The Ether Oxygen Is Bonded Directly To The Aryl Ring Or Ring System Patents (Class 564/347)
  • Patent number: 4994616
    Abstract: A novel herbicide of formula I ##STR1## wherein R.sub.1 represents a halogen atom or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;R.sub.2 represents a hydrogen or halogen atom;each of R.sub.3 to R.sub.6 independently represents a hydrogen or halogen atom or a cyano, alkyl, haloalkyl, alkoxy or haloalkoxy group;R.sub.7 represents a hydrogen or halogen atom, or an alkyl, haloalkoxy, haloalkyl or alkoxycarbonyl group;and A represents a nitrogen atom or a --CH-- group, together with its formulation and use as a herbicide, and its preparation.
    Type: Grant
    Filed: April 12, 1988
    Date of Patent: February 19, 1991
    Assignee: Ube Industries, Ltd.
    Inventor: David Munro
  • Patent number: 4956388
    Abstract: The present invention provides 3-aryloxy-3-substituted propanamines capable of inhibiting the uptake of serotonin and norepinephrine.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: September 11, 1990
    Assignee: Eli Lilly and Company
    Inventors: David W. Robertson, David T. Wong, Joseph H. Krushinski, Jr.
  • Patent number: 4892671
    Abstract: New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) ##STR1## or a derivative thereof in which R.sup.1, R.sup.2 and R.sup.3 are, independently, hydrogen, a C.sub.1 -C.sub.15 straight or branched chain alkyl residue, a C.sub.5 -C.sub.12 cycloalkyl residue, a C.sub.6 -C.sub.15 aryl residue or C.sub.7 -C.sub.12 alkaryl residue, and R.sup.4 and R.sup.5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that(a) R.sup.4 and R.sup.5 are not simultaneously hydrogen,(b) when R.sup.4 and R.sup.5 are each --CH.sub.2 --CH.sub.2 --OH, R.sup.1 and R.sup.2 are not simultaneously hydrogen and R.sup.3 is not a pentyl residue and(c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent;as well as salts thereof.Some of the compounds of formula I are new.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: January 9, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert M. O'Neil, John D. Payne
  • Patent number: 4880841
    Abstract: Phenethylamine derivatives shown by the general formula ##STR1## wherein Ro represents a lower alkyl group; R.sub.1 represents a lower alkyl group or a lower alkoxy group; R.sub.2 represents hydrogen atom or a hydroxyl group; R.sub.3 and R.sub.4 each represents hydrogen atom or a lower alkyl group; R.sub.5 represents hydrogen atom or a lower alkoxy group; X represents oxygen atom or a methylene group; m is an integer of 1 -3; and n is an integer of 0-2 and the acid addition salts thereof.These compounds exhibit a strong .alpha.-adreneregic blocking action and are useful as an antihypertensive agent.
    Type: Grant
    Filed: February 3, 1989
    Date of Patent: November 14, 1989
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Imai, Kunihiro Niigata, Takashi Fujikura, Shinichi Hashimoto, Toichi Takenaka, Kazuo Honda
  • Patent number: 4867888
    Abstract: A series of water-soluble, or at least water-dispersible, corrosion inhibiting solutions are disclosed which contain about 2 ppm to about 70%, preferably about 3 ppm to about 200 ppm, of an ethoxylated, propoxylated alkylphenol amine represented by the formula: ##STR1## wherein R is hydrogen or an alkyl group containing about 5 to about 12 carbon atoms, R' is an alkyl group containing about 5 to about 12 carbon atoms, x equals about 1 to about 20, z equals about 1 to about 20, a equals about 1 to about 20, and b equals about 1 to about 20. The salt reaction products of the instant alkoxylated amine and an organic acid selected from the group consisting of hydroxyacetic acid, a fatty acid, a dicarboxylic acid, a dimer-trimer acid, an acidic phosphorus containing compound, and mixtures thereof are also effective in controlling sour and sweet corrosion.
    Type: Grant
    Filed: December 24, 1987
    Date of Patent: September 19, 1989
    Assignee: Texaco Inc.
