Pyridine Or Partially Hydrogenated Pyridine Rings Are Bonded Directly To Each Other Patents (Class 546/257)
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Patent number: 4818766Abstract: The invention relates to novel 1,4-dihydropyridine-3-carboxylic acid phenoxyaliphatylphenyleneoxyalkyl esters of the formula ##STR1## in which Ac represents an acyl group, X represents oxy or optionally substituted imino, A represents a divalent aliphatic hydrocarbon radical interrupted by a group --X.sub.1 --Ph--X.sub.2 -- in which at least one of the radicals X.sub.1 and X.sub.2 represents oxy and a radical X.sub.1 or X.sub.2 that is other than oxy represents a direct bond, and Ph represents an optionally substituted phenylene radical, and R represents an optionally substituted phenyl, pyridyl or 1-oxidopyridyl, (1,3-dioxa)indanyl or benzofurazanyl radical, R.sub.1 represents an optionally substituted phenyl or indolyl radical, R.sub.2 represents an aliphatic hydrocarbon radical and R.sub.3 represents an aliphatic radical, cyano or amino, and acid addition salts thereof.Type: GrantFiled: July 20, 1987Date of Patent: April 4, 1989Assignee: Ciba-Geigy CorporationInventors: Franz Ostermayer, Markus Zimmermann
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Patent number: 4814457Abstract: The invention is a complex-forming polymer comprising at least one aryl group having a 2,2'-bipyridine complex-forming moiety or a 1,10-phenanthroline complex-forming moiety. The complex-forming polymers are prepared by contacting a substituted 2,2'-bipyridine or a substituted 1,10-phenanthroline compound with a metalating agent, and then reacting the metalated compound with an halomethylated polystyrene polymer, or alternatively, reacting the metalated compound with at least one vinylbenzyl halide and subsequently polymerizing the reaction product. The complex-forming polymers are hydrolytically stable and may be used as polymeric ligands as such or complexed with selected metal compounds.Type: GrantFiled: December 23, 1986Date of Patent: March 21, 1989Assignee: Shell Oil CompanyInventor: Johan Stapersma
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Patent number: 4808722Abstract: Pyridinylurea N-oxides of the formula ##STR1## and acid addition salts thereof; wherein R is cycloalkyl (C.sub.3 -C.sub.8), alkenyl (C.sub.3 -C.sub.8), or an alkyl (C.sub.1 -C.sub.6) group optionally substituted with halogen, hydroxy, cycloalkyl (C.sub.3 -C.sub.8) alkoxy (C.sub.1 -C.sub.6), dialkyl (C.sub.1 -C.sub.6)amino or phenyl; R.sup.1 is hydrogen or alkyl (C.sub.1 -C.sub.6); R and R.sup.1 together with the nitrogen atom of the NRR.sup.1 group optionally define a nonaromatic heterocycle containing 4 to 6 ring carbon atoms; each X independently is halogen, alkyl (C.sub.1 -C.sub.6), haloalkyl (C.sub.1 -C.sub.6), alkoxy (C.sub.1 -C.sub.6), hydroxy, 2-pyridinyl, alkyl(C.sub.1 -C.sub.6)thio or alkyl (C.sub.1 -C.sub.6)sulfonyl; A is 1 to 4; and wherein the NHCONRR.sup.1 group is bonded to the pyridinyl ring in the 3- or 4-position. The compounds are useful in agriculture as plant growth regulators.Type: GrantFiled: October 31, 1985Date of Patent: February 28, 1989Assignee: FMC CorporationInventor: Robert N. Henrie, II
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Patent number: 4801722Abstract: There are described stable fluorescent labels comprising a complex of lanthanide metal and a chelating agent comprising a nucleus which is a triplet sensitizer having a triplet energy greater than that of said lanthanide metal and at least two heteroatom-containing groups which form coordinate complexes with lanthanide metals and a third heteroatom-containing group or heteratom in or appended to the triplet sensitizer. Labeled physiologically active materials useful in specific binding assays such as labeled antigens, heptens, antibodies, hormones and the like comprising the stable fluorescent labels having physiologically active materials adsorbed or bonded thereto are also described.Type: GrantFiled: January 27, 1987Date of Patent: January 31, 1989Assignee: Eastman Kodak CompanyInventors: Jerald C. Hinshaw, John L. Toner, George A. Reynolds
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Patent number: 4787931Abstract: N-phenyl-N'-(pyridinyl-N-oxide)ureas of the formula ##STR1## and their use as plant regulators are disclosed and exemplified.Type: GrantFiled: June 17, 1986Date of Patent: November 29, 1988Assignee: FMC CorporationInventors: Robert Henrie, II, Christine M. Green, Robert E. Sticker
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Patent number: 4786641Abstract: Blood-sugar-lowering dihydropyridines of the formula ##STR1## in which R.sup.1 represents phenyl, naphthyl, thienyl, pyridyl, chromenyl or thiochromenyl, it being possible for the radicals mentioned each to carry up to 2 identical or different substituents from the series comprising halogen, alkyl, alkoxy and alkylthio with in each case up to 6 carbon atoms, fluoroalkyl and fluoroalkoxy with in each case up to 3 carbon atoms and 3 fluorine atoms, nitro and cyano,R.sup.2 represents straight-chain, branched or cyclic alkyl which has up to 8 carbon atoms, can be interrupted in the alkyl chain by an oxygen or a sulphur atom and can be substituted by halogen, phenyl, cyano, hydroxyl, amino, alkylamino or dialkylamino with in each case up to 3 carbon atoms per alkyl group or by N-benzylmethylamino,R.sup.Type: GrantFiled: August 20, 1987Date of Patent: November 22, 1988Assignee: Bayer AktiengesellschaftInventors: Siegfried Goldmann, Hans-Jurgen Ahr, Walter Puls, Hilmar Bischoff, Dieter Petzinna, Klaus Schlossmann, Joachim Bender
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Patent number: 4786646Abstract: The invention relates to compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is ##STR2## or --(CH.sub.2).sub.k -- wherein k is an integer from 0 to 4, R.sub.3, R.sub.4 and R.sub.8 are independently hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.Type: GrantFiled: July 10, 1987Date of Patent: November 22, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4782071Abstract: Certain tetrasubstituted alkyl, aryl, pyridinyl, piperidinyl, and piperazinyl urea compounds stimulate the release of acetylcholine and are thus useful analgesic agents for alleviating pain or as cholinergic agents which are useful for the amelioration of the symptoms of cognitive decline in the elderly.These compounds have the general formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.4 are phenyl or substituted phenyl, and R.sub.3 is pyridinyl.Pharmaceutical compositions including these compounds as well as methods for the preparation of the compounds are also disclosed.Type: GrantFiled: November 3, 1986Date of Patent: November 1, 1988Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, David M. Lustgarten, Walter H. Moos, Anthony J. Thomas
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Patent number: 4780538Abstract: A process for the preparation of 1,4-dihydropyridine compounds, especially N-substituted 1,4-dihydropyridine compounds, is disclosed. The compounds are useful as cardiovascular agents and also as starting materials for the preparation of certain cyclized compounds which have properties as calcium entry blockers.Type: GrantFiled: February 12, 1986Date of Patent: October 25, 1988Assignee: Merck & Co., Inc.Inventors: Steven M. Pitzenberger, Barry M. Trost
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Patent number: 4771057Abstract: Pharmaceutical compounds of the general formula (1): ##STR1## have been prepared and non-toxic pharmaceutically acceptable salts thereof, wherein the ring system is a 1,2- or 1,4-dihydropyridyl radical; R.sub.1 is a hydrogen, lower alkyl, lower alkyl carbonyl or lower alkoxy carbonyl substituent; R.sub.2 is a lower alkly or phenyl substituent; R.sub.3 is a lower alkoxy carbonyl, (N,N-lower dialkylamino) lower alkoxy carbonyl, (N-lower alkyl-N-phenyl lower alkyl amino) lower alkoxy carbonyl, lower alkoxy lower alkoxy carbonyl, nitro, or cyano substituent; R.sub.Type: GrantFiled: February 3, 1986Date of Patent: September 13, 1988Assignee: University of AlbertaInventors: Edward E. Knaus, Michael W. Wolowyk, Lina Dagnino, Moy C. Li-Kwong-Ken, Donald A. Soboleski, Hla Wynn
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Patent number: 4764516Abstract: Pure enantiomers of 5-nitrodihydropyridine of the formula ##STR1## are mixed, wherein one of the enantiomers has a high vasodilative action and a low negative inotropic activity on heart muscle, the other enantiomer has a low vasoconstrictive action and a high positive inotropic activity on heart muscle, the mixture being high in vasodilative activity and in positive inotropic activity on heart muscle.Type: GrantFiled: December 6, 1985Date of Patent: August 16, 1988Assignee: Bayer AktiengesellschaftInventors: Gerhard Franckowiak, Rolf Grosser, Gunter Thomas, Matthias Schramm, Rainer Gross
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Patent number: 4760088Abstract: Sulfide derivatives of catechins derived from condensed tannins have broad spectrum biocidal characteristics. Epicatechin-4-alkylsulfides and cupric complexes thereof containing up to 20, preferably 5 to 15, carbon atoms are particularly effective biocides against wood rotting fungi and gram-positive bacteria.Such sulfides are prepared by reacting condensed tannin, either in the form of a purified tannin extract or comminuted plant tissue, with an appropriate thiol under mild acidic conditions.Type: GrantFiled: September 15, 1986Date of Patent: July 26, 1988Assignee: Board of Control of Michigan Technological UniversityInventor: Peter E. Laks
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Patent number: 4737506Abstract: This invention relates to a 1,4-dihydropyridine-3,5-dicarboxylate derivative represented by the following general formula (I): ##STR1## wherein R means an imidazolyl or pyridyl group, R.sub.1 denotes a hydrogen or halogen atom or a nitro or trifluoromethyl group, R.sub.2 is a lower alkyl group, X is CH or N, A means a lower alkylene group, ##STR2## B being a lower alkylene or O-lower alkylene group, ##STR3## R.sub.4 being a hydrogen atom or lower alkyl group, or ##STR4## m denotes a number of 1-3, and n stands for 1 or 2. The derivative has vasodilative effects, hyperkinemic effects, platelet aggregation inhibitory effects, thromboxane A.sub.2 formation inhibitory effects and so on, and are hence useful as a pharmaceutical product such as vasodilator, antihypertensive, antithrombotic agent, antiarteriosclerotic agent or the like.Type: GrantFiled: April 7, 1986Date of Patent: April 12, 1988Assignee: Kowa Co., Ltd.Inventors: Noboru Shimizu, Hiroyuki Ishiwata, Tomio Ohta, Hiroshi Ishihama, Yasumi Uchida
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Patent number: 4732982Abstract: This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.Type: GrantFiled: February 28, 1986Date of Patent: March 22, 1988Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Winton D. Jones, Richard A. Schnettler, Richard C. Dage
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Patent number: 4710500Abstract: The present invention relates to novel indole derivatives which have interesting pharmacodynamic effects indicating pronounced activity in the treatment of psychic disorders, especially psychoses and, at the same time, a low degree of undesired side effects.Moreover, the invention relates to methods for the preparation of said indole derivatives, pharmaceutical compositions containing same, and methods for the treatment of psychic disorders, especially psychoses, by administering a therapeutically active amount of one of said derivatives to a living animal body, including human beings.The novel indole derivatives of the present invention are represented by the following formula: ##STR1## wherein R is phenyl, optionally substituted with halogen, lower alkyl or trifluoromethyl, or a hetero aromatic group, such as 2-thienyl, 3-thienyl, 2-furoyl, 3-furoyl, 2-thiazol, 2-oxazol, 2-imidazole, 2-pyridyl, 3-pyridyl or 4-pyridyl; R.sup.Type: GrantFiled: April 1, 1986Date of Patent: December 1, 1987Assignee: H. Lundbeck A/SInventor: Jens K. Perregaard
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Patent number: 4705794Abstract: Pyridinecarboxylic acid esters of the formula ##STR1## in which R is an optionally substituted aryl or heterocyclic radical,R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, aralkyl, acyloxyalkyl or hydroxyalkyl, or R.sup.1 with X forms a carbonyl-containing heterocyclic ring,X is --CN, --CO--R.sup.4, --COOR.sup.5 or --SO.sub.2 R.sup.6,R.sup.4, R.sup.5 and R.sup.6 are various optionally substituted radicals, andR.sup.3 is different from R.sup.5 and is a substituted or interrupted hydrocarbon radical,or pharmaceutically acceptable salts thereof control the otherwise negative effects of ischaemia and/or hypoxia.Type: GrantFiled: February 28, 1983Date of Patent: November 10, 1987Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Ulrich Benz
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Patent number: 4698352Abstract: This invention relates to a novel 4-oxo-1,4-dihydronicotinic acid derivative ##STR1## or a salt thereof, wherein R.sup.1 is hydrogen or carboxyl-protecting group;R.sup.2 is substituted phenyl and naphthyl, or a substituted or unsubstituted heterocyclic group; andR.sup.3 is haloalkyl, aminoalkyl, or substituted or unsubstituted alkenyl, phenylalkenyl, naphthylalkenyl, phenylalkyl, naphthylalkyl, phenylalkynyl, naphthylalkynyl, heterocyclic alkyl, heterocyclic alkenyl, phenyl, naphthyl, cycloalkyl, cycloalkenyl, carboxylic acyl, iminoalkyl, heterocyclic or bridged hydrocarbon, which has a broad antibacterial spectrum and a low toxicity, and are useful for treatment of diseases of human beings and animals, to a process for producing the same and to an antibacterial agent containing the same.Type: GrantFiled: October 27, 1983Date of Patent: October 6, 1987Assignee: Toyama Chemical Co., Ltd.Inventors: Hirokazu Narita, Yoshinori Konishi, Jun Nitta, Shunjiro Misumi, Hideyoshi Nagaki, Isao Kitayama, Yoriko Nagai, Yasuo Watanabe, Nobuyuki Matsubara, Shinzaburo Minami, Isamu Saikawa
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Patent number: 4672118Abstract: Corrosion of metal surfaces in contact with an aqueous medium is inhibited by incorporating a N-(hydrophobe aromatic)pyridinium compound such as N-(p-dodecylphenyl)-2,4,6-trimethylpyridinium sulfoacetate into the aqueous medium.Type: GrantFiled: January 9, 1984Date of Patent: June 9, 1987Assignee: The Dow Chemical CompanyInventors: Thomas E. Fisk, Christopher J. Tucker
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Patent number: 4665174Abstract: A process for preparing cyclopentenone derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted ar(lower)alkyl and A is the residue of a nucleophilic agent from which a hydrogen atom is excluded, which comprises reacting a 3-hydroxy-4-cyclopentenone compound of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above with a nucleophilic agent of the formulaA--H (III)wherein A is as defined above.The cyclopentenone derivatives of the formula (I) are useful as pharmaceuticals, agricultural chemicals, perfumes and as intermediates for the preparation of agricultural chemicals, pharmaceuticals and perfumes.Type: GrantFiled: May 11, 1982Date of Patent: May 12, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Tadashi Katsura
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Patent number: 4622332Abstract: Compounds of the formula ##STR1## in which R is an optionally substituted aryl or heterocyclic radical,R.sup.1 is a hydrocarbon radical which is optionally interrupted by 1 oxygen atom in the chain, and/or which is optionally substituted,R.sup.4 is an aliphatic hydrocarbon radical having 7 to 14 carbon atoms, which is optionally interrupted by one oxygen atom and/or which is optionally substituted,R.sup.2 and R.sup.3 each independently is hydrogen, an alkyl radical, an aryl radical or an aralkyl radical, or, for the case where one of the substituents R.sup.2 or R.sup.3 has the above-mentioned meaning, the other is hydroxymethyl, acetoxymethyl or amino, andX is N-R.sup.5, wherein R.sup.5 is hydrogen, an alkyl radical which is optionally interrupted by an oxygen atom, a morpholinoalkyl radical, an aryl radical or an aralkyl radical orX is an oxygen atom, when one of the radicals R.sup.2 or R.sup.3 denotes an amino group,or pharmaceutically acceptable acid addition salts thereof, exhibit hypotensive activity.Type: GrantFiled: February 22, 1983Date of Patent: November 11, 1986Assignee: Bayer AktiengesellschaftInventors: Egbert Wehinger, Horst Meyer, Andreas Knorr
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Patent number: 4618607Abstract: 1,4-Dihydropyridine-3,5-dicarboxylic acid ester derivatives of the general formula: ##STR1## or acid addition salts thereof, wherein W is --CH.dbd. or --N.dbd.; Y is --CH.dbd.CH--, --O--, --S--, --CH.dbd.N(O)p-- (p is zero or 1) or --N(R)-- (R is hydrogen or lower alkyl); X.sup.1, X.sup.2 and X.sup.3 are the same or different, and are each hydrogen, halogen, nitro, trifluoromethyl, cyano or lower alkylthio; Z is aryl or 5- or 6-membered aromatic heterocyclic ring (which may have a substituent or two or three substituents which may be the same or different, and the substituent may be halogen, lower alkyl, lower alkoxy, lower alkanoylamino, cyano, nitro, lower alkylthio, trifluoromethyl, sulfamoyl, di-lower alkylsulfamoyl, amino or di-lower alkylamino); ##STR2## is 5- to 7-membered heterocyclic ring which may have nitrogen atom, oxygen atom, sulfur atom or unsaturated bond on the ring, and may be substituted by lower alkyl, lower alkoxycarbonyl, lower alkanoylamino, ethylenedioxy or --(CH.sub.2).sub.m --OR.sup.Type: GrantFiled: December 10, 1982Date of Patent: October 21, 1986Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Kazuhiko Araki, Hideki Ao, Jun Inui, Kenichi Aihara
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Patent number: 4618686Abstract: Process for the dehalogenation of aryl and alpha-araliphatic halides comprising contacting the aryl halide or alpha-araliphatic halide with hypophosphite salt, in the presence of a catalytic amount of a noble metal catalyst. This process is useful in the field of organic synthesis and for the removal of environmentally hazardous aryl and alpha-araliphatic halides, including polychlorinated biphenyls and dibenzo-p-dioxins.Type: GrantFiled: September 27, 1984Date of Patent: October 21, 1986Assignee: Ciba-Geigy CorporationInventor: Stephen K. Boyer
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Patent number: 4616002Abstract: Compounds of the formula I ##STR1## in which n represents 1, 2 or 3, Ar represents a carbocyclic or heterocyclic aryl radical, Ac represents the acyl radical of an acid, Z represents a radical --OR.sub.7 or --NR.sub.8 R.sub.9, R.sub.1 represents hydrogen, unsubstituted or substituted lower alkyl, a carbocyclic or heterocyclic aryl radical or free, etherified or esterified hydroxy, R.sub.2 and R.sub.3, independently of one another, each represents hydrogen, unsubstituted or substituted lower alkyl, formyl or functionally modified formyl, carboxy or functionally modified carboxy, a carbocyclic or heterocyclic aryl radical or unsubstituted or mono- or di-substituted amino, R.sub.4 represents hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently of one another, each represents hydrogen, unsubstituted or substituted lower alkyl or a carbocyclic or heterocyclic aryl radical, R.sub.7, R.sub.8 and R.sub.Type: GrantFiled: January 6, 1986Date of Patent: October 7, 1986Assignee: Ciba-Geigy CorporationInventors: Bruno Kamber, Thomas Leutert, Hans Kuhnis, Kurt Eichenberger
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Patent number: 4616024Abstract: 1,4-Dihydropyridine derivatives of the formula: ##STR1## wherein 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; Y is --(CH.sub.2).sub.n --, --CH.sub.2 CH(CH.sub.3)-- or --CH.sub.2 C(CH.sub.3).sub.2 --; n is 1 to 3; and X is a 5 or 6 membered nitrogen containing aromatic heterocyclic ring which may optionally be substituted by one or more C.sub.1 -C.sub.4 alkyl, phenyl, benzyl, CN, --N(R.sup.3).sub.2, (CH.sub.2).sub.m CO.sub.2 H, (CH.sub.2).sub.m CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or (CH.sub.2).sub.m CON(R.sup.3).sub.2 group wherein each R.sup.3 is independently H or C.sub.1 -C.sub.4 alkyl and m is 0 or 1; and their pharmaceutically acceptable acid addition salts, and pharmaceutical preparation containing such compounds, have utility as anti-ischaemic and antihypertensive agents.Type: GrantFiled: February 21, 1985Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Simon F. Campbell, Peter E. Cross, John K. Stubbs
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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: 4558058Abstract: 1,4-dihydropyridines of the formula I ##STR1## in which R denotes, for example, --CO.sub.2 R.sup.3 or cyano, R.sup.1 denotes, for example, an optionally substituted phenyl, pyridyl or thienyl, R.sup.2 denotes the radical of a 5-membered, optionally substituted, ring having at least one double bond and at least 2 heteroatoms or heteroatom groups from the series comprising O, N, NH and S, and R.sup.3 denotes, for example, alkyl or alkoxyalkyl, and their acid addition salts, have valuable pharmacological properties.Type: GrantFiled: December 9, 1983Date of Patent: December 10, 1985Assignee: Cassella AktiengesellschaftInventors: Karl Schonafinger, Helmut Bohn, Melitta Just, Piero Martorana
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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: 4549022Abstract: The invention relates to 4-pyridone-3-carboxylic acid derivatives, a process for the preparation thereof and pharmaceutical compositions containing same. The 4-pyridone-3-carboxylic acid derivatives are useful as antibacterial agents and/or as agents having a stimulating activity on the central nervous system.Type: GrantFiled: November 2, 1984Date of Patent: October 22, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Alexander E. Wick
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Patent number: 4521535Abstract: The invention relates to 4-pyridone-3-carboxylic acid derivatives, a process for the preparation thereof and pharmaceutical compositions containing same. The 4-pyridone-3-carboxylic acid derivatives are useful as antibacterial agents and/or as agents having a stimulating activity on the central nervous system.Type: GrantFiled: April 19, 1982Date of Patent: June 4, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Alexander E. Wick
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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: 4508719Abstract: Compounds of formula I: ##STR1## are described in which R.sup.1 is a linear or branched alkyl radical containing between 1 and 5 carbon atoms, the alkyl radical being unsubstituted or substituted by an alkoxy group; R.sup.2 is an unsubstituted phenyl of phenyl substituted by a nitro group; R.sup.3 is hydrogen or a linear or branched alkyl residue containing between 1 and 4 carbon atoms, the alkyl radical being unsubstituted or substituted by at least one alkoxy or fluorine atom or both alkoxy and fluorine atoms; R.sup.4 is hydrogen or a linear or branched alkyl containing between 1 and 4 carbon atoms, the alkyl radical being unsubstituted or substituted by alkoxy, carbalkoxy, dialkylamino, 1-aryl or 1-heteroarylpiperazinyl, aryl or a monocyclic 5 or 6 membered heterocycle in which at least one of the heteroatoms is N,O,S such as 1-piperidinyl, 4-morpholinyl or R.sub.4 is alkenyl or cyclo(C.sub.3 -C.sub.Type: GrantFiled: May 26, 1983Date of Patent: April 2, 1985Assignee: Pierrel S.p.A.Inventors: Silvia Z. Tricerri, Cesare Casagrande, Franco De Marchi, Massimo Nicola
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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: 4497808Abstract: The present invention relates to novel N-oxide compounds that have cardiovascular properties, especially antihypertensive activity, and that correspond to the formula ##STR1## in which Py represents an unsubstituted or substituted N-oxidopyridyl radical, R.sub.1 represents hydrogen or unsubstituted or substituted lower alkyl, one of the radicals R.sub.2 and R.sub.3 represents lower alkyl and the other represents hydrogen; lower alkyl; lower alkyl containing free, etherified or esterified hydroxy, oxo, functionally modified carboxy or free or substituted amino or imino; functionally modified carboxy; or free or substituted amino, it being possible for an amino group R.sub.2 or R.sub.3 to be bonded to a lower alkyl radical R.sub.1 or, if R.sub.2 or R.sub.3 represents, for example, hydroxy-lower alkyl, for this hydroxy-lower alkyl, together with the adjacent acyl radical Ac.sub.1 or Ac.sub.Type: GrantFiled: December 27, 1982Date of Patent: February 5, 1985Assignee: Ciba-Geigy CorporationInventors: Markus Zimmermann, Hans Kuhnis
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Patent number: 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: 4469696Abstract: The invention relates to 4-,5-and 6-substituted 2-amino pyridines of Formula (I) and methods for their preparation. Also included in the invention are compositions containing said 2-amino pyridines of Formula (I) and the use of said compounds and compositions for use inter alia, as lipid absorption inhibitors.Type: GrantFiled: June 3, 1982Date of Patent: September 4, 1984Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Walter Puls, Hilmar Bischoff
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Patent number: 4463008Abstract: 2-(R.sub.1 O)-3-Q-5-PY-6-R-pyridine (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where R.sub.1 is methyl or ethyl, R is hydrogen or lower-alkyl, PY is 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, and Q is hydrogen, chloro or COOR' where R' is lower-alkyl, or Q is cyano only when R is hydrogen. The preparation of I and their cardiotonic use are shown.Type: GrantFiled: November 10, 1982Date of Patent: July 31, 1984Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Baldev Singh
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Patent number: 4448780Abstract: N-R.sub.1 -N-(6-R-5-PY-2-pyridinyl)ureas, where R.sub.1 is lower-alkyl, R is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof. Said compounds (I) or pharmaceutically acceptable acid-addition salts thereof are useful as cardiotonic agents. The preparation and cardiotonic use of said compounds are shown.Type: GrantFiled: September 3, 1982Date of Patent: May 15, 1984Assignee: Sterling Drug Inc.Inventor: George Y. Lesher
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Patent number: 4431651Abstract: 3,4-Dihydro-3-R.sub.1 -4-R.sub.2 -5-Q-6-R-2(1H)-pyridinones (I), where R.sub.1 and R.sub.2 are each hydrogen or methyl, R is lower-alkyl, and Q is 4(or 3)-hydroxyphenyl, 4(or 3)-methoxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof, and their preparation are shown. Also shown is the cardiotonic use of I where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents.Type: GrantFiled: November 18, 1982Date of Patent: February 14, 1984Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Baldev Singh, Philip M. Carabateas
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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: 4420617Abstract: 5-PY-6-Q-pyridin-2-amines (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where Q is hydrogen or lower-alkyl, and PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents. Their preparation from the corresponding 5-PY-6-Q-2(1H-pyridinones via the corresponding 2-halo-5-PY-6-Q-pyridines is shown.Type: GrantFiled: July 6, 1982Date of Patent: December 13, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4374141Abstract: Shown is a process for preparing cardiotonically active 1,3-dihydro-3-R-6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones, where Q is hydrogen or lower-alkyl, R is lower-alkyl, lower-hydroxyalkyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, by reacting a 2-RNH-5-PY-6-Q-nicotinamide with an alkali metal hypohalite. Also shown are cardiotonic compositions and a method for increasing cardiac contractility using 2-RR'N-5-PY-6-Q-nicotinamides or pharmaceutically acceptable acid-addition salts thereof, where R' is hydrogen or methyl. Also shown is the process for preparing said 2-RR'N-5-PY-6-Q-nicotinamides by reacting a 2-halo-5-PY-6-Q-nicotinamide with an amine of the formula RR'NH.Type: GrantFiled: August 17, 1981Date of Patent: February 15, 1983Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4365065Abstract: 1-R.sub.1 -3-[amino, cyano, carbamyl, halo, lower-alkylamino, di-(lower-alkyl)amino or lower-acylamino]-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones or pharmaceutically-acceptable acid-addition or cationic salts thereof are useful as cardiotonic agents, where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl. 1-R.sub.1 -3-amino-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones are prepared by hydrolyzing the corresponding 3-cyano compounds to produce the corresponding 3-carbamyl compounds and reacting the latter with a reagent capable of converting carbamyl to amino. The 1-R.sub.1 -3-cyano-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones are prepared by reacting (pyridinylmethyl) lower-alkyl ketones with dimethylformamide di-(lower-alkyl) acetal to produce 1-(pyridinyl)-2-(dimethylamino)ethenyl lower-alkyl ketone and reacting said ketones with N-R.sub.1 -o-cyanoacetamide to produce the 1-R.sub.1 -3-cyano-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones.Type: GrantFiled: September 3, 1981Date of Patent: December 21, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Richard E. Philion
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Patent number: 4363911Abstract: 1-R.sub.1 -1,2-dihydro-6-[2-(dimethylamino)ethenyl]-2-oxo-5-PY-nicotinonitriles, where R.sub.1 is hydrogen or methyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, or pharmaceutically acceptable acid-addition salts thereof are useful as cardiotonic agents. Said compounds are prepared by reacting 1,2-dihydro-6-methyl-2-oxo-5-PY-nicotinonitrile with dimethylformamide dimethylacetal. Shown is the cardiotonic use of said compounds or pharmaceutically acceptable acid-addition salts thereof.Type: GrantFiled: September 3, 1981Date of Patent: December 14, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Ruth P. Brundage
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Patent number: 4362734Abstract: Shown are cardiotonically active 2-RR'N-5-PY-6-Q-nicotinonitriles where R is methyl or ethyl, R' is hydrogen or methyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, and Q is hydrogen or methyl, the latter only when R' is hydrogen, or pharmaceutically acceptable acid-addition salts thereof. Also shown are cardiotonic compositions and a method for increasing cardiac contractility using as active components 2-RR'N-5-PY-6-Q-nicotinonitriles or pharmaceutically acceptable acid-addition salts thereof, where R, R', PY and Q are defined as above. Also shown is the process for preparing said 2-RR'N-5-PY-6-Q-nicotinonitriles by reacting a 2-halo-5-PY-6-Q-nicotinonitrile with an amine of the formula RR'NH.Type: GrantFiled: August 26, 1981Date of Patent: December 7, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
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Patent number: 4362735Abstract: 1-R.sub.1 -3-[(1-Methyl-3-oxo-1-butenyl)amino or (3-oxo-1-butenyl)amino]-5-PY-6-R-2(1H)-pyridinones, where R.sub.1 is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and R is hydrogen or lower-alkyl, or pharmaceutically acceptable acid-addition salts thereof are useful as cardiotonic agents. The preparation and cardiotonic use of said compounds are shown.Type: GrantFiled: August 31, 1981Date of Patent: December 7, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Ruth P. Brundage
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Patent number: 4361569Abstract: 3-(Hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically acceptable acid-addition salt thereof is useful as a cardiotonic agent. 3-Hydroxy-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by autoclaving a mixture of a sodium or potassium lower-alkoxide, a lower-alkanol and 3-(chloro or bromo)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone and acidifying the reaction mixture. 3-Hydroxymethyl-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone is prepared by reacting 6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone with excess formaldehyde at an acidic pH. Said 3-(hydroxy or hydroxymethyl)-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone or pharmaceutically acceptable acid-addition salt thereof is disclosed as the active ingredient in cardiotonic compositions for increasing cardiac contractility and in the method for increasing cardiac contractility in a patient requiring such treatment.Type: GrantFiled: August 26, 1981Date of Patent: November 30, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Richard E. Philion
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Patent number: 4339584Abstract: N-Hydroxy-1-R.sub.1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinimidamides or pharmaceutically-acceptable acid-addition salts thereof, useful as cardiotonic agents, are prepared by reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-PY-6-R-nicotinonitriles with hydroxylamine and are converted by reaction with polyphosphoric acid to the corresponding cardiotonically useful 1-R.sub.1 -3-amino-5-PY-6-R-2(1H)-pyridinones, where R.sub.1 is hydrogen, lower-alkyl and lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.Type: GrantFiled: May 11, 1981Date of Patent: July 13, 1982Assignee: Sterling Drug Inc.Inventors: Monte D. Gruett, George Y. Lesher
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Patent number: 4331672Abstract: 2-[R.sub.1 NHN(R)]-3-Q'-5-Py-6-Q-pyridines or pharmaceutically-acceptable acid-addition salts thereof are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, Q' is hydrogen or halo, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and R.sub.1 is hydrogen or when R is other than hydrogen R.sub.1 is the same as R. These compounds are prepared by reacting a 2-halo-3-Q'-5-PY-6-Q-pyridine with R.sub.1 NHNHR where 2-halo is bromo or chloro. Also shown are: the use of said 2-[R.sub.1 NN(R)]-3-Q'-5-PY-6-Q-pyridines as cardiotonic agents; and, the intermediates, 2,3-dihalo-5-PY-6-Q-pyridines, and their preparation from 3-nitro-5-PY-6-Q-2(1H)-pyridinones.Type: GrantFiled: February 4, 1981Date of Patent: May 25, 1982Assignee: Sterling Drug Inc.Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page