Patents Represented by Attorney John T. Reynolds
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Patent number: 4156733Abstract: 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: May 29, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4156014Abstract: 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: March 13, 1978Date of Patent: May 22, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4156015Abstract: 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-depresssant 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: April 10, 1978Date of Patent: May 22, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4153717Abstract: Cis- and trans-N-(2-aminocycloaliphatic)benzamide compounds of the formula ##STR1## e.g., N-methyl-N-[2-[(2-furylmethyl)methylamino]cyclohexyl]-3,4-dichlorobenzamid e, 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 15, 1978Date of Patent: May 8, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4152459Abstract: 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 parmaceutically 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: May 1, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4148914Abstract: 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 10, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4148913Abstract: 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: April 10, 1978Date of Patent: April 10, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuskovicz
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Patent number: 4145435Abstract: Cis- and trans-N-(2-aminocycloaliphatic)-2-arylacetamide derivative compounds of the formula ##STR1## e.g., N-?2-(N', N'-dimethylamino)cyclohexyl!-N-methyl-2-(4-bromophenyl)acetamide and trans-N-methyl-N-?2-(1-pyrrolidinyl)cyclohexyl!acetamide, 2-(3,4-dichlorophenyl) and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and the preferred compounds have in addition only low to moderate apparent physical dependence liability, compared to morphine and methadone. As analgesics they would be useful also as antitussives. Processes for preparation of these compounds are also disclosed. This invention also includes compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in humans and animals, as well as methods for alleviating pain in animals and humans with these compositions.Type: GrantFiled: November 12, 1976Date of Patent: March 20, 1979Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4145440Abstract: Liquid pharmaceutical suspensions of aluminum ibuprofen salts, which are gel resistant, non-caking, have controlled sedimentation properties and which are easily re-suspended by shaking the suspension bottle, can be obtained by dispersing aluminum ibuprofen salts in a sorbitol/glycerin/water mixture containing controlled maximum amounts of pharmaceutically acceptable suspending agents and water soluble surface active agents.Type: GrantFiled: August 18, 1977Date of Patent: March 20, 1979Assignee: The Upjohn CompanyInventors: Kandy A. Fitch, Englebert L. Rowe
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Patent number: 4142054Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. A continuous process using a Scheibel column is disclosed. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: February 27, 1979Assignee: The Upjohn CompanyInventors: Sanjay I. Amin, Jerry A. Walker
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Patent number: 4135051Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: January 16, 1979Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4128556Abstract: Multiheteromacrocycles are disclosed that contain as part of the macrocycle, assemblies of 2,6-dimethylylpyridine (and their corresponding amine oxides), 2,5-dimethylylfuran, 2,5-dimethylyltetrahydrofuran, Diels-Alder adducts of 2,5-dimethylylfuran (and their reduction products), 2- and 4-substituted 1,3-dimethylbenzenes, pentamethylene, or p-phenylene coupled through oxygen to one another, or to ethylene, o-phenylene, or 1,1-binaphthyl-2,2- units (always coupled through oxygens) to form multidentate ligands for complexing selectively alkylammonium or metal cations.Type: GrantFiled: November 21, 1977Date of Patent: December 5, 1978Assignee: The Regents of the University of CaliforniaInventor: Donald J. Cram
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Patent number: 4128663Abstract: 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: May 16, 1977Date of Patent: December 5, 1978Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4113959Abstract: Chiral, hinged, asymmetric host binaphthyl-based multiheteromacrocycles of oxygen covalently bonded to styrene/divinylbenzene copolymers are provided. These new compounds have specific chiral recognition properties, which properties make these new compounds useful for separating or resolving racemic and other mixtures of amino acids, amino acid esters and salts thereof for either or both of analytical purposes or large scale manufacturing procedures.Type: GrantFiled: June 13, 1977Date of Patent: September 12, 1978Assignee: The Regents of the University of CaliforniaInventor: Donald J. Gram
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Patent number: 4107439Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1976Date of Patent: August 15, 1978Assignee: The Upjohn CompanyInventors: Jerry A. Walker, David R. White, William G. Salmond
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Patent number: 4098904Abstract: 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: November 12, 1976Date of Patent: July 4, 1978Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz
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Patent number: 4082761Abstract: This invention relates to novel benzodiazepinium compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, lower alkyl of 1 through 3 carbon atoms, hydroxy, mercapto, amino, monoalkylamino of 1 through 3 carbon atoms, arylamino wherein the aryl moiety is selected from the group consisting of unsubstituted and monosubstituted phenyl and naphthyl, alkanoylamino of 1 through 4 carbon atoms, aroylamino wherein the aroyl moiety is selected from the group consisting of unsubstituted and monosubstituted benzoyl and naphthoyl, alkanesulfonamido of 1 through 3 carbon atoms, and arylsulfonamido wherein the aryl moiety is selected from the group consisting of unsubstituted and monosubstituted phenyl and naphthyl; R.sub.1 is lower alkyl of 1 through 3 carbon atoms; R.sub.2 is selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; R.sub.3, R.sub.4, R.sub.5 and R.sub.Type: GrantFiled: September 4, 1973Date of Patent: April 4, 1978Assignee: The Upjohn CompanyInventor: Jackson B. Hester, Jr.
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Patent number: 4080337Abstract: Multiheteromacrocycles are disclosed that contain as part of the macrocycle, assemblies of 2,6-dimethylylpyridine (and their corresponding amine oxides), 2,5-dimethylylfuran, 2,5-dimethylyltetrahydrofuran, Diels-Alder adducts of 2,5-dimethylylfuran (and their reduction products), 2- and 4-substituted 1,3-dimethylylbenzenes, pentamethylene, or p-phenylene coupled through oxygen to one another, or to ethylene, o-phenylene, or 1,1-binaphthyl-2,2- units (always coupled through oxygens) to form multidentate ligands for complexing selectively alkylammonium or metal cations.Type: GrantFiled: March 1, 1976Date of Patent: March 21, 1978Assignee: The Upjohn CompanyInventor: Donald J. Cram
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Patent number: 4043979Abstract: Chiral, hinged, asymmetric host binaphthyl-based multiheteromacrocycles of oxygen covalently bonded to styrene/divinylbenzene copolymers are provided. These new compounds have specific chiral recognition properties, which properties make these new compounds useful for separating or resolving racemic and other mixtures of amino acids, amino acid esters and salts thereof for either or both of analytical purposes or large scale manufacturing procedures.Type: GrantFiled: March 31, 1976Date of Patent: August 23, 1977Assignee: The Regents of the University of CaliforniaInventor: Donald J. Cram
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Patent number: 4025558Abstract: This invention relates to novel benzospiran derivatives embraced by the formula ##STR1## wherein the sum of A and B is at least the integer 2; A is selected from the group consisting of --(CH.sub.2)--.sub.n wherein n is 1 through 5 and --(C.sub.n H.sub.2n -.sub.2 XY)-- wherein X is selected from the group consisting of hydroxy, acetoxy, amino and acetamido and Y is hydrogen, and X when taken together with Y is selected from the group consisting of =O and =CR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; B is absent or --(CH.sub.2)--.sub.n wherein n is 1 through 3; R.sup.1 is selected from the group consisting of hydrogen and lower alkyl of 1 through 3 carbon atoms; R.sup.Type: GrantFiled: October 16, 1975Date of Patent: May 24, 1977Assignee: The Upjohn CompanyInventor: Daniel Lednicer