The Additional Six-membered Hetero Ring Is One Of The Cyclos In A Polycyclo Ring System Patents (Class 544/125)
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Patent number: 4791108Abstract: Compounds of formulas (1) and (2): ##STR1## in which: X and Y are independently hydrogen, hydroxy, lower alkyl, lower alkoxy or halo, or X and Y taken together is methylenendioxy or ethylene-1,2-dioxy, andR is lower alkyl, optionally substituted phenyl, --(CH.sub.2).sub.m OR.sup.1 or --NR.sup.1 R.sup.2 wherein m is an integer of 1 to 6 and R.sup.1 and R.sup.2 are independently hydrogen or lower alkyl, or --NR.sup.1 R.sup.2 taken together is a heterocycle of the formula: ##STR2## wherein A is --CH.sub.2 --, --NR.sup.1 -- or oxygen, or a pharmaceutically acceptable salt thereof, are useful as .alpha..sub.2 -blockers, especially as antidepressants.Type: GrantFiled: April 13, 1987Date of Patent: December 13, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: Robin D. Clark
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Patent number: 4786729Abstract: Benzimidazolo-quinazolines of the general formula ##STR1## in which Y denotes a radical of the formula ##STR2## Y.sub.1 denotes hydrogen or alkyl, X and X.sub.1, independently of one another, denote hydrogen, alkyl, cycloalkyl, aryl or aralkyl, orX and X.sub.1, together with the nitrogen atom connecting them, denote a 5- or 6-membered ring,X.sub.2 denotes hydrogen, halogen, alkyl, alkoxy or alkoxycarbonyl,X.sub.3 denotes hydrogen, alkyl or aryl,X.sub.4 denotes hydrogen, cyano, halogen, alkyl or alkoxy,Z denotes hydrogen, alkyl, cycloalkyl or aralkyl,D denotes an optionally hydrogenated 5- or 6-membered ring, andm and n, independently of one another, denote 0 or 1,in which a double bond is in the positions labelled with 1 and 2 when m=0 and a single bond is in these positions when m=1, andin which the rings A, B and D are the radicals X, X.sub.1, X.sub.2, X.sub.3, X.sub.Type: GrantFiled: April 3, 1987Date of Patent: November 22, 1988Assignee: Bayer AktiengesellschaftInventors: Holger Heidenreich, Gert Jabs
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Patent number: 4782052Abstract: The invention relates to new 1,2,3,4,6,7,12,12b-octahydroindolo[2,3,-a]quinolizin-1-yl-alkanecarboxylic acid amides of the formula (I), ##STR1## wherein R.sub.1 and R.sub.2 stand independently for a hydrogen or halogen atom, or a hydroxyl, nitro or C.sub.1-4 alkoxy group;R.sub.3 and R.sub.4 stand independently for a hydrogen atom or a C.sub.1-4 alkyl group;R.sub.5 and R.sub.6 stand independently for a hydrogen atom, C.sub.1-8 alkyl group, C.sub.3-8 alkenyl or cycloalkyl group, aryl or aralkyl group, heteroaryl or heteroaralkyl group containing oxygen, nitrogen or sulphur atom, all these groups being optionally substituted; orR.sub.5 and R.sub.6 together form an optionally substituted C.sub.2-8 .alpha.,.omega.-alkylene group, wherein one carbon atom may optionally be replaced by an oxygen or nitrogen atom; andG means a C.sub.1-4 straight chained alkylene group, as well as to their therapeutically suitable acid addition salts and pharmaceutical compositions containing these compounds.Type: GrantFiled: October 3, 1985Date of Patent: November 1, 1988Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Ferenc Soti, Csaba Szantay, Maria Incze, Zsuzsanna Balogh nee Kardos, Elemer Ezer, Judit Matuz, Laszlo Szporny, Gyorgy Hajos, Csaba Kuthi
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Patent number: 4735943Abstract: There is disclosed novel eburnamonine oxime, its derivatives and salts, process for the manufacture thereof and pharmaceutical agents containing the same. The compounds are represented by the following formula. ##STR1## wherein R is hydrogen, alkyl, alkoxyalkyl, or oxisilanylalkyl group or a group of ##STR2## R.sup.1 and R.sup.2 are same or different and respectively hydrogen, alkyl having 1 to 4 carbon atoms, aryl or aralkyl group, or R.sup.1 represents together with R.sup.2 and the neighboring nitrogen atom a non-substituted or substituted heterocyclic ring, and n is an integer of 2 or 3.Type: GrantFiled: June 3, 1985Date of Patent: April 5, 1988Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Masatoshi Ban, Yutaka Baba, Kiichi Sawai
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Patent number: 4732897Abstract: The present invention relates to new 4-aza-17.beta.-substituted 5.alpha.-androstan-3-ones, to a process for their preparation, to pharmacological compostions containing them, and to the use of said compounds as inhibitors of androgen action by means of testosterone 5-reductase inhibition.Type: GrantFiled: February 3, 1986Date of Patent: March 22, 1988Assignees: Farmitalia Carlo Erba, S.p.A., Consiglio Nazionale Delle RicercheInventors: Gianfranco Cainelli, Giorgio Martelli, Mauro Panunzio, Giuseppe Spunta, Giuliano Nannini, Enrico di Salle
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Patent number: 4728647Abstract: Compounds of formula: ##STR1## in which V and W are H, halogen, alkyl (1-4C) or alkoxy (1-4C), amino, or acylamino,Z is phenyl, optionally substituted, thienyl, or pyridyl,R.sub.1 is alkyl (1-6C), alkoxyalkyl, cycloalkyl (3-6C), phenyl, phenylalkyl, or cycloalkylalkyl,R.sub.2 is alkyl (1-6C), alkoxyalkyl, cycloalkyl (3-6C), phenyl, phenylalkyl, cycloalkylalkyl, or morpholino, andNR.sub.1 R.sub.2 can also be pyrrolidino, optionally substituted piperidino, optionally substituted morpholino, thiomorpholino, optionally substituted piperazino, or an optionally substituted piperazinone, are useful as anxiolytic agents.Type: GrantFiled: May 28, 1986Date of Patent: March 1, 1988Assignee: Rhone-Poulenc SanteInventors: Jesus Benavides, Marie-Christine Dubroeucq, Gerard Le Fur, Christian Renault
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Patent number: 4716162Abstract: Fused ring compounds of formula (I): ##STR1## (where R.sup.1 -R.sup.4, X.sup.1 and X.sup.2 represent hydrogen or various substituents, n and m are 1-3 and 2-7 respectively, the dotted lines are double or single bonds and Y is one oxygen or two hydrogens) have magnificent anti-arrhythmic activity, diuretic activity and the ability to improve brain function.Type: GrantFiled: July 16, 1985Date of Patent: December 29, 1987Assignee: Sankyo Company, LimitedInventors: Kuniyuki Tomita, Yasuo Shimoji, Seiji Kumakura, Hiroyuki Koike, Nobuyoshi Iwata, Yasuhiro Morisawa
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Patent number: 4709029Abstract: Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R-NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.Type: GrantFiled: January 23, 1986Date of Patent: November 24, 1987Assignee: Hoechst AktiengesellschaftInventors: Ernst Spietschka, Helmut Troster
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Patent number: 4690928Abstract: Substituted hexahydro arylquinolizines and pharmaceutically acceptable salts thereof are selective .alpha..sub.6 -adrenergic receptor antagonists and thereby useful as antidepressants, antihypertensives, antidiabetics, antiobesity and platelet aggregation inhibitors.Type: GrantFiled: July 14, 1986Date of Patent: September 1, 1987Assignee: Merck & Co., Inc.Inventors: Joel R. Huff, Joseph P. Vacca, John J. Baldwin
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Patent number: 4675323Abstract: Compounds which are imidazo[1,2-a]quinoline derivatives of general formula (I) ##STR1## in which X is hydrogen, halogen, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, (C.sub.1-4) alkylthio, methylsulphonyl, amino, (C.sub.1-4)alkylamino, di-(C.sub.1-4)alkylamino, nitro or trifluoromethyl, Y is hydrogen, halogen or methyl in position 6, 7 or 8, R.sub.1 and R.sub.2, which may be the same or different, are hydrogen or (C.sub.1-6) alkyl, or R.sub.1 and R.sub.2 together form a tetramethylene, pentamethylene, 3-methyl-3-azapentamethylene, 3-ethoxycarbonyl-3-azapentamethylene group, and A and B both are hydrogen or together form a carbon-carbon bond, and their pharmacologically acceptable acid addition salts have anxiolytic, sleep-inducing, hypnotic, anticonvulsant, analgesic and anti-ulcer properties.Type: GrantFiled: February 7, 1986Date of Patent: June 23, 1987Assignee: SynthelaboInventors: Pascal George, Danielle De Peretti
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Patent number: 4642373Abstract: 1,2,3,4,4a,4b,5,6,7,8,8a,12b-Dodecahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy or alkoxyalkyl)triphenylenes, 2,3,3a,3b,4,5,6,7,7a,11b-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)-1H-cyclopenta[1]-phenanthrenes, 2,3,4,4a,4b,5,6,7,8,8a-decahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl)-1H-pyrido[1,2-f]phenanthridines, and 1,2,3,3a,3b,4,5,6,7,7a-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)pyrrolo[1,2-f]phenanthridines and derivatives are valuable as central nervous system active agents or as intermediates to compounds having such activity.Type: GrantFiled: July 6, 1984Date of Patent: February 10, 1987Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4623380Abstract: Compounds of the formula ##STR1## in which A denotes C-R.sup.4 or N; X denotes alkyl and Y denotes alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzoyl, or, together with X, cycloalkyl; R.sup.1 -R.sup.4 denote H, alkyl, alkoxy, alkoxycarbonyl, halogen, NO.sub.2, CN, phenoxy or (substituted) phenyl; R.sup.5 denotes H or alkyl; and R.sup.6 denotes H, (substituted) alkyl, halogenoalkenyl, cycloalk(en)yl, alkynyl, (substituted) phenyl or carboxylic acid ester, carboxylic acid amide, sulfo-ester or acyl radicals, are effective plant treatment agents, in particular herbicides.Type: GrantFiled: February 1, 1985Date of Patent: November 18, 1986Assignee: Hoechst AktiengesellschaftInventors: Roland Schmierer, Reinhard Handte, Hilmar Mildenberger, Klaus Bauer, Hermann Bieringer, Helmut Burstell
