Additional -coo- Group Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/321)
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Patent number: 4621093Abstract: 4-(Nitrophenyl)-1,2,3,4-tetrahydropyridines of the formula ##STR1## in which R.sub.1 and R.sub.2 are identical or different and each represent hydrogen, phenyl or a straight-chain or branched alkyl radical which is optionally substituted by halogen or alkoxy,R.sub.3 represents a straight-chain or branched alkyl radical which is optionally substituted by alkoxy, halogen, alkylamino or aryl,X represents a single bond, an oxygen atom, a sulphur atom or the NH group andY denotes either the nitrile group or the radical ##STR2## wherein X' corresponds to the definition of X and can either be identical to X or different from X, andR.sub.4 corresponds to the definition of R.sub.3 and can be either identical to R.sub.3 or different from R.sub.3,or physiologically acceptable salts thereof, which are active on the circulation system, for example as vasodilators.Type: GrantFiled: April 8, 1985Date of Patent: November 4, 1986Assignee: Bayer AktiengesellschaftInventors: Rosentreter Ulrich, Gunter Thomas, Andreas Knorr
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Patent number: 4607041Abstract: There are described compounds of formula I, ##STR1## in which R.sub.1 represents benzofurazanyl, pyridyl or phenyl, the pyridyl or phenyl being substituted by one or more of the groups halogen, nitro, --CN, --OR.sub.9, --S(O).sub.p R.sub.9, or alkyl C1 to 6 optionally substituted by halogen,p is 0, 1 or 2,R.sub.2 and R.sub.3, which may be the same or different, each represent hydrogen; alkyl C1 to 6 optionally substituted by one or more of the groups halogen, cyano, --XR.sub.4, --NR.sub.5 R.sub.6 or phenyl; cycloalkyl C3 to 8 optionally substituted by alkyl C1 to 6; a 4, 5 or 6 membered oxygen or nitrogen containing heterocyclic ring which is optionally substituted by alkyl C1 to 6 the alkyl in turn optionally being substituted by one or more phenyl groups;R.sub.5 and R.sub.6, which may be the same or different, each represent alkyl C1 to 6 optionally substituted by phenyl,Y and Z together form a bond, and additionally, when R.sub.Type: GrantFiled: April 17, 1984Date of Patent: August 19, 1986Assignee: Fisons plcInventors: Andrew J. G. Baxter, John Dixon, Thomas McInally, Alan C. Tinker
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Patent number: 4603135Abstract: Dihydropyridine derivatives and acid addition salts thereof which are of use as prophylactic or/and therapeutic drugs for cardiovascular diseases, said dihydropyridine derivatives having the formula ##STR1## wherein R.sup.1 is a hydrogen atom or an aryl,R.sup.2 and R.sup.3 are the same or different and each is an aryl,R.sup.4 and R.sup.6 are the same or different and each is a lower alkyl,R.sup.5 is amino or a lower alkyl,A is an alkylene,X is N or CH andm and n are the same or differentand each is 0 or 1,with the proviso that when X is N, R.sup.5 is amino.Type: GrantFiled: September 25, 1984Date of Patent: July 29, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Kanji Meguro, Akinobu Nagaoka
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Patent number: 4600778Abstract: In the preparation of a 1,4-dihydropyridine of the formula ##STR1## in which R is a phenyl radical which is optionally substituted once or twice by nitro and/or chlorine,R.sub.1 is a C.sub.1 -C.sub.4 -alkyl radical which is optionally substituted by a C.sub.1 -C.sub.4 -alkoxy group, andR.sub.2 is a C.sub.1 -C.sub.12 -alkyl radical which is optionally substituted by a C.sub.1 -C.sub.4 -alkoxy group, a trifluoromethyl group or the radical (C.sub.6 H.sub.5 CH.sub.2) (CH.sub.3)N,by preparing an ylidene compound of the formula ##STR2## and reacting such ylidene compound with an enamine compound of the formula ##STR3## the improvement which comprises preparing the ylidene compound by reaction of a ketocarboxylic ester of the formula ##STR4## with an aldehyde of the formula RCHO, in a solvent in the presence of a catalytic amount of any acetate salt of an amine, at a temperature from about -10.degree. C. up to 100.degree. C. The products symmetrical or unsymmetrical, are produced in high yield and purity.Type: GrantFiled: March 20, 1984Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventors: Werner Teller, Wolfgang Koebernick, Arthur Haaf, Paul Naab, Michael Preiss
