Tricyclo Ring System Having The Diazine Ring As One Of The Cyclos Patents (Class 544/344)
  • Patent number: 5095112
    Abstract: 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: Grant
    Filed: November 17, 1987
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Michael Preiss
  • Patent number: 5091427
    Abstract: 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: Grant
    Filed: September 1, 1989
    Date of Patent: February 25, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolf-Ulrich Nickel, Rainer Henning, Wolfgang Ruger, Ulrich Lerch, Hansjorg Urbach, Franz Hock, Gabriele Wiemer
  • Patent number: 5081123
    Abstract: 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: Grant
    Filed: December 15, 1989
    Date of Patent: January 14, 1992
    Assignee: Novo Nordisk A/S
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 5028607
    Abstract: 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: Grant
    Filed: January 4, 1990
    Date of Patent: July 2, 1991
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Francis Colpaert, Michel Lauoie
  • Patent number: 5026704
    Abstract: 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: Grant
    Filed: December 26, 1989
    Date of Patent: June 25, 1991
    Assignee: Novo Nordisk A/S
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 5026856
    Abstract: 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: Grant
    Filed: May 23, 1989
    Date of Patent: June 25, 1991
    Assignee: Wakunaga Seiyaku Kabushiki Kaisha
    Inventors: Takashi Yatsunami, Akira Yazaki, Satoshi Inoue, Hitoshi Yamamoto, Masaharu Yokomoto, Jun Nomiyama, Shuichiro Noda
  • Patent number: 4990508
    Abstract: 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: Grant
    Filed: April 13, 1989
    Date of Patent: February 5, 1991
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Hirokazu Narita, Yozo Todo, Jun Nitta, Hiroyasu Takagi, Fumihiko Iino, Mikako Miyajima, Yoshikazu Fukuoka, Isamu Saikawa
  • Patent number: 4960886
    Abstract: 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: Grant
    Filed: December 11, 1987
    Date of Patent: October 2, 1990
    Assignees: Fuji Xerox Co., Ltd., Toshio Mukai
    Inventors: Toshio Mukai, Yoshiro Yamashita, Takanori Suzuki
  • Patent number: 4948794
    Abstract: 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: Grant
    Filed: November 8, 1988
    Date of Patent: August 14, 1990
    Assignee: A/S Ferrosan
    Inventors: Tage Honore, Poul Jacobsen, Flemming E. Nielsen, Lars Naerum
  • Patent number: 4943577
    Abstract: 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: Grant
    Filed: July 19, 1989
    Date of Patent: July 24, 1990
    Assignee: Adir Et Cie
    Inventors: Gilbert Lavielle, Jean C. Poignant
  • Patent number: 4943576
    Abstract: 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: Grant
    Filed: April 22, 1988
    Date of Patent: July 24, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heiner Glombik, Roland Utz, Hans-Jochen Lang, Karl Geisen, Friedrich E. Beyhl
  • Patent number: 4929613
    Abstract: 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: Grant
    Filed: July 25, 1988
    Date of Patent: May 29, 1990
    Assignee: Warner-Lambert Company
    Inventors: Townley P. Culbertson, John M. Domagala, Susan E. Hagen, Joseph P. Sanchez
  • Patent number: 4923879
    Abstract: 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: Grant
    Filed: July 31, 1987
    Date of Patent: May 8, 1990
    Assignee: Warner-Lambert Company
    Inventors: Marland P. Hutt, Jr., John S. Kiely
  • Patent number: 4918190
    Abstract: 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: Grant
    Filed: July 30, 1987
    Date of Patent: April 17, 1990
    Assignee: Ube Industries, Ltd.
    Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
  • Patent number: 4889855
    Abstract: 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: Grant
    Filed: February 16, 1988
    Date of Patent: December 26, 1989
    Assignee: A/S Ferrosan
    Inventors: Poul Jacobsen, Flemming E. Nielsen, Tage Honore
  • Patent number: 4877788
    Abstract: 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: Grant
    Filed: June 14, 1988
    Date of Patent: October 31, 1989
    Assignee: Adir Et Cie
    Inventors: Gilbert Lavielle, Jean Claude Poignant
  • Patent number: 4812569
    Abstract: 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: Grant
    Filed: February 27, 1987
    Date of Patent: March 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Udo Eckstein
  • Patent number: 4782058
    Abstract: 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: Grant
    Filed: December 3, 1987
    Date of Patent: November 1, 1988
    Assignee: Pennwalt Corporation
    Inventor: Ronald C. Griffith
  • Patent number: 4772705
    Abstract: 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: Grant
    Filed: July 25, 1985
    Date of Patent: September 20, 1988
    Assignee: Pennwalt Corporation
    Inventor: Richard J. Schmiesing
  • Patent number: 4762831
    Abstract: 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: Grant
    Filed: June 13, 1986
    Date of Patent: August 9, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Grohe, Michael Schriewer
  • Patent number: 4761479
    Abstract: 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: Grant
    Filed: March 30, 1987
    Date of Patent: August 2, 1988
    Assignee: Warner-Lambert Company
    Inventors: Om P. Goel, Uldis Krolls
  • Patent number: 4697016
    Abstract: 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: Grant
    Filed: February 14, 1986
    Date of Patent: September 29, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Achim Roloff, Heinz W. Gschwend
  • Patent number: 4638066
    Abstract: 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: Grant
    Filed: December 20, 1984
    Date of Patent: January 20, 1987
    Assignee: Beecham Group p.l.c.
    Inventors: Laramie M. Gaster, Barry S. Orlek
  • Patent number: 4595766
    Abstract: 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: Grant
    Filed: October 26, 1984
    Date of Patent: June 17, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Achim Roloff, Heinz W. Gschwend
  • Patent number: 4571396
    Abstract: 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: Grant
    Filed: March 11, 1985
    Date of Patent: February 18, 1986
    Assignee: Warner-Lambert Company
    Inventors: Marland P. Hutt, Thomas F. Mich, Townley P. Culbertson
  • Patent number: 4560688
    Abstract: 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: Grant
    Filed: February 8, 1984
    Date of Patent: December 24, 1985
    Assignee: Schering Corporation
    Inventor: Frank J. Villani
  • Patent number: 4523013
    Abstract: 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: Grant
    Filed: January 31, 1983
    Date of Patent: June 11, 1985
    Assignee: Sanofi, S.A.
    Inventors: Daniel Frehel, Jean-Pierre Maffrand
  • Patent number: 4517187
    Abstract: 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: Grant
    Filed: October 18, 1982
    Date of Patent: May 14, 1985
    Assignee: Pennwalt Corporation
    Inventor: Ronald C. Griffith
  • Patent number: 4499270
    Abstract: 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: Grant
    Filed: February 22, 1982
    Date of Patent: February 12, 1985
    Assignee: Riker Laboratories, Inc.
    Inventor: John F. Gerster
  • Patent number: 4497952
    Abstract: 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: Grant
    Filed: July 8, 1983
    Date of Patent: February 5, 1985
    Assignee: Korea Advanced Institute of Science and Technology
    Inventors: Choong S. Kim, Nam J. Lee, Joong H. Kim
  • Patent number: 4474784
    Abstract: 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: Grant
    Filed: March 1, 1982
    Date of Patent: October 2, 1984
    Assignee: Roussel Uclaf
    Inventors: Alan C. Barnes, David A. Rowlands
  • Patent number: 4466915
    Abstract: 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: Grant
    Filed: September 29, 1982
    Date of Patent: August 21, 1984
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4446323
    Abstract: 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: Grant
    Filed: May 23, 1983
    Date of Patent: May 1, 1984
    Assignee: American Home Products Corporation
    Inventors: Meier E. Freed, Magid Abou-Gharbia
  • Patent number: 4443447
    Abstract: 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: Grant
    Filed: October 25, 1982
    Date of Patent: April 17, 1984
    Assignee: Riker Laboratories, Inc.
    Inventors: John F. Gerster, Richard M. Stern
  • Patent number: 4438116
    Abstract: 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: Grant
    Filed: September 16, 1981
    Date of Patent: March 20, 1984
    Assignee: Boehringer Mannheim GmbH
    Inventors: Carl H. Ross, Wolfgang Kampe, Wolfgang Bartsch, Gisbert Sponer, Egon Roesch
  • Patent number: 4405632
    Abstract: 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: Grant
    Filed: June 27, 1980
    Date of Patent: September 20, 1983
    Assignee: Union Carbide Corporation
    Inventors: Dean F. Bushey, Themistocles D. J. D'Silva
  • Patent number: 4397853
    Abstract: 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: Grant
    Filed: April 14, 1981
    Date of Patent: August 9, 1983
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Takeshi Kawakita, Tomio Muro, Michihide Setoguchi
  • Patent number: 4381302
    Abstract: (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: Grant
    Filed: May 26, 1981
    Date of Patent: April 26, 1983
    Assignee: Merck & Co., Inc.
    Inventors: Joel R. Huff, Stella W. King, Walfred S. Saari
  • Patent number: 4362875
    Abstract: 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: Grant
    Filed: December 6, 1978
    Date of Patent: December 7, 1982
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventor: Jurgen Seubert
  • Patent number: 4348521
    Abstract: 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: Grant
    Filed: April 16, 1981
    Date of Patent: September 7, 1982
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: John F. Gerster
  • Patent number: 4333934
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: June 8, 1982
    Assignee: Roussel Uclaf
    Inventors: Alan C. Barnes, David A. Rowlands
  • Patent number: 4299830
    Abstract: 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: Grant
    Filed: June 20, 1980
    Date of Patent: November 10, 1981
    Assignee: Sterling Drug Inc.
    Inventor: Franklyn W. Gubitz
  • Patent number: 4297514
    Abstract: 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: Grant
    Filed: March 14, 1980
    Date of Patent: October 27, 1981
    Assignee: The Dow Chemical Company
    Inventor: King W. Ma
  • Patent number: 4273773
    Abstract: 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: Grant
    Filed: September 24, 1979
    Date of Patent: June 16, 1981
    Assignee: American Home Products Corporation
    Inventors: Christopher A. Demerson, Leslie G. Humber, Jean-Marie Ferland
  • Patent number: 4213983
    Abstract: 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: Grant
    Filed: October 25, 1977
    Date of Patent: July 22, 1980
    Assignee: Beecham Group Limited
    Inventors: Michael S. Hadley, Eric A. Watts
  • Patent number: 4200751
    Abstract: 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: Grant
    Filed: November 21, 1977
    Date of Patent: April 29, 1980
    Assignee: Yamamoto Kagaku Gosei Co., Ltd.
    Inventors: Seiji Ikegami, Yoshihiro Hatano
  • Patent number: 4196291
    Abstract: 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: Grant
    Filed: December 18, 1978
    Date of Patent: April 1, 1980
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Jurgen Seubert, Herbert Thomas, Peter Andrews
  • Patent number: 4167512
    Abstract: 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: Grant
    Filed: June 19, 1978
    Date of Patent: September 11, 1979
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4162319
    Abstract: 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: Grant
    Filed: August 7, 1978
    Date of Patent: July 24, 1979
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Jurgen Seubert, Rolf Pohlke, Herbert Thomas, Peter Andrews
  • Patent number: RE30314
    Abstract: Substituted pyrroloquinoxalinones and diones, useful as anti-inflammatory and anti-thrombotic agents.
    Type: Grant
    Filed: April 26, 1979
    Date of Patent: June 24, 1980
    Assignee: Eli Lilly and Company
    Inventor: Richard E. Holmes