Tricyclo Ring System Having The Diazine Ring As One Of The Cyclos Patents (Class 544/344)
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Patent number: 5095112Abstract: A process for the preparation of quinolone-carboxylic acid esters of the formulae I and II ##STR1## in which A represents nitrogen or .dbd.C--R.sup.4,R.sup.4 represents hydrogen, fluorine, chlorine, nitro or methyl,B represents halogen, nitro, alkoxy, alkylsulphonyloxy or the radical ##STR2## and B additionally represents ##STR3## if R1 does not denote cyclopropyl, and R.sup.5 represents a branched or unbranched alkyl group which has 1 to 4 carbon atoms and which can optionally be substituted by a hydroxyl or methoxy group,R.sup.6 represents hydrogen, methyl or phenyl,R.sup.7 represents hydrogen or methyl,R.sup.8 represents dialkylamino having 1 or 2 carbon atoms in the alkyl group or dialkylaminomethyl having 1 or 2 carbon atoms in the alkyl group, or aminomethylR.sup.1 represents hydrogen, optionally substituted alkyl having 1 to 3 carbon atoms, optionally substituted cycloalkyl, 2-fluoroethyl, vinyl, methoxy or 4-fluorophenyl,R.sup.Type: GrantFiled: November 17, 1987Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventor: Michael Preiss
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Patent number: 5091427Abstract: The invention relates to compounds of the formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.4 represent optionally substituted aliphatic, alicyclic, alicyclic-aliphatic, aromatic, araliphatic, heteroaromatic or heteroaromatic-aliphatic radicals, with R.sup.2, if not already covered by the above-mentioned definitions, denoting the side-chain, which is protected if necessary, of a naturally occurring .alpha.-amino acid, R.sup.4 can additionally represent ##STR2## R.sup.3 denotes an optionally substituted aliphatic, alicyclic, aromatic or araliphatic radical, or R.sup.3 and R.sup.4 form, together with the atoms carrying them, a mono-, bi- or tricyclic heterocyclic ring system,agents containing these, and the use thereof as pharmaceuticals having a psychotropic action for the prophylaxis of disorders of the central nervous system, especially having a nootropic action for the treatment of cognitive dysfunctions.Type: GrantFiled: September 1, 1989Date of Patent: February 25, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolf-Ulrich Nickel, Rainer Henning, Wolfgang Ruger, Ulrich Lerch, Hansjorg Urbach, Franz Hock, Gabriele Wiemer
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Patent number: 5081123Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is hydroxy, alkoxy, aryloxy, aralkyloxy, cycloalkylalkoxy, cycloalkoxy, or acyloxy;R.sup.5 and R.sup.6 together form a further fused ring, which is substituted with hydrogen, halogen or CN, and R.sup.7 and R.sup.8 independently are hydrogen, NO.sub.2, halogen, CN, SO.sub.2 NR'R', SO.sub.2 R', CF.sub.3, or OR', wherein R' is hydrogen or C.sub.1-4 -alkyl; orR.sup.7 and R.sup.8 together form a further fused ring, which is substituted with hydrogen, halogen or CN, and R.sup.5 and r.sup.6 independently are hydrogen, NO.sub.2, halogen, CN, SO.sub.2 NR'R', SO.sub.2 R', CF.sub.3, or OR', wherein R' is hydrogen or C.sub.1-4 -alkyl.The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use.Type: GrantFiled: December 15, 1989Date of Patent: January 14, 1992Assignee: Novo Nordisk A/SInventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
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Patent number: 5028607Abstract: The invention relates to compounds of formula I: ##STR1## in which m=2-4,n and p, which may be identical or different, are an integer equal to 1, 2 or 3, with the proviso that the sum of n and p is not less than 3 and not more than 5,q=0 or 1,R is a 1,2,3,4-tetrahydro-3-quinazolinyl radical, optionally substituted, a 1,3,4,6,11,11a-hexahydro-1,3-dioxo-2H-pyrazino[1,2,-b]isoquinol-2-yl radical, a 1,2-dihydro-1-oxo-2-phthalazinyl radical, optionally substituted, a 2,6-dioxo-1-piperazinyl radical of formula W: ##STR2## (R.sub.3 is a 2-pyridyl radical or an optionally substituted phenyl radical),a radical of formula Z: ##STR3## (R.sub.4 is a carbamoyl radical, a cyano radical, a hydroxycarbonyl radical or an alkoxycarbonyl radical having 1 to 6 carbon atms),or a radical of formula Y: ##STR4## (R.sub.Type: GrantFiled: January 4, 1990Date of Patent: July 2, 1991Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Francis Colpaert, Michel Lauoie