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Patent number: 4595690Abstract: Novel dihydropyridine derivatives which are useful for treating congestive heart failure, hypertension, and angina have the formula 1: ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8;Y is --O, --NH, --NR.sub.2, --S, --S(O), --S(O).sub.2, or a bond;R.sub.1 and R.sub.2 are each independently A.sub.1, A.sub.2, A.sub.3 or A.sub.4 where:A.sub.1 is --(CH.sub.2).sub.m (CHOH).sub.p CH.sub.2 OH;A.sub.2 is --(CH.sub.2).sub.q CH.sub.(3-r) [(CH.sub.2).sub.s OH].sub.r ;A.sub.3 is --(CH.sub.2).sub.q CH.sub.(3-r) [(CH.sub.2).sub.p COOR.sub.3 ].sub.r ; andA.sub.4 is --(CH.sub.2).sub.m COOR.sub.3 ; where:m is an integer from 1 to 8;p is an integer from 0 to 4;q is an integer from 0 to 8;r is 2 or 3;s is an integer from 1 to 4; andR.sub.3 is H or alkyl of 1 to 18 carbon atoms;R.sub.4 is --NO.sub.2, --CF.sub.3, or halo; andR.sub.5 is lower alkyl or --CH.sub.2 CH.sub.2 OCH.sub.3.Type: GrantFiled: February 11, 1985Date of Patent: June 17, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Robin Clark, Moysey M. Povzhitkov
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Patent number: 4582840Abstract: A method of combating a disorder of the salt balance in a patient afflicted therewith comprising administering to such patient a salt-balance restoring effective amount of a vasodilating 1,4-dihydropyridine of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is alkyl with 1 to 4 carbon atoms, and the nitro radical is in the ortho- or meta-position of the phenyl radical.The salt balance disorder may accompany the hypertensive disease or may also be aggravated by administering to such a patient a hypertension reducing agent.Type: GrantFiled: April 25, 1985Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Bernward Garthoff, Stanislav Kazda, Andreas Knorr, Gunter Thomas
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Patent number: 4579859Abstract: The invention relates to novel dihydropyridine derivatives of vasodilating activity of the formula: ##STR1## in which R.sup.1 is aryl selected from the group consisting of phenyl, tolyl, xylyl, cumenyl and mesityl which may have one or more substituents selected from the group consisting of halogen, nitro, hydroxy, carboxy and lower alkoxy, or a heterocyclic group containing at least one hetero atom selected from the group consisting of oxygen, nitrogen and sulfur,R.sup.2 is lower alkoxy-carbonyl or N,N-disubstituted amino(lower)alkoxycarbonyl,R.sup.3 is lower alkyl, alkanoyl, protected alkanoyl or cyano,R.sup.4 is lower alkyl andA is lower alkylene, and pharmaceutically acceptable salt thereof.Type: GrantFiled: May 17, 1984Date of Patent: April 1, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Daizo Morino, Koichi Takimoto
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Patent number: 4578395Abstract: A 1,4-dihydropyridine derivative of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and each represents a hydrogen atom, a halogen atom or a nitro group, provided that R.sup.1 and R.sup.2 are not hydrogen atoms at the same time; R.sup.3 represents an alkyl group; R.sup.4 represents an aralkyl group which may be substituted; R.sup.5 and R.sup.7 are indentical or different and each represents an alkyl group; R.sup.6 represents a hydrogen atom or an alkyl group; R.sup.8 represents an alkyl group; R.sup.9 represents a hydrogen atom or an alkyl group; n and m are identical or different and each represents an integer of 0 to 6; provided that when either one of R.sup.1 and R.sup.2 is a hydrogen atom, R.sup.9 is an alkyl group;or an acid addition salt thereof.The 1,4-dihydropyridine derivative is characterized by a strong antihypertensive activity and the long duration of the activity.Type: GrantFiled: June 1, 1984Date of Patent: March 25, 1986Assignee: Teijin LimitedInventors: Hisao Yamaguchi, Hideo Kanno, Yoshiaki Okamiya, Kiyotaka Sunakawa
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Patent number: 4572909Abstract: A dihydropyridine compound of the formula ##STR1## or a pharmaceutically acceptable acid addition salt thereof, whereinY is --(CH.sub.2).sub.2 --, --(CH.sub.2).sub.3 --, --CH.sub.2 CH(CH.sub.3)-- or --CH.sub.2 C(CH.sub.3).sub.2 --;R is aryl or heteroaryl;R.sup.1 and R.sup.2 are each independently C.sub.1 -C.sub.4 alkyl or 2-methoxyethyl; andR.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, 2-(C.sub.1 -C.sub.4 alkoxy)ethyl, cyclopropylmethyl, benzyl, or --(CH.sub.2).sub.m COR.sup.4 where m is 1, 2 or 3 andR.sup.4 is hydroxy, C.sub.1 -C.sub.4 alkoxy or --NR.sup.5 R.sup.6 where R.sup.5 and R.sup.6 are each independently hydrogen or C.sub.1 -C.sub.4 alkylcan be employed for treating or preventing a heart condition or hypertension.Type: GrantFiled: February 3, 1984Date of Patent: February 25, 1986Assignee: Pfizer Inc.Inventors: Simon F. Campbell, Peter E. Cross, John K. Stubbs
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Patent number: 4568681Abstract: 1,2,3,4-Tetrahydropyridines of the formula ##STR1## in which R.sup.1 is optionally substituted aryl or heterocyclic,R.sup.2 is an organic radical,X is a nitrile or ester,R.sup.3 and R.sup.5 are identical or different and each represent hydrogen, a straight-chain or branched or salts thereof with physiologically tolerated acids are antihypertensives.Type: GrantFiled: October 3, 1983Date of Patent: February 4, 1986Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Stanislav Kazda, Andreas Knorr
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Patent number: 4565824Abstract: Dihydropyridines of the formula ##STR1## in which R is aryl or heterocyclic,R.sup.1, R.sup.2 and R.sup.3 each is hydrogen or various organic radicals,Y is oxygen, or optionally substituted --NH--,Z is --O--NO.sub.2 or --O--NO,X is --COR.sup.4, --COOR.sup.5 or --CO--Y--A--Z,R.sup.4 is alkyl, phenyl, benzyl or an amino radical, andR.sup.5 is an organic radical,or pharmaceutically acceptable acid addition salts thereof, exhibit circulation active properties, e.g. they can be used as antihypertensives, as peripheral and cerebral vasodilators and as coronary therapeutics.Type: GrantFiled: November 9, 1983Date of Patent: January 21, 1986Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Stanislav Kazda, Andreas Knorr
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Patent number: 4562257Abstract: The invention provides a process for the preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids.Type: GrantFiled: November 7, 1983Date of Patent: December 31, 1985Assignee: American Cyanamid CompanyInventor: David V. Petrocine
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Patent number: 4556716Abstract: Process for the production of 2-halopyridine derivatives having the formula: ##STR1## wherein X is halogen, R is --COOH or a lower alkyl radical and n is a number between 0 and 4. The corresponding 2-pyridine carboxylic acid-N-oxide derivatives having the formula: ##STR2## are reacted in the presence of an excess of organic anhydrides, tertiary alkylamines and a halogen-producing compound having the formula CH.sub.t X.sub.m, wherein t is 1 or 2, m is 2 or 3 and X is halogen, or having the formula C.sub.2 H.sub.p X.sub.m, wherein p is 3 or 4, m is 2 or 3 and X is halogen. The reaction mixture is adjusted to a pH value of 12 to 13 and the desired product is isolated from the mixture. Compound comprising (i) a 2-pyridine carboxylic acid-N-oxide derivative, (ii) an organic anhydride, (iii) a tertiary amine and (iv) a halogen-producing compound having the formula CH.sub.n X.sub.m. The composition can be used as the starting ingredients for the above process.Type: GrantFiled: January 11, 1983Date of Patent: December 3, 1985Assignee: Lonza Ltd.Inventor: Daniel Quarroz
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Patent number: 4551467Abstract: The invention relates to 1,4-dihydropyridines as well as methods for the preparation of said 1,4-dihydropyridines and compositions contained therein. The invention also includes the use of said compounds and compositions for influencing circulation.Type: GrantFiled: October 11, 1979Date of Patent: November 5, 1985Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Friedrich Bossert, Wulf Vater, Kurt Stoepel
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Patent number: 4540810Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.Type: GrantFiled: September 20, 1979Date of Patent: September 10, 1985Assignee: Texaco Development CorporationInventor: John F. Knifton
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Patent number: 4537971Abstract: This invention relates to improved processes for the manufacture of quinolinic acid run with a higher concentration of reactants in the initial step wherein quinoline is oxidized with hydrogen peroxide in an aqueous sulfuric acid solution in the presence of copper sulfate to prepare copper quinolinate, and in subsequent steps converting the copper quinolinate from the initial step to quinolinic acid by treating the copper salt with alkali to form the water soluble alkali salt form of quinolinic acid precipitating the copper as insoluble cupric oxide and thereafter treating the soluble alkali salt form with acid to obtain the quinolinic acid, the improvement whereby the reaction of the initial step is carried out in a thermally controllable and safe manner and the formation of by-products is minimized which comprises in the initial step adding separately either in portion-wise multiple and approximately equal portions or adding continuously and simultaneously over a period of time each of the following, the suType: GrantFiled: September 26, 1983Date of Patent: August 27, 1985Assignee: The Hilton-Davis Chemical Co.Inventors: Robert W. J. Rebhahn, James E. Kassner, Raymond E. Werner
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Patent number: 4525478Abstract: 1,4-Dihydropyridine derivatives of the general formula ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.Type: GrantFiled: September 3, 1982Date of Patent: June 25, 1985Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventor: Yoshinari Sato
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Patent number: 4521603Abstract: A continuous process for producing a polybromopyridine compound comprises admixing a polychloropyridine compound with an anhydrous water soluble solvent in a first reaction zone to form a solution of the polychloropyridine compound. Hydrogen bromide gas is introduced into the solution while maintaining the temperature in the range of from about 70.degree. to about 140.degree. C. to produce a solution of the polybromopyridine compound. The solution is cooled to a temperature in the range of from about 5.degree. to about 35.degree. C. to precipitate the polybromopyridine compound from the anhydrous solvent. The polybromopyridine compound is separated from the anhydrous solvent and the anhydrous solvent is returned to the first reaction zone. Polybromopyridine compounds of increased purity are produced in a process having reduced material, energy and operating costs. The process does not require the use of water or other co-solvents nor the distillation of the reaction product mixture.Type: GrantFiled: February 1, 1983Date of Patent: June 4, 1985Assignee: Olin CorporationInventor: Max M. Boudakian
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Patent number: 4520131Abstract: Antihypertensive compounds of the formula ##STR1## where the substituents are as herein defined and where Z is alkylene, R.sub.3 is alkoxyalkyl and R.sub.4 is hydroxyalkyl.Type: GrantFiled: March 3, 1983Date of Patent: May 28, 1985Assignee: USV PharmaceuticalInventors: Bernard Loev, Howard Jones, John T. Suh
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Patent number: 4510310Abstract: The invention relates to optically active 1,4-dihydropyridine compounds of Formulas Ia and Ib as defined hereinabove which are effective for influencing circulation. Also included in the invention are compositions containing said optically active compounds and methods for the use of said compounds and compositions.Type: GrantFiled: September 30, 1982Date of Patent: April 9, 1985Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Friedrich Bossert, Wulf Vater, Robertson Towart, Kurt Stoepel, Stanislay Kazda
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Patent number: 4505920Abstract: Unsaturated heterocyclic dihydropyridine of the formula ##STR1## wherein R.sub.3 and R.sub.4 together with the N to which they are attached form an unsaturated heterocyclic group, have been found to possess useful anti-hypertensive activity.Type: GrantFiled: March 3, 1983Date of Patent: March 19, 1985Assignee: USV Pharmaceutical CorporationInventors: Bernard Loev, Howard Jones, John T. Suh
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Patent number: 4500527Abstract: Unsaturated heterocyclic dihydropyridines of the formula: ##STR1## wherein the substituents defined herein have been found to have useful antihypertensive activity.Type: GrantFiled: June 22, 1983Date of Patent: February 19, 1985Assignee: USV Pharmaceutical CorporationInventors: Bernard Loev, James R. Shroff, Rohit Desai
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Patent number: 4500532Abstract: Compounds of the formula ##STR1## wherein Z is alkylene containing 1 to 5 carbon atoms; R.sub.3 is aminoalkyl containing 2 to 4 carbon atoms; R.sub.4 is H, alkyl, cycloalkyl, aminoalkyl, hydroxyalkyl or alkoxyalkyl; and the remainder of the variables are as described in the specification are useful as anti-hypertensives.Type: GrantFiled: March 3, 1983Date of Patent: February 19, 1985Assignee: USV Pharmaceutical CorporationInventors: Bernard Loev, Howard Jones, John T. Suh
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Patent number: 4495192Abstract: A vasodilating or anti-hypertensive composition comprises a pharmaceutical carrier and an effective amount of a 1,4-dihydropyridine compound as an active ingredient. The 1,4-dihydropyridine compound may be represented by the following general formula: ##STR1## wherein R'.sub.1 and R'.sub.4 represent a hydrogen atom, R'.sub.2 and R'.sub.3 represent an alkyl group having 1-5 carbon atoms or a substituted heterocyclic group wherein a substituent is an N-benzylpiperidyl group, R'.sub.5 represents a nitro group, and R'.sub.6 and R'.sub.7 represent an alkyl group having 1-5 carbon atoms.Type: GrantFiled: April 29, 1983Date of Patent: January 22, 1985Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Kenji Muto, Yoshinori Takemoto, Takao Hatta, Tamotsu Hashimoto, Koji Yamada, Minoru Watanabe
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Patent number: 4492703Abstract: 1,4-Dihydropyridines of the formula ##STR1## in which R.sup.1, R.sup.4, R.sup.5, R.sup.6 and Y are hydrogen or various organic radicals,R.sup.2 and R.sup.3 are various organic radicals, ##STR2## is phenyl, naphthyl or various heterocyclic radicals, X is a direct bond, O, S or SO, andB is a direct bond or alkylene,or pharmaceutically acceptable addition salts thereof exhibit hypotensive, vasodilating and coronary activities.Type: GrantFiled: February 22, 1983Date of Patent: January 8, 1985Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Horst Boshagen, Jurgen Stoltefuss, Matthias Schramm, Gunter Thomas, Stanislav Kazda
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Patent number: 4487932Abstract: A compound 2,6-dimethyl-3,5-bis-(1-adamantylhydroxycarbonyl)-4-(2-difluoromethoxyphen yl)-1,4-dihydropyridine of the formula ##STR1## is proposed. Said compound possesses antianginal activity.Type: GrantFiled: April 19, 1983Date of Patent: December 11, 1984Assignee: Institut Organicheskogo Sinteza Akademii Nauk LatviiskoiInventors: Egils A. Biseniex, Maris M. Veveris, Gunar Y. Dubur, Yanis J. Polis, Yan R. Uldrikis, Natalia V. Barmenkova, Agris A. Kimenis
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Patent number: 4485239Abstract: 2-(2,6-dimethyl-3,5-diethoxycarbonyl-1,4-dihydropyridine-4-carboxamide) glutaric acid of formula I and its disodium salt of formula II ##STR1## Said acid is obtained from glutaminic acid and dimethyl 3,5-diethoxycarbonyl-1,4-dihydroisonicotic acid.For obtaining disodium salt, said acid is reacted with a caustic soda solution.These compounds possess antiarrhythmic activity.Type: GrantFiled: September 28, 1983Date of Patent: November 27, 1984Assignee: Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi SSRInventors: Egils A. Biseniex, Gunar Y. Dubur, Yan R. Uldrikis, Maris M. Veveris, Agris A. Kimenis, Evgeny V. Ivanov
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Patent number: 4483985Abstract: The invention relates to a process for the production of 1,4-dihydropyridinecarboxylic acid compounds which involves hydrolysis, under alkaline conditions and in a temperature range from 10.degree. to 100.degree. C., of an ester group which contains an electron-attracting group. The invention also includes novel compounds made according to the invention as well as compositions containing said novel compounds. Also included in the invention are methods for the use of said compounds and compositions. The compounds obtained according to the process of the invention are useful because of their circulation-influencing action and are also useful as intermediates for the preparation of compounds having circulation-influencing action.Type: GrantFiled: January 19, 1981Date of Patent: November 20, 1984Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Friedrich Bossert
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Patent number: 4472584Abstract: Compounds of the formula: ##STR1## wherein Ar is heteroaryl, cycloalkyl having from 3 to 7 carbon atoms, naphthyl, indanyl, indenyl, tetrahydro naphthyl, or a radical of the formula ##STR2## wherein each of R.sub.5, R.sub.6 and R.sub.7 is independently H, alkyl, aryl, halo, lower alkoxy, nitro, amino, alkylmercapto, cyano, carboxy, carbalkoxy, sulfamyl, trifluoromethyl, hydroxy, acyloxy, methanesulfonyl, alkylamino or acylamino; and R.sub.5 and R.sub.6 when taken together, form a methylenedioxy; Z is alkylene containing 1 to about 5 carbon atoms in the principal chain; each R.sub.1 is independently hydrogen, alkyl or alkoxyalkyl, with the proviso that only one R.sub.1 may be hydrogen; R.sub.2 is lower alkyl; R.sub.3 is hydroxyalkyl containing 2 to 4 carbon atoms and R.sub.4 is H, alkyl, cycloalkyl or hydroxyalkyl containing 2 to 4 carbon atoms; wherein the alkyl, alkoxy, and acyl groups contain up to 10 carbon atoms, and their pharmaceutically-acceptable salts are disclosed.Type: GrantFiled: March 3, 1983Date of Patent: September 18, 1984Assignee: USV Pharmaceutical CorporationInventors: Bernard Loev, Howard Jones, John T. Suh
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Patent number: 4472411Abstract: The compounds of the formula ##STR1## wherein R is alkyl having 1 to 4 carbon atoms or nitratoalkyl having 2 or 3 carbon atoms, and R' is nitratoalkyl having 2 or 3 carbon atoms, are disclosed. These compounds are useful as therapeutic agents for cardiovascular disorders such as coronary artery disease, cerebral artery disease, hypertension and the like.Type: GrantFiled: April 19, 1983Date of Patent: September 18, 1984Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Katsuo Hatayama, Aturo Nakazato, Toshihisa Ogawa, Shoichi Ito, Jiro Sawada
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Patent number: 4467093Abstract: In the process for preparing 4-(2'-nitrophenyl-2,6-dimethyl)-3,5-dicarbmethoxy-1,4-dihydropyridine of the formula ##STR1## 2-nitrobenzaldehyd-diacetate, methyl acetoacetate and ammonia are reacted in the presence of an inert organic solvent, such as methanol, and in the presence or absence of an organic base, such as pyridine, at a temperature of between 20.degree. and 150.degree. C. The compound is a valuable medicine for the treatment of angina pectoris.Type: GrantFiled: July 27, 1982Date of Patent: August 21, 1984Assignee: LEK, Tovarna Farmacevtskih in Kemicnih Izdelkov, N.Sol.O.Inventors: Branko Jenko, Igor Langof
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Patent number: 4446325Abstract: 1,4-Dihydropyridine compounds having excellent coronary and vertebral vasodilation, blood pressure depression and anti-hypertensive activities are disclosed. These compounds are low toxic and stable to light, and are very useful for pharmaceutical agents.Type: GrantFiled: October 19, 1982Date of Patent: May 1, 1984Assignee: Maruko Seiyaku Co., Ltd.Inventors: Sachio Ohno, Kiyoshi Mizukoshi, Osamu Komatsu, Kenzi Ichihara, Takashi Morishima
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Patent number: 4443456Abstract: This invention relates to a novel class of amidinourea and amidinothiourea compounds wherein the urea nitrogen atom is substituted by a heterocyclic alkylene group, and their use in pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anesthetic, anti-arrhythmic, antidiarrheal and antiparasitic action.Type: GrantFiled: May 12, 1981Date of Patent: April 17, 1984Assignee: William H. Rorer, Inc.Inventors: George H. Douglas, William L. Studt, Stuart A. Dodson, Harry K. Zimmerman
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Patent number: 4435574Abstract: The present invention relates to derivatives of 1,4-dihydropyridine and, more specifically, to 2,6-dimethyl-3,5-dicarbomethoxy-4-(o-difluoromethylthiophenyl)-1,4-dihydro pyridine having the formula ##STR1## The proposed compound features pronounced hypotensive activity of prolonged duration and is capable of producing a coronarodilating effect while having low toxicity and being useful for treating diseases of the cardiovascular system.Type: GrantFiled: July 16, 1982Date of Patent: March 6, 1984Inventors: Valeria V. Kastron, Rasma O. Vitolin, Gunar Y. Dubur, Marita Y. Selga, Guntis V. Zarinsh, Natalya V. Kondratenko, Vladimir I. Popov, Alexandr A. Kolomeitsev, Lev M. Yagupolsky
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Patent number: 4430333Abstract: Dihydropyridine anti-ischaemic and antihypertensive agents of the formula: ##STR1## where Y is --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 --;R is aryl or heteroaryl;R.sup.1 and R.sup.2 are each independently C.sub.1 -C.sub.4 alkyl or 2-methoxyethyl;andR.sup.3 and R.sup.4 are each independently C.sub.1 -C.sub.4 alkyl or aryl-(C.sub.1 -C.sub.4 alkyl); or R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached represent a group of the formula: ##STR2## where R.sup.5 is C.sub.1 -C.sub.4 alkyl, aryl, aryl-(C.sub.1 -C.sub.4 alkyl), benzhydryl; 2-methoxyethyl, 2-(N,N-di[C.sub.1 -C.sub.4 alkyl]amino) ethyl, or cyclopropylmethyl;their pharmaceutically acceptable acid addition salts, processes for the preparation of the compounds, and pharmaceutical compositions containing them.Type: GrantFiled: March 11, 1982Date of Patent: February 7, 1984Assignee: Pfizer Inc.Inventors: Simon F. Campbell, Peter E. Cross, John K. Stubbs
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Patent number: 4423052Abstract: 1,4-Dihydropyridine-3,5-dicarboxylic acid ester derivatives represented by the formula ##STR1## (wherein Ar.sup.1 and Ar.sup.2 are each the same or different and represent an aryl group; R.sup.1 represents a lower alkyl group; R.sup.2 and R.sup.3 are each the same or different and represent a lower alkyl or aralkyl group; n is 1 or 2; and R.sup.4 represents a lower alkyl) or the acid addition salts thereof. These compounds are useful as antihypertensive agents and as agents for treating the disturbances of cardiac or cerebral circulation.Type: GrantFiled: June 1, 1982Date of Patent: December 27, 1983Assignee: Yoshitomi Pharmaceutical Industries Ltd.Inventors: Kazuhiko Araki, Hideki Ao, Kenichi Aihara, Tomohiko Kimura
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Patent number: 4420616Abstract: A process for the preparation of copper quinolinate in which quinoline is oxidized by hydrogen peroxide in sulfuric acid in the presence of copper sulfate wherein the reaction is carried out at a pressure of less than 400 mm Hg. The reduced pressure enables the reaction to be performed at higher temperatures and with greater control; also the reaction time is shortened and the yield improved.Copper quinolinate is used to prepare quinolinic acid which is the starting material for some chromogenic materials used in the pressure-sensitive record material field.Type: GrantFiled: February 20, 1981Date of Patent: December 13, 1983Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventors: Seishi Ikegami, Yoshihiro Hatano
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Patent number: 4404378Abstract: Novel compounds having vasodilation and hypotensive effects are represented by the formula ##STR1## where R.sup.1 is halogen, nitro, cyano or lower alkoxy; each of R.sup.2 and R.sup.3 is lower alkyl, lower haloalkyl, lower alkoxyalkyl, aralkyloxyalkyl, aryloxyalkyl, lower alkenoxyalkyl, N,N-di-lower alkylaminoalkyl, N-lower alkyl-N-aralkylaminoalkyl, piperidylalkyl, 4-lower alkyl piperazinylalkyl, norpholinoalkyl or 1-pyrrolidinylalkyl; R.sup.4 is lower alkyl; A is lower alkylene; and R.sup.5 is hydrogen, lower alkyl, cycloalkyl of 3 to 7 carbon atoms, or aryl unsubstituted or substituted by one or two substituents selected from halogen, nitro, lower alkyl, lower alkoxy, di-lower alkylamino and cyano.Also disclosed are processes for their preparation.Type: GrantFiled: April 6, 1982Date of Patent: September 13, 1983Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Tetsuji Miyano, Kunio Suzuki, Nobuo Harada
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Patent number: 4395569Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.Type: GrantFiled: December 17, 1979Date of Patent: July 26, 1983Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Jerome F. Levy
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Patent number: 4393070Abstract: 1,4-dihydropyridine derivatives of the general formula: ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.Type: GrantFiled: December 4, 1980Date of Patent: July 12, 1983Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Yoshinari Sato, Tsutomu Teraji
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Patent number: 4370334Abstract: 1,4-Dihydropyridine derivatives of the general formula ##STR1## having vasodilating and anti-hypertensive activity, processes for preparing same, and pharmaceutical compositions thereof for treating cardiovascular diseases.Type: GrantFiled: December 4, 1980Date of Patent: January 25, 1983Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventor: Yoshinari Sato
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Patent number: 4364952Abstract: The invention relates to 1,4-dihydropyridines which carry an arylalkyl or aryloxyalkyl radical in the 4-position. Also included in the invention are methods for the preparation of said compounds. The invention further relates to compositions containing said 1,4-dihydropyridines and the use of said compounds and compositions for their circulation influencing effects.Type: GrantFiled: May 29, 1981Date of Patent: December 21, 1982Assignee: Bayer AktiengesellschaftInventor: Carsten Materne
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Patent number: 4351837Abstract: The invention relates to 1,4-dihydropyridine-4-carboxylic acid amines of the formula (I) as defined in the specification. Also included in the invention are methods for the preparation of said compounds. The invention further relates to compositions containing said 1,4-dihydropyridines and the use of said compounds and compositions for their circulation influencing effects.Type: GrantFiled: May 22, 1981Date of Patent: September 28, 1982Assignee: Bayer AktiengesellschaftInventor: Carsten Materne
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Patent number: 4338322Abstract: This invention relates to 2-or 6-cyano or cyano(lower)alkyl-4-phenyl or (substituted phenyl)1,4-dihydropyridine-3,5-dicarboxylates and derivatives which have vasodilating and hypertensive activity, processes for their preparation, pharmaceutical compositions for containing same and for methods of treating hypertension and cardiovascular diseases.Type: GrantFiled: August 25, 1980Date of Patent: July 6, 1982Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventor: Yoshinari Sato
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Patent number: 4317768Abstract: The instant invention relates to compounds of the general formula: ##STR1## wherein R.sub.1 represents an alkyl, alkenyl, phenyl or phenylalkyl radical, R.sub.2 represents an alkyl, alkenyl or alkynyl radical, a .omega.-halogenoethyl radical, an optionally substituted benzyl radical, a phenylalkenyl radical, an optionally substituted phenyl radical, a radical of the formula R.sub.4 --O--(CH.sub.2).sub.n -- wherein n is 2, 3, or 4 and R.sub.4 represents an optionally substituted alkyl radical or a phenyl radical, R.sub.3 represents a hydrogen atom, an alkyl, alkenyl or phenyl radical.The compounds of formula I have been found to be useful as stabilizers for vinyl resins.Type: GrantFiled: November 13, 1979Date of Patent: March 2, 1982Assignee: LabazInventors: Charles Pigerol, Marie-Madeleine Chandavoine, Paul de Cointet de Fillain
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Patent number: 4316026Abstract: A process for the preparation of copper quinolinate in which quinoline is oxidized by hydrogen peroxide in 10 to 30% sulfuric acid in the presence of copper sulfate at a temperature of 55.degree. to 75.degree. C., the molar ratio of sulfuric acid to quinoline being greater than 1:1. The concentration and amount of sulfuric acid enable greater control of the reaction temperature and result in copper quinolate in improved yield and purity.Copper quinolinate is used to prepare quinolinic acid which is the starting material for some chromogenic materials used in the pressure-sensitive record material field.Type: GrantFiled: August 12, 1980Date of Patent: February 16, 1982Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventors: Yoshihiro Hatano, Seishi Ikegami, Kenji Itoh, Mansuke Matsumoto
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Patent number: 4307103Abstract: This invention relates to a dihydropyridine derivative and a salt thereof. More particularly, it relates to a new dihydropyridine derivative and a pharmaceutically acceptable salt thereof which have vasodilating and anti-hypertensive activities, to processes for the preparation thereof, and to pharmaceutical composition comprising the same for therapeutical treatment of cardiovascular disorder and hypertension in human being.Type: GrantFiled: August 27, 1979Date of Patent: December 22, 1981Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Yoshinari Sato, Tsutomu Teraji
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Patent number: 4302591Abstract: Iminobenzyl dihydropyridines of the formula ##STR1## wherein, each R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, sulfonamido, halogen, alkoxy, alkenyloxy, alkynyloxy, cyano, hydroxy, acyloxy, nitro, amino, alkylmercapto, alkylamino, alkanoylamino, carbalkoxyamino, carboxy, methanesulfonyl, carbalkoxy or trifluoromethyl;each R.sub.4 is lower alkoxy;each R.sub.2 is lower alkyl;and R.sub.3 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic or ##STR2## wherein R is as previously defined; have anti-hypertensive activity.Type: GrantFiled: September 2, 1980Date of Patent: November 24, 1981Assignee: USV Pharmaceutical CorporationInventors: James R. Shroff, Bernard Loev
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Patent number: 4294969Abstract: Novel substituted (3-loweralkylamino-2-R.sub.1 O-propoxy)pyridines, their pharmaceutically acceptable salts, certain intermediates and their preparation are disclosed. These pyridines have pharmaceutically useful properties such as .beta.-adrenergic blocking activity.Type: GrantFiled: July 11, 1980Date of Patent: October 13, 1981Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, Gerald S. Ponticello
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Patent number: 4293700Abstract: 2,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid esters of the general formula: ##STR1## wherein R is a substituted alkyl or terpenyl. A method for preparing said esters comprises reacting esters of acetoacetic acid of the general formula: CH.sub.3 COCH.sub.2 COOR, wherein R is a substituted alkyl or terpenyl, with hexamethylenetetramine in the presence of ammonium acetate in ethanol at its boiling temperature; said esters of acetoacetic acid of the above general formula, hexamethylenetetramine and ammonium acetate can be used in stoichiometric proportions.Type: GrantFiled: April 3, 1980Date of Patent: October 6, 1981Inventors: Yan R. Uldrikis, Ieva E. Preisa, Gunar Y. Dubur, Aina A. Zidermane, Egils A. Biseniex, Gunar D. Tirzit