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Patent number: 4608379Abstract: Compounds containing a cation of formula Ia ##STR1## and a pharmaceutically acceptable anion are anti-fungal agents. In formula Ia and Ib R.sub.1 is alkyl of at least 3 carbon atoms or aralkyl; R.sub.2 and R.sub.5 are hydrogen, lower alkyl, lower alkoxy, halogen or nitro; R.sub.6 and R.sub.7, when separate, are lower alkyl or aryl(lower)alkyl or, when joined together, are --(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 -- (where A is --(CH.sub.2).sub.n --, O, S or NR.sub.8 where n is O, 1 or 2 and R.sub.8 is lower alkyl) or a mono- or di-(lower alkyl) substitution product thereof.Type: GrantFiled: September 5, 1984Date of Patent: August 26, 1986Assignee: John Wyeth & Brother LimitedInventor: John T. A. Boyle
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Patent number: 4604463Abstract: New camptothecin derivatives possessing high anti-tumor activity with slight toxicity, represented by the general formula: ##STR1## wherein R.sup.1 is a hydrogen atom, a halogen atom or an alkyl group with 1-4 carbon atoms and X is a chlorine atom or --NR.sup.2 R.sup.3 where R.sup.2 and R.sup.3 are the same or different and each represents a hydrogen atom, a substituted or unsubstituted alkyl group with 1-4 carbon atoms or a substituted or unsubstituted carbocyclic or heterocyclic group, with the proviso that when both R.sup.2 and R.sup.3 are the substituted or unsubstituted alkyl groups, they may be combined together with the nitrogen atom, to which they are bonded, to form a heterocyclic ring which may be interrupted with --O--, --S-- and/or >N--R.sup.4 in which R.sup.Type: GrantFiled: July 5, 1984Date of Patent: August 5, 1986Assignee: Kabushiki Kaisha Yakult HonshaInventors: Tadashi Miyasaka, Seigo Sawada, Kenichiro Nokata, Eiichi Sugino, Masahiko Mutai
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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: 4599408Abstract: Compounds of the formula ##STR1## in which R denotes hydrogen, hydroxyl, amino or optionally substituted alkyl, X denotes chlorine or bromine and n is a number from zero to 4, are obtained from the corresponding mono-alkali metal salts of perylene-3,4,9,10-tetracarboxylic acid monoanhydrides by reaction with compounds of the formula R--NH.sub.2, in which R has the above meaning, at 0.degree.-130.degree. C. The compounds are colorants or starting materials for colorants.Type: GrantFiled: April 11, 1984Date of Patent: July 8, 1986Assignee: Hoechst AktiengesellschaftInventors: Ernst Spietschka, Helmut Troster
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Patent number: 4591587Abstract: Novel cyclopropyl pyridine compounds useful as calcium channel blockers, pharmaceutical compositions thereof, and methods of treatment are disclosed.Type: GrantFiled: October 1, 1984Date of Patent: May 27, 1986Assignee: Merck & Co., Inc.Inventor: David C. Remy
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Patent number: 4590276Abstract: A novel process for the preparation of cyclopropyl pyridine compounds, which are useful as calcium channel blockers, is disclosed.Type: GrantFiled: October 1, 1984Date of Patent: May 20, 1986Assignee: Merck & Co., Inc.Inventor: Stella W. King
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Patent number: 4588525Abstract: Prodrug compounds for dermal application of topical medicaments, such as 6-aminonicotinamide for treatment of psoriasis, are linked by an enzyme cleavable group to a carrier side chain, such as succinyl piperidate or morpholidate. The neutral lipophilic compounds are rapidly absorbed into the epithelial cells where they are enzymatically cleaved to release the active drug in an ionic form which is retained within the cells.Type: GrantFiled: February 27, 1984Date of Patent: May 13, 1986Assignee: Molecular Biosystems, Inc.Inventors: Lyle J. Arnold, Jr., Jerome A. Streifel
