The Five-membered Hetero Ring Contains One Double Bond Only (i.e., Indolines) Patents (Class 548/490)
  • Patent number: 5717108
    Abstract: 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: Grant
    Filed: December 5, 1996
    Date of Patent: February 10, 1998
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Michel Philippe, Remy Tuloup
  • Patent number: 5708178
    Abstract: 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: Grant
    Filed: September 20, 1996
    Date of Patent: January 13, 1998
    Assignee: Lockheed Martin Corporation
    Inventors: Susan P. Ermer, Doris S. Y. Leung, Steven M. Lovejoy
  • Patent number: 5688966
    Abstract: 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: Grant
    Filed: July 26, 1996
    Date of Patent: November 18, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mark Norman Bobrow, Thomas Joseph Erickson
  • Patent number: 5686616
    Abstract: 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: Grant
    Filed: March 14, 1996
    Date of Patent: November 11, 1997
    Assignee: Takasago International Corporation
    Inventors: Kazuhide Tani, Tsuneaki Yamagata, Yasutaka Kataoka, Hidenori Kumobayashi
  • Patent number: 5668271
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: September 16, 1997
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Katsuhisa Kojiri, Hisao Kondo, Hiroharu Arakawa, Mitsuru Ohkubo, Hiroyuki Suda
  • Patent number: 5663183
    Abstract: 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: Grant
    Filed: May 24, 1996
    Date of Patent: September 2, 1997
    Assignee: Synthelabo
    Inventors: Jonathan Frost, Pascal George, Patrick Pasau, Regine Bartsch, Corinne Rousselle, Paul Howard Williams, Jean Claude Muller
  • Patent number: 5658904
    Abstract: 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: Grant
    Filed: June 6, 1995
    Date of Patent: August 19, 1997
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5646298
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: ProCoron, Inc.
    Inventor: Michael J. Powell
  • Patent number: 5631381
    Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: May 20, 1997
    Assignee: Rhone-Poulenc Inc.
    Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
  • Patent number: 5599774
    Abstract: 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: Grant
    Filed: December 31, 1992
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ferenc M. Pallos, Christopher J. Mathews
  • Patent number: 5583234
    Abstract: 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: Grant
    Filed: December 29, 1993
    Date of Patent: December 10, 1996
    Assignee: L'Oreal
    Inventors: Alain Lagrange, Herv e Andrean, Alex Junino
  • Patent number: 5578633
    Abstract: 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: Grant
    Filed: June 2, 1995
    Date of Patent: November 26, 1996
    Assignee: Sanofi
    Inventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
  • Patent number: 5571727
    Abstract: 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: Grant
    Filed: October 7, 1994
    Date of Patent: November 5, 1996
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Nobuyuki Shigetoh, Hiroshi Nakayama, Jinsei Miyazaki, Tadayasu Mitsumata
  • Patent number: 5554642
    Abstract: 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: Grant
    Filed: May 22, 1995
    Date of Patent: September 10, 1996
    Assignee: Adir et Compagnie
    Inventors: Michel Langlois, Pierre Renard, G erard Adam
  • Patent number: 5502187
    Abstract: 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: Grant
    Filed: October 3, 1994
    Date of Patent: March 26, 1996
    Assignee: The Upjohn Company
    Inventors: Donald E. Ayer, Gordon L. Bundy, Eric J. Jacobsen
  • Patent number: 5489603
    Abstract: 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: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5482960
    Abstract: 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: Grant
    Filed: November 14, 1994
    Date of Patent: January 9, 1996
    Assignee: Warner-Lambert Company
    Inventors: Kent A. Berryman, Amy M. Bunker, Annette M. Doherty, Jeremy J. Edmunds
  • Patent number: 5482962
    Abstract: 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: Grant
    Filed: July 22, 1994
    Date of Patent: January 9, 1996
    Assignee: Rohm and Haas Company
    Inventor: Robert E. Hormann
  • Patent number: 5464872
    Abstract: 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: Grant
    Filed: January 18, 1995
    Date of Patent: November 7, 1995
    Assignee: Adir et Compagnie
    Inventors: Michel Langlois, Pierre Renard, Gerard Adam
  • Patent number: 5446162
    Abstract: 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: Grant
    Filed: July 26, 1994
    Date of Patent: August 29, 1995
    Assignee: Lonaz Ltd.
    Inventors: Jean-Paul Roduit, Alain Wellig
  • Patent number: 5439929
    Abstract: 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: Grant
    Filed: March 1, 1994
    Date of Patent: August 8, 1995
    Assignee: Pfizer Inc.
    Inventor: Matthew F. Brown
  • Patent number: 5428052
    Abstract: 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: Grant
    Filed: December 2, 1993
    Date of Patent: June 27, 1995
    Assignee: Centre Internationale de Recherches Dermatologiques (C.I.R.D.)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5399713
    Abstract: 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: Grant
    Filed: March 18, 1994
    Date of Patent: March 21, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Georg Knuebel, Guenther Konard, Roswitha Michel
  • Patent number: 5399574
    Type: Grant
    Filed: March 3, 1992
    Date of Patent: March 21, 1995
    Assignee: Burroughs Wellcome Co.
    Inventors: Alan D. Robertson, Alan P. Hill, Robert C. Glen, Graeme R. Martin
  • Patent number: 5397801
    Abstract: 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: Grant
    Filed: May 10, 1994
    Date of Patent: March 14, 1995
    Assignee: Sanofi
    Inventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
  • Patent number: 5391758
    Abstract: 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: Grant
    Filed: June 6, 1994
    Date of Patent: February 21, 1995
    Assignee: Zeneca, Inc.
    Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying K. Yee
  • Patent number: 5384402
    Abstract: 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: Grant
    Filed: June 7, 1994
    Date of Patent: January 24, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens
  • Patent number: 5380857
    Abstract: 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: Grant
    Filed: June 30, 1993
    Date of Patent: January 10, 1995
    Assignee: Lonza Ltd.
    Inventors: Jean-Paul Roduit, Alain Wellig
  • Patent number: 5359083
    Abstract: 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: Grant
    Filed: February 10, 1994
    Date of Patent: October 25, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Marc Gerspacher, Alfred Sallmann
  • Patent number: 5330986
    Abstract: 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: Grant
    Filed: November 24, 1992
    Date of Patent: July 19, 1994
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventor: Gregory M. Shutske
  • Patent number: 5330981
    Abstract: 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: Grant
    Filed: December 30, 1992
    Date of Patent: July 19, 1994
    Assignee: Istituto Gentili S.p.A.
    Inventors: Sergio Rosini, Maurizio Mian
  • Patent number: 5322951
    Abstract: 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: Grant
    Filed: November 13, 1992
    Date of Patent: June 21, 1994
    Assignee: Beecham Group, p.l.c.
    Inventors: Francis D. King, Karen A. Joiner
  • Patent number: 5296452
    Abstract: 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: Grant
    Filed: May 18, 1990
    Date of Patent: March 22, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Rueb, Karl Eicken, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5288877
    Abstract: 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: Grant
    Filed: July 3, 1991
    Date of Patent: February 22, 1994
    Assignee: PPG Industries, Inc.
    Inventors: Charles H. Hoelscher, Bruce R. Anderson
  • Patent number: 5258399
    Abstract: 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: Grant
    Filed: December 22, 1992
    Date of Patent: November 2, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventor: David Waterson
  • Patent number: 5256794
    Abstract: 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: Grant
    Filed: July 9, 1990
    Date of Patent: October 26, 1993
    Assignees: Ricoh Company, Ltd., Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Tsutomu Satoh, Ikuo Shimizu, Yukiyoshi Ito
  • Patent number: 5223510
    Abstract: 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: Grant
    Filed: July 26, 1991
    Date of Patent: June 29, 1993
    Assignee: Sanofi
    Inventors: Jean Gubin, Pierre Chatelain, Jean Lucchetti, Gilbert Rosseels, Henri Inion
  • Patent number: 5218116
    Abstract: 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: Grant
    Filed: November 29, 1991
    Date of Patent: June 8, 1993
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Carlo Neri, Silvestro Costanzi, Rosa M. Riva, Mariangela Angaroni
  • Patent number: 5204467
    Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 20, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5106865
    Abstract: 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: Grant
    Filed: July 19, 1991
    Date of Patent: April 21, 1992
    Assignees: The United States of America as represented by the Secretary of Agriculture, Biotechnology Research & Development Corporation, University of Iowa Research Foundation
    Inventors: Jodi A. Laakso, Patrick F. Dowd, James B. Gloer, Donald T. Wicklow
  • Patent number: 5103007
    Abstract: 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: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5081245
    Abstract: 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: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5055589
    Abstract: 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: Grant
    Filed: May 14, 1990
    Date of Patent: October 8, 1991
    Assignee: Asahi Chemical Co., Ltd.
    Inventors: Osamu Manabe, Shigeo Fujita, Shizuo Iwata, Morihiro Kamiyama
  • Patent number: 4994615
    Abstract: 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: Grant
    Filed: July 29, 1987
    Date of Patent: February 19, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Felix Spindler, Benoit Pugin
  • Patent number: 4954640
    Abstract: 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: Grant
    Filed: January 10, 1990
    Date of Patent: September 4, 1990
    Assignee: ADIR et Cie
    Inventors: Michel Vincent, Jean Baliarda, Bernard Marchand, Georges Remond
  • Patent number: 4923641
    Abstract: 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: Grant
    Filed: September 20, 1988
    Date of Patent: May 8, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Eckstein, Hubertus Psaar
  • Patent number: 4897223
    Abstract: 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: Grant
    Filed: March 1, 1988
    Date of Patent: January 30, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Eckstein, Hubertus Psaar, Roderich Raue
  • Patent number: 4886887
    Abstract: 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: Grant
    Filed: October 9, 1986
    Date of Patent: December 12, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Beat M. Aebli, Claude Gremmelmaier
  • Patent number: 4859692
    Abstract: 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: Grant
    Filed: April 16, 1986
    Date of Patent: August 22, 1989
    Assignee: ICI Americas Inc.
    Inventors: Peter R. Bernstein, Frederick J. Brown, Victor G. Matassa, Ying Kwong Yee
  • Patent number: 4843081
    Abstract: 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: Grant
    Filed: June 27, 1988
    Date of Patent: June 27, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: John R. Regan, Jeffrey N. Barton, John T. Suh, Jerry W. Skiles