Patents Examined by E. Bernhardt
  • Patent number: 5294711
    Abstract: This invention relates to 3,6-diamino-2,5-pyrazinedicarbonitrile which is a red crystal and yellowish green fluorescent substance and the methods of preparation from compounds represented by formula [I], ##STR1## (wherein R are aryl, alkyl, aralkyl or alkenyl or may be substituted), as a starting material, under acidic condition in the presence of oxygen.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: March 15, 1994
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Seiji Tazaki, Tomio Yagihara, Nobuo Matsui, Atsushi Yanagisawa, Takakazu Kojima
  • Patent number: 5278161
    Abstract: Compounds of the formula ##STR1## wherein A, B, X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are as set forth in the specification, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diasteromeric racemates as well as pharmaceutically acceptable salts thereof which inhibit the activity of the natural enzyme renin and are useful in the control or prevention of high blood pressure and cardiac insufficiency are described.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: January 11, 1994
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Quirico Branca, Marie-Paule Heitz, Marcel Muller, Werner Neidhart, Stadler Heinz, Eric Vieira, Wolfgang Wostl
  • Patent number: 5276035
    Abstract: A disubstituted piperazine compound having the formula ##STR1## wherein R.sup.1 is halogen, methoxy, C.sub.1-6 -alkyl or trifluoromethyl, and R.sup.2 is methyl or substituted C.sub.1-8 -alkyl, C.sub.3-8 -alkenyl or C.sub.3-8 -cycloalkyl, where substituents may be hydroxy-, keto- or oximino-groups in any position leading to a stable tertiary amine; or R.sup.2 is a straight or branched C.sub.1-8 -alkyl or C.sub.3-8 -alkenyl, which in any position may be substituted as above, but is terminally substituted with one of the following groups: cyano, optionally C.sub.1-4 -alkoxy-substituted C.sub.1-4 -alkoxy, dimethoxy, optiontionally substituted phenoxy, phosphonic acid, thienyl, furyl, oxazoline, isoxazole, oxadiazole, where the optional substitution is represented by C.sub.1-6 -alkyl or phenyl, provided that when cyano is the only substituent in R.sup.2, R.sup.2 must contain at least four carbon atoms, and pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: January 4, 1994
    Assignee: Novo Nordisk A/S
    Inventors: Rolf Hohlweg, Erling Guddal, Erik B. Nielsen
  • Patent number: 5270316
    Abstract: There are disclosed condensed purine derivatives represented by formula; ##STR1## in which R.sup.3 represents hydrogen, lower alkyl or benzyl; each of X.sup.1 and X.sup.2 independently represents hydrogen, lower alkyl, aralkyl or phenyl; and n is an integer of 0 or 1; R.sup.1 represents hydrogen, lower alkyl, alicyclic alkyl, noradamantan-3-yl, dicyclopropylmethyl or styryl; and R.sup.2 represents hydrogen, lower alkyl or alicyclic alkyl; or a pharmaceutically acceptable salt thereof. The derivatives and pharmaceutically acceptable salts are useful as diuretics, renal protecting agents, antiallergic agents and hypotensives.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: December 14, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Fumio Suzuki, Junichi Shimada, Takeshi Kuroda, Kazuhiro Kubo, Akira Karasawa, Tetsuji Ohno, Kenji Ohmori
  • Patent number: 5229387
    Abstract: Compounds of the formula ##STR1## wherein: m is an integer of 1-6;n is an integer of 1 or 2;X and Y are independently hydrogen; hydroxy; lower alkyl; lower alkoxy; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;R is ##STR2## wherein: R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl;R.sup.3 is hydrogen, lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or halo; and ##STR3## and pharmaceutically acceptable acid addition salts thereof. The compounds and salts exhibit useful pharmacological properties, including selective .alpha..sub.2 -adrenoceptor antagonist properties and 5-HT.sub.1A receptor partial agonist properties, and are particularly useful for the treatment of sexual dysfunction, depression and anxiety.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: July 20, 1993
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Robin D. Clark, Brian H. Vickery, Mike Spedding
  • Patent number: 5223623
    Abstract: This invention relates to novel 2-substituted-1(4)-aryl piperazines and to a process for their preparation. The compounds of this invention have been found to have cardiovascular, primarily antiarrhythmic effects.
    Type: Grant
    Filed: September 11, 1991
    Date of Patent: June 29, 1993
    Assignee: Schering AG
    Inventor: Gary B. Phillips
  • Patent number: 5220024
    Abstract: A process for the preparation of a compound of formula (A): ##STR1## wherein X is hydrogen, hydroxy, chloro, C.sub.1-6 alkoxy or phenyl C.sub.1-6 alkoxy and R.sub.a and R.sub.b are hydrogen, including acyl and phosphate derivatives thereof; which process comprises:i) the preparation of a compound of formula (I): ##STR2## wherein R.sub.1 is C.sub.1-6 alkyl, or phenyl C.sub.1-6 alkyl in which the phenyl group is optionally substituted; R.sub.2 is hydrogen, hydroxy, chlorine, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or amino; and R.sub.3 is halogen, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphonyl, azido, an amino group or a protected amino group, which process comprises the reaction of a compound of formula (II): ##STR3## with a compound of formula (VII): ##STR4## wherein Q is a leaving group, J is hydrogen or halo and R.sub.
    Type: Grant
    Filed: September 26, 1990
    Date of Patent: June 15, 1993
    Assignee: Beecham Group p.l.c.
    Inventors: Graham R. Geen, Trevor J. Grinter, Stephen Moore
  • Patent number: 5219857
    Abstract: Novel compounds of the formula ##STR1## wherein n is an integer from 1 to 4 inclusive; R.sub.1 represents a mono-or disubstituent of hydrogen, lower alkyl(C.sub.1 -C.sub.3), lower alkoxy(C.sub.1 -C.sub.3), halogen, nitro or trifluoromethyl; R.sub.2 is cyano, carboxamido, ethyl carboxylate or halogen; R.sub.3 is hydrogen, straight or branched chain lower alkyl(C.sub.1 -C.sub.3), alkenyl(C.sub.2 -C.sub.3), alkynyl(C.sub.2 -C.sub.3), cycloalkyl(C.sub.3 -C.sub.6), hydroxyalkyl(C.sub.1 -C.sub.3), dimethylaminoalkyl(C.sub.1 -C.sub.3), ethylcarboxylate, alkyl(C.sub.1 -C.sub.13)carbonyl, 1-(methylethyl)acetamide, cyclohexylethyl, phenyl, mono-or disubstituted phenyl (wherein the phenyl substituent is halogen, trifluoromethyl, lower alkyl(C.sub.1 -C.sub.3) or lower alkoxy(C.sub.1 -C.sub.3)), benzyl, mono-or disubstituted benzyl (wherein the benzyl substituent is halogen, lower alkyl(C.sub.1 -C.sub.3), lower alkoxy(C.sub.1 -C.sub.3) or trifluoromethyl), benzoyl, 4-methoxybenzoyl, straight or branched chain alkyl(C.sub.
    Type: Grant
    Filed: April 15, 1992
    Date of Patent: June 15, 1993
    Assignee: American Cyanamid Company
    Inventors: Shin S. Tseng, Herbert J. Brabander, Joseph W. Epstein
  • Patent number: 5218118
    Abstract: This invention provides smoking compositions which contain a novel flavorant-release additive.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: June 8, 1993
    Assignees: Philip Morris Incorporated, Philip Morris Products Inc.
    Inventors: W. Geoffrey Chan, Yoram Houminer
  • Patent number: 5214047
    Abstract: A tetracyclic quinazoline derivative of the formula I: ##STR1## wherein A is C.sub.2-3 -alkylene or C.sub.2-3 -alkylene which is substituted by one or two C.sub.1-4 -alkyl radicals or A is cyclohexylene; X is phenyl, naphthyl or phenyl or naphthyl which is substituted by halogen, nitro, amino, C.sub.1-4 -alkylamino, sulfonylamino, C.sub.1-4 -acylamino, hydroxyl, C.sub.1-4 -alkoxy, --O--(CH.sub.2).sub.2-4 --NR.sup.1 R.sup.2, C.sub.1-4 -alkyl or C.sub.1-4 -alkylsulfonyl, wherein R.sup.1 and R.sup.2 are each hydrogen or C.sub.1-4 -alkyl; or X is thienyl or thienyl which is substituted by chlorine, fluorine, methyl, ethyl, methoxy, ethoxy, nitro or hydroxyl; and R is hydrogen, halogen, nitro, amino, C.sub.1-4 -alkylamino, sulfonylamino, C.sub.1-4 -acylamino, hydroxyl, C.sub.1-4 -alkoxy, --O--(CH.sub.2).sub.2-4 --NR.sup.3 R.sup.4, C.sub.1-4 -alkyl or C.sub.1-4 -alkylsulfonyl, wherein R.sup.3 and R.sup.4 are each hydrogen or C.sub.1-4 -alkyl, and the pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: May 25, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Ostersehlt, Rainer Schlecker, Beatrice Rendenbach, Gerda von Philipsborn, Albrecht Franke, deceased
  • Patent number: 5212310
    Abstract: The present invention encompasses structures of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## and W, X, A, B, C, D, E, R.sub.3, R.sub.4 are variables. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine drugs, and enhancement of memory.
    Type: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Neurogen Corporation
    Inventors: Andrew Thurkauf, Alan Hutchison, Pamela Albaugh
  • Patent number: 5212309
    Abstract: Chemiluminescenct 3-aminobenzene-1,2,4,5-tetracarboxylic dihydrazides.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: May 18, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Schefczik, Klaus Huemke
  • Patent number: 5210261
    Abstract: Amine salts of phosphorothioic acids, useful for example in lubricant compositions, are made by forming a mixture of sulphur and an amine, and then adding a phosphite ester. The reaction is controlled by the rate of addition of the ester.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: May 11, 1993
    Assignee: Ethyl Petroleum Additives, Ltd.
    Inventors: Barrie D. James, Roger Scattergood
  • Patent number: 5207819
    Abstract: Disclosed is a novel compound of the formula [I]: ##STR1## (wherein R.sup.1 is H or CH.sub.3, R.sup.2 is H or C.sub.1 -C.sub.4 alkyl), furylmethyl group, tetrahydrofuryl group 2-tetrahydropyranylmethyl group or tetrahydrofurfuryl group which may be substituted with methyl group. The compound has strong herbicidal effect against the weeds belonging to the Family Gramineae.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: May 4, 1993
    Assignees: Agro-Kanesho Co., Ltd, Tosoh Corporation
    Inventors: Sinzo Someya, Seigo Koura, Mikio Ito, Yoichi Kitamura, Hiroyuki Watanabe, Kenji Tsuzuki
  • Patent number: 5207816
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a substituted or unsubstituted five-membered heteroaromatic radical, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, processes for their manufacture, and the use of these compounds for controlling undesirable plant growth.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: May 4, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
  • Patent number: 5206365
    Abstract: A series of psychotropic heterobicycloalkylpiperazine derivatives having the structure ##STR1## wherein V is a 3- or 4-membered unsaturated chain, containing all carbon atoms when 4-membered, or when a 3-membered chain, V contains an oxygen or sulfur atom as one of the members; R is H or C.sub.1-4 alkyl; W is CH, N, CH.sub.2, or a chemical bond; X is CH, N, SO.sub.2, or CO, with the proviso that both W and X cannot simultaneously be N; and Z is a heteroaromatic ring system. These compounds are useful antipsychotic and/or anxiolytic agents.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: April 27, 1993
    Inventors: James S. New, William L. Christopher
  • Patent number: 5198441
    Abstract: New derivatives of 1,2-dihydro 2-oxo quinoxalines corresponding to the general formula I: ##STR1## in which: R is a hydrogen or halogen atomR.sub.1 is a hydrogen atom or a straight or branched C.sub.1 -C.sub.4 alkyl radicalR.sub.2 is:a hydrogen atoma C(O)R.sub.4 radical in which R.sub.4 is a straight or branched C.sub.1 -C.sub.4 alkyl groupa C(O)NHR.sub.5 radical in which R.sub.5 is a straight or branched C.sub.1 -C.sub.4 alkyl radical or a phenyl groupA is a C.sub.1 -C.sub.4 alkaline chainR.sub.3 represents:a hydrogen atom, a C.sub.1 -C.sub.4 alkyl radical, a C.sub.3 -C.sub.6 cycloalkyl radical, an alcynyl, nitrile, hydroxyl, carboxamido, pyridyl, phenyl group, or a phenyl group substituted by a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group or a nitro groupan alkenyl radical of the formula: ##STR2## in which R.sub.6, R.sub.7 may, independently of each other, be a hydrogen atom, a C.sub.1 -C.sub.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: March 30, 1993
    Assignee: Pierre Fabre Medicament
    Inventors: Guy Pitet, Christian Faure, Francoise Couret, Dennis Bigg, Jean-Pierre Tarayre
  • Patent number: 5192763
    Abstract: [(1-Arylpyrrolidin-2-yl)methyl]piperazine compounds corresponding to the formula ##STR1## in which Z denotes a group of formula N-R.sub.1 in which R.sub.1 is either a hydrogen atom or a C.sub.1-3 alkyl group or a group of formula Ar--C.sub.n H.sub.2n in which n denotes 0, 1 or 2 and Ar denotes a phenyl group optionally substituted by one or more halogen atoms and/or C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals, or a group of formula COR.sub.2 in which R.sub.2 denotes the CH.sub.3, C.sub.6 H.sub.5, CH.sub.2 C.sub.6 H.sub.5 or OC.sub.2 H.sub.5 group and their salts of addition to pharmaceutically acceptable acids. The compounds are useful for the treatment of neurological disorders.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: March 9, 1993
    Assignee: Synthelabo
    Inventors: Pascal George, Jacques Menin, Jean-Pierre Merly, Dennis Bigg, Daniel Obitz, Michel Peynot, Corinne Veronique
  • Patent number: 5191081
    Abstract: A novel intermediate useful in the synthesis of ethylenediaminetriacetic acid (ED3A) or its salts. N,N'-ethylenediaminediacetic acid (ED2AH.sub.2) or a salt containing up to one equivalent of base cation is condensed with formaldehyde to form a stable 5-membered ring intermediate. The addition of cyanide across this cyclic material forms ethylenediamine N,N'-diacetic acid-N'-cyanomethyl or salts thereof (mononitrile-diacid), which is a useful intermediate in the production or ED3A. The nitrile in aqueous solutions may be spontaneously cyclized to form 2-oxo-1,4-piperazinediacetic acid (3KP) or salts thereof. In the presence of excess base, salts of ED3A are formed in excellent yield and purity.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: March 2, 1993
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Brian A. Parker
  • Patent number: 5187186
    Abstract: DC-88A derivatives represented by the general formula: ##STR1## wherein X represents hydrogen or CO.sub.2 R.sup.1 (in which R.sup.1 represents hydrogen, a straight-chain or branched alkyl having 1 to 4 carbon atoms, allyl, or benzyl); and ##STR2## have an excellent anti-tumor activity and are useful as anti-tumor agents.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: February 16, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Yutaka Kanda, Youichi Uosaki, Hiromitsu Saito, Hiroshi Sano, Eiji Kobayashi, Makoto Morimoto, Satoru Nagamura