Two Of The Cyclos Share At Least Three Ring Member (i.e., Bridged) Patents (Class 546/63)
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Patent number: 4879299Abstract: Compounds of Formula (I)S--(CH2)n--Atm (I)in whichS is a 17-spartein nucleus,n is 0 or 1, andA is 2-furyl, 2-thienyl or 2-(N-loweralkyl)pyrrylwhen n=0, or3-furyl or 3-thienyl when n=1, or pyridyl, or a phenyl group of Formula (II) ##STR1## in which at least one of R.sub.1, R.sub.2 and R.sub.3 is a defined substituent other than hydrogen. Such compounds and corresponding compounds in which A is an unsubstituted phenyl group are useful in pharmaceutical compositions as heart affecting agents. Methods of preparing such compounds and pharmaceutical compositions are disclosed. Also described is the use of such compounds or compositions, particularly compounds or compositions with positive inotropic activity, to treat various heart conditions.Type: GrantFiled: December 18, 1987Date of Patent: November 7, 1989Assignee: Kali-Chemie Pharma GmbHInventors: Uwe Schoen, Wolfgang Kehrbach, Bernd Hachmeister, Gerd Buschmann, Ulrich G. Kuehl
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Patent number: 4841045Abstract: A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.Type: GrantFiled: May 18, 1987Date of Patent: June 20, 1989Assignee: University of Vermont & State Agricultural CollegeInventor: Martin Kuehne
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Patent number: 4810708Abstract: Novel polycyclic quinoline, naphthyridine and pyrazinopyridine derivatives are disclosed which are useful for treating allergic reactions, inflammation, peptic ulcers, hypertension, and hyperproliferative skin diseases and for suppressing the immune response in mammals. Methods for preparing said compounds are also disclosed.Type: GrantFiled: February 17, 1987Date of Patent: March 7, 1989Assignee: Schering CorporationInventors: Ashit K. Ganguly, Richard J. Friary, John H. Schwerdt, Marvin I. Siegel, Sidney R. Smith, Vera A. Seidl, Edmund J. Sybertz
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Patent number: 4755520Abstract: Compounds of Formula (I)S--(CH.sub.2).sub.n --A (I)in whichS is a 17-spartein nucleusn is 0 or 1and A is 2-furyl, 2-thienyl or 2-(N-alkyl)pyrryl when n=0, or 3-furyl or 3-thienyl when n=1, or pyridyl or a phenyl group of Formula (II) ##STR1## in which at least one of R.sub.1, R.sub.2 and R.sub.3 is a defined substituent other than hydrogen. Such compounds and corresponding compounds in which A is an unsubstituted phenyl group are useful in pharmaceutical compositions as heart affecting agents. Methods of preparing such compounds and pharmaceutical compositions are also disclosed.Type: GrantFiled: June 17, 1986Date of Patent: July 5, 1988Assignee: Kali-Chemie Pharma GmbHInventors: Uwe Schon, Wolfgang Kehrbach, Bernd Hachmeister, Gerd Buschmann, Ulrich G. Kuhl
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Patent number: 4668685Abstract: Substituted benzoate ester prodrug derivatives of 3-hydroxymorphinans are useful as analgesics or narcotic antagonists and provide enhanced bioavailability of 3-hydroxymorphinans from orally administered doses.Type: GrantFiled: May 14, 1985Date of Patent: May 26, 1987Assignee: E.I. Du Pont de Nemours and CompanyInventor: Elie G. Shami
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Patent number: 4638068Abstract: There are provided novel 2-(2-imidazolin-2-yl)pyridine and quinoline compounds, a process and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: May 25, 1982Date of Patent: January 20, 1987Assignee: American Cyanamid CompanyInventor: Marinus Los
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Patent number: 4628057Abstract: Novel tetrahydro-.beta.-carboline derivatives of the formula: ##STR1## wherein R.sup.1 is carboxyl, a lower alkoxycarbonyl, carbamoyl, an N,N-di-lower alkylcarbamoyl, an N-(phenyl-substituted lower alkylidenamino)carbamoyl, a [N,N-di(lower alkyl)amino]-lower alkyl, or a nitrogen-containing monocyclic heterocyclic group;R.sup.2 is hydrogen atom, a lower alkyl, or a hydroxy-lower alkyl group, or R.sup.2 is combined with R.sup.1 to form a group: --CO--O--CH.sub.2 --;R.sup.3 is hydrogen atom, a lower alkyl, a phenyl-lower alkyl, or a group: --CSS--R.sup.4 ;R.sup.4 is hydrogen atom, an alkyl, or a group: --(CH.sub.2).sub.n Y.sup.1 ;n is 0, 1 or 2,Y.sup.Type: GrantFiled: October 30, 1984Date of Patent: December 9, 1986Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Ikuo Iijima, Yutaka Saiga, Toshikazu Miyagishima, Yuzo Matsuoka, Mamoru Matsumoto
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Patent number: 4599341Abstract: Novel substituted and bridged pyridine compounds useful as calcium channel blockers, pharmaceutical compositions thereof, and methods of treatment are disclosed.Type: GrantFiled: October 1, 1984Date of Patent: July 8, 1986Assignee: Merck & Co., Inc.Inventors: Wasyl Halczenko, George D. Hartman
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Patent number: 4587253Abstract: Novel substituted and bridged pyridine compounds useful as calcium channel blockers and analgesics, pharmaceutical compositions thereof, and methods of treatment are disclosed.Type: GrantFiled: July 30, 1984Date of Patent: May 6, 1986Assignee: Merck & Co., Inc.Inventors: Wasyl Halczenko, George D. Hartman
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Patent number: 4451468Abstract: Acidiferous salts of 17-.beta.-n-pentyl sparteine are crystallized out of a solution of 17-.beta.-n-pentyl sparteine and a dicarboxylic acid selected from the group consisting of tartaric acid, fumaric acid or mixtures thereof. The novel acidiferous pentyl sparteine salts are employed in pharmaceutical compositions for the treatment of cardiac disorders and in venous therapeutical applications, and process improved stability and pharmacological properties.Type: GrantFiled: September 30, 1981Date of Patent: May 29, 1984Assignee: Kali-Chemie Pharma GmbHInventors: Bernd Hachmeister, Wolfgang Milkowski, Ulrich Kuhl, Gerd Buschmann, Renke Budden
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Patent number: 4296238Abstract: 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, 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.Type: GrantFiled: May 7, 1980Date of Patent: October 20, 1981Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4281130Abstract: Compounds of tropane (8-azabicyclo[3.2.1]octane) series having an aromatic substituent in the 2-position and a carboalkoxy group in the 3-position are prepared by reacting a tropane-3-carboxylate having a double bond in the 2,3-position with an aryl Grignard reagent. Transformations of the substituent on nitrogen are subsequently effected. Compounds where the 3-carboalkoxy group is in the exo configuration possess hypoglycemic activity, and those where the 3-carboalkoxy group is in the endo configuration possess narcotic antagonist activity.Type: GrantFiled: October 26, 1979Date of Patent: July 28, 1981Assignee: Sterling Drug Inc.Inventors: Robert L. Clarke, Sol J. Daum
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Patent number: 4256889Abstract: Benzocycloheptapyridines with an imine bridge in the cycloheptane ring, derivatives and pharmaceutically acceptable salts thereof are useful as anxiolytics, antidepressants, anticonvulsants, muscle relaxants and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease. They are prepared, for example, by treatment of a benzo[5,6]cyclohepta[1,2-c]pyridin-11-one with ammonia to give the 11-imine, acylation of the imine, treatment of the protected imine with an alkyllithium to provide the 11-alkyl-11-acylamino compound, treatment with acid or base to cause ring closure to an 11-alkyl-6,11-acylimino compound followed by removal of the protecting group, either hydrolytically or hydrogenolytically.Type: GrantFiled: November 13, 1979Date of Patent: March 17, 1981Assignee: Merck & Co., Inc.Inventors: Kenneth L. Shepard, Daniel G. Brenner
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Patent number: 4255579Abstract: 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, 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.Type: GrantFiled: February 5, 1979Date of Patent: March 10, 1981Assignee: Sterling Drug Inc.Inventor: William F. Michne
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Patent number: 4252810Abstract: 9,10-Dihydro-4H-benzo[4,5]cyclohepta [1,2-b]thiophen-4,9-imines, derivatives and pharmaceutically acceptable salts thereof are useful as antianxiety agents, as muscle relaxants and in the treatment of extrapyramidal disorders such as in Parkinson's disease.Type: GrantFiled: November 15, 1978Date of Patent: February 24, 1981Assignee: Merck & Co., Inc.Inventors: Paul S. Anderson, Ben E. Evans
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Patent number: 4246413Abstract: Substituted 6-oxamorphinans and 6-oxaisomorphinans have been found to possess potent analgetic, narcotic antagonist, antitussive and/or ADH inhibitory activity. The compounds are prepared by total synthesis and are not derived from opium alkaloids.Type: GrantFiled: May 14, 1979Date of Patent: January 20, 1981Assignee: Bristol-Myers CompanyInventors: Thomas A. Montzka, John D. Matiskella, Richard A. Partyka
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Patent number: 4237295Abstract: Disclosed is the preparation of 17-hydroxysparteine by means of the oxidation of sparteine with permanganate in an aqueous acid solution. The oxidation is highly selective and produces the 17-hydroxysparteine in a high yield of more than 90%. The oxidizing agent may be readily separated from the reaction mixture after the reaction in the form of insoluble manganese ammonium phosphate.Type: GrantFiled: June 1, 1979Date of Patent: December 2, 1980Assignee: Kali-Chemie Pharma GmbHInventor: Bernd Hachmeister
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Patent number: 4232026Abstract: Certain 2- and/or 9- phenylalkyl-5,11-dimethyl-5,11-diazaditwistane compounds bind to opiate receptor sites and have central nervous system activities exemplified by analgesia.Type: GrantFiled: July 20, 1978Date of Patent: November 4, 1980Assignee: Merck & Co., Inc.Inventor: Jan ten Broeke
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Patent number: 4229455Abstract: Benzocycloheptapyridines with an imine bridge in the cycloheptane ring, derivatives and pharmaceutically acceptable salts thereof are useful as antianxiety agents, as muscle relaxants and in the treatment of extrapyramidal disorders such as in Parkinson's disease.Type: GrantFiled: October 18, 1978Date of Patent: October 21, 1980Assignee: Merck & Co., Inc.Inventors: Kenneth L. Shepard, Wasyl Halczenko
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Patent number: 4228285Abstract: 14-Hydroxy-6-oxamorphinans and 14-hydroxy-6-oxaisomorphinans optionally substituted in the 3-, 7- and 17-positions have been found to possess potent analgetic, narcotic antagonist, antitussive and/or ADH inhibitory activity. The compounds are prepared by total synthesis and are not derived from opium alkaloids.Type: GrantFiled: February 28, 1979Date of Patent: October 14, 1980Assignee: Bristol-Myers CompanyInventors: Thomas A. Montzka, John D. Matiskella, Richard A. Partyka
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Patent number: 4214084Abstract: Compounds of the tropane (8-azabicyclo[3.2.1]octane) series having an aromatic substituent in the 2-position and a carboalkoxy group in the 3-position are prepared by reacting a tropane-3-carboxylate having a double bond in the 2,3-position with an aryl Grignard reagent. Transformations of the substituent on nitrogen are subsequently effected. Compounds where the 3-carboalkoxy group is in the exo configuration possess hypoglycemic activity, and those where the 3-carboalkoxy group is in the endo configuration possess narcotic antagonist activity.Type: GrantFiled: May 24, 1979Date of Patent: July 22, 1980Assignee: Sterling Drug Inc.Inventors: Robert L. Clarke, Sol J. Daum
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Patent number: 4201783Abstract: Substituted hexahydro benzopyrano [3,2-c] pyridines, useful as antidepressants, have the formula ##STR1## where R is hydrogen or a saturated or unsaturated, linear or branched, lower alkyl, or an aralkyl, acyl, dialkylaminoalkyl, carbonylalkyl, alkoxycarbonyl, haloalkoxycarbonyl or aryl radical; R.sub.1 is hydrogen, halogen, or lower alkoxy; R.sub.2 is hydrogen or halogen; R.sub.3 is hydrogen, halogen, lower alkyl, alkoxy nitro or amino, or forms naphthalene with R.sub.4 and the benzene ring; R.sub.4 is hydrogen, a halogen, or forms naphthalene with R.sub.3 and the benzene ring; R.sub.5 is hydrogen, lower alkyl, or aralkyl.Type: GrantFiled: June 23, 1978Date of Patent: May 6, 1980Assignee: Lipha Lyonnaise Industrielle PharmaceutiqueInventors: Philippe Briet, Jean-Jacques Berthelon, Jean-Claude Depin
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Patent number: 4179567Abstract: Compounds of the tropane (8-azabicyclo[3.2.1]octane) series having an aromatic substiutent in the 2-position and a carboalkoxy group in the 3-position are prepared by reacting a tropane-3-carboxylate having a double bond in the 2,3-position with an aryl Grignard reagent. Transformations of the substituent on nitrogen are subsequently effected. Compounds where the 3-carboalkoxy group is in the exo configuration possess hypoglycemic activity, and those where the 3-carboalkoxy group is in the endo configuration possess narcotic antagonist activity.Type: GrantFiled: April 10, 1978Date of Patent: December 18, 1979Assignee: Sterling Drug Inc.Inventors: Robert L. Clarke, Sol J. Daum
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Patent number: 4179565Abstract: 2,5-Dimethyl-benzo[b]thieno[2,3-f]morphan and the precursors thereof, 2-(3-benzo[b]thienylmethyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine and 2-(3-benzo[b]-thienylmethyl)-1,4-dimethyl-1,2,5,6-tetrahydropyridine, useful as analgesic agents, are disclosed.Type: GrantFiled: January 23, 1978Date of Patent: December 18, 1979Assignee: Laboratorios Made, S.A.Inventors: Ricardo Granados Jarque, Mercedes Alvarez Domingo, Juan Bosch Cartes, Cristobal Martinez Roldan, Fernando Rabadan Peinado
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Patent number: 4178450Abstract: 2,5-dimethyl-benzo [b] thiene [3,2-f] morphan and 2-(2-benzo [b] thienyl-methyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine or their pharmacologically acceptable acid addition salts are useful as analgesic agents.Type: GrantFiled: February 1, 1978Date of Patent: December 11, 1979Assignee: Laboratories Made, S. A.Inventors: Ricardo Granados Jarque, Mercedes Alvarez Domingo, Juan Bosch Cartes, Cristobal Martinez Roldan, Fernando Rabadan Peinado
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Patent number: 4172201Abstract: Alpha-2,5,9-trimethyl-benzo [b]thiene [2,3-f]morphan and 2-(3-benzo[b]thienylmethyl)-1,3,4-trimethyl-1,2,5,6-tetrahydropyridine or their pharmacologically acceptable acid addition salts are useful as analgesic agents.Type: GrantFiled: February 2, 1978Date of Patent: October 23, 1979Assignee: Laboratorios Made, S.A.Inventors: Ricardo G. Jarque, Mercedes A. Domingo, Juan B. Cartes, Cristobal M. Roldan, Fernando R. Peinado
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Patent number: 4166174Abstract: Benzazocine derivatives represented by the formula ##STR1## which have an excellent analgesic action and are useful for use in drugs, and a process for preparing the same are disclosed.Type: GrantFiled: June 13, 1977Date of Patent: August 28, 1979Assignee: Chugai Seiyaku Kabushiki KaishaInventors: Sadao Tanaka, Morio Kakimoto, Yugo Ikeda
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Patent number: 4154932Abstract: N-substituted 6-oxamorphinans have been found to possess potent analgetic, narcotic antagonist, antitussive, and ADH inhibitory activity. A particularly preferred compound is (-)-17-cyclopropylmethyl-3-hydroxy-6-oxamorphinan. The compounds are prepared by total synthesis and are not derived from opium alkaloids.Type: GrantFiled: September 8, 1977Date of Patent: May 15, 1979Assignee: Bristol-Myers CompanyInventors: Thomas A. Montzka, John D. Matiskella, Richard A. Partyka
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Patent number: 4132710Abstract: [2]Benzopyrano[3,4-c]pyridine derivatives characterized by having a 2,3,4,4a,6,10b-hexahydro-1H-[2]benzopyrano[3,4-c]pyridine nucleus bearing a substituent at position 6 are disclosed. The nucleus can be optionally further substituted at positions 2,3,4,6 and on the aromatic ring. The derivatives are useful diuretic, anorexic, antidepressant, anticonvulsant and antihypertensive agents. Methods for their preparation and use also are disclosed.Type: GrantFiled: December 20, 1976Date of Patent: January 2, 1979Assignee: Ayerst, McKenna and Harrison, Ltd.Inventors: Jean A. Gauthier, Leslie G. Humber, Clara Revesz