Patents Represented by Attorney William G. Webb
  • Patent number: 4162361
    Abstract: Apomorphine derivatives are prepared in improved yield by rearrangement of the corresponding morphine derivative in the presence of anhydrous orthophosphoric acid under a partial vacuum and hydrolysis of the resulting phosphate esters in an aqueous medium.
    Type: Grant
    Filed: May 18, 1978
    Date of Patent: July 24, 1979
    Assignee: Sterling Drug Inc.
    Inventors: Roman R. Lorenz, Edward D. Parady, William H. Thielking
  • Patent number: 4160862
    Abstract: 1-Acyl-3-(amino-lower-alkyl)indoles, useful as anti-inflammatory agents, are prepared either by acylation of a 3-(amino-lower-alkyl)indole; by Fisher indole synthesis from an N'-acylphenylhydrazine and an amino-lower-alkanone; by alkylation of an amine with a 1-acyl-3-(halo-lower-alkyl)indole; or by reductive alkylation of a 1-acyl-3-indole-lower-alkylcarboxaldehyde.
    Type: Grant
    Filed: February 4, 1974
    Date of Patent: July 10, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4153719
    Abstract: Beta-diketones substituted by an aryl-aliphatic group in which the aliphatic chain is interrupted by a cyclic group, and useful as anti-viral agents, are prepared by interacting the appropriate aryl-aliphatic halide with an alkali metal salt of a beta-diketone.
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: May 8, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Guy D. Diana
  • Patent number: 4148794
    Abstract: Lower-alkyl 1-R.sub.1 -3-R.sub.5 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 es, useful as intermediates for the preparation of 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 COR.sub.5 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared by acylation of an appropriate lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.C-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 or carboxylation of an appropriate 1-R.sub.1 -3-COR.sub.5 "-4.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.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: April 10, 1979
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4140854
    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: October 4, 1977
    Date of Patent: February 20, 1979
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4138405
    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: October 7, 1976
    Date of Patent: February 6, 1979
    Assignee: Sterling Drug Inc.
    Inventor: Robert E. Johnson
  • Patent number: 4126620
    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: February 25, 1977
    Date of Patent: November 21, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4126616
    Abstract: N-Propylnorapomorphine dialkanoate, dibenzoate and dicyclopropanecarboxylate esters and acid-addition salts thereof, having anti-parkinson activity, are prepared by reaction of N-propylnorapomorphine with a respective alkanoyl, benzoyl or cyclopropanecarbonyl halide or corresponding acid anhydride in the presence of an acid acceptor.
    Type: Grant
    Filed: December 13, 1976
    Date of Patent: November 21, 1978
    Assignee: William B. Hinshaw
    Inventors: William Banks Hinshaw, Jack Pearl
  • Patent number: 4119628
    Abstract: Lower-alkyl 1-R.sub.1 -3-R.sub.5 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-carboxyla tes, useful as intermediates for the preparation of 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-11(eq)--CH.sub.2 CH.sub.2 COR.sub.5 --2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared by acylation of an appropriate 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-carboxylat e or carboxylation of an appropriate 1-R.sub.1 -3-COR.sub.5 "-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.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: October 10, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4108680
    Abstract: A mixture of nitric acid and manganese dioxide is effective in removing calcium oxalate scale from metal surfaces.
    Type: Grant
    Filed: March 16, 1977
    Date of Patent: August 22, 1978
    Assignee: Sterling Drug Inc.
    Inventor: James W. Barr, Jr.
  • Patent number: 4105766
    Abstract: 4,5-Dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylic acids and esters and alkali metal salts thereof, useful as anti-inflammatory, anti-allergic and anti-parasitic agents, are prepared by reacting a 4- or 5-R.sub.3 -2-carboxyphenylhydrazine with a lower-alkyl ethoxymethylenecyanoacetate and, if desired, saponifying the ester group and if desired, N-alkylating the product by reaction with an R.sub.2 -halide in the presence of an acid-acceptor.
    Type: Grant
    Filed: August 19, 1977
    Date of Patent: August 8, 1978
    Assignee: Sterling Drug Inc.
    Inventor: E. John Alexander
  • Patent number: 4105764
    Abstract: 4,5-Dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxamides, useful as anti-secretory agents, are prepared by reaction of an appropriate 4-R.sub.2 -4,5-dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylic acid halide with an appropriate amine.
    Type: Grant
    Filed: August 19, 1977
    Date of Patent: August 8, 1978
    Assignee: Sterling Drug Inc.
    Inventor: E. John Alexander
  • Patent number: 4100164
    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-ethano- (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: November 12, 1976
    Date of Patent: July 11, 1978
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 4098797
    Abstract: 2,4,5,6-Tetrahydrocyclopenta[c]pyrrole-4-carboxyamide 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: July 9, 1976
    Date of Patent: July 4, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, Rudolf Oesterlin
  • Patent number: 4084051
    Abstract: 4,5-Dihalopyrrole-2-carboxamide derivatives, prepared by reaction of a corresponding 4,5-dihalopyrrole-2-carboxylic acid halide or a corresponding 4,5-dihalopyrrol-2-yl trihalomethyl ketone with an appropriate amine, useful as antibacterial and herbicidal agents.
    Type: Grant
    Filed: June 7, 1976
    Date of Patent: April 11, 1978
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4080380
    Abstract: 2-Naphthyl-lower-alkylamines, useful as anti-inflammatory agents, are prepared by reaction of a 2-naphthyl-lower-alkanoyl halide with an amine and reduction of the resulting 2-naphthyl-lower-alkanoylamine with a reagent effective to reduce an amide to an amine.
    Type: Grant
    Filed: January 16, 1976
    Date of Patent: March 21, 1978
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4069256
    Abstract: N-{3-[R.sub.1 -(phenyl)-C(=X)]-phenyl-lower-alkyl}amines having anti-inflammatory utility are prepared either by reduction of a 3-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkanoylamine; by benzoylating a phenyl-lower-alkylamine; by reaction of a 3-lithiophenyl-lower-alkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile or by transformations involving manipulations of a carbonyl or carbinol group.
    Type: Grant
    Filed: December 17, 1975
    Date of Patent: January 17, 1978
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4069337
    Abstract: 2-Substituted-indole-1-lower-alkanecarboxamides, prepared by amidation of the corresponding acid or ester; by hydrolysis or thiohydrolysis of the corresponding carbonitrile; by alkylation of a suitable indole with a halo-lower-alkanecarboxamide; or by hydrolysis of a 1-indolechlorosulfonylcarbamyl derivative, have anti-secretory and anti-ulcer activities.
    Type: Grant
    Filed: December 1, 1976
    Date of Patent: January 17, 1978
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4065471
    Abstract: N-(4-Amino-2-butynyl)imides are prepared from N-propargylimides, paraformaldehyde and the appropriate secondary amine. The compounds are useful as stimulants or depressants of the central nervous system.
    Type: Grant
    Filed: September 14, 1970
    Date of Patent: December 27, 1977
    Assignee: Sterling Drug Inc.
    Inventor: William B. Dickinson
  • Patent number: 4051147
    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: June 9, 1975
    Date of Patent: September 27, 1977
    Assignee: Sterling Drug Inc.
    Inventor: Robert E. Johnson