Ether Containing Patents (Class 544/174)
  • Patent number: 5272144
    Abstract: Aryloxy- and heteroaryloxy-alkylene derivatives of amines of formula ##STR1## wherein each of A and B is a group of formula (i) to (iii): ##STR2## wherein Y is --O--, --S-- or --NR-- in which R is hydrogen or C.sub.1 -C.sub.6 alkyl; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is independently:a) hydrogen, halogen, hydroxy, cyano or nitro;b) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by halogen,c) C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkylthio;d) C.sub.1 -C.sub.6 alkyl-sulfonyl;e) a substituted amine group --NR.sub.7 R.sub.8 ;f) a --COR.sub.12 group; org) two adjacent groups of R.sub.3, R.sub.4, R.sub.5 and R.sub.6, taken together, form a C.sub.1 -C.sub.4 alkylenedioxy group;each of R.sub.1 and R.sub.2 independently is hydrogen, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkenyl or C.sub.1 -C.sub.6 alkyl unsubstituted or substituted by phenyl; or R.sub.1 and R.sub.
    Type: Grant
    Filed: June 13, 1991
    Date of Patent: December 21, 1993
    Assignee: Farmitalia Carlo Erba s.r.l.
    Inventors: Piero Melloni, Philippe Dostert, Arturo D. Torre, Alberto Bonsignori
  • Patent number: 5183889
    Abstract: A benzonphthalene compound has the formula ##STR1## wherein R.sub.1 represents ##STR2## or (ii) --CH.sub.2 OH; R.sub.6 represents ##STR3## or OR.sub.7 wherein R.sub.7 represents hydrogen, alkyl having 1-20 carbon atoms, monohydroxyalkyl or polyhydroxyalkyl, r' or r" represent hydrogen, lower alkyl, mono or polyhydroxyalkyl, aryl or a residue of an amino acid or a sugar, or together form a heterocycle; R.sub.2 represents hydrogen, alkyl having 1-15 carbon atoms, alkoxy having 1-4 carbon atoms or a cycloaliphatic radical; R.sub.3 represents hydrogen, hydroxy, alkyl having 1-4 carbon atoms, alkoxy having 1-10 carbon atoms, a cycloaliphatic radical, a thiocycloaliphatic radical or --O--Si(CH.sub.3).sub.2 --R.sub.8 wherein R.sub.8 represents lower alkyl; and R.sub.4 and R.sub.5 represent hydrogen, lower alkyl, hydroxy or lower acyloxy.This compound is useful in the topical and systemic treatment of dermatologic diseases and in the treatment of the degeneration of conjuctive tissues.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: February 2, 1993
    Assignee: Centre International de Recherches Dermatologiques (CIRD)
    Inventors: Braham Shroot, Jacques Eustache, Jean-Michel Bernardon
  • Patent number: 5180735
    Abstract: The present invention relates to a compound of the formula: ##STR1## wherein A is halogen, N(O)mR.sup.1 R.sup.2, N.sup..sym. R.sup.1 R.sup.2 R.sup.3 .multidot.X.sup..crclbar., S(O)nR.sup.1 or S.sup..sym. (O)mR.sup.1 R.sup.2 .multidot.X.sup..crclbar. where R.sup.1, R.sup.2 and R.sup.3 are each optionally substituted hydrocarbon or heterocyclic group, X.sup..crclbar. is a counter anion; m is an integer of 0 or 1; n is an integer of 0 to 2; R.sup.1 and R.sup.2 may form a nitrogen-containing or a sulfur-containing heterocyclic ring, which may further form a condensed ring, with the adjacent nitrogen atom or sulfur atom, and these nitrogen-containing or sulfur-containing heterocyclic rings may have substituents, Z is O or NR.sup.4 where R.sup.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: January 19, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shoji Kishimoto, Shogo Marui, Takeshi Fujita
  • Patent number: 5149714
    Abstract: The present invention provides novel aryloxy indanamines of the formula ##STR1## wherein n, p and q are each independently 0, 1 or 2,Y and X are each independently lower alkyl, lower alkoxy, hydroxy, CF.sub.3, halogeno or when p or q are 2 and each of the Y or each of the X groups are on adjacent aryl carbon atoms, both of the X or both of the Y groups can be taken together to form a methylenedioxy moiety,R.sub.1 and R.sub.2 are each independently hydrogen, lower alkyl, aralkyl, or R.sub.1 and R.sub.2 taken together with the nitrogen to which they are attached are pyrrolidino, morpholino, piperidino, piperazino, or 4-methylpiperazino,or an acid addition salt thereof, which are useful as antidepressants and as inhibitors of synaptic norepinephrine and serotonin uptake.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: September 22, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Jules Freedman
  • Patent number: 5141937
    Abstract: Pharmaceutical products containing a 7-diphenylmethylenebicycloheptane or 7-diphenylmethylenebicycloheptene derivative of the formula I ##STR1## in which A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the stated meanings, or a physiologically tolerated acid addition salt of these compounds, and the use thereof as hypolipidemics are described. In addition, new 7-diphenylmethylenebicycloheptane and -heptene derivatives of the formula Ia ##STR2## in which A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the stated meanings, and the physiologically tolerated acid addition salts thereof, as well as processes for the preparation thereof, are described.
