Additional -coo- Group Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/321)
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Patent number: 5912351Abstract: The subject invention provides anhydrous 1,4-dihydropyridines and salts thereof, and a method for preparing them. The 1,4-dihydropyridines have Formula I: ##STR1## wherein: Ph is phenyl,Ar is: 2-nitrophenyl, 3-nitrophenyl, 2,3-dichlorophenyl or benzofurazan-4-yl,A is a branched chain alkylene radical having from 2 to 6 carbon atoms,R is a straight or branched chain alkyl radical having from 1 to 6 carbon atoms, optionally mono-substituted by an alkoxy substituent having from 1 to 6 carbon atoms,R.sub.1 is hydrogen, hydroxy, or an alkyl radical having from 1 to 4 carbon atoms, andR.sub.2 is hydrogen, or methyl.Type: GrantFiled: May 10, 1996Date of Patent: June 15, 1999Assignee: Recordati, S.A. Chemical and Pharmaceutical CompanyInventors: Amedeo Leonardi, Gianni Motta
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Patent number: 5856346Abstract: Compounds of the general formula ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from the group consisting of hydrogen, chloro, bromo, nitro, cyano, trifluoromethyl, and R.sub.3 and R.sub.4 are independently selected from straight or branched lower (1-5 carbon atoms) alkyl groups, and including all optical isomers, provided that when R.sub.3 is methyl and R.sub.4 is tert.-butyl, then R.sub.1 /R.sub.2 are not hydrogen/hydrogen, hydrogen/2'-trifluormethyl, 2'-chloro/3'-chloro, and when R.sub.3 is methyl and R.sub.1 /R.sub.2 is hydrogen/3'-nitro, then R.sub.4 are not methyl, ethyl, propyl, iso-propyl, tert.-butyl, processes for their preparation, pharmaceutical preparations containing them and the use of the compounds in lowering the blood pressure.Type: GrantFiled: December 14, 1994Date of Patent: January 5, 1999Assignee: Astra AktiebolagInventors: Kjell Hjalmar Andersson, Margareta Nordlander, Rolf Christer Westerlund
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Patent number: 5763614Abstract: 1,4-dihydropyridine derivatives and optically active 1,4-dihydropyridine derivatives with the following formula, having vasodilating activity based on calcium antagonism, and PAF antagonism, and methods of producing the same are disclosed: ##STR1## wherein (*) indicates a chiral center in the case of the optically active 1,4-dihydropyridine derivatives.Type: GrantFiled: June 10, 1994Date of Patent: June 9, 1998Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Akiyoshi Kadoiri, Yasuko Konagai, Tetsuaki Yamaura, Noriko Kase
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Patent number: 5760238Abstract: Disclosed are 1,4-dihydropyridine derivatives represented by the general formula (I) and salts thereof, as well as optical active 1,4-dihydropyridine derivatives represented by the general formula (II) and salts thereof which are obtained from the derivative by biochemical reactions using microorganisms or enzymes and useful as preventive and therapeutic agents for ischemic heart diseases and hypertension. ##STR1## (wherein x and Y are H, NO.sub.2, CN, halogen; R.sup.1 and R.sup.2 are H, CHO, substituted alkylcarbonyl, crotonyl, cinnamoyl, alkoxycarbonyl, aryloxycarbonyl, benzyloxycarbonyl, carboxybenzoyl, or R.sup.1 and R.sup.2 taken together represent phthaloyl; n is an integer of 1 to 3).Type: GrantFiled: February 25, 1997Date of Patent: June 2, 1998Assignee: Mercian CorporationInventors: Kunio Isshiki, Naoki Matsumoto, Takashi Nakashima, Kazuyuki Dobashi, Takurou Tsuruta, Takeo Yoshioka
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Patent number: 5760239Abstract: There is provided an improved method for the conversion of 5,6-dicarboxyl-3-pyridylmethyl ammonium halide to 5-(alkoxymethyl)pyridine-2,3-dicarboxylate salt via a single step closed reaction with the appropriate alcohol and a base at a temperature of about 120.degree.-180.degree. C.The product pyridinedicarboxylate salt is an important intermediate in the manufacture of pyridine imidazolinone herbicidal agents.Type: GrantFiled: July 16, 1997Date of Patent: June 2, 1998Assignee: American Cyanamid CompanyInventor: Wen-Xue Wu
