Patents Examined by D. Springer
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Patent number: 5610296Abstract: The invention herein is directed to a process for producing a lactam of the formula ##STR1## from a methionine analog of the formula ##STR2## by treating the methionine analog with trimethylsulfonium halide or trimethylsulfoxonium halide in the presence of a base in a suitable aprotic solvent.The invention herein is further directed to the preparation of amidinophenyl pyrrolidinyl .beta.-alanine urea analogs using such methionine and lactam compounds as intermediates, which .beta.-alanine urea analogs are useful as antithrombotics.Type: GrantFiled: December 5, 1994Date of Patent: March 11, 1997Assignee: G. D. Searle & Co.Inventors: Norman A. Abood, Daniel L. Flynn, Scott A. Laneman, Roger Nosal, Lori A. Schretzman
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Patent number: 4617310Abstract: 5-Oxo-2-pyrrolidinepropanoic acids, base addition salts, esters and amides are useful as agents for the reversal of amnesia. Pharmaceutical compositions containing said compounds and methods for using said compositions for treating senility and reversal of amnesia are also taught.Type: GrantFiled: August 15, 1985Date of Patent: October 14, 1986Assignee: Warner-Lambert CompanyInventor: Donald E. Butler
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Patent number: 4598155Abstract: There are described novel compounds of the formula I ##STR1## wherein the symbols R.sub.1, R.sub.2, R.sub.3, R.sub.7 and A have the meanings defined in claim 1, also processes for producing them and their use as dyes for dyeing and printing textile materials, on which are obtained brilliant, deeply colored, blue dyes, particularly on polyester materials.Type: GrantFiled: November 15, 1982Date of Patent: July 1, 1986Assignee: Ciba-Geigy CorporationInventor: Jean-Marie Adam
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Patent number: 4547509Abstract: Compounds of the structure ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, acylamino, dialkyl amino, trihalomethyl, halogen, nitro, hydroxy or cyano;X is in the 5, 6 or 7 position and is O(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3, S(CH.sub.2).sub.n or (CH.sub.2).sub.n ;Y is O(CH.sub.2).sub.n, S(CH.sub.2).sub.n, N(CH.sub.2).sub.n --R.sub.3 where R.sub.3 is H, alkyl or (CH.sub.2).sub.n ;R.sub.2 is monosubstituted or independently disubstituted H, hydroxy, alkyl, halogen, nitro, alkoxy, carboxyl, alkylcarboxy, trihalomethyl, cyano, trifluoromethyl, dialkylamino or acylamino;Z is O, S or (NR.sub.3).sub.2 where R.sub.3 is H, alkyl or aryl; andn is 0 to 10 inclusiveuseful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: January 3, 1983Date of Patent: October 15, 1985Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland
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Patent number: 4415495Abstract: The present invention provides 5,6;8,9-tetrahydro-7H-dibenz(d,f)azonine derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2, which are the same or different, are hydrogen or halogen atoms or lower alkyl or alkoxy radicals, R.sup.3 is a hydrogen atom or a lower alkyl radical, R.sup.4 is a hydrogen atom or a lower alkyl or alkanoyl radical and n is 1 or 2; and the pharmaceutically acceptable salts thereof formed with inorganic and organic acids; but excluding 6-benzyl-2,12-dimethoxy-1-hydroxy-7-methyl-5,6;8,9-tetrahydro-7H-dibenz(d, f)azonine in which case R.sup.1, R.sup.2 and R.sup.4 are hydrogen, n is 1 and R.sup.3 is methyl. The lower alkyl, alkanoyl and alkoxy radicals are straight chained or branched radicals containing 1 to 5 carbon atoms.The present invention also provides a process for the preparation of these compounds, as well as pharmaceutical compositions containing them.Type: GrantFiled: February 24, 1981Date of Patent: November 15, 1983Assignee: Godecke AktiengesellschaftInventors: Gerhard Satzinger, Manfred Herrmann, Edgar Fritschi, Heinrich Bahrmann, Volker Ganser, Bernd Wagner, Wolfgang Steinbrecher
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Patent number: 4401818Abstract: 1-Carboxy-(alkanoyl or aralkanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acids, e.g., those of the formula ##STR1## R=H, alkyl, alkoxy, halogeno or CF.sub.3 ; R'=H or R-phenyl;m=0 or 1;p,q=0 to 2;and functional derivatives thereof, are antihypertensive and cardioactive agents.Type: GrantFiled: December 24, 1980Date of Patent: August 30, 1983Assignee: Ciba-Geigy CorporationInventor: Norbert Gruenfeld
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Patent number: 4393218Abstract: A process for preparing 2,2-dialkyl-4-methyl-5,5-dialkyl-3-formyl-.DELTA..sup.3 -pyrrolines by reacting the corresponding dialkyl substituted di-tert-propargylamines with water at a pH equal to or less than 3.0. Preferably, an inorganic mercury compound is used as a catalyst.Type: GrantFiled: December 7, 1981Date of Patent: July 12, 1983Assignee: Anic, S.p.A.Inventors: Silvestro Costanzi, Francesco Tessarolo, Maurizio Brunelli
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Patent number: 4389405Abstract: Compounds having the following general formula: ##STR1## wherein R is an alkyl or aminoalkyl group having 1 to 8 carbon atoms, or a hydrogen atom; R.sub.2 and R.sub.3 are either hydrogen atoms or, together, an additional carbon-carbon bond, as well as the mineral or organic acid addition salts thereof. These compounds are used as anti-arhythmic agents.Type: GrantFiled: January 7, 1981Date of Patent: June 21, 1983Assignee: Omnichem, S.A.Inventor: Jean A. Hannart
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Patent number: 4386212Abstract: The present invention provides a process for the preparation of 5-(4'-chloro-5'-sulfamoyl-2'-thenylamino)-phenyltetrazole by condensing 5-(4'-chloro-5'-sulfamoyl-2'-aminophenyl)-tetrazole with thiophene-2-aldehyde in the presence of an acid catalyst and reducing the 5-[4'-chloro-5'-sulfamoyl-2'-(thenylidene-2-amino)-phenyl]tetrazole so obtained with a boranate, wherein the condensation is carried out in dimethyl sulfoxide as solvent, with azeotropic distilling off of the water formed and the reduction is carried out in the same medium, without isolation of the 5-[4'-chloro-5'-sulfamoyl-2'-(thenylidene-2-amino)-phenyl]-tetrazole.Type: GrantFiled: August 4, 1981Date of Patent: May 31, 1983Assignee: Boehringer Manheim GmbHInventors: Friedrich Batz, Karl Lauer
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Patent number: 4384125Abstract: In a distillation process 2-pyrrolidones obtained from succinonitrile are purified by treating the impure liquid pyrrolidone with a strong base, fractionally distilling this product to yield, as distillate, polymerization grade purified 2-pyrrolidone, mixing the 2-pyrrolidone-containing residue from the fractional distillation with water and an acid, and extracting purified 2-pyrrolidone from the water/acid mixture. The latter purified 2-pyrrolidone products are suitable for recycling to the pyrrolidone synthesis or to make other products.Type: GrantFiled: June 9, 1981Date of Patent: May 17, 1983Assignee: Stamicarbon, B.V.Inventors: Reijer Goettsch, Arnold G. M. Jetten
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Patent number: 4366313Abstract: Prostaglandin E (PGE)-type derivatives and analogs having a 6-keto feature are disclosed, including processes for preparing them and the appropriate intermediates, said derivatives having pharmacological activity.Type: GrantFiled: August 27, 1979Date of Patent: December 28, 1982Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4289888Abstract: The present invention relates to novel 2-decarboxy-2-tetrazolyl-4-halo-5,9-epoxy-9-deoxy-PGF.sub.1 compounds, which are intermediates useful for the preparation of corresponding 5,9.alpha.-epoxy-9-deoxy-PGF.sub.1 and 5,9-epoxy-9-deoxy-4,5-didehydro-PGF.sub.1 compounds. These end products are employed for induction of a variety of prostacyclinlike pharmacological effects. Accordingly, these end products are useful pharmacological agents for the same purposes for which prostacyclin is employed.Type: GrantFiled: September 7, 1979Date of Patent: September 15, 1981Assignee: The Upjohn CompanyInventor: Roy A. Johnson
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Patent number: 4115389Abstract: N-Alkyl allylic tertiary amines are dealkylated as illustrated by treatment of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline in cold methylene chloride with m-chloroperbenzoic acid followed by the addition of aqueous ferrous chloride to provide a good yield of (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline with substantial if not complete retention of optical activity. The product is an intermediate in a synthesis of the analgesic known as butorphanol.Type: GrantFiled: May 2, 1977Date of Patent: September 19, 1978Assignee: Bristol-Myers CompanyInventor: Ivo Monkovic