    Type: Grant
    Filed: September 21, 1988
    Date of Patent: August 25, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Siegel, Ernold Granzer
  • Patent number: 5116979
    Abstract: Dihydrocaffeic acid derivatives are here disclosed which are applicable as medicines having excellent absorbency in the case of oral administration and good concentration retention in blood.The disclosed compounds have the function to induce the production and secretion of a nerve growth factor (NGF) in the brain tissue, and therefore they are effective as medicines for the progression inhibition and therapy of regressive disorders of the central nervous system.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 26, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Hajime Iizuka, Osamu Yano, Yukio Miyama
  • Patent number: 5095021
    Abstract: Phenylalkylamines of the formula ##STR1## where n is 5, 6, 7, 8 or 9, m is 1, 2 or 3, R.sup.1 is methyl, halogen, substituted or unsubstituted aryl or substituted or unsubstituted phenoxy, and, when m is 2, two adjacent radicals R.sup.1 together denote the radical ##STR2## X is oxygen, except when R.sup.1 is methyl, or the radical ##STR3## R.sup.4 is isopropyl, tert-butyl or substituted or unsubstituted phenyl and R.sup.5 is H or OH, R.sup.2 and R.sup.3 are each hydrogen and, when X is oxygen, R.sup.2 and R.sup.3 additionally denote methyl or ethyl, and their plant-tolerated salts, and fungicides containing these compounds.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: March 10, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Ernst Buschmann, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5089614
    Abstract: An essentially single stage reaction has been discovered in which a disubstituted ethanolamine, that is, a 2,2'-substituted-2-aminoethanol, may be reacted with a haloform and a carbonyl containing compound selected from the group consisting of monoketones and benzaldehyde, in the presence of an alkali metal hydroxide, and optionally in the presence of a phase transfer catalyst, to produce an alkali metal hydroxyethylaminoacetate ("HEAA") which has N-adjacent C atoms on which there are a total of at least three substituents (hence "polysubstituted"), and one or both pairs of substituents on each N-adjacent C atom may be cyclized. The HEAA may be cyclized by the action of a mineral acid to produce a 2-morpholone hydrochloride which is characterized by having a total of at least three substituents on the N-adjacent C atoms of the ring. The 2-morpholone so produced may be reduced to a polysubstituted aminodiol.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: February 18, 1992
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5082840
    Abstract: A method for increasing the weight gain and/or improving the feed utilization efficiency and/or increasing the lean body mass and/or decreasing birth mortality rate and increasing post-natal survival rate of livestock comprises the administration to livestock of an effective, non-toxic amount of a compound of formula (I), or a veterinarily acceptable acid addition salt thereof: ##STR1## wherein R.sup.1 is phenyl (C.sub.1-6) alkyl or optionally substituted C.sub.1-6 alkyl, andW is optionally substituted phenyl, a heterocyclyl group, or phenoxymethyl optionally substituted on the phenyl group. Certain compounds of formula (I) are novel.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: January 21, 1992
    Assignee: Beecham Group p.l.c.
    Inventors: Jonathan R. Arch, Norman H. Rogers
  • Patent number: 5047432
    Abstract: Compounds of formula I ##STR1## and pharmaceutically acceptable salts thereof; in which R.sub.1 and R.sub.2, which are the same or different, are H or an optionally substituted hydrocarbon group or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring;R.sub.3 is an optionally substituted aromatic hydrocarbon group; andR.sub.4 is a hydrocarbon group containing at least one substituent selected from the group consisting of hydroxy and acylated derivatives thereof, optionally substituted alkoxy groups, optionally substituted cycloalkyloxy groups, optionally substituted alkylenedioxy groups, oxo and groups of formula S(O).sub.p R.sub.5 in which p is 0, 1 or 2 and R.sub.5 is an alkyl group, said hydrocarbon group being optionally substituted by additional substituents,are useful in the treatment of depression.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: September 10, 1991
    Assignee: The Boots Company Plc
    Inventors: John R. Housley, James E. Jeffery, David N. Johnston, Bruce J. Sargent
  • Patent number: 5013757
    Abstract: A novel compound of the formula (I): ##STR1## wherein R.sub.1 is optionally esterified or amidated carboxyl; R.sub.2, R.sub.3 and R.sub.4 are the same or different and are hydrogen or alkyl; A is formyl, hydroxyiminomethyl or carboxyl; and X is hydrogen or halogen, or a salt thereof, which is useful as an aromatase inhibitor or an intermediate of its production. Processes for producing the compound of the formula (I) and an aromatase inhibitor containing as an active component the compound of the formula (I) wherein A is formyl and X is hydrogen or, a salt thereof as well as Penicillium funiculosum capable for producing the compound (I) wherein R.sub.1 is carboxyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen and X is formyl are also disclosed.
    Type: Grant
    Filed: April 13, 1990
    Date of Patent: May 7, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tsuneo Kanamaru, Tsuneaki Hida, Masayuki Muroi
  • Patent number: 5010189
    Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.
    Type: Grant
    Filed: October 24, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Herold, Christof Angst
  • Patent number: 4977148
    Abstract: The invention concerns novel phenoxyacetic acid amide derivatives of the formula I (and pharmaceutically acceptable salts thereof) in which R.sup.1 is hydrogen or fluoro, R.sup.2 is phenyl, cycloalkyl, alkyl or alkenyl as defined herein, and R.sup.3 is hydrogen, methyl or ethyl, or R.sup.2 and R.sup.3 together form polymethylene as defined herein. The invention also includes pharmaceutical compositions containing the amide derivatives, means for the manufacture of the said derivatives and for their use in the treatment of obesity and related conditions and/or in the manufacture of novel medicaments.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: December 11, 1990
    Assignee: Imperial Chemical Industries
    Inventors: Brian R. Holloway, Ralph Howe, Balbir S. Rao, Donald Stribling
  • Patent number: 4968706
    Abstract: Compounds of formula I ##STR1## wherein Ar is an optionally substituted phenyl ring; B is a single bond, a group --(CH.sub.2 OCH.sub.2).sub.n being n=1 or 2, a 2,4-disubstituted-1,3-dioxolane ring or a 2,4-disubstituted-1,3-thioxolane ring, R is a single bond, an optionally substituted methylene or ethylene group and T is 2-, 3- or 4-pyridyl, an optionally salified or esterified carboxy group or a carboxyamide group. Said compounds are useful in treatment of respiratory diseases.
    Type: Grant
    Filed: August 11, 1988
    Date of Patent: November 6, 1990
    Assignee: Boehringer Mannhein Italia, S.p.A.
    Inventors: Silvano Spinelli, Roberto Di Domenico, Ernesto Menta, Bruno Lumachi, Licia Gallico, Sergio Tognella
  • Patent number: 4940573
    Abstract: Cationic surface-active products of the formula: ##STR1## in which R.sub.1 =C.sub.4 -C.sub.20 aliphatic radical, R.sub.2 =C.sub.4 -C.sub.20 alkyl, alkoxymethyl or alkenyloxy radical, p=1-2.5, n=2-20 and G denotes an amine or amine oxide group, and their salts are disclosed for use principally in cosmetics.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: July 10, 1990
    Assignee: L'Oreal
    Inventors: Henri Sebag, Guy Vanlerberghe
  • Patent number: 4935543
    Abstract: A novel compound of the formula (I): ##STR1## wherein R.sub.1 is optionally esterified or amidated carboxyl; R.sub.2, R.sub.3 and R.sub.4 are the same or different and are hydrogen or halogen or alkyl; A is formyl, hydroxyiminomethyl or carboxyl; and A is hydrogen or halogen, or a salt thereof, which is useful as an aromatase inhibitor or an intermediate of its production. Processes for producing the compound of the formula (I) and an aromatase inhibitor containing as an active compound the compound of the formula (I) wherein A is formyl and X is hydrogen or, a salt thereof as well as Penicillium funiculosum capable for producing the compound (I) wherein R.sub.1 is carboxyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen and X is formyl are also disclosed.