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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: 4554274Abstract: New quaternary derivatives of 10-bromoajmaline and 10-bromoisoajmaline are disclosed which exhibit antiarrhythmic and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup.- represents an acid anion as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.Type: GrantFiled: May 31, 1984Date of Patent: November 19, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Wolfgang Kehrbach, Joachim Wegener, Ulrich Kuehl, Renke Budden, Gerd Buschmann
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Patent number: 4552877Abstract: New N.sub.b -quaternary 10-bromosandwicine and 10-bromoisosandwicine derivatives are disclosed which exhibit antiarrhythmic properties and adrenolytic properties and which have the formula I ##STR1## wherein R represents a carbon-attached organic group containing 1 to 10 carbon atoms and A.sup..crclbar. represents an acid anion, as well as pharmaceutical formulations thereof and processes and intermediates for their preparation.Type: GrantFiled: May 31, 1984Date of Patent: November 12, 1985Assignee: Kali-Chemie Pharma GmbHInventors: Wolfgang Kehrbach, Joachim Wegener, Ulrich Kuehl, Renke Budden, Gerd Buschmann
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Patent number: 4496570Abstract: Compounds the structural formula ##STR1## or their pharmaceutically acceptable salts, wherein X is H or CH.sub.3, Z is NH.sub.2 or OR.sub.6, R.sub.1 is a C.sub.1-8 alkyl, C.sub.3-6 -cycloalkylmethyl, or phenyl-C.sub.1-2 alkyl group,R.sub.2 is hydrogen, hydroxy, chloro or fluoro,R.sub.3 is hydrogen, hydroxy, methoxy, --OCO--(C.sub.1-6 -alkyl) or morpholinoethoxy,R.sub.4 and R.sub.5 may be the same or different and are H or C.sub.1-6 alkyl,R.sub.6 is H, C.sub.1-4 alkyl, C.sub.3-5 alkenyl, C.sub.3-7 cycloalkyl phenyl, or phenyl substituted by one to three alkyl groups with a total of 4 carbon atoms are useful opiod antagonists.Type: GrantFiled: March 21, 1983Date of Patent: January 29, 1985Assignee: Key Pharmaceuticals, Inc.Inventor: Nicholas S. Bodor
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Patent number: 4473704Abstract: 1,2,3,4,4a,4b,5,6,7,8,8a,12b-Dodecahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy or alkoxyalkyl)triphenylenes, 2,3,3a,3b,4,5,6,7,7a,11b-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)-1H-cyclopenta[1]phenanthrenes, 2,3,4,4a,4b,5,6,7,8,8a-decahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl)-1H-pyrido[1,2-f]phenanthridines, and 1,2,3,3a,3b,4,5,6,7,7a-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)pyrrolo[1,2-f]phenanthridines and derivatives are valuable as central nervous system active agents or as intermediates to compounds having such activity.Type: GrantFiled: March 16, 1982Date of Patent: September 25, 1984Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4440768Abstract: Pyrrolo [3,4-c]quinolines are described which have various substitutions at the 2, 4, 5, 6, 7, 8 and 9 positions. The group of compounds has been found to possess unexpected pharmaceutical utilities including antipsychotic, analgesic and antidepressant activities. Also set forth are various methods of making the compounds as well as pharmaceutical compositions containing them.Type: GrantFiled: July 8, 1982Date of Patent: April 3, 1984Assignee: ICI Americas inc.Inventor: Howard S. Shapiro
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Patent number: 4410536Abstract: The present invention relates to certain new 7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole compound, to a process for their production and to their use as agents which have an influence on the central nervous system.The ring system according to the invention has not hitherto been described in the literature.Type: GrantFiled: April 27, 1981Date of Patent: October 18, 1983Assignee: Troponwerke GmbH & Co. K.G.Inventors: Karl-Heinz Boltze, Peter-Rudolf Seidel, Haireddin Jacobi, Helmut H. Schwarz, Gunter Schollnhammer, Hans-Dieter Dell
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Patent number: 4389405Abstract: Compounds having the following general formula: ##STR1## wherein R is an alkyl or aminoalkyl group having 1 to 8 carbon atoms, or a hydrogen atom; R.sub.2 and R.sub.3 are either hydrogen atoms or, together, an additional carbon-carbon bond, as well as the mineral or organic acid addition salts thereof. These compounds are used as anti-arhythmic agents.Type: GrantFiled: January 7, 1981Date of Patent: June 21, 1983Assignee: Omnichem, S.A.Inventor: Jean A. Hannart
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Patent number: 4348391Abstract: The present invention provides compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine,R.sub.1 is methyl or ethyl,R.sub.2 is alkyl of 1 to 4 carbon atoms or allyl,R.sub.3 is CH.sub.2 CN or a group --NR.sub.4 R.sub.5, wherein R.sub.4 is hydrogen or alkyl of 1 to 4 carbon atoms, and R.sub.5 is alkanoyl of 1 to 5 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms in the aggregate thereof, or mono-, di- or tri-haloalkoxycarbonyl of 3 to 5 carbon atoms, wherein the alkoxy group is substituted by halogen other than in the .alpha. position to the oxygen atom, or R.sub.5 is SO.sub.2 R.sub.6, wherein R.sub.6 is alkyl of 1 to 4 carbon atoms, mono-, di- or tri-haloalkyl of 1 to 4 carbon atoms, phenyl, phenyl mono-substituted by halogen or alkoxy of 1 to 4 carbon atoms, or pyridyl, or R.sub.6 is a group NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms, or R.sub.7 and R.sub.8 together form --[CH.sub.2 ].sub.n -- or --[CH.sub.2 ].sub.2 --A--[CH.Type: GrantFiled: September 22, 1980Date of Patent: September 7, 1982Assignee: Sandoz Ltd.Inventors: Peter Stutz, Theodor Fehr, Paul Stadler
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Patent number: 4348392Abstract: This invention provides new compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine,R.sub.1 is methyl or ethyl, andR.sub.2 is CH.sub.2 --CN, or a group NR.sub.3 R.sub.4, whereinR.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is SO.sub.2 R.sub.5, wherein R.sub.5 is alkyl of 1 to 4 carbon atoms, mono- to tri-halogenalkyl of 1 to 4 carbon atoms, phenyl, pyridyl, phenyl monosubstituted by halogen or alkoxy of 1 to 4 carbon atoms, or a group NR.sub.6 R.sub.7, wherein each ofR.sub.6 and R.sub.7 is independently hydrogen or alkyl of 1 to 4 carbon atoms, orR.sub.6 and R.sub.7 together are one of the groups (CH.sub.2).sub.n or (CH.sub.2).sub.2 --A--(CH.sub.2).sub.2, whereinn is a number from 3 to 7, andA is oxygen, sulphur or nitrogen substituted by alkyl of 1 to 4 carbon atoms or phenyl,useful as prolactin secretion agents and antiparkinson agents.Type: GrantFiled: September 22, 1980Date of Patent: September 7, 1982Assignee: Sandoz Ltd.Inventors: Theodor Fehr, Paul Stadler, Peter Stutz
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Patent number: 4335129Abstract: Nitrogen containing heterocyclic compounds shown by the formula ##STR1## wherein Y represents an oxygen atom, a sulfur atom, or a group shown by ##STR2## (wherein m is 1 or 2); n represents 0 or 1; R.sub.1 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, a hydroxyl groups, a lower alkanoyloxy group, a lower alkyl group or a lower alkenyl group; said R.sub.2 and R.sub.3 may further form together a double bond; R.sub.5 and R.sub.6, which may be the same or different, each represents by hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, an amino group, a lower alkoxy group, a mono or di lower alkylamino group, or a lower alkyl group; said R.sub.5 and R.sub.6 may further form together a lower alkylenedioxy group; and R.sub.Type: GrantFiled: January 28, 1981Date of Patent: June 15, 1982Assignee: Yamanouchi Pharmaceutical Co. Ltd.Inventors: Kazuo Kubo, Noriki Ito, Isao Souzu, Yasuo Isomura, Hiroshige Homma
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Patent number: 4321381Abstract: Compounds and process for making same are disclosed, the compounds having the formula (I): ##STR1## wherein R.sub.1 represents methyl, phenyl, piperidino, 1-pyrrolidinyl, morpholino or 4-methyl-1-piperazinyl, alkyl or alkoxy having from 1 to 4 carbon atoms, amino, substituted amino of the formula NHR' (wherein R' is alkyl having from 1 to 4 carbon atoms, cycloalkyl, a benzyl, or phenyl) or substituted amino of the formula NR" R"' (wherein R" and R"' both represent alkyl having from 1 to 4 carbon atoms);R.sub.2 represents a hydrogen atom, alkyl having from 1 to 4 carbon atoms, or phenyl;R.sub.3 represents a fluorine atom, cyano, difluoromethyl, difluorobromomethyl, trifluoromethyl, methylthio, methylsulphonyl, sulphonamido, an alkoxy having from 1 to 4 carbon atoms, an alkanoyl having from 2 to 5 carbon atoms, or benzoyl;R.sub.4 represents a hydrocarbon having from 1 to 4 carbon atoms;R.sub.5 represents a hydrogen atom or methoxy;R.sub.6 represents a hydrogen or halogen atom or methyl; andR.sub.Type: GrantFiled: September 19, 1980Date of Patent: March 23, 1982Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Sergio Mantegani, Guiliana Arcari, Anna M. Caravaggi, Germano Bosisio
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Patent number: 4297498Abstract: A series of 2,6-diamino-4-tertiary-amino-pyridine 1-oxides is disclosed. Substituents in the 4-position include diethylamino, pyrrolidinyl, piperidino, morpholino, thiomorpholino, and N-methylpiperazino. Novel oxadiazolones such as 5-amino-7-(1-piperidinyl)-2H-[1,2,4]oxadiazolo[2,3-a]pyridine-2-one which are useful in the preparation of the pyridine 1-oxides are also disclosed. The compounds of this invention lower blood pressure in normotensive and hypertensive mammals and are particularly useful in the treatment of hypertensive conditions in mammals. 2,6-Diamino-4-(1-piperidinyl)pyridine 1-oxide is a representative embodiment of the invention.Type: GrantFiled: August 23, 1979Date of Patent: October 27, 1981Assignee: Mead Johnson & CompanyInventors: John E. Lawson, Ronald D. Dennis
