Morpholine Ring Bonded Directly To The Nitrogen Patents (Class 544/164)
  • Patent number: 5468775
    Abstract: The present invention concerns enaminones having the formula: ##STR1## wherein R is from the group consisting of COOCH.sub.3 and COOC.sub.2 H.sub.5 ; R.sup.1 is from the group consisting of H and CH.sub.3 ; R.sup.2 is from the group consisting of H when R.sup.1 is CH.sub.3 and CH.sub.3 when R.sup.1 is H; and R.sup.3 is from the group of first radicals consisting of benzyl, phenethyl, disubstituted phenyl and trisubstituted phenyl. The substituted species are second radicals having positive lipophilicity selected from the group consisting of F, Cl, Br, and I.
    Type: Grant
    Filed: March 2, 1993
    Date of Patent: November 21, 1995
    Assignee: Howard University
    Inventors: Kenneth R. Scott, Jesse M. Nicholson, Ivan O. Edafiogho
  • Patent number: 5453517
    Abstract: The invention relates to fluorescent and/or reactive derivatives of 1,2-bis-(2-aminophenoxyethane)-N,N,N',N'-tetraacetic acid (BAPTA) according to the formula: ##STR1## where at least one of W and X is a functional group, with or without a spacer, that terminates in an alcohol or phenol, a thiol, a haloacetamide, an alkyl halide, an amine or aniline, a carboxylic acid, an anhydride, an isocyanate, an isothiocyanate, a maleimide, or an activated ester. The BAPTA-like molecule may be further substituted, one or more times, by additional functional groups with or without spacers or by CH.sub.3, NO.sub.2, CF.sub.3, F, Cl, Br, I, or carboxylic acid derivatives or pharmaceutically acceptable salts thereof, or by indolyl or benzofuran fluorophores. The functional groups allow for subsequent covalent attachment of one or more oxygen heterocycle fluorophores (e.g. fluorescein, coumarin, rhodamine); or polymolecular assemblies (e.g.
    Type: Grant
    Filed: February 25, 1992
    Date of Patent: September 26, 1995
    Assignee: Molecular Probes, Inc.
    Inventors: Michael A. Kuhn, Richard P. Haugland
  • Patent number: 5430025
    Abstract: Trifluoromethylketone compounds of the formula: ##STR1## wherein R.sup.1 is C.sub.1-6 alkyl which has one or two substituents selected from carboxy, esterified carboxy and di-C.sub.1-6 alkylcarbamoyl; phenyl(C.sub.1-6)alkyl, the phenyl moiety of which may have halogen or nitro or amino substituents and the alkyl moiety of which may have carboxy or esterified carboxy substituents; halo-phenyl; morpholino; or morpholino(C.sub.1-6)alkyl, R.sup.2 and R.sup.3 are each C.sub.1-6 alkyl, X is --or --NH--, and ##STR2## and pharmaceutically acceptable salts thereof are useful for inhibiting human elastase.
    Type: Grant
    Filed: November 30, 1993
    Date of Patent: July 4, 1995
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Keiji Hemmi, Ichiro Shima, Keisuke Imai, Hirokazu Tanaka
  • Patent number: 5420164
    Abstract: A cycloalkylurea compound of the formula (I): ##STR1## wherein each symbol is as defined in the specification, or a pharmaceutically acceptable salt thereof, which compound inhibits ACAT and is useful as hypolipidemic and antiatherosclerotic medicine.
    Type: Grant
    Filed: May 3, 1993
    Date of Patent: May 30, 1995
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tadashi Mishina, Kanou Harada, Joji Yasuoka, Hidenobu Kushuhara, Noriyoshi Izumi
  • Patent number: 5407959
    Abstract: Compounds of structure ##STR1## where W is selected from the group consisting of ##STR2## where Q is oxygen or sulfur, R.sup.7 and R.sup.8 are independently selected from hydrogen and alkyl, or R.sup.7 and R.sup.8, together with the nitrogen atoms to which they are attached, define a radical of formula ##STR3## L.sup.1 and L.sup.2 are independently selected from a valence bond, alkylene, propenylene, and propynylene; R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently selected from alkyl, alkoxy, haloalkyl, halogen, cyano, amino, alkoxycarbonyl, and dialkylaminocarbonyl; Y is oxygen, >NR.sup.11, where R.sup.11 is hydrogen or alkyl, or ##STR4## where n=0, 1, or 2; and R.sup.5 and R.sup.6 are alkyl, inhibit the biosynthesis of leukotrienes. These compounds are useful in the treatment or amelioration of allergic and inflammatory disease states.
    Type: Grant
    Filed: November 12, 1993
    Date of Patent: April 18, 1995
    Assignee: Abbott Laboratories
    Inventors: Joseph F. Dellaria, Anwer Basha, Lawrence A. Black, Linda J. Chernesky, Wendy Lee
  • Patent number: 5366997
    Abstract: There are disclosed cardiovascularly active compounds possessing antihypertensive properties, and pharmaceutical compositions containing these agents and a method of treating cardiovascular disorders with the compounds. The active components of the pharmaceutical compositions are compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently chosen from straight chain and branched chain alkyl and olefinic groups, which may be unsubstituted or substituted; or R.sub.1 and R.sub.2 together with the nitrogen atom they are bonded to form a heterocyclic group; and R.sub.3 is a pharmaceutically acceptable organic group selected from alkyl and olefinic groups which may be unsubstituted or substituted, acyl, a sulfonyl, sulfinyl, sulfenyl, carbonate, or carbamate derivative; or R.sub.3 is a group of the formula--(CH.sub.2).sub.n ONN(O)NR.sub.1 R.sub.2, wherein n is 2-8, and R.sub.1 and R.sub.2 are as described above. Novel compounds are disclosed wherein at least one of R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: November 22, 1994
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Larry K. Keefer, Tambra M. Dunams, Joseph E. Saavedra
  • Patent number: 5304659
    Abstract: A process for the preparation of a polycyclic dye of Formula (1): ##STR1## by reacting a compound of Formula (2): ##STR2## with a benzofuranone of the Formula (3): ##STR3## wherein: Ring A is unsubstituted or is substituted by from one to three groups;Ring B is unsubstituted, apart from the nitro group, or is substituted by one or two further groups;R is H, optionally substituted alkyl or optionally substituted aryl; andZ is an oxyammonium group, and certain novel compounds of Formula (2) are disclosed.The process provides a convenient route to polycyclic dyes which are useful for the coloration of synthetic textile materials particularly polyesters.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: April 19, 1994
    Assignee: Zeneca Limited
    Inventor: David J. Milner
  • Patent number: 5296591
    Abstract: The trifluoromethylketone derivatives (I) and pharmaceutically acceptable salts thereof have a human leukocyte elastase inhibiting activity and are useful as human leukocyte elastase inhibitors for treating or preventing degenerative diseases. The trifluoromethylketone derivatives (I) have the following formula: ##STR1## wherein R.sup.1 is C.sub.1-6 alkyl which has one or two substituents selected from carboxy, esterified carboxy and di-C.sub.1-6 alkylcarbamoyl; phenyl(C.sub.1-6) alkyl, the phenyl moiety of which may have halogen or nitro or amino substituents and the alkyl moiety of which may have carboxy or esterified carboxy substituents; halo-phenyl; morpholino; or morpholino(C.sub.1-6) alkyl,R.sup.2 and R.sup.3 are each C.sub.1-6 alkyl,X is -- or --NH--, andY is ##STR2## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: March 22, 1994