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Patent number: 5026704Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substututed by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, Cl or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 - alkyl; orR.sup.7 and R.sup.Type: GrantFiled: December 26, 1989Date of Patent: June 25, 1991Assignee: Novo Nordisk A/SInventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
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Patent number: 5026856Abstract: Isoindoline derivatives represented by the formula (I) and their salts are disclosed. ##STR1## There are many varieties for the compound depending on the types of residues R.sup.1 -R.sup.9 and X. The compounds can be prepared from quinoline derivatives of the formula (II) and an isoindoline derivatives of the formula (III). The compounds of formula (I) and their salts have excellent antibacterial activities against both gram positive and gram negative microorganisms. They can be used as a medicine, an agrichemical, and a food preservative.Type: GrantFiled: May 23, 1989Date of Patent: June 25, 1991Assignee: Wakunaga Seiyaku Kabushiki KaishaInventors: Takashi Yatsunami, Akira Yazaki, Satoshi Inoue, Hitoshi Yamamoto, Masaharu Yokomoto, Jun Nomiyama, Shuichiro Noda
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Patent number: 4990508Abstract: This invention relates to a novel pyridone carboxylic acid derivative having a substituted or unsubstituted cyclopropyl group at the 10-position of pyridobenzoxazine, pyridobenzothiazine or pyridoquinoxaline and a salt thereof, a process for the production thereof and an antibacterial agent comprising the same.Type: GrantFiled: April 13, 1989Date of Patent: February 5, 1991Assignee: Toyama Chemical Co., Ltd.Inventors: Hirokazu Narita, Yozo Todo, Jun Nitta, Hiroyasu Takagi, Fumihiko Iino, Mikako Miyajima, Yoshikazu Fukuoka, Isamu Saikawa
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Patent number: 4960886Abstract: A charge transfer complex formed between a benzoquinone derivative represented by formula ##STR1## wherein at least one of the rings A and B represents a heterocyclic ring as defined in the specification, and an electron donor, and a salt of an anion or anion radical of the benzoquinone derivative of the above formula are disclosed. The charge transfer complex and the salt are useful as electronic materials.Type: GrantFiled: December 11, 1987Date of Patent: October 2, 1990Assignees: Fuji Xerox Co., Ltd., Toshio MukaiInventors: Toshio Mukai, Yoshiro Yamashita, Takanori Suzuki
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Patent number: 4948794Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.1 is C.sub.1-12 -alkyl, which may optionally be substituted by hydroxy, formyl, carboxy, carboxylic esters, amides or amines, C.sub.3-8 -cycloalkyl, aryl, aralkyl; and wherein R.sup.6 is, hydrogen, halogen, CN, CF.sub.3, NO.sub.2, or OR', wherein R' is C.sub.1-4 -alkyl and R.sup.5, R.sup.7 and R.sup.8 is hydrogen, provided R.sup.6 is not CF.sub.3, OCH.sub.3, NO.sub.2, C.sup.1 or Br when R.sup.1 is CH.sub.3 ; orR.sup.6 and R.sup.7 independently are NO.sub.2, halogen, CN, CF.sub.3, or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.5 and R.sup.8 are each hydrogen; orR.sup.5 and R.sup.6 together form a further fused aromatic ring, which may be substituted with halogen, NO.sub.2, CN, CF.sub.3 or OR', wherein R' is C.sub.1-4 -alkyl, and R.sup.7 and R.sup.8 independently are hydrogen, halogen, CN, CF.sub.3, NO.sub.2 or OR', wherein R' is C.sub.1-4 -alkyl; orR.sup.7 and R.sup.Type: GrantFiled: November 8, 1988Date of Patent: August 14, 1990Assignee: A/S FerrosanInventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
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Patent number: 4943577Abstract: The invention relates to compounds of formula I ##STR1## in which R.sub.1 and R.sub.2 form together and with the piperazine-2,6-dione radical to which they are attached a hexahydropyrazino-.beta.-cabbolinedione radical,R.sub.3 denotes a pyrimidinyl radical or a phenyl radical optionally substituted by an alkyl radical of 1 to 4 carbon atoms or a trifluoromethyl radical,n is an integer of 2 to 4, inclusive.Type: GrantFiled: July 19, 1989Date of Patent: July 24, 1990Assignee: Adir Et CieInventors: Gilbert Lavielle, Jean C. Poignant
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Patent number: 4943576Abstract: Substituted quinoxalyl-imidazolidine-2,4-diones, processes for their preparation, their use as medicaments and pharmaceutical preparations 5-Quinoxalyl-imidazolidine-2,4-diones of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings given, and physiologically tolerated salts thereof and processes for their preparation are described. The compounds inhibit aldose reductase and can be used as medicaments.Type: GrantFiled: April 22, 1988Date of Patent: July 24, 1990Assignee: Hoechst AktiengesellschaftInventors: Heiner Glombik, Roland Utz, Hans-Jochen Lang, Karl Geisen, Friedrich E. Beyhl
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Patent number: 4929613Abstract: The novel series of quinoline-, naphthyridine- and benzoxazine-carboxylic acids useful as antibacterial agents is described. Novel methods for preparing the compounds as well as novel intermediates are also described as are methods for their formulation and the use thereof in treating bacterial infections.Type: GrantFiled: July 25, 1988Date of Patent: May 29, 1990Assignee: Warner-Lambert CompanyInventors: Townley P. Culbertson, John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
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Patent number: 4923879Abstract: Novel quinoline-, naphthyridine-, and benzoxazine-carboxylic acid derivatives with bridged sidechains useful as antibacterial agents are described. Methods for their preparation, formulation, and use in treatment of bacterial infections is also described.Type: GrantFiled: July 31, 1987Date of Patent: May 8, 1990Assignee: Warner-Lambert CompanyInventors: Marland P. Hutt, Jr., John S. Kiely
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Patent number: 4918190Abstract: Disclosed are a crystalline complex compound of a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each otherand a tertiary diamine represented by Formula (II): ##STR2## wherein A represents a group having two carbon atoms as a chain member which may be branched; each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and A, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be bonded to each other,and a process of separation and purification of the propargyl alcohol using the crystalline complex compound described above.Type: GrantFiled: July 30, 1987Date of Patent: April 17, 1990Assignee: Ube Industries, Ltd.Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
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Patent number: 4889855Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein --A-- together with the two carbon atoms denoted as 1 and 2 is selected from ##STR2## R.sup.1, R.sup.2 and R.sup.3 are independently H, halogen, CN, NH.sub.2, NO.sub.2, SO.sub.3 H, SO.sub.2 NH.sub.2, or CONH.sub.2The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use.The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.Type: GrantFiled: February 16, 1988Date of Patent: December 26, 1989Assignee: A/S FerrosanInventors: Poul Jacobsen, Flemming E. Nielsen, Tage Honore
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Patent number: 4877788Abstract: The invention relates to the compounds selected from those of formula I ##STR1## in which, R.sub.1 and R.sub.2 form together and with the piperazine-2,6-dione radical to which they are attached a hexahydropyrazinoisoquinolinedione radical, a primidinyl radical or a phenyl radical optionally substituted by an alkyl radical of 1 to 4 carbon atoms or a trifluoromethyl radical,n is an integer from 2 to 4.Type: GrantFiled: June 14, 1988Date of Patent: October 31, 1989Assignee: Adir Et CieInventors: Gilbert Lavielle, Jean Claude Poignant
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Patent number: 4812569Abstract: Chromogenic phthalides of the general formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another denote hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl or aryl or are linked to the ring A or B respectively in the o-position to the nitrogen and then represent the remaining members of a partially or fully hydrogenated heterocyclic 5-membered or 6-membered ring which can contain a further heteroatom from the series O, S, N--R.sub.1 or N--R.sub.2,X.sub.1, X.sub.2, X.sub.3 and X.sub.4 independently of one another denote hydrogen, halogen, alkyl, alkenyl, aralkyl, cycloalkyl, aryl, hydroxyl, alkoxy, alkenyloxy, aralkoxy, cycloalkoxy, aryloxy, acyloxy, alkylmercapto, arylmercapto, aralkylmercapto, alkylsulphonyl, alkoxycarbonyl or nitro or X.sub.1 +X.sub.2, X.sub.2 +X.sub.3 or X.sub.3 +X.sub.4 denote a fused benzene ring,Z.sub.1 and Z.sub.Type: GrantFiled: February 27, 1987Date of Patent: March 14, 1989Assignee: Bayer AktiengesellschaftInventor: Udo Eckstein
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Patent number: 4782058Abstract: Novel 1,3,4,6,7,11b-hexahydro-6-phenyl-2H-pyrazino[2,1-a]isoquinolines, including a cis-1,3,4,6,7,11b-hexahydro-9-methoxy-2-methyl-6-phenyl-2H-pyrazino[2,1-a] isoquinoline dihydrochloride and cis-1,3,4,6,7,11b-hexahydro-9-hydroxy-2-methyl-6-phenyl-2H-pyrazino[2,1-a] isoquinoline dihydrobromide; useful as anti-histamine and anti-depressant agents.Type: GrantFiled: December 3, 1987Date of Patent: November 1, 1988Assignee: Pennwalt CorporationInventor: Ronald C. Griffith
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Patent number: 4772705Abstract: The trans isomeric form of 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazino[2,1-a]isoquinolines are prepared using novel 3-phenyl-4-arylacyl-2-piperazinones and 3-phenyl-4-(2-hydroxy-2-arylethyl) piperazines as intermediates. The process involves reacting a nove piperazinone with a reducing agent such as aluminum hydrides, borane or lithium borohydrides, and then reacting the resulting piperazine with a strong acid, such as polyphosphoric or sulfuric acid.Type: GrantFiled: July 25, 1985Date of Patent: September 20, 1988Assignee: Pennwalt CorporationInventor: Richard J. Schmiesing
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Patent number: 4762831Abstract: A process for the preparation of a 1,8-bridged 4-quinolone-3-carboxylic acid of the formula ##STR1## wherein the substituents are defined hereinbelow. Some of the compound are new. The old and new compounds are antibacterials and promote animal growth.Type: GrantFiled: June 13, 1986Date of Patent: August 9, 1988Assignee: Bayer AktiengesellschaftInventors: Klaus Grohe, Michael Schriewer
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Patent number: 4761479Abstract: A novel crystalline form of quinapril and a novel process for the large scale preparation of the ACE inhibitor, quinapril, in a highly pure state. The substance is of high bulk density suitable for formulation in capsules and tablets. This inexpensive process uses HCl gas in glacial acetic acid for rapid and clean de-t-butylation at room temperature.Type: GrantFiled: March 30, 1987Date of Patent: August 2, 1988Assignee: Warner-Lambert CompanyInventors: Om P. Goel, Uldis Krolls
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Patent number: 4697016Abstract: The invention relates to a novel process for the preparation of the optically pure 2S- or 2R-indolinecarboxylic acid of the formula ##STR1## and salts thereof. The process comprises forming the heterocyclic 5-membered ring in formula I from an open chain precursor by diastereoselective cyclization.Type: GrantFiled: February 14, 1986Date of Patent: September 29, 1987Assignee: Ciba-Geigy CorporationInventors: Achim Roloff, Heinz W. Gschwend
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Patent number: 4638066Abstract: Compounds of formula (I), ##STR1## or an N-oxide or pharmaceutically acceptable salt thereof, wherein R.sub.1 is hydrogen, C.sub.1-7 alkyl, C.sub.3-7 cycloalkyl, C.sub.4-7 cycloalkenyl or C.sub.1-4 alkyl substituted by C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, C.sub.3-7 cycloalkyl, hydroxy, thiol, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, carboxy, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkanoyl, amino optionally substituted by one or two C.sub.1-4 alkyl or by C.sub.4-6 polymethylene optionally containing an oxygen or nitrogen atom, aminocarbonyl optionally N-substituted by one or two C.sub.1-4 alkyl, or benzoyl or phenyl either being optionally ring-substituted by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halogen or trifluoromethyl, R.sub.2 and R.sub.3 are the same or different and are hydrogen, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen or trifluoromethyl, m is 1 to 3 and n is 1 or 2, the hydrogen atom bonded to the C.sub.a carbon atom being trans to the hydrogen atom bonded to the C.sub.Type: GrantFiled: December 20, 1984Date of Patent: January 20, 1987Assignee: Beecham Group p.l.c.Inventors: Laramie M. Gaster, Barry S. Orlek