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Patent number: 4263304Abstract: Novel indoloisoquinoline derivatives of the formula, ##STR1## wherein R.sub.1 and R.sub.4 are each hydrogen, a halogen, nitro or C.sub.1-4 alkoxy and R.sub.2 and R.sub.3 are each hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, a C.sub.3-6 cycloalkyl-C.sub.1-3 alkyl or a group of the formula, ##STR2## or -A-O-B wherein A is a C.sub.1 -C.sub.7 alkylene; R.sub.5 and R.sub.6 are each hydrogen or C.sub.1-4 alkyl, or, when taken together with the adjacent nitrogen atom, may form a 5- or 6-membered heterocyclic ring and B is hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl or C.sub.2-4 alkanoyl, provided that, when both R.sub.1 and R.sub.4 are hydrogen and R.sub.3 is methyl, then R.sub.2 can not be hydrogen, have potent anti-tumor activities.Type: GrantFiled: February 27, 1979Date of Patent: April 21, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Kikuo Ishizumi, Junki Katsube
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Patent number: 4252941Abstract: Compounds and process for making same are disclosed, the compounds having the formula (I): ##STR1## wherein R.sub.1 represents a methyl, phenyl, piperidino, 1-pyrrolidinyl, morpholino or 4-methyl-1-piperazinyl group, an alkyl or alkoxy group having from 1 to 4 carbon atoms, an amino group, a substituted amino group of the formula NHR' (wherein R' represents an alkyl group having from 1 to 4 carbon atoms, a cycloalkyl group, a benzyl group, or a phenyl group) or a substituted amino group of the formula NR" R"' (wherein R" and R"' both represent alkyl groups having from 1 to 4 carbon atoms);R.sub.2 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, or a phenyl group;R.sub.3 represents a fluorine atom, a cyano, difluoromethyl, difluorobromomethyl, trifluoromethyl, methylthio, methylsulphonyl, or sulphonamido group, an alkoxy group having from 1 to 4 carbon atoms, an acyl group having from 2 to 4 carbon atoms, or a benzoyl group;R.sub.Type: GrantFiled: September 4, 1979Date of Patent: February 24, 1981Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Sergio Mantegani, Giuliana Arcari, Anna M. Caravaggi, Germano Bosisio
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Patent number: 4229450Abstract: Novel ergoline derivatives are disclosed having the general formula (I) ##STR1## wherein R.sub.1 is hydrogen, and alkyl radical (C.sub.1 to C.sub.4) either straight of branched chain,Z is hydrogen, bromine, S-R.sub.IV (in which R.sub.IV is an alkyl of from C.sub.1 to C.sub.4,R.sub.II is equal to R.sub.III and is an alkyl of from C.sub.1 to C.sub.6, orR.sub.II united with R.sub.III by-(CH.sub.2).sub.n, with n from 0 to 7, to form simple heterocyclic compounds such as pyrrolidine, piperidine, hexamethyleneimine, or united with --(CH.sub.2).sub.n --A--(CH.sub.2).sub.n, with n equal to a number from 2 to 5 to form heterocyclic compounds such as A=0 and n=2 to give morpholine, A is N-R.sub.V and N=2 for piperazine, either substituted or unsubstituted, with R.sub.V being hydrogen, an alkyl of from C.sub.1 to C.sub.4, or a phenyl radical, the x--y bridge being a ##STR2## bond. A method for the preparation of such compounds and pharmaceutical compositions thereof are also disclosed.Type: GrantFiled: January 16, 1979Date of Patent: October 21, 1980Assignee: Simes Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Giorgio Ferrari, Vittorio Vecchietti
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Patent number: 4207320Abstract: Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts having the formula I: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl, C.sub.4 -C.sub.6 cycloalkyl, di(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, 4-morpholinyl or 2,2-dimethylhydrazino;R.sub.2 is hydrogen, lower alkyl, lower alkylamino, di(lower alkyl)amino, C.sub.4 -C.sub.6 cycloalkylamino, lower alkoxy(lower alkyl)amino, 1-azetidinyl, 1-pyrrolidinyl, 1-piperidinyl, methyl-1-pyrrolidinyl, methyl-1-piperidinyl, hexahydro-1H-azepin-1-yl, 4-morpholinyl, benzylamino, N-methylbenzylamino or 2-phenylethylamino;R.sub.3 is hydrogen or methyl;X is an anion;with the proviso that at least one of R.sub.1 and R.sub.2 is other than hydrogen, lower alkyl or C.sub.4 -C.sub.6 cycloalkyl; and with the further proviso that when R.sub.2 is dimethylamino, at least one of R.sub.1 and R.sub.3 is other than hydrogen, and intermediates used in the preparation thereof are disclosed.Type: GrantFiled: August 28, 1978Date of Patent: June 10, 1980Assignee: Warner-Lambert CompanyInventors: David B. Capps, Mario M. Angelo, Townley P. Culbertson
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Patent number: 4199579Abstract: A number of pharmacologically active ergoline derivatives are disclosed, their preparation is described and examples of suitable pharmaceutical preparations are presented. Of quite particular interest among the rich series of compounds afforded by the present invention are D-2-bromo-1,6-dimethyl-8beta-(perhydroazepinylcarbonyloxymethyl)-ergoline and its salts (especially maleate and methanesulfonate) for the treatment of psychogenetic disorders, and D-2-bromo-6-methyl-8beta-(morpholinocarbonyloxymethyl)-ergoline and its salts (especially the maleate and the methanesulfonate for the treatment of asthma and allied ailments. Good tolerability, low toxicity and high effectiveness distinguish these compounds over those of the prior art.Type: GrantFiled: January 30, 1978Date of Patent: April 22, 1980Assignee: Siphar S. A.Inventors: Giorgio Ferrari, Vittorio Vecchietti
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Patent number: 4197299Abstract: A method for preparing ergoline derivatives in which the ergoline structure is variously substituted by morpholino-piperazino- and other active radicals to obtain novel compounds useful in cardiology as alpha-blocking, vasodilating, antihypertensive active ingredients of pharmaceutical preparations.Type: GrantFiled: June 20, 1978Date of Patent: April 8, 1980Assignee: Simes Societa Italiana Medicinali e SinteticiInventors: Giorgio Ferrari, Vittorio Vecchietti
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Patent number: 4196288Abstract: New ergoline derivatives are disclosed which are compounds of formula (I) having the structure: ##STR1## wherein R.sub.1 is hydrogen or methoxy; R.sub.2 is hydrogen or methyl; andX is hydroxy, R.sub.3 COO, S--R.sub.4 or NR.sub.5 R.sub.6 in which R.sub.3 is a straight or branched alkyl having from 1 to 6 carbon atoms, unsubstituted- or substituted-phenyl, the substituents being selected from the class consisting of chlorine, bromine, alkyl or alkoxy having from 1 to 4 carbon atoms, cycloalkyl containing from 3 to 6 carbon atoms, or a heterocycle;R.sub.4 is phenyl or a heterocycle, andR.sub.5 and R.sub.6 are alkyl having from 1 to 4 carbon atoms, or together with the N atom to which they are attached, forming a heterocycle.Type: GrantFiled: December 1, 1977Date of Patent: April 1, 1980Assignee: Societa Farmaceutici Italia S.p.A.Inventors: Enzo Beacco, Luigi Bernardi, Enrico Di Salle, Giovanni Falconi, Bianca Patelli
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Patent number: 4180581Abstract: The present invention provides compounds of formula I, ##STR1## wherein X is hydrogen, chlorine or bromine andY is hydrogen or bromine, with the proviso that when X is chlorine Y is hydrogen,Z is carbonyl or sulphonyl,R.sub.1 is alkyl of 1 to 4 carbon atoms, andeither (i)R.sub.2 is hydrogen or alkyl of 1 to 5 carbon atoms, andR.sub.3 is hydrogen, alkyl of 1 to 5 carbon atoms, or phenyl,or (ii)R.sub.2 together with R.sub.3 is a radical of formula ##STR2## wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms,or (iii)R.sub.2 together with R.sub.4 is a radical of formula--(CH.sub.2).sub.2 --A--(CH.sub.2).sub.2 --wherein A is a bond, oxygen, sulphur or NR.sub.8 wherein R.sub.8 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or alkoxyphenyl,useful as venotonising agents.Type: GrantFiled: January 26, 1978Date of Patent: December 25, 1979Assignee: Sandoz Ltd.Inventor: Paul Stadler
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Patent number: 4176182Abstract: Novel sulfamoyl derivatives of 8.beta.-aminomethyl ergoline having the general formula: ##STR1## are disclosed, which have interesting pharmacological properties and are useful as anti-migrainic, anti-hypertensive and psychopharmaceutically active drugs. In the method for their preparation a compound having the formula: ##STR2## is reacted, in an aprotic solvent and at a temperature of between -20.degree. C. and +150.degree. C.Type: GrantFiled: November 3, 1977Date of Patent: November 27, 1979Assignee: SIMES Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Giorgio Ferrari, Vittorio Vecchietti
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Patent number: 4167506Abstract: A group of novel polynuclear heterocyclic compounds having a diazaphenalene skeleton. These compounds assume orange to reddish violet colors according to the types of substituents on the diazaphenalene skeleton, and have excellent thermal stability and weatherability and good dispersibility in polymeric materials. They are useful as orange to reddish violet pigments, especially for coloring polymeric materials.Type: GrantFiled: September 13, 1977Date of Patent: September 11, 1979Assignee: Teijin LimitedInventors: Keizo Shimada, Toshiaki Harada, Masahiro Koga, Shizuo Nagahama, Hiroyoshi Minematsu, Hidetsugu Yoshida
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Patent number: 4163844Abstract: Novel nitrogen-containing heterocyclic compounds shown by the formula ##STR1## wherein Y represents an oxygen atom, a sulfur atom, or a group shown by ##STR2## (wherein m is 1 or 2); n represents 0 or 1; R.sub.1 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a lower alkenyl group; R.sub.2 and R.sub.3, which may be the same or different, each represents a hydrogen atom, a hydroxyl group, a lower alkanoyloxy group, a lower alkyl group or a lower alkenyl group; said R.sub.2 and R.sub.3 may further form together a double bond; R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, an amino group, a lower alkoxy group, a mono or di lower alkylamino group, or a lower alkyl group; said R.sub.5 and R.sub.6 may further form together a lower alkylenedioxy group; and R.sub.Type: GrantFiled: December 19, 1977Date of Patent: August 7, 1979Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kazuo Kubo, Noriki Ito, Isao Souzu, Yasuo Isomura, Hiroshige Homma
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Patent number: 4137315Abstract: Indolizino[7,6,5-de]isoquinoline derivatives of the general formula: ##STR1## wherein the symbol R.sub.1 represents a hydrogen atom, the symbol R.sub.2 represents a hydrogen atom, an amino radical, or a straight- or branched-chain alkyl radical which is optionally substituted on a terminal carbon atom by a vinyl, ethynyl, carboxy, alkoxycarbonyl, cyano, dialkoxymethyl, hydroxymethyl, dialkylaminomethyl (the alkyl radicals of which may form with the nitrogen atom to which they are attached a saturated five- or six-membered heterocyclic ring which may contain another hetero-atom selected from nitrogen, oxygen and sulphur, and -- when a second nitrogen atom is present -- may optionally be N-methylated) or trialkylammoniomethyl radical, or R.sub.2 represents a straight- chain alkyl radical which is substituted on the terminal carbon atom by an aminomethyl, alkylaminomethyl or hydroxyalkylaminomethyl radical, and the symbols R.sub.3 and R.sub.4 together form a valence bond, or the symbols R.sub.1 and R.sub.Type: GrantFiled: June 14, 1977Date of Patent: January 30, 1979Assignee: Rhone-Poulenc IndustriesInventors: Daniel Farge, Yves Le Goff, Gilbert Poiget
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Patent number: 4062858Abstract: New derivatives of 5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridin-11(1H)-ones and imines, respectively, have the general formula ##STR1## They and the salts thereof are useful as psychotropic and antiinflammatory agents.SUMMARY OF THE INVENTIONThis invention relates to new derivatives of 5,6-dihydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]-pyridin-11(1H)-ones and imines and salts thereof. These new compounds have the general formula ##STR2## R.sup.1 is lower alkyl, phenyl or phenyl-lower alkyl; R.sup.2 is hydrogen, lower alkyl or phenyl;R.sup.3 is hydroxy, lower alkoxy, halogen or an amine group.The amine group is either an acyclic group ##STR3## wherein R.sup.5 and R.sup.6 each is hydrogen, lower alkyl or phenyl or R.sup.5 and R.sup.6 taken together with the nitrogen form a monocyclic nitrogen heterocyclic of 5 or 6 members in which an additional nitrogen, oxygen or sulfur may be present.R.sup.4 is oxygen (.dbd.O) or substituted imine (.dbd.NR)R is lower alkyl or phenyl.Type: GrantFiled: December 22, 1976Date of Patent: December 13, 1977Assignee: E. R. Squibb & Sons, Inc.Inventors: Hans Hoehn, Jack Bernstein, B. Richard Vogt
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Patent number: 4057635Abstract: Ergoline carbamates are disclosed, which have proven to be effective spasmolytic and vasodilatory drugs. They are derivatives of D-6-methyl-8.beta.-(methanol)-9,10-didehydroergoline (also called lysergol). Three convenient methods for their preparation are also disclosed. The toxicity of these compounds is extremely low.Type: GrantFiled: August 19, 1975Date of Patent: November 8, 1977Assignee: Simes Societa Italiana Medicinali e Sintetici S.p.A.Inventors: Giorgio Ferrari, Jiri Jan Krepinsky