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Keiji Hemmi, Ichiro Shima, Keisuke Imai, Hirokazu Tanaka
  • Patent number: 5194608
    Abstract: A dipeptide derivative of formula (I) is provided, which is capable of inhibiting the enzymatic activity of renin and thereby depressing the renin-angiotensin system and lowering the blood pressure. ##STR1## wherein: R.sup.1 is C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, aryl, or heterocyclic radical;R.sup.2 is carbamoyl, aryl, 5- or 6-membered heterocyclic radical, C.sub.1 -C.sub.12 alkyl-S--, C.sub.1 -C.sub.12 alkyl-S--CH.sub.2 --, or C.sub.3 -C.sub.10 cycloalkyl-S--;R.sup.3 is aryl or 5- or 6-membered heterocyclic radical;R.sup.4 is R.sup.4' --SO.sub.2 or R.sup.4' --CO;R.sup.4' is aryl, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl; C.sub.3 -C.sub.10 cycloalkyl, or heterocyclic radical;X is CH.sub.2, NH, O, or S; andY is CO or NHSO.sub.2, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4' each may be substituted with one to three substituents.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: March 16, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tatsuo Toyoda, Toshihiro Fujioka, Kunio Hayashi, Masuhisa Nakamura, Naofumi Hashimoto
  • Patent number: 5185334
    Abstract: Novel 2,2-disubstituted glycerol-like compounds are disclosed for use as anti-allergic and anti-inflammatory compounds. The compounds are antagonists of platelet activating factor ("PAF"). Also disclosed are methods of synthesizing and using the compounds of the invention as well as pharmaceutical compositions thereof. The compounds have the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are as defined in the specification.
    Type: Grant
    Filed: September 6, 1991
    Date of Patent: February 9, 1993
    Assignee: Schering Corporation
    Inventors: Daniel Solomon, James J. Kaminski, Steven K. White, Laura S. Lehman de Gaeta, Ashit K. Ganguly
  • Patent number: 5149872
    Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.
    Type: Grant
    Filed: February 14, 1991
    Date of Patent: September 22, 1992
    Assignee: Enichem Anic S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
  • Patent number: 5086054
    Abstract: Novel arylcycloalkanepolyalkylamines useful as anti-psychotic, anti-ischemia, anti-stroke, anti-dementia and anti-convulsant agents. These arylcycloalkanepolyalkylamines are selective high-affinity ligands to the sigma binding-sites containing three basic units: arylcycloalkyl group, an amine group and an intermediate chain. Their preparation and use for treatment of psychoses, ischemia, stroke, dementia and convulsions are also disclosed.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: February 4, 1992
    Assignee: SRI International
    Inventor: Daniel W. Parish
  • Patent number: 5075337
    Abstract: Deuterated 2-alkylaminoacetamide compounds are described having the alpha carbon of the alkyl side chain of the compounds substituted by one or two deuterium atoms. These compounds have pharmacokinetic properties which enable treatment of CNS diseases with lower toxic effects. These compounds are also useful in evaluating the metabolic fate of non-deuterated counterpart compounds. Of particular interest are compounds of Formula I: ##STR1## wherein X is deutero or hydrido; wherein R.sup.1 is selected from alkyl and aralkenyl; wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and alkyl; wherein each of R.sup.1, R.sup.2 and R.sup.3 having a substitutable position may be substituted with one or more halo radicals; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: December 24, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Alex A. Cordi, Philippe Janssens de Varebeke, Hugo Gorissen
  • Patent number: 5068371
    Abstract: Titanocenes of the formula I ##STR1## in which R.sup.1 are cyclopentadienyl.sup..crclbar. groups and R.sup.2 and R.sup.3 are aromatic radicals which are substituted in both ortho-positions by fluorine and, in addition, are substituted by a pyrrylalkyl group, amidoalkyl group or imidoalkyl group, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated compounds.
    Type: Grant
    Filed: May 23, 1990
    Date of Patent: November 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Eginhard Steiner, Harry Beyeler, Rinaldo Husler
  • Patent number: 5041462
    Abstract: Novel substituted acetamide compounds of the formula ##STR1## wherein R.sup.1 is hydrogen atom, a lower alkyl group, a lower acyl group, or an aryl group; R.sup.2 is cyano group or aminocarbonyl group; R.sup.3 is a halogen atom, nitro group, a lower alkoxy group, a group of the formula: --NR.sup.4 R.sup.5 (wherein R.sup.4 is hydrogen atom, a lower alkyl group or a group of the formula: --COCH.sub.2 OR.sup.1 ; R.sup.5 is hydrogen atom or a lower alkyl group), or a cyclic amino group of the formula: ##STR2## (wherein R.sup.6 and R.sup.7 are each an alkylene group having 1 to 3 carbon atoms, and X is oxygen atom or methylene), or a pharmaceutically acceptable acid addition salt thereof, which have excellent anti-allergic activity and are useful for the prophylaxis and treatment of various allergic diseases, and a pharmaceutical composition containing the amide compound as set forth above as an active ingredient.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: August 20, 1991
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Hiroaki Taguchi, Takeo Katsushima, Masakazu Ban, Mitsuru Takahashi, Kiyotaka Shinoda, Akihiko Watanabe
  • Patent number: 5017721
    Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 21, 1991
    Assignee: Enichim ANIC S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
  • Patent number: 4992089
    Abstract: A compound of formula (I) ##STR1## or a zwitterion derivative thereof; wherein R.sup.1, R.sup.2 and R.sup.3 are each independently optionally substituted alkyl or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a 5- or 6- membered heterocyclic ring; R.sup.4 is hydrogen, nitro, halo, alkyl or CF.sub.3 ; R.sup.5 is halo; and .crclbar. and Z is an anion. The compounds are useful as herbicides.
    Type: Grant
    Filed: November 18, 1986
    Date of Patent: February 12, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Cartwright, David J. Collins
  • Patent number: 4940707
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are lower-alkyl; or together are alkylene with 3-5 C-atoms in a straight chain; one of the residues R.sup.3 and R.sup.4 is hydrogen and the other is hydrogen or lower-alkyl; R.sup.6 and R.sup.7 are hydrogen or lower-alkyl; R.sup.5 and R.sup.8 are hydrogen, lower-alkyl, lower-alkoxy or halogen; X signifies --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sup.9 ; R.sup.9 is hydrogen, lower-alkyl or acyl; Y is --S(O).sub.m R.sup.10 or --NHet and, where X is --NR.sup.9 --, --S--, --SO-- or --SO.sub.2 --, also --N(R.sup.11).sub.2 or --OR.sup.12 ; R.sup.10 is lower-alkyl; R.sup.11 and R.sup.12 are hydrogen, lower-alkyl or acyl; --NHet is a 5-8 membered, saturated or unsaturated, monocyclic heterocycle, attached via a N-atom; n is 2, 3 or 4 and m is 0, 1 or 2, are described. The compounds of formula I are useful as agents for the treatment of disorders such as neoplasms, dermatoses or ageing of the skin.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: July 10, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Michael Klaus, Peter Mohr, Ekkehard Weiss
  • Patent number: 4940727
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as anti-hypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee, Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker
  • Patent number: 4910121
    Abstract: Titanocenes containing .pi.-cyclopentadienyl ligands, in which one or two carbocyclic or heterocyclic aromatic rings are attached to the metal atom, said aromatic rings being substituted by fluorine in at least one of the two ortho-positions relative to the metal-carbon bonds, are suitable photoinitiators for the photopolymerization of ethylenically unsaturated substrates. They are distinguished by high sensitivity, stability to air and heat, and are very effective in the range from UV light to visible light.
    Type: Grant
    Filed: July 28, 1987
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Riediker, Martin Roth, Niklaus Buhler, Joseph Berger
  • Patent number: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4766116
    Abstract: A diaryl butyric acid derivative having the general formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an acyl group having 2 to 4 carbon atoms; R.sup.2 represents an alkyl group having 1 to 3 carbon atoms; andX represents a variety of substituents.This diaryl butyric acid derivative or the pharmaceutically acceptable salt thereof can be prepared by reacting a benzoxepin derivative having the general formula: ##STR2## wherein R.sup.2 is the same as defined above with an amine or alcohol derivative having the general formula;X--Hwherein X is the same as defined above in the presence of an acid catalyst at room temperature or at an elevated temperature and, optionally, further reading the reaction product with an alkylation agent having 1 to 3 carbon atoms or an acylation agent having 2 to 4 carbon atoms.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: August 23, 1988
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Kayoko Imao, Kunihiro Sumoto
  • Patent number: 4762829
    Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.
    Type: Grant
    Filed: October 23, 1986
    Date of Patent: August 9, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
  • Patent number: 4742058
    Abstract: A novel polyprenyl compound such as a polyprenyl carboxylic acid amide is disclosed. It has antithrombic and antiplatelet aggregation activity.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: May 3, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Tohru Fujimori, Koukichi Harada, Shinichi Kitamura
  • Patent number: 4728647
    Abstract: Compounds of formula: ##STR1## in which V and W are H, halogen, alkyl (1-4C) or alkoxy (1-4C), amino, or acylamino,Z is phenyl, optionally substituted, thienyl, or pyridyl,R.sub.1 is alkyl (1-6C), alkoxyalkyl, cycloalkyl (3-6C), phenyl, phenylalkyl, or cycloalkylalkyl,R.sub.2 is alkyl (1-6C), alkoxyalkyl, cycloalkyl (3-6C), phenyl, phenylalkyl, cycloalkylalkyl, or morpholino, andNR.sub.1 R.sub.2 can also be pyrrolidino, optionally substituted piperidino, optionally substituted morpholino, thiomorpholino, optionally substituted piperazino, or an optionally substituted piperazinone, are useful as anxiolytic agents.
    Type: Grant
    Filed: May 28, 1986
    Date of Patent: March 1, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jesus Benavides, Marie-Christine Dubroeucq, Gerard Le Fur, Christian Renault
  • Patent number: 4725608
    Abstract: New semicarbazide derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen,R.sup.2 is hydrogen, lower alkyl, ar(lower)alkyl, lower alkenyl or aryl,R.sup.3 is lower alkyl, ar(lower)alkyl, lower alkenyl or aryl, orR.sup.2 and R.sup.3 are taken together to form (C.sub.2 -C.sub.6)alkylidene group optionally substituted with aryl or taken together with the adjacent nitrogen atom to form a saturated or unsaturated, 5- or 6-membered heterocyclic group optionally substituted with aryl; orR.sup.1 and R.sup.2 are taken together with the adjacent nitrogen atoms to form a saturated or unsaturated, 5- or 6-membered heterocyclic group or 1,2-diazaspiroalkane-1,2-diyl group,R.sup.3 is hydrogen, lower alkyl, ar(lower)alkyl, lower alkenyl or aryl;R.sup.4 is aryl which may have substituent(s) selected from lower alkyl, halogen, lower alkoxy, lower alkylamino, halo(lower)alkyl, hydroxy, lower alkanoyl, esterified carboxy and carboxy,R.sup.
    Type: Grant
    Filed: November 21, 1984
    Date of Patent: February 16, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Osamu Nakaguchi, Norihiko Shimazaki, Yoshio Kawai, Masashi Hashimoto, Michie Nakatuka
  • Patent number: 4698442
    Abstract: .alpha.-amino acids having a substituted .omega.-guanidino group are disclosed herein.
    Type: Grant
    Filed: June 13, 1986
    Date of Patent: October 6, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John J. Nestor, Brian H. Vickery
  • Patent number: 4693745
    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.3 -C.sub.6 cycloalkyl,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.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, nitro or cyano; one of R.sub.3 and R.sub.4 is methoxy; orR.sub.3 and R.sub.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: September 15, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans-Georg Brunner
  • Patent number: 4593039
    Abstract: 1-Aryloxy-3-(substituted aminoalkylamino)-2-propanols and pharmaceutically acceptable salts thereof have .beta.-adrenergic blocking activity with some cardioselectivity and hence are useful as antihypertensive, antianginal, antiarrhythmic and cardioprotective agents and in the treatment of elevated intraocular pressure such as glaucoma.
    Type: Grant
    Filed: April 2, 1984
    Date of Patent: June 3, 1986
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Sandor L. Varga, Gerald S. Ponticello
  • Patent number: 4564677
    Abstract: Disclosed is a method of preparing N-amino compounds from corresponding secondary amines by reacting a secondary amine with nitrous acid and zinc in a neutral pH reaction media to form the corresponding N-amine.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: January 14, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventor: Martin L. Kantor
  • Patent number: 4557871
    Abstract: Novel styrene derivatives of the general formula ##STR1## wherein X is hydrogen or halogen, X.sup.1 is halogen, R is hydrogen or methyl, Y is hydroxymethyl, carboxyl, --COOR.sup.1 or --COR.sup.2 wherein R.sup.1 is prenyl, geranyl, farnesyl, cyclohexyl, phthalidyl, straight or branched chain alkyl having 1 to 6 carbon atoms, or said alkyl substituted with hydroxy, methoxy, pyridyl or alkanoyloxy having 2 to 16 carbon atoms, and R.sup.2 is amino, hydroxyamino mono-(or di-)alkylamino in which the alkyl moiety contains 1 or 2 carbon atoms, ethoxycarbonylmethylamino, carboxymethylamino, thiazolylamino, cyclohexylamino, pyridylamino, morpholino, N-methylpiperazino, phenylamino, phenylamino substituted with one or two of halogen, hydroxy, methyl, methoxy, trifluoromethyl or carboxyl at the phenyl ring, and the pharmaceutically acceptable salts thereof when Y is carboxyl are disclosed. These compounds exhibit high and long-lasting anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: December 10, 1985
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
  • Patent number: 4496542
    Abstract: Compounds of the formula ##STR1## wherein R and R.sub.9 are independently hydroxy and lower alkoxy,R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, aryl-lower alkyl having from 7 to 12 carbon atoms, or heterocyclic-lower alkyl having from 6 to 12 carbon atoms,R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are hydrogen or lower alkyl,R.sub.6 is heterocyclic and their pharmaceutically acceptable, nontoxic acid addition salts and where R or R.sub.9 or both are hydroxy, their pharmaceutically acceptable, nontoxic basic salts, possess antihypertensive activity.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: January 29, 1985
    Assignee: USV Pharmaceutical Corporation
    Inventors: Jerry W. Skiles, Raymond D. Youssefyeh, John T. Suh, Howard Jones
  • Patent number: 4463168
    Abstract: The instant invention relates to a process for the formation of polylactone polymers which are terminated on one end by a tertiary amine group, and on the other end by a hydroxyl group. An .epsilon.-caprolactone is reacted with an aromatic organic amine in the presence of a catalyst.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: July 31, 1984
    Assignee: Exxon Research and Engineering Co.
    Inventor: Robert D. Lundberg
  • Patent number: 4430505
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: February 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann
  • Patent number: 4388238
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Primary amines and alcohols are reacted with organic compounds having carbonyl groups at 120.degree. to 350.degree. C. Suitable carbonyl-containing compounds include N-unsubstituted urethanes. N-mono-substituted, N,N'-disubstituted ureas, or polyureas may be used in combination with the N-unsubstituted urethane. The product urethanes are particularly suitable for the preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: June 14, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Rudolf Fauss, Kurt Findeisen
  • Patent number: 4377687
    Abstract: This invention relates to compounds having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, acyl, trifluoroacetyl, straight chained and branched alkyl groups with up to 6 carbon atoms, such alkyl groups with up to 3 substituents selected from the group consisting of OH, OSO.sub.2 CH.sub.3, COOH, COOR, CONH.sub.2 and Hal, where R is an alkyl group with up to 6 carbon atoms, and R.sub.1 and R.sub.2 together form a heterocyclic ring containing 4 to 6 carbon atoms and optionally further heteroatoms and such rings with up to 3 substituents selected from the group consisting of lower alkyl, OH, COOH, COOR, CONH.sub.2, where R has the above meaning, the chloroethyl nitrosoureido group and Hal, and Hal is selected from the group consisting of chlorine and fluorine, which heterocyclic ring is not the para-methyl piperazine group, said nitroso ureas having a tumor inhibiting effect.
    Type: Grant
    Filed: April 22, 1981
    Date of Patent: March 22, 1983
    Assignee: Stiftung Deutsches Krebsforschungszentrum
    Inventor: Gerhard Eisenbrand
  • Patent number: 4348406
    Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: September 7, 1982
    Assignee: Schering Corporation
    Inventor: M. Mehdi Nafissi-Varchei
  • Patent number: 4334073
    Abstract: Process for the preparation of an alpha-hydroxycarboxylic acid amide compound of the formula ##STR1## wherein R.sup.1 is hydrogen or alkyl; andR.sup.2 and R.sup.3 are individually selected from hydrogen, alkyl, alkenyl, alkynyl, aralkyl, cycloalkyl or aryl, each of which may be optionally substituted, or a nitrogen-containing heterocyclic radical; orR.sup.2 and R.sup.3, together with the nitrogen atom to which they are bonded, represent an optionally benzo-fused monocyclic or bicyclic ring, which ring may be substituted and may be partially unsaturated,which process comprises reacting in a first stage an alpha-halocarboxylic acid amide of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are identified as above; andHal is chlorine or bromine,with an alkali metal acetate or alkaline earth metal acetate in the presence of a quaternary ammonium salt at a temperature between 20.degree. and 200.degree. C.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: June 8, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 4331680
    Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.
    Type: Grant
    Filed: August 25, 1980
    Date of Patent: May 25, 1982
    Assignee: The Boots Company
    Inventors: David P. Giles, John C. Kerry, Antonin Kozlik, Bryan H. Palmer, Stephen W. Shutler, Robert J. Willis
  • Patent number: 4329293
    Abstract: An improved process is disclosed for sulfenylating carbamates in the presence of a solvent and acid acceptor, in which the reaction between a carbamate and a sulfenyl halide is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide. Several methods for preparing and utilizing the complex in the reaction are disclosed and exemplified.
    Type: Grant
    Filed: October 31, 1980
    Date of Patent: May 11, 1982
    Assignee: FMC Corporation
    Inventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
  • Patent number: 4303788
    Abstract: Certain 2-oximino-tetrahydro-1,4-oxazin-3-one and 5-oximino-1,3-oxazolidin-4-one carbamate esters exhibit outstanding miticidal, insecticidal and nematodicial activity; certain 2-oximino-tetrahydro-1,4-oxazin-3-ones and 5-oximino-1,3-oxazolidin-4-ones are useful intermediates in the preparation of pesticidally active carbamate compounds.
    Type: Grant
    Filed: May 9, 1980
    Date of Patent: December 1, 1981
    Assignee: Union Carbide Corporation
    Inventors: John A. Durden, Jr., Arthur P. Kurtz, Jr.
  • Patent number: 4281188
    Abstract: This invention provides benzodiazepine derivatives of the general formula ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or a lower alkyl group, R.sup.3 represents a halogen atom and R.sup.4 represents a hydrogen or halogen atom and either R.sup.5 represents a hydrogen atom or a lower alkyl group and R.sup.6 represents a lower alkyl, lower hydroxyalkyl or lower acyloxyalkyl group or R.sup.5 represents a hydrogen atom and R.sup.6 represents an aryl or lower aralkyl group or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached represent a 3-membered to 7-membered heterocycle which, when it is at least 5-membered, can contain as a ring member an oxygen or sulphur atom or a group of the formula >N--R.sup.7 in which R.sup.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: July 28, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert E. Fischli, Andre Szente
  • Patent number: 4268511
    Abstract: This invention relates to compounds having the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently hydrogen, a C.sub.1-4 alkyl group or an aliphatic or aromatic acyl group, provided R.sub.1 and R.sub.2 are not simultaneously hydrogen, or, together with the nitrogen atom to which they are attached, R.sub.1 and R.sub.2 form a 5- or 6-membered ring which may carry another heteroatom; R.sub.3 is a C.sub.1-4 alkyl group; and R.sub.4 and R.sub.5 represent independently a hydrogen or halogen atom, a C.sub.1-4 alkyl group or a C.sub.1-4 alkoxy group; and the acid addition salts of the above compounds. Said new compounds have an anxiolytic and diuretic action, together with a spasmolytic action of non-.alpha.-adrenalytic nature on the unstriated muscle fibers.
    Type: Grant
    Filed: March 11, 1980
    Date of Patent: May 19, 1981
    Assignee: Berri-Balzac
    Inventors: Rene Baronnet, Raymond Callendret
  • Patent number: 4256800
    Abstract: The antistatic composition for application to flat fibrous articles such as textiles, carpets, fabrics and the like which comprises a salt of a polymeric acid with an amine of the general formula ##STR1## wherein A=H, --OR.sub.2, ##STR2## R.sub.1 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.2 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.3 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.
    Type: Grant
    Filed: January 18, 1978
    Date of Patent: March 17, 1981
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Dolf Stockhausen, Reinmar Peppmoller
  • Patent number: 4237132
    Abstract: A series of new 4,6-disubstituted 2-morpholinone derivatives were prepared either by a reaction of corresponding epoxide derivatives with phenylglycine derivatives or by the reaction of isopropanol derivatives with carboxylic acid derivatives. The new morpholinone derivatives are useful for the prevention or the treatment of arteriosclerosis.
    Type: Grant
    Filed: June 4, 1976
    Date of Patent: December 2, 1980
    Assignee: Nippon Shinyaku Co., Ltd.
    Inventors: Hiromu Murai, Katsuya Ohata, Hiroshi Enomoto, Shoichi Chokai, Mitsuhiro Maehara, Katsuhide Saito, Takayuki Ozaki
  • Patent number: 4234580
    Abstract: Carbamate thiosulfenylcarbamoyl fluoride compounds are insecticidal and miticidal compounds and are also useful intermediates in the preparation of pesticidally active bis-carbamate disulfide compounds.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: November 18, 1980
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4202839
    Abstract: N-Amino substituted aniline and 1,3-phenylenediamine compounds having 1 or 2 nitro groups on the aromatic ring. The compounds are useful as herbicides and as intermediates for preparing herbicides.
    Type: Grant
    Filed: December 26, 1978
    Date of Patent: May 13, 1980
    Assignee: United States Borax & Chemical Corporation
    Inventors: Don L. Hunter, William G. Woods, James D. Stone, Cecil W. LeFevre
  • Patent number: 4172945
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 30, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
  • Patent number: 4169894
    Abstract: Unsymmetrical N-substituted bis-carbamoyloxy disulfide compounds exhibit outstanding nematocidal, miticidal and insecticidal activity, coupled with substantially reduced mammalian toxicity and phytotoxicity as compared to known pesticidal compounds having a comparable spectrum of activity against insect, arachnid and nematode pests.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: October 2, 1979
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4161591
    Abstract: Substituted 2-(carbamoyl)oxyimino-3-imino-butyramides and 2-(carbamoyl)oxyimino-3-iminobutyrates of the formula ##STR1## where Q is --OR.sub.4 or --NR.sub.5 R.sub.6, and A, R, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are as hereinafter defined are useful as aphicides. The compounds are made by reacting an amine with a substituted 2-hydroxyiminoacetoacetamide (or 2-hydroxyiminopropionylacetamide) or an alkyl 2-hydroxyiminoacetoacetate (or 2-hydroxyiminopropionylacetate), then carbamylating the resulting substituted 2-hydroxyimino-3-iminobutyramide (or 2-hydroxyimino-3-iminovaleramide) or 2-hydroxyimino-3-iminobutyrate (or 2-hydroxyimino-3-iminovalerate).
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: July 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Russell F. Bellina