Patents Represented by Attorney William G. Webb
  • Patent number: 4304911
    Abstract: 1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n -N.dbd.B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-.differential.(CH.sub.2).sub.n --N.dbd.]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine.
    Type: Grant
    Filed: November 19, 1980
    Date of Patent: December 8, 1981
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4296238
    Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: October 20, 1981
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 4288547
    Abstract: 2-Hydroxygentamicins B, B.sub.1 and A.sub.3 and 2-hydroxy antibiotics JI-20A and JI-20B are prepared as fermentation products by culturing a nutrient medium containing carbohydrates, a source of assimilable nitrogen, essential salts and D-streptamine with a mutant of Micromonospora purpurea, and isolating the said fermentation products from the nutrient medium; the fermentation products are acylated with an ester of an .omega.-(N-benzyloxycarbonyl)amino-.alpha.-hydroxy-lower-alkanoic acid, after first blocking the 6'- and/or 2'-amine group with an amine-protecting group, followed by catalytic hydrogenolysis of the benzyloxycarbonyl group and removal of the amine-protecting groups to prepare the 1-N-(.omega.-amino-.alpha.-hydroxy-lower-alkanoyl) derivatives.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: September 8, 1981
    Inventor: Haruo Yamamoto
  • Patent number: 4273713
    Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as anti-secretory and anti-ulcer agents are prepared by hydrolysis of thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.
    Type: Grant
    Filed: September 17, 1979
    Date of Patent: June 16, 1981
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4255579
    Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: March 10, 1981
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 4248784
    Abstract: 1-R.sub.1 -4-R.sub.4 -.alpha.,.alpha.,2,5-Tetramethylpyrrole-3-acetamides, useful as anti-secretory and anti-ulcer agents, are prepared by hydrolysis, in the presence of a dilute mineral acid, of a corresponding 1-R.sub.1 -4-R.sub.4 -.alpha.,.alpha.,2,5-tetramethylpyrrole-3-acetonitrile.
    Type: Grant
    Filed: February 25, 1977
    Date of Patent: February 3, 1981
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4239687
    Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as anti-secretory and anti-ulcer agents are prepared by hydrolysis of thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: December 16, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4239890
    Abstract: 1-R.sub.1 -2-Q-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -1,2,3,4,4a,5,10,10a-Octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2.2.2]oct-5-ene.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: December 16, 1980
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 4228286
    Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared either by heating, with formic acid in an organic solvent or with certain ammonium formates, certain lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-3-[CO(CH.sub.2).sub.n -(2- and 3-furyl)]-1,2,3,4,4 a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylates or by reaction of a lower-alkyl .beta.-[3-R.sub.1 -6-(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionate with 2 or 3-furylacetic acid in the presence of a strong base.
    Type: Grant
    Filed: August 30, 1979
    Date of Patent: October 14, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4220763
    Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as antisecretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.
    Type: Grant
    Filed: August 2, 1979
    Date of Patent: September 2, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4215137
    Abstract: Method for alleviating diseases in animals susceptible to treatment via stimulation of the cell-mediated immune system and compositions useful therefor.
    Type: Grant
    Filed: June 26, 1978
    Date of Patent: July 29, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Richard A. Dobson, John R. O'Connor
  • Patent number: 4208523
    Abstract: 3-R.sub.1 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -6(eq)-R.sub.4 -11(eq)-(CH.sub.2 CH.sub.2 CH.sub.2 R.sub.5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, generally useful as morphine-like analgesics and as narcotic antagonists, are prepared by reducing, under Wolff-Kishner reaction conditions, a corresponding 3-R.sub.1 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -6(eq)-R.sub.4 -11(eq)-(CH.sub.2 CH.sub.2 COR.sub.5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine and, if desired, cleaving a lower-alkoxy, methoxymethoxy or benzyloxy group to an hydroxy group.
    Type: Grant
    Filed: November 30, 1978
    Date of Patent: June 17, 1980
    Assignee: Sterling Drug Inc.
    Inventors: William F. Michne, Thomas R. Lewis
  • Patent number: 4202984
    Abstract: .beta.-[3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '"-11(ax)-R.sub.3 -1,2,3,4,5,6,-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionic acids, esters and amides, useful as analgesics and narcotic antagonists, are prepared by heating, with formic acid in an organic solvent or with certain ammonium formates, certain di-lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3,3-dicarbox ylates, to prepare the esters, hydrolysis of the latter to prepare the acids and conversion of the acids to a mixed anhydride and reaction of the latter with ammonia or an appropriate amine to form the amides.
    Type: Grant
    Filed: May 4, 1979
    Date of Patent: May 13, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4202983
    Abstract: 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 "'-11(ax)-R.sub.3 -11(eq)-[CH.sub.2 CH.sub.2 CO(CH.sub.2).sub.n -X-Alk]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics, are prepared by heating, with formic acid in an organic solvent or with certain ammonium formates, a lower-alkyl 1-R.sub.1 -3-[Alk-X-(CH.sub.2).sub.n -CO]-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 "'-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat e.
    Type: Grant
    Filed: March 26, 1979
    Date of Patent: May 13, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4196296
    Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxamide and 4-thiocarboxamide derivatives useful as anti-secretory and anti-ulcer agents are prepared by hydrolysis or thiohydrolysis of the corresponding 2,4,5,6-tetrahydrocyclopenta[c]pyrrole-4-carbonitriles or, in the case of the thiocarboxamides, by reaction of the 4-carboxamide with phosphorus pentasulfide.
    Type: Grant
    Filed: December 21, 1977
    Date of Patent: April 1, 1980
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4182895
    Abstract: 1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles, useful as anti-depressants and analgesics, are prepared by reduction with an alkali metal aluminum hydride of an .omega.[1-(3,4-diphenyl-1H-pyrazolyl)]-lower alkanamide; reduction with hydrogen in the presence of ammonia, methylamine, dimethylamine or diethylamine over a catalyst of a 1-(cyano-lower-alkyl)-3,4-diphenyl-1-H-pyrazole; reaction of a 1-(tosyloxy-lower-alkyl)-3,4-diphenyl-1H-pyrazole with a lower-alkylamine; reaction of 3,4-diphenylpyrazole with a halo-lower-alkylamine in the presence of an acid acceptor; or reductive alkylation with formaldehyde of a 1-(3-aminopropyl)-3,4-diphenyl-1H-pyrazole.
    Type: Grant
    Filed: July 14, 1978
    Date of Patent: January 8, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4180667
    Abstract: 6(eq)-R.sub.4 -1,2,3,4,5,6-Hexahydro-3-R.sub.1 -11(ax)-R.sub.3 -11(eq)-CH.sub.2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, and 1-R.sub.1 -2-Q-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -1,2,3,4,4a,5,10,10a-octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2.2.2]-oct-5-ene.
    Type: Grant
    Filed: February 13, 1978
    Date of Patent: December 25, 1979
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 4172835
    Abstract: 1-(Phenylamino)pyrrole, useful as a urinary antiseptic, hypotensive and hypoglycemic agent, is prepared by reaction of an N-benzoylphenylhydrazine or N-lower-alkanoylphenylhydrazine or a lower-alkanealdehyde N-benzoylphenylhydrazone or N-lower-alkanoylphenylhydrazone with a 2,5-di-lower-alkoxytetrahydrofuran followed by hydrolytic removal of the benzoyl or lower-alkanoyl group from the resulting N-benzoyl-1-(phenylamino)pyrrole or N-lower-alkanoyl-1-(phenylamino)pyrrole.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: October 30, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Robert E. Johnson
  • Patent number: 4171378
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.
    Type: Grant
    Filed: January 30, 1975
    Date of Patent: October 16, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4163015
    Abstract: 1-(Arylamino)pyrroles and 1-(arylimino)pyrroles, useful as antibacterial agents, are prepared by reaction of an arylhydrazine or arylhydrazone with a 2,5-di-lower-alkoxytetrahydrofuran or with an alkanedione; by reaction of a 1-arylaminopyrrole with an oxalyl dihalide followed by oxidative hydrolysis of the product; by condensation of a 1-aminopyrrole with a quinone; or by oxidation or reduction of a respective 1-(arylamino)pyrrole or 1-(arylimino)pyrrole.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: July 31, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Robert E. Johnson