    Type: Grant
    Filed: May 18, 1989
    Date of Patent: June 19, 1990
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tsuneo Kanamaru, Tsuneaki Hida, Masayuki Muroi
  • Patent number: 4933449
    Abstract: The invention provides a process for the preparation of 3,3-diaryl acrylic acid amides of the formula ##STR1## in which A, B and Q are as defined in the specification, characterized by condensing a compound of formula ##STR2## with a compound of formulaZCH.sub.2 --CO--Q (III)in which Z represents a hydrogen or halogen atom, and, if an intermediate compound is formed of formula ##STR3## dehydrating the intermediate compound.
    Type: Grant
    Filed: June 1, 1988
    Date of Patent: June 12, 1990
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventor: Jurgen Curtze
  • Patent number: 4910200
    Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## B is ##STR3## R.sup.1 is hydrogen; halogen, cyano or optionally substituted C.sub.1-4 alkyl; andQ is NR.sup.8 R.sup.9 or ##STR4## where R.sup.2 to R.sup.11 are substituents of various types. The compounds are useful as fungicides.
    Type: Grant
    Filed: October 9, 1986
    Date of Patent: March 20, 1990
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Jurgen Curtze, Helmut Pieper, Josef Nickl, Heinz-Manfred Becher, Guido Albert, Christo Drandarevski, Sigmund Lust, Ludwig Schroder
  • Patent number: 4904661
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: February 27, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
  • Patent number: 4900823
    Abstract: Compounds of the formula I, II or III ##STR1## in which Ar and Ar' are an oxygen-containing aromatic radical, R.sup.1 and R.sup.2 are a monovalent hydrocarbon radical which is substituted or unsubstituted, or R.sup.1 and R.sup.2 together form alkylene, oxaalkylene or azaalkylene, R.sup.3 is a direct bond or a divalent hydrocarbon radical, X and X' are a monovalent amino group and Y is a divalent amino or diamino group, are excellent photoinitiators for the photocuring of colored, especially pigmented, compositions containing an olefinically unsaturated, photopolymerizable binder.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: February 13, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Rudolf Kirchmayr, Werner Rutsch
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4839155
    Abstract: Iodotamoxifen derivatives which are compounds of formula (3) ##STR1## wherein X represents 3- or 4- iodo and R.sup.1 and R.sup.2, which may be the same or different, represent C.sub.1-3 alkyl, especially methyl or ethyl, groups or R.sup.1 represents a hydrogen atom and R.sup.2 a C.sub.1-3 alkyl group or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached represent a saturated heterocyclic group, especially a pyrrolidino, piperidino, 4-methylpiperidino or morpholino group, and their pharmaceutically acceptable acid addition salts are potent anti-estrogenic compounds useful for treatment of estrogen receptor-positive (hormone-dependent) breast cancers.Radioisotopic iodotamoxifen derivatives of formula (3) are useful in radiotherapy or gamma ray imaging of these cancers.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: June 13, 1989
    Assignee: National Research Development Corporation
    Inventor: Raymond McCague
  • Patent number: 4837236
    Abstract: A heterocyclic compound of the formula: ##STR1## wherein A is an oxygen atom or a sulfur atom;B is either one of the groups: --CH.sub.2 --CHR.sup.1 -- or --CH.dbd.CR.sup.1 -- (in which R.sup.1 is a hydrogen atom or a methyl group);W is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group;X is either one of the following groups: ##STR2## (in which R.sup.2 is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy(lower)alkyl group, a hydroxyl group or a hydroxy(lower)alkyl group, R.sup.3 is a hydrogen atom or a lower alkyl group and n is an integer of 0 or 1);Z is, the same or different, each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a halo(lower)alkyl group, a halo(lower)alkoxy group, a nitro group, a methylenedioxy group or a cyano group;p is an integer of 0 to 5; andq is an integer of 0 or 1, or its salt, which is useful as a fungicide.
    Type: Grant
    Filed: September 24, 1987
    Date of Patent: June 6, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Meki, Hirotaka Takano
  • Patent number: 4785006
    Abstract: The invention provides fungicidal compositions comprising as an active ingredient a compound having the general formula (I): ##STR1## or a stereoisomer thereof wherein X and Y are hydrogen, alkyl, or alkoxy, provided that when one of X and Y is hydrogen the other is not --C(CH.sub.3).sub.2 R, where R is hydrogen, methyl or ethyl; Z is carbonyl, or a derivative thereof, or is --CR.sup.3 R.sup.4 -- or --CR.sup.3 OR.sup.4 -- in which R.sup.3 and R.sup.4 are hydrogen or C.sub.1-4 alkyl; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen or C.sub.1-4 alkyl, or R.sup.1 and R.sup.2 together with the adjacent N-atom constitute an optionally substituted heterocyclic ring; and n is 0 or 1.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: November 15, 1988
    Inventors: Paul A. Worthington, Brian K. Snell, Paul DeFraine, Vivienne M. Anthony
  • Patent number: 4783458
    Abstract: The invention provides fungicidal compositions comprising as an active ingredient a compound having the general formula (I): ##STR1## or a stereoisomer thereof, wherein one of X and Y is hydrogen and the other is ##STR2## where R is H, methyl or ethyl; Z is carbonyl, or a derivative thereof, or is --CR.sup.3 R.sup.4 -- or --CR.sup.3 OR.sup.4 in which R.sup.3 and R.sup.4 are hydrogen or alkyl groups; R.sup.1 and R.sup.2, which may be the same or different, are alkyl groups containing from 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom constitute an optionally substituted heterocyclic ring; and n is 0 or 1.
    Type: Grant
    Filed: June 10, 1986
    Date of Patent: November 8, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul A. Worthington, Brian K. Snell, Paul De Fraine, Vivienne M. Anthony
  • Patent number: 4783460
    Abstract: Compounds of formula (I): ##STR1## or a salt thereof, in which W is phenyl optionally substituted by halogen or trifluoromethyl, or a benzofuran-2-yl group,R.sup.1 is hydrogen or methyl,R.sup.2 is carboxyl or a group O--Z--CO.sub.2 H or an ester or amide thereof; a group O--E--NR.sup.3 R.sup.4 or a group O--E--OR.sup.5, wherein R.sup.3, R.sup.4 and R.sup.5 each represents hydrogen or C.sub.1-6 alkyl, Z is a C.sub.1-6 straight or branched alkylene chain, n is 1 or 2, a is 2 or 3, and E is a C.sub.2-7 straight or branched alkylene chain with at least two carbon atoms separating the two heteroatoms in the group R.sup.2 ; a process for the production of such compounds and their use in treating hyperglycaemia and/or obesity.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: November 8, 1988
    Assignee: Beecham Group p.l.c.
    Inventor: Barrie C. C. Cantello
  • Patent number: 4758564
    Abstract: Amines of the general formula ##STR1## where A is alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenylalkyl or phenylalkenyl, X is oxygen or sulfur, B is an alkylene chain and R.sup.1 and R.sup.2 are each alkyl, alkenyl or cycloalkyl, or R.sup.1 and R.sup.2 form part of a heterocyclic structrure, and their salts, as well as fungicides containing these compounds.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 19, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Ernst Buschmann, Norbert Goetz, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4753934
    Abstract: Compounds of the formula ##STR1## wherein A, B, R.sub.1, X and Q are substituents of various types, and acid addition salts thereof. The compounds are useful as fungicides.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 28, 1988
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Josef Nickl, Helmut Pieper, Jurgen Curtze, Christo Drandarevski, Sigmund Lust
  • Patent number: 4751303
    Abstract: A novel benzoquinone derivative of the general formula: ##STR1## [wherein R.sub.1 and R.sub.2 are the same or different and each is methyl or methoxy; n is an integer of 0 to 21; m is 0 or 1, Z is a group of the formula: (wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen or an alkyl group which may optionally be substituted or, R.sub.3 and R.sub.4 together with the adjacent nitrogen atom form a morpholino group), a group of the formula: --COR.sub.5 (wherein R.sub.5 is an .alpha.-amino acid residue or a substituted or unsubstituted glucosamine residue), a group of the formula: ##STR2## (wherein R.sub.6 is a divalent hydrocarbon group of 1 to 3 carbon atoms), a group of the formula: ##STR3## (wherein R.sub.6 has the same meaning as defined above) or a group of the formula: --CH.dbd.CH).sub.l COR.sub.7 (wherein l is an integer of 1 to 4 and R.sub.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: June 14, 1988
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Hisayoshi Okazaki, Isuke Imada
  • Patent number: 4739052
    Abstract: Compounds of the formula I, II or III ##STR1## in which Ar and Ar' are an oxygen-containing aromatic radical, R.sup.1 and R.sup.2 are a monovalent hydrocarbon radical which is substituted or unsubstituted, or R.sup.1 and R.sup.2 together form alkylene, oxaalkylene or azaalkylene, R.sup.3 is a direct bond or a divalent hydrocarbon radical, X and X' are a monovalent amino group and Y is a divalent amino or diamino group, are excellent photoinitiators for the photocuring of colored, especially pigmented, compositions containing an olefinically unsaturated, photopolymerizable binder.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: April 19, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Rudolf Kirchmayr, Werner Rutsch
  • Patent number: 4732896
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: March 22, 1988
    Assignee: Delalande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4721786
    Abstract: Fungicidally active novel .beta.-naphthylalkylamines of the formula ##STR1## in which Ar represents optionally substituted .beta.-naphthyl andR.sup.1 and R.sup.2, which can be identical or different, represent alkyl or alkenyl orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, represent an optionally substituted saturated heterocyclic radical, which can contain further hetero-atoms,or plant-tolerated acid addition salts thereof.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: January 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Weissmuller, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4665174
    Abstract: A process for preparing cyclopentenone derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkyl or lower alkenyl, R.sup.2 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted ar(lower)alkyl and A is the residue of a nucleophilic agent from which a hydrogen atom is excluded, which comprises reacting a 3-hydroxy-4-cyclopentenone compound of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above with a nucleophilic agent of the formulaA--H (III)wherein A is as defined above.The cyclopentenone derivatives of the formula (I) are useful as pharmaceuticals, agricultural chemicals, perfumes and as intermediates for the preparation of agricultural chemicals, pharmaceuticals and perfumes.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 12, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayoshi Minai, Tadashi Katsura
  • Patent number: 4661505
    Abstract: This invention provides novel alkane derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.
    Type: Grant
    Filed: November 3, 1982
    Date of Patent: April 28, 1987
    Assignee: Eli Lilly and Company
    Inventors: Winston S. Marshall, John P. Verge
  • Patent number: 4650865
    Abstract: The invention relates to a process for preparing tertiary ether amines corresponding to the following general formula: ##STR1## by reacting in the presence of a strong base a tertiary amine corresponding to the following formula: ##STR2## with a sulfuric acid semi-ester salt corresponding to the following formula:R.sup.1 --(OC.sub.n H.sub.2n).sub.x --OSO.sub.3 M. (III)Preferably, each mole of the tertiary amine corresponding to formula (II) is reacted under substantially anhydrous conditions at a temperature of 140.degree. to 230.degree. C. with from about 0.2 to 3.0 moles of the sulfuric acid semi-ester salt of formula (III) in the presence of from about 1 to 1.5 moles of a strong base preferably an alkali metal hydroxide or an alkali metal alcoholate.
    Type: Grant
    Filed: February 7, 1986
    Date of Patent: March 17, 1987
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Fritz Lange, Alfred Meffert
  • Patent number: 4623382
    Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,R is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloaklyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 -alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.6 aralkyl, wherein the phenyl nucleus is unsubstituted or substituted by halogen; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.
    Type: Grant
    Filed: October 16, 1985
    Date of Patent: November 18, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4618360
    Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties. The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkythio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: October 21, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4613597
    Abstract: Compounds are described of the formulae (1a) and 1b) ##STR1## in which: R.sup.1 is -H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl,W is C.sub.1-7 alkyleneX is cis or trans --CH.dbd.CH--,Y is a saturated heterocyclic amino group having 5-8 ring members,R.sup.2 is (i) substituted or unsubstituted phenylalkyl, thienylalkyl or naphthylalkyl or (ii) cinnamyl, and Z is --CH.sub.2 OH, --CHO or --CONHR.sup.4 where R.sup.4 is --H or methyl,and their salts and solvates.These compounds inhibit blood platelet aggregation, bronchoconstriction and vasoconstriction, and may be formulated for use as antithrombotic and antiasthmatic agents.
    Type: Grant
    Filed: September 5, 1984
    Date of Patent: September 23, 1986
    Assignee: Glaxo Group Limited
    Inventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, Norman F. Hayes
  • Patent number: 4605654
    Abstract: The present invention relates to new 2-(arylalkyloxymethyl)morpholine derivatives, the preparation thereof and their application as drugs which are useful in the treatment of disorders of the central nervous system.The 2-(arylalkyloxymethyl)morpholine derivatives according to the invention correspond to the general formula (I): ##STR1## in which: Ar denotes an aromatic group and more especially the following radicals: ##STR2## in the case where Ar denotes a phenyl radical and R denotes a hydrogen atom, an alkyl, alkoxy or halogen group, a trifluoromethyl radical, a nitro or amino group, a hydroxy group or an arylalkyloxy group.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: August 12, 1986
    Assignee: P. F. Medicament
    Inventors: Henri Cousse, Gilbert Mouzin, Jean-Pierre Rieu, Mike Briley, Antoine Stenger
  • Patent number: 4596800
    Abstract: A compound of formula (I) ##STR1## or a pharmaceutically acceptable salt thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl;R.sup.2 is hydrogen or halogen;R.sup.3 is hydrogen or methyl;R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H or an ester or amide derivative thereof, O(CH.sub.2).sub.b M or --CO.sub.2 H or an ester or amide derivative thereofwhereina is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## wherein R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring; R.sup.5 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by carboxy or esters and amides thereof; or phenyl optionally substituted by C.sub.1-6 alkyl, halogen, alkoxy or trifluoromethyl;R.sup.8 is hydrogen or C.sub.1-6 alkyl or R.sup.8 together withR.sup.5 form a carbocyclic ring; andn is 1 or 2.Processes for preparing these compounds and their use in therapy is also described.