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Patent number: 4595766Abstract: The invention relates to a novel process for the preparation of the optically pure 2S- or 2R-indolinecarboxylic acid of the formula ##STR1## and salts thereof. The process comprises forming the heterocyclic 5-membered ring in formula I from an open chain precursor by diastereoselective cyclization.Type: GrantFiled: October 26, 1984Date of Patent: June 17, 1986Assignee: Ciba-Geigy CorporationInventors: Achim Roloff, Heinz W. Gschwend
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Patent number: 4571396Abstract: Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.Type: GrantFiled: March 11, 1985Date of Patent: February 18, 1986Assignee: Warner-Lambert CompanyInventors: Marland P. Hutt, Thomas F. Mich, Townley P. Culbertson
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Patent number: 4560688Abstract: Antihistamines of the formula ##STR1## wherein ##STR2## is a 5 or 6 membered ring which is phenyl or heterocyclic; ##STR3## is a six membered ring which is 2,3, or 4 pyridyl or is phenyl or substituted phenyl, with the proviso that is ##STR4## is a nitrogen containing ring, ##STR5## must be phenyl; Z is an alkylene chain having 0 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen, or a hydroxy group as a substituent; W is ##STR6## wherein p is 1 or 2 and n is 1 or 2, R.sup.1 is C.sub.1 to C.sub.6 alkyl, R.sup.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, and the dotted line represents an optional double bond, R.sup.2 being absent if the double bond is present, and Y is substiuted carboxylate or substituted sulfonyl. Said antihistamines have little or no sedative effects.Type: GrantFiled: February 8, 1984Date of Patent: December 24, 1985Assignee: Schering CorporationInventor: Frank J. Villani
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Patent number: 4523013Abstract: 2-Acyl-1,3,4,6,7,11b-hexahydro-2H-pyrazino-[2,1-a]-4-isoquinoleinones having anthelmintic activity of the formula ##STR1## are prepared from 4-acyl-2,6-dioxopierazines by reaction with a phenethyl halide, selective reduction of one of the oxo groups and cyclization, by the novel intermediates of formula ##STR2## in which Y represents O or H, OH.Type: GrantFiled: January 31, 1983Date of Patent: June 11, 1985Assignee: Sanofi, S.A.Inventors: Daniel Frehel, Jean-Pierre Maffrand
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Patent number: 4517187Abstract: 1,3,4,6,7-11b-Hexahydro-7-aryl-2H-pyrazino[2,1-a]isoquinolines useful as chemical intermediates and as pharmaceuticals and methods for their preparation.Type: GrantFiled: October 18, 1982Date of Patent: May 14, 1985Assignee: Pennwalt CorporationInventor: Ronald C. Griffith
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Patent number: 4499270Abstract: Antimicrobial compounds having the heterocyclic nucleus pyrido[1,2,3-de]quinoxaline are disclosed. The process of making the compounds and novel intermediates are also disclosed.Type: GrantFiled: February 22, 1982Date of Patent: February 12, 1985Assignee: Riker Laboratories, Inc.Inventor: John F. Gerster
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Patent number: 4497952Abstract: This invention discloses a process for the preparation of (.+-.)-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives which comprises conducting an intramolecular cyclization reaction of the compounds of formulas II III in an acid medium.Type: GrantFiled: July 8, 1983Date of Patent: February 5, 1985Assignee: Korea Advanced Institute of Science and TechnologyInventors: Choong S. Kim, Nam J. Lee, Joong H. Kim
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Patent number: 4474784Abstract: Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is selected from the group consisting of --0--, ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-nitrogen or carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-nitrogen or carbon-carbon bond or taken with X is .dbd.0 and X is hydrogen or taken with Y is .dbd.0, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having anti-allergic activity and their preparation.Type: GrantFiled: March 1, 1982Date of Patent: October 2, 1984Assignee: Roussel UclafInventors: Alan C. Barnes, David A. Rowlands
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Patent number: 4466915Abstract: A known base-induced catalytic ketoform synthesis can now be carried out without sacrificing the directivity of the prior art process, but non-catalytically, that is, in the absence of the phase transfer catalyst heretofore required, provided the ketone/araldehyde is present in large excess from about 2 to about 25 times the calculated molar amount necessary to yield the reaction product. This synthesis obviates the problems of separating and recovering a phase transfer catalyst used in the prior art process.Type: GrantFiled: September 29, 1982Date of Patent: August 21, 1984Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4446323Abstract: Tetra- and hexa-hydropyrrolo[1,2-a]quinoxaline and azaquinoxaline derivatives of the formula: ##STR1## in which X is O or H.sub.2 ;Y is CH or N;R is hydrogen, alkyl, dialkylaminoalkyl, arylalkyl, phenoxyalkyl, benzoyl, pyridylalkyl or variations thereof; andR.sup.1 is hydrogen, alkyl, alkoxy, nitro, halo, trifluoromethyl, amino, alkylamino or dialkylamino;or pharmaceutically acceptable salts thereof; are anti-hypertensive agents.Type: GrantFiled: May 23, 1983Date of Patent: May 1, 1984Assignee: American Home Products CorporationInventors: Meier E. Freed, Magid Abou-Gharbia
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Patent number: 4443447Abstract: Antimicrobial compounds of the following formula are disclosed: ##STR1## wherein X is selected from the group consisting of --O--, --CH.sub.2 and ##STR2## m is 0 or 1; R.sub.1 is selected from the group consisting of hydrogen, nitro, amino, lower alkyl, lower alkanamido, lower N,N-dialkylamino, formamido, hydroxy, lower alkoxy, halogen, lower haloalkanamido and pyrryl; n is 1 or 2; and R.sub.2 is selected from the group consisting of hydrogen, methyl, fluoro, chloro and nitro. Acyl chlorides, esters, alkylaminoalkyl ester salts, amides and pharmaceutically acceptable carboxylate salts are also disclosed. Pharmaceutical compositions containing these compounds, methods of using these compound and synthetic intermediates are also disclosed.Type: GrantFiled: October 25, 1982Date of Patent: April 17, 1984Assignee: Riker Laboratories, Inc.Inventors: John F. Gerster, Richard M. Stern
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Patent number: 4438116Abstract: An aminopropanol compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from hydrogen and lower alkyl; orR.sub.1 and R.sub.2 together represent an alkylene radical;R.sub.3 is hydrogen or acyl;A is one of the following structures ##STR2## wherein R.sub.4 is hydrogen or lower alkyl optionally substituted by hydroxyl halogen and lower alkylthio; andR.sub.5 and R.sub.Type: GrantFiled: September 16, 1981Date of Patent: March 20, 1984Assignee: Boehringer Mannheim GmbHInventors: Carl H. Ross, Wolfgang Kampe, Wolfgang Bartsch, Gisbert Sponer, Egon Roesch
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Patent number: 4405632Abstract: Novel derivatives of bicyclic 2-iminothiazolidine oximes and methods of preparing same. This invention is also directed to an insecticidal composition comprising an acceptable carrier and an insecticidally effective amount of a compound of this invention, as well as to a method of controlling insects which comprises subjecting the insects to an insecticidally effective amount of a compound of this invention.Type: GrantFiled: June 27, 1980Date of Patent: September 20, 1983Assignee: Union Carbide CorporationInventors: Dean F. Bushey, Themistocles D. J. D'Silva
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Patent number: 4397853Abstract: Isoxazole derivatives represented by the formula ##STR1## wherein Ar, R.sup.1, R.sup.2 and Am are as defined in the specification, or salts thereof. These compounds are useful as drugs such as psychotropic agent, antiemetic agent, etc.Type: GrantFiled: April 14, 1981Date of Patent: August 9, 1983Assignee: Yoshitomi Pharmaceutical Industries Ltd.Inventors: Takeshi Kawakita, Tomio Muro, Michihide Setoguchi
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Patent number: 4381302Abstract: (6a.alpha.,10a.alpha.,11a.alpha.)-2-(2-pyridinyl)-1,3,4,6,6a,7,8,9,10,10a,1 1,11a-dodecahydro-2H-pyrazino[1,2-b]isoquinoline and derivatives or acid addition salts thereof are selective .alpha..sub.2 -adrenergic receptor antagonists and thereby useful as antidepressant agents and for treating sedation caused by antihypertensive therapy.Type: GrantFiled: May 26, 1981Date of Patent: April 26, 1983Assignee: Merck & Co., Inc.Inventors: Joel R. Huff, Stella W. King, Walfred S. Saari
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Patent number: 4362875Abstract: Novel tetrahydroquinolines of the formula ##STR1## wherein R is cycloalkyl or cycloalkenyl each containing 4-7 ring carbon atoms and the cycloalkyl optionally being substituted by one of methyl, hydroxyl or oxo; phenyl substituted by 1-2 of amino, acylamino of up to 4 carbon atoms, Hal, hydroxyl, methoxy or nitro, wherein Hal is fluorine, chlorine, bromine or iodine; thienyl; pyridyl; tetrahydropyranyl; tetrahydrothiopyranyl; and when at least one of R.sup.2, R.sup.3, R.sup.4, R.sup.5 or R.sup.6 is other than H, also phenyl; R.sup.2, R.sup.3 and R.sup.4 each are H or methyl; R.sup.5 and R.sup.6 each are H, methyl or methoxy; R.sup.7 is H or --CO--CH.sub.Type: GrantFiled: December 6, 1978Date of Patent: December 7, 1982Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventor: Jurgen Seubert
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Patent number: 4348521Abstract: Antimicrobial compounds having the heterocyclic nucleus pyrido[1,2,3-de]quinoxaline are disclosed. The process of making the compounds and novel intermediates are also disclosed.Type: GrantFiled: April 16, 1981Date of Patent: September 7, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: John F. Gerster
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Patent number: 4333934Abstract: Novel compounds of the formula ##STR1## wherein A is selected from the group consisting of nitrogen and .dbd.CH--, G is selected from the group consisting of ##STR2## Z is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms or taken with Y forms a carbon-nitrogen or carbon-carbon bond, Z' is selected from the group consisting of hydrogen and halogen, Y is hydrogen, or taken with Z is a carbon-nitrogen or carbon-carbon bond or taken with X is .dbd.O and X is hydrogen or taken with Y is .dbd.O, R is selected from the group consisting of hydroxymethyl, formyl, tetrazol-5-yl, N-(tetrazol-5-yl) carbamoyl, aminomethyl and carbamoyl, R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms and its non-toxic, pharmaceutically acceptable acid addition salts having antiallergic activity and their preparation.Type: GrantFiled: February 4, 1980Date of Patent: June 8, 1982Assignee: Roussel UclafInventors: Alan C. Barnes, David A. Rowlands
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Patent number: 4299830Abstract: 4-Q-9-RR'N-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocines whereinQ is propyl, isobutyl, neopentyl, allyl, 2-methyl-2-propenyl, 2-chloro-2-propenyl, cis-3-chloro-2-propenyl, cis-3-chloro-2-butenyl, trans-3-chloro-2-butenyl, propargyl, cyclopropylmethyl or (2,2-dichlorocyclopropyl)methyl; andR and R' are both hydrogens or both methyls; orR is hydrogen and R' is methyl, ethyl, propyl, butyl, isobutyl or benzyland acid addition salts thereof are useful as strong analgesics and are prepared from the known 3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine by multi-step processes including acylation (including acetylation), nitration, nitro reduction, amide reduction, deacetylation, alkylation and dimethylation.Type: GrantFiled: June 20, 1980Date of Patent: November 10, 1981Assignee: Sterling Drug Inc.Inventor: Franklyn W. Gubitz
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Patent number: 4297514Abstract: Compounds having activated methylene radicals are oxidized to various oxidation products by an improved process comprising contacting the compound with an oxidizing agent and a base of sufficient strength to deprotonate at least one hydrogen from the activated methylene radical in the presence of a catalytic amount of a synergistic combination of elemental carbon and a phase-transfer catalyst. For example, flourene is oxidized to flourenone by contacting the flourene with elemental oxygen and sodium hydroxide in the presence of a catalytic amount of the synergistic combination of charcoal and benzyltriethyl-ammonium chloride.Type: GrantFiled: March 14, 1980Date of Patent: October 27, 1981Assignee: The Dow Chemical CompanyInventor: King W. Ma
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Patent number: 4273773Abstract: Tricyclic isoindole derivatives characterized by having a 1,2,3,4,6,10b-hexahydropyrazino[2,1-a]isoindole or 1,3,4,10b-tetrahydropyrimido[6,1-a]isoindol-6(2H)-one nucleus are disclosed. The foregoing compounds are useful antihypertensive agents.Type: GrantFiled: September 24, 1979Date of Patent: June 16, 1981Assignee: American Home Products CorporationInventors: Christopher A. Demerson, Leslie G. Humber, Jean-Marie Ferland
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Patent number: 4213983Abstract: Compounds of the formula (I), and their pharmaceutically acceptable salts: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy group;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, CF.sub.3, hydroxy, C.sub.1-6 alkoxy, C.sub.2-7 acyl, amino, amino substituted by one or two C.sub.1-6 alkyl groups, C.sub.2-7 acylamino aminocarbonyl or aminosulphone optionally substituted by one or twoC.sub.1-6 alkyl groups, C.sub.1-6 alkylsulphone or nitro groups;X is either a nitrogen atom, in which case m+n is 3 to 5, m is 2 to 4, n is 1 to 3; or X is CH in which case m+n is 2 to 5, m is 1 to 5, and n is 0 to 4;p is 0 to 3;R.sub.4 is hydrogen, C.sub.1-6 alkyl, phenyl or phenyl-C.sub.1-6 alkyl, either of which phenyl moiety may be substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy, CF.sub.3 or halogen, and R.sub.5 is hydrogen; or R.sub.4 and R.sub.5 are attached to two adjacent carbon atoms and form together with these two carbon atoms a fused benzene ring, which benzene ring may be substituted by C.sub.Type: GrantFiled: October 25, 1977Date of Patent: July 22, 1980Assignee: Beecham Group LimitedInventors: Michael S. Hadley, Eric A. Watts
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Patent number: 4200751Abstract: Lactone electron donative color-forming agents of quinoline-carboxylic acid are disclosed having the general formulae (I) and (II) ##STR1## wherein A and B represent a variety of chemical moieties, X represents halo- or nitro- and n.sup.1 is an integer of 0-4. The color-forming agents are useful in recording materials of the pressure-sensitive and heat-sensitive varieties, and the like.Type: GrantFiled: November 21, 1977Date of Patent: April 29, 1980Assignee: Yamamoto Kagaku Gosei Co., Ltd.Inventors: Seiji Ikegami, Yoshihiro Hatano
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Patent number: 4196291Abstract: 2-Acyl-4-oxo-hexahydro-4H-pyrazino[2,1-a]isoquinoline derivatives of the formula ##STR1## wherein COR is the acyl radical of an up to 26 carbon atom acid and their physiologically acceptable acid addition and quaternary ammonium salts, are anthelmintics and can be produced by reacting 4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinoline with an acid or a reactive functional derivative thereof. This is a division, or application Ser. No. 742,133, filed on Nov. 15, 1976, which in turn is a divisional of Ser. No. 533,467, filed on Dec. 16, 1974, now U.S. Pat. No. 4,001,411.Type: GrantFiled: December 18, 1978Date of Patent: April 1, 1980Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Jurgen Seubert, Herbert Thomas, Peter Andrews
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Patent number: 4167512Abstract: Several novel syntheses have been discovered for preparation of 2-keto-1,4-diazacycloalkanes and their derivatives. Trans isomers of polysubstituted quinoxalin-2-ones may now be prepared.Type: GrantFiled: June 19, 1978Date of Patent: September 11, 1979Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4162319Abstract: Isoquinolines of the formula ##STR1## wherein R.sup.1 is H, OH, alkyl; R.sup.2 is H, or an unsubstituted or substituted carbonyl, carbonyloxy or thiocarbonyl group; R.sup.3 is H, alkyl or hydroxy alkyl; R.sup.4 is H, alkyl or phenyl; R.sup.5 is O, H,H or H and alkyl, phenyl, halo or hydroxy; R.sup.6 and R.sup.7 are optional substituents; and R.sup.8 is H or alkyl, R.sup.2 being a thiocarbonyl or carbonyloxy group when R.sup.1 and R.sup.3 to R.sup.8 are H and X is O; and their physiologically acceptable salts, are antihelmintics, especially against cestodes and trematodes; some also possessing CNS activity, e.g., psychotropic and blood pressure regulating activity.Type: GrantFiled: August 7, 1978Date of Patent: July 24, 1979Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Jurgen Seubert, Rolf Pohlke, Herbert Thomas, Peter Andrews
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Patent number: RE30314Abstract: Substituted pyrroloquinoxalinones and diones, useful as anti-inflammatory and anti-thrombotic agents.Type: GrantFiled: April 26, 1979Date of Patent: June 24, 1980Assignee: Eli Lilly and CompanyInventor: Richard E. Holmes