Patents Examined by G. Thomas Todd
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Patent number: 3951984Abstract: 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: GrantFiled: December 18, 1973Date of Patent: April 20, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Michio Kimura, Takeshi Nakajima, Toshio Atsumi, Kenji Kobayashi, Yoshiaki Takebayashi, Shigeho Inaba, Hisao Yamamoto
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Patent number: 3951970Abstract: 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: GrantFiled: October 1, 1973Date of Patent: April 20, 1976Assignee: Sharps AssociatesInventors: Raj Kumar Razdan, Harry George Pars
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Patent number: 3951985Abstract: 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: GrantFiled: February 27, 1973Date of Patent: April 20, 1976Assignee: Chemie Grunenthal GmbHInventors: Ivars Graudums, Heinrich Muckter, Ernst Frankus
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Patent number: 3950346Abstract: 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: GrantFiled: May 3, 1973Date of Patent: April 13, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Atsumi, Kenji Kobayashi, Yoshiaki Takebayashi, Hisao Yamamoto
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Patent number: 3947511Abstract: 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: GrantFiled: November 25, 1970Date of Patent: March 30, 1976Assignee: E. I. Du Pont de Nemours and CompanyInventor: Maynard S. Raasch
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Patent number: 3947459Abstract: 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: GrantFiled: October 4, 1974Date of Patent: March 30, 1976Assignee: The Goodyear Tire & Rubber CompanyInventors: Penelope R. Pappas, Dane K. Parker
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Patent number: 3946033Abstract: 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: GrantFiled: November 20, 1973Date of Patent: March 23, 1976Assignee: Teijin Ltd.Inventors: Kaoru Iwata, Shigeyoshi Hara
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Patent number: 3946021Abstract: 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: GrantFiled: June 28, 1973Date of Patent: March 23, 1976Assignee: Richardson-Merrell Inc.Inventors: William L. Albrecht, Robert W. Fleming
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Patent number: 3946029Abstract: 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: GrantFiled: January 31, 1974Date of Patent: March 23, 1976Assignee: LabazInventors: Margel Descamps, Henri Inion
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Patent number: 3943139Abstract: A new process for producing triacetone-amine by reacting phoron and ammonia under pressure and higher temperature.Type: GrantFiled: October 4, 1973Date of Patent: March 9, 1976Assignee: CIBA-GEIGY CorporationInventors: Ivan Orban, Jean Rody
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Patent number: 3941796Abstract: .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: GrantFiled: July 11, 1974Date of Patent: March 2, 1976Assignee: Minnesota Mining and Manufacturing CompanyInventors: George H. Sankey, Keith D. E. Whiting
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Patent number: 3941795Abstract: 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: GrantFiled: February 8, 1974Date of Patent: March 2, 1976Assignee: Richardson-Merrell Inc.Inventors: Albert A. Carr, C. Richard Kinsolving
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Patent number: 3939166Abstract: 4,5-Disubstituted-7-nitro-2-(.alpha.,.alpha.-difluoroalkyl)benzimidazole compounds and their alkali metal and alkaline earth metal salts, useful as insecticides.Type: GrantFiled: November 15, 1973Date of Patent: February 17, 1976Assignee: Eli Lilly and CompanyInventors: John L. Miesel, David I. Wickiser
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Patent number: 3937709Abstract: 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: GrantFiled: June 15, 1973Date of Patent: February 10, 1976Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Thierry Sevenet, Claude Thal, Henri Philippe Husson, Pierre Potier
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Patent number: 3936463Abstract: 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: GrantFiled: December 3, 1973Date of Patent: February 3, 1976Assignee: Bayer AktiengesellschaftInventors: Otto Behner, Ulrich Horlein, Friedrich Hoffmeister, Hans Werner Schubert
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Patent number: 3936464Abstract: This disclosure describes new substituted 1-acyl-3-[2-(4-phenyl-1-piperidinyl)ethyl]indolines which possess hypotensive activity.Type: GrantFiled: October 25, 1974Date of Patent: February 3, 1976Assignee: American Cyanamid CompanyInventors: George Rodger Allen, Jr., Francis Joseph McEvoy
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Patent number: 3933847Abstract: 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: GrantFiled: December 19, 1973Date of Patent: January 20, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Masaaki Ohkawa, Koichi Ishii
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Patent number: 3933831Abstract: 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: GrantFiled: November 7, 1973Date of Patent: January 20, 1976Assignee: PCR, Inc.Inventors: Ralph J. De Pasquale, Keith B. Baucom
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Patent number: 3932422Abstract: 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: GrantFiled: May 20, 1974Date of Patent: January 13, 1976Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 3932423Abstract: 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: GrantFiled: May 28, 1974Date of Patent: January 13, 1976Assignee: Yoshitomi Pharmaceutical IndustriesInventors: Katsuo Arimura, Hideki Ao