Ring Oxygen In The Tricyclo Ring System Patents (Class 546/89)
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Patent number: 5401747Abstract: A method for synthesizing camptothecin and camptothecin analogs using a novel hydroxyl-containing tricyclic intermediate and the camptothecin analogs produced by the process. The camptothecin analogs are effective inhibitors of topoisomerase. I and show antileukemic and anti-tumor activity.Type: GrantFiled: May 31, 1994Date of Patent: March 28, 1995Assignee: Research Triangle InstituteInventors: Monroe E. Wall, Mansukh C. Wani, Allan W. Nicholas, Govindarajan Manikumar
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Patent number: 5397785Abstract: A novel 4-acylaminopyridine derivative represented by the following formula (I) is disclosed. ##STR1## The 4-acylaminopyridine derivative of the present invention is useful as a medicine for treating disturbances of memory such as senile dementia and Alzheimer's disease, since it has an action of directly activating malfunctioned cholinergic neuron.Type: GrantFiled: September 2, 1993Date of Patent: March 14, 1995Assignee: Mitsubishi Kasei CorporationInventors: Kunihiro Ninomiya, deceased, Ken-ichi Sato, Mamoru Sugano, Akihiro Tobe, Yasuhiro Morinaka, Tomoko Bessho, Haruko Harada
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Patent number: 5393890Abstract: A piperidine compound of the formula (I): ##STR1## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.dbd.CH--, --C.dbd.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.2 -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.dbd.CH--, --C.dbd.Type: GrantFiled: July 1, 1994Date of Patent: February 28, 1995Assignee: Ajinomoto Co., Inc.Inventors: Masataka Syoji, Kozo Toyota, Chikahiko Eguchi, Ryoto Yoshimoto, Yoshikatsu Koyama, Hideki Domoto, Akira Kamimura
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Patent number: 5349065Abstract: A compound represented by the following general formula (II): ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a phenyl group, a benzyl group, a phenethyl group, an alkylamine group having 1 to 4 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms, and ##STR2## represents a nobornylidene group or bicyclo [3,3,1]9-nonylidene group which may have a substituent, and ##STR3## represents a pyridine, quinoline, pyrrole or benzothiophene group which may have a substituent.Type: GrantFiled: November 17, 1992Date of Patent: September 20, 1994Assignee: Tokuyama Soda Kabushiki KaishaInventors: Takashi Tanaka, Satoshi Imura, Kenji Tanaka, Yasuji Kida
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Patent number: 5334594Abstract: Novel amphoteric tricyclic compound represented by the following formula: ##STR1## wherein R.sup.1 represents a hydrogen atom or a halogen atom; X represents --O--, --CH.sub.2 O--, or --OCH.sub.2 --; and Y represents a C.sub.2 -C.sub.5 alkylene group which may optionally be substituted with a lower alkyl group, and a pharmacologically acceptable salt thereof are disclosed. Also disclosed are a pharmaceutical composition comprising the same and a method for treatment of an allergic disease or bronchial asthma.Type: GrantFiled: February 10, 1993Date of Patent: August 2, 1994Assignee: Hokoriku Pharmaceutical Co., Ltd.Inventors: Yasuo Ito, Hideo Kato, Shingo Yasuda, Noriyuki Kado, Nobuhiko Iwasaki, Hiroyuki Nishino, Makoto Takeshita
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Patent number: 5332729Abstract: N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids of formula I ##STR1## wherein R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or heteroarylaliphatic radical having at least 2 carbon atoms,R.sub.1 is hydrogen or hydroxy,R.sub.2 is an araliphatic or heteroarylaliphatic radical substituted by free or functionally modified carboxy that is bonded directly or by way of a spacer, andR.sub.3 is hydrogen, lower alkyl or a group R.sub.2, and the salts thereof have valuable nootropic and anti-epileptic properties and can be used in the preparation of a nootropic or anti-epileptic medicament.Type: GrantFiled: May 3, 1993Date of Patent: July 26, 1994Assignee: Ciba-Geigy CorporationInventors: Stuart J. Mickel, Wolfgang Frostl, Pascal Furet
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Patent number: 5302703Abstract: The present invention is directed to novel THC derivatives which are synthesized for the covalent attachment to antigens (proteins or polypeptides) for the preparation of antibodies or receptors to the THC metabolites. The resulting novel antigens may be used for the production of antibodies or receptors using standard methods. Once generated, the antibodies or receptors and the novel derivatives which are covalently attached to proteins, polypeptides or labels may be used in the immunoassay process.Type: GrantFiled: March 17, 1993Date of Patent: April 12, 1994Assignee: Biosite Diagnostics IncorporatedInventors: Kenneth F. Buechler, Si S. Moi
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Patent number: 5298517Abstract: This disclosure describes novel imidazole compounds having the formula: ##STR1## wherein R.sup.1 and R.sup.6 are described in the specification which have activity as angiotensin II (AII) antagonists.Type: GrantFiled: October 7, 1993Date of Patent: March 29, 1994Assignee: American Cyanamid CompanyInventor: Jeremy I. Levin
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Patent number: 5281609Abstract: A novel N-methoxy-2-pyridone designated leporin A has been isolated from the sclerotia of the fungus, Aspergillus leporis. Leporin A is characterized by the structural formula ##STR1## and is effective for controlling Lepidopteran insect pests.Type: GrantFiled: September 24, 1992Date of Patent: January 25, 1994Assignees: The United States of America, as represented by the Secretary of Agriculture, University of Iowa Research FoundationInventors: Patrick F. Dowd, Donald T. Wicklow, James B. Gloer, Mark R. TePaske
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Patent number: 5276053Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.Type: GrantFiled: October 6, 1992Date of Patent: January 4, 1994Assignee: Warner-Lambert CompanyInventor: Graham Johnson
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Patent number: 5273975Abstract: Tricyclic nitrogen containing compounds, having central nervous system activity of the following structural formula: ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, C.sub.1-6 alkyl, alkenyl, or alkynyl, C.sub.3-10 cycloalkyl, or R.sub.1 and R.sub.2 are joined to form a C.sub.3-7 cyclic amine which can contain additional heteroatoms; X is hydrogen, C.sub.1-6 alkyl halogen, hydroxy, alkoxy, cyano, carboxamide, carboxyl, or carboalkoxyl; A is SO.sub.2, N, CH, CH.sub.2, CHCH.sub.3, C.dbd.O, C.dbd.S, C-SCH.sub.3, C.dbd.NH, C-NH.sub.2, C-NHCH.sub.3, C--NHCOOCH.sub.3, or C--NHCN. B is CH.sub.2, CH, C.dbd.O, N, NH or N--CH.sub.3 ; n is 0 or 1; and D is CH, CH.sub.2, C.dbd.O, O, N, NH or N--CH.sub.3. These new compounds are suitable for treating schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure in animal or human hosts.Type: GrantFiled: December 6, 1991Date of Patent: December 28, 1993Assignee: The Upjohn CompanyInventors: Malcolm W. Moon, Richard F. Heier, Jeanette K. Morris
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Patent number: 5266569Abstract: Quinolone carboxylic acids 7-substituted by azabicyclo groups have antibacterial activity.Type: GrantFiled: February 2, 1993Date of Patent: November 30, 1993Assignee: Pfizer Inc.Inventor: Katherine E. Brighty
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Patent number: 5250681Abstract: A piperidine compound of the formula (I): ##STR1## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.dbd.CH--, --C.dbd.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.2 -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.dbd.CH--, --C.dbd.Type: GrantFiled: February 15, 1991Date of Patent: October 5, 1993Assignee: Ajinomoto Co., Inc.Inventors: Masataka Shoji, Kozo Toyota, Chikahiko Eguchi, Ryota Yoshimoto, Yoshikatsu Koyama, Hideki Domoto, Akira Kamimura
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Patent number: 5247090Abstract: The present invention involves tricyclic-fused 6-member ring oxazolidinones ##STR1## which are useful as antibacterial agents.Type: GrantFiled: January 21, 1993Date of Patent: September 21, 1993Assignee: The Upjohn CompanyInventor: Steven J. Brickner
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Patent number: 5232927Abstract: There are disclosed novel compounds having the formula, ##STR1## wherein, m is an integer of 0-3;n is an integer of 1-4;R.sub.1 is hydrogen, alkyl, cycloalkyl, arylloweralkyl, aryl, naphthyl, furyl, thienyl, pyridinyl or pyrrolyl;each R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl or aryllowralkyl, or alternatively R.sub.2 and R.sub.3 taken together form a methylene or ethylene bridge;X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkoxycarbonyl, arylcarbonyl,--SH, loweralkylthio,--NHCOR.sub.4 or--NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl;Y is CH.sub.2, CH.dbd.CH, O, S or NR.sub.7, R.sub.7 being hydrogen, loweralkyl or arylloweralkyl;with the proviso that the number of said methylene or ethylene bridge shall not exceed 1 and that when Y is CH.sub.2, one and only one combination of R.sub.2 and R.sub.Type: GrantFiled: April 18, 1991Date of Patent: August 3, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Gregory M. Shutske, Kevin J. Kapples
