Five-membered Ring In Substituent Q Patents (Class 564/189)
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4337268Abstract: N-Oximinoalkyl-anilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or optionally substituted aralkyl andR.sup.7 represents furyl, tetrahydrofuryl, thiophenyl, or tetrahydrothiophenyl; isoxazolyl which is optionally substituted in alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl or cycloalkyl; or the grouping --CH.sub.2 Az, --CH.sub.2 --OR.sup.8, --.sub.CH.sub.2 --SR.sup.8, --OR.sup.8, --SR.sup.8, --CH.sub.2 --OSO.sub.2 R.sup.8, --COOR.sup.8 or ##STR2## wherein R.sup.8 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical andAz represents pyrazol-1-yl, 1,2,4-thiazol-1-yl or imidazol-1-yl,which possess fungicidal activity.Type: GrantFiled: May 15, 1980Date of Patent: June 29, 1982Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Wilhelm Brandes
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Patent number: 4329363Abstract: The present application discloses a method of correcting an imbalance of immune homeostasis caused by cytostatic treatment or radiotherapy by administering to a patient in need of such treatment an effective amount of a novel substituted mercapto acid amide and pharmaceutical compositions containing such novel substituted mercapto acid amides.Type: GrantFiled: January 16, 1980Date of Patent: May 11, 1982Assignee: Merck & Co., Inc.Inventors: Conrad P. Dorn, Howard Jones
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Patent number: 4327111Abstract: Mammalian collagenase is inhibited by compounds having the formula ##STR1## or a salt thereof, wherein R.sub.1 is hydrogen, alkanoyl of 2 to 10 carbon atoms, or arylcarbonyl; ##STR2## wherein R.sub.4 is hydrogen, alkyl or aryl; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, aryl or arylalkyl; andn is an integer of 1 to 20.Type: GrantFiled: July 14, 1980Date of Patent: April 27, 1982Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, Tamara Dejneka
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Patent number: 4324730Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions, 4,4; 7,7; 10,10; and 5.Type: GrantFiled: October 8, 1980Date of Patent: April 13, 1982Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4322553Abstract: The disclosure herein relates to a new process for the preparation of N-(halomethyl)acylamides by reacting the corresponding N-(alkoxymethyl)acylamide with thionyl chloride or thionyl bromide in the presence of a Lewis Acid catalyst.Type: GrantFiled: February 2, 1981Date of Patent: March 30, 1982Assignee: Monsanto CompanyInventor: John P. Chupp
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Patent number: 4315031Abstract: This invention relates to thiosubstituted cyclic amino acids, to a process for their preparation and to pharmaceutical compositions containing them together with an inert non toxic pharmaceutical carrier.Type: GrantFiled: August 28, 1978Date of Patent: February 9, 1982Assignee: Science Union et CieInventors: Michel Vincent, Georges Remond, Jacques Bure
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Patent number: 4313005Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.Type: GrantFiled: April 3, 1980Date of Patent: January 26, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Randall J. Daughenbaugh
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Patent number: 4312997Abstract: The present invention provides novel 19-hydroxy-6-oxo-PGF.sub.1 amides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: January 26, 1982Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4311858Abstract: The disclosure herein relates to a new process for the preparation of N-(halomethyl) acylamides by reacting the corresponding N-(alkoxymethyl) acetamide with a hydrogen halide.Type: GrantFiled: December 1, 1980Date of Patent: January 19, 1982Assignee: Monsanto CompanyInventor: John P. Chupp
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Patent number: 4309433Abstract: An aminoalkylbenzene derivative of the formula: ##STR1## [wherein A is oxygen or sulfur;Y is oxo, thioxo, or cyanoimino;a is an integer of 1 to 3;b is an integer of 0 to 3;c is an integer of 1 to 4;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl; orR.sup.1 and R.sup.2 taken together represent pyrrolidinyl;R is hydrogen, cycloalkyl, trihaloalkyl, alkoxy, dialkylamino, aryl, aroyl, heterocyclic group, or a group of the formula: ##STR2## (wherein R.sup.3 is hydrogen, halogen, amino, alkyl, alkylamino, dialkylamino, alkylthio, or aryloxy;R.sup.4 is hydrogen, alkyl, alkenyl, aryl, or heterocyclic group; orR.sup.3 and R.sup.4 taken together represent alkylidene or aralkylidene;with the proviso that the above aryl, aroyl, and heterocyclic group can be substituted by 1 to 3 substituents] and its pharmaceutically acceptable acid addition salts being useful as histamine H.sub.2 blockers, especially peptic ulcer remedies, are provided via several routes.Type: GrantFiled: June 30, 1980Date of Patent: January 5, 1982Assignee: Shionogi & Co., Ltd.Inventors: Kentaro Hirai, Teruyuki Ishiba, Shigeru Matsutani, Itsuo Makino, Toshio Fujishita, Masami Doteuchi, Koichi Otani
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Patent number: 4309424Abstract: Novel 4-phenyl-1,3-benzodiazepines, novel intermediates thereof, and methods of preparing same are described. These benzodiazepines are useful as antidepressants, analgetics and anticonvulsants.Type: GrantFiled: November 5, 1979Date of Patent: January 5, 1982Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
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Patent number: 4307112Abstract: 9-deoxy-9A-methylene-isosteres of PGI.sub.2, including processes for their preparation and pharmaceutical and veterinary compositions containing same, are disclosed. The compounds are useful as therapeutic agents, for example as anti-aggregating agents, disaggregating agents, and as vasodilators.Type: GrantFiled: February 26, 1980Date of Patent: December 22, 1981Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Carlo Passarotti, William Fava, Angelo Fumagalli, Franco Faustini, Roberto Ceserani
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Patent number: 4304733Abstract: Novel alcohols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, arylalkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN and R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 3 carbon atoms in the S form, R form or racemic mixtures thereof whose esters with cyclopropane carboxylic acids have an elevated insecticidal activity and their preparation.Type: GrantFiled: April 17, 1980Date of Patent: December 8, 1981Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4301083Abstract: Polyoxyalkylene compounds having at least four oxyalkylene units and one or two terminal hydroxyl groups are etherified by reacting same with organic primary chlorides or bromides in the presence of an aqueous, at least 30% by weight solution of sodium or potassium hydroxide to produce the corresponding etherified polyoxyalkylene derivatives. The molar ratio of the organohalide to the hydroxyl group(s) of the polyoxyalkylene compound is at least 1.2, and the molar ratio of the alkali metal hydroxide to such hydroxyl group(s) is at least 1.Type: GrantFiled: January 2, 1980Date of Patent: November 17, 1981Assignee: Kuraray Co., Ltd.Inventors: Noriaki Yoshimura, Masuhiko Tamura
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Patent number: 4289770Abstract: New derivatives of 2-benzoyl-4-nitro anilides, their preparation and their use as medicaments.The new chemical derivatives of the invention have the general formula ##STR1## in which R represents a linear or branched alkyl group, an alkenyl group, a cycloalkyl group or a benzyl group,R.sub.1 represents a hydrogen atom, an alkyl group or a hydroxy alkyl group,R.sub.2 represents a hydroxy-alkyl, alkenyl or alkynyl group, possibly substituted one or more times by an alkyl radical, or a cycloalkyl group having three to six carbon atoms;R.sub.1 and R.sub.2 may furthermore form, with the nitrogen atom to which they are attached, a nitrogen heterocycle containing possibly a second heteroatom selected from among oxygen and nitrogen;under the condition, however, that when R.sub.2 represents a hydroxy-alkyl group R.sub.1 may not be a hydrogen atom.Use as hypnotic agents for the treatment of insomnia.Type: GrantFiled: June 13, 1980Date of Patent: September 15, 1981Assignee: Pierre Fabre S.A.Inventors: Henri Cousse, Gilbert Mouzin
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Patent number: 4283350Abstract: The present invention provides novel 19,20-didehydro-PG.sub.2 amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: August 11, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4283351Abstract: The present invention provides novel 19,20-didehydro-13,14-dihydro-PG.sub.2 amides, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: August 11, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4281191Abstract: The present invention provides novel 19-hydroxy-19-methyl-PG amides and methods for their preparation and pharmacological uses for the induction of prostaglandin-like effects.Type: GrantFiled: March 24, 1980Date of Patent: July 28, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4278815Abstract: The present invention provides novel 19-keto-PG amides, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.Type: GrantFiled: March 20, 1980Date of Patent: July 14, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4277473Abstract: Compounds having the formula ##STR1## wherein a is 0 or 1, R.sub.1 is hydrogen or lower alkyl, A is lower alkylene or lower alkylidene, and R.sub.2 and R.sub.3, which can be the same or different, are hydrogen, lower alkyl, cycloalkyl, benzyl or substituted benzyl, or ##STR2## is a saturated heterocyclic ring, and acid addition salts thereof, possess anti-viral activity and reduced activity on the central nervous system.Type: GrantFiled: December 12, 1979Date of Patent: July 7, 1981Assignees: Kao Soap Co., Ltd., Sumitomo Chemical Industries Ltd.Inventors: Yoshiaki Inamoto, Motoyoshi Osugi, Eiji Kashihara
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Patent number: 4274862Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a methyl group, a methoxy group or a chlorine atom, R.sub.1 is a C.sub.2 -C.sub.7 alkyl group or a C.sub.5 -C.sub.7 cycloalkyl group and R.sub.2 is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group or a methoxy group, or when R.sub.1 and R.sub.2 are taken together, they represent a C.sub.4 -C.sub.6 alkylene group, provided that when R.sub.1 is a tertiary alkyl group, R.sub.2 does not represent a halogen atom, herbicidal compositions containing the above-mentioned compounds and methods for controlling weeds utilizing the same.Type: GrantFiled: November 7, 1979Date of Patent: June 23, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Osamu Kirino, Shunichi Hashimoto, Hiroshi Matsumoto, Hiromichi Oshio
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Patent number: 4269779Abstract: The present invention provides novel 19-hydroxy-19-methyl-6-oxo-PGF.sub.1 amides which are useful for pharmacological purposes, e.g., anti-asthmatic indications.Type: GrantFiled: March 3, 1980Date of Patent: May 26, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4268669Abstract: The present invention particularly relates to novel 9-deoxy-9-methylene-5,6-didehydro-PGF.sub.1 amides and methods for their preparation in pharmacological use.Type: GrantFiled: January 28, 1980Date of Patent: May 19, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4264523Abstract: The present invention provides novel 19,20-didehydro-13,14-dihydro-PG.sub.1 amides, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: April 28, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4264524Abstract: The present invention provides novel 19,20-didehydro-PG.sub.1 amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 17, 1979Date of Patent: April 28, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4264522Abstract: The present invention provides novel 19-hydroxy-PG amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.Type: GrantFiled: October 26, 1979Date of Patent: April 28, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4252804Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.Type: GrantFiled: January 13, 1978Date of Patent: February 24, 1981Assignee: Metabio-JoullieInventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
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Patent number: 4248859Abstract: Alkyl-substituted alicyclic carboxylic acids, esters and amides are disclosed having the property of stimulating the cold receptors of the nervous system of the human body to produce a cold sensation and are used for this purpose in a variety of edible and topical preparations.Type: GrantFiled: December 9, 1974Date of Patent: February 3, 1981Assignee: Wilkinson Sword LimitedInventors: David G. Rowsell, David J. Spring, Roger Hems
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Patent number: 4246197Abstract: Prostaglandin E (PGE)-type derivatives and analogs having a 6-keto feature are disclosed, including processes for preparing them and the appropriate intermediates, said derivatives having pharmacological activity.Type: GrantFiled: August 27, 1979Date of Patent: January 20, 1981Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4243611Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.Type: GrantFiled: April 2, 1979Date of Patent: January 6, 1981Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: RE30837Abstract: 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: September 24, 1980Date of Patent: December 29, 1981Assignee: The Upjohn CompanyInventor: Jacob Szmuszkovicz