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Patent number: 5750707Abstract: A method for the separation of R-(+)- and S-(-)-isomers of amlodipine (I) from mixtures thereof, which comprises the reaction of the mixture of isomers with either L- or D-tartaric acid in an organic solvent containing sufficient dimethyl sulphoxide (DMSO) for the precipitation of, respectively, a DMSO solvate of an L-tartrate salt of R-(+)-amlodipine, or a DMSO solvate of a D-tartrate salt of S-(-)-amlodipine.Type: GrantFiled: September 18, 1996Date of Patent: May 12, 1998Assignee: Pfizer Inc.Inventor: Peter Lionel Spargo
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Patent number: 5731333Abstract: 4-Phenyl-3-substituted 1,4-dihydropyridine esters are prepared by reaction of benzaldehydes with ketoesters and enamines, if appropriate with isolation of the ylidene intermediate products, or by esterification of corresponding dihydropyridinecarboxylic acids with alcohols.The new 4-phenyl-3-substituted 1,4-dihydropyridine esters can be employed as active compounds in medicaments for the treatment of the central nervous system, in particular as cerebral therapeutics.Type: GrantFiled: December 2, 1994Date of Patent: March 24, 1998Assignee: Bayer AktiengesellschaftInventors: Heinrich Meier, Wolfgang Hartwig, Bodo Junge, Rudolf Schohe-Loop, Zhan Gao, Bernard Schmidt, Maarten de Jonge, Teunis Schuurman
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Patent number: 5723618Abstract: The invention relates to a novel process to prepare 1,4-dihydropyridines and in particular amlopidine and in novel intermediates obtained during the synthesis of the 1,4-dihydropyridines which have potential activity as antihypertensive agents.Type: GrantFiled: October 10, 1996Date of Patent: March 3, 1998Assignee: Apotex, Inc.Inventors: Regis Chung Soon Hin Leung-Toung, Khashayar Karimian, Tim Fat Tam
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Patent number: 5696139Abstract: The present invention provides S-enantiomers of 1,4-dihydropyridines useful for the treatment of heart failure, preparation of compositions thereof and a method for the treatment of hypertension and heart failure comprising administration of these compounds.Type: GrantFiled: May 9, 1996Date of Patent: December 9, 1997Assignee: Recordati S.A., Chemical and Pharmaceutical CompanyInventors: Amedeo Leonardi, Gianni Motta, Rodolfo Testa
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Patent number: 5668288Abstract: Carboxy-terminated polyester ionomers useful for bioresorbable implant construction are described. They comprise biocompatible salts or partial salts of mono- or bis-carboxy-terminated polyesters.Type: GrantFiled: April 16, 1996Date of Patent: September 16, 1997Assignee: DePuy Orthopaedics, Inc.Inventors: Robson F. Storey, Z. David Deng, Todd P. Glancy, Dale R. Peterson
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Patent number: 5665740Abstract: The present invention relates to the new compound rac-isopropyl 2-methoxyethyl 4-(2-chloro-3-cyano-phenyl)1,4 -dihydro-2,6-dimethylpyridine-3,5-dicarboxylate and its pure enantiomers, processes for their preparation and their use as medicaments, in particular for the treatment of cerebral and neuronal disorders, and a new intermediate for their preparation.Type: GrantFiled: December 2, 1994Date of Patent: September 9, 1997Assignee: Bayer AktiengesellschaftInventors: Heinrich Meier, Wolfgang Hartwig, Bodo Junge, Rudolf Schohe-Loop, Zhan Gao, Bernard Schmidt, Maarten de Jonge, Teunis Schuurman
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Patent number: 5658934Abstract: The invention relates to new aryl-substituted alkoxycarbonyl-1,4-dihydropyridine-5-carboxylic acid esters, processes for their preparation and their use in medicaments, in particular as agents having a cerebral action.Type: GrantFiled: December 5, 1994Date of Patent: August 19, 1997Assignee: Bayer AktiengesellschaftInventors: Heinrich Meier, Wolfgang Hartwig, Bodo Junge, Ulrich Niewohner, Rudolf Schohe-Loop, Zhan Gao, Bernard Schmidt, Maarten de Jonge, Teunis Schuurman
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Patent number: 5635395Abstract: (4R)-3-(Substituted aminoalkyl)oxycarbonyl-1,4-dihydro-2,6-dimethyl-4-(nitrophenyl)pyridine-5- carboxylic acids can be prepared efficiently, by reacting bis(substituted aminoalkyl) 1,4-dihydro-2,6-dimethyl-4-(nitrophenyl)pyridine-3,5-dicarboxylates with a microorganism capable of asymmetric hydrolysis and belonging to the genus Streptomyces, the genus Paecilomyces, the genus Botryodioplodia, the genus Alternaria or the genus Helminthosporium, or a treated product thereof. The compounds are extremely useful as important intermediates for preparation of pharmaceuticals useful for the prevention and treatment of angina pectoris, hypertension, etc.Type: GrantFiled: February 21, 1995Date of Patent: June 3, 1997Assignees: Mercian Corporation, Taisho Pharmaceutical Co., Ltd.Inventors: Kunio Isshiki, Takashi Nakashima, Takeo Yoshioka, Hiroshi Tsunekawa, Takashi Adachi, Tomomi Ota
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Patent number: 5633383Abstract: The invention relates to a process which comprises the crystallization of a calcium salt of chiral (R or S) lactic acid esterified with a racemic dihydropyridine.Type: GrantFiled: April 27, 1995Date of Patent: May 27, 1997Assignee: Laboratoire L. LafonInventor: Philippe Laurent
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Patent number: 5622978Abstract: Pharmaceutical preparations for the oral administration of dihydropyridines in beverage form are described.These preparations are characterised in that they contain a coprecipitate of essentially amorphous dihydropyridine with a suitable pharmacologically acceptable polymer. The corresponding preparation processes are also described.Type: GrantFiled: September 29, 1995Date of Patent: April 22, 1997Assignee: Bayer S.p.A.Inventors: Silvana Ciceri, Gilberto Dondi, Paolo Scurati
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Patent number: 5614635Abstract: The present invention provides an improved method for the preparation of pyridine-2,3-dicarboxylic acids by the continuous oxidation of substituted quinolines.Type: GrantFiled: August 16, 1995Date of Patent: March 25, 1997Assignee: American Cyanamid CompanyInventor: Paul E. Miller
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Patent number: 5606066Abstract: Light-activable 1-(2-nitrobenzyl) substituted 1,4-dihydropyridines are provided, which are important intermediates for releasing highly effective 1,4-dihydropyridines. A process for preparing the same is also provided. The compounds may be used for facilitating and observing biological, physiological and pharmacological activities. The invention provides an approach for the synthesis of Ca-agonistic and Ca-antagonistic 1,4-dihydropyrimidines for monitoring calcium channel activity.Type: GrantFiled: May 1, 1995Date of Patent: February 25, 1997Inventors: Siegfried Goldmann, Martin Bechem
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Patent number: 5599824Abstract: The invention relates to pharmaceutical preparations, containing a specific crystal modification (subsequently called "modification II") of isopropyl-(2-methoxyethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (nimodipine) and to a process for its preparation.Type: GrantFiled: January 30, 1995Date of Patent: February 4, 1997Assignee: Bayer AktiengesellschaftInventors: Alfons Grunenberg, Ahmed Hegasy, Wolfgang M uck, Gerhard Franckowiak, Rango-Rao Kanikanti
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Patent number: 5559139Abstract: The invention relates to the new dimethyl 4-(4-chloro-3-trifluoromethylphenyl) -1-cyclopropyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, a process for its preparation and its use as a medicament in ischaemic diseases which are associated with disorders of the microcirculation. This action can occur both in the peripheral and in the cerebral vascular system.Type: GrantFiled: July 13, 1993Date of Patent: September 24, 1996Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Hartmund Wollweber, Bruno Rosen, Siegfried Zaiss, Siegfried Goldmann
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Patent number: 5554621Abstract: A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of nitrogen heterocyclic derivatives of 4-phenyl-1,4-dihydropyridines of Formula (I). ##STR1## As antagonists of NPY-induced feeding behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.Type: GrantFiled: June 7, 1995Date of Patent: September 10, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Graham S. Poindexter, Marc Bruce, Graham Johnson, Karen LeBoulluec, Jeffrey W. Noonan
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Patent number: 5545835Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pylidinedicarboxylic acids.Type: GrantFiled: November 4, 1994Date of Patent: August 13, 1996Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5527921Abstract: Peroxycarboxylic ester photoinitiators derived from aromatic nitrogen containing heterocyclic carboxylic acids are described. The heterocyclic aromatic ring may contain additional nitrogen atoms, be fused with another aromatic ring system, be substituted with an additional peroxycarboxylic ester group and/or be substituted with an electron group having a Hammett sigma value greater than 0.1. The peroxycarboxylic ester photoinitiators have been found to be useful in photopolymerizable compositions and photosensitive elements.Type: GrantFiled: March 21, 1995Date of Patent: June 18, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventor: Jeanne E. Haubrich
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Patent number: 5519012Abstract: Novel inclusion complexes of racemic 1,4-dihydropyridines and enantiomers thereof of the formula ##STR1## wherein R represents a phenyl group, substituted with nitro, trifluoromethyl, difluoromethoxy group or with one or two halo atoms (especially chlorine),R.sub.1 and R.sub.2, if the same, represent methyl groups and if one of them has the meaning of a 2-aminoethoxymethyl or cyano group, the other represents a methyl group,R.sub.3 and R.sub.4, if different, stand each time for a hydrogen, linear or branched C.sub.1 -C.sub.6 -alkyl, 2-methoxyethyl, 1-(phenylmethyl)-3-piperidinylphenyl, styryl, furyl, piperidino, 4-diphenylmethyl-1-piperazinylethyl, 5-phenyl-3-pirazolyloxy, 1-phenyl-methyl-3-pyrrolidinyl group or a group of the formula ##STR2## or, if the same, stand each time C.sub.1 -C.sub.4 alkyl group, and of acid addition salts thereof with methyl-.beta.-cyclodextrin, hydroxy-ethyl-.beta.-cyclodextrin or hydroxypropyl-.beta.Type: GrantFiled: December 16, 1994Date of Patent: May 21, 1996Assignee: LEK, tovarna farmacevtskih in kemicnih izdelkov, d.d., LjubljanaInventors: Darja Fercej-Temeljotov, Janko Zmitek, Breda Husu-Kovacevic, Sonja Kotnik, Zdenka Jerala-Strukelj
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Patent number: 5491154Abstract: Pharmaceutical preparations for the oral administration of dihydropyridines in beverage form are described.These preparations are characterized in that they contain a coprecipitate of essentially amorphous dihydropyridine with a suitable pharmacologically acceptable polymer. The corresponding preparation processes are also described.Type: GrantFiled: July 29, 1993Date of Patent: February 13, 1996Assignee: Bayer S.p.A.Inventors: Silvana Ciceri, Gilberto Dondi, Paolo Scurati
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Patent number: 5475111Abstract: The invention relates to a process for the preparation of optically pure 1,4-dihydropyridinemonocarboxylic acids of the formula I ##STR1## in which the substituents have the meanings mentioned in the description.Type: GrantFiled: August 17, 1993Date of Patent: December 12, 1995Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventor: Bernhard Kohl
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Patent number: 5468746Abstract: Compounds of the formula ##STR1## (wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, m and n have the meanings given in the description), their preparation and pharmaceutical compositions containing them.The compounds of formula I are active on the cardiovascular system as antivasospastics, antiangina agents, antihypertensives and vasodilators.Type: GrantFiled: June 21, 1991Date of Patent: November 21, 1995Assignee: Zambon Group S.p.A.Inventors: Cesare Casagrande, Stefania Montanari, Francesco Santangelo
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Patent number: 5444077Abstract: An ameliorant of cerebral circulation which contains 2-carbamoyloxymethyl-4-(2,3-dichlorophenyl )-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester as an active ingredient.Type: GrantFiled: July 29, 1994Date of Patent: August 22, 1995Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Masaru Nishikibe, Kazuo Kamei, Jun Nagura, Takahiro Fukuroda
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Patent number: 5439925Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function. Use is in human and veterinary medicine and in cosmetics.Type: GrantFiled: December 16, 1993Date of Patent: August 8, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, Willliam R. Pilgrim
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Patent number: 5438145Abstract: There is disclosed a process for the preparation of 3-ethyl 5-methyl (.+-.) 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyri dine-dicarboxylate monobenzenesulphonate (amlodipine benzenesulphonate) of formula ##STR1## wherein 3-ethyl 5-methyl (.+-.) 2-[2-(N-tritylamino)-ethoxymethyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl -3,5-pyridinecarboxylate is reacted with benzenesulphonic acid in a methanolic or an aqueous methanolic medium at a temperature from 20.degree. C. to the reflux temperature and the title compound is isolated and purified.Amlodipine benzene sulphonate is a valuable anti-ischaemic and anti-hypertensive agent.Type: GrantFiled: August 25, 1994Date of Patent: August 1, 1995Assignee: LEK, tovarna farmecevtskih in kemicnih izdelkovInventors: Borut Furlan, Anton Copar, Alenka Jeriha
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Patent number: 5438144Abstract: The invention relates to the use of 1,4-dihydropyridines having calcium antagonistic action, in particular of nimodipine, for the preparation of medicaments for controlling damage to peripheral nerves which is caused by diabetes.Type: GrantFiled: July 9, 1993Date of Patent: August 1, 1995Assignee: Troponwerke GmbH & Co. KGInventors: Jorg Traber, Willem H. Gispen
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Patent number: 5432185Abstract: Improving circulation, with minimal effect on blood pressure, using N-alkylated 1,4-dihydropyridines of the formula ##STR1## in which R.sup.1 represents hydrogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, halogen or methyl,R.sup.2 represents hydrogen, halogen, nitro, hydroxyl, trifluoromethyl or methyl,R.sup.3 represents hydrogen or cyano, orR.sup.2 and R.sup.3 together form a fused benzo ring,R.sup.4 and R.sup.5 are identical or different and represent straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by alkoxy having up to 4 carbon atoms, andR.sup.6 represents straight-chain or branched alkyl having up to 10 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms.Many of the compounds are new.Type: GrantFiled: May 21, 1993Date of Patent: July 11, 1995Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Hartmut Wollweber, Bruno Rosen, Siegfried Zaiss, Siegfried Goldmann
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Patent number: 5424321Abstract: Compounds having both calcium antagonist and antioxidant activity are disclosed. The compounds are useful in preventing or alleviating damage to tissues at the cellular level. Methods of treatment which employ these properties of the compounds and corresponding pharmaceutical compositions are also disclosed.Type: GrantFiled: December 8, 1993Date of Patent: June 13, 1995Assignee: Alcon Laboratories, Inc.Inventors: Mark R. Hellberg, George Barnes, Robert J. Collier, Jr.
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Patent number: 5410062Abstract: There are provided crystalline substituted-2,3-dicarboxypyridinium nitrate salts, the preparation thereof and the use thereof in the isolation and purification of important substituted pyridinedicarboxylic acid herbicide intermediates.Type: GrantFiled: February 2, 1994Date of Patent: April 25, 1995Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5389654Abstract: There is disclosed a process for the preparation of 3-ethyl 5-methyl (.+-.) 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyri dine-dicarboxylate monobenzenesulphonate (amlodipine benzenesulphonate) of formula ##STR1## wherein 3-ethyl 5-methyl (.+-.) 2-[2-(N-tritylamino)-ethoxymethyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl -3,5-pyridinedicarboxylate is reacted with benzenesulphonic acid in a methanolic or an aqueous methanolic medium at a temperature from 20.degree. C. to the reflux temperature and the title compound is isolated and purified.Amlodipine benzene sulphonate is a valuable anti-ischaemic and anti-hypertensive agent.Type: GrantFiled: November 10, 1993Date of Patent: February 14, 1995Assignee: LEK, tovarna, farmacevtskih in Kemicnih . . .Inventors: Borut Furlan, Anton Copar, Alenka Jeriha
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Patent number: 5389644Abstract: The compounds are 2,4-disubstituted 3-ethoxycarbonyl 5-methoxycarbonyl 6-methyl 1,4-dihydropyridines in their dextrorotatory form, useful to potentiate the activity of cytotoxic agents and to increase the sensitivity of tumor cells to antitumor agents.A compound disclosed is d-2-{[2-(2-(N-p-nitrobenzylamino)ethoxy)ethoxy]methyl}-4-(2,3-dichlorophen yl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine.Type: GrantFiled: February 4, 1993Date of Patent: February 14, 1995Assignee: Adir et CompagnieInventors: Jean-Louis Peglion, Ghanem Aasssi, Alain Pierre, Laurence Kraus-Berthier, Nicolas Guilbaud, Jean-Paul Vilaine
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Patent number: 5378718Abstract: Compounds a formula (I) ##STR1## wherein the substituents and symbols have the meanings given in the specification, are new compounds with marked cardiovascular activity.Type: GrantFiled: January 22, 1993Date of Patent: January 3, 1995Assignee: Cedona Pharmaceuticals B.V.Inventors: Jan Bron, Geert J. Sterk, Hendrik Timmerman, Jan F. Van Der Werf
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Patent number: 5342847Abstract: The invention relates to the new dimethyl 2,6-dimethyl-1-n-propyl-4-(trifluoro-methylphenyl)-1,4-dihydropyridine-3-d icarboxylate, a process for its preparation and its use as a medicament in ischaemic diseases which are associated with disorders of the microcirculation. This action can occur both in the peripheral and in the cerebral vascular system.Type: GrantFiled: January 16, 1993Date of Patent: August 30, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Hartmund Wollweber, Siegfried Goldmann, Bruno Rosen, Siegfried Zaiss
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Patent number: 5336774Abstract: A 1,4-dihydropyridine derivative represented by formula (I): ##STR1## wherein X represents an alkyl group, or a group of ##STR2## in which R.sub.1, R.sub.2, and R.sub.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a nitro group, a nitrile group, or a trifluoromethyl group; R.sub.4 represents a substituted or unsubstituted acyloxymethyl group, an alkoxycarbonyloxymethyl group, a (2-oxo-1,3-dioxolen-4-yl)methyl group, a (5-substituted-2-oxo-1,3-dioxolen-4-yl)methyl group, or an acyl group; R.sub.5 represents a lower alkyl group or a substituted alkyl group; and R.sub.6 represents a hydrogen atom, a lower alkoxymethyl group, or a lower acyloxymethyl group, is disclosed.Type: GrantFiled: May 10, 1993Date of Patent: August 9, 1994Inventor: Kazuo Achiwa