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: June 24, 1986
    Assignee: Beecham Group p.l.c.
    Inventors: Anthony T. Ainsworth, Richard M. Hindley
  • Patent number: 4593023
    Abstract: A compound of formula (I): ##STR1## or a pharmaceutically acceptable salt, thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl,R.sup.2 is hydrogen or halogen,R.sup.3 is hydrogen or methyl.R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H, --O(CH.sub.2).sub.b M, --CO.sub.2 H or an esteror amide derivative thereof in whicha is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## in which R.sup.5 and R.sup.6 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring, and n is 1 or 2; a process for preparing such a compound and its use in medicine and agriculture.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: June 3, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Richard M. Hindley
  • Patent number: 4584013
    Abstract: Novel cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.The cyclohexanedionecarboxylic acid derivatives have the formula I ##STR1## wherein A is an --OR.sub.2 or --NR.sub.3 R.sub.4 radical,B is hydroxyl, an --NHOR.sub.1 radical or a metal or ammonium salt thereofR is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each unsubstituted or substituted by halogen, C.sub.1 -C.sub.6 alkoxy or C.sub.2 -C.sub.4 alkylthio,R.sub.1 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.sub.6 alkynyl,R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl; C.sub.3 -C.sub.6 alkenyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.3 -C.sub.6 alkynyl; phenyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: April 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4536500
    Abstract: New aromatic derivatives having an activity antagonistic to calcium and corresponding to formula: ##STR1## in which: A represents a chain having any one of the following structures: ##STR2## Ar represents a group of structure: ##STR3## n takes the value 1 or 2 when R is different from H; m takes the value 2 or 3.
    Type: Grant
    Filed: December 21, 1982
    Date of Patent: August 20, 1985
    Assignee: Delalande S.A.
    Inventors: Guy R. Bourgery, Alain P. Lacour, Bernard M. Pourrias, Raphael Santamaria
  • Patent number: 4525586
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: June 25, 1985
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4517183
    Abstract: The present invention provides pharmaceutical compositions containing N-substituted aziridine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein X is a carboxyl, a cyano, an alkoxycarbonyl or an optionally substituted carbamoyl radical, R is a hydrogen atom, an aliphatic hydrocarbon radical which is saturated or can contain one or more unsaturations and can be substituted one or more times by halogen, alkoxy, hydroxyl, dialkylamino, dialkylaminoxy, cycloalkylamino, acylamino, acyl, nitro, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxyl, alkoxycarbonyl or carbamoyl or by cycloalkyl or cycloalkenyl radicals optionally carrying alkyl, alkoxy or alkoxycarbonyl radicals, optionally interrupted by hetero atoms and optionally bridged, or by an aryl, hetaryl, aryloxy, arylthio, acyloxy, alkoxycarbonylamino or isothioureido radical, or R is a cycloalkyl or cycloalkenyl radical optionally substituted by alkyl, alkoxy or oxo groups, optionally interrupted by hetero atoms and optionally bri
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: May 14, 1985
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elmar Bosies, Wolfgang Kampe, Max Thiel, Uwe Bicker, Dietmar Boerner
  • Patent number: 4499094
    Abstract: Compounds with the formula: ##STR1## in which R.sub.1 and R.sub.2 represent independently, a linear or branched alkyl, cycloalkyl, phenylalkyl or cycloalkylalkyl group. R.sub.1 and R.sub.2 may also represent an alkenyl or alkynyl group. R.sub.1 and R.sub.2 may also represent a group of the formula --R.sub.3 --Z--R.sub.4 in which R.sub.3 represents an alkylene group, on condition that at least 2 carbon atoms separate the nitrogen atom from the group Z; R.sub.4 represents an alkyl group, and Z an atom of oxygen, sulphur or the group >N--R.sub.5, R.sub.5 representing a hydrogen atom or an alkyl group. R.sub.1 and R.sub.2 may form, with the nitrogen atom to which they are attached, a heterocyclic ring. Ar represents a phenyl, pyridyl or thienyl group, or a substituted phenyl group, A and B representing independently, N or CH--, the group C representing the residue of a benzene or thiophene ring. These compounds can be used as medicaments, in particular, for the various applications of benzodiazepines.
    Type: Grant
    Filed: April 5, 1983
    Date of Patent: February 12, 1985
    Assignee: Pharmuka Laboratoires
    Inventors: Marie-Christine Dubroeucq, Christian Renault, Gerard Le Fur
  • Patent number: 4493823
    Abstract: This invention relates to topical cosmetic preparations. More particularly, this invention relates to a topical cosmetic preparation for the treatment of oily hair and seborrheic skin which comprises an effective amount of at least one compound of the formula ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3, any of which may be the same or different, each represent hydrogen, hydroxyl, or --OR.sub.4, where R.sub.4 is an alkyl of from 1 to 6 carbon atoms or a substituted or unsubstituted benzyl, or two of the groups R.sub.1, R.sub.2, and R.sub.3 represent methylenedioxy; X is a substituted or unsubstituted alkylene of from 1 to 3 carbon atoms; and Y is --COOH, --CN, --CONR.sub.5 R.sub.6, or --COOR.sub.7, where R.sub.5 and R.sub.6 each represent hydrogen, alkyl of from 1 to 6 carbon atoms, or substituted or unsubstituted aryl, or aralkyl, or together with the nitrogen atom R.sub.5 and R.sub.6 represent a heterocycle, and R.sub.7 is an alkyl of from 1 to 6 carbon atoms or a substituted or unsubstituted aralkyl.
    Type: Grant
    Filed: November 10, 1981
    Date of Patent: January 15, 1985
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hinrich Moller, Siegfried Wallat, Friedhelm Bartnik, Wolfgang Pittermann
  • Patent number: 4486349
    Abstract: Process for preparing a para-quinone or ortho-quinone derivative, possibly alkoxylated or aryloxylated, which consists in oxidizing respectively the corresponding hydroquinone or pyrocatechic derivative, by means of the complex prepared, in situ or separately, by combining a cuprous salt, a hydrocarbon substituted by a cyano group and molecular oxygen, the oxidation being possibly carried out in the presence of an alkoxylating or aryloxylating agent of the hydroxylated derivative type.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: December 4, 1984
    Assignee: Delalande, S.A.
    Inventors: Michel Maumy, Patrice J. G. Capdevielle, Philippe L. Dostert, Michel Langlois
  • Patent number: 4478598
    Abstract: The amphoteric styrene derivatives correspond to the formula ##STR1## in which X is oxygen, sulfur, a direct bond, --SO.sub.2 N(R.sub.5 --, --CON(R.sub.5 -- or --COO--, Y.sub.1 and Y.sub.2 independently of one another are C.sub.1 -C.sub.4 -alkylene or hydroxypropylene, R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.4 -alkyl or, together with the N atom, are a pyrrolidine, piperidine, hexamethyleneimine or morpholine ring, and R.sub.1, together with R.sub.5, is also a piperazine ring, R.sub.3 and R.sub.4 are hydrogen, C.sub.1-4 -alkyl, chlorine, C.sub.1-4 -alkoxy or C.sub.3-4 -alkenyl or together, in the o-position relative to one another, are a trimethylene or tetramethylene group, R.sub.5 is hydrogen, C.sub.1-4 -alkyl or cyanoethyl or, together with R.sub.1, is a piperazine ring, Q is --COO or --SO.sub.3 and n is the number 1 or 2, and can be prepared by reacting the corresponding amine compounds with a halide of the formula Hal--Y.sub.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: October 23, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans R. Meyer, Max Morf
  • Patent number: 4474782
    Abstract: Morpholine derivatives of the formula ##STR1## and their pharmaceutically acceptable acid addition salts possess analgesic and/or opiate antagonistic activity. In the formula R.sup.1 represents lower alkyl; R.sup.2 represents hydrogen, lower alkyl or (lower)alkoxymethyl; R.sup.3 represents hydrogen, lower alkyl, lower alkenyl, lower alkynyl, aryl(lower)alkyl, 2-tetrahydrofurylmethyl or cycloalkylmethyl and R.sup.4 represents a lower alkenyl or lower alkynyl group containing at least 3 carbon atoms and in which there is no unsaturated bond in the 1-position.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: October 2, 1984
    Assignee: John Wyeth & Brother, Ltd.
    Inventors: Alan C. White, Edwin T. Edington