    Inventor: Frederick W. Valone
  • Patent number: 4864061
    Abstract: New substituted phenoxyalkanolamines and phenoxyalkanol-cycloalkylamines of the general formula I ##STR1## in which R.sup.1 and R.sup.2, which can be identical or different, denote alkyl groups with in each case 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together denote the group --(CH.sub.2).sub.n --, wherein n is the number 4 or 5, R.sup.3 denotes hydrogen, or an alkyl group or an acyl group with in each case 1 to 6 carbon atoms, R.sub.4 denotes an alkyl group with 1 to 4 carbon atoms or the cyclopropylmethyl group and R.sup.5 denotes hydrogen halogen or alkyl, and acid addition salts thereof, have a cardioselective .beta..sub.1 -adrenolytic and hypotensive action. They can be used as medicaments for the treatment of angina pectoris, hypertension and arrhythmias.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: September 5, 1989
    Assignee: Beiersdorf Aktiengesellschaft
    Inventor: Erich Cohnen
  • Patent number: 4853408
    Abstract: Novel 4-phenylpropyl-indoles of the formula ##STR1## wherein R and R.sub.1 are individually selected from the group consisting of hydrogen, linear alkyl of 1 to 5 carbon atoms, branched alkyl of 3 to 5 carbon atoms, cycloalkyl of 3 to 7 carbon atoms cycloalkylalkyl of 4 to 7 carbon atoms and optionally substituted aralkyl of 7 to 12 carbon atoms or R.sub.1 and R taken together with the nitrogen atom form an optionally unsaturated heterocycle containing another heteroatom selected from the group consisting of oxygen, sulfur and nitrogen optionally substituted with a member of the group consisting of alkyl of 1 to 5 carbon atoms, phenyl, naphthyl and aralkyl of 7 to 12 carbon atoms, a together with b forms .dbd.0 or a together with c form a carbon-carbon bond, b is hydrogen or with a forms .dbd.0, c is hydrogen or with a forms a carbon-carbon bond, the dotted line is an optional carbon-carbon bond, A is --(CH.sub.2).sub.n --, is an integer from 2 to 5, R.sub.
    Type: Grant
    Filed: April 17, 1986
    Date of Patent: August 1, 1989
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Jacques Guillaume, Gilles Hamon
  • Patent number: 4849530
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: July 18, 1989
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Gerhard Zol, Gerhard Pfarrhofer
  • Patent number: 4846980
    Abstract: A series of oil soluble to water-dispersible, corrosion inhibiting solutions are disclosed which contain about 2 ppm to about 70%, preferably about 3 ppm to about 200 ppm, of an ethoxylated, propoxylated dialkylphenol amine represented by the formula: ##STR1## wherein R and R' are alkyl groups containing about 5 to about 12 carbon atoms, x equals about 1 to about 10, and z equals about 2 to about 20. The salt and amide reaction products of the instant alkoxylated amine and an organic acid selected from the group consisting of hydroxyacetic acid, a fatty acid, a dicarboxylic acid, a dimer-trimer acid, an acidic phosphorus containing compound, and mixtures thereof are also effective in controlling sour and sweet corrosion. A method is also disclosed for protecting metal from corrosion by contacting the metal with an effective amount of the amine, or the amine/acid or amide reaction products, in a continuous or batch treatment.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: July 11, 1989
    Assignee: Texaco Inc.
    Inventor: Frederick W. Valone
  • Patent number: 4825000
    Abstract: A series of polyoxyalkylene diamines modified with phenoxy groups is disclosed. This series of diamines is of the general formula: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen or an alkyl of 1 to 4 carbon atoms, R.sub.3 is a alkyl of 1 to 4 carbon atoms, Ph is phenyl, x ranges from 2 to 40, y ranges from 1 to 20 and z ranges from 1 to 40.These diamines are cured with liquid epoxy resins. The cured resins demonstrated improved tensile strength and modulus, elongation and flexural strength and modulus over a commercially used curative.The diamines are also useful in RIM elastomers, in polyamides and as chain extenders in polyurethane foams.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: April 25, 1989
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Robert L. Zimmerman, Michael Cuscurida, Harold G. Waddill
  • Patent number: 4814507
    Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylkene; Y is -(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4803225
    Abstract: There are provided compounds of formula I, ##STR1## and pharmaceutically acceptable derivatives thereof. There are also described the use of the compounds of formula I as pharmaceuticals, methods for making the compounds and pharmaceutical, e.g. cardiac, compositions containing the compounds.
    Type: Grant
    Filed: December 2, 1987
    Date of Patent: February 7, 1989
    Assignee: Fisons, plc
    Inventors: John Dixon, Francis Ince
  • Patent number: 4792570
    Abstract: Compounds useful for treating inflammation, swelling and associated pain, represented by the formula: ##STR1## and the pharmaceutically acceptable acid addition salts thereof, wherein: a is an integer of 0-3;b is an integer of 0-2;n is an integer of 3-12;each X and each Y are independently -halo, --R.sup.1, -alkoxy, or -phenyl; andB is selected from the group consisting of:--NR.sup.1 R.sup.2, --NR.sup.1 (CH.sub.2 CH.sub.2 OH), ##STR2## in which R.sup.1 and R.sup.2 are independently H, alkyl or cycloalkyl;R.sup.3 is H, alkyl or --CH.sub.2 CH.sub.2 OH; andm is an integer of 3-8.Novel compounds are those wherein n is at least 6 if both a and b are 0.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: December 20, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, James P. Dunn, Stefan H. Unger, Thomas R. Thieme
  • Patent number: 4767784
    Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: November 28, 1986
    Date of Patent: August 30, 1988
    Inventors: Gerhard Zolss, Gerhard Pfarrhofer
  • Patent number: 4743703
    Abstract: The 4-fluoroalkyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: May 10, 1988
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4734500
    Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylene; Y is --(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: March 11, 1986
    Date of Patent: March 29, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4725683
    Abstract: Novel intermediates useful in the preparation of fluorophenoxyphenoxypropionates and derivatives thereof which possess herbicidal activity selectively in the presence of broadleaf crops.
    Type: Grant
    Filed: August 12, 1985
    Date of Patent: February 16, 1988
    Assignee: The Dow Chemical Company
    Inventors: Richard B. Rogers, B. Clifford Gerwick, III
  • Patent number: 4720586
    Abstract: There are provided compounds of formula I, ##STR1## in which R.sub.1 represents OH,R.sub.2 and R.sub.3, which may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, alkyl C1 to 6, nitro, nitrile, (CH.sub.2).sub.p R.sub.9 or SR.sub.9,W represents a single bond, a 1,2; 1,3; or 1,4-disubstituted benzene ring; a --CH.dbd.CH--group or a 1,4-cyclohexanediyl group;X respresents NH, O, S, SO.sub.2, CO, CH.sub.2, CONH or --COO;Y represents (CH.sub.2)q, CO, CS, SO.sub.2 and R.sub.20 represents hydrogen,or Y represents CR.sub.15 R.sub.16 CR.sub.17 R.sub.18,wherein the carbon atom bearing R.sub.15 and R.sub.16 is adjacent to X and in whichR.sub.15 and R.sub.18, together with the carbon atom to which they are attached form a carbonyl group, and R.sub.15, R.sub.16 and R.sub.20 each represent hydrogen, orR.sub.15 and R.sub.20 together form a chain --CH.sub.2 --, and R.sub.16, R.sub.17 and R.sub.18 each represent hydrogen, orR.sub.15, R.sub.16, R.sub.17 and R.sub.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: January 19, 1988
    Assignee: Fisons, plc
    Inventors: John Dixon, Francis Ince
  • Patent number: 4699928
    Abstract: Fluoroallylamine derivatives of the following Formula I are novel MAO-inhibitors and at low dose levels selectively inhibit MAO-B: ##STR1## wherein: R.sub.1 and R.sub.2 independently represent hydrogen, chlorine or fluroine;R.sub.3 represents hydrogen or (C.sub.1 -C.sub.4)alkyl; andX represents oxygen or sulfur.They are useful for the treatment of depression and, co-administered with L-dopa, in the treatment of Parkinsonism.
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: October 13, 1987
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventor: Ian A. McDonald
  • Patent number: 4659833
    Abstract: Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy)-2-p ropanol are now provided as new substances. These four optical isomers are now named as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, (2S, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4"-isocarbostyriloxy )-2-propanol, respectively. These four optical isomers have different activities for their .beta.-adrenergic-blocking effect and .alpha.-adrenergic-blocking effect and are useful as valuable agents for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds.
    Type: Grant
    Filed: May 8, 1985
    Date of Patent: April 21, 1987
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Toshihiro Takahashi, Noriyoshi Sueda, Masahiro Tsuji, Yoshiyuki Tahara, Hiroyasu Koyama, Yoshikuni Suzuki, Masao Nagase, Toshiji Sugai
  • 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: 4636256
    Abstract: A series of water-soluble, or at least water-dispersible, corrosion inhibiting solutions are disclosed which contain about 2 ppm to about 70%, preferably about 3 ppm to about 200 ppm, of an ethoxylated, propoxylated alkylphenol amine represented by the formula: ##STR1## wherein R is an alkyl group containing about 5 to about 12 carbon atoms, x equals about 3 to about 15, and z equals about 2 to about 10. The salt and amide reaction products of the instant alkoxylated amine and an organic acid selected from the group consisting of hydroxyacetic acid, a fatty acid, a dicarboxylic acid, a dimer-trimer acid, a phosphate ester and mixtures thereof are also effective in controlling sour and sweet corrosion. A method is also disclosed for protecting metal from corrosion by contacting the metal with an effective amount of the amine, or the amine/acid or amide reaction products, in a continuous treatment.
    Type: Grant
    Filed: July 2, 1985
    Date of Patent: January 13, 1987
    Assignee: Texaco Inc.
    Inventor: Frederick W. Valone
  • Patent number: 4626549
    Abstract: 3-Aryloxy-3-phenylpropylamines and acid addition salts thereof are useful in blocking uptake of monoamines by brain neurons, and are thus effective in treating disorders of sleep, sexual performance, appetite, muscular function, and pituitary function.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: December 2, 1986
    Assignee: Eli Lilly and Company
    Inventors: Bryan B. Molloy, Klaus K. Schmiegel
  • Patent number: 4609758
    Abstract: This invention provides a group of hydroxycycloalkanephenoxyethylamine antidepressant derivatives of the following structural formula: ##STR1## in which R.sub.1 is hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2 is alkyl of 1 to 6 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, hydroxyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 7 carbon atoms, halo or trifluoromethyl;R.sub.5 is hydrogen, alkyl of 1 to 6 carbon atoms or alkanoyl of 2 to 7 carbon atoms;and n is one of the integers 0, 1, 2 or 3;or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: September 2, 1986
    Assignee: American Home Products Corporation
    Inventor: George E. M. Husbands
  • Patent number: 4605773
    Abstract: Alkylamine polyether surface active agent compositions and methods for using are described. The instant compositions are low foaming, and pH sensitive and are generally of the structure: ##STR1## in which (a) R.sub.1 may be hydrogen or alkyl;if R.sub.1 is hydrogen then R.sub.2, R.sub.3 and R.sub.4 must be alkyl having a total number of carbon atoms falling in the range of 7 to 23;if R.sub.1 is alkyl, then R.sub.2, R.sub.3 and R.sub.4 may be alkyl or hydrogen, the total number of carbon atoms in R.sub.1 +R.sub.2 +R.sub.3 +R.sub.4 falling in the range of 7 to 36 (preferably about 10 to 20);(b) The --(C.sub.2 H.sub.4 O).sub.m --segment must be a poly(oxyethylene) homogeneous chain or "block" polymer (i.e., a homopolymer), m having an average value in the range of 1 to 15, preferably 5 to 13; and(c) Y is selected from the group consisting of:(1) homogeneous poly(oxypropylene) chain (PO) "block" polymer or residue (i.e., a homopolymer), of the structure--(C.sub.3 H.sub.6 O).sub.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: August 12, 1986
    Assignee: Diamond Shamrock Chemicals Company
    Inventors: James E. Maloney, James A. McDonell
  • Patent number: 4599419
    Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: July 8, 1986
    Assignee: Mitsubishi Chemical Industries, Inc.
    Inventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
  • Patent number: 4588746
    Abstract: Disclosed are e.g. certain novel 2-benzyl-3-(substituted)-phenoxypropylamines, their methods of synthesis and pharmaceutical compositions. Said compounds are useful as potent and centrally active serotonin uptake inhibitors for the treatment of psychotropic disorders, particularly depression.
    Type: Grant
    Filed: January 4, 1984
    Date of Patent: May 13, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Jeffrey W. H. Watthey
  • Patent number: 4588749
    Abstract: Compounds of formula (II): ##STR1## or a pharmaceutically acceptable salt thereof, in which X is an oxygen atom or a bond, R.sup.1 is a hydrogen, fluorine, chlorine or bromine atom or a trifluoromethyl or C.sub.1-4 alkyl group, each of R.sup.2 and R.sup.3 is a hydrogen atom or a C.sub.1-4 alkyl group, R.sup.4 is a C.sub.1-4 alkyl group, R.sup.5 is a hydrogen atom or a C.sub.1-4 alkyl group, and n is an integer of from 1 to 3; are useful as anti-obesity and/or anti-hyperglycaemic agents.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: May 13, 1986
    Assignee: Beecham Group p.l.c.
    Inventor: Michael J. Ferris
  • Patent number: 4584404
    Abstract: Selective biogenic amine uptake inhibitors, 3-substituted phenyloxy-3-phenylpropyldimethylamines.
    Type: Grant
    Filed: October 24, 1983
    Date of Patent: April 22, 1986
    Assignee: Eli Lilly and Company
    Inventors: Bryan B. Molloy, Klaus K. Schmiegel
  • Patent number: 4556677
    Abstract: The invention provides novel compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, benzyloxy, allyloxy, 2,3-epoxypropoxy, methoxymethoxy, ethoxymethoxy, or 2,3-dihydroxypropoxy or ##STR2## wherein one of R.sub.5 and R.sub.6 is hydrogen or R.sub.5 and R.sub.6 are alkyl groups of 1-4 carbon atoms which may be the same or different, or the --NR.sub.5 R.sub.6 group stands for a nitrogen containing 5 to 7 membered heterocyclic radical and m is 1 or 2; R.sub.2 is an alkyl of 1 to 4 carbon atoms or ##STR3## wherein R.sub.7 has the same meanings as R.sub.1 except that R.sub.7 and R.sub.1 cannot simultaneously be the same; R.sub.3 is an alkyl of 2 to 4 carbon atoms, cyclopentyl or hydroxy-cyclopentyl; R.sub.4 is hydrogen or hydroxy; and n is 0 to 3, provided that when R.sub.4 is hydrogen, then R.sub.2 and R.sub.
    Type: Grant
    Filed: October 26, 1982
    Date of Patent: December 3, 1985
    Assignee: Farmos Group Ltd.
    Inventors: Marja-Liisa Sodervall, Kauko O. A. Kurkela, Arto J. Karjalainen, Reijo J. Toivola, Lauri V. M. Kangas, Guillermo L. Blanco
  • Patent number: 4526893
    Abstract: Compounds of the structure ##STR1## wherein X, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are as herein defined, effective as .beta.-blockers and hypotensive agents, are described.
    Type: Grant
    Filed: December 16, 1983
    Date of Patent: July 2, 1985
    Assignee: Nisshin Flour Milling Co., Ltd.
    Inventors: Toshihiro Takahashi, Noriyoshi Sueda, Masahiro Tsuji, Yoshiyuki Tahara, Hiroyasu Koyama, Yoshikuni Suzuki, Masao Nagase, Toshiji Sugai
  • Patent number: 4501924
    Abstract: This invention relates to certain herbicidally active substituted diphenyl ether acetals or ketals, herbicidal compositions of the same and the use thereof for preemergence postemergence control of noxious plants, i.e., weeds.
    Type: Grant
    Filed: May 2, 1983
    Date of Patent: February 26, 1985
    Assignee: PPG Industries, Inc.
    Inventor: Dennis K. Krass
  • Patent number: 4485258
    Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: November 27, 1984
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
  • Patent number: 4448992
    Abstract: Addition products obtained by reaction of triethanolamine condensation products of the formula 1, ##STR1## wherein n is intended to denote a number from 1 to 3, with bisglycidyl ethers of the formula 2, ##STR2## wherein R.sup.1 can be identical or different and denote hydrogen, C.sub.1 -C.sub.4 -alkyl or halogen, in particular chlorine, A denotes a direct bond, a sulfonyl or cyclohexyl group or a group of the formula ##STR3## wherein R.sup.2 denotes hydrogen, methyl or phenyl and a denotes a whole number from 0 to 10, and their use as demulsifiers for oil-water emulsions, as lubricants and as paper auxiliaries.
    Type: Grant
    Filed: September 9, 1982
    Date of Patent: May 15, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Diery, Bernhard Mees
  • Patent number: 4408075
    Abstract: A process of preparing tris-(ether-amines) of the formula:N--[A--O--(B--O).sub.n --R].sub.3in which R represents a hydrocarbon radical, A and B represent alkanediyl radicals, and n is a whole number between zero and 4, by ammonolysis of an alkylene glycol mono-ether of the formula:HO--A--O--(B--O).sub.n --Rin the presence of 10 to 40 percent by weight of a hydrogenation-dehydrogenation catalyst, based on weight of said alkylene glycol monoether.The tris-(ether-amines) produced, such as tris-(3,6-dioxa-octyl)amine, tris-(3,6,9-trioxaundecyl)amine, tris-(3,6-dioxaheptyl)amine, and tris-(3,6-dioxadecyl)amine.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: October 4, 1983
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4401832
    Abstract: Disclosed herein are .alpha.-[(alkylamino)methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: August 30, 1983
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4364956
    Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or 5-tetrazolylaminocarbonyl, where R.sup.5 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is a group of the formulaR.sup.6 --(Z).sub.m --where m is O or 1, Z is O, S, SO, SO.sub.2 or CO, and R.sup.6 phenyl optionally substituted by one or more group selected from halogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkoxy, benzyloxy, hydroxy, nitro, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, amino and NHR.sup.7 where R.sup.7 is C.sub.2-6 acyl; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. These compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.
    Type: Grant
    Filed: September 17, 1981
    Date of Patent: December 21, 1982
    Assignee: Lilly Industries Limited
    Inventors: Barry P. Clark, William J. Ross, Alec Todd
  • Patent number: 4360375
    Abstract: A herbicidal composition which comprises a phenoxyphenoxy unsaturated derivative having the formula: ##STR1## wherein X represents a halogen atom or CF.sub.3 ; Y represents a hydrogen atom or a halogen atom; and Z represents --COOR, --COR", --COOH, --CH.sub.2 OH, or --CH.sub.2 OR"'.
    Type: Grant
    Filed: December 23, 1980
    Date of Patent: November 23, 1982
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4352760
    Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: October 5, 1982
    Assignee: The Upjohn Company
    Inventor: Kirk M. Maxey
  • Patent number: 4343745
    Abstract: The invention provides a process for solubilizing an organic or mineral salt in an organic solvent, said process comprising contacting an organic or mineral salt of the formula A.sup.- M.sup.+, wherein A.sup.- represents a mineral or organic anion and M.sup.+ represents a cation selected from the group consisting of the cation NH.sub.4.sup.+ and its derivatives and the cations derived from the metals of the groups I.sub.A, II.sub.A, III.sub.A, IV.sub.A, V.sub.A, VI.sub.A, VII.sub.A, VIII, I.sub.B, II.sub.B, III.sub.B, IV.sub.B and V.sub.B of the periodic table, with at least one sequestering agent which is soluble in said organic solvent, said sequestering agent having the formula:N[CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (I)wherein n is an integer from 0 to 10 inclusive; R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which can be the same or different, are each a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms; R.sub.