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Patent number: 5296601Abstract: A process for producing a carboxylic acid ester, which comprises reacting an organic chloride having at least one chlorine atom on its ring of a substituted or unsubstituted, aromatic or heterocyclic hydrocarbon with carbon monoxide and an amine or an alcohol in the presence of a base by using as catalysts a palladium compound and a phosphine compound represented by the general formula (V):(R).sub.2 P--X--P(R).sub.2 (V)wherein R is an alkyl group or a substituted or unsubstituted phenyl group, and X is an alkylene group having 1 to 6 carbon atoms, ##STR1## or a binaphthyl group.Type: GrantFiled: May 27, 1992Date of Patent: March 22, 1994Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5286868Abstract: There is provided a process for the preparation of dialkyl pyridinedicarboxylate compounds and derivatives thereof by reacting a dialkyl chloromaleate or chlorofumarate or a mixture thereof with an ammonium salt optionally in the presence of ammonia and an appropriately substituted .alpha.,.beta.-unsaturated aldehyde or ketone.Type: GrantFiled: May 1, 1992Date of Patent: February 15, 1994Assignee: American Cyanamid CompanyInventors: Albert A. Cevasco, George A. Chiarello, William F. Rieker
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Patent number: 5284955Abstract: There are provided crystalline substituted-2,3-dicarboxypyridinium nitrate salts, the preparation thereof and the use thereof in the isolation and purification of important substituted pyridinedicarboxylic acid herbicide intermediates.Type: GrantFiled: October 28, 1992Date of Patent: February 8, 1994Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5276157Abstract: The present invention provides a process for the purification of 2,3-pyridine and quinolinedicarboxylic acid diester compounds via extraction with a mineral acid.Type: GrantFiled: December 20, 1991Date of Patent: January 4, 1994Assignee: American Cyanamid CompanyInventor: William F. Rieker
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Patent number: 5264446Abstract: The invention is directed to the provision of solid pharmaceutical compositions (and methods for their preparation) containing nifidipine crystals with a specific surface area of 1.0 to 4.0 m.sup.2 /g., in admixture with a solid diluent. The said compositions overcome the deficiencies of prior art compositions containing nifidipine, which is known to have effect as a coronary vasodilator.Type: GrantFiled: June 1, 1992Date of Patent: November 23, 1993Assignee: Bayer AktiengesellschaftInventors: Ahmed Hegasy, Klaus-Dieter Ramsch
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Patent number: 5260323Abstract: 2,4- and 2,5-substituted pyridine-N-oxides are provided which are effective as fibrosuppressives and immunosuppressives. Said compounds are also suitable for the treatment of disorders of the metabolism of collagen and collagen-like substances or the biosynthesis of Clq.Type: GrantFiled: November 19, 1992Date of Patent: November 9, 1993Assignee: Hoechst AktiengesellschaftInventors: Ekkehard Baader, Martin Bickel, Volkmar Gunzler-Pukall
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Patent number: 5252739Abstract: A process for preparing pyridine-2,3-dicarboxylic acid compounds of the following formula, which comprises preparing .alpha.-halo-oxalacetic acid diesters by reacting oxalacetic acid diester alkali metallic salts with an acid and a halogenating agent or by reacting oxalic acid diesters with halo-acetic acid esters, and then reacting the obtained .alpha.-halo-oxalacetic acid diesters with 2-propenal compounds and ammonia. ##STR1## wherein R.sup.1 and R.sup.2 are, identical or different, a lower alkyl group, and R.sup.3 is a hydrogen atom or a lower alkyl group.The pyridine-2,3-dicarboxylic acid compounds obtained by the process of the invention are useful as an intermediate for manufacturing agricultural chemicals and pharmaceuticals.Type: GrantFiled: February 3, 1992Date of Patent: October 12, 1993Assignee: Sugai Chemical Ind. Co., Ltd.Inventors: Takaharu Yamashita, Mitsuhiro Kodama
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Patent number: 5250694Abstract: There is provided a process for the preparation of a 2,3-pyridinedicarboxylic acid from a 3-(2-imidazolin-2-yl)picolinic acid. The 2,3-pyridinedicarboxylic acids are useful in the preparation of herbicidal 2-(2-imidazolin-2-yl)nicotinic and quinoline-3-carboxylic acids, esters and salts.Type: GrantFiled: August 26, 1992Date of Patent: October 5, 1993Assignee: American Cyanamid CompanyInventor: Paul E. Miller
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Patent number: 5245039Abstract: A process for the optical resolution of racemic 1,4-dihydropyridines, containing isothioureido groups. Salification of racemic isothioureas with optically active acids produces diasteroisomeric mixtures of isothiouronium salts, that, using conventional techniques, are separated in the individual components to give optically pure isothioureides of 1,4-dihydropyridines and salts thereof with conventional acids. Said optically pure 1,4-dihydropyridines can then be subjected to desulphuration and to different transformations to give to other enantiomerically pure and therapeutically useful 1,4-dihydropyridines.Type: GrantFiled: August 14, 1991Date of Patent: September 14, 1993Assignee: Boehringer Mannheim ItaliaInventors: Carmelo A. Gandolfi, Marco Frigerio, Carlo Riva, Andrea Zaliani, Giorgio Long, Roberto D. Domenico
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Patent number: 5234935Abstract: Improving circulation, with minimal effect on blood pressure, using N-alkylated 1,4-dihydropyridines of the formula ##STR1## in which R.sup.1 represents hydrogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, halogen or methyl,R.sup.2 represents hydrogen, halogen, nitro, hydroxyl, trifluoromethyl or methyl,R.sup.3 represents hydrogen or cyano, orR.sup.2 and R.sup.3 together form a fused benzo ring,R.sup.4 and R.sup.5 are identical or different and represent straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by alkoxy having up to 4 carbon atoms, andR.sup.6 represents straight-chain or branched alkyl having up to 10 carbon atoms or represents cycloalkyl having 3 to 7 carbon atoms.Many of the compounds are new.Type: GrantFiled: April 4, 1991Date of Patent: August 10, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Hartmut Wollweber, Bruno Rosen, Siegfried Zaiss, Siegfried Goldmann
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Patent number: 5234821Abstract: A 1,4-dihydropyridine derivative represented by formula (I): ##STR1## wherein X represents an alkyl group, or a group of ##STR2## in which R.sub.1, R.sub.2, and R.sub.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a nitro group, a nitrile group, or a trifluoromethyl group; R.sub.4 represents a substituted or unsubstituted acyloxymethyl group, an alkoxycarbonyloxymethyl group, a (2-oxo-1,3-dioxolen-4 -yl)methyl group, a (5-substituted-2-oxo-1,3-dioxolen-4 -yl)methyl group, or an acyl group; R.sub.5 represents a lower alkyl group or a substituted alkyl group; and R.sub.6 represents a hydrogen atom, a lower alkoxymethyl group, or a lower acyloxymethyl group, is disclosed. The compound is stereospecifically hydrolyzed by the action of an enzyme to provide an optically active 1,4-dihydro -3-pyridinemonocarboxylic acid which is useful as an intermediate of pharmaceuticals in good optical purity and yield.Type: GrantFiled: August 30, 1991Date of Patent: August 10, 1993Inventor: Kazuo Achiwa
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Patent number: RE35177Abstract: A pyridine-compound is reacted with fluorine together with a .[.Bronsted.]. .Iadd.Bronsted .Iaddend.acid-compound or Lewis acid to form a N-fluoropyridinium salt which is very active to other compounds but is very selective for the preparation of a desired product and this product is very useful for a fluorine-introducing agent which makes it useful for the preparation of fluoro-compounds such as thyroid inhibitor.Type: GrantFiled: February 17, 1994Date of Patent: March 12, 1996Assignees: Sagami Chemical Research Center, Chichibu Onoda Cement CorporationInventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa