Sulfur And Acyclic Nitrogen Bonded Directly To The Same Carbon Patents (Class 546/331)
  • Patent number: 5330737
    Abstract: The present invention relates particularly to novel aminothiol ligands that are suitable for complexing with a radionuclide, such as Tc, Re, or Ga, and are useful as general imaging agents for diagnostic purposes. The ligands have the general formulae (I) and (II): ##STR1## wherein for formula I, R.sup.1 -R.sup.4, R.sup.6, R.sup.7 and R.sup.9 -R.sup.14 can each be one of H, alkyl, aryl, hydroxyalkyl, alkoxycarbonyl, etc.; R.sup.5 and R.sup.8 are suitable sulfur protecting groups; m and n are 1-3; B can be one of C(O)CHR.sup.6 CHR.sup.7 SR.sup.8, CHR.sup.9 CHR.sup.10 C(O)NHR.sup.11, or C(O)CHR.sup.12 CHR.sup.13 NHR.sup.14 ;and wherein for formula II, R.sup.15 -R.sup.18, R.sup.20 and R.sup.21 are defined in the same manner as R.sup.1 above; D and E are either C(O) or CHR.sup.17 ; F is either (CH.sub.2).sub.d NR.sup.18 (CH.sub.2).sub.e SR.sup.19 or CHNR.sup.20 R.sup.21 (CH.sub.2).sub.f SR.sup.22 ; R.sup.19 and R.sup.22 are defined in the same manner as R.sup.5 above; d, e and f are 1-3.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: July 19, 1994
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: Raghavan Rajagopalan
  • Patent number: 5286736
    Abstract: New pyridyl derivatives of the formula ##STR1## wherein R.sub.1 to R.sub.6, A, X and n are as defined herein, the enantiomers thereof, the cis- and trans-isomers thereof if R.sub.4 and R.sub.5 together represent a carbon-carbon bond, and the addition salts thereof. The new pyridyl derivatives have antithrombotic activity and thromboxane-mediated activities. The new compounds are also simultaneously thromboxane antagonists (TRA) and thromboxane synthesis inhibitors (TSH). They also have an effect on PGE.sub.2 -production.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: February 15, 1994
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Rainer Soyka, Wolfgang Eisert, Thomas Mueller, Johannes Weisenberger
  • Patent number: 5281715
    Abstract: A method of treatment of tumors is provided based upon a compound of the formula ##STR1##Some aspects of the invention were supported in part by U.S. Public Health Service Grant CA-02817 from the National Cancer Institute and support from the Northeast NMR Facility at Yale University insofar as the use of high resolution NMR spectra is concerned that was made possible by a grant from the Chemical Division of the National Science Foundation (Grant No. CHE-7916210).
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: January 25, 1994
    Assignee: Yale University
    Inventors: Alan C. Sartorelli, Tai-Shun Lin
  • Patent number: 5276045
    Abstract: A thioformamide derivative of the formula: ##STR1## wherein R represents alkyl, A represents optionally substituted pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]pyridin-6-yl, or phenyl and Y represents a valency bond, methylene or ethylene, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aryloxyalkyl, aromatic heterocyclylalkyl or aromatic heterocyclyloxyalkyl group or a group ZC(.dbd.O)-- in which Z represents optionally substituted alkyl, aryl, or aromatic heterocyclic, n represents 0 or 1, and when n represents 0, R.sup.1 may represent a hydrogen atom, optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aryloxyalkyl, aromatic heterocyclylalkyl or aromatic heterocyclyloxyalkyl group or a group ZC(.dbd.O)-- or ZSO.sub.2 --, and when n represents 1, R.sup.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: January 4, 1994
    Assignee: Rhone-Poulenc Sante
    Inventors: Terance W. Hart, Bernard Y. J. Vacher, Roger J. A. Walsh
  • Patent number: 5273977
    Abstract: Substituted tetrahydropyridines and hydroxypiperidines and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of the same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: December 28, 1993
    Assignee: Warner-Lambert Company
    Inventors: Shelly Glase, Juan C. Jaen, Sarah J. Smith, Lawrence D. Wise
  • Patent number: 5256677
    Abstract: Compounds are disclosed which are retroviral protease inhibitors. Also disclosed are methods of using the compounds and compositions for inhibiting a retroviral protease and for treating an HIV infection.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: October 26, 1993
    Assignee: Abbott Laboratories
    Inventors: Hing L. Sham, Daniel W. Norbeck, Dale J. Kempf, Chen Zhao
  • Patent number: 5250542
    Abstract: 3,4,4-trisubstitutedpiperidinyl-N-alkylcarboxylates and intermediates for their preparation are provided. These piperidine-N-alkylcarboxylates are useful as peripheral opioid antagonists.
    Type: Grant
    Filed: July 17, 1992
    Date of Patent: October 5, 1993
    Assignee: Eli Lilly and Company
    Inventors: Buddy E. Cantrell, Dennis M. Zimmerman
  • Patent number: 5246950
    Abstract: Thioformamide derivatives of the formula (I) ##STR1## wherein R represents an alkyl group; A represents either:(1) a phenyl group which is optionally substituted; or(2) heteroaromatic group (e.g. pyrid-3-yl, quinolin-3-yl);Y represents:an ethylene or methylene group or a direct bond; and B represents either:a) a phenyl, pyridyl, furyl or thienyl group, each of which may be optionally substituted, orb) a straight- or branched-chain alkyl, alkenyl, or cycloalkyl group, each of which may be optionally substituted.These compounds may be formulated into pharmaceutical preparations and have utility in the treatment of disorders associated with smooth muscle contraction.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: September 21, 1993
    Assignee: Rhone-Poulenc Sante
    Inventors: Terance W. Hart, Bernard Y. J. Vacher, Brian W. Sharp
  • Patent number: 5236921
    Abstract: The invention relates to compounds of formula: ##STR1## in which Y represents--either a group Cy--N in whichCy represents a phenyl, optionally substituted; a C.sub.3 -C.sub.7 cycloalkyl group; a pyrimidinyl group or a pyridyl group;or a group ##STR2## in which Ar represents a phenyl, optionally substituted, a pyridyl group; a thienyl group;x is zero or one;X represents a hydroxyl, a C.sub.1 -C.sub.4 alkoxy; a hydroxyalkyl; a C.sub.1 -C.sub.4 acyloxy; a phenacyloxy; a carboxyl; a C.sub.1 -C.sub.4 carbalkoxy; a cyano; an aminoalkylene; a group --N--(X.sub.1).sub.2 in which the groups X.sub.1 independently represent hydrogen, a C.sub.1 -C.sub.4 alkyl; a group ##STR3## in which Alk represents a C.sub.1 -C.sub.6 alkyl; a group ##STR4## in which the Alk.sub.1 is a C.sub.1 -C.sub.3 alkylene and Alk'.sub.1 is a C.sub.1 -C.sub.3 alkyl; a C.sub.1 -C.sub.4 acyl; a group --S--X.sub.2 in which X.sub.2 represents hydrogen or a C.sub.1 -C.sub.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: August 17, 1993
    Assignee: Sanofi
    Inventors: Xavier Emonds-Ai, Pierre Goulaouic, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5225423
    Abstract: A butenone compound having the general formula I: ##STR1## wherein R.sup.1 represents a pyridyl or thiazolyl group bearing one or more substituents independantly selected from halogen atoms, alkyl, alkoxy, alkylthio, haloalkyl, cyano, alkoxycarbonyl, alkylamino and dialkylamino; R.sup.2 represents a hydrogen atom, an alkyl group or an alkylcarbonyl group; R.sup.3 represents an alkyl group; R.sup.4 represents a haloalkyl group; X represents a sulphur atom or a group of formula N--R.sup.5, wherein R.sup.5 represents a hydrogen atom, an alkyl group or an alkylcarbonyl group; and n is 0 or 1, methods for their preparation and their use in combating pests.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: July 6, 1993
    Assignee: Shell Research Limited
    Inventors: Antonio Mete, Lai C. Chan
  • Patent number: 5204357
    Abstract: The invention relates to compounds of the formula I ##STR1## in which A represents a substituted thio-, sulfinyl- or sulfonyl-alkanoyl radical or a four- to eleven-membered heterocycle, B is an amino acid residue, R.sup.1 denotes hydrogen (substituted) alkyl, (substituted)cycloalkyl or aryl, R.sup.2 represents hydrogen, (substituted)alkyl or aryl, R.sup.3 denotes a radical of the formula --(CH.sub.2).sub.q --(X).sub.r --(CH.sub.2).sub.s --R.sup.6 with X denoting CF.sub.2, CO or CHR.sup.8, R.sup.6 denoting a (substituted)heteroaromatic, R.sup.8 denoting alkyl, alkoxy, alkylthio, alkylamino, hydroxyl, azide or halogen, q and s denoting 1 to 4, and r denoting 0 or 1, and R.sup.9 is hydrogen, (substituted)alkyl, alkanoyl, cycloalkanoyl, (substituted) aroyl or (substituted)aryl, and to the salts thereof. In addition, processes for the preparation of these compounds, and the use thereof as renin inhibitors are described.
    Type: Grant
    Filed: February 14, 1989
    Date of Patent: April 20, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
  • Patent number: 5190961
    Abstract: Thiourea derivatives represented by the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each represents a lower alkyl group, or R.sub.1 or R.sub.2 taken together represent a group having the formula --(CH.sub.2).sub.m --in which m is 4 or 5, R.sub.3 represents a lower alkyl group or a cycloalkyl group or a group having the formula--(CH.sub.2).sub.l --R.sub.4 in which R.sub.4 is a phenyl, naphthyl, pyridyl, furyl or thienyl group optionally having 1-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, phenoxy, lower alkylthio, hydroxy, halogen, nitro, cyano and trifluoromethyl, and l represents an integer of 0 to 2 and n represents an integer of 1 to 5 or a physiologically acceptable salt thereof.The compounds of the invention are useful as a therapeutic agent for peptic ulcers which is also effective on prevention of the recurrence after discontinuation of the administration due to the antimicrobial activity against Helicobacter pyroli.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: March 2, 1993
    Assignee: Terumo Kabushiki Kaisha
    Inventors: Hirokazu Hasegawa, Isamu Endo, Shingo Koyama, Masashi Isozaki, Yukari Yoshiyama, Shigenori Nozawa, Norio Arakawa
  • Patent number: 5180831
    Abstract: Quaternary pyridinium compounds, their use in inhibiting acetylcholinesterase, their roles in the prophylaxis and treatment of organophosphate poisoning, their roles in anticholinesterase therapy and their roles as agents mimicking or opposing the actions of the natural neurotransmitter acetylcholine.
    Type: Grant
    Filed: August 10, 1990
    Date of Patent: January 19, 1993
    Assignee: Georgia Tech Research Corporation
    Inventors: James C. Powers, Sheldon W. May, Maria A. Hernandez, Steve Thornton, Jan Glinski
  • Patent number: 5164395
    Abstract: The present invention relates to a novel ribonucleotide reductase inhibitor and new combinations comprising an antiviral compound, such as acyclovir, and a thiocarbonohydrazone ribonucleotide reductase inhibitor for the chemotherapeutic treatment of virus infections, especiallly viruses of the herpes group.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: November 17, 1992
    Assignee: Burroughs Wellcome Co.
    Inventor: Todd A. Blumenkopf
  • Patent number: 5151438
    Abstract: Compounds are disclosed which are retroviral protease inhibitors. Also disclosed are methods of using the compounds and compositions for inhibiting a retroviral protease and for treating an HIV infection.
    Type: Grant
    Filed: March 27, 1991
    Date of Patent: September 29, 1992
    Assignee: Abbott Laboratories
    Inventors: Hing L. Sham, Daniel W. Norbeck, Dale J. Kempf, Chen Zhao
  • Patent number: 5151436
    Abstract: Therapeutically useful thioformamide derivatives of the formula: ##STR1## wherein R represents alkyl, Het represents pyrid-3-yl, isoquinolin-4-yl, tetrahydroquinolin-3-yl, quinolin-3-yl, pyridazin-4-yl, pyrimid-5-yl, thiazol-5-yl, thieno[2,3-b]-pyridin-5-yl, pyrazin-2-yl, indol-3-yl and thieno[3,2-b]-pyridin-6-yl, Y represents ethylene, methylene or a valency bond, and X represents carbonyl, hydroxymethylene, >C.dbd.NOR.sup.1, >C.dbd.NN(R.sup.1).sub.2 or >C.dbd.NN(R.sup.1)CON(R.sup.1).sub.2 in which R.sup.1 represents hydrogen or optionally substituted alkyl, benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl or pyrid-3-ylmethyl, or two R.sup.1 substituents on the same nitrogen atom may together form an optionally substituted alkylene radical chain and salts thereof, processes for their preparation and compositions containing them are described.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: September 29, 1992
    Assignee: Rhone-Poulenc Sante
    Inventors: David C. Cook, Terance W. Hart, Iain M. Mc Lay, Malcolm N. Palfreyman, Brian W. Sharp, Roger J. A. Walsh
  • Patent number: 5137923
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 --OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which: 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: August 11, 1992
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 5118697
    Abstract: Novel cyclic beta-ketoamides which contain an aryl moiety having utility as blood cholesterol lowering agents rendering them useful in the treatment of atherosclerosis.
    Type: Grant
    Filed: March 6, 1991
    Date of Patent: June 2, 1992
    Assignee: Warner-Lambert Company
    Inventors: Corinne E. Augelli-Szafran, Bharat K. Trivedi
  • Patent number: 5116861
    Abstract: Novel nitrosothiol derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently a hydrogen atom or a hydrocarbon residue which may be substituted; R.sup.3 is a hydrogen atom, an acyl group or a hydrocarbon residue which may be substituted; X.sup.1 is a hydrogen atom, an acyl group, a lower alkoxy group or a hydrocarbon residue which may be substituted; X.sup.2 is an acyl group or a carboxyl group which may be esterified or which may form an amide; with proviso that when X.sup.2 is a carboxyl group X.sup.1 is not a hydrogen atom or acetyl group and that when both R.sup.1 and R.sup.2 are hydrogen atoms X.sup.1 is not acetyl group or .gamma.-glutamyl group, and salts thereof, show excellent hypotensive action, antiarrhythmic action, anti-anginal action, cardiotonic action or coronary vasodilation, thus being useful as therapeutic or prophylactic agents for the cardiovascular diseases such as hypertension and angina pectoris.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: May 26, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Giichi Goto, Shigenori Ohkawa, Shoji Fukumoto
  • Patent number: 5104883
    Abstract: Thioformamide derivatives of the formula: ##STR1## wherein: R represents alkyl; A represents an optionally substituted phenyl or heteroaromatic group; R.sup.1 represents hydrogen, alkyl, cyano, carboxyl, formyl, carbamoyl, alkoxycarbonyl or a group --(CH.sub.2).sub.n OR.sup.2, --(CH.sup.2).sub.n SR.sup.2, --(CH.sub.2).sub.n N(R.sup.2).sub.2, --CH.dbd.CHR.sup.3, --CH.dbd.NOR.sup.4, --CONHR.sup.5, or --COR.sup.6 ; R.sup.2 represents hydrogen, alkyl, alkanoyl, aryl, aryl (CH.sub.2).sub.n -- or arylCO--, or, when attached to nitrogen, two R.sup.2 groups may together represent alkylene; R.sup.3 represents hydrogen; alkyl, alkanoyl, carboxyl, carbamoyl, cyano, aryl, arylCO--, aryl(CH.sub.2).sub.n --, or aryl (CH.sub.2).sub.n CO--; R.sup.4 represents hydrogen, alkyl, aryl, aryl (CH.sub.2).sub.n -, optionally substituted alkyl, alkenyl, amino or carbamoyl N,N-disubstituted by alkylene; R.sup.5 represents alkyl, aryl, or aryl (CH.sub.2).sub.n -- or an amino acid residue; R.sup.6 represents alkyl, aryl, or aryl (CH.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: April 14, 1992
    Assignee: May & Baker Limited
    Inventors: Malcolm N. Palfreyman, Nigel Vicker, Roger J. A. Walsh
  • Patent number: 5084467
    Abstract: Insecticidally active nitro compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, cyano or alkyl,R.sup.2 is hydrogen or an organic radical,R.sup.3 is --O--R.sup.4, --S--R.sup.4 or ##STR2## R.sup.4 is an organic radical, R.sup.5 and R.sup.6 are hydrogen or organic radicals,Y is CH or N, andZ is an optionally substituted 5- or 6-membered heterocyclic group,with certain conditions and exceptions.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: January 28, 1992
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Koichi Moriya, Yumi Hattori, Ikuro Honda, Katsuhiko Shibuya
  • Patent number: 5079361
    Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5077423
    Abstract: S-(N-alkoxycarbonyl, N-substituted)amino methyl isothiourea derivative, which is a useful intermediate for the production of 1,3,5-thiadiazine-4-one derivative, is disclosed. The above compound can be produced by reacting the carbamate compound of the formula(II) with the thiourea compound of the formula(III).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: December 31, 1991
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Dae-Whang Kim, Sung-Yeap Hong, Jae-Wook Ryu, Jae-Chun Woo
  • Patent number: 5064843
    Abstract: This invention relates to a thioformamide derivative of the formula I ##STR1## wherein: R and R.sup.1 each independently represent an alkyl group;A represents either:(1) a phenyl group which is optionally substituted; or(2) a heteroaromatic group (e.g. pyrid-3-yl, quinolin-3-yl); andY represents:an ethylene or methylene group or a direct bond.These compounds may be formulated as pharmaceutical preparations and have utility for the treatment of disorders associated with smooth muscle contraction.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: November 12, 1991
    Assignee: Rhone-Poulenc Sante
    Inventors: Terance W. Hart, Bernard Y. J. Vacher, Brian W. Sharp
  • Patent number: 5055582
    Abstract: This invention relates to a process for preparing useful thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)thioxomethyl]hydrazono]ethyl]-1.alpha. ,4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha.,7a.alpha.-4.alpha.,7.alpha.-meth ano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: October 8, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 5051434
    Abstract: Insecticidal novel nitro compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are hydrogen or C.sub.1-4 alkyl, R.sup.3 is --S--R.sup.4 or ##STR2## in which R.sup.4 is C.sub.1-4 alkyl, R.sup.5 and R.sup.6 are hydrogen or C.sub.1-4 alkyl,Y is CH or N, andZ is a five- or six-membered heterocyclic group having at least one nitrogen atom which may be substituted by halogen or C.sub.1-4 alkyl, provided that where Y is CH,then R.sup.1 is C.sub.1-4 alkyl.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: September 24, 1991
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Shiokawa Kozo, Shinichi Tsuboi, Koichi Moriya, Yumi Hattori, Ikuro Honda, Katsuhiko Shibuya
  • Patent number: 5021437
    Abstract: The present invention relates to a novel ribonucleotide reductase inhibitor and new combinations comprising an antiviral compound, such as acyclovir, and a thiocarbonohydrazone ribonucleotide reductase inhibitor for the chemotherapeutic treatment of virus infections, especially viruses of the herpes group.
    Type: Grant
    Filed: June 26, 1989
    Date of Patent: June 4, 1991
    Assignee: Burroughs Wellcome Co.
    Inventor: Todd A. Blumenkopf
  • Patent number: 5004743
    Abstract: Compounds having the formula: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.
    Type: Grant
    Filed: November 25, 1987
    Date of Patent: April 2, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Robert Zamboni, Jacques Y. Gauthier
  • Patent number: 5001156
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: March 19, 1991
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 4994612
    Abstract: Dihydropyridine derivatives of the formula ##STR1## wherein the symbols R and R.sup.1 to R.sup.6 have the significance given in claim 1, have a pronounced calcium-antagonist activity and can accordingly be used as medicaments, especially in the control or prevention of angina pectoris, ischemia, high blood pressure and/or migraine.
    Type: Grant
    Filed: April 11, 1989
    Date of Patent: February 19, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Roland Jaunin, Henri Ramuz
  • Patent number: 4987130
    Abstract: Substituted amino derivatives represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 each stand for an acyclic hydrocarbon residue or an alicyclic hydrocarbon residue; R.sup.3 and R.sup.4 each stand for hydrogen or a hydrocarbon residue optionally containing hetero-atom(s); A stands for a carbon chain having two or more carbon atoms optionally containing ether linkage or sulfide linkage, which may be substituted and which may per se form a ring; X.sup.1 and X.sup.2 each stand for oxygen atom or sulfur atom; and Y stands for amino group or an organic residue bonded through nitrogen atom, which may form a ring by combining with a carbon atom constituting A; and their salts have anti-arrhythmic activity and are useful for prevention and treatment of a variety of arrhythmias.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: January 22, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Susumu Tsushima, Muneo Takatani, Minoru Hirata
  • Patent number: 4971986
    Abstract: Compounds of formula I ##STR1## wherein A, X.sub.1, X.sub.2, X.sub.3, X.sub.4, Y, Z and R.sub.1 to R.sub.6 have the meanings given in the description, have valuable pharmaceutical properties and are effective especially against tumors. They are prepared in a manner known per se.
    Type: Grant
    Filed: March 15, 1989
    Date of Patent: November 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jaroslav Stanek, Giorgio Caravatti, Jorg Frei, Hans-Georg Capraro
  • Patent number: 4960897
    Abstract: Disclosed herein is an N-[2-(pyridyl)propyl]-N-substituted sulfonamide represented by the following general formula (I): ##STR1## wherein J represents a phenyl group which may be substituted or benzo-condensed, A represents --CH.sub.2 --, --CH.dbd.CH--, --O-- or --N(r)-- (wherein r represents an alkyl group having 1 to 4 carbon atoms), b represents 0 or 1, R represents an alkyl group, alkenyl group, alkynyl group, alkoxy group, fluoroalkyl group or formyl group, D represents a hydroxyl group, E represents a halogen atom, an alkylsulfonyloxy group or a benzenesulfonyloxy group which may be substituted, or D and E represent --O-- in combination, and V represents a pyridyl group which may be substituted, a herbicide containing said N-[2-(pyridyl)propyl]-N-substituted sulfonamide as an active ingredient and a 1-(halogenomethyl)vinylpyridine as an intermediate thereof.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: October 2, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Manabu Katsurada, Toyohiko Shike, Emiko Mikami, Osamu Ikeda
  • Patent number: 4927838
    Abstract: The invention relates to compounds of the formula ##STR1## wherein Y and Y' are hydrogen or taken together are O or S, *A is paraphenylene or *----(CH.sub.2).sub.n --(X).sub.s --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, m is an integer from 0 to 1, s is an integer from 0 to 1, provided that when s is 1, n+m must be at least 2, t is an integer from 0 to 10, R.sub.1 and R.sub.2, independently, are lower alkyl, lower alkenyl or aryl, or one of R.sub.1 or R.sub.2 is hydrogen and the other is ##STR2## wherein W is ##STR3## --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --, O, S, or ##STR4## and X.sub.1 is lower alkyl, phenyl unsubstituted or mono-, di- or trisubstituted by lower alkoxy, lower alkyl or halogen, and X.sub.2, X.sub.3 and X.sub.4, independently, are hydrogen, lower alkyl, lower alkoxy or halogen, R.sub.3 is hydrogen, lower alkyl or aryl, R.sub.4 is hydrogen, lower alkyl, aryl, aryl-lower alkyl or acyl, R.sub.5 is hydrogen or lower alkyl,R.sub.
    Type: Grant
    Filed: July 5, 1988
    Date of Patent: May 22, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, John G. Mullin, Jefferson W. Tilley
  • Patent number: 4916145
    Abstract: The invention relates to compounds of the formula ##STR1## wherein *B is ##STR2## Y is O or S, *A is *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, n or r, independently, are integers from 0 to 3, m is an integer from 0 to 1, provided that when m is 1, then n must be at least 1, X is O or S, R.sub.1 and R.sub.4, independently, are hydrogen, lower alkyl, hydroxy or lower alkoxy, provided that when *B is other than ##STR3## at least one of R.sub.1 and R.sub.4, and one of R.sub.6 and R.sub.7 must be hydrogen, R.sub.2 and R.sub.3 are independently hydrogen, lower alkyl, cycloalkyl, halogen, nitro, lower alkoxy, lower alkenyl, lower alkynyl or aryl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: April 10, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jefferson W. Tilley, Robert W. Guthrie, John W. Clader, Ronald A. LeMahieu
  • Patent number: 4898455
    Abstract: There is described compounds of the formula ##STR1## wherein X stands for CH and Y stands for N or X stands for N and Y stands for CH; A.sup.1 and A.sup.2 signify single covalent bonds or one of the groups A.sup.1 and A.sub.2 also signifies trans-1,4-cyclohexylene, cis-4-cyano-trans-1,4-cyclohexylene or 1,4-phenylene optionally substituted with halogen or methyl; ring B represents trans-1,4-cyclohexylene, 1,4-phenylene optionally substituted with halogen or methyl or, when A.sup.2 signifies a single covalent bond, also cis-4-cyano-trans-1,4-cyclohexylene; R.sup.1 denotes an optionally halogen-substituted alkyl or alkenyl group in which optionally one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are replaced by --O--, --COO-- and/or --OOC--; R.sup.2 signifies an optionally halogen-substituted alkyl or alkenyl group in which optionally one CH.sub.2 group or two non-adjacent CH.sub.2 groups is/are replaced by --O--, --COO-- and/or --OOC-- or R.sup.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: February 6, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Buchecker, Alfred Germann, Stephen Kelly, Martin Schadt
  • Patent number: 4897485
    Abstract: Pyrid-3-yl-2,3-diazabutadiene-1-yl]-disulfides of formula ##STR1## wherein B is unsubstituted or substituted C.sub.1 -C.sub.6 alkyl, phenyl or substituted phenyl, or is the radical ##STR2## and Y is an unsubstitued or a substituted aromatic carbocycle or heterocycle,and the salts and optical isomers thereof, processes for the preparation of these compounds and compositions containing them for use in pest control, especially for controlling insects that attack plants and animals. The compounds are particularly effective against plant-destructive sucking insects.
    Type: Grant
    Filed: March 11, 1988
    Date of Patent: January 30, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Saleem Farooq
  • 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: 4859689
    Abstract: There is disclosed a fungicidal composition comprising (A) a fungicidal compound selected from the group consisting of (i) benzimidazole compounds of the formula ##STR1## wherein W is H, or alkyl carbamoyl; Y is thiazolyl, dihydrothiazolyl, tetrahydrothiazolyl or furyl; Z is H, halogen or alkyl and (ii) benzimidazole related compounds of the formula ##STR2## wherein R.sub.3 is C.sub.1-2 alkyl, and Z is as defined above, and (B) a synergist alkyl pyridinium salt of the formula ##STR3## wherein R is an alkyl containing 8 to 20 carbon atoms; and X is a monovalent anion.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: August 22, 1989
    Assignee: Safer, Inc.
    Inventors: George S. Puritch, Edward S. Kondo
  • Patent number: 4855213
    Abstract: Polymethine dyes are disclosed containing an acidic electron accepting terminal nucleus comprised of an isocyano group. The dyes are useful as spectral sensitizers in ultravioilet responsive imaging compositions.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: August 8, 1989
    Assignee: Eastman Kodak Company
    Inventor: Margaret E. Logan
  • Patent number: 4845219
    Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: July 4, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
  • Patent number: 4843083
    Abstract: A 2-pyridylacetic acid derivative having the formula (I): ##STR1## wherein R.sup.1 represents an alkyl having 5 to 10 carbon atom or --(CH.sub.2).sub.m --cycloalkyl group having C.sub.5 -C.sub.8 cycloalkyl, which may be substituted with at least one alkyl group having 1 to 6 carbon atoms, where m represents zero or an integer of 1 to 4; R.sup.2 represents hydrogen, a linear alkyl, a hydroxyalkyl group, an alkenyl, an aryl, an aralkyl or a group--(CH.sub.2)--A, where n represents an integer of 0 to 3 and A represents a nitrogen-containing heterocyclic group which may be replaced by an alkyl having 1 to 10 carbon atoms or an aralkyl having 7 to 10 carbon atoms and a pharmacologically acceptable acid addition salt thereof, which has the effects of both an inhibition of gastric acid and a protection of gastric mucosa, and which has a low toxicity.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: June 27, 1989
    Assignee: Suntory Limited
    Inventor: Mitsuhito Okitsu
  • Patent number: 4833252
    Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings:R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: May 23, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Topfl, Georg Pissiotas
  • Patent number: 4810796
    Abstract: Pyridinol carbamate is prepared by a process in which a carbamate of the formulaH.sub.3 C--NH--CO--O--Rwhere R is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert.-butyl, is reacted with 2,6-bis-(hydroxymethyl)-pyridine in the presence of a transesterification catalyst of the Lewis acid type in the liquid phase at elevated temperatures.
    Type: Grant
    Filed: February 13, 1987
    Date of Patent: March 7, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Michael Luksza
  • Patent number: 4806553
    Abstract: There are provided insecticidally active alkylenediamines of the formula ##STR1## wherein W.sup.1 stands for a 5- or 6-membered heterocyclic group which may be substituted, containing at least one hetero atom selected from, O, S and N, R.sup.1, R.sup.2 and R.sup.3 are hydrogen or alkyl and R.sup.4, X, Y and Z have the meanings as given in the specification.The new alkylenediamines can be prepared according to different preparation methods and exhibit a strong insecticidal activity.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: February 21, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
  • Patent number: 4788206
    Abstract: Compounds of the formula ##STR1## Y is O ir S, *A is paraphenylene or *----(CH.sub.2)n----(X).sub.m --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment,and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 29, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4786646
    Abstract: The invention relates to compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is ##STR2## or --(CH.sub.2).sub.k -- wherein k is an integer from 0 to 4, R.sub.3, R.sub.4 and R.sub.8 are independently hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 22, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4766136
    Abstract: Novel fungicidally active phenylsulphonyl-pyridine aldoximes of the formula ##STR1## in which R.sup.1 represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, nitro, alkoxycarbonyl or alkylcarbonylamino,R.sup.2 represents halogen or alkyl,n represents an integer 0, 1, 2, 3, 4 or 5, andm represents an integer 0, 1, 2, 3 or 4.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: August 23, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christa Fest, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4766132
    Abstract: Compounds of formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is unsubstituted or substituted aryl or heteroaryl; R.sup.2 is H, alkyl, alkenyl or alkynyl; X is O, NH, or S; R.sup.3 being alkyl, alkenyl, alkynyl or COR.sup.4 where R.sup.4 has an R.sup.3 value, when X is O; R.sup.3 being --CO-- alkyl when X is NH; and R.sup.3 being alkyl, alkenyl or CSNR.sup.5 R.sup.6 where R.sup.5 and R.sup.6, which may be the same or different, are H, alkyl, alkenyl or, together with the adjacent N atom, constitute a ring, when X is S; or XR.sup.3 together represent --CN; and salts and metal complexes thereof, have fungicidal and plant growth regulating activity.
    Type: Grant
    Filed: January 29, 1986
    Date of Patent: August 23, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Ian T. Kay
  • Patent number: 4742070
    Abstract: Arylsulphonyl-pyridinealdoxime derivatives of the formula (I) ##STR1## in which R, R.sup.1, R.sup.2, n and m have the meanings stated in the description, and their use as agents for combating pests.The new arysulphonyl-pyridinealdoxime derivatives of the formula (I) can be prepared from suitable arylsulphonyl-pyridinealdoximes and suitable carbonyl compounds.
    Type: Grant
    Filed: March 12, 1987
    Date of Patent: May 3, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christa Fest, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke