Tricyclo Ring System Having The 1,2-diazine Ring As One Of The Cyclos Patents (Class 544/234)
  • Patent number: 5527911
    Abstract: The invention relates to photochromic compounds of general formula: ##STR1## in which R.sup.a, R.sup.b and R.sup.c denote hydrogen; alkyl; aryl; OR, SR, COR or COOR, in which R denotes hydrogen, alkyl or aryl, amino of formula NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 denote hydrogen, alkyl, cycloalkyl, aryl, R.sub.1 and R.sub.2 being capable of forming with the nitrogen atom, a heterocycle containing 4 to 7 members and capable of containing, in addition, one or more heteroatoms chosen from nitrogen, oxygen, sulfur, a halogen atom; a mono- or polyhaloalkyl group; an NO.sub.
    Type: Grant
    Filed: March 19, 1993
    Date of Patent: June 18, 1996
    Assignee: Essilor International
    Inventors: Robert Guglielmetti, Jean L. Pozzo, Andre Samat
  • Patent number: 5512564
    Abstract: The present invention concerns thiazolo- 2,3-a!pyrrole and oxazolo- 1,2-a!pyrrole derivatives of formula I ##STR1## in which HET represents a heterocyclic ring with 3-7 ring atoms which can be substituted by one, two or three residues R.sup.1 which can be the same or different,Y represents an oxygen or sulphur atom, or a SO or SO.sub.2 group,X can be an oxygen or sulphur atom,R denotes an aliphatic residue with 1-9 C-atoms which can be substituted by phenyl or denotes a phenyl ring or a carbocyclic ring with 7-15 C atoms or a heterocyclic ring system each having 5 or 6 ring atoms,in which the aforementioned phenyl rings, carbocyclic rings or heterocyclic ring system can be substituted once or several times, if desired, and R1-R5 denote hydrogen or an aliphatic residue, as well as their tautomers, enantiomers, diastereomers and physiologically tolerated salts.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: April 30, 1996
    Assignee: Boehringer Mannheim GmbH
    Inventors: Harald Zilch, Herbert Leinert, Alfred Mertens
  • Patent number: 5492909
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 are a hydrogen atom, a lower alkyl group or a 5- to 7-membered cyclic group formed together with the adjacent --C.dbd.C--; X is an oxygen atom, a sulfur atom or a methylene group; Y is an optionally substituted methylene group, a divalent 3- to 7-membered homo- or heterocyclic group; R.sup.6 and R.sup.7 are a hydrogen atom, a lower alkyl group, a cycloalkyl group, an aryl group, or a nitrogen-containing heterocyclic group formed together With the adjacent nitrogen atom; m is an integer of 0 to 4; and n is an integer of 0 to 4, or a salt thereof. Said compound has an excellent anti-PAF activity, antiallergic action, etc., thus is useful as an antiasthmatic agent.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: February 20, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Masahiro Kajino, Yasuko Ashida
  • Patent number: 5491145
    Abstract: Novel compound of the general formula: ##STR1## wherein R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, provided that either R.sup.2 or R.sup.3 is a hydrogen atom, the other being an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C=C-- group, form a 5- to 7-membered ring; X stands for an oxygen atom or S(O).sub.p (p stands for an integer from 0 to 2; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for a hydrogen atom, an optionally substituted lower lakyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.
    Type: Grant
    Filed: November 21, 1994
    Date of Patent: February 13, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5482939
    Abstract: Novel compound represented by the formula: ##STR1## wherein R.sup.1 stands for H, an optionally substituted lower alkyl group or a halogen; R.sup.2 and R.sup.3 respectively stands for a hydrogen or an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C.dbd.C-- group, form a 5- to 7-membered ring; X stands for O, SO or SO.sub.2 ; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for H or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for H, an optionally substituted lower alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.6 and R.sup.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: January 9, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5474974
    Abstract: There are provided new 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives of the formula (I) ##STR1## The new 3-hydroxy-4-aryl-5-oxo-pyrazoline derivatives of the formula (I) have a particularly pronounced activity against animal pests, in particular against insects and arachnids, and against weeds.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: December 12, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Wieland Kruger, Reiner Fischer, Heinz-Jurgen Bertram, Thomas Bretschneider, Stefan Bohm, Andreas Krebs, Thomas Schenke, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt, Christoph Erdelen, Ulrike Wachendorff-Neumann, Wilhelm Stendel
  • Patent number: 5442062
    Abstract: The present invention provides a novel imidazole derivative having the chemical formula ##STR1## These compounds are useful for preventing or treating hypertension or congestive heart failure and have high activity, rapid action upon intravenous injection, good oral absorbtion, low toxicity, and long-lasting action. Also provided are pharmaceutical compositions which contain these compounds.
    Type: Grant
    Filed: April 22, 1994
    Date of Patent: August 15, 1995
    Assignee: The Upjohn Company
    Inventors: Keiko Koh, Mikio Taniguchi, Noriie Itoh, Hiroshi Kushida, Osamu Morita, Hiroyoshi Yamada, Kiyotaka Munesada, Kazuo Tsuzuki, Mineo Kunihara, Yoshiji Fujita
  • Patent number: 5432177
    Abstract: A class of pyrrolo[2,3-b]pyridine derivatives, substituted at the 3-position by a substituted piperazinylmethyl moiety, are antagonists of dopamine receptor subtypes within the brain, having a selective affinity for the dopamine D.sub.4 receptor subtype over other dopamine receptor subtypes, and are accordingly of benefit in the treatment and/or prevention of psychotic disorders such as schizophrenia while manifesting fewer side-effects than those associated with classical neuroleptic drugs.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: July 11, 1995
    Assignee: Merck Sharpe & Dohme Ltd.
    Inventors: Raymond Baker, Janusz J. Kulagowski, Neil R. Curtis, Paul D. Leeson, Mark P. Ridgill
  • Patent number: 5420275
    Abstract: An assay method which comprises utilizing chemiluminescence of a pyridopyridazine compound of the formula ##STR1## wherein R.sub.1 is a hydrocarbon group or a heterocyclic group each of which may be substituted and R.sub.2 is hydroxy group, thiol group, amino group or a monosubstituted amino group, and when R.sub.2 is a monosubstituted amino group, R.sub.2 may be taken together with R.sub.1 to form the ring; R.sub.3 is hydrogen atom, a hydroxy group which may be substituted, an amino group which may be substituted, a thiol group which may be substituted, a halogen atom, a heterocyclic group, nitro group, cyano group, carboxyl group which may be esterified or amidated, azido group, sulfo group or an organic sulfonyl group, provided that when R.sub.1 is an aliphalic group, R.sub.3 is not hydrogen atom; and X is oxygen atom or sulfur atom/or a salt thereof; and a novel compound of the formula (I) wherein the symbols are as defined above with proviso that R.sub.3 is hydrogen atom, R.sub.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: May 30, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirotomo Masuya, Yoshio Aramaki
  • Patent number: 5399553
    Abstract: A tricyclic compound represented by the general formula (1) and salts thereof are disclosed. ##STR1## A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are also disclosed.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: March 21, 1995
    Assignees: Wakunaga Seiyaku Kabushiki Kaisha, Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masaharu Yokomoto, Akira Yazaki, Norihiro Hayashi, Shunso Hatono, Satoshi Inoue, Yasuhiro Kuramoto
  • Patent number: 5391741
    Abstract: There are described a novel squarylium compound represented by the formula (I): ##STR1## and an optical information recording medium using the squarylium compound in the recording layer.
    Type: Grant
    Filed: April 23, 1993
    Date of Patent: February 21, 1995
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Ikuo Shimizu, Hiroshi Toyoda, Yukiyoshi Ito, Tsutomu Sato
  • Patent number: 5389633
    Abstract: Novel compound represented by the formula: ##STR1## wherein R.sup.1 stands for H, an optionally substituted lower alkyl group or a halogen; R.sup.2 and R.sup.3 respectively stands for a hydrogen or an optionally substituted lower alkyl group, or R.sup.2 and R.sup.3 may, taken together with the adjacent --C.dbd.C-- group, form a 5- to 7-membered ring; X stands for O, SO or SO.sub.2 ; Y stands for a group of the formula: ##STR2## (R.sup.4 and R.sup.5 respectively stand for H or an optionally substituted lower alkyl group) or a divalent group derived from an optionally substituted 3- to 7-membered homocyclic or heterocyclic ring; R.sup.6 and R.sup.7 each stands for H, an optionally substituted lower alkyl group, an optionally substituted cycloalkyl group or an optionally substituted aryl group, or R.sup.6 and R.sup.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: February 14, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5380718
    Abstract: Arthropodicidal tetrahydropyridazines of Formulae I and II, ##STR1## wherein Q,X,X.sup.1 Y, and G are as defined in the text, compositions containing them and their use in the control of arthropods.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: January 10, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Charles R. Harrison, George P. Lahm, Thomas M. Stevenson
  • Patent number: 5378843
    Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pyridinedicarboxylic acids.
    Type: Grant
    Filed: November 22, 1993
    Date of Patent: January 3, 1995
    Assignee: American Cyanamid Company
    Inventor: Henry L. Strong
  • Patent number: 5369104
    Abstract: Novel compound represented by the formula: ##STR1## wherein X stands for a methine (i.e. the group --CH.dbd.) group or a nitrogen atom; R.sup.1 stands for a hydrogen atom, an optionally substituted lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 respectively stand for a hydrogen atom or an optionally substituted lower alkyl group, or, taken together, may form a 5- to 7-membered ring combined with the adjacent --C.dbd.C--; R.sup.4 and R.sup.5 respectively stands for a hydrogen atom or an optionally substituted lower alkyl group or, taken together, form a 3- to 7-membered homo- or heterocyclic ring combined with the adjacent carbon atom; A stands for an optionally substituted amino group; m and n denote 1 to 4, respectively, or salts thereof which has an antiallergic, antiinflammatory and anti-PAF activity and is useful as an antiasthmatic agent.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: November 29, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Akio Miyake, Yasuhiko Kawano, Yasuko Ashida
  • Patent number: 5359066
    Abstract: A compound represented by the following general formula: ##STR1## which is useful as an intermediate for production of a clinically excellent synthetic antibacterial, a salt thereof, and a process for producing the same.In said formula,R.sup.1 is a hydrogen atom or a carboxyl-protecting group;R.sup.2 is a hydrogen atom or a lower alkyl group;X.sup.1 is a hydrogen atom or a halogen atom;X.sup.2 is a halogen atom;X.sub.a.sup.5 is a hydrogen atom or a halogen atom;A is a methylene group; a group of >CH--COOR.sup.4, etc.,in which R.sup.4, R.sup.5 and R.sup.6 each are a hydrogen atom or a carboxyl-protecting group;B is a methylene group or a carbonyl group;provided that both A and B must not be methylene groups at the same time.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: October 25, 1994
    Assignees: Wakunaga Pharmaceutical Co., Ltd., Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Hideo Tsutsumi, Takeshi Terasawa, David Barrett, Masayoshi Murata, Kazuo Sakane, Akira Yazaki, Satoshi Inoue
  • Patent number: 5340808
    Abstract: Fused pyridazinoquinazoline compounds, salts thereof, methods of production, intermediates in their production, pharmaceutical compositions containing said compounds and methods for treating neurodegenerative disorders using said compositions are disclosed.
    Type: Grant
    Filed: November 13, 1992
    Date of Patent: August 23, 1994
    Assignee: Warner Lambert Company
    Inventors: Juan C. Jaen, Bradley W. Caprathe
  • Patent number: 5324835
    Abstract: Compounds useful as luminescent labelling reagents or reagents for determining hydrogen peroxide of the following formula: ##STR1## Wherein R is selected from the group consisting of hydrogen, amino, carboxyl, thiol, n-propyl, isopropyl, n-butyl, sec-butyl, benzyl, carboxyethyl, tert-butyl, and--(CH.sub.2).sub.n1 CH.sub.3 wherein n.sub. is 0 or an integer of 1-15;--(CH.sub.2).sub.n2 COOH wherein n.sub.2 is 0 or an integer of 1-5;--CH.sub.2 SH; --CH.sub.2 X.sub.1 wherein X is Br, Cl or F;--(CH.sub.2).sub.n3 NH.sub.2 wherein n.sub.3 is an integer of 1-5; ##STR2## wherein n.sub.4 is 0 or 1 and n.sub.5 is 0 or ##STR3## wherein n.sub.6 is 0 or 1 and X.sub.2 is H, Br, Cl, F or I; and --(CH.sub.2).sub.n7 R.sub.1 wherein n.sub.7 is 0 or an integer of 1-5 and R.sub.1 is selected from COCl, CON.sub.3, CONHNH.sub.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: June 28, 1994
    Assignee: Biosensor Laboratories Co., Ltd.
    Inventor: Masatoshi Yamaguchi
  • Patent number: 5314887
    Abstract: There are provided novel 1,4-dihydropyridine compounds possessing both calcium agonist and alpha.sub.1 -antagonist activity useful for treating congestive heart failure, pharmaceutical compositions containing them and methods of using these compounds to treat congestive heart failure in a mammal.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: May 24, 1994
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventors: Paul E. Aldrich, Richard A. Earl, Philip Ma
  • Patent number: 5288866
    Abstract: There are provided 5,6-disubstituted-3-pyridylmethyl ammonium halide compounds, a method for the preparation thereof and the use thereof for the preparation of 5-(substituted methyl)-2,3-pyridinedicarboxylic acids.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: February 22, 1994
    Assignee: American Cyanamid Company
    Inventor: Henry L. Strong
  • Patent number: 5286860
    Abstract: This invention encompasses compounds of the formula: ##STR1## and pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## represents: ##STR3## where n is 0, 1, or 2; R.sub.1 and R.sub.2 are hydrogen or straight or branched chain alkyl groups;Y represents various organic and inorganic substituents;W represents an aromatic group substituted with various organic and inorganic substituents;A is CH or N;B is a substituted or unsubstituted carbon or N; andE is hydrogen or straight or branched alkyl groupsThese compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine type drugs, and enhancement of alertness.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: February 15, 1994
    Assignee: Neurogen Corporation
    Inventors: Charles Blum, Alan Hutchison
  • Patent number: 5254685
    Abstract: A tricyclic compound represented by the general formula (1) and salts thereof. ##STR1## A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are also disclosed.
    Type: Grant
    Filed: August 7, 1991
    Date of Patent: October 19, 1993
    Assignees: Wakunaga Seiyaku Kabushiki Kaisha, Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masaharu Yokomoto, Akira Yazaki, Norihiro Hayashi, Shunso Hatono, Satoshi Inoue, Yasuhiro Kuramoto
  • Patent number: 5212309
    Abstract: Chemiluminescenct 3-aminobenzene-1,2,4,5-tetracarboxylic dihydrazides.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: May 18, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Schefczik, Klaus Huemke
  • Patent number: 5180735
    Abstract: The present invention relates to a compound of the formula: ##STR1## wherein A is halogen, N(O)mR.sup.1 R.sup.2, N.sup..sym. R.sup.1 R.sup.2 R.sup.3 .multidot.X.sup..crclbar., S(O)nR.sup.1 or S.sup..sym. (O)mR.sup.1 R.sup.2 .multidot.X.sup..crclbar. where R.sup.1, R.sup.2 and R.sup.3 are each optionally substituted hydrocarbon or heterocyclic group, X.sup..crclbar. is a counter anion; m is an integer of 0 or 1; n is an integer of 0 to 2; R.sup.1 and R.sup.2 may form a nitrogen-containing or a sulfur-containing heterocyclic ring, which may further form a condensed ring, with the adjacent nitrogen atom or sulfur atom, and these nitrogen-containing or sulfur-containing heterocyclic rings may have substituents, Z is O or NR.sup.4 where R.sup.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: January 19, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shoji Kishimoto, Shogo Marui, Takeshi Fujita
  • Patent number: 5175162
    Abstract: Thiophene compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, halogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, nitro, amino, halogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, acyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, aryloxy-C.sub.1-4 alkyl, acyloxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl, acyloxy-C.sub.2-5 alkanoyl, C.sub.1-4 alkoxy-C.sub.2-5 alkanoyl, hydroxy-C.sub.2-5 alkanoyl, aryloxy-C.sub.2-5 alkanoyl or C.sub.2-5 haloalkanoyl; R.sup.3 is hydrogen, C.sub.1-8 alkyl, hydroxy-C.sub.1-4 alkyl, C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, aryl, aryl-C.sub.1-4 alkyl, heteroaryl, heteroaryl-C.sub.1-4 alkyl or aryl, aryl-C.sub.1-4 alkyl, heteroaryl or heteroaryl-C.sub.1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 alkanoylamino, C.sub.1-4 haloalkyl, acyloxy, C.sub.
    Type: Grant
    Filed: October 30, 1990
    Date of Patent: December 29, 1992
    Assignee: Yoshitiomi Pharmaceutical Industries Ltd.
    Inventors: Tohru Nakao, Yasuto Morimoto, Shuzo Takehara, Hiroshi Tanaka
  • Patent number: 5162320
    Abstract: Compounds of formula I are described, ##STR1## wherein: R.sub.1 and R.sub.2, that can be the same or different, are hydrogen or acyl groups;R.sub.3 and R.sub.4, that can be the same or different, are hydrogen or optionally substituted alkyl groups.The compounds of formula I are prepared by oxydation of the compounds of formula II: ##STR2## wherein the groups R'.sub.1, R'.sub.2, R'.sub.3 and R'.sub.4 have the same meanings as R.sub.1, R.sub.2, R.sub.3 and R.sub.4 or groups convertible to the latter.The compounds of formula I have remarkable antitumor activity.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: November 10, 1992
    Assignee: Boehringer Biochemia Robin S.p.A.
    Inventors: Carmelo A. Gandolfi, Francis Johnson, Ernesto Menta, Silvano Spinelli, Sergio Tognella
  • Patent number: 5153194
    Abstract: A thienocycloheptapyridazine compound of the formula ##STR1## wherein R stands for hydrogen, a halogen or a C.sub.1-4 alkyl, Ar stands for an aryl, a heteroaryl, or an aryl or a heteroaryl having as a substituent at least a halogen, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxy, nitro, amino, hydroxy, trifluoromethyl and/or a C.sub.2-5 alkanoylamino; and the bond between 4-position and 42-position represents a single bond or a double bond, which is useful as an antianxiety agent, amnesia-treating drug, a brain function-activating drug or an antidementiac drug.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: October 6, 1992
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tohru Nakao, Hiroshi Tanaka, Yasuto Morimoto, Shuzo Takehara
  • Patent number: 5114934
    Abstract: The compounds of the formula ##STR1## wherein R.sub.a, R.sub.b, R.sub.c, R.sub.d are defined in the specification and pharmaceutically acceptable addition salts are disclosed. The compounds of formula I have valuable pharmacological properties and can be used for the control of prevention of illnesses. In particular, they have muscle relaxant, seditive-hypnotic, anxiolytic and/or anticonvulsive activity and can accordingly be used in the control or prevention of muscle tensions, stress conditions, isomnia, anxiety states and/or convulsions.
    Type: Grant
    Filed: June 1, 1989
    Date of Patent: May 19, 1992
    Assignee: Hoffman-La Roche, Inc.
    Inventors: Ulf Fischer, Fernand Schneider, Ulrich Widmer
  • Patent number: 5110924
    Abstract: The invention relates to an adduct-aldehyde of the general formula ##STR1## wherein R is a hydrogen atom or an optionally etherified or esterified hydroxy group,R.sub.1 is an optionally etherified or esterified hydroxy group, andZ is a sulphonyl group or a group of the general formula ##STR2## wherein A and B are equal or different and represent C.sub.1 -C.sub.4 alkoxy groups, or wherein A and B together constitute a phenylimino group or a o-phenylene group.The invention also relates to a method of preparing said adduct-aldehyde and to the use of said aldehyde as an intermediate for the preparation of vitamin-D compounds.
    Type: Grant
    Filed: June 12, 1990
    Date of Patent: May 5, 1992
    Assignee: Duphar International Research B.V.
    Inventors: Sebastianus J. Halkes, Wilhelmus R. M. Overbeek
  • Patent number: 5110347
    Abstract: The invention relates to certain substituted fused compounds of Formula I ##STR1## which are useful as herbicides, and their agriculturally suitable compositions, as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.
    Type: Grant
    Filed: November 26, 1990
    Date of Patent: May 5, 1992
    Assignee: E. I Du Pont de Nemours and Company
    Inventor: Thomas Selby
  • Patent number: 5110925
    Abstract: The present invention relates to a compound having the formula below which have an excellent cardiotonic action: ##STR1## wherein Y represents C.sub.1-4 alkylene which may be substituted by C.sub.1-18 alkyl, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio C.sub.1-5 alkyl, C.sub.1-5 alkoxycarbonyl or benzyl, or ##STR2## where each r.sup.1 and r.sup.2 represents hydrogen, C.sub.1-18 alkyl, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio C.sub.1-5 alkyl, C.sub.1-5 alkoxycarbonyl or benzyl); andR.sub.1 represents hydrogen, C.sub.1-5 alkyl which may be substituted by C.sub.1-5 alkoxy, acetyl or C.sub.2-5 alkenyl; andR.sub.2 represents hydrogen or methyl; andeach R.sub.3 and R.sub.4 represents hydrogen, halogen, hydroxy, C.sub.1-5 alkyl, or C.sub.1-5 alkoxy; andR.sub.5 represents hydrogen or C.sub.1-5 alkyl which may be substituted by hydroxy; andR.sub.4 and R.sub.5 may form ring by joining each other; and represents single or double bond.
    Type: Grant
    Filed: October 4, 1989
    Date of Patent: May 5, 1992
    Assignee: Nippon Soda Co., Ltd.
    Inventors: You Kusase, Masatoshi Murakata, Nobuo Mochizuki, Michinori Takebayashi
  • Patent number: 5082842
    Abstract: The compounds of the formula ##STR1## wherein Ra, Rb, Rc, Rd, Re and Rf are defined in the specification, and the pharmaceutically acceptable acid addition salts of compounds of formula A which have one or more basic substituents are described. The compounds of formula A have valuable pharmacological properties and can be used for the control or prevention of illnesses. In particular, they have muscle relaxant, sedative-hypnotic, anxiolytic and/or anticonvulsive activity and can accordingly be used in the control or prevention of muscle tensions, stress conditions, insomnia, anxiety states and/or convulsions.
    Type: Grant
    Filed: October 16, 1989
    Date of Patent: January 21, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Ulrich Widmer
  • Patent number: 5075442
    Abstract: Oxophthalazinyl acetic acids having benzothiazole side chains are prepared by reacting an oxophthalazinyl thioacetamide acetate with hydrogen sulfide and a nitrophenyl compound having a reactive group such that the benzothiazole side chain may be formed by ring closure involving the thiocaetamide group. The oxophthalazinyl thioacetamide may be prepared by reacting the corresponding cyanomethyloxophthalazinyl acetate with hydrogen sulfide in the presence of tertiary amines. Analogous indazole and oxopyridopyridazinone acetic acids may be prepared similarly, as well as oxophthalazinyl, indazole and oxopyridopyridazinone acetic acids having thiazolopyridinyl side chains.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: December 24, 1991
    Assignee: Pfizer Inc.
    Inventors: Banavara L. Mylari, William J. Zembrowski
  • Patent number: 5055580
    Abstract: Derivatives of 9-oxo-1,9a,10-triaza-9-hydroanthracene of the general formula I ##STR1## with the exception of three compounds in which R denotes a hydrogen atom, halogen atom, an alkyl-C.sub.1 -C.sub.4, alkoxy-C.sub.1 -C.sub.4 or denotes a trihalogenomethyl group, a --CO--NH.sub.2, --CO--NH--(alkyl-C.sub.1 -C.sub.4) or --CO--N(alkyl-C.sub.1 -C.sub.4).sub.2 group or phenyl, alkyl-C.sub.1 -C.sub.4, --NH.sub.2, --NH(alkyl-C.sub.1 -C.sub.4), --N(alkyl-C.sub.1 -C.sub.4).sub.2 or an alkylene-C.sub.1 -C.sub.4 --OSO.sub.3 H group, bound via the bridge member --S--, --SO--or --SO.sub.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Dietz, Frank Prokschy
  • Patent number: 5045541
    Abstract: Fused pyridazine compounds ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and respectively hydrogen, a halogen, hydroxy, nitro, amino, cyano, trifluoromethyl, and alkyl, an alkoxy or an alkanoylamino; one of R.sub.a and R.sub.b is a group of the formula--O--Y--NR.sup.5 R.sup.6wherein R.sup.5 and R.sup.6 are the same or different and respectively hydrogen, an alkyl, a phenylalkyl or a substituted phenylalkyl or a group forming a heterocycle together with the adjacent nitrogen atom and Y stands for a straight- or branched-chain alkylene which may have hydroxy group as a substituent on the chain, and the other is hydrogen, or both of R.sub.a and R.sub.b are the same or different and respectively a group of the formula--O--Y--NR.sup.5 R.sup.6wherein R.sup.5 and R.sup.6 are of the same meanings as defined above; W is .dbd.CH-- or .dbd.N; X is CH.sub.2, S, SO, SO.sub.
    Type: Grant
    Filed: July 2, 1989
    Date of Patent: September 3, 1991
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Toru Nakao, Minoru Kawakami, Masao Hisadome, Tetsuya Tahara
  • Patent number: 5037834
    Abstract: 1-Substituted-6-fluoro-7-heterocyclic-1,4-dihydroquino-1-(or dihydronaphthyridin)-4-one carboxylic acids have antibacterial properties. The 7-heterocyclic group is a bicyclic group, one of the rings of which is saturated and the other ring of which is unsaturated.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: August 6, 1991
    Assignee: Pfizer Inc.
    Inventors: Katherine E. Brighty, John A. Lowe, III, Paul R. McGuirk
  • Patent number: 5025096
    Abstract: Indole and indole derivatives are prepared by contacting under mild reaction conditions an N-(2-toly)formidate, N-(3-methyl-2-pyridyl)formimidate, or N-methyldiazyl formimidate with an alkali metal amide.
    Type: Grant
    Filed: August 22, 1985
    Date of Patent: June 18, 1991
    Assignee: Mine Safety Appliances Company
    Inventors: Kuen-Wai Chiu, Lin-Chen Yu, John R. Strickler
  • Patent number: 5011835
    Abstract: This invention is directed to a group of compounds which are acyl derivatives of amino substituted triazolopyridazines. They are prepared by the reaction of an aminotriazolopyridazine or an aminotriazolophthalazine with an appropriate acid chloride. These compounds possess bronchodilating and antiallergenic activity.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: April 30, 1991
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Norton P. Peet, Shyam Sunder
  • Patent number: 4988695
    Abstract: Pyrrolo- and dihydropyrrolocinnolines, and their use as inhibitors of gastric acid secretion. A compound of the invention is 1-(2-methylphenyl)-2,3-dihydropyrrolo-[3,2-c]-cinnoline.
    Type: Grant
    Filed: January 23, 1990
    Date of Patent: January 29, 1991
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Thomas H. Brown, Peter Blurton
  • Patent number: 4985560
    Abstract: The compound of the formula: ##STR1## in which R.sup.1 is hydrogen, alkoxy, cyano, halo, nitro, amino, or mono- or dialkylamino; R.sup.2 is hydrogen, alkyl, phenyl, benzyl, 2-thienyl, 3-thienyl or 2-,3- or 4-pyridinyl; R.sup.3 is hydrogen, alkyl or phenyl; R.sup.4 is N-methyl-pyrrolidin-2yl, 2-, 3- or 4-pyridinyl, 3-quinuclidinyl or ##STR2## where n is 1 to 5; m is 0 to 3; and R.sup.8 is hydrogen or alkyl of 1 to 6 carbon atoms; or R.sup.4 is ##STR3## wherein: (a) n is 2, R.sup.5 taken with R.sup.3 is ethylene and R.sup.6 is --CHO, alkyl, unsubstituted or substituted phenyl, pyrimidinyl, pyridinyl, or pyrazinyl, where the substituents are alkyl, alkoxyl, halo, cyano, nitro or trifluoromethyl; (b) n is 1 to 5, and R.sup.5 and R.sup.6 taken together are polymethylene which may be alkyl substituted or R.sup.5 nd R.sup.6 are morpholino, 3-azabicyclo[3.2.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: January 15, 1991
    Assignee: American Home Products Corporation
    Inventors: Annmarie L. Sabb, Magid A. Abou-Gharbia, Gervais Dionne
  • Patent number: 4983603
    Abstract: The invention relates to novel tricyclic derivatives which are agonists of cholinergic receptors.These derivatives have the formula ##STR1## in which X=O, S, --OCH.sub.2 -- or --SCH.sub.2 --; R.sub.1 =H or halogen; and R.sub.2 = ##STR2## in which Alk is an alkylene group and R.sub.3, an R.sub.4, which are identical or different, are hydrogen or a lower alkyl group, or R.sub.3 and R.sub.4, with the nitrogen atom to which they are bonded, form a 5- or 6-membered cyclic amino group optionally containing a second heteroatom; or R.sub.2 is a group ##STR3## where R.sub.5 =C.sub.1 -C.sub.4 -alkyl. Application: agonists of cholinergic receptors.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: January 8, 1991
    Assignee: Societe Anonyme: SANOFI
    Inventors: Camille G. Wermuth, Paul Worms, Jean-Jacques Bourguignon, Roger Brodin
  • Patent number: 4977152
    Abstract: The invention relates to novel tricyclic derivatives which are agonists of cholinergic receptors and to drugs containing them.These derivatives have the following formula: ##STR1## in which: X represents a group (CH.sub.2).sub.n, n representing an integer equal to 2, 3 or 4, or alternatively a vinylene group or a methylvinylene group;R.sub.1 and R.sub.2, considered independently, represent hydrogen or a substituent occupying one of the free positions of the benzene ring and selected from the group comprising halogens, a lower alkyl group, a lower alkoxy group, a hydroxyl group, a thiol group, a nitro group and an optionally substituted amino group;Y represents oxygen, sulfur or a group --NH--; andR.sub.3 is an amino groupApplication: agonists of the cholinergic receptors.
    Type: Grant
    Filed: January 25, 1990
    Date of Patent: December 11, 1990
    Assignee: Societe Anonyme: Sanofi
    Inventors: Kathleen Biziere, Camille G. Wermuth, Paul Worms, Jean-Jacques Bourguignon
  • Patent number: 4965264
    Abstract: A thienocinnoline compound of the general formula ##STR1## wherein R stands for hydrogen, a halogen or a lower alkyl, Ar stands for an aryl, a heteroaryl, or an aryl or a heteroaryl having as a substituent at least a halogen, a lower alkyl, a lower alkoxy, nitro, amino, hydroxy, trifluoromethyl and/or a lower alkanoylamino; and the bond between 5a-position and 6-position represents a single bond or a double bond, which is useful as an antianxiety agent, amnesia-treating drug, a brain function-activating drug, an antidementiac drug or a potentiating agent of biological protection.
    Type: Grant
    Filed: November 18, 1988
    Date of Patent: October 23, 1990
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Toru Nakao, Kenji Morita, Masao Hisadome, Shuzo Takehara
  • Patent number: 4960775
    Abstract: Therapeutically useful pyrrolo[2,1-a]phthalazine derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 represent cycloalkyl, optionally substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl, X represents ethylene or vinylene, R.sup.3 represents a group of the formula:--Y--CH.sub.2 --CH(OH)--CH.sub.2 --COOR.sup.5wherein Y represents carbonyl or hydroxymethylene and R.sup.5 represents hydrogen or optionally substituted alkyl, or R.sup.3 represents a lactone ring and the symbols R.sup.4 represent hydrogen, halogen, optionally substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl, or R.sup.6 O-- wherein R.sup.6 represents alkyl, aryl or arylalkyl and salts thereof, processes for their preparation and compositions containing them are described.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: October 2, 1990
    Assignee: May & Baker Limited
    Inventors: Michael J. Ashton, Andrew W. Bridge, Donald I. Dron, Garry Fenton, David J. Lythgoe, Christopher G. Newton, David Riddell, Christopher Smith, Keith A. J. Stuttle
  • Patent number: 4956460
    Abstract: A process for the preparation of 1-alkyl-3-carboxy-4-cinnolones of formula I ##STR1## wherein R and R.sub.1 are electron donor groups and R.sub.3 is an alkyl group, starting from an amine of formula II ##STR2## which is subjected to the following transformations; (1) diazotation;(2) coupling with a cyanoacetic ester;(3) alkylation of the arylhydrazone obtained in (2);(4) hydrolysis of the ester and conversion into acyl chloride;(5) intramolecular cyclization;(6) hydrolysis of the nitrile residue.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: September 11, 1990
    Assignee: Industria Chimica Profarmaco S.p.A.
    Inventors: Raffaello Fusco, Fulvio L. Piselli, Pier M. Boschi
  • Patent number: 4954629
    Abstract: Oxophthalazinyl acetic acids having benzothiazole side chains are prepared by reacting an oxophthalazinyl thioacetamide acetate with hydrogen sulfide and a nitrophenyl compound having a reactive group such that the benzothiazole side chain may be formed by ring closure involving the thioacetamide group. The oxophthalazinyl thioacetamide may be prepared by reacting the corresponding cyanomethyloxophthalazinyl acetate with hydrogen sulfide in the presence of tertiary amines. Analogous indazole and oxopyridopyridazinone acetic acids may be prepared similarly, as well as oxophthalazinyl, indazole and oxopyridopyridazinone acetic acids having thiazolopyridinyl side chains.
    Type: Grant
    Filed: May 11, 1989
    Date of Patent: September 4, 1990
    Assignee: Pfizer Inc.
    Inventors: Banavara L. Mylari, William J. Zembrowski
  • Patent number: 4954498
    Abstract: The present invention provides tricyclic benzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl radical of the general formula: ##STR2## wherein R.sub.2, R.sub.3 and R.sub.4 can be the same or diferent as in claim 1. For A, B, C and D are understood those compounds where one or two of A, B, C or D are nitrogen. These compounds are useful to inhibit the aggregation of thrombocytes and erythrocytes, lower blood pressure and can increase the power of the heart.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: September 4, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Erwin Boehm, Klaus Strein
  • Patent number: 4946955
    Abstract: A method for preparation of polycyclic 1,3-thiazolidines is described. The method comprises reacting a fluoride ion source, in a solvent, with an onium salt synthesized by the reaction of a nitrogenous heteroaromatic compound with a halomethyl trimethylsilylmethyl sulfide, the halomethyl trimethylsilylmethyl sulfide being selected from the group consisting of chloromethyl trimethylsilylmethyl sulfide, bromomethyl trimethylsilylmethyl sulfide, or iodomethyl trimethylsilylmethyl sulfide.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: August 7, 1990
    Assignee: Toray Silicone Company Limited
    Inventor: Akira Hosomi
  • Patent number: 4933276
    Abstract: A xanthine oxidase enzyme system to provide long lived entities capable of being recognized by a chemiluminescent reagent is disclosed. In the examples provided, a specific binding pair ligand or analyte is coupled with xanthine oxidase, either directly or via a streptavidin bridge. Thereafter the presence of an analyte can be determined by a chemiluminescent emission upon addition of a signal reagent comprising hypoxanthine, iron EDTA complex and luminol dissolved in barbital buffer. The resulting chemiluminescent signal is stable and detectable for many hours after initiation. The chemiluminescent xanthine oxidase system is particularly useful for immunoassays and DNA probe analysis.
    Type: Grant
    Filed: August 4, 1987
    Date of Patent: June 12, 1990
    Assignee: Canberra Industries, Inc.
    Inventor: Alain Baret
  • Patent number: 4892943
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 represent the structure ##STR2## R.sup.3 and R.sup.4 are hydrogen, or R.sup.3 and R.sup.4 taken together form a 3-5 membered saturated carbocyclic ring;R.sup.5 and R.sup.6 are hydrogen, or R.sup.5 and R.sup.6 taken together form a 3-6 membered carbocyclic ring or a cyclobutenyl ring; with the proviso that when R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are hydrogen, n is other than zero;m is 2-4;n is 0-4;X is lower alkylene, vinylene or O;R.sup.7 is unsubstituted or substituted phenyl, 2-pyridinyl, 2-pyrimidinyl, 2-pyrazinyl or 3-pyridazinyl; where the substituents are selected from the group lower alkyl, lower alkoxy, halo, cyano, nitro and trifluoromethyl;and the pharmaceutically acceptable salts thereof and their use as antipsychotic/anxiolytic agents having a low liability for extrapyramidal side effects.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: January 9, 1990
    Assignee: American Home Products Corporation
    Inventor: Magid A. Abou-Gharbia