Patents Examined by G. Thomas Todd
  • Patent number: 3951984
    Abstract: A 3-benzazocine compound of the formula: ##SPC1##Wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5 and R.sub.8 are each hydrogen or lower alkyl, R.sub.2 is hydrogen, lower alkyl or phenyl and R.sub.6 and R.sub.7 are each lower alkyl, and its pharmaceutically acceptable acid addition salts, which are useful as analgesics and can be produced by reacting a tetrahydropyridine compound of the formula: ##SPC2##Wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each as defined above or its salt with a Lewis acid.
    Type: Grant
    Filed: December 18, 1973
    Date of Patent: April 20, 1976
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Michio Kimura, Takeshi Nakajima, Toshio Atsumi, Kenji Kobayashi, Yoshiaki Takebayashi, Shigeho Inaba, Hisao Yamamoto
  • Patent number: 3951970
    Abstract: Compounds of the formula ##SPC1##And acid addition salts thereof, wherein R represents an alkyl group having 1 to 20 carbon atoms, an arylalkyl group, or a cycloalkyl-lower alkyl group, R.sub.1 and R.sub.2 represent hydrogen or the same or different lower alkyl or lower alkanoyl groups; and Z represents --NH.sub.2, --NHR.sub.3, --NR.sub.3 R.sub.4, or ##EQU1## WHERE R.sub.3 is lower alkyl, or phenyl-lower alkyl, R.sub.4 is lower alkyl or phenyl-lower alkyl, m is an integer from 0 to 6, n is an integer from 0 to 6, m + n is an integer from 3 to 6, and X is CH.sub.2, CHR.sub.3, O, S, or NR.sub.3.The compounds have pharmacological activity, including antidepressant and anti-hypertensive activity, in animals.
    Type: Grant
    Filed: October 1, 1973
    Date of Patent: April 20, 1976
    Assignee: Sharps Associates
    Inventors: Raj Kumar Razdan, Harry George Pars
  • Patent number: 3951985
    Abstract: Lactams of the substituted ortho-sulfobenzoic acid imido pyrrolidone-2, piperidone-2, or caprolactam type. The compounds are useful drugs having therapeutical properties. They are immunosuppressive, sedative, and have antitumor activity. They are produced, for instance, by reacting bromo-lactams with a metal salt of o-sulfobenzoic acid imide.
    Type: Grant
    Filed: February 27, 1973
    Date of Patent: April 20, 1976
    Assignee: Chemie Grunenthal GmbH
    Inventors: Ivars Graudums, Heinrich Muckter, Ernst Frankus
  • Patent number: 3950346
    Abstract: 2-Ketoethyl-6,7-benzomorphan derivatives of the formula: ##SPC1##And their pharmaceutically acceptable non-toxic salts, which are useful as non-addictive analgesics and pain-relieving agents and can be prepared by reacting the corresponding 6,7-benzomorphan derivative of the formula: ##SPC2##With a vinyl carbonyl compound of the formula: ##EQU1## [wherein R' is a hydrogen atom or a group of the formula: --OR" (wherein R" is a hydrogen atom, an alkanoyl group, an alkyl group, an aralkyl group, an alkoxycarbonylmethyl group or a tetrahydropyranyl group), R.sub.1 is a hydrogen atom, an alkyl group or a substituted or unsubstituted aryl group, R.sub.2 is a hydrogen atom or an alkyl group and A is an alkyl group, an alkoxy group, a substituted or unsubstituted aryl group or a substituted or unsubstituted amino group].
    Type: Grant
    Filed: May 3, 1973
    Date of Patent: April 13, 1976
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshio Atsumi, Kenji Kobayashi, Yoshiaki Takebayashi, Hisao Yamamoto
  • Patent number: 3947511
    Abstract: Novel 1-hydrocarbyl-3-(thiocarbamoylthio)ureas and 1-hydrocarbyl-3-(carbamoylthio)ureas are prepared by reacting, in liquid phase, an appropriate isocyanate and S-thiocarbamoylhydrosulfamine or S-carbamoylhydrosulfamine, e.g., S-(dimethylthiocarbamoyl)-N-methylhydrosulfamine or S-(dimethylcarbamoyl)hydrosulfamine. All the compounds are useful as rubber-curing agents.
    Type: Grant
    Filed: November 25, 1970
    Date of Patent: March 30, 1976
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Maynard S. Raasch
  • Patent number: 3947459
    Abstract: This invention relates to an improved process for preparing thiazolesulfenamides from aqueous chloramines and alkali metal salts of mercaptothiazoles, in water. The chloramine mixture can be prepared from amines or aqueous amine salt solutions.
    Type: Grant
    Filed: October 4, 1974
    Date of Patent: March 30, 1976
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Penelope R. Pappas, Dane K. Parker
  • Patent number: 3946033
    Abstract: Hydantoin derivatives are produced by reacting1. a glycine derivative,2. a primary amine, and3. a diaryl carbonateThus, various kinds of hydantoin derivatives can be obtained without using an isocyanate.
    Type: Grant
    Filed: November 20, 1973
    Date of Patent: March 23, 1976
    Assignee: Teijin Ltd.
    Inventors: Kaoru Iwata, Shigeyoshi Hara
  • Patent number: 3946021
    Abstract: The novel bis-basic ketones of carbazole of the present invention have antiviral activity when administered orally and parenterally. These compounds are represented by the following formula: ##SPC1##Wherein Z is hydrogen or lower alkyl having from 1 to 4 carbon atoms; A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y isA. the group ##EQU1## wherein R.sup.1 and R.sup.2 are individually hydrogen or lower alkyl having from 1 to about 4 carbon atoms; orB. the group ##SPC2##Wherein n is a whole integer of 4 or 5, and R.sup.3 is hydrogen or lower alkyl having from 1 to about 4 carbon atoms and can be linked to any one of the carbon atoms of the heterocyclic group; orC. the group ##SPC3##Wherein X is oxygen or NR.sup.4, and R.sup.4 is hydrogen or lower alkyl of from 1 to about 4 carbon atoms;Or a pharmaceutically acceptable acid addition salt of said base.These new compounds can be prepared by several different methods which are described.
    Type: Grant
    Filed: June 28, 1973
    Date of Patent: March 23, 1976
    Assignee: Richardson-Merrell Inc.
    Inventors: William L. Albrecht, Robert W. Fleming
  • Patent number: 3946029
    Abstract: 3-Indolyl pyridyl ketones of the general formula: ##SPC1##And pharmaceutically acceptable acid addition salts thereof wherein R.sub.1 representsA straight- or branched-chain saturated or unsaturated alkyl group having not more than 6 carbon atoms, a benzyl group optionally substituted in the aromatic portion of a chlorine atom or a methoxy groupOr ##EQU1## wherein A represents an alkylene chain of from 2 to 6 carbon atoms and R.sub.4 and R.sub.5, which may be the same or different, are each an alkyl group having from 1 to 5 carbon atoms, or R.sub.4 and R.sub.5 are joined together to form with the nitrogen atom a piperidino, pyrrolidino or morpholino group,R.sub.2 representsA branched- or straight-chain alkyl group having from 1 to 4 carbon atoms, a phenyl group optionally substituted by a fluorine, chlorine, or bromine atom or a methoxy or cyclohexyl group; andR.sub.3 representsA 2-pyridyl, 3-pyridyl or 4-pyridyl group.They are effective as fibrinolytic and anti-inflammatory agents.
    Type: Grant
    Filed: January 31, 1974
    Date of Patent: March 23, 1976
    Assignee: Labaz
    Inventors: Margel Descamps, Henri Inion
  • Patent number: 3943139
    Abstract: A new process for producing triacetone-amine by reacting phoron and ammonia under pressure and higher temperature.
    Type: Grant
    Filed: October 4, 1973
    Date of Patent: March 9, 1976
    Assignee: CIBA-GEIGY Corporation
    Inventors: Ivan Orban, Jean Rody
  • Patent number: 3941796
    Abstract: .alpha.-(Hydroxy and alkoxy substituted)phenyl-.alpha.-(2-piperidinyl)methanols of the formula ##SPC1##Where R is hydrogen or lower alkyl, R.sup.1 is hydrogen, hydroxy or lower alkoxy, and R.sup.2 is phenyl, phenyl-lower alkyl, diphenyl-lower alkyl, phenoxy-lower alkyl or diphenoxy-lower alkyl, and the non-toxic pharmaceutically acceptable acid-addition and quaternary ammonium salts thereof.
    Type: Grant
    Filed: July 11, 1974
    Date of Patent: March 2, 1976
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: George H. Sankey, Keith D. E. Whiting
  • Patent number: 3941795
    Abstract: Novel compounds useful as antihistamine agents, antiallergy agents, and bronchodilators are represented by the following formula ##SPC1##Wherein R.sup.1 represents cyclohexyl, phenyl, or substituted phenyl wherein the substituent on the substituted phenyl is selected from halogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, or a lower alkoxy group of from 1 to 4 carbon atoms; R.sup.2 represents hydrogen or hydroxy; R.sup.3 represents hydrogen, or R.sup.2 and R.sup.3 taken together form a second bond between the carbon atoms bearing R.sup.2 and R.sup.
    Type: Grant
    Filed: February 8, 1974
    Date of Patent: March 2, 1976
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, C. Richard Kinsolving
  • Patent number: 3939166
    Abstract: 4,5-Disubstituted-7-nitro-2-(.alpha.,.alpha.-difluoroalkyl)benzimidazole compounds and their alkali metal and alkaline earth metal salts, useful as insecticides.
    Type: Grant
    Filed: November 15, 1973
    Date of Patent: February 17, 1976
    Assignee: Eli Lilly and Company
    Inventors: John L. Miesel, David I. Wickiser
  • Patent number: 3937709
    Abstract: New compounds having the formula ##SPC1##In which Y represents a hydrogen atom, in which case Z.sub.1 and Z.sub.2 represent simultaneously an oxygen atom, or Z.sub.1 represents a methoxycarbonyl radical and Z.sub.2 a hydroxy radical, or Y and Z.sub.2 form together a carbon-carbon bond and Z.sub.1 is a methoxycarbonyl radical, said compounds being additionally characterized by a cis-fusion of the D/E rings. Said new compounds and vincamine and certain of its derivatives are prepared from an enamine having the formula: ##SPC2##In which R is H or C.sub.2 H.sub.5.
    Type: Grant
    Filed: June 15, 1973
    Date of Patent: February 10, 1976
    Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)
    Inventors: Thierry Sevenet, Claude Thal, Henri Philippe Husson, Pierre Potier
  • Patent number: 3936463
    Abstract: Benzomorphanes of the formula: ##SPC1##WhereinR is cyclopropylmethyl or cyclobutylmethyl;R.sup.1 and R.sup.2 are the same or different and each is lower alkyl;R.sup.
    Type: Grant
    Filed: December 3, 1973
    Date of Patent: February 3, 1976
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Behner, Ulrich Horlein, Friedrich Hoffmeister, Hans Werner Schubert
  • Patent number: 3936464
    Abstract: This disclosure describes new substituted 1-acyl-3-[2-(4-phenyl-1-piperidinyl)ethyl]indolines which possess hypotensive activity.
    Type: Grant
    Filed: October 25, 1974
    Date of Patent: February 3, 1976
    Assignee: American Cyanamid Company
    Inventors: George Rodger Allen, Jr., Francis Joseph McEvoy
  • Patent number: 3933847
    Abstract: A coumarin dye of the formula (Ia), ##SPC1##Wherein R.sub.1 is hydrogen, chlorine or C.sub.1 -C.sub.2 alkyl, R.sub.2 and R.sub.3 are hydrogen or C.sub.1 -C.sub.4 alkyl, or a quarternary salt thereof having the formula (Ib), ##SPC2##Wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, R.sub.4 is C.sub.1 -C.sub.2 alkyl or benzyl, and X.sup.- is an anion, is prepared by an improved method, which comprises reacting a diamine of the formula, ##SPC3##Wherein R.sub.1 is as defined above, with a compound of the formula,X -- CH.sub.2 -- Ywherein X and Y are the same or different and are carboxyl, carbamoyl, alkoxycarbonyl or cyano, in 10 to 70 % sulfuric acid to prepare an imidazolyl acetic acid of the formula, ##SPC4##Wherein R.sub.1 is as defined above, and then reacting the imidazolyl acetic acid with a compound of the formula, ##SPC5##Wherein R.sub.2 and R.sub.3 are as defined above, to obtain the dye (Ia), or further reacting the resulting dye (Ia) with an alkylating agent to obtain the dye (Ib).
    Type: Grant
    Filed: December 19, 1973
    Date of Patent: January 20, 1976
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaaki Ohkawa, Koichi Ishii
  • Patent number: 3933831
    Abstract: Thermally and oxidatively stable perfluorinated tertiary amines of the formula: ##EQU1## ARE DISCLOSED, AS WELL AS THE PROCESS FOR MAKING THESE AND OTHER COMPOUNDS. The carbonyl group of imides or amides is reduced with SF.sub.4 using HF as the reaction solvent at a reaction temperature of 25.degree.-300.degree.C. Cyclic imides can be used as starting compounds, and tertiary amines containing unsaturated moieties can be produced.The perfluorinated tertiary amines have various uses in view of their high degree of thermal and oxidative stability, including uses as hydraulic fluids or transformer dielectric fluids.
    Type: Grant
    Filed: November 7, 1973
    Date of Patent: January 20, 1976
    Assignee: PCR, Inc.
    Inventors: Ralph J. De Pasquale, Keith B. Baucom
  • Patent number: 3932422
    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: May 20, 1974
    Date of Patent: January 13, 1976
    Assignee: Sterling Drug Inc.
    Inventor: William F. Michne
  • Patent number: 3932423
    Abstract: Imidazolido[1,5-c]thiazolidine-3-spiro-4'-piperidine compounds of the formula: ##SPC1##Wherein R.sup.1 represents a member selected from the group consisting of a hydrogen atom, an alkyl group of from 1 to 4 carbon atoms, a benzyl group, a p-chlorobenzyl group, a 4,5-dimethoxybenzyl group, a 4,5,6-trimethoxybenzyl group, a phenethyl group, an acetyl group, a benzoyl group, a trimethoxybenzoyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 4,4-bis(p-fluorophenyl)butyl group and a group of the formula ##SPC2##(in which Y represents a member selected from the group consisting of H, F and CH.sub.3 O, and n represents an integer of 1, 2 or 3); R.sup.
    Type: Grant
    Filed: May 28, 1974
    Date of Patent: January 13, 1976
    Assignee: Yoshitomi Pharmaceutical Industries
    Inventors: Katsuo Arimura, Hideki Ao