The Chalcogen Is Bonded Directly To A Ring Carbon Of The Five-membered Hetero Ring Which Is Adjacent To The Ring Nitrogen (e.g., 2-indolinones, Etc.) Patents (Class 548/486)
  • Patent number: 4581457
    Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## W is ##STR3## Y is ##STR4## n is 0-8; R.sup.1 is hydrogen, loweralkyl, loweralkoxy, lower alkanoyl, halo, trifluoromethyl, cyano or nitro;R.sup.2 is hydrogen or loweralkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and in antithrombotic therapy.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: April 8, 1986
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Dennis M. Kubrak
  • Patent number: 4569942
    Abstract: Certain 2-oxindole-1-carboxamide compounds having an acyl substituent at the 3-position, and also further substituted on the carboxamide nitrogen by an alkyl, cycloalkyl, phenyl or substituted phenyl group, are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and antiinflammatory agents in mammalian subjects. These 2-oxindole-1-carboxamide compounds are of particular value for ameliorating pain in human patients recovering from surgery or trauma, and alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.Certain 2-oxindole-1-carboxamide compounds unsubstituted at C-3, but having a substituent on the carboxamide nitrogen, are useful as intermediates to the analgesic and antiinflammatory agents of the invention.
    Type: Grant
    Filed: March 22, 1985
    Date of Patent: February 11, 1986
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4545806
    Abstract: Cyclohexane-1,3-dione derivatives of the formula ##STR1## where A is an unsubstituted or substituted, saturated or unsaturated 4-membered to 7-membered heterocyclic structure which contains from 1 to 3 nitrogen atoms and may be fused to an aromatic radical, R.sup.1 is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, R.sup.2 is alkyl and R.sup.3 is alkyl, haloalkenyl or propargyl, and salts of these compounds, are useful for controlling undesirable plant growth.
    Type: Grant
    Filed: March 15, 1984
    Date of Patent: October 8, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Rainer Becker, Michael Keil, Wolfgang Spiegler, Bruno Wuerzer
  • Patent number: 4542148
    Abstract: Oxindole derivatives of the general formula I ##STR1## are described, and also processes for their preparation and drugs containing them. The new compounds exhibit a neuroanabolic action in various animal models.
    Type: Grant
    Filed: April 7, 1982
    Date of Patent: September 17, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Kuch, Hansjorg Kruse
  • Patent number: 4539329
    Abstract: The invention concerns novel trifluoromethyl derivatives of 1'-halogenobenzyl-spiro[imidazolidine-4,3'-indoline]-2,2',5-trione (I), their pharmaceutically acceptable salts, and non-toxic, biodegradable precursors thereof. The derivatives are potent inhibitors of the enzyme aldose reductase and are useful in treating or preventing certain complications of diabetes. The invention also provides pharmaceutical compositions and processes for the manufacture of the derivatives.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: September 3, 1985
    Assignee: Imperial Chemical Industries, plc
    Inventors: David R. Brittain, David Brown, Robin Wood
  • Patent number: 4535092
    Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are substituents defined in claim 1; wherein R.sup.4 is hydrogen or alkyl of up to 4 carbon atoms, or is joined to R.sup.5 as stated below;wherein R.sup.5 is hydrogen, hydroxy, or alkoxy or acyloxy each of up to 15 carbon atoms, or is joined to R.sup.4 to form an oxycarbonyl group such that together with the --N--CO--C-- part of the molecule it forms an oxazolidinedione group;wherein R.sup.6 is alkyl or halogenoalkyl of up to 4 carbon atoms;and wherein R.sup.7 is 5- or 6- membered saturated or unsaturated heterocyclic which contains one, two or three hetero atoms selected from oxygen, nitrogen and sulphur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two substituents defined in claim 1;processes for their manufacture and pharmaceutical compositions containing them. The compounds possess antiandrogenic activity.
