Additional -coo- Group Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/321)
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Patent number: 5231104Abstract: A series of novel 1-(phenethyl) and 1-(2-heteroarylethyl)-3-substituted piperidine derivatives have been prepared, including their pharmaceutically acceptable salts and various novel key intermediates therefor. The 3-substituent present in these compounds is an unsubstituted or substituted diphenylmethoxy group or a diphenylmethoxy-derived group, while the 1-substituent is unsubstituted or substituted phenethyl or 1-(2-heteroarylethyl) wherein the heteroaryl moiety is thienyl, pyridyl or pyrazinyl. These compounds in the form of both their racemates and 3R-isomers, are useful in therapy as smooth muscle muscarinic receptor antagonists and therefore, are of value in the treatment diseases associated with altered motility and/or smooth muscle tone.Type: GrantFiled: February 5, 1992Date of Patent: July 27, 1993Assignee: Pfizer Inc.Inventors: David Alker, Peter E. Cross, Robert M. Wallis
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Patent number: 5225560Abstract: There is provided a process for the preparation of substituted and unsubstituted-2,3-pyridinedicarboxylate compounds by reacting a dialkyl dichlorosuccinate with a dehydrohalogenating agent, an ammonia source and an appropriately substituted .alpha.,.beta.-unsaturated aldehyde or ketone.Type: GrantFiled: December 9, 1991Date of Patent: July 6, 1993Assignee: American Cyanamid CompanyInventors: Albert A. Cevasco, George A. Chiarello, William F. Rieker
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Patent number: 5216172Abstract: Agents against drug-resistant tumor cells comprising a 1,4-dihydropyridine derivative represented by the following formula (I): ##STR1## wherein R.sup.1 is an aryl group which may be substituted;R.sup.2 and R.sup.3, which may be the same or different, each is a member selected from the group consisting of an alkyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an aralkyloxycarbonyl group, an aminocarbonyl group, a hydroxycarbonyl group, a formyl group, and a cyano group, each of which may be substituted;R.sup.4 and R.sup.5 is a hydrogen atom or a member selected from the group consisting of a lower alkyl group, a hydroxymethyl group, a cyano group, an amino group, a formyl group, and a halogen atom; andR.sup.Type: GrantFiled: January 28, 1991Date of Patent: June 1, 1993Assignees: Ajinomoto Co., Inc., Japanese Foundation for Cancer ResearchInventors: Kouzou Toyota, Hisashi Shinkai, Hirozumi Eto, Akira Kamimura, Chikahiko Eguchi, Koji Ohsumi, Takashi Tsuruo
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Patent number: 5208342Abstract: In one embodiment this invention provides a process for converting a pyridine-2,3-dicarboxylic acid diester to the corresponding cyclic anhydride directly, without any recovery and purification of the pyridine-2,3-dicarboxylic acid intermediate.An important aspect of the invention process is the utility of pure pyridine-2,3-dicarboxylic acid diester starting matter. A procedure for providing pure diester starting material is demonstrated.Type: GrantFiled: March 30, 1992Date of Patent: May 4, 1993Assignee: Hoechst Celanese CorporationInventors: B. Franklin Gupton, John Saukaitis
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Patent number: 5206368Abstract: The present invention provides a process for extracting pyridine- and quinolinedicarboxylic acids from aqueous media. The pyridine- and quinolinedicarboxylic acids are useful in the preparation of herbicidal 2-(2-imidazolin-2-yl)nicotinate and quinoline-3-carboxylate compounds.Type: GrantFiled: February 7, 1992Date of Patent: April 27, 1993Assignee: American Cyanamid CompanyInventor: Richard L. Yager
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Patent number: 5182400Abstract: Process for the preparation of 5-alkylpyridine-2,3-dicarboxylic esters by reaction of 2-oxosuccinic esters with 2-alkylacrolein oximes.Type: GrantFiled: August 7, 1991Date of Patent: January 26, 1993Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Peter Lappe, Helmut Springer
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Patent number: 5177211Abstract: 4-alkyl-1,4-dihyropyridines, with PAF-antagonist activity, of formula (I) wherein R is saturated C.sub.1 -C.sub.4, R' is saturated C.sub.1 -C.sub.6 alkyl which may be interrupted by an oxygen atom, or 2-tetrahydrofurfuryl and R.sup.2 is saturated C.sub.1 -C.sub.4 or phenyl, the compound wherein R is methyl, R' is ethyl and R.sup.2 is phenyl remain excluded, are described.The compounds (I) are prepared by: (a) reaction of (II) with (III); (b) reaction of (IV) with (V); (c) reaction of (VI) with (III) and with (VII); (d) reaction of (VIII) with (V) and with (VII); or (e) reaction of (VIII) with (VI) and with (VII) in the presence of ammonia. The compounds (I) are useful due to their antagonist activity of the platelet activating factor.Type: GrantFiled: December 27, 1991Date of Patent: January 5, 1993Assignee: Alter, S.A.Inventors: Carlos Sunkel, Miguel Fau De Casa-Juana, Luis Santos, Pilar Ortega, Jaime Priego, Mariano Sanchez-Crespo
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Patent number: 5162345Abstract: Compounds are described of the formula: ##STR1## and physiologically acceptable salts thereof, in which R.sub.1 -R.sub.7 are defined hereinafter.The compounds represented by formula (I) reduce intracellular calcium ion concentration by limiting transmembranal calcium ion concentration and thus may be useful for the treatment of cardiovascular disorders such as hypertension.Type: GrantFiled: August 20, 1990Date of Patent: November 10, 1992Assignee: Glaxo, S.p.A.Inventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Alan D. Borthwick
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Patent number: 5158963Abstract: A 1,4-dihydropyridine derivative having the formula (I): ##STR1## wherein X is oxygen atom or nitrogen atom; when X is oxygen atom, R.sup.1 is hydrogen atom, a lower alkyl group, a lower cycloalkyl group, a lower alkenyl group or magnesium atom, when X is nitrogen atom, X-R.sup.1 group is NH.sub.2, NHR.sup.1', NR.sup.1' R.sup.1" or ##STR2## in which R.sup.1' is a lower alkyl group or a lower alkoxyalkyl group, R.sup.1" is a lower alkyl group and n is an integer of 2 to 6; R.sup.2 is a lower alkyl group, a lower cycloalkyl group or a lower alkoxyalkyl group and R.sup.3 is a lower alkyl group, formyl group, dimethoxymethyl group, cyano group or amino group, when X is oxygen atom and R.sup.1 is hydrogen atom or magnesium atom, R.sup.3 is methyl group, when X is nitrogen atom, R.sup.3 is methyl group, or a pharmaceutically acceptable salt thereof, some processes for preparing the same and a pharmaceutical composition containing the same.Type: GrantFiled: July 26, 1990Date of Patent: October 27, 1992Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Michio Nakanishi, Katsuhiro Uchida, Terutake Nakagawa, Kiyoharu Ukai, Michiko Nagahara, Jun Nakano, Kazuhiko Kimura
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Patent number: 5142057Abstract: A process for producing a carboxylic acid amide or 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 29, 1990Date of Patent: August 25, 1992Assignee: Nihon Nohyaku Co., Ltd.Inventors: Keiji Suto, Masaaki Kudo, Moriharu Yamamoto
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Patent number: 5142055Abstract: Processes for production of 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds, useful as herbicides and as intermediates which provide herbicides.Type: GrantFiled: October 4, 1990Date of Patent: August 25, 1992Assignee: Monsanto CompanyInventor: Len F. Lee
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Patent number: 5138091Abstract: Cardioactive dihydropyridines of the formula ##STR1## in which Y is ##STR2## A is H or CH.sub.3, B is --NH, --NH--CO--, --NH--CS--, --NH--COO--, --NH--SO.sub.2 --or --NH--CO--NH-- or --NH--CS--NH--, andR.sup.13 and R.sup.14 each independently is H or an organic radical,and salts thereof. The Y can be hydrolyzed off. The other radicals on the dihydropyridine moiety can also be varied.Type: GrantFiled: November 9, 1990Date of Patent: August 11, 1992Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Martin Bechem, Rainer Gross, Siegbert Hebisch, Matthias Schramm
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Patent number: 5126457Abstract: The invention is directed to processes for the preparation of dimethyl-1,4-dihydro-2,6-dimethyl-4-(2'-nitrophenyl)-pyridine-3,5-dicarbox ylate by reacting 1-methoxy-1-(2'-nitrophenyl)-N-(2'-nitrophenyl)methylene methanamie or 1-(2'-nitrophenyl)-N,N'-bis-(2'-nitrophenyl) methylene methanediamine with methyl acetoacetate in the presence of an amine compound or by reacting the monomeric or trimeric from of 2-nitrobenzaldimine with methyl acetoacetate.Type: GrantFiled: March 8, 1989Date of Patent: June 30, 1992Assignee: Egis GyogyszergyarInventors: Pal Benko, Daniel Bozsing, Laszlo Levai, Gyorgyi Kovanyi nee Lax, Gyorgy Mikite, Peter Tompe, Eva Furdyga, Ilona Dinnyes nee Nagy, Eva Poczik, Gyorgyi Zalavari nee Dosa, Ivan Beck, Istvan Simonyi, Kalman Nagy, Janos Imre, Erzsebet Kiss nee Bertok, Eva J. Tajthy nee Juhasz, Attila Mandi, Frigyes Gorgenyi
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Patent number: 5124456Abstract: Novel dihydropyridine compounds bearing substituted piperidyl substituents are effective heat/light stabilizers for a wide variety of polymer substrates, e.g., for halopolymers such as PVC, and are also effective anti-UV agents and antioxidants for such polymers as polyolefins, polystyrenes, polyalkadienes, polyurethanes, polyamides, polyesters, polycarbonates, polysulfones, polyethersulfones, polyetherketones, acrylic polymers, or copolymers or mixtures thereof.Type: GrantFiled: October 2, 1990Date of Patent: June 23, 1992Assignee: Rhone-Poulenc ChimieInventors: Louis Carette, Michel Gay, Sylvie Lavault, Gilles Mur
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Patent number: 5122608Abstract: There is provided a process for the preparation of a substituted or unsubstituted 2,3-pyridine or quinolinedicarboxylic acid by hydrolysis of a substituted or unsubstituted 2,3-pyridine or quinolinedicarboxylic acid diester with an acid having an ionization constant pK.sub.a of less than 3.0 followed by isolation of the product as the free acid or an acid salt.Type: GrantFiled: December 19, 1990Date of Patent: June 16, 1992Assignee: American Cyanamid CompanyInventor: Henry L. Strong
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Patent number: 5120849Abstract: O-substituted hydroxylamines (I)H.sub.2 N--O--CH.sub.2 --R(I)where R is H or an organic radical, and their salts are prepared by reacting a cyclic imidoether II of a 1,4- or 1,5-dicarboxylic acid, the said imidoether containing an ether group --O--CH.sub.2 --R, with a basic compound by a method in which a primary aliphatic aminoalcohol III is used as the basic compound and the compound I is, if required, converted to its salts.Type: GrantFiled: January 9, 1991Date of Patent: June 9, 1992Assignee: BASF AktiengesellschaftInventors: Jochen Wild, Norbert Goetz, Wolfgang Will, Rolf-Dieter Kohler, Peter Plath
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Patent number: 5118809Abstract: 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 appropiately substituted .alpha.,.beta.-unsaturated aldehyde or ketone.Type: GrantFiled: June 15, 1990Date of Patent: June 2, 1992Assignee: American Cyanamid CompanyInventors: Albert A. Cevasco, George A. Chiarello, William F. Rieker
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Patent number: 5106987Abstract: Described herein is a process for preparation of substituted pyridine dicarboxylate compounds.Type: GrantFiled: February 8, 1991Date of Patent: April 21, 1992Assignee: Monsanto CompanyInventors: William H. Miller, Mitchell J. Pulwer
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Patent number: 5099024Abstract: A process for dehydrofluorination of a 2,6-(bis)trifluoromethyl-dihydropyridine-3,5-dicarbothioic acid ester.Type: GrantFiled: March 19, 1990Date of Patent: March 24, 1992Assignee: Monsanto CompanyInventors: Mitchell J. Pulwer, William Miller, Sherrol L. Baysdon
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Patent number: 5099023Abstract: A process for dehydrofluorination of a 2,6-(bis) trifluoromethyl-dihydropyridine-3,5-dicarbothioic acid ester.Type: GrantFiled: March 19, 1990Date of Patent: March 24, 1992Assignee: Monsanto CompanyInventors: William Miller, Mitchell J. Pulwer
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Patent number: 5091395Abstract: Compounds are described of the formula ##STR1## wherein R.sub.1 and R.sub.4 independently represent a C.sub.1-4 alkyl group;R.sub.2 and R.sub.3 independently represent a C.sub.1-6 straight or branched alkyl chain or alkoxy group;R.sub.5 represents a straight or branched chain C.sub.1-13 alkyl group or a C.sub.5-8 cycloalkyl group which may be substituted by a C.sub.1-3 alkyl substituent;R.sub.6 represents a halogen atom or a straight or branched C.sub.1-3 alkyl group.The compounds represented by formula (I) reduce intracellular calcium ion concentration by limiting transmembranal calcium ion reflux and thus may be useful for the treatment of cardiovascular disorders such as hypertension.Type: GrantFiled: November 4, 1988Date of Patent: February 25, 1992Assignee: Glaxo S.p.A.Inventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Alan D. Borthwick
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Patent number: 5089624Abstract: The present invention relates to 1,4-dihydropyridine of the formula(I) ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted by one or two substituents selected from halogeno, nitro, trifluoromethyl and difluoromethoxy group, or 2,1,3-benzoxadiazole-4-yl group, R.sup.2 represents a lower alkyl or phenyl group, R.sup.3 represents a lower alkyl group and Y represents an oxygen or sulfur atom.The compounds of the formula(I) can be employed for treatment or prevention of cardiovascular diseases.Type: GrantFiled: October 6, 1989Date of Patent: February 18, 1992Assignee: Yuhan CorporationInventors: Choong S. Kim, Jung J. Suh, Bong Y. Lee, Chang S. Kim, Jong W. Lee, Byung C. Kim, Byung H. Han
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Patent number: 5089168Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: May 16, 1989Date of Patent: February 18, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Reinhard Hopf, Volker Reiffenrath, Eike Poetsch, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 5079366Abstract: The invention provides novel amino acids and peptides containing them which comprise a dihydropyridine.revreaction.pyridinium salt-type redox system and which provide site-specific and sustained delivery of pharmacologically active peptides to the brain. These new amino acids contain a redox system appended directly or via an alkylene bridge to the carbon atom adjacent to the carboxyl carbon and may be incorporated into a peptide chain at a variety of positions, including non-terminal positions.Type: GrantFiled: October 4, 1989Date of Patent: January 7, 1992Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5075324Abstract: 1,4-dihydropyridines of formula I ##STR1## wherein X is --CO.sub.2 R.sub.1, cyano, nitro, --COCH.sub.3 ; each of R and R.sub.1, which are the same or different, is a primary, secondary or tertiary, saturated or unsaturated, linear or branched C.sub.1 -C.sub.6 alkyl group optionally substituted by one or more hydroxy, C.sub.1 -C.sub.7 -monoalkylamino, di-C.sub.1 -C.sub.7 -alkylamino, benzylamino, C.sub.1 -C.sub.6 -alkoxy, phenoxy groups which are optionally substituted; R.sub.2 is hydrogen; R.sub.3 is hydrogen or hydroxy, --OCOR.sub.5, OSO.sub.2 R.sub.6, azide, amino, --NHPO(OR.sub.7).sub.2, --NHCOR.sub.5, C.sub.1 -C.sub.4 -alkoxy or fluorine, chlorine, bromine or iodine, SH, SCOR.sub.6 or C.sub.1 -C.sub.6 -alkylthio, phenylthio or benzylthio; R.sub.4 is an optionally substituted aromatic or an optionally substituted 5- or 6-membered heteroaromatic group; Y is one or more substituents, which may be the same or different, selected from C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.Type: GrantFiled: June 22, 1989Date of Patent: December 24, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Andrea Zaliani, Carmelo A. Gandolfi, Mauro Germini, Odoardo Tofanetti, Sergio Tognella
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Patent number: 5070204Abstract: Described herein is a process for preparation of substituted pyridine dicarboxylate compounds.Type: GrantFiled: March 19, 1990Date of Patent: December 3, 1991Assignee: Monsanto CompanyInventors: William Miller, Mitchell J. Pulwer
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Patent number: 5068337Abstract: The invention concerns compounds of formula ##STR1## or salts thereof; wherein Ar is an optionally substituted aryl radical;R represents hydrogen or an optionally substituted alkyl or aralkyl group;R.sup.1 and R.sup.2 are the same or different and are selected from hydrogen and saturated or unsaturated, cyclic or acyclic aliphatic hydrocarbon residues optionally substituted by one or more groups selected from halogen, OH, carboxy, CN, alkoxy, alkylthio, aryloxy, alkoxycarbonyl, amino, substituted amino, and optionally substituted aryl;A represents a group of formula --XR.sup.3 whereinX is (i) a group of formula --(CHR.sup.6).sub.p --Y--(CHR.sup.7).sub.q --or (ii) a group of formula --(CHR.sup.6).sub.r --O--(CHR.sup.7).sub.qin which formulae: Y represents --S--, NR.sup.8 or a direct bond, p and q each represent 0, 1 or 2 providing that p and q do not both represent 0, 1 or 2 and the other is zero; R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen or lower alkyl, and R.sup.Type: GrantFiled: November 13, 1986Date of Patent: November 26, 1991Assignee: John Wyeth & Brother LimitedInventors: John L. Archibald, Terence J. Ward, Albert Opalko
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Patent number: 5063239Abstract: Circulation active compounds of the formula ##STR1## in which R.sup.1 is phenyl or heterocyclyl substituted by nitro, trifluoromethyl or other radicals,R.sup.2 is optionally substituted alkyl or other radicalR.sup.3 and R.sup.5 are hydrogen, methyl or other radicals,R.sup.4 is hydrogen or optionally substituted alkyl,X is from 2 to 15, andR.sup.6 is ##STR2## and physiologically acceptable salts thereof.Type: GrantFiled: May 8, 1990Date of Patent: November 5, 1991Assignee: Bayer AktiengesellschaftInventors: Eckhard Schwenner, Hartmut Stegelmeier, Stanislav Kazda, Andreas Knorr
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Patent number: 5051433Abstract: Hypertension and cardiac insufficiency can be controlled by 4-nitrophenyl-dihydropyridine amides of the formula ##STR1## in which X can be ethylene or the like,Y is pyridyl or --NR.sup.9 R.sup.10, andR.sup.9 and R.sup.10 each independently is hydrogenor an organic group, or together form a ring, and physiologically tolerated salts thereof. Compounds in which R.sup.5 and R.sup.6 are not aryl or aralkyl are new.Type: GrantFiled: September 27, 1989Date of Patent: September 24, 1991Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Eckhard Schwenner, Rainer Gross, Siegbert Hebisch, Matthias Schramm, Martin Bechem, Claudia Hirth, Johannes-Peter Stasch
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Patent number: 5051432Abstract: Compounds are described of the formula ##STR1## wherein R.sub.1 and R.sub.4 independently represent a C.sub.1-4 alkyl group:R.sub.2 represents a group ##STR2## (where A is a bond or a methylene group and R.sub.7 is phenyl C.sub.1-4 alkyl; or R.sub.2 represents a group CH.sub.2 CH.sub.2 NR.sub.8 R.sub.9 (where R.sub.8 is hydrogen or C.sub.1-4 alkyl and R.sub.9 is C.sub.1-4 alkyl, phenyl C.sub.1-4 alkyl or benzoyl C.sub.1-4 alkyl); or R.sub.2 represents a C.sub.1-4 alkyl group substituted by nitrile.R.sub.3 represents a C.sub.1-6 straight or brached alkyl chain or alkoxy group;R.sub.5 represents a straight or branched chain C.sub.1-13 alkyl group or a C.sub.5-8 cycloalkyl group which may be substituted by a C.sub.1-3 alkyl substituent;R.sub.6 represents a halogen atom or a straight or branched C.sub.1-3 alkyl group.Type: GrantFiled: September 19, 1990Date of Patent: September 24, 1991Assignee: Glaxo, S.p.A.Inventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Alan D. Borthwick
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Patent number: 5047414Abstract: Compounds of formula I, and pharmaceutical compositions containing compounds of formula I ##STR1## wherein: R.sub.1 is:(a) COCH.sub.3, COC.sub.6 H.sub.5, CN or NO.sub.2 ;(b) COORa wherein Ra is hydrogen, or optionally substituted C.sub.1 -C.sub.6 straight or branched alkyl;R.sub.2 is optionally substituted phenyl; pentafluorophenyl; .alpha.- or .beta.-naphthyl; a five- or six-membered heterocyclic ring; .alpha.-benzo[2,3-b]-1,4-dioxan-.alpha.-yl; or .alpha.-benzofuroxanyl;R.sub.3 is COORa;P is hydrogen, --(CH.sub.2).sub.p --W, or C.sub.1 -C.sub.8 linear or branched alkyl;N--P.sub.1 is the residue of a primary or secondary amino group wherein P.sub.1 is hydrogen, C.sub.1 -C.sub.6 lower linear or branched alkyl group, or --(CH.sub.2).sub.p --W; and P, taken together with P.sub.1 and the nitrogen atom to which P.sub.1 is linked, may form a pyrrolidine or a piperidine ring; W is hydroxymethyl, formyloxymethyl, CO.sub.2 R wherein R is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: December 21, 1990Date of Patent: September 10, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sergio Tognella
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Patent number: 5047543Abstract: A 1,4-dihydropyridine derivative represented by the formula ##STR1## wherein X is a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms, A and B are the same or different and are each an alkylene group having 1 to 4 carbon atoms, and a pharmaceutically acceptable salt thereof are useful as the preventive and therapeutical agents of ischemic heart disease and hypertension.Type: GrantFiled: November 17, 1989Date of Patent: September 10, 1991Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Toshihisa Ogawa, Tomomi Ota, Shuichi Sato, Takemi Sunaga, Yoshiaki Watanabe, Katsuo Hatayama
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Patent number: 5047542Abstract: A novel method is disclosed for the preparation of 2,3-pyridine-dicarboxylates by the reaction of a ketoester such as dimethyl oxalacetate with an .alpha.,.beta.-unsaturated aldehyde or ketone such as 2-ethylacrolein and at least 1 molar equivalent of ammonium salt in suitable solvent.Type: GrantFiled: July 1, 1988Date of Patent: September 10, 1991Assignee: Hoechst Celanese CorporationInventors: B. Franklin Gupton, James H. Rea, Werner H. Mueller, John Saukaitis
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Patent number: 5039674Abstract: Novel 1,4-dihydropyridine derivatives and salts thereof are provided, which can be represented by the formula ##STR1## wherein, Y represents an oxygen atom or a sulfur atom; A represents an alkylene group, an alkenylene group or an alkynylene group; and R.sup.7 and R.sup.8 can represent individual groups or may be combined together with a nitrogen atom(s) to form a pyrrole ring, a piperidine ring, a morpholine ring or a piperazine ring or azepine ring which may be substituted with a lower alkyl group or an aralkyl group. Pharmaceutical compositions containing the derivatives and their use for imparting calcium antagonistic activity are also provided.Type: GrantFiled: January 12, 1990Date of Patent: August 13, 1991Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Takashi Fujikura, Yuzo Matsumoto
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Patent number: 5034533Abstract: Polymer matrices, e.g., halogenated polymers such as PVC, polyolefins, polystyrenes, polyalkadiences, etc., are stabilized against the adverse effects of heat and light, by incorporating therein an effective stabilizing amount of a compound of the formula (I): ##STR1## in which n is a number ranging from 1 to 3, and R is a methyl radical or a hydrogen atom.Type: GrantFiled: May 31, 1990Date of Patent: July 23, 1991Assignee: Rhone-Poulenc ChimieInventors: Michael Gay, Sylvie Lavault
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Patent number: 5034395Abstract: Dihydropyridine derivatives and salts thereof represented by the general formula, ##STR1## which possess excellent calcium antagonist effect, hypotensive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phophodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.Type: GrantFiled: February 24, 1987Date of Patent: July 23, 1991Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Shigeharu Tamada, Kazuyoshi Nagami, Shuji Teramoto, Tatsuyoshi Tanaka, Kazuyuki Nakagawa
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Patent number: 5026863Abstract: The invention relates to new compounds of formula I: ##STR1## in which Ar represents a phenyl radical having one to five identical or different substituents selected from chloro or fluoro,Y, Z, Y.sub.1 and Z.sub.1, which may be identical or different, each represents a hydrogen atom, a straight-chain or branched lower alkyl radical containing 1 to 4 carbon atoms, a cyclopropyl radical, a dicyclopropylmethyl radical, a 2,2-dicyclopropylethyl radical, a 2,2-dicyclopropylethenyl radical, a 3,3-dicyclopropylpropyl radical, a 3,3-dicyclopropyl-1-propenyl radical, a straight-chain or branched alkenyl radical containing 2 to 5 carbon atoms or a phenyl radical substituted with a nitro radical,W represents a straight-chain or branched lower alkyl radical containing 1 to 4 carbon atoms,V represents an oxygen atom,U represents a methyleneoxy radical or an ethyleneoxy radical,m and n, which may be identical or different, each represents an integer which may take a value from 2 to 4, inclusive, R.sub.1 and R.sub.Type: GrantFiled: May 2, 1990Date of Patent: June 25, 1991Assignee: Adir et CompagnieInventors: Jean L. Peglion, Yves M. Gargouil, Jean P. Vilaine
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Patent number: 5021436Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is an alkoxycarbonyl group, acetyl, benzoyl, cyano, nitro or aminocarbonyl;R.sub.2 is an optionally substituted aryl or hetaryl group;R.sub.3 is an alkoxycarbonyl group;.phi. is a thio residue such as alkylthio, cycloalkylthio, arylthio, heteroarylthio, aminoalkylthio,are described.Compounds I are useful in human therapy as antihypertensive, antiulcer, antithrombotic, antiischaemic agents.Type: GrantFiled: September 28, 1989Date of Patent: June 4, 1991Assignee: Boehringer Mannheim Italia, S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sengio Tognella
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Patent number: 5017590Abstract: Cardioactive dihydropyridines of the formula ##STR1## in which Y is ##STR2## A is H or CH.sub.3, B is --NH, --NH--CO--, --NH--CS--, --NH--COO--, --NH--SO.sub.2 --or --NH--CO--NH-- or --NH--CS--NH--, andR.sup.13 and R.sup.14 each independently is H or an organic radical,and salts thereof. The Y can be hydrolyzed off. The other radicals on the dihydropyridine moiety can also be varied.Type: GrantFiled: June 15, 1989Date of Patent: May 21, 1991Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Martin Bechem, Rainer Gross, Siegbert Hebisch, Matthias Schramm
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Patent number: 5011848Abstract: Compounds are described of the formula ##STR1## wherein R.sub.1 and R.sub.4 independently represent a C.sub.1-4 alkyl group;R.sub.2 and R.sub.3 independently represent a C.sub.1-6 straight or branched alkyl chain which may be interrupted by an oxygen atom;R.sub.5 represents a straight or branched chain C.sub.1-13 alkyl group or a C.sub.5-8 cycloalkyl group which may be substituted by a C.sub.1-3 alkyl substitutent;The compounds represented by formula (I) reduce intracellular calcium ion concentration by limiting transmembranal calcium ion influx and thus may be useful for the treatment of cardiovascular disorders such as hypertension.Type: GrantFiled: January 23, 1989Date of Patent: April 30, 1991Assignee: Glaxo, S.p.A.Inventors: Claudio Semeraro, Dino Micheli, Daniele Pieraccioli, Giovanni Gaviraghi, Allan D. Borthwick
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Patent number: 5010201Abstract: A new process has been found for the preparation of substituted 2-chloropyridine derivatives of the formula (I) ##STR1## wherein R.sup.1 to R.sup.4 have the meanings as defined in the description.The new process is characterized in that pyridine 1-oxides of the formula II ##STR2## are reacted with a chlorine-containing phosphoric acid derivative from the series of the chlorophosphoric esters and chlorophosphoramides in the presence of an inert organic solvent and in the presence of an acid acceptor at temperatures between -20.degree. C. and 200.degree. C., and the resulting product is separated further, if appropriate.Compound (I) is known as an intermediate product for medicaments (cf.DE-A 2,812,585) or for insecticidel nitromethylene derivatives (cf. EP-A 163,855).Type: GrantFiled: November 1, 1989Date of Patent: April 23, 1991Assignee: Bayer AktiengesellschaftInventors: Dieter Kaufmann, Bernd Gallenkamp
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Patent number: 5008276Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 4999362Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is an alkoxycarbonyl group, acetyl, benzoyl, cyano, nitro or aminocarbonyl;R.sub.2 is an optionally substituted aryl or hetaryl group;R.sub.3 is an alkoxycarbonyl group;.phi. is a thio residue such as alkylthio, cycloalkylthio, arylthio, heteroarylthio, aminoalkylthio,are described.Compounds I are useful in human therapy as antihypertensive, antiulcer, antithrombotic, antiischaemic agents.Type: GrantFiled: April 4, 1989Date of Patent: March 12, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4996320Abstract: A pyridine-compound is reacted with fluorine together with a Bronsted 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: January 9, 1989Date of Patent: February 26, 1991Assignee: Sagami Chemical Research CenterInventors: Teruo Umemoto, Kyoichi Tomita, Kosuke Kawada, Ginjiro Tomizawa
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Patent number: 4994476Abstract: A series of compounds useful in treating cardiovascular disorders due to the combined expression of both .beta.-block and calcium-block activity by these agents. This useful combination of actions is effected by a novel combination of structural subunits forming these compounds. Essentially, .beta.-blocking aryloxypropanolamine moieties are attached via their aryl ring or amino nitrogen at one of the carboxylate groups of calcium-blocking 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates. These compounds are prepared from new 4-aryl-1,4-dihydropyridine intermediate compounds.Type: GrantFiled: September 23, 1985Date of Patent: February 19, 1991Assignee: Bristol-Myers CompanyInventor: Graham S. Poindexter
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Patent number: 4988717Abstract: 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: March 30, 1989Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Friedrich Bosseret, Wulf Vater, Robertson Towart, Kurt Stoepel, Stanislav Kazda
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Patent number: 4988713Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is a cyano, nitro, acetyl, benzoyl or alkoxycarbonyl group;R.sub.2 is an optionally substituted phenyl or heteroaryl group;R.sub.3 is an alkoxycarbonyl group;R.sub.4 is an alkyl group, optionally substituted by hydroxy, amino, phenyl, heterocyclic group; an optionally substituted phenyl group or an heterocyclic group.Compounds I are useful in human therapy as agents able to interact with CA.sup.++ -dependent systems and as anti-tumor agents.Type: GrantFiled: September 7, 1989Date of Patent: January 29, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Carmelo A. Gandolfi, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4983740Abstract: The invention relates to a process for producing new compounds of formula I: ##STR1## and isomers thereof, as well as acid addition salts thereof, in which the symbols have the meanings set forth in the specification.Type: GrantFiled: July 27, 1989Date of Patent: January 8, 1991Assignee: Adir et CompagnieInventors: Jean L. Peglion, Yves M. Gargouil, Jean P. Vilaine
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Patent number: 4971984Abstract: Compounds of formula I ##STR1## wherein R.sub.1 is a cyano, nitro, benzoyl, acetyl, amido or alkoxycarbonyl group;R.sub.2 is substituted aryl- or heterocyclic residue;R.sub.3 is alkoxycarbonyl group;R.sub.4 and R.sub.5, being the same or different, are hydrogen, alkyl, aryl or heterocyclic groups;Y is oxygen, sulphur or substituted or unsubstituted nitrogen atom, that can be a part of a heterocyclic ring;n is 0, 1 or 2R6 and R.sub.10, that can be the same or different, are: hydrogen; C.sub.1 -C.sub.6 -alkyl optionally substituted by hydroxy, amino, monoalkyl and dialkylamino, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.3 -carbonyloxy, aryl, heteroaryl and cycloalkyl; a C.sub.1 -C.sub.12 -alkanoyl, aroyl or heteroaryl group optionally substituted by halogen, nitro, amino monoalkylamino, dialkylamino, hydroxy, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.3 -carbonyloxy, aryl, heteroaryl, cycloalkyl groups.Type: GrantFiled: December 10, 1987Date of Patent: November 20, 1990Assignee: Beehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Andrea Zaliani, Carlo Riva, Carmelo Gandolfi, Odoardo Tofanetti, Sergio Tognella
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck