Halogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/346)
  • Patent number: 4267183
    Abstract: The invention concerns the novel amine 1-(2-chlorobenzyl)-1,2,3,6-tetrahydropyridine of the formula: ##STR1## and its pharmaceutically acceptable acid-addition salts, which have useful properties in inhibiting the aggregation of blood platelets, and are of application in the treatment or propyhylaxis of thrombosis or occlusive vascular disease. The invention also provides pharmaceutical compositions of, and analogy processes for the manufacture of the amine of formula I, or a salt thereof.
    Type: Grant
    Filed: February 7, 1980
    Date of Patent: May 12, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventors: Malcolm Johnson, Stuart D. Mills, Paul J. Phillips
  • Patent number: 4260766
    Abstract: (Dichloromethyl) substituted pyridines are prepared from (trichloromethyl) substituted pyridines by the reaction thereof under reductive dechlorination conditions with metallic iron or a ferrous iron compound and an acid.
    Type: Grant
    Filed: December 4, 1979
    Date of Patent: April 7, 1981
    Assignee: The Dow Chemical Company
    Inventor: Leo R. Morris
  • Patent number: 4259337
    Abstract: Novel m-trifluoromethylphenyl-piperidines of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, branched or straight chain alkyl of 1 to 5 carbon atoms, alkenyl of 3 to 5 carbon atoms, alkynyl of 3 to 5 carbon atoms and phenyl alkyl of 1 to 3 alkyl carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having antidepressive, anorexigenic and antiparkinsonian activity and their preparation and novel intermediates formed therein.
    Type: Grant
    Filed: May 12, 1977
    Date of Patent: March 31, 1981
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Jacques Guillaume, Claude Dumont
  • Patent number: 4259496
    Abstract: Side-chain fluorination of 3-methylpyridine is carried out by reaction with hydrogen fluoride and chlorine in the liquid phase. The main products are 3-trifluoromethylpyridine, 3-chlorodifluoropyridine and 3-difluoromethylpyridine.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: March 31, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventor: Graham Whittaker
  • Patent number: 4246268
    Abstract: Novel compounds of the formula ##STR1## wherein n is an integer of from 2 to 5, R is hydrogen, alkyl, alkoxy, halogen or trifluoromethyl, R.sub.1 is hydrogen, alkyl, alkoxy or halogen, X is carbonyl, hydroxymethylene or methylene, and Z is carbonyl or hydroxymethylene and their pharmaceutically acceptable acid addition salts are useful as antipsychotic agents having a low potential for extrapyramidal side effects. The novel compounds are prepared from novel intermediates of formula ##STR2## or their salts wherein R and X have the meanings defined above.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: January 20, 1981
    Assignee: Richardson-Merrell Inc.
    Inventor: Albert A. Carr
  • Patent number: 4246263
    Abstract: A series of 4-(2-hydroxyethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable acid addition salts, having antiinflammatory and immunoregulatory activity are disclosed. Preferred compounds include 4-(2-hydroxyethylthiomethyl)pyridine itself, as well as 4-(2-hydroxyphenylthiomethyl)pyridine, 4-(2-hydroxy-1-propylthiomethyl)pyridine, 4-(3-hydroxy-2-butylthiomethyl)pyridine, 4-(2-hydroxyethylthiomethyl)pyrimidine, the acetate esters corresponding to the above compounds, and 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine.
    Type: Grant
    Filed: October 15, 1979
    Date of Patent: January 20, 1981
    Assignee: Pfizer Inc.
    Inventors: Joseph G. Lombardino, Charles A. Harbert
  • Patent number: 4241071
    Abstract: Novel azacycloalkanes, azacycloalkenes and derivatives thereof and methods of preparing same are described. These compounds are useful as antidepressants, anticonvulsants, tranquilizers and analgetics.
    Type: Grant
    Filed: January 25, 1979
    Date of Patent: December 23, 1980
    Assignee: American Hoechst Corporation
    Inventors: Lawrence L. Martin, Helen H. Ong, Vernon B. Anderson, Charles A. Crichlow
  • Patent number: 4239764
    Abstract: Compounds of the formula ##STR1## where Ar represents a radical selected from the group consisting of 2,6-dichlorophenyl, 2,5-dichlorophenyl, 2-chloro-6-methylphenyl, 2-chloro-4-methylphenyl, 2,6-dichloro-4-bromophenyl, 4-cyanophenyl, 2,5-dimethoxyphenyl, and 2-methyl-5-fluorophenyl, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
    Type: Grant
    Filed: July 16, 1979
    Date of Patent: December 16, 1980
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Helmut Stahle, Herbert Koppe, Werner Kummer, Wolfgang Hoefke
  • Patent number: 4225602
    Abstract: The invention concerns the novel amine 1-(2-chlorobenzyl)-1,2,3,6-tetrahydropyridine of the formula: ##STR1## and its pharmaceutically acceptable acid-addition salts, which have useful properties in inhibiting the aggregation of blood platelets, and are of application in the treatment or prophylaxis of thrombosis or occlusive vascular disease. The invention also provides pharmaceutical compositions of, and analogy processes for the manufacture of the amine of formula I, or a salt thereof.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: September 30, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventors: Malcolm Johnson, Stuart D. Mills, Paul J. Phillips
  • Patent number: 4221913
    Abstract: 2-(Chloromethyl)pyridine is prepared by the reaction of 2-methylpyridine-N-oxide with phosgene (carbonyl chloride) in the presence of a solvent and an acid acceptor.
    Type: Grant
    Filed: February 26, 1979
    Date of Patent: September 9, 1980
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, Mezzie L. Ash
  • Patent number: 4213989
    Abstract: Novel 3-phenyl-tetrahydropyridines of the formula ##STR1## wherein X is selected from the group consisting of hydrogen and chlorine and R is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, alkenyl and alkynyl of 3 to 5 carbon atoms and phenyl alkyl of 1 to 3 alkyl carbon atoms with the proviso that X is not hydrogen when R is benzyl and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anorexigenic properties and inhibition of serontine collection both in vivo and in vitro and their preparation and novel intermediates.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: July 22, 1980
    Assignee: Roussel Uclaf
    Inventors: Lucien Nedelec, Jacques Guillaume, Claude Dumont
  • Patent number: 4211873
    Abstract: Monochloromethylpyridines are produced by reacting 2- or 4-methylpyridine oxides with phosphoryl chloride in the presence of an organic base. One product, 2-chloromethylpyridine, is formed by reacting 2-picoline-N-oxide with phosphoryl chloride in the presence of triethylamine.
    Type: Grant
    Filed: July 25, 1978
    Date of Patent: July 8, 1980
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, Mezzie L. Ash
  • Patent number: 4172946
    Abstract: Fluoroalkyl pyridines are produced in high yields by causing pyridines to react with fluoroalkyl iodides in the atmosphere of ammonia gas.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: October 30, 1979
    Assignee: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventor: Yasuo Maki
  • Patent number: 4172203
    Abstract: Dichloromethylpyridine derivatives are prepared from hydrazino adducts of trichloromethylpyridine compounds by reacting said adducts with an aqueous alkaline solution in the presence of a refluxing carrier medium.
    Type: Grant
    Filed: August 14, 1978
    Date of Patent: October 23, 1979
    Assignee: The Dow Chemical Company
    Inventor: Robin R. Ison
  • Patent number: 4155909
    Abstract: The invention relates to 2-alkyl nicotinoids and improved methods for producing them.
    Type: Grant
    Filed: June 13, 1977
    Date of Patent: May 22, 1979
    Assignee: Philip Morris Incorporated
    Inventors: Edward B. Sanders, Henry V. Secor, Jeffrey I. Seeman
  • Patent number: 4154835
    Abstract: Novel substituted imidazo [1,2-a] pyridine compounds are disclosed which have a high degree of anthelmintic activity. The compounds are substituted with a carbamate and a halogenated alkene group. Processes for the preparation of such compounds are also disclosed as well as compositions which use the described compounds as active ingredients for the treatment of helminthiasis.
    Type: Grant
    Filed: October 12, 1977
    Date of Patent: May 15, 1979
    Assignee: Merck & Co., Inc.
    Inventor: Richard J. Bochis
  • Patent number: 4150233
    Abstract: This invention relates to a new water-soluble, tetraphenyl substituted pyridinium salt compound and to a novel process of producing it. This compound finds use as a selective analytical reagent for certain large anions of low charge density.
    Type: Grant
    Filed: May 16, 1977
    Date of Patent: April 17, 1979
    Inventor: Thomas C. Chadwick
  • Patent number: 4145362
    Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 20, 1979
    Assignee: S.A. P R B en Neerlandais PRB N.V.
    Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
  • Patent number: 4138488
    Abstract: Disclosed herein are substituted diphenylmethyl picolinic acids, pharmaceutically acceptable salts, amides and esters thereof. The compounds disclosed are useful as topical anti-acne agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: February 6, 1979
    Assignee: Schering Corporation
    Inventors: Margaret H. Sherlock, Heide Roebke