    Type: Grant
    Filed: November 1, 1982
    Date of Patent: August 13, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Leslie R. Hughes
  • Patent number: 4530843
    Abstract: Heterocyclic amidoxime derivatives of the general formula: ##STR1## wherein R' represents hydrogen or the methyl radical, and R represents the 1-oxo-1H-isoquinolin-2-yl, 2-oxo-2H-quinolin-1-yl, 2,3-dihydro-1H-indol-1-yl, 1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl, 1H-indol-1-yl, 1-oxo-1,3-dihydro-2H-isoindol-2-yl, 2-oxo-3,4-dihydro-2H-quinolin-1-yl, 5-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl, 5-chloro-2-oxo-3-phenyl-2,3-dihydro-1H-benzimidazol-1-yl, 4-chloro-1-oxo-1H-isoquinolin-2-yl or 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl radical, and--when R' represents the methyl radical--racemates and enantiomers of such compounds, are new compounds useful in therapy, and especially for the treatment of complaints of the central nervous system and for the treatment of depression.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: July 23, 1985
    Assignee: Synthelabo
    Inventor: Daniel Obitz
  • Patent number: 4476132
    Abstract: Quinolinone derivatives of the formula (I) ##STR1## in which X represents oxy or a direct bond, R.sub.1 represents an aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic or heterocyclic-aliphatic radical or hydrogen, Ph represents an optionally additionally substituted 1,2-phenylene radical containing the group R.sub.1 --X--C(O)--, and one of the radicals R.sub.2 and R.sub.3 represents an optionally esterified or amidated carboxy group R.sub.4 and the other represents hydrogen or an aliphatic radical or, in the case of a radical R.sub.3, hydroxy, and in which either R.sub.A and R.sub.B together represent oxo, R.sub.C and R.sub.D together represent an additional bond, or, when R.sub.2 represents a radical R.sub.4, R.sub.C is hydrogen and R.sub.3 and R.sub.D together represent oxo, and R.sub.E represents a radical R.sub.5 which represents hydrogen or an aliphatic, cycloaliphatic, araliphatic heterocyclic-aliphatic radical, or R.sub.A represents an optionally etherified hydroxy group and R.sub.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: October 9, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard Goschke, Pier G. Ferrini, Alfred Sallmann
  • Patent number: 4474785
    Abstract: 2-Aryl-3,4-diazabicyclo[4.n.O]alk-2-en-5-ones of the formula I ##STR1## where m and n are identical or different and each is 1, 2 or 3, and R, R.sup.1 and R.sup.2 are identical or different and each is hydrogen or alkyl of 1 to 6 C atoms, said compounds are useful for treating high blood pressure and thrombo-embolic disorders.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: October 2, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Phillip A. Rossy, Marco Thyes, Albrecht Franke, Horst Koenig, Josef Gries, Hans D. Lehmann, Dieter Lenke
  • Patent number: 4460778
    Abstract: Branched alkyldiorganoaminopyridinium salts have been found useful as phase transfer catalysts for facilitating nucleophilic aromatic substitution. For example, the 2-ethylhexyl salts of dialkylaminopyridine, can be used as stable phase transfer catalysts for making aromatic etherimides by reacting substituted phthalimides and alkali metal phenoxides in the presence of a nonpolar organic solvent.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: July 17, 1984
    Assignee: General Electric Company
    Inventor: Daniel J. Brunelle
  • Patent number: 4452808
    Abstract: A series of new chemical compounds which are 4-aminoalkyl-2(3H)-indolones has been demonstrated to be D.sub.2 -agonists useful for treating hypertension. A representative compound of the series is 4-di-n-propylaminoethyl-2(3H)-indolone.
    Type: Grant
    Filed: December 7, 1982
    Date of Patent: June 5, 1984
    Assignee: Smithkline Beckman Corporation
    Inventor: Gregory Gallagher, Jr.
  • Patent number: 4442111
    Abstract: Compounds of the formula ##STR1## wherein n is 0 or 1;A is methylene, vinylene or ethylene optionally substituted by lower alkyl;B is alkylene;R.sub.1 is an optionally substituted alkyl, phenyl or naphthyl group, or a cycloalkyl or pyridyl group; andR.sub.2 is hydrogen or acyl;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antithrombotics.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: April 10, 1984
    Assignee: Dr. Karl Thomae Gesellschaft mit beschrankter Haftung
    Inventors: Erich Muller, Josef Nickl, Berthold Narr, Josef Roch, Walter Haarmann, Johannes M. Weisenberger
  • Patent number: 4440785
    Abstract: Novel 2-aminobiphenylacetic acids, esters and metal salts of the formula are disclosed: ##STR1## wherein R represents hydrogen, lower alkyl, sodium or potassium; R.sup.1 represents fluoro, chloro, bromo, lower-alkyl or amino; R.sup.2 represents lower-alkyl, lower-alkoxy, fluoro, chloro, bromo, amino or trifluoromethyl; and m and n are 0-2 with the proviso that when R.sup.1 or R.sup.2 are tertiary butyl or a sterically hindering lower alkyl radical, m and/or n are 1. The compounds are prepared by hydrolysis of 4-(5-, 6- and 7-)phenylindolin-2-ones to give the 2-amino-3-(4-, 5- and 6-)biphenylacetic acids. The free acids are converted to the esters and metal salts. The compounds have anti-inflammatory activity and inhibit blood platelet aggregation.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: April 3, 1984
    Assignee: A. H. Robins Company, Inc.
    Inventor: David A. Walsh
  • Patent number: 4438121
    Abstract: Heterocyclic amidoxime derivatives of the general formula: ##STR1## wherein R' represents hydrogen or the methyl radical, and R represents the 1-oxo-1H-isoquinolin-2-yl, 2-oxo-2H-quinolin-1-yl, 2,3-dihydro-1H-indol-1-yl, 1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl, 1H-indol-1-yl, 1-oxo-1,3-dihydro-2H-isoindol-2-yl, 2-oxo-3,4-dihydro-2H-quinolin-1-yl, 5-chloro-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl, 5-chloro-2-oxo-3-phenyl-2,3-dihydro-1H-benzimidazol-1-yl, 4-chloro-1-oxo-1H-isoquinolin-2-yl or 3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl radical, and - when R' represents the methyl radical - racemates and enantiomers of such compounds, are new compounds useful in therapy, and especially for the treatment of complaints of the central nervous system and for the treatment of depression.
    Type: Grant
    Filed: May 25, 1982
    Date of Patent: March 20, 1984
    Assignee: Synthelabo
    Inventor: Daniel Obitz
  • Patent number: 4424231
    Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: January 3, 1984
    Assignee: Fisons Limited
    Inventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
  • Patent number: 4343811
    Abstract: This invention relates to novel indole derivatives of formula ##STR1## and the non-toxic, pharmacologically acceptable salts thereof. These compounds exhibit desirable pharmacological properties, especially lipid-level lowering and anti-atherosclerotic activity. The compounds of the invention may be prepared by, for example, alkylation of a corresponding hydroxy indole.
    Type: Grant
    Filed: February 29, 1980
    Date of Patent: August 10, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Rudolf Hurnaus, Gerhart Griss, Wolfgang Grell, Robert Sauter, Bernhard Eisele, Nikolaus Kaubisch, Eckhard Rupprecht, Joachim Kahling
  • Patent number: 4338316
    Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: July 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Peter R. Marsham
  • Patent number: 4329347
    Abstract: Compounds of the formula ##STR1## wherein W is vinylene, methyl-vinylene, methylene or ethylene;m is 0, 1 or 2;D is straight or branched alkylene of 2 to 6 carbon atoms, straight or branched hydroxy-alkylene of 3 to 6 carbon atoms, or xylylene;R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms;R.sub.2 is cycloalkyl of 3 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 11 carbon atoms, heteroaryl, heteroarlkyl, 1,2,4-triazolyl, triphenylmethyl, 4,5-bis-(p-chlorophenyl)-oxazol-2-yl, N-methyl-cyclohexylamino-carbonylmethyl,-amino-iminomethyl or, when m is 1 or D is hydroxyalkylene or xylylene, also alkyl of 1 to 6 carbon atoms; andR.sub.3 and R.sub.4 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, amino, acetylamino or nitro.The compounds of the invention are useful as cardiotonics and as antithrombotics.
    Type: Grant
    Filed: July 24, 1980
    Date of Patent: May 11, 1982
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Erich Muller, Josef Nickl, Josef Roch, Berthold Narr, Walter Haarmann, Johannes M. Weisenberger