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Patent number: 5229379Abstract: Compounds having GABA.sub.B -antagonistic properties, for example those of formula I ##STR1## wherein one of the radicals R.sub.1, R.sub.2 and R.sub.3 is hydrogen or an aliphatic, cycloaliphatic, araliphatic or aromatic radical, another is hydrogen or, in the case of R.sub.1 or R.sub.2, hydroxy or, in the case of R.sub.1, halogen or, in the case of R.sub.2 together with R.sub.2 ', oxo, and the remaining radical is hydrogen, R.sub.1 ' is hydrogen or halogen, R.sub.2 ' is hydrogen, hydroxy or, together with R.sub.2, is oxo, R.sub.4 and R.sub.5 are hydrogen or R.sub.4 is an araliphatic or heteroarylaliphatic radical and R.sub.5 is hydrogen or an aliphatic radical, and R is an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic, heteroarylaliphatic or aromatic radical having at least 2 carbon atoms or, when R.sub.1 is hydrogen or hydroxy, R.sub.2 is an aromatic radical and R.sub.1 ', R.sub.2 ' and R.sub.Type: GrantFiled: June 20, 1991Date of Patent: July 20, 1993Assignee: Ciba-Geigy CorporationInventors: Christian Marescaux, Raymond Bernasconi, Markus Schmutz, Wolfgang Frostl, Stuart J. Mickel
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Patent number: 5208330Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.Type: GrantFiled: February 25, 1992Date of Patent: May 4, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Gregory M. Shutske, Richard C. Effland
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Patent number: 5202337Abstract: The invention relates to new 7-(2,7-Diazabicyclo[3.3.0]octyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives, processes for their preparation, and antibacterial agents and feed additives containing them.Type: GrantFiled: October 3, 1991Date of Patent: April 13, 1993Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Thomas Schenke, Michael Schriewer, Klaus Grohe, Andreas Krebs, Ingo Haller, Karl G. Metzger, Klaus-Dieter Bremm, Rainer Endermann, Hans-Joachim Zeiler
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Patent number: 5202440Abstract: Compounds selected from the group consisting of 9-amino-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-2-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-8-fluoro-4-oxa-1,2,3,4-tetrahydro-acridine, 9-amino-4-oxa-1,2,3,4,5,6,7,8-octahydro-acridine or a pharmaceutical acceptable salt thereof are useful treating Alzheimer's disease.Type: GrantFiled: April 27, 1990Date of Patent: April 13, 1993Assignee: Pfizer Inc.Inventor: Manoj C. Desai
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Patent number: 5189041Abstract: 5-HT.sub.3 receptor antagonist compounds of the formula ##STR1## in which Z is --O--, --S-- or --N(R.sup.2)--; R.sup.1 and R.sup.2 are independently selected from hydrogen and lower alkyl or are together --(CH.sub.2).sub.n -- wherein n is 2 to 4; and R.sup.3 is selected from ##STR2## and the pharmaceutically acceptable salts, individual isomers, compositions, and methods of use thereof.Type: GrantFiled: November 16, 1990Date of Patent: February 23, 1993Assignee: Syntex (U.S.A.) Inc.Inventors: Jacob Berger, Robin D. Clark
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Patent number: 5180736Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.Type: GrantFiled: May 17, 1991Date of Patent: January 19, 1993Assignee: Warner-Lambert CompanyInventor: Graham Johnson
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Patent number: 5162550Abstract: Bisphthalide lactones of formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently of one another hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxy, cyano, tetrahydrofuryl or lower alkoxy; or are acyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 10 carbon atoms or unsubstituted aralkyl or aryl, or aralkyl or aryl each substituted by halogen, cyano, nitro, trifluormethyl, lower alkyl, lower alkoxy, lower alkoxycarbonyl, --NX'X"-- or 4--NX'X--"phenylamino, wherein X' and X" are each independently of the other hydrogen, lower alkyl, cyclohexyl, benzyl or phenyl, or the pairs of substituents --NR.sub.1 R.sub.2 and --NR.sub.3 R.sub.4 are each a 5- or 6-membered, preferably saturated, heterocyclic radical, V.sub.1 and V.sub.2 are hydrogen, halogen, lower alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.Type: GrantFiled: August 24, 1990Date of Patent: November 10, 1992Assignee: Ciba-Geigy CorporationInventors: Rudolf Zink, Ian J. Fletcher
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Patent number: 5144030Abstract: This disclosure related to a method and reagents for determining tetrahydrocannabinoids (THC) and THC metabolites in a biological fluid such as urine. In particular, this disclosure relates to a fluorescence polarization immunoassay procedure for determining the presence of THC and to a novel class of tracer compounds employed as reagents in such procedures. The procedure described also provides for novel wash reagent for a THC fluorescence polarization assay.Type: GrantFiled: June 12, 1989Date of Patent: September 1, 1992Assignee: Abbott LaboratoriesInventors: Nai-Yi Wang, Robert E. Dubler, Frank S. Ungemach, Roland L. Walters, Susan A. Thacker
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Patent number: 5126448Abstract: This invention relates to novel pyridine derivatives and 1,2,3,4-tetrahydropyridine derivatives shown by following general formula (I) or (II) and salts thereof which are useful as psychotropic medicaments: ##STR1## wherein A is S or O; R.sub.1 represents an unsubstituted or substituted alkoxy, amino, hydrazino, or 6- or 7-membered heterocyclic group having one or two nitrogen atoms with the proviso that R.sub.1 is not an alkoxy group in formula (I); R.sub.2 and R.sub.3 each represents a hydrogen atom or an unsubstituted or substituted alkyl, aryl, alkenyl, acyl, arylcarbonyl group; and m and n each represents an integer of from 0 to 4.Type: GrantFiled: September 29, 1989Date of Patent: June 30, 1992Assignee: Asahi Kasei Kogyo K.K.Inventors: Showa Ueki, Hiromu Kawakubo, Katsuya Okazaki, Tadashi Nagatani
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Patent number: 5112830Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridged arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.Type: GrantFiled: January 10, 1991Date of Patent: May 12, 1992Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Richard C. Effland
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Patent number: 5104876Abstract: Novel benzopyrido piperidiene, piperidylidene and piperazine compounds of the generalized formula ##STR1## are disclosed as useful for the treatment of asthma, allergy and inflammation. Novel pharmaceutical compositions containing such compounds and processes for producing the compounds are also disclosed.Type: GrantFiled: October 26, 1990Date of Patent: April 14, 1992Assignee: Schering CorporationInventors: John J. Piwinski, Jesse K. Wong, Michael J. Green, Ashit K. Ganguly, Frank J. Villani
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Patent number: 5104868Abstract: This invention relates to novel tricyclic derivatives of 7-substituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acids and certain esters and cation salts thereof. The compounds of this invention are substituted at the 7-position by vinyl, W--CH.dbd.CH--, CH.sub.3 C.tbd.C--, W--CH.sub.2 C.tbd.C-- or ##STR1## where W is selected from certain substituted alkyl groups. This invention also relates to antibacterial compositions containing the compounds and methods of using the compounds to treat bacterial disease.Type: GrantFiled: August 29, 1990Date of Patent: April 14, 1992Assignee: Pfizer Inc.Inventor: Paul R. McGuirk
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Patent number: 5098820Abstract: Solid particle dispersions of dyes according to the formula: ##STR1## are disclosed as filter dyes for photograhic elements. In this formula,m is 0 or 1.R.sub.1 and R.sub.2 are each independently substituted or unsubstituted alkyl or substituted or unsubstituted aryl, or together with R.sub.3 and R.sub.4 form a heterocyclic ring.R.sub.3 and R.sub.4 are each H or together with R.sub.1 and R.sub.2 form a heterocyclic ring.A is a ketomethylene residue.X represents a carboxyphenyl or sulfonamidophenyl, or a carboxy or sulfonamido substituent that is appended to an aryl ring that is part of A.Type: GrantFiled: May 7, 1990Date of Patent: March 24, 1992Assignee: Eastman Kodak CompanyInventors: Michael J. McManus, Donald R. Diehl, Glenn M. Brown
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Patent number: 5097044Abstract: Pyran-containing phthalides of the formula ##STR1## in which R is hydrogen, alkyl which has not more than 12 carbon atoms and is unsubstituted or substituted by halogen, cyano, hydroxyl or lower alkoxy, or is cycloalkyl, phenalkyl or phenyl each of which is unsubstituted or substituted, or an unsubstituted or substituted heterocyclic radical, R' is hydrogen, or R together with R' is C.sub.2 -C.sub.3 alkylene which is unsubstituted or substituted by methyl,X is hydrogen, alkyl having 1 to 12 carbon atoms or a monocyclic or polycyclic aromatic or heteroaromatic radical and the ring A is a benzene or naphthalene ring which is unsubstituted or monosubstituted or polysubstituted by halogen, lower alkyl, lower alkoxy or lower alkoxycarbonyl, and the ring B is an aromatic or heteroaromatic radical which has 6 ring atoms and which can contain an aromatic fused ring, it being possible for both the ring B and the fused ring to be substituted.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Rox Phaff
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Patent number: 5093339Abstract: Pyrano[f]quinoline derivatives of the formula (I): ##STR1## wherein R.sub.1 and R.sub.2 represent hydrogen, hydroxyl group or a group of the formula: ##STR2## wherein n represents an integer from 1 to 4, R.sub.3 and R.sub.4 represent hydrogen or a lower alkyl group, and the broken lines in the rings represent that the bond between the carbon atoms at the 1- and 2-positions and the bond between the carbon atoms at the 9- and 10-positions may be double bonds, and pharmaceutical compositions containing the derivatives. The derivatives and compositions are useful as anti-thrombotic agents, cerebral circulation improving agents, hypotensive agents, anti-angina agents, anti-asthmatic agents, anti-ulcer agents and anti-PAF agents.Type: GrantFiled: August 14, 1989Date of Patent: March 3, 1992Assignee: Kodama Kabushiki KaishaInventors: Toshio Kasama, Kiyoshi Mayuzumi, Ryuji Monden, Kenji Tamaru
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Patent number: 5086179Abstract: This invention is directed to certain dibenzofurancarboxamides and dibenzofurancarboxamide acids and their use as 5HT.sub.3 antagonists having unique CNS, anti-emetic and gastric prokinetic activity void of any significant D.sub.2 receptor binding properties. Further, this invention relates to a process for the synthesis of stereoisomeric compounds having such CNS, anti-emetic and gastric prokinetic activity.Type: GrantFiled: September 24, 1990Date of Patent: February 4, 1992Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Matthew R. Powers, Raymond D. Youssefyeh, William L. Studt, Frederick A. Golec
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Patent number: 5071853Abstract: A novel series of polycyclic amines, derivatives, methods of making the compounds, novel intermediates, compositions containing them, and methods for using them in the treatment and prevention of cerebrovascular disorders are disclosed.Type: GrantFiled: February 27, 1990Date of Patent: December 10, 1991Inventors: Christopher F. Bigge, Sheryl J. Hays, Graham Johnson, Perry M. Novak, Daniel F. Ortwine
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Patent number: 5070088Abstract: Novel calcium channel blockers having the formula ##STR1## wherein X is oxygen or sulfur and wherein R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6 are as defined herein, are disclosed. These compounds are useful, for example, as anti-ischemic agents.Type: GrantFiled: December 19, 1989Date of Patent: December 3, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Karnail Atwal
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Patent number: 5062881Abstract: 2-(1-Substituted-2-imidazolin-2-yl)benzoic and nicotinic acids, and derivatives thereof, which are effective in the control of undesirable plant species are described. Also described are a method for the herbicidal use of the compounds and a method for their preparation.Type: GrantFiled: December 20, 1989Date of Patent: November 5, 1991Assignee: American Cyanamid CompanyInventor: Michael A. Guaciaro
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Patent number: 5059692Abstract: Novel compounds represented by the formula: ##STR1## wherein R.sub.1 represents an alkyl group having 1 to 3 carbon atoms, R.sub.2 represents an amino group or a group of formula ##STR2## in which R.sub.4 represents an alkyl group having 1 to 3 carbon atoms, R.sub.5 represents an alkyl group having 1 to 3 carbon atoms or may combine with R.sub.6 to form a five or six membered ring containing 4 to 5 carbon atoms, R.sub.6 represents a hydrogen atom or may combine with R.sub.5 to form a five or six membered ring containing 4 to 5 carbon atoms, R.sub.3 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a halogen atom, X represents a carbonyl group or a methylene group, Y represents a sulfur atom or a vinylene group and pharmaceutically acceptable salts thereof which exhibit a vasodilating activity and inhibitory activity for platelet aggregation. Thus, they are useful as therapeutic agents for treatment of angina pectoris, hypertension, throbosis and the like.Type: GrantFiled: August 30, 1990Date of Patent: October 22, 1991Inventors: Hiroyoshi Hidaka, Tomohiko Ishikawa, Tsutomu Inoue, Masayuki Yuasa, Takashi Inaba, Kenji Naito, Osamu Sakuma, Tadashi Morita, Shinpei Kidokoro
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Patent number: 5037833Abstract: There are disclosed novel compounds having the formula, ##STR1## wherein, m is an integer of 0-3;n is an integer of 1-4;R.sub.1 is hydrogen, alkyl, cycloalkyl, arylloweralkyl, aryl, naphthyl, furyl, thienyl, pyridinyl or pyrrolyl; each R.sub.2 and R.sub.3 are independently hydrogen, loweralkyl or arylloweralkyl, or alternatively R.sub.2 and R.sub.3 taken together form a methylene or ethylene bridge;X is hydrogen, loweralkyl, cycloalkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkoxycarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.5 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl;Y is CH.sub.2, CH.dbd.CH, O, S or NR.sub.7, R.sub.7 being hydrogen, loweralkyl or arylloweralkyl; with the proviso that the number of said methylene or ethylene bridge shall not exceed 1 and that when Y is CH.sub.2, one and only one combination of R.sub.2 and R.sub.Type: GrantFiled: February 15, 1990Date of Patent: August 6, 1991Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Kevin J. Kapples
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Patent number: 5034531Abstract: Novel polycyclic pyranyl compounds, pharmaceutical compositions, and their use as anti-viral agents are disclosed.Type: GrantFiled: December 23, 1988Date of Patent: July 23, 1991Assignee: Schering CorporationInventors: Richard J. Friary, John H. Schwerdt, Ashit K. Ganguly
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Patent number: 5011845Abstract: Compounds of the formula ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group--(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar wherein Z represents O, S or --CH.sub.2 --and Ar is phenyl, optionally substituted by one or two groups selected from the group consisting of hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.2, CF.sub.3, CN, R.sup.6 -S(O).sub.x, R.sup.7 --CO--,(R.sup.8 R.sup.9)NCO-and phenyl, wherein x is 0, 1 or 2, and each R.sup.6, R.sup.7, R.sup.8 and R.sup.9 is independently C.sub.1 to C.sub.6 alkyl or two adjacent groups on Ar may form together an additional fused benzenoid ring; n and m independently represent integers of from 1 to 8; and ring Q represents one of the rings Q.sub.1, Q.sub.2, Q.sub.3 or Q.sub.4 below: ##STR2## X is N or C--R.sup.1 ; Y is N or C--R.sup.4 ;W represents O or S;each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently selected from hydrogen, C.sub.1 to C.sub.6 -alkyl, C.sub.1 to C.sub.6 -alkoxy, Cl,F,Br,I,NO.sub.Type: GrantFiled: June 13, 1990Date of Patent: April 30, 1991Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue, Ashit K. Ganguly
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Patent number: 5004813Abstract: Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.Type: GrantFiled: August 24, 1989Date of Patent: April 2, 1991Assignee: Ciba-Geigy CorporationInventors: Rox Phaff, Davor Bedekovic
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Patent number: 5001129Abstract: The present invention relates to tricyclic carbamates coplying with the formula ##STR1## in which n=0, 1 or 2,p=0 or 1,R.sub.1 represents a hydrogen atom; a group which is alkyl in C.sub.1 -C.sub.4 ; a phenyl group; a group which is alkenyl in C.sub.2 -C.sub.3 ; or a methyl group substituted by a hydroxy group, a group which is alkoxy in C.sub.1 -C.sub.4, an amino group or an N-alkylamino or N,N-dialkylamino group where the alkyl radical is in C.sub.1 -C.sub.4, andR.sub.2 represents a hydrogen atom; a halogen atom; a group which is alkyl in C.sub.1 -C.sub.4, or a group which is alkoxy in C.sub.1 -C.sub.4, and their salts of addition of acid.These compounds are therapeutically useful, notably as antidepressant agents.Type: GrantFiled: December 13, 1988Date of Patent: March 19, 1991Assignee: Delalande S.A.Inventors: Alain J. L. Renaud, Alain R. Schoofs, Jean-Marc M. Guiraudie, Denis M. Brochet
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Patent number: 4985422Abstract: Compounds which are potent and selective antagonists of the effect of 5-HT.sub.3 receptors and are useful in the treatment of psychotic disorders, anxiety, and nausea and vomiting, of the general formula (I) ##STR1## wherein Im represents an imidazolyl group of the formula (a), (b) or (c): ##STR2## one of the groups represented by R.sup.1, R.sup.2 and R.sup.3 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-6 alkenyl, phenyl or phenyl C.sub.1-3 alkyl group, and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group;n represents 1 or 2;Q represents a hydrogen atom, a halogen atom, or a hydroxy, C.sub.1-4 alkoxy, phenyl C.sub.1-3 alkoxy or C.sub.1-6 alkyl group, or a group --NR.sup.4 R.sup.5 or --CONR.sup.4 R.sup.5 ; andX represents an oxygen or a sulphur atom, and, when Im represents an imidazolyl group of formula (c), X may also represent the group NR.sup.6, where R.sup.Type: GrantFiled: April 26, 1989Date of Patent: January 15, 1991Assignee: Glaxo Group LimitedInventors: Peter C. North, Alexander W. Oxford, Ian H. Coates, Paul J. Beswick
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Patent number: 4985430Abstract: There are disclosed a 9-acylamino-tetrahydroacridine derivative represented by the following formula (I): ##STR1## wherein R ##STR2## are as defined in the specification, its optical antipode or pharmaceutically acceptable acid addition salt thereof and a memory enhancing agent containing the same as an active ingredient.Type: GrantFiled: December 2, 1988Date of Patent: January 15, 1991Assignee: Mitsubishi Kasei CorporationInventors: Shuji Morita, Ken-Ichi Saito, Kunihiro Ninomiya, Akihiro Tobe, Issei Nitta, Mamoru Sugano
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Patent number: 4973694Abstract: A 6-tertiary amino-2-(Z.dbd.CH--)benzofuran dye is disclosed, where Z represents the atoms providing an electron withdrawing group and a conjugated methine linkage completing a resonant dye chromophore including the 6-tertiary amino group as an electron donor and the electron withdrawing group as an electron acceptor. The dyes are formed by condensing a 6-tertiary amino-2-formylbenzofuran with an electron withdrawing dye nucleus precursor containing an active methyl or methylene site. The dyes exhibit bathocromically shifted absorption peaks.Type: GrantFiled: August 17, 1989Date of Patent: November 27, 1990Assignee: Eastman Kodak CompanyInventors: Chin H. Chen, John L. Fox
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Patent number: 4970316Abstract: There are disclosed compounds of the formula ##STR1## wherein X is O, S, SO, SO.sub.2 or CR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently hydrogen, lower alkyl, carboxyl, lower alkoxy carbonyl, lower cycloalkyl, phenyl, anphthyl, pyridyl, quinolinyl, pyrazinyl, pyridinyl, pyridazinyl, pyrimidinyl, quinoxalinyl, quinazolinyl or any of the foregoing aryl or hetaryl substituents substituted with halo, lower alkyl, lower alkyl carbonyl, benzoyl, COOR.sup.3, OR.sup.3, N(R.sup.3).sub.2, CON(R.sup.3).sub.2, SO.sub.3 R.sup.3, SO.sub.2 N(R.sup.3).sub.2, phenylsulfonyl, lower alkyl sulfonyl, cyano, nitro or trifluoromethyl;R.sup.3 is hydrogen, lower alkyl or phenyl;R.sup.4 is halo, morpholino, 4-methylpiperazino, R.sup.5 NNHR.sup.6, R.sup.5 NCH.sub.2 CH.sub.2 OCH.sub.3, or ##STR2## R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen, lower alkyl, lower alkanoyl, lower cycloalkyl or phenyl; andR.sup.7 and R.sup.Type: GrantFiled: May 3, 1989Date of Patent: November 13, 1990Assignee: American Home Products CorporationInventors: Jerauld S. Skotnicki, Steven C. Gilman
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Patent number: 4920226Abstract: There is provided novel (2-imidazolin-2-yl)thieno and furo compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: May 30, 1989Date of Patent: April 24, 1990Assignee: American CyanamidInventors: Marinus Los, David W. Ladner, Barrington Cross
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Patent number: 4876357Abstract: Chromogenic phthalides and azaphthalides of the formula ##STR1## in which V.sub.1 and V.sub.2 are each, independently of the other, hydrogen, halogen, lower alkyl, lower alkoxy, (lower alkoxy)carbonyl or --NR.sub.1 R.sub.2, at least one of the radicals V.sub.1 and V.sub.2 being lower alkoxy or --NR.sub.1 R.sub.2, A is an unsubstituted or halogen-, cyano-, nitro-, (lower alkyl)-, (lower alkoxy)-, (lower alkyl)thio-, (lower alkyl)amino- or di(lower alkyl)amino-substituted benzene, naphthalene, pyridine, quinoline, pyrazine or quinoxaline ring, B is a substituted phenyl radical of the formula ##STR2## or a 3-indolyl of the formula ##STR3## Q is ##STR4## --S-- or --O--, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each, independently of the others, hydrogen, unsubstituted or halogen-, hydroxy-, cyano- or (lower alkoxy)-substituted alkyl, cycloalkyl or unsubstituted or ringsubstituted phenalkyl or phenyl, or the substituent pairs (R.sub.1 and R.sub.2) and (R.sub.3 and R.sub.Type: GrantFiled: October 26, 1987Date of Patent: October 24, 1989Assignee: Ciba-Geigy CorporationInventors: Rox Phaff, Davor Bedekovic
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Patent number: 4868181Abstract: 1,4-Dihydropyridine derivatives which combine both calcium agonist and alpha.sub.1 -antagonist activity are useful in treating congestive heart failure. These derivatives are compounds having the formula: ##STR1## wherein Ar, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined in the specification.Type: GrantFiled: June 30, 1987Date of Patent: September 19, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Alexander L. Johnson, Philip Ma, Petrus B. M. W. M. Timmermans, Ruth R. Wexler
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Patent number: 4851536Abstract: There are disclosed compounds of the formula ##STR1## wherein X is O, S, SO, SO.sub.2 or CR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently hydrogen, lower alkyl, carboxyl, lower alkoxy carbonyl, lower cycloalkyl, phenyl, naphthyl, pyridyl, quinolinyl, pyrazinyl, pyridinyl, pyridazinyl, pyrimidinyl, quinoxalinyl, quinazolinyl or any of the foregoing aryl or hetaryl substituents substituted with halo, lower alkyl, lower alkyl carbonyl, benzoyl, COOR.sup.3, OR.sup.3, N(R.sup.3).sub.2, CON(R.sup.3).sub.2, SO.sub.3 R.sup.3, SO.sub.2 N(R.sup.3).sub.2, phenylsulfonyl, lower alkyl sulfonyl, cyano, nitro or trifluoromethyl;R.sup.3 is hydrogen, lower alkyl or phenyl;R.sup.4 is halo, morpholino, 4-methylpiperazino, R.sup.5 NNHR.sup.6,R.sup.5 NCH.sub.2 CH.sub.2 OCH.sub.3, or ##STR2## R.sup.5 is hydrogen or lower alkyl; R.sup.6 is hydrogen, lower alkyl, lower alkanoyl, lower cycloalkyl or phenyl; andR.sup.7 and R.sup.Type: GrantFiled: April 20, 1988Date of Patent: July 25, 1989Assignee: American Home Products CorporationInventors: Jerauld S. Skotnicki, Steven C. Gilman
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Patent number: 4845105Abstract: A compound selected from the group consisting of optical isomers and racemates of 4-hydroxy-3-quinoline carboxylates of the formula ##STR1## wherein X is in the 5-, 6-, 7- or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --SCF.sub.3 and --OCF.sub.3, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidyl and tetrazolyl, all optionally substituted with alkyl of 1 to 4 carbon atoms and phenyl and phenyl substituted with at least one member of the group consisting of --OH, alkyl and alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --NO.sub.2 and halogen, A is either ##STR2## in which R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.Type: GrantFiled: March 24, 1987Date of Patent: July 4, 1989Assignee: Roussel UclafInventors: Fran ois Clemence, Odile Le Martret, Fran oise Delevallee
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Patent number: 4843079Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1-4; R is hydrogen, loweralkyl or loweralkylcarbonyl; R.sub.1 is hydrogen, loweralkyl, loweralkylcarbonyl, aryl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, oxygen-bridge arylloweralkyl, or oxygen-bridged diaryllowerallyl; A is a direct bond or (CHR.sub.3).sub.m, m being 1-3; X is hydrogen, loweralkyl, cycloalkyl,, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, formyl, loweralkylcarbonyl, arylcarbonyl, --SH, loweralkylthio, --NHCOR.sub.4 or --NR.sub.5 R.sub.6, R.sub.4 being hydrogen or loweralkyl, and R.sub.6 and R.sub.6 being independently hydrogen, loweralkyl or cycloalkyl; Y is O, S or NR.sub.7 ; and each R.sub.2, each R.sub.3 and R.sub.Type: GrantFiled: April 4, 1988Date of Patent: June 27, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: Gregory M. Shutske, Richard C. Effland