    Type: Grant
    Filed: February 29, 1980
    Date of Patent: August 10, 1982
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4341718
    Abstract: Disclosed herein are .alpha.-[(alkylamino)-methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: July 3, 1978
    Date of Patent: July 27, 1982
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4333730
    Abstract: Novel meta-phenylenediamines are provided for use as couplers with dye bases in hair dye compositions. These meta-phenylenediamines have the formula: ##STR1## in which n is 2, 3 or 4. Their acid addition salts may also be used.
    Type: Grant
    Filed: April 18, 1980
    Date of Patent: June 8, 1982
    Assignee: Societe Anonyme dite: L'Oreal
    Inventors: Andree Bugaut, Majdi M. Shahin, Jean-Jacques H. Vandenbossche, Gregoire Kalopissis
  • Patent number: 4317819
    Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.
    Type: Grant
    Filed: December 5, 1980
    Date of Patent: March 2, 1982
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
  • Patent number: 4313896
    Abstract: 3-Aryloxy-3-phenylpropylamines and acid addition salts thereof, useful as psychotropic agents, particularly as anti-depressants.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: February 2, 1982
    Assignee: Eli Lilly and Company
    Inventors: Bryan B. Molloy, Klaus K. Schmiegel
  • Patent number: 4314081
    Abstract: 3-Aryloxy-3-phenylpropylamines and acid additions salts thereof, useful as psychotropic agents, particularly as anti-depressants.
    Type: Grant
    Filed: January 10, 1974
    Date of Patent: February 2, 1982
    Assignee: Eli Lilly and Company
    Inventors: Bryan B. Molloy, Klaus K. Schmiegel
  • Patent number: 4313005
    Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: January 26, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Randall J. Daughenbaugh
  • Patent number: 4301163
    Abstract: Amino-ether oxides of formula: ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 and R.sub.3 which are the same or different are hydrogen or lower alkyl, R.sub.4 is a phenyl or phenoxy nucleus optionally monosubstituted to trisubstituted by substituents which are the same or different, halogen or lower alkoxy, R.sub.5 is a phenyl radical optionally monosubstituted to trisubstituted by substituents which are the same or different, halogen, lower alkyl, lower alkoxy or nitro, a pyridyl radical or a lower alkyl radical, n is equal to zero, 1 or 2 and p is an integer from 0 to 9, m and q are equal to zero or 1.Local and spasmolytic anaesthetics.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: November 17, 1981
    Assignee: Societe Industrielle de Produits de Synthese
    Inventors: Dieran R. Torossian, Claude P. Roux, Gilbert G. Aubard
  • Patent number: 4296126
    Abstract: Novel benzene-propanamines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, chlorine, fluorine and bromine, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.2 is alkyl of 1 to 5 carbon atoms, R.sub.3 is selected from the group consisting of hydrogen, chlorine, bromine, --CF.sub.3, methyl and methoxy when R.sub.4 is nitro and R.sub.3 is selected from the group consisting of amino and acetamido when R.sub.4 is hydrogen and their non-toxic, pharmaceutically acceptable acid addition salts having anorexigenic activity and inhibit serotonine uptake in vivo and in vitro and their preparation.
    Type: Grant
    Filed: February 22, 1979
    Date of Patent: October 20, 1981
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Daniel Frechet, Claude Dumont
  • Patent number: 4291060
    Abstract: Novel compounds derived from formylphenoxyacetic acid such as N,N-dihexadecyl-4-(aminomethyl)phenoxy acetamide and N,N-dihexacecyl-2-(4-(aminomethyl)phenoxy) ethylamine and their non-toxic acid addition salts are useful for combating viral infections in vertebrate animals.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: September 22, 1981
    Assignee: Pfizer Inc.
    Inventor: Allen R. Kraska
  • Patent number: 4277610
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: July 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy