: Nissan Chemical Industries Ltd.Inventors: Tatsuo Numata, Masataka Hatanaka, Junichi Watanabe, Takasi Ikai, Tsutomu Nawamaki, Kenji Hattori
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Patent number: 4695636Abstract: Chromogenic azaphthalides of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of each other are hydrogen, C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or are cycloalkyl, benzyl or phenyl, or benzyl or phenyl which are substituted by halogen, nitro, cyano, lower alkyl, lower alkoxy or lower alkoxycarbonyl; or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached are a 5-membered or 6-membered heterocyclic radical and in particular pyrrolidinyl;X is hydrogen, halogen, lower alkyl, lower alkoxy, benzyl, phenyl, benzyloxy, phenoxy, or benzyl or benzyloxy which are substituted by halogen, nitro, lower alkyl or lower alkoxy;Y is hydrogen, unsubstituted or substituted alkyl or benzyl or acyl and in particular C.sub.6 -C.sub.Type: GrantFiled: February 4, 1986Date of Patent: September 22, 1987Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Ian J. Fletcher
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Patent number: 4689330Abstract: Novel substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines useful as anti-depressives, in the treatment of Parkinson's disease and in the treatment of diseases related with disturbed enterokinesia.Type: GrantFiled: February 27, 1986Date of Patent: August 25, 1987Assignee: Janssen Pharmaceutica N.V.Inventors: Frans E. Janssens, Theophilus T. J. M. Van Offenwert, Raymond A. Stokbroekx, Bernard R. Boar
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Patent number: 4675407Abstract: The invention relates to ring-substituted 4-azaphthalides of formula ##STR1## wherein Q is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl radical of the formula ##STR3## Y.sub.1 and Y.sub.2 are hydrogen, unsubstituted or substituted alkyl, acyl, or unsubstituted or substituted benzyl,Z.sub.1 and Z.sub.2 are hydrogen, lower alkyl or phenyl,R.sub.1 and R.sub.2, together with the nitrogen atom to which they are attached, are a 5- or 6-membered, preferably saturated, heterocyclic ring,X is hydrogen, halogen, alkyl, alkoxy, acyloxy, benzyl, phenyl, benzyloxy, phenoxy, substituted benzyl or benzyloxy, or is the --NT.sub.1 T.sub.2 group, in which T.sub.1 and T.sub.2 are hydrogen, lower alkyl, cycloalkyl, unsubstituted or substituted benzyl or is acyl, and T.sub.Type: GrantFiled: January 6, 1986Date of Patent: June 23, 1987Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Ian J. Fletcher
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Patent number: 4668790Abstract: Chromogenic dihydrofuropyridinones of the general formula ##STR1## wherein R.sub.1 and R.sub.2 independently of each other are hydrogen, C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or are cycloalkyl, benzyl or phenyl, or benzyl or phenyl which are substituted by halogen, nitro, lower alkyl or lower alkoxy; or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached are pyrrolidinyl;X is hydrogen, halogen, lower alkyl, lower alkoxy, benzyl, phenyl, benzyloxy, phenoxy, or benzyl or benzyloxy which are substituted by halogen, nitro, lower alkyl or lower alkoxy;Y is C.sub.6 -C.sub.9 alkyl;Z is hydrogen, lower alkyl or phenyl; andthe ring A is a pyridine radical andthe benzene nucleus B is unsubstituted or substituted by halogen, nitro, lower alkyl, lower alkoxy, amino or lower alkylamino.Type: GrantFiled: December 15, 1982Date of Patent: May 26, 1987Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Ian J. Fletcher
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Patent number: 4659717Abstract: This invention provides certain substituted dihydropyridines, their pharmaceutical formulations, and their use for causing vasodilation in mammals.Type: GrantFiled: August 21, 1985Date of Patent: April 21, 1987Assignee: Eli Lilly and CompanyInventor: James H. Wikel
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Patent number: 4659719Abstract: This invention relates to new 1,3-dihydro-6-[1-cyano-1-isopropyl-N-phenethyl-N-methyl-.omega.-aminoalkyl ]-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various substituents and to pharmaceutically acceptable salts of said derivatives, to a process for the preparation of the same, comprising reacting, in stoichiometric proportions, at 15.degree.-65.degree. C., in dimethylsulphoxide, a 6-(1-cyano-2-methyl-propyl)-7-hydroxy-furo-(3,4-c)-pyridine derivative with the appropriate N-methyl-N-phenethyl-.omega.-aminoalkyl choride and, finally, to a therapeutic composition of matter comprising as an essential ingredient therein any of said compounds in an amount effective to act as a calcium antagonist or a serotonin antagonist together with an appropriate diluent or carrier.Type: GrantFiled: October 21, 1985Date of Patent: April 21, 1987Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventor: Andre Esanu
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Patent number: 4650514Abstract: There are provided novel (2-imidazolin-2-yl)-thieno and furo compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: November 29, 1984Date of Patent: March 17, 1987Assignee: American Cyanamid CompanyInventors: Marinus Los, David W. Ladner, Barringtin Cross
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Patent number: 4647568Abstract: Hydroxytetrahydropyridinelactones of the formula ##STR1## in which R represents a phenyl, naphthyl, thienyl, furyl, pyrryl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, indolyl, benzimidazolyl, quinazolyl, quinoxalyl, thionaphthenyl, isothionaphthenyl, chromonyl, thiochromonyl, chromenyl, thiochromenyl, benzoxadiazolyl or benzthiadiazolyl radical, and the stated radicals may carry 1 to 3 identical or different substituents from the group comprising C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkinyl, C.sub.1 -C.sub.20 -alkoxy, fluorine, chlorine, bromine, iodine, trifluoromethyl, monofluoro-C.sub.1 -C.sub.10 -alkoxy, polyfluoro-C.sub.1 -C.sub.10 -alkoxy, hydroxyl, amino, mono-C.sub.1 -C.sub.10 -alkylamino, di-C.sub.1 -C.sub.10 -alkylamino, nitro, cyano, azido, carboxyl, carb-C.sub.1 -C.sub.10 -alkoxy, carboxamido, sulphonamido, SO.sub.Type: GrantFiled: November 20, 1984Date of Patent: March 3, 1987Assignee: Bayer AktiengesellschaftInventors: Klaus Gorlitzer, Ulrich Bartke, Siegfried Goldmann, Matthias Schramm, Gunter Thomas, Rainer Gross
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Patent number: 4639436Abstract: The invention includes certain 3,4,5-trihydroxypiperidine compounds, methods for their preparation, compositions containing said 3,4,5-trihydroxypiperidine compounds and methods for the use of said compounds and compositions.The subject matter of the invention is useful against diabetes, hyperlipaemia and adiposity as well as in animal nutrition.Type: GrantFiled: August 23, 1978Date of Patent: January 27, 1987Assignee: Bayer AktiengesellschaftInventors: Bodo Junge, Hans P. Krause, Lutz Muller, Walter Puls
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4-phenyl-tetrahydro-furano-pyridines and anti-depressant pharmaceutical compositions containing same
Patent number: 4636510Abstract: The invention relates to 4-phenyl-tetrahydro-furano-pyridines of the formulas ##STR1## wherein R.sup.1 to R.sup.5 are variously defined. The compounds of the invention are intended to be used as anti-depressants with, in particular, thymoleptic and central-stimulant properties.Type: GrantFiled: April 19, 1984Date of Patent: January 13, 1987Assignee: Boehringer Ingelheim KGInventors: Claus Schneider, Gerhard Walther, Karl-Heinz Weber, Wolf D. Bechtel, Karin Boke-Kuhn -
Patent number: 4632992Abstract: Processes and intermediates useful in the preparation of bronchodilator compounds of the formula ##STR1## wherein R is hydrogen, methyl or hydroxymethyl are described. Those compounds wherein R is H or CH.sub.3 have been found to have further utility as intermediates for pirbuterol (wherein R is hydroxymethyl).Type: GrantFiled: August 16, 1984Date of Patent: December 30, 1986Assignee: Pfizer Inc.Inventors: Berkeley W. Cue, Stephen S. Massett
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Patent number: 4608378Abstract: The present invention relates to novel compounds of the following formula: ##STR1## individual isomers and pharmaceutically acceptable acid addition salts thereof, wherein R.sub.1 is hydrogen, alkyl or phenyl-lower alkyl, in which the phenyl group may be substituted with halogen, lower alkyl or lower alkoxy; R.sub.2 is alkyl, alkenyl, alkynyl or phenyl-lower alkyl, in which the phenyl group may be substituted with halogen, lower alkyl or lower alkoxy; and R.sub.4 is hydrogen or alkyl.The invention moreover relates to methods for the preparation of the compounds of formula I, to novel intermediates, to pharmaceutical compositions containing same and to methods for the treatment of disorders, caused by malfunction of the acetylcholine (AcCh) or muscarinic system, by administering a non-toxic effective amount of a compound of the formula I.Type: GrantFiled: May 18, 1984Date of Patent: August 26, 1986Assignee: H. Lundbeck A/SInventors: Erik Falch, Povl Krogsgaard-Larsen, Per Sauerberg, Anne V. Christensen, Jens-Jorgen Larsen
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Patent number: 4602020Abstract: This invention relates to 1,3 - dihydro-6-aminomethyl-7-hydroxy-furo-(3,4-c)- pyridine derivatives of the general formula I ##STR1## wherein A.sub.1, A.sub.2, R.sub.1 and R.sub.2 represent various substituents, to pharmaceutically acceptable salts of such compounds, to a process for the preparation of compounds comprising reacting a 6-chloromethyl-7-benzoxy derivative of the general formula II ##STR2## with an excess of an amine derivative ##STR3## in a non-polar solvent, at a temperature not exceeding 20.degree. C., which leads to the desired substitution in position 6, followed by an acidic treatment to cleave the benzyl group and, finally to an anti-allergic composition of matter comprising, as an essential ingredient therein, an effective amount of one of these compounds together with an appropriate diluent or carrier.Type: GrantFiled: June 7, 1985Date of Patent: July 22, 1986Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventor: Andre Esanu
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Patent number: 4588733Abstract: 2-Phenylpyrano[2,3-b]pyridines are described herein. These compounds are active against a variety of viruses. A number of procedures can be used to prepare the compounds of this invention but, at some point, they would all make use of the cyclization of a (phenyl) (pyridyl)propanol or (phenyl) (pyridyl)propenol.Type: GrantFiled: October 19, 1984Date of Patent: May 13, 1986Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Thomas M. Bargar, John K. Daniel
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Patent number: 4588722Abstract: Novel N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives having antihistaminic properties which compounds are useful in the treatment of allergic diseases.Type: GrantFiled: October 15, 1984Date of Patent: May 13, 1986Assignee: Janssen Pharmaceutica N.V.Inventors: Frans E. Janssens, Joseph L. G. Torremans, Jozef F. Hens, Theophilus T. J. M. Van Offenwert
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Patent number: 4587343Abstract: The invention relates to chromogenic 3,3-bisindolyl-4-azaphthalides of the general formula ##STR1## wherein Y.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or is C.sub.1 -C.sub.12 acyl, benzyl or benzyl substituted halogen, nitro, lower alkyl or lower alkoxy,Y.sub.2 is C.sub.5 -C.sub.12 alkyl, preferably C.sub.6 -C.sub.9 alkyl, which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, andZ.sub.1 and Z.sub.2, each independently of the other, are hydrogen, lower alkyl or phenyl, and the rings A and B, each independently of the other, are unsubstituted or substituted by halogen, nitro, cyano, lower alkyl, lower alkoxy, lower alkoxycarbonyl, amino, mono-lower alkylamino or di-lower alkylamino.These compounds are particularly suitable for use as color formers in pressure-sensitive or heat-sensitive recording materials and produce fast, strong red or violet colorations.Type: GrantFiled: May 1, 1984Date of Patent: May 6, 1986Assignee: Ciba-Geigy CorporationInventors: Davor Bedekovic, Ian J. Fletcher
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Patent number: 4585776Abstract: The invention relates to new 1,3-dihydro-4-chloro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the formula ##STR1## to a preparation process of the same from the corresponding non 4-substituted derivatives and to pharmaceutical compositions useful in selective diuresis and lowering of blood pressure wherein said derivatives are the active ingredients.Type: GrantFiled: October 16, 1984Date of Patent: April 29, 1986Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventor: Andre Esanu
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6-substituted furo-(3,4-c)-pyridine derivatives and anti-depressant compositions containing the same
Patent number: 4581362Abstract: This invention relates to new 1,3-dihydro-6-(1-hydroxy-2-dimethylaminomethyl-allyl)-7-hydroxy-furo-(3,4- c)-pyridine derivatives of the general formula: ##STR1## wherein, each of A.sub.1 and A.sub.2 independently, represents various substituents, to a process for the preparation of these compounds comprising reacting a 6-formyl-7-benzyloxy-furo-(3,4-c)-pyridine derivative of the general formula II ##STR2## with 1-dimethylaminomethyl-vinylmagnesium bromide at the boil, in a non polar solvent and hydrolyzing the 7-benzyloxy group and to a therapeutic composition of matter, comprising as an essential ingredient therein, at least one of these compounds. The compounds according to the invention are of interest for their therapeutic activity, principally as anti-depressive agents.Type: GrantFiled: January 23, 1985Date of Patent: April 8, 1986Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventor: Andre Esanu -
Patent number: 4581363Abstract: This invention relates to 1,3-dihydro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula I ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various hydrocarbon groups and therapeutically acceptable addition salts thereof; to a process for the preparation of the same comprising oxidizing the secondary alchol .alpha..sup.4, 3-o-isopropylidene-1-methyl-5-(1-hydroxy-1-A.sub.1)-methyl pyridine by any usual technique, reacting the resultant ketone with a compound of the general formula XA.sub.2 wherein X stands for Br or I in the presence of magnesium in diethyl ether at the boil and treating the resultant tertiary alcohol with an acidic agent to provoke breaking of the isopropylidene ring and 3,4-cyclization; and to pharmaceutical compositions containing these derivatives.Type: GrantFiled: March 26, 1984Date of Patent: April 8, 1986Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)Inventor: Andre Esanu
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Patent number: 4569939Abstract: This invention relates to new 1,3-dihydro-6-vinyl-7-hydroxy-furo-(3,5-c)-pyridine derivatives of the general formula: ##STR1## wherein each of A.sub.1 and A.sub.2 independently represents various hydrocarbon substituents, to a process for the preparation of these compounds from the corresponding 7-chloromethyl derivative and to pharmaceutical composition containing them. The compounds are useful as diuretics.Type: GrantFiled: November 5, 1984Date of Patent: February 11, 1986Assignee: Societe de Conseils de Recherches et d'Applications ScientifiquesInventor: Andre Esanu
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Patent number: 4569938Abstract: This invention relates to new 1,3-dihydro-6-methyl-furo-(3,4-c)-pyridine derivatives of the general formula: ##STR1## wherein, each of A.sub.1 and A.sub.2 represents various hydrocarbon groups, to pharmaceutically acceptable salts of them, to a process for the preparation of said derivatives from the corresponding 6-hydroxy compounds, treated by ethyl bromoacetate and then hydrolyzed. The invention further provides pharmaceutical compositions wherein said derivatives are used as active ingredients. The compounds are useful as diuretics, in lowering blood pressure and as antihistaminics.Type: GrantFiled: November 5, 1984Date of Patent: February 11, 1986Assignee: Societe de Conseils de Recherches et d'Applications ScientifiquesInventor: Andre Esanu
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Patent number: 4567268Abstract: A facile process for the preparation of certain tetrahydrofuro[3,4-b]pyridines is described. The compounds have pharmacological properties useful in the study and treatment of cardiovascular diseases.Type: GrantFiled: April 3, 1984Date of Patent: January 28, 1986Assignee: Merck & Co., Inc.Inventor: Steven D. Young
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Patent number: 4564679Abstract: The chromogenic azaphthalide compounds of the invention are of the formula: ##STR1## wherein A is a pyridine ring; R.sub.1 is hydrogen atom or alkyl radicals of from one to 4 carbon atoms; X is hydrogen atom, alkyl radicals of from one to 2 carbon atoms or alkoxy radicals of from one to 2 carbon atoms; R.sub.2 is alkyl radicals of from one to 2 carbon atoms or phenyl radical; R.sub.3 is hydrogen atom or alkyl radicals of from one to 8 carbon atoms.These compounds are particularly suitable for use in providing high quality pressure- or heat-sensitive copying sheets.Type: GrantFiled: June 16, 1982Date of Patent: January 14, 1986Assignee: Yamada Chemical Co., Ltd.Inventors: Yoshiharu Fujino, Hajime Kawai, Yasushi Nakai, Katsuhiko Tsunemitsu
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Patent number: 4540785Abstract: Hydroquinones of the formula ##STR1## wherein X is the residue of a 5- or 6-membered ring, R.sub.1 is hydrogen, alkyl or aryl, R.sub.1,R.sub.3, R.sub.4 and R.sub.5 are hydrogen or alkyl and R.sub.6 is hydrogen or a group of the formula ##STR2## wherein X and R.sub.1 are as defined above, are of use as protected developing agents in photographic silver halide material.Type: GrantFiled: November 8, 1983Date of Patent: September 10, 1985Assignee: Ciba-Geigy AGInventor: Norman A. Smith
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Patent number: 4532248Abstract: 1,4-Dihydropyridines of the formula ##STR1## in which n is 0,1 or 2, andR.sup.1 to R.sup.7 can have a wide variety of meanings, which possess inotropic action, and many of which are new, are useful in increasing the influx of Ca.sup.++ into cells, particularly in combatting coronary and vascular diseases, hypertension swelling in the mucous membranes and diseases involving increased blood sugar or an incorrect salt and fluid balance.Type: GrantFiled: July 14, 1982Date of Patent: July 30, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Franckowiak, Horst Boshagen, Friedrich Bossert, Siegfried Goldmann, Horst Meyer, Egbert Wehinger, Jurgen Stoltefuss, Matthias Schramm, Gunter Thomas, Robertson Towart
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Patent number: 4517183Abstract: The present invention provides pharmaceutical compositions containing N-substituted aziridine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein X is a carboxyl, a cyano, an alkoxycarbonyl or an optionally substituted carbamoyl radical, R is a hydrogen atom, an aliphatic hydrocarbon radical which is saturated or can contain one or more unsaturations and can be substituted one or more times by halogen, alkoxy, hydroxyl, dialkylamino, dialkylaminoxy, cycloalkylamino, acylamino, acyl, nitro, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxyl, alkoxycarbonyl or carbamoyl or by cycloalkyl or cycloalkenyl radicals optionally carrying alkyl, alkoxy or alkoxycarbonyl radicals, optionally interrupted by hetero atoms and optionally bridged, or by an aryl, hetaryl, aryloxy, arylthio, acyloxy, alkoxycarbonylamino or isothioureido radical, or R is a cycloalkyl or cycloalkenyl radical optionally substituted by alkyl, alkoxy or oxo groups, optionally interrupted by hetero atoms and optionally briType: GrantFiled: May 17, 1983Date of Patent: May 14, 1985Assignee: Boehringer Mannheim GmbHInventors: Elmar Bosies, Wolfgang Kampe, Max Thiel, Uwe Bicker, Dietmar Boerner
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Patent number: 4508897Abstract: Chromogenic azaphthalides of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of each other are hydrogen, C.sub.1 -C.sub.12 alkyl which is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, or are cycloalkyl, benzyl or phenyl, or benzyl or phenyl which are substituted by halogen, nitro, cyano, lower alkyl, lower alkoxy or lower alkoxycarbonyl; or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached are a 5-membered or 6-membered heterocyclic radical and in particular pyrrolidinyl;X is hydrogen, halogen, lower alkyl, lower alkoxy, benzyl, phenyl, benzyloxy, phenoxy, or benzyl or benzyloxy which are substituted by halogen, nitro, lower alkyl or lower alkoxy;Y is hydrogen, unsubstituted or substituted alkyl or benzyl or acyl and in particular C.sub.6 -C.sub.Type: GrantFiled: June 7, 1983Date of Patent: April 2, 1985Assignee: Ciba Geigy CorporationInventors: Davor Bedekovic, Ian J. Fletcher
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Patent number: 4497808Abstract: The present invention relates to novel N-oxide compounds that have cardiovascular properties, especially antihypertensive activity, and that correspond to the formula ##STR1## in which Py represents an unsubstituted or substituted N-oxidopyridyl radical, R.sub.1 represents hydrogen or unsubstituted or substituted lower alkyl, one of the radicals R.sub.2 and R.sub.3 represents lower alkyl and the other represents hydrogen; lower alkyl; lower alkyl containing free, etherified or esterified hydroxy, oxo, functionally modified carboxy or free or substituted amino or imino; functionally modified carboxy; or free or substituted amino, it being possible for an amino group R.sub.2 or R.sub.3 to be bonded to a lower alkyl radical R.sub.1 or, if R.sub.2 or R.sub.3 represents, for example, hydroxy-lower alkyl, for this hydroxy-lower alkyl, together with the adjacent acyl radical Ac.sub.1 or Ac.sub.Type: GrantFiled: December 27, 1982Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventors: Markus Zimmermann, Hans Kuhnis
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Patent number: 4480098Abstract: Thienopyridines and furopyridines react at the 2-position with non-nucleophilic alkali metal bases to give alkali metal thieno(furo)pyridine salts.Type: GrantFiled: November 12, 1982Date of Patent: October 30, 1984Assignee: Eli Lilly and CompanyInventors: Richard E. Koehler, John A. Webber
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Patent number: 4477276Abstract: Compounds of the formula ##STR1## wherein R is halogen, CF.sub.3, NO.sub.2, CN, Alkyl or alkoxy, n is 0 to 3 X is O, S, NH or N-Alkyl, Y is O, S, SO, SO.sub.2, NH or N-Alkyl, R.sub.1 is H or alkyl and Z is carboxy or hydroxymethyl or functional derivatives of these groups, are valuable herbicides and growth regulators.Type: GrantFiled: September 22, 1982Date of Patent: October 16, 1984Assignee: Hoechst AktiengesellschaftInventors: Lothar Willms, Reinhard Handte, Hilmar Mildenberger, Klaus Bauer, Hermann Bieringer, Helmut Burstell
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Patent number: 4439607Abstract: The present invention relates to a process for the preparation of substituted pyridine and quinoline-2,3-dicarboxylic anhydrides, and the herbicidally effective imidazolinyl pyridine and quinoline compounds prepared therefrom.Type: GrantFiled: May 25, 1982Date of Patent: March 27, 1984Assignee: American Cyanamid CompanyInventor: Thomas W. Drabb
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Patent number: 4412996Abstract: The esters of pyridoxine and of isopropylidene pyridoxine with 1-(p-chlorobenzoyl)-2-methyl-5-methoxy-indol-3-acetic acid and 5-(2,4-difluorophenyl)-salicylic acid are essentially endowed with the same activities of the corresponding acids and are less toxic and gastrolesive, whereby the therapeutical index is remarkably improved. For the preparation of these compounds the chloride of the acid is reacted with isopropylidene pyridoxine, followed by a hydrolysis to obtain the corresponding pyridoxine derivative.Type: GrantFiled: October 20, 1981Date of Patent: November 1, 1983Assignee: Crinos Farmacologica SpaInventor: Alberto Reiner
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Patent number: 4383998Abstract: This invention relates to new 1,3-dihydro-6-methyl-7-hydroxy-furo-(3,4-c)-pyridine derivatives of the general formula ##STR1## wherein A< represents a group of the formula --(CH.sub.2).sub.n --, n being an integer of from 1 to 5, or a homocyclic or heterocyclic group, and R represents a hydrogen, chlorine or fluorine atom, a trifluoromethyl group, an alkyl group having from 1 to 5 carbon atoms, an alkoxy group having from 1 to 5 carbon atoms, a alkylthio group having from 1 to 5 carbon atoms, a dialkylaminoalkoxy group in which the alkyl groups each have from 1 to 5 carbon atoms and the alkoxy group has from 1 to 5 carbon atoms or a N-pyrolidinyl-alkoxy group in which the alkoxy group has from 1 to 5 carbon atoms to a process for the preparation of the same by refluxing .alpha..sup.Type: GrantFiled: January 8, 1982Date of Patent: May 17, 1983Assignee: Societe de Conseils de Recherches et D'Applications ScientifiquesInventor: Andre Esanu
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Patent number: 4376862Abstract: An intermediate product of the formula ##STR1## is reacted with NaOH or KOH at 50.degree.-110.degree. to produce 4-amino-6-hydroxy-3-aryl-isoxazolo [5,4-b] pyridine-5-carbonitrile.Type: GrantFiled: November 25, 1981Date of Patent: March 15, 1983Assignee: Lonza Ltd.Inventors: Hans Junek, Burkhard Thierrichter
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Patent number: 4375544Abstract: Aromatic-.alpha.-halo-{b} fused pyridines are made by reacting an aromatic acetamide, acid halide and amide in particular proportions, with the acid halide always in excess. The process permits the production of compounds having a wide range of substituents, that are new compounds, and that are of value as intermediates in the synthesis of, for instance, pharmaceutical compounds.Type: GrantFiled: June 8, 1979Date of Patent: March 1, 1983Assignee: Croda Synthetic Chemicals LimitedInventors: Otto Meth-Cohn, Brahma Narine
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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: 4353910Abstract: Carbamoyl derivatives of 4,5,6,7-Tetrahydroisoxazolo[5,4-c] Pyridine-3-one, and method of preparation, pharmaceutical compositions thereof, and methods of treatment of GABA-system malfunctions therewith, are all disclosed.Type: GrantFiled: November 27, 1981Date of Patent: October 12, 1982Assignee: Kefalas A/SInventor: Jens K. Perregaard
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Patent number: 4350815Abstract: Process for the production of 4,6-diamino-5-cyano-3-aryl-isoxazole [5,4-b] pyridines having the formula: ##STR1## wherein (a) R.sup.1 and R.sup.2 are --H or (b) R.sup.1 is --Cl and R.sup.2 is --H, or (c) R.sup.1 is --CH.sub.3 and R.sup.2 is --H or (d) R.sup.1 is --NO.sub.2 and R.sup.2 is --H, or (e) R.sup.1 is --H and R.sup.2 is --NO.sub.2. 2-Amino-1-propane-1,1,3-tricarbonitrile having the formula: ##STR2## is reacted with a benzohydroxamino acid chloride having the formula: ##STR3## wherein R.sup.1 and R.sup.2 have the same meaning as above, in the presence of a strong base in at least a molar quantity.Type: GrantFiled: November 21, 1980Date of Patent: September 21, 1982Assignee: Lonza Ltd.Inventors: Hans Junek, Burkhard Thierrichter
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Patent number: 4350816Abstract: Process for the production of 4-amino-6-hydroxy-3-aryl isoxazolo [5,4-b] pyridine-5-carbonitriles having the formula: ##STR1## wherein R (a) is --H, (b) is --Cl or (c) is --CH.sub.3. 3-Amino-2,4,dicyanocrotonic acid methyl ester having the formula: ##STR2## is reacted with a benzohydroxyamino acid chloride having the formula: ##STR3## wherein R has the same meaning as above, in the presence of a strong base (at least molar) at a temperature of up to 10.degree. C. to produce, as an intermediate, the corresponding 3-amino-2-cyano-3-(5-amino-3-aryl-isoxazol-4-yl)-acrylic acid methyl ester having the formula ##STR4## wherein R has the same meaning as above. The intermediate product is reacted in excess diluted NaOH or KOH at a temperature of 50.degree. to 110.degree. C. to produce the corresponding 4-amino-6-hydroxy-3-aryl-isoxazolo [5,4-b] pyridine-5-carbonitrile.Type: GrantFiled: November 21, 1980Date of Patent: September 21, 1982Assignee: Lonza Ltd.Inventors: Hans Junek, Burkhard Thierrichter