Five-membered Ring In Substituent Q Patents (Class 564/189)
  • Patent number: 4338316
    Abstract: 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: Grant
    Filed: September 26, 1979
    Date of Patent: July 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Peter R. Marsham
  • Patent number: 4337268
    Abstract: 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: Grant
    Filed: May 15, 1980
    Date of Patent: June 29, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Wilhelm Brandes
  • Patent number: 4329363
    Abstract: 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: Grant
    Filed: January 16, 1980
    Date of Patent: May 11, 1982
    Assignee: Merck & Co., Inc.
    Inventors: Conrad P. Dorn, Howard Jones
  • Patent number: 4327111
    Abstract: 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: Grant
    Filed: July 14, 1980
    Date of Patent: April 27, 1982
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, Tamara Dejneka
  • Patent number: 4324730
    Abstract: 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: Grant
    Filed: October 8, 1980
    Date of Patent: April 13, 1982
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4322553
    Abstract: 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: Grant
    Filed: February 2, 1981
    Date of Patent: March 30, 1982
    Assignee: Monsanto Company
    Inventor: John P. Chupp
  • Patent number: 4315031
    Abstract: 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: Grant
    Filed: August 28, 1978
    Date of Patent: February 9, 1982
    Assignee: Science Union et Cie
    Inventors: Michel Vincent, Georges Remond, Jacques Bure
  • Patent number: 4313005
    Abstract: 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: Grant
    Filed: April 3, 1980
    Date of Patent: January 26, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Randall J. Daughenbaugh
  • Patent number: 4312997
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: January 26, 1982
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4311858
    Abstract: 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: Grant
    Filed: December 1, 1980
    Date of Patent: January 19, 1982
    Assignee: Monsanto Company
    Inventor: John P. Chupp
  • Patent number: 4309433
    Abstract: 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: Grant
    Filed: June 30, 1980
    Date of Patent: January 5, 1982
    Assignee: Shionogi & Co., Ltd.
    Inventors: Kentaro Hirai, Teruyuki Ishiba, Shigeru Matsutani, Itsuo Makino, Toshio Fujishita, Masami Doteuchi, Koichi Otani
  • Patent number: 4309424
    Abstract: 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: Grant
    Filed: November 5, 1979
    Date of Patent: January 5, 1982
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventors: Lawrence L. Martin, Manfred Worm, Charles A. Crichlow
  • Patent number: 4307112
    Abstract: 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: Grant
    Filed: February 26, 1980
    Date of Patent: December 22, 1981
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Carlo Passarotti, William Fava, Angelo Fumagalli, Franco Faustini, Roberto Ceserani
  • Patent number: 4304733
    Abstract: 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: Grant
    Filed: April 17, 1980
    Date of Patent: December 8, 1981
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4301083
    Abstract: 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: Grant
    Filed: January 2, 1980
    Date of Patent: November 17, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Noriaki Yoshimura, Masuhiko Tamura
  • Patent number: 4289770
    Abstract: 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: Grant
    Filed: June 13, 1980
    Date of Patent: September 15, 1981
    Assignee: Pierre Fabre S.A.
    Inventors: Henri Cousse, Gilbert Mouzin
  • Patent number: 4283350
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: August 11, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4283351
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: August 11, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4281191
    Abstract: 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: Grant
    Filed: March 24, 1980
    Date of Patent: July 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4278815
    Abstract: The present invention provides novel 19-keto-PG amides, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: July 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4277473
    Abstract: 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: Grant
    Filed: December 12, 1979
    Date of Patent: July 7, 1981
    Assignees: Kao Soap Co., Ltd., Sumitomo Chemical Industries Ltd.
    Inventors: Yoshiaki Inamoto, Motoyoshi Osugi, Eiji Kashihara
  • Patent number: 4274862
    Abstract: 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: Grant
    Filed: November 7, 1979
    Date of Patent: June 23, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Osamu Kirino, Shunichi Hashimoto, Hiroshi Matsumoto, Hiromichi Oshio
  • Patent number: 4269779
    Abstract: 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: Grant
    Filed: March 3, 1980
    Date of Patent: May 26, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4268669
    Abstract: 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: Grant
    Filed: January 28, 1980
    Date of Patent: May 19, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4264523
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: April 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4264524
    Abstract: 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: Grant
    Filed: October 17, 1979
    Date of Patent: April 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4264522
    Abstract: The present invention provides novel 19-hydroxy-PG amides methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: April 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4252804
    Abstract: 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: Grant
    Filed: January 13, 1978
    Date of Patent: February 24, 1981
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
  • Patent number: 4248859
    Abstract: 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: Grant
    Filed: December 9, 1974
    Date of Patent: February 3, 1981
    Assignee: Wilkinson Sword Limited
    Inventors: David G. Rowsell, David J. Spring, Roger Hems
  • Patent number: 4246197
    Abstract: 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: Grant
    Filed: August 27, 1979
    Date of Patent: January 20, 1981
    Assignee: The Upjohn Company
    Inventor: Udo F. Axen
  • Patent number: 4243611
    Abstract: 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: Grant
    Filed: April 2, 1979
    Date of Patent: January 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: RE30837
    Abstract: 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: Grant
    Filed: September 24, 1980
    Date of Patent: December 29, 1981
    Assignee: The Upjohn Company
    Inventor: Jacob Szmuszkovicz