Patents Represented by Attorney John T. Reynolds
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Patent number: 4297339Abstract: Controlled release cycloheximide/emulsifier/oxidized wax compositions useful, per se, in prill form, powder form, dusts, or physically bonded to carrier particles to extend the useful fungicide life of CHI in agricultural applications.Type: GrantFiled: August 25, 1980Date of Patent: October 27, 1981Assignee: The Upjohn CompanyInventor: Richard L. Craven
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Patent number: 4296239Abstract: 6-Amino-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.3 -alkyl, R.sub.1 is hydrogen or halogen, and the two R.sub.2 groups are taken together with the nitrogen to which they are bonded to complete a nitrogen ring moiety selected from the group consisting of pyrrolidino, piperidino, morpholino and 3,6-dihydro-1(2H)-pyridyl, and the pharmacologically acceptable salts thereof, are central nervous system depressant drugs which are useful in effective dosages in domestic and zoo animals for their calming and tranquilizing uses during shipment and to reduce aggressive behavior. In man these compounds are potentially useful for controlling anxiety and schizophrenia and for their sedative, muscle relaxant and anti-convulsant activity.Type: GrantFiled: July 30, 1979Date of Patent: October 20, 1981Assignee: The Upjohn CompanyInventor: Jackson B. Hester, Jr.
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Patent number: 4250094Abstract: 1-(Aminoalkyl) substituted-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula II: ##STR1## wherein R.sub.0 is selected from the group consisting of hydrogen, methyl, or ethyl; wherein R' and R" are selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl as defined above; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl as defined above, halogen, nitro, cyano, trifluoromethyl, and alkoxy, alkylthio, alkylsulfinyl, and alkylsulfonyl, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive, are prepared by reacting a compound of the formula: ##STR2## wherein X is chlorine or bromine and wherein R.sub.0, R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are defined as above with an amine of the formula: ##STR3## wherein R' and R" are defined as above.Type: GrantFiled: July 5, 1979Date of Patent: February 10, 1981Assignee: The Upjohn CompanyInventor: Jackson B. Hester, Jr.
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Patent number: 4226790Abstract: Thallium (l) alkanoate salts are oxidized to thallium (lll) salts in a liquid medium with a peroganic carboxylic acid in the presence of a reactive form of manganese or ruthenium.Type: GrantFiled: August 14, 1978Date of Patent: October 7, 1980Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4217362Abstract: Anilide derivative compounds of the formula ##STR1## e.g., trans-N-(2-hydroxycyclopentyl)-3',4'-dichloropropionanilide, have been found to possess potent Central Nervous System (CNS) antidepressant properties.These compounds are promising antidepressant drugs which are characterized by less toxicity than imipramine, and long-acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are also disclosed.Type: GrantFiled: August 3, 1978Date of Patent: August 12, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4215114Abstract: Cis - and trans-N-(2-aminocycycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-[(2-furylmethyl)methylamino]-cyclohexyl]-3,4-dichlorobenzami de, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm-blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.Type: GrantFiled: March 5, 1979Date of Patent: July 29, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4212878Abstract: N-[(1-Amino-4-(mono or di-oxygen-group-substituted)cyclohex-1-yl)methyl]phenylacetamide derivatives of the formula 1 ##STR1## wherein R, R.sub.1, R.sub.2, R.sub.3, P, Q, X and Y are defined in the specification, e.g., 2-(3,4-dichlorophenyl)-N-[[8-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]dec.-8-yl ]methyl]acetamide, and their pharmacologically acceptable salts, have analgesic drug properties with lower physical dependence liability characteristics than morphine or methadone, for use as analgesic drugs in mammalian animals including humans.Type: GrantFiled: January 26, 1978Date of Patent: July 15, 1980Assignee: The Upjohn CompanyInventors: Daniel Lednicer, Jacob Szmuszkovicz
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Patent number: 4212888Abstract: Anilide derivative compounds of the formula ##STR1## e.g., trans-N-(2-hydroxycyclopentyl)-3',4'-dichloropropionanilide, have been found to possess potent Central Nervous System (CNS) antidepressant properties.These compounds are promising antidepressant drugs which are characterized by less toxicity than imipramine, and long-acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are also disclosed.Type: GrantFiled: August 3, 1978Date of Patent: July 15, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4204003Abstract: N-(2-Aminocyclopentyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cyclopentyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by a better therapeutic ratio than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: February 9, 1978Date of Patent: May 20, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4197308Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-(N-pyrrolidinyl)cyclohexyl]-3,4- dichlorobenzamide, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.Type: GrantFiled: May 10, 1978Date of Patent: April 8, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4194053Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.Type: GrantFiled: September 1, 1978Date of Patent: March 18, 1980Assignee: The Upjohn CompanyInventor: David R. White
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Analgesic N-{2-[N'-(2-furylmethyl and 2-thienyl-methyl)-N'-alkylamino]cycloaliphatic}cyanobenzamides
Patent number: 4192885Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-(N-pyrrolidinyl)cyclohexyl]-3,4-dichlorobenzamide, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.Type: GrantFiled: March 8, 1979Date of Patent: March 11, 1980Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz -
Patent number: 4189596Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.Type: GrantFiled: May 2, 1977Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Verlan H. VanRheenen
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Patent number: 4180668Abstract: 6-Amino-4H-s-triazolo[4,3-a][1,4]benzodiazepines of the formula ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.3 -alkyl, R.sub.1 is hydrogen or halogen, and the two R.sub.2 groups are taken together with the nitrogen to which they are bonded to complete a nitrogen ring moiety selected from the group consisting of pyrrolidino, piperidino, morpholino and 3,6-dihydro-1(2H)-pyridyl, and the pharmacologically acceptable salts thereof, are central nervous system depressant drugs which are useful in effective dosages in domestic and zoo animals for their calming and tranquilizing uses during shipment and to reduce aggressive behavior. In man these compounds are potentially useful for controlling anxiety and schizophrenia and for their sedative, muscle relaxant and anti-convulsant activity.Type: GrantFiled: June 8, 1977Date of Patent: December 25, 1979Assignee: The Upjohn CompanyInventor: Jackson B. Hester, Jr.
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Patent number: 4179501Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-(N-pyrrolidinyl)cyclohexyl]-3,4-dichlorobenzamide, and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in warm blooded animals, as well as methods for alleviating pain in animals with these compositions. Processes for preparing the compounds are also disclosed.Type: GrantFiled: May 10, 1978Date of Patent: December 18, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4172898Abstract: N-(2-aminocycloheptyl)-N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cycloheptyl]acrylanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by lower toxicity than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: May 30, 1978Date of Patent: October 30, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4169156Abstract: N-(2-aminocycloheptyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(allylamino)cycloheptyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System antidepressant properties. Many of them are new.These compounds are promising antidepressant drugs which are characterized by lower toxicity than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: June 5, 1978Date of Patent: September 25, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4159339Abstract: N-(2-aminocycloheptyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cycloheptyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System antidepressant properties. Many of them are new.These compounds are promising antidepressant drugs which are characterized by lower toxicity than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: May 30, 1978Date of Patent: June 26, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4159340Abstract: N-(2-Aminocyclopentyl)-N-acylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(N-allylamino)cyclopentyl]propionanilide, and their pharmacologically acceptable salts have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by a better therapeutic ratio than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: May 15, 1978Date of Patent: June 26, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4157398Abstract: N-(2-Aminocyclopentyl)N-alkanoylanilides and their 2-N-oxides of the formula ##STR1## e.g., trans-3,4-dichloro-N-[2-(dimethylamino)cyclopentyl]propionanilide, and their pharmacologically acceptable salts, have been found to possess potent Central Nervous System anti-depressant properties. Many of them are new.These compounds are promising anti-depressant drugs which are characterized by a better therapeutic ratio than imipramine, and long acting activity which may allow longer durations between administrations, e.g., once a day. Pharmaceutical compositions containing these compounds and a process for treating conditions of depression with these compositions are disclosed.Type: GrantFiled: February 21, 1978Date of Patent: June 5, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz