Patents Represented by Attorney John J. McDonnell
  • Patent number: 4100150
    Abstract: The present invention encompasses a method for stabilizing interferon during purification, concentration, packaging, filtering and storage comprising treating an interferon preparation with an effective stabilizing amount of reduced glutathione, thiodiglycol, thioethanolamine, thioalkanoic acid having 1-7 carbon atoms, monothioglycerol, dithiothreitol, thioctic acid, N-acetylcysteine, or N-acetyl-homo-cysteine, as a sulfur containing reducing agent for selectively retaining interferon thiols in the reduced state. The method of the present invention preserves the activity of interferon by selectively retaining interferon sulfhydryl (SH) functions in the reduced state without reducing interferon disulfide linkages (--S--S--) which are essential for activity, or by selectively blocking interferon sulfhydryl groups.
    Type: Grant
    Filed: December 9, 1976
    Date of Patent: July 11, 1978
    Assignee: G. D. Searle & Co.
    Inventor: Terence Cartwright
  • Patent number: 4087621
    Abstract: 7-{3-Hydroxy-2.beta.-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1.alpha.-yl}hept-5-cis-enoic acids, displaying valuable pharmacological properties, e.g., gastric anti-secretory, are produced by the reaction of 7-(3-oxygenated-5-oxocyclopent-1-en-1-yl)hept-5-cis-enoic acid or ester with the appropriate organometallic reagent.
    Type: Grant
    Filed: November 10, 1975
    Date of Patent: May 2, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4087447
    Abstract: The present invention encompasses novel intermediates of the formula: ##STR1## wherein R is phenyl, cyclohexyl or lower alkyl having 1-6 carbon atoms; R' is trialkylsilyl wherein the alkyls have 1-4 carbon atoms, tetrahydropyran-2-yl, or tetrahydrofuran-2-yl; and R" is lower alkyl having 1 to 3 carbon atoms. Compounds of the present invention are useful in synthesizing prostaglandin-like molecules which are active anti-secretory agents.
    Type: Grant
    Filed: February 22, 1977
    Date of Patent: May 2, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4086134
    Abstract: Vaccines affording protection against the diseases resulting from infection of cats with feline leukemia virus are produced from cells infected with that virus or from the virus alone.
    Type: Grant
    Filed: February 22, 1977
    Date of Patent: April 25, 1978
    Assignee: University of Glasgow
    Inventors: William Fleming Hoggan Jarrett, James Oswald Jarrett, Lindsay Joan Mackey
  • Patent number: 4086227
    Abstract: The present invention, comprehends a method for treating diarrhea comprising administering to an animal in need of anti-diarrheal treatment an effective anti-diarrheal amount of a compound of the formula ##STR1## and acid addition salts thereof wherein Y is alkylene containing 1-4 carbon atoms; R.sub.2 and R.sub.3 together with N is a heterocyclic ring system comprising azamonocyclic ring of the formula ##STR2## wherein Z is phenylhydroxymethylmethylene, phenylhydroxymethylene, phenylcarboxymethylene, phenylcarbalkoxymethylene or azabicycloalkyl or phenyl or hydroxyl substituted azabicycloalkyl containing 6-9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkyl or 4-azatricyclo[4.3.1.1.sup.3,8 ]undec-4-yl; Ar.sub.1 and Ar.sub.2 are phenyl, halo-substituted phenyl, (lower alkyl) substituted phenyl, pyridyl, thienyl or furyl, and Ar.sub.
    Type: Grant
    Filed: August 2, 1977
    Date of Patent: April 25, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Gilbert W. Adelstein, Esam Z. Dajani, Chung Hwai Yen
  • Patent number: 4086220
    Abstract: Fragments of secretin are disclosed herein. The compounds disclosed contain the amino acid fragments of secretin having the 1-15 amino acid sequence through those having the 1-19 amino acid sequence. Also disclosed are the above secretin fragments having a protecting group on the first amino acid. The compounds are useful as gastric antisecretory agents.
    Type: Grant
    Filed: August 9, 1976
    Date of Patent: April 25, 1978
    Assignee: G. D. Searle & Co.
    Inventor: James M. Schlatter
  • Patent number: 4086268
    Abstract: 8-Chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine is transformed by various microorganisms into compounds having useful pharmacological properties or useful as intermediates in the synthesis of various pharmaceutical compounds. Among the microorganisms useful for this purpose are Trichoderma lignorum NRRL 8138, Hormodendrum sp. NRRL 8133, Cladosporium lignicolum NRRL 8131, Hormodendrum cladosporioides NRRL 8132, Pullularia pullulans NRRL 8137, Penicillium sp. NRRL 8136, Mucor sp. NRRL 8135, Chaetomium sp. NRRL 8130, and Hormodendrum sp. NRRL 8134.
    Type: Grant
    Filed: September 20, 1976
    Date of Patent: April 25, 1978
    Assignee: G. D. Searle & Co.
    Inventors: James Jiu, Seth S. Mizuba
  • Patent number: 4076707
    Abstract: N-(hexamethyleniminoalkyl)-5H-dibenz[b,f]-azepine-5-carboxamides having anti-arrhythmic activity are described herein. The subject compounds can be prepared by reacting a 5H-dibenz[b,f]azepine-5-carbonyl chloride with the appropriate hexamethyleniminoalkylamine.
    Type: Grant
    Filed: May 24, 1976
    Date of Patent: February 28, 1978
    Assignee: G. D. Searle & Co.
    Inventor: Peter K. Yonan
  • Patent number: 4076717
    Abstract: The subject compounds are ester, thioester, amide, hydrazide and anhydride derivatives of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid. These compounds are prepared by reacting the aforementioned acid with the appropriate alcohol, thiol, amine, or the like in the presence of a suitable dehydrating agent, or by reacting the acid chloride derivative of the aforementioned acid with the appropriate alcohol, thiol, amine or the like. A further embodiment of this invention is N-oxide derivative of 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid. This N-oxide compound is prepared by peracid treatment of the mentioned acid. The instant compounds share various valuable pharmacological properties, including analgesic and especially potent antidiarrheal properties.
    Type: Grant
    Filed: July 22, 1974
    Date of Patent: February 28, 1978
    Assignee: G. D. Searle & Co.
    Inventor: Eunice M. Kreider
  • Patent number: 4075407
    Abstract: Heterocyclic phosphonium salts of the following compound ##STR1## wherein d is 1, 2 or 3; R is hydrogen or an alkyl containing 1-3 carbon atoms; R.sub.1, R.sub.2 and R.sub.3 is each an alkyl radical containing 1-6 carbon atoms, a cycloalkyl radical containing 5 or 6 carbon atoms, or ##STR2## wherein n is 0-4, and Y is hydrogen, halogen, alkyl containing 1-6 carbon atoms or alkoxy containing 1-6 carbon atoms; X.sup.- is a pharmacologically acceptable anion; and one of a and b is a double bond and the other is a single bond. The compounds display valuable pharmacological properties, and are particularly useful as analgesic agents.
    Type: Grant
    Filed: November 15, 1976
    Date of Patent: February 21, 1978
    Assignee: G. D. Searle & Co.
    Inventor: Richard A. Mueller
  • Patent number: 4073807
    Abstract: The present invention encompasses compounds of the formula ##STR1## AND THE PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS THEREOF WHEREIN R represents hydrogen or hydroxymethyl. The compounds of the present invention are prepared by condensing N-carbobenzyloxyserine or 2-carbobenzyloxyamino-3-hydroxy-2-hydroxymethylpropionic acid with p- N,N-bis(2-chloroethyl)!phenylenediamine hydrochloride and removing the carbobenzyloxy protecting group by catalytic hydrogenation. These compounds are useful as cytotoxic agents, in particular, antitumor agents.
    Type: Grant
    Filed: January 21, 1977
    Date of Patent: February 14, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Stephen M. Coppell, Terence A. Harrow
  • Patent number: 4072686
    Abstract: The present invention encompasses compounds of the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof wherein the Alk is straight or branched chain alkylene containing 2-4 carbon atoms; M is alkylene having 1-4 carbon atoms; Ar and Ar' are phenyl, alkyl substituted phenyl wherein the alkyl contains from 1-4 carbon atoms or halo substituted phenyl; Ar" is phenyl, alkyl substituted phenyl wherein the alkyl contains 1-4 carbon atoms, halo substituted phenyl or pyridyl; X is hydrogen, halogen, trifluoromethyl or alkyl having from 1-4 carbon atoms; R is hydrogen alkyl having from 1-7 carbon atoms or an alkanoyl having from 2-5 carbon atoms. These compounds are potent antidiarrheal agents characterized by little, if any, central nervous system activity.
    Type: Grant
    Filed: October 18, 1976
    Date of Patent: February 7, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Gilbert W. Adelstein, Esam Z. Dajani, Chung H. Yen
  • Patent number: 4066654
    Abstract: The present invention encompasses compounds of the formula ##STR1## wherein the Alk is straight or branched chain alkylene containing 2-4 carbon atoms; Ar and Ar' are phenyl, Alkyl substituted phenyl wherein the alkyl contains from 1-4 carbon atoms or halo substituted phenyl; Ar" is phenyl, alkyl substituted phenyl wherein the alkyl contains 1-4 carbon atoms, halo substituted phenyl or pyridyl; X is hydrogen, halogen, trifluoromethyl or alkyl having from 1-4 carbon atoms; R is hydrogen, alkyl having from 1-7 carbon atoms, alkenyl having 3-7 carbon atoms, Ar" as herein before defined, or a cation selected from the group consisting of sodium, potassium, ammonium or calcium/2. Compounds of the present invention are potent antidiarrheal agents with little, if any, central nervous system activity.
    Type: Grant
    Filed: November 15, 1976
    Date of Patent: January 3, 1978
    Assignee: G. D. Searle & Co.
    Inventors: Gilbert W. Adelstein, Esam Z. Dajani, Chung Hwai Yen
  • Patent number: 4064350
    Abstract: The present invention encompasses compounds of the formula: ##STR1## wherein one of A and B is methyl and the other is hydrogen, the wavy line represents R or S stereochemistry, n is 2-5, and R is hydrogen or lower alkyl having 1-7 carbon atoms.
    Type: Grant
    Filed: November 22, 1976
    Date of Patent: December 20, 1977
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4062941
    Abstract: The present invention encompasses a method for treating fungal infections in animals comprising administering to animals in need of antifungal treatment an effective amount of fungal cell lytic enzymes extracted from Coprinus, Lycoperdon, or Bolbitius in conjunction with conventional antimycotic agents such as amphotericin B or Nystatin. The fungal cell lytic enzymes are extracted from Coprinus, Lycoperdon, and Bolbitius by conventional enzyme isolation techniques. These fungal cell lytic enzymes retain their activity in vivo, are relatively non toxic and destroy fungi by degrading fungal cell walls and weakening the fungal cell walls so that conventional antimycotic agents are far more effective. The method of the present invention is particularly useful in treating infections by opportunistic fungi such as Aspergillus fumigatus and Candida albicans.
    Type: Grant
    Filed: May 24, 1976
    Date of Patent: December 13, 1977
    Assignee: G. D. Searle & Co. Ltd.
    Inventor: David Allen Lewis Davies
  • Patent number: 4062921
    Abstract: New solvents for chitin comprising dimethylacetamide, N-methylpyrrolidone or mixtures of these in combination with a minor proportion of lithium chloride, and their use in the purification of chitin for regeneration in the form of films and fibers are described.
    Type: Grant
    Filed: February 19, 1976
    Date of Patent: December 13, 1977
    Assignee: University of Delaware
    Inventor: Paul R. Austin
  • Patent number: 4060691
    Abstract: 7-{3-Hydroxy-2-[4-hydroxy-4-(lower alkyl)-trans-1-octen-1-yl]-5-oxocyclopent-1-yl{heptanoic acids and esters, displaying valuable pharmacological properties, e.g., gastric anti-secretory, are produced by the reaction of a 7-(3-oxygenated-5-oxocyclopent-1-en-1-yl)heptanoic acid or ester with the appropriate organometallic reagent.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: November 29, 1977
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4059457
    Abstract: Solutions of chitin in dimethylacetamide, N-methylpyrrolidone or mixtures of these in combination with a minor proportion of lithium chloride.
    Type: Grant
    Filed: September 30, 1976
    Date of Patent: November 22, 1977
    Assignee: The University of Delaware
    Inventor: Paul Rolland Austin
  • Patent number: 4057549
    Abstract: The present invention comprehends a method for treating diarrhea comprising administering to an animal in need of anti-diarrheal treatment an effective antidiarrheal amount of a compound of the formula ##STR1## and acid addition salts thereof wherein Y is alkylene containing 1-4 carbon atoms; R.sub.2 and R.sub.3 together with N is a heterocyclic ring system comprising azamonocyclic ring of the forumula ##STR2## wherein Z is phenylhydroxymethylmethylene, phenylhydroxymethylene, phenylcarboxymethylene, phenylcarbalkoxymethylene or azabicycloalkyl or phenyl or hydroxyl substituted azabicycloalkyl containing 6-9 carbon atoms and containing at least 5 atoms in each ring of azabicycloalkyl or 4-azatricyclo[4.3.1.1.sup.3,8 ]undec-4-yl; Ar.sub.1 and Ar.sub.2 are phenyl, halo-substituted phenyl, (lower alkyl) substituted phenyl, pyridyl, thienyl or furyl, and Ar.sub.
    Type: Grant
    Filed: October 18, 1976
    Date of Patent: November 8, 1977
    Assignee: G. D. Searle & Co.
    Inventors: Gilbert W. Adelstein, Esam Z. Dajani, Chung Hwai Yen
  • Patent number: RE29556
    Abstract: The present invention relates to compounds of the following formula ##STR1## wherein Y is straight or branched chain alkylene containing 1-4 carbon atoms; R.sub.1 is lower alkyl containing 1-7 carbon atoms; X is hydrogen, halo such as fluoro, chloro, bromo or iodo, or lower alkyl containing 1-7 carbon atoms; Ar is phenyl, 2-pyridyl, mono-substituted phenyl, wherein the substituent is halo such as fluoro, chloro, or bromo, or lower alkyl containing 1-7 carbon atoms; and R.sub.2 and R.sub.3 are lower alkyl containing 1-7 carbon atoms, or R.sub.2 and R.sub.3 together with N is an azamonocyclic ring selected from the group comprising pyrrolidinyl, piperidino, 4-phenyl-4-hydroxypiperidino, 4-phenyl-4-carboxypiperidino, 4-phenyl-4-carbalkoxypiperidino, or 4-phenyl-4-acetoxypiperidino substituted piperidino and morpholino, or an azabicyclo-alkane containing 6 to 9 carbon atoms and containing at least 5 atoms in each ring of the azabicycloalkane.
    Type: Grant
    Filed: September 2, 1976
    Date of Patent: February 28, 1978
    Assignee: G. D. Searle & Co.
    Inventor: Gilbert W. Adelstein