The Five-membered Hetero Ring Contains One Double Bond Only (i.e., Indolines) Patents (Class 548/490)
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Patent number: 5717108Abstract: The present invention relates to a novel process for the preparation of a monohydroxyindole or dihydroxyindole compound by a single step of placing in contact, in a solvent medium, at least one hydrolase with at least one indole compound bearing one or two radicals connected by an ester function to the benzene ring.Type: GrantFiled: December 5, 1996Date of Patent: February 10, 1998Assignee: L'OrealInventors: Alain Lagrange, Michel Philippe, Remy Tuloup
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Patent number: 5708178Abstract: Novel acceptor-donor-acceptor and donor-acceptor-donor compounds for use in forming a thermally-stable electro-optic waveguide are disclosed. Also disclosed is a thermally stable waveguide material containing thermally stable acceptor-donor-acceptor or donor-acceptor-donor guest dipole compounds in a temperature-resistant polymer matrix. The waveguide has selected regions in which the net dipoles of the guest molecules are oriented, for electro-optic switching when an electric field is placed across these regions.Type: GrantFiled: September 20, 1996Date of Patent: January 13, 1998Assignee: Lockheed Martin CorporationInventors: Susan P. Ermer, Doris S. Y. Leung, Steven M. Lovejoy
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Patent number: 5688966Abstract: Novel intermediates having an indolenine nucleus which are useful in the synthesis of fluorescent sulfoindocyanine dyes are described. Dyes synthesized using such intermediates do not contain a reactive group that will covalently attach to a target molecule at an amine- or hydroxy-containing site. Rather, these intermediates are linked to an enzyme substrate or a member of a specific binding pair. Also included are tyramide-comaining sulfonidocyanine dyes.Type: GrantFiled: July 26, 1996Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Mark Norman Bobrow, Thomas Joseph Erickson
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Patent number: 5686616Abstract: A novel process for preparing an optically active amine by asymmetric hydrogenation of an imine compound, such as an imine compound prepared by condensing benzylamine and acetophenone, in the presence of a catalytic amount of an iridium-optically active phosphine complex and benzylamine or a benzylamine derivative. The present invention provides an optically active amine of high optical purity.Type: GrantFiled: March 14, 1996Date of Patent: November 11, 1997Assignee: Takasago International CorporationInventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
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Patent number: 5668271Abstract: Indolopyrrocarbazole derivatives represented by formula (I) and the pharmaceutically acceptable salts thereof have excellent antitumor activity as evidenced by their in vitro proliferation inhibiting activity against mouse leukemia cell, human gastric cancer cell, human lung cancer cell and human colon cancer cell, ##STR1## wherein R.sup.1 and R.sup.2 independently represent, for example, a hydrogen atom or various hydrocarbon groups which may be substituted or heterocyclic groups which may also be substituted; or a group --Y--R.sup.3 where Y represents a carbonyl group, thiocarbonyl group or sulfonyl group and R.sup.3 represents a hydrogen atom or one of various aliphatic, cycloaliphatic, aryl, nitrogen-containing (e.g. amino, hydrazino, etc) or heterocyclic groups, which groups may be substituted by various substituents; or R.sup.1 and R.sup.2 may combine to represent a lower alkylidene group which may be substituted; or R.sup.1 and R.sup.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Katsuhisa Kojiri, Hisao Kondo, Hiroharu Arakawa, Mitsuru Ohkubo, Hiroyuki Suda
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Patent number: 5663183Abstract: Compounds of the formula: ##STR1## in which R.sub.1 represents a hydrogen or halogen atom or a methyl or C.sub.1 -C.sub.4 alkoxy group, R'.sub.1 represents a hydrogen or halogen atom, R".sub.1 represents a hydrogen atom or a methoxy group, R.sub.3 represents a C.sub.1 -C.sub.3 alkyl group, R.sub.4 represents a 2,3-dihydro-1H-inden-2-yl, 2,3-dihydro-1H-inden-1-yl or 1,2,3,4-tetrahydronaphthalen-1-yl group, or R.sub.3 and R.sub.4 together form, with the adjacent nitrogen atom, a 1,2,3,4-tetrahydroisoquinol-2-yl, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinol-2-yl, 5,8-dimethoxy-1,2,3,4-tetrahydroisoquinol-2-yl, 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-2-yl, 1,2,3,4-tetrahydro-9H-pyrido[4,3-b]indol-3-yl, 4,5,6,7-tetrahydrothieno[2,3-c]pyrid-6-yl, 2,3-dihydro-1H-isoindol-2-yl or 2,3,4,5-tetra-hydro-1H-3-benzazepin-3-yl, group are useful in the treatment of cerebral disorders.Type: GrantFiled: May 24, 1996Date of Patent: September 2, 1997Assignee: SynthelaboInventors: Jonathan Frost, Pascal George, Patrick Pasau, Regine Bartsch, Corinne Rousselle, Paul Howard Williams, Jean Claude Muller
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1,2-ethanediol derivative and salt thereof and cerebral function-improving agent comprising the same
Patent number: 5658904Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.Type: GrantFiled: June 6, 1995Date of Patent: August 19, 1997Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita -
Patent number: 5646298Abstract: The present invention describes cyclopropylindole cytotoxic prodrugs of formulas (I), (II) and (III) as shown in the specification. The present invention is also directed to a method for the site-specific treatment of neoplastic diseases in a mammal which method includes the following steps: (i) administering to an afflicted mammal an effective amount of a targeting agent- enzyme donor peptide conjugate wherein the targeting agent is selected from the group of antibodies, monoclonal antibodies, adhesion molecules and tumor cell surface binding ligands; (ii) administering to the afflicted mammal an effective amount of an enzyme acceptor dimer thereby forming active enzymatic sites at a tumor cell surface; and (iii) administering to the afflicted mammal a therapeutically effective amount of an enzyme-activateable, cytotoxic pro-drug thereby releasing the cytotoxic drug at the tumor site.Type: GrantFiled: June 7, 1995Date of Patent: July 8, 1997Assignee: ProCoron, Inc.Inventor: Michael J. Powell
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Patent number: 5631381Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.Type: GrantFiled: June 28, 1996Date of Patent: May 20, 1997Assignee: Rhone-Poulenc Inc.Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
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Patent number: 5599774Abstract: Substituted N-arylindoles, a process for producing them and their use as herbicides. In particular, substituted N-arylindoles of the formula ##STR1## are disclosed in which: R is hydrogen; halogen; nitro; cyano; alkyl; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; carbonylalkoxy; alkyloxyalkoxy; cyanoalkoxy; benzyloxy; alkoxycarbonylalkoxy; alkylcarbonylalkoxy; haloalkyl; hydroxalkyl; formyl; azido; carboxy or its salts; COOalkyl; amino; substituted amino wherein the substituents are alkyl, alkoxy, hydroxy, formyl, alkylcarbonyl, substituted alkylcarbonyl substituted with carboxy or alkoxycarboxy, alkylsulfonyl, haloalkylsulfonyl, aminocarbonyl, (di)alkylaminocarbonyl, alkoxycarbonyl, alkoxyalkyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, amino or (di)alkyl amino; carboxyamido; substituted carboxyamido wherein said substituents can be selected from alkyl, alkylsulfonyl, and haloalkylsulfonyl; sulfonamido wherein the N is substituted with hydrogen and/or alkyl; YR.sup.4 wherein Y is O or S(O).sub.m and R.sup.Type: GrantFiled: December 31, 1992Date of Patent: February 4, 1997Assignee: Imperial Chemical Industries PLCInventors: Ferenc M. Pallos, Christopher J. Mathews
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Patent number: 5583234Abstract: An indoline product obtained by oxidizing at least one compound of formula (I), ##STR1## wherein R.sub.1 and R.sub.3 independently represent a hydrogen atom or a C.sub.1-4 alkyl grouping; R.sub.2 represents a hydrogen atom, a C.sub.1-4 alkyl grouping, a carboxyl grouping or C.sub.1-4 alkoxycarbonyl; R.sub.4 is a hydrogen atom, a C.sub.1-4 alkyl grouping, hydroxyl, C.sub.1-4 alkoxy, C.sub.1-10 amino or alkylamino, or halogen; R.sub.5 is a hydrogen atom, a hydroxyl grouping, C.sub.1-4 alkoxy or amino; with the proviso that at least one of the radicals R.sub.4 or R.sub.5 is a hydroxyl, alkoxy or amino grouping, and that when R.sub.5 is an amino grouping, R.sub.4 is not an alkylamino radical; R.sub.4 and R.sub.5 may also form a C.sub.1-2 alkylenedioxy ring and are in positions 5 and 6; and corresponding salts thereof. Said product may be used in cosmetics as make-up for the hair, eyebrows, eyelashes, nails, etc., and/or skin.Type: GrantFiled: December 29, 1993Date of Patent: December 10, 1996Assignee: L'OrealInventors: Alain Lagrange, Herv e Andrean, Alex Junino
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Patent number: 5578633Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: June 2, 1995Date of Patent: November 26, 1996Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5571727Abstract: A labelling color for detecting cocaine of Formula (I) ##STR1## wherein X represents a halogen, and a method of detecting methamphetamine, including the steps of adding a labelling color of Formula (II) ##STR2## wherein X represents an anion to a first solution of methamphetamine antibody to form a labelling color-methamphetamine antibody complex, measuring the fluorescence of the first solution, adding a sample containing an unknown amount of methamphetamine to the first solution to form a second solution, measuring the fluorescence of the second solution, and correlating any change in the fluorescence between the first and second solutions to the concentration of methamphetamine in the sample.Type: GrantFiled: October 7, 1994Date of Patent: November 5, 1996Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata
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Patent number: 5554642Abstract: A compound which is selected from those of formula (I): ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description,its optical isomers and its addition salts thereof with a pharmaceuticaliy-accepable acid or base,and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: May 22, 1995Date of Patent: September 10, 1996Assignee: Adir et CompagnieInventors: Michel Langlois, Pierre Renard, G erard Adam
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Patent number: 5502187Abstract: The pharmaceutically active bicyclic heterocyclic amines (XXX) ##STR1## where W.sub.1 is --N.dbd. or --CH.dbd.; W.sub.3 is --N.dbd. or --CH.dbd.; W.sub.5 is --N.dbd. or --CR.sub.5 -- with the proviso that W.sub.5 is --CR.sub.5 -- when both W.sub.1 and W.sub.3 are --N.dbd. which are useful as pharmaceuticals in treating mild and/or moderate to severe head injury, subarachnoid hemorrhage and subsequent ischemic stroke, asthma and reduction of mucous formation/secretion in the lung and other diseases and injuries.Type: GrantFiled: October 3, 1994Date of Patent: March 26, 1996Assignee: The Upjohn CompanyInventors: Donald E. Ayer, Gordon L. Bundy, Eric J. Jacobsen
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Patent number: 5489603Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.Type: GrantFiled: July 15, 1993Date of Patent: February 6, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
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Patent number: 5482960Abstract: Novel indole and indoline nonpeptide antagonists of endothelin I are described, as well as novel intermediates used in their preparation, methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, essential renovascular malignant and pulmonary hypertension, cerebral infarction, cerebral ischemia, congestive heart failure and subarachnoid hemorrhage.Type: GrantFiled: November 14, 1994Date of Patent: January 9, 1996Assignee: Warner-Lambert CompanyInventors: Kent A. Berryman, Amy M. Bunker, Annette M. Doherty, Jeremy J. Edmunds
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Patent number: 5482962Abstract: This invention relates to N,N'-disubstituted-N,N'-diacylhydrazines which are useful as insecticides, compositions containing those compounds and methods of their use. This invention also relates to the production of intermediates useful in the production of such compounds.The compounds of this invention may be represented by the formula ##STR1## wherein R.sup.1 is cyano or H,R.sup.2 is branched alkyl,B is aryl or substituted aryl,R.sup.a is H or a variety of substituents, andZ forms a fused 5-member heterocyclic ring.Type: GrantFiled: July 22, 1994Date of Patent: January 9, 1996Assignee: Rohm and Haas CompanyInventor: Robert E. Hormann
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Patent number: 5464872Abstract: A compound which is selected from those of formula (I): ##STR1## in which A, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are as defined in the description, its optical isomers, and its addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful for treating a disorder of the melatoninergic system.Type: GrantFiled: January 18, 1995Date of Patent: November 7, 1995Assignee: Adir et CompagnieInventors: Michel Langlois, Pierre Renard, Gerard Adam
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Patent number: 5446162Abstract: A process for the production of 7-acylindoles of the general formula: ##STR1## starting from indoline of the formula: ##STR2## Indoline is cyanized in a first stage to 7-cyanoindoline of the formula: ##STR3## The latter is catalytically dehydrogenated in a second stage to 7-cyanindole of the formula: ##STR4## The latter is then acylated in a third stage with an organometallic compound of the formula:R--Q Vinto the end product according to formula I.Type: GrantFiled: July 26, 1994Date of Patent: August 29, 1995Assignee: Lonaz Ltd.Inventors: Jean-Paul Roduit, Alain Wellig
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Patent number: 5439929Abstract: The present invention relates to bicyclic carbamate compounds and, specifically, to compounds of the formula ##STR1## wherein X, Y, R.sup.1 and R.sup.2 are as defined in the specification. The compounds of this invention are useful in the treatment of asthma, rheumatoid arthritis, osteoarthritis, bronchitis, chronic obstructive airways disease, psoriasis, allergic rhinitis, atopic dermatitis, shock, other inflammatory diseases, and other conditions where the treatment is effected or facilitated by blocking the leukotriene D4 receptor.Type: GrantFiled: March 1, 1994Date of Patent: August 8, 1995Assignee: Pfizer Inc.Inventor: Matthew F. Brown
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Patent number: 5428052Abstract: Aromatic heterocyclic derivatives have the formula ##STR1## wherein R.sub.1 represents (i)--CH.sub.3, (ii)--CH.sub.2 OH or (iii) ##STR2## wherein R.sub.3 represents hydrogen, --OR.sub.4 wherein R.sub.4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R.sub.3 represents ##STR3## wherein r' and r" represent hydrogen, lower alkyl or together form a heterocycle, R.sub.2 represents hydrogen or --CH.sub.3 and Ar represents ##STR4## wherein R.sub.6 is hydrogen or alkyl having 1-10 carbon atoms and R.sub.7 represents alkyl having 4-12 carbon atoms or cycoalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R.sub.8 when R.sub.8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R.sub.6 is alkyl having 1-4 carbon atoms and R.sub.7 is branched alkyl having 4-12 atoms.Type: GrantFiled: December 2, 1993Date of Patent: June 27, 1995Assignee: Centre Internationale de Recherches Dermatologiques (C.I.R.D.)Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
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Patent number: 5399713Abstract: Process for the production of 5,6-dihydroxyindolines by ether cleavage of corresponding ether procursors with aqueous hydrogen bromide and subsequent direct crystallization from the aqueous reaction mixture.Type: GrantFiled: March 18, 1994Date of Patent: March 21, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Georg Knuebel, Guenther Konard, Roswitha Michel
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Patent number: 5399574Type: GrantFiled: March 3, 1992Date of Patent: March 21, 1995Assignee: Burroughs Wellcome Co.Inventors: Alan D. Robertson, Alan P. Hill, Robert C. Glen, Graeme R. Martin
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Patent number: 5397801Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: May 10, 1994Date of Patent: March 14, 1995Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5391758Abstract: The invention concerns novel, pharmaceutically useful, amide derivatives of certain benzoheterocyclylalkanoic acids (and related tetrazoles and acylsulphonamides) of the formula I and salts thereof, wherein the radicals R.sup.1, R.sup.2, L, X, Y, Z, A.sup.1, Q, A.sup.2 and M have the meanings set out in the specification. The invention also includes pharmaceutical compositions incorporating a formula I compound or a salt thereof, a process for the manufacture of the said compound, together with intermediates for use in the latter process.Type: GrantFiled: June 6, 1994Date of Patent: February 21, 1995Assignee: Zeneca, Inc.Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying K. Yee
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Patent number: 5384402Abstract: Methine transfer dyes have the formula ##STR1## where L is a bridge member which does not permit any conjugation of .pi.-electrons between Z and Y,X is cyano, C.sub.1 -C.sub.6 -alkoxycarbonyl or C.sub.1 -C.sub.6 -monoalkylcarbamoyl, wherein alkyl may in each case be interrupted by oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkoxycarbonyl, C.sub.5 -C.sub.7 -monocycloalkylcarbamoyl, phenoxycarbonyl or monophenylcarbamoyl, andY and Z are each independently of the other aminophenylene, which may be benzo-fused, or heterocyclyl.Type: GrantFiled: June 7, 1994Date of Patent: January 24, 1995Assignee: BASF AktiengesellschaftInventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens
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Patent number: 5380857Abstract: A process for the production of 7-acylindoles of the general formula: ##STR1## starting from indoline of the formula: ##STR2## Indoline is cyanized in a first stage to 7-cyanoindoline of the formula: ##STR3## The latter is catalytically dehydrogenated in a second stage to 7-cyanindole of the formula: ##STR4## The latter is then acylated in a third stage with an organometallic compound of the formula:R--Q Vinto the end product according to formula I.Type: GrantFiled: June 30, 1993Date of Patent: January 10, 1995Assignee: Lonza Ltd.Inventors: Jean-Paul Roduit, Alain Wellig
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Patent number: 5359083Abstract: The invention relates to a novel process for the preparation of compounds of formula I ##STR1## wherein R is straight-chain C.sub.2 -C.sub.4 alk-1-en-1-yl, and salts thereof, and to a novel starting material and the use thereof.Type: GrantFiled: February 10, 1994Date of Patent: October 25, 1994Assignee: Ciba-Geigy CorporationInventors: Marc Gerspacher, Alfred Sallmann
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Patent number: 5330986Abstract: This invention relates to indole-7-carboxamide derivatives of the formula ##STR1## where R.sub.1 through R.sub.6 are independently H, loweralkyl, aryl, and aralkyl; and in addition R.sub.3 and R.sub.5 can be joined together to form a piperazine ring of the formula ##STR2## where R.sub.7 is H, loweralkyl, aryl, arylloweralkyl, pyrimidyl; and R.sub.4 and R.sub.5 can be joined together to form a pyrrolidine ring of the formula ##STR3## where R.sub.8 is H, loweralkyl, aryl, arylloweralkyl; X is H, loweralkyl, halogen, NO.sub.2, CF.sub.3, NH.sub.2, and OR.sub.9 ; where R.sub.9 is loweralkyl, arylloweralkyl and n is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and the optical isomers thereof where such isomers exist.Type: GrantFiled: November 24, 1992Date of Patent: July 19, 1994Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventor: Gregory M. Shutske
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Patent number: 5330981Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.Type: GrantFiled: December 30, 1992Date of Patent: July 19, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5322951Abstract: An intermediate compound of Formula (V): ##STR1## wherein G is COQ.sub.1 and Q.sub.1 represents chloro, bromo, C.sub.1-4 alkoxy, PhO--, Cl.sub.5 C.sub.6 O--, Cl.sub.3 CO--, succinimidyloxy or imidazolyloxy; the remainder of the terms R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and Y are defined in the specification. The intermediates of Formula V are useful for preparing 1-(2,3-dihydro-1-carboxamide final products wherein said final products possess 5-HT M-receptor antagonist activity.Type: GrantFiled: November 13, 1992Date of Patent: June 21, 1994Assignee: Beecham Group, p.l.c.Inventors: Francis D. King, Karen A. Joiner
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Patent number: 5296452Abstract: 3-(N-3,4,5,6-Tetrahydrophthalimido)-cinnamic esters of the general formula I ##STR1## where n is 1 or 2 and the substituents have the following meanings:R.sup.1 is hydrogen or fluorine,R.sup.2 is halogen,R.sup.3 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl,R.sup.4 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or benzyl,R is C.sub.1 -C.sub.4 -alkyl,processes for their manufacture, and herbicidal agents containing them.Type: GrantFiled: May 18, 1990Date of Patent: March 22, 1994Assignee: BASF AktiengesellschaftInventors: Lothar Rueb, Karl Eicken, Karl-Otto Westphalen, Bruno Wuerzer
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Patent number: 5288877Abstract: Described is a continuous process for preparing indolenine compounds which comprises charging continuously and simultaneously to a reactor containing an acetic acid reaction medium (1) substituted phenylhydrazine and (2) unsymmetrical ketone from separate sources, continuously discharging from the reactor indolenine product in acetic acid solution, separating acetic acid from the indolenine product, recycling separated acetic acid to the reactor, neutralizing residual acetic acid remaining in the indolenine product with aqueous inorganic alkaline reagent, and separating from the indolenine product an aqueous solution of salts resulting from the preparation and neutralization of the indolenine product.Type: GrantFiled: July 3, 1991Date of Patent: February 22, 1994Assignee: PPG Industries, Inc.Inventors: Charles H. Hoelscher, Bruce R. Anderson
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Patent number: 5258399Abstract: The invention concerns sulphonamide derivatives of the formula I ##STR1## wherein R.sup.1 includes (1-4C)alkyl; R.sup.2 and R.sup.3 together form --A.sup.2 --X.sup.2 --A.sup.3 --which defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is optionally substituted phenylene or Ar is pyridylene;Q is nitrogen or of the formula CR.sup.7, wherein R.sup.7 includes hydrogen, halogeno, (1-4C)alkyl and (1-4C)alkoxy;each of R.sup.4 and R.sup.5 is (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl or optionally substituted phenyl, benzyl or pyridyl, or R.sup.5 may be hydrogen; andR.sup.6 has any of the meanings defined for R.sup.7 ;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: December 22, 1992Date of Patent: November 2, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventor: David Waterson
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Patent number: 5256794Abstract: Squarylium compounds having the following formula (I), ##STR1## and an optical information recording medium comprising a substrate and a recording layer formed on the substrate, comprising a squarylium compound having formula (I) are disclosed.Type: GrantFiled: July 9, 1990Date of Patent: October 26, 1993Assignees: Ricoh Company, Ltd., Kyowa Hakko Kogyo Co. Ltd.Inventors: Tsutomu Satoh, Ikuo Shimizu, Yukiyoshi Ito
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Patent number: 5223510Abstract: The subject of the invention is benzofuran, benzothiophene, indole or indolizine compounds of general formula: ##STR1## in which: Het represents one of the groups: ##STR2## in which T,T' and T"represent particularly a group: ##STR3## R and R.sub.a, identical or different, represent X represent --O-- or --S--Y represents a radical ##STR4## These compounds are useful as medecines particularly for the treatment of pathological syndroms of the cardio-vascular system.Type: GrantFiled: July 26, 1991Date of Patent: June 29, 1993Assignee: SanofiInventors: Jean Gubin, Pierre Chatelain, Jean Lucchetti, Gilbert Rosseels, Henri Inion
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Patent number: 5218116Abstract: Procedure for the preparation of nitroxyl radicals of sterically hindered amines, consisting of the reaction of amines with hydrogen peroxide in the presence of a titanium containing catalyst, particularly in the presence of titanium silicalites.The catalyst can be recovered at the end of the reaction and recycled.Type: GrantFiled: November 29, 1991Date of Patent: June 8, 1993Assignee: Enichem Synthesis S.p.A.Inventors: Carlo Neri, Silvestro Costanzi, Rosa M. Riva, Mariangela Angaroni
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Patent number: 5204467Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed.Type: GrantFiled: December 20, 1991Date of Patent: April 20, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5106865Abstract: Indole diterpene compounds named "radarin" have been isolated from the sclerotia of the fungus Aspergillus sulphureus. The radarins are effective for controlling Lepidopteran insects, and have the structures: ##STR1## wherein the compound formed when R is a hydroxyl group is designated radarin A and the compound formed when R is a hydrogen atom is designated radarin C; and ##STR2## wherein the compound formed when R is a hydrogen atom is designated radarin D and the compound formed when R is a hydroxyl group is designated radarin B.Type: GrantFiled: July 19, 1991Date of Patent: April 21, 1992Assignees: The United States of America as represented by the Secretary of Agriculture, Biotechnology Research & Development Corporation, University of Iowa Research FoundationInventors: Jodi A. Laakso, Patrick F. Dowd, James B. Gloer, Donald T. Wicklow
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Patent number: 5103007Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.Type: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5081245Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.Type: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5055589Abstract: The present invention provides an indolenine derivative represented by the formula ##STR1## wherein R.sup.1 is a hydrogen atom or a lower alkyl group, X and Y are the same or different and each represent a methylene group or an oxygen atom. This indolenine derivative is useful as an intermediate for synthesizing a cyanine compound suitable for use as an organic near infrared light-absorbing dye useful as an optical disc recording medium adapted for semiconductor laser recording.Type: GrantFiled: May 14, 1990Date of Patent: October 8, 1991Assignee: Asahi Chemical Co., Ltd.Inventors: Osamu Manabe, Shigeo Fujita, Shizuo Iwata, Morihiro Kamiyama
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Patent number: 4994615Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature of -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 6.10.sup.6 Pa with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY.sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or one diene ligand, Y is a chiral diphosphine, the secondary phosphine groups of which are linked by 2-4 C atoms and which, together with the Ir atom, forms a 5-, or 6- or 7-ring, or Y is a chiral diphosphinite, the phosphinite groups of which are linked via 2 C atoms and which together with the Ir atom forms a 7-ring, Z is Cl, Br or I and A.sup.63 is the anion of an oxygen acid or complex acid, and if appropriate with the addition of an ammonium or alkali metal chloride, bromide or iodide.Type: GrantFiled: July 29, 1987Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Felix Spindler, Benoit Pugin
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Patent number: 4954640Abstract: Process for the industrial synthesis of (2S,3 7aS)-2-carboxyperhydroindole by reduction of 2-carboxindole or of one of its esters to (R,S)-2-carboxyindo or of one of its esters which, after saponification, converted into the acid, the S isomer cf (R,S)-2-carboxyindoline being obtained by precipitation from the mixture of the two (R) and (S) isomers, in the presence of (+) methylbenzylamine, (S)-2-carboxyindoline being in its turn subjected to catalytic hydrogenation to give (2S, 3aS,7aS)-2-carboxyperhydroindole, after separation of (2S,3aR,7aR) isomer by crystallization.Application to the synthesis of carboxyalkyl d peptides capable of being employed in therapeutics.Type: GrantFiled: January 10, 1990Date of Patent: September 4, 1990Assignee: ADIR et CieInventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
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Patent number: 4923641Abstract: Highly concentrated stable solutions of color-forming agents of the general formula ##STR1## wherein x denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkylamino, dialkylamino, acylamino, aralkylamino or arylamino andR denotes alkyl, alkenyl or aralkyl,further isocyclic or heterocyclic rings can be fused onto the rings A, B, C and D and the cyclic and acyclic radicals and the rings A, B, C and D can carry further non-ionic substituents which are customary in dyestuff chemistry, or mixtures thereof, in water-insoluble organic solvents from the group comprising optionally chlorinated hydrocarbons, vegetable oils and phthalic acid esters are used for the preparation of pressure-sensitive recording materials.Type: GrantFiled: September 20, 1988Date of Patent: May 8, 1990Assignee: Bayer AktiengesellschaftInventors: Udo Eckstein, Hubertus Psaar
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Patent number: 4897223Abstract: Color-forming agents of the general formula ##STR1## wherein X denotes hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkoxycarbonyloxy, alkylamino, dialkylamino, acylamino, aralkylamino or arylamino,Q denotes cyano, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, N-alkyl-N-aryl-carbamoyl, acyl, alkoxysulphonyl, aralkoxysulphonyl, sulphamoyl, N-alkylsulphamoyl, N,N-dialkylsulphamoyl, alkylsulphonyl, arylsulphonyl or aralkylsulphonyl andR denotes alkyl, alkenyl or aralkyl,further isocyclic or heterocyclic rings can be fused on to the rings A, B, C and D, and the cyclic and acyclic radicals and the rings A, B, C and D can carry further substituents, are used for the preparation of pressure-sensitive recording materials.Type: GrantFiled: March 1, 1988Date of Patent: January 30, 1990Assignee: Bayer AktiengesellschaftInventors: Udo Eckstein, Hubertus Psaar, Roderich Raue
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Patent number: 4886887Abstract: Indolines of the formula ##STR1## wherein R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl and each of R.sub.2 and R.sub.3 independently of the other is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, are prepared by cyclodehydrating a 2-(2'-aminophenyl)ethanol of formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, at 150.degree.-350.degree. C. in the presence of an amorphous aluminum silicate.The indolines of the above formula are useful intermediates for the synthesis of plant protective agents.Type: GrantFiled: October 9, 1986Date of Patent: December 12, 1989Assignee: Ciba-Geigy CorporationInventors: Beat M. Aebli, Claude Gremmelmaier
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Patent number: 4859692Abstract: The invention concerns novel, pharmaceutically useful, amide derivatives of certain benzoheterocyclylalkanoic acids (and related tetrazoles and acylsulphonamides) of the formula I and salts thereof, wherein the radicals R.sup.1, R.sup.2, L, X, Y, Z, A.sup.1, Q, A.sup.2 and M have the meanings set out in the specification. The invention also includes pharmaceutical compositions incorporating a formula I compound or a salt thereof, a process for the manufacture of the said compound, together with intermediates for use in the latter process.Type: GrantFiled: April 16, 1986Date of Patent: August 22, 1989Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying Kwong Yee
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Patent number: 4843081Abstract: A and A' are each hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy or aryloxy;X is cyano, nitro, COOR, SR, SOR or SOOR;R is H, C.sub.1-6 alkyl or aryl;n n' and n" are each 0 to 4; andm, m' and m" are each 1 to 4, have calcium channel blocking activity.Type: GrantFiled: June 27, 1988Date of Patent: June 27, 1989Assignee: Rorer Pharmaceutical CorporationInventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles