Chalcogen Bonded Directly To Ring Carbon Of The Oxadiazole Ring Patents (Class 548/132)
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Patent number: 5631381Abstract: Process for preparing complex pesticidal 1-(haloaryl)heterocyclic compounds by reacting 1-(nitroaryl)heterocycles with metallic halide salts.Type: GrantFiled: June 28, 1996Date of Patent: May 20, 1997Assignee: Rhone-Poulenc Inc.Inventors: Jamin Huang, Scot K. Huber, Philip H. G. Smith, John H. Wilkinson
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Patent number: 5622971Abstract: A compound of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.Type: GrantFiled: June 1, 1995Date of Patent: April 22, 1997Assignee: Abbott LaboratoriesInventors: Martin Winn, Steven A. Boyd, Charles W. Hutchins, Hwan-Soo Jae, Andrew S. Tasker, Thomas W. von Geldern, Jeffrey A. Kester, Bryan K. Sorensen
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Patent number: 5602181Abstract: Naphthyl ethers of the general formula I ##STR1## where the index and the substituents have the meanings defined in the specification.Type: GrantFiled: October 12, 1994Date of Patent: February 11, 1997Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Reinhard Kirstgen, Hartmann K onig, Klaus Oberdorf, Hubert Sauter, Gisela Lorenz, Eberhard Ammermann
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Patent number: 5583141Type: GrantFiled: August 16, 1994Date of Patent: December 10, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Takehiko Naka, Yoshiyuki Inada
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Patent number: 5567725Abstract: Cyclohexanol esters of the formula I ##STR1## are described in which the radicals have the given meaning. The compounds are pharmacologically active and may therefore be used as pharmaceuticals, in particular for treating diabetes and other diseases which are characterized by an elevated secretion of glucose from the liver or by an elevated activity of the glucose-6-phosphatase system.Type: GrantFiled: February 14, 1995Date of Patent: October 22, 1996Assignee: Hoechst AktiengesellschaftInventors: Horst Hemmerle, Gerrit Schubert, Peter Below, Andreas Herling, Hans-J org Burger
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Patent number: 5547967Abstract: 3-(Phenylalkylaminoalkylozy)-heteroaryl compounds having heart rate lowering and/or anti-ischemic effects, methods for their preparation and pharmaceutical compositions containing them are described. The compounds correspond to the general formula I ##STR1## or to the general formula XXXI ##STR2## in which the substituents have the meanings given the specification.Type: GrantFiled: June 7, 1995Date of Patent: August 20, 1996Assignee: Kali-Chemie Pharma GmbHInventors: Wolfgang Kehrbach, Michael Mlinaric, Dieter Ziegler, Reinhard Brueckner, Willi Bielenberg
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Patent number: 5523312Abstract: Disclosed herein are compounds and pharmaceutical compositions useful for combating picornaviruses and preventing or treating picornaviral infections. The compounds have the formula: ##STR1## wherein Het.sub.1 is chosen from the group consisting of oxazolyl, isoxazolyl, oxadiazolyl;Y is an alkylene bridge of 3 to 9 carbon atoms;Het.sub.2 is benzofuranyl or indolyl;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, acetyl, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluromethyl, or cyano; andR.sub.3 is oxazolyl, oxadiazolyl, isoxazolyl or any of these substituted with alkyl, halo, alkoxyalkyl, cycloalkyl, haloalkyl, hydroxyalkyl, alkoxy, hydroxy, furyl, thienyl, or fluoroalkyl;the N-oxide thereof or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: September 27, 1994Date of Patent: June 4, 1996Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Gee-Hong Kuo, Theodore J. Nitz, Michael Reuman
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Patent number: 5514679Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 and R.sub.2 are independently hydrogen, halo, alkyl, alkenyl, alkoxy, hydroxy, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, alkylthioalkynyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, amino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy or cyanomethyl, nitro, difluoromethyl, trifluoromethyl or cyano;Y is alkylene of 3 to 9 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, hydroxyhaloalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkanoyl, alkanoyloxy, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, cyanomethyl, fluoroalkyl, cyano, phenyl, alkynyl, alkene, or halo;R.sub.5 is alkoxycarbonyl, alkyltetrazolyl, phenyl or a heterocycle;or a pharmaceutically acceptable acid addition salts thereof; N-oxides thereof, are useful as antipirconaviral agents.Type: GrantFiled: May 13, 1994Date of Patent: May 7, 1996Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz
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Patent number: 5510360Abstract: This invention relates to novel compounds which have demonstrated oral antihyperglycemic activity in diabetic ob/ob and db/db mice, animal models on non-insulin dependent diabetes mellitus (NIDDM ot Type II diabetes). These compounds have the formula: ##STR1## wherein: X os O or S;n is 0, 1, or 2; ##STR2## A is ##STR3## B is Y is O or S;Z is N or CH when Y is O and Z is CH when Y is S;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: April 13, 1995Date of Patent: April 23, 1996Assignee: American Home Products CorporationInventors: Michael S. Malamas, Iwan Gunawan
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Patent number: 5508450Abstract: Benzopyran derivatives which have an inhibitory effect on the Maillard reaction as well as an antioxidizing effect are described herein. These derivatives may be utilized in the treatment and/or prevention of diabetic complications such as, for example, coronary heart disease, peripheral circulatory insufficiency or failure, cerebrovascular hindrance, neurogenous diabetes, nephropathy, arteriosclerosis, arthrosclerosis, cataracts and retinopathy. Further, the derivatives may also be used in the treatment and/or prevention of diseases induced by aging and in the treatment and/or prevention of diseases caused by the formation of peroxidized fat.Type: GrantFiled: September 30, 1994Date of Patent: April 16, 1996Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Shuichi Ohuchida, Masaaki Toda, Tsumoru Miyamoto
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Patent number: 5500427Abstract: The present invention relates to a compounds represented by the following formula or salts thereof. ##STR1## The above compounds have strong angiotensin II antagonistic action, antihypertensive action and action on central nervous system, which are useful for the treatment of circulatory diseases such as hypertension, heart diseases, cerebral apoplexy, nephritis, atherosclerosis or Alzheimer's disease and senile dementia, and for agents of improving cerebral function.Type: GrantFiled: September 14, 1993Date of Patent: March 19, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Keiji Kubo, Yoshiyuki Inada, Takehiko Naka
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Patent number: 5482966Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: June 13, 1994Date of Patent: January 9, 1996Assignees: Zeneca Limited, Zeneca Pharma S.A.Inventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5480896Abstract: This invention relates to novel compounds having antihyperglycemic properties of the formula: ##STR1## where A is ##STR2## wherein:n is 1 or 2;R.sup.1 and R.sup.3 are independently hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkoxy, trifluoromethoxy, halogen or trifluoromethyl;R.sup.2 is hydrogen or methyl; andX is oxygen or sulfur or a pharmaceutically acceptable salt thereof.Type: GrantFiled: January 27, 1994Date of Patent: January 2, 1996Assignee: American Home Products CorporationInventors: Michael S. Malamas, Cynthia L. Palka, Iwan Gunawan
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Patent number: 5468762Abstract: This invention relates to compounds which have oral antihyperglycemic activity of the formula: ##STR1## wherein: R.sup.1 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl, thienyl, furyl, pyridyl, ##STR2## R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl; X os O or S;n is 0, 1, or 2;A is ##STR3## Y is O or S;Z is N or CH when Y is O and Z is CH when Y is S;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 18, 1994Date of Patent: November 21, 1995Assignee: American Home Products CorporationInventors: Michael S. Malamas, Iwan Gunawan
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Patent number: 5468857Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is a specified linking group; and A, B and E, which may be the same or different, are H, hydroxy, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; except that when Z is unsubstituted phenyl and X and K are oxygen, A, B and E are not all hydrogen.Type: GrantFiled: February 3, 1994Date of Patent: November 21, 1995Assignee: Imperial Chemical Industries PLCInventors: Alan J. Buckley, Michael G. Huchings, Ian Ferguson, Kevin Beautement, John M. Clough, Patrick J. Crowley, Christopher R. A. Godfrey, Paul J. deFraine, Vivienne M. Anthony, Stephen P. Heaney
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Patent number: 5464848Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl, hydroxyalkoxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonyl, carboxy, or cyanomethyl;Y is alkylene of 3 to 9 carbon atoms,R.sub.2 and R.sub.3 independently are hydrogen, alkyl, alkoxy, halo, cyano, trifluoromethyl and nitro;R.sub.4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, dihaloethyl, cycloalkyl, heterocyclyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, halo, thioalkyl, alkylthioalkyl, alkylthio, thio, 2,2,2-trifluoro-ethyl, (4-methylphenyl)sulfonyloxymethyl, N.dbd.Q or CON.dbd.Q, where N.dbd.Q is amino, alkylamino or dialkylamino;R.sub.5 is hydrogen or halo or alkyl.Type: GrantFiled: October 1, 1993Date of Patent: November 7, 1995Assignee: Sterling Winthrop Inc.Inventors: Guy D. Diana, Theodore J. Nitz
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Patent number: 5438066Abstract: Fungicidal and insecticidal compounds having the general formula (I): ##STR1## or a stereoisomer thereof, wherein A is CH or N; B is OCH.sub.3 or NHCH.sub.3 ; one of L and M is N and the other is S or O; X is an optionally substituted carbocyclic or heterocyclic group; and n is 0 or 1.Type: GrantFiled: October 27, 1993Date of Patent: August 1, 1995Assignee: Zeneca LimitedInventor: Ian R. Matthews
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Patent number: 5434267Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.Type: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5424443Abstract: The invention relates to new substituted benzothiazole derivatives of general formula (I), in which X, Y and Z have the meanings given in the description, processes for their preparation and their use as herbicides.Type: GrantFiled: January 24, 1994Date of Patent: June 13, 1995Assignee: Schering AktiengesellschaftInventors: Michael Ganzer, Gabriele Dorfmeister, Wilfried Franke, Gerhard Johann, Richard Rees
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Patent number: 5420146Abstract: This invention relates to novel 2-[4-(5-substituted-1,2,4-oxadiazol-3-ylmethoxy)benzyl]-1,2,5-oxadiazolidi ne-3,5-diones which have demonstrated antihyperglycemic activity in diabetic (ob/ob and db/db) mice, genetic animal models of non-insulin dependent diabetes mellitus (NIDDM or Type II diabetes). These compounds are represented by Formula I below: ##STR1## wherein R.sup.1 is C.sub.6 -C.sub.10 aryl, optionally substituted by one to three substituents independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.3 trifluoroalkyl or C.sub.1 -C.sub.3 trifluoroalkoxy; andR.sup.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, fluorine, chlorine, bromine, iodine, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.3 trifluoroalkyl, and C.sub.1 -C.sub.3 trifluoroalkoxy,or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 10, 1994Date of Patent: May 30, 1995Assignee: American Home Products CorporationInventors: Michael S. Malamas, Cynthia L. Palka, Iwan Gunawan
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Patent number: 5354766Type: GrantFiled: June 23, 1993Date of Patent: October 11, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Takehiko Naka, Yoshiyuki Inada
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Patent number: 5349068Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 is alkyl, alkoxy, hydroxy, cycloalkyl, hydroxyalkyl, alkoxyalkyl or hydroxyalkoxy;Y is alkylene of 3 to 9 carbon atoms,R.sub.2 and R.sub.3 independently are hydrogen, alkyl, alkoxy, halo, trifluoromethyl and nitro;R.sub.4 is alkoxy, hydroxy, halomethyl, dihalomethyl, trihalomethyl, cycloalkyl, alkoxycarbonyl, hydroxyalkyl, alkoxyalkyl, alkanecarbonyloxyalkyl, cyano, 2,2,2-trifluoroethyl, (4-methylphenyl)sulfonyloxymethyl, N.dbd.Q or CON.dbd.Q, where N.dbd.Q is amino, alkylamino or dialkylamino; or pharmaceutically acceptable acid-addition salts thereof are useful as antiviral agents.Type: GrantFiled: April 15, 1992Date of Patent: September 20, 1994Assignee: Sterling Winthrop Inc.Inventors: Guy D. Diana, Theodore J. Nitz
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Patent number: 5334604Abstract: There are disclosed preparative processes and hypoglycemic compounds of the formula ##STR1## wherein R is hydrogen or C1 to C3 alkyl;R.sup.1 and R.sup.2 are taken together and are carbonyl; or R.sup.1 and R.sup.2 are taken separately, wherein R.sup.1 is hydrogen or R.sup.4 and R.sup.2 is--COR.sup.5 and COOR.sup.5 ;R.sup.3, R.sup.4 and R.sup.5 are each independently C1 to C9 alkyl, C3 to C7 cycloalkyl, phenyl, naphthyl, furyl, benzofuryl or thienyl or one of said groups mono- or disubstituted with C1 to C3 alkyl, C1 to C3 alkoxy, C1 to C3 alkoxy-carbonyl, trifluoromethyl, fluoro or chloro; and n is 0 or 1; or pharmaceutically acceptable cationic salts thereof.Type: GrantFiled: February 22, 1993Date of Patent: August 2, 1994Assignee: Pfizer Inc.Inventors: Steven W. Goldstein, Ruth E. McDermott
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Patent number: 5332757Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 - which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.Type: GrantFiled: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5326776Abstract: Compounds are disclosed having the formula: ##STR1## wherein the substituents are defined herein. The compounds of the invention are angiotensin II receptor antagonists.Type: GrantFiled: February 24, 1993Date of Patent: July 5, 1994Assignee: Abbott LaboratoriesInventors: Martin Winn, Biswanath De, Thomas M. Zydowsky, Daniel J. Kerkman, John F. DeBernardis, Saul H. Rosenberg, Kazumi Shiosaki, Fatima Z. Basha, Kenneth P. Spina, Thomas W. von Geldern, Steven Boyd, Diane M. Yamamoto, Anthony K. L. Fung
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Patent number: 5324837Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Assignee: DowElancoInventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
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Patent number: 5324842Abstract: The invention relates to a process for the preparation of a compound of formula ##STR1## useful as intermediate for the preparation of pesticides, wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 10 halogen atoms or by from 1 to 3 radicals selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio and phenyl, phenyl or phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, which comprises reacting with hydrazine hydrate a compound of formula ##STR2## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 9 chlorine atoms, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.Type: GrantFiled: December 16, 1992Date of Patent: June 28, 1994Assignee: Ciba-Geigy CorporationInventors: Ernst Beriger, Haukur Kristinsson
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Patent number: 5294596Abstract: The invention relates to novel heterocyclyltriazolinones of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or represents alkyl or cycloalkyl, each of which is optionally substituted,R.sup.2 represents hydrogen, hydroxyl, mercapto or halogen or represents alkyl, alkenyl, alkinyl, cycloalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, arylalkyl, amino or heterocyclyl, each of which is optionally substituted, andHet represents an optionally substituted heterocycle of the formula ##STR2## in which X in each case represents oxygen, sulphur, an NH group or an N-alkyl group,a process for their preparation and their use as herbicides.Type: GrantFiled: July 21, 1993Date of Patent: March 15, 1994Assignee: Bayer AktiengesellschaftInventors: Wilhelm Haas, Kurt Findeisen, Karl-Heinz Linker, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 5283363Abstract: The invention relates to a new process for the preparation of (hetero)arylalk(en/in)ylamines of the formula (I) ##STR1## in which A represents ethane-1,2-diyl (ethylene, dimethylene, --CH.sub.2 --CH.sub.2 --) or represents ethene-1,2-diyl (ethenylene, vinylene, --CH.dbd.CH--) or represents ethine-1,2-diyl (ethinylene, --C.ident.C--),characterized in that(a) in the event that, in formula (I), A represents ethine-1,2-diyl, halogeno(hetero)aryl compounds of the general formula (II)Ar--X (II)are reacted with aminoalkinyl compounds of the general formula (III) ##STR2## and, if appropriate, (b) in the event that, in formula (I), A represents ethane-1,2-diyl or ethene-1,2-diyl, the new (hetero)aralkinylamines which are obtained by the process step described under (a), of the general formula (Ia), ##STR3## are reacted with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, the definitions applying to Ar, R.sup.1, R.sup.Type: GrantFiled: January 16, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Dietmar Kuhnt, Thomas Himmler, Heinz Ziemann
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Patent number: 5276037Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.Type: GrantFiled: April 14, 1993Date of Patent: January 4, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5274104Abstract: The present invention relates to N-substituted heterocyclic derivatives of formula: ##STR1## processes for their preparation, and pharmaceutical compositions which contain them. The compounds according to the invention are non-peptide compounds which oppose the action of angiotensin II. The compounds according to the invention are thus useful in the treatment of cardiovascular disorders such as hypertension and heart failure.Type: GrantFiled: June 19, 1992Date of Patent: December 28, 1993Assignee: Elf Sanofi, A French Corp.Inventors: Joelle Arnaud, Jean-Louis Assens, Claude Bernhart, Bernard Ferrari, Frederique Haudricourt, Pierre Perreaut
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Patent number: 5268375Abstract: This invention relates to compounds of formula ##STR1## in which: R.sub.1 and R.sub.2 are similar or different and are each independently hydrogen or a group selected from CO.sub.2 N.dbd.C(NH.sub.2).sub.2, CONHNHCONH.sub.2, CONHNHCSNH.sub.2, C(OC.sub.2 H.sub.5).dbd.NCO.sub.2 CH.sub.3, COCH.sub.2 CO.sub.2 H.sub.5, N(OH)-CONHCOOC.sub.2 NCO.sub.2 CH.sub.3, COCH.sub.2 CO.sub.2 H.sub.5, N(OH)-CONHCOOC.sub.2 H.sub.5, C(OC.sub.2 H.sub.5).dbd.NH or a nitrogen heterocycle; with the proviso that at least one of the substituents R.sub.1 or R.sub.2 is other than hydrogen;R.sub.3 is a hydrogen, a C.sub.1 -C.sub.6 alkyl, a C.sub.2 -C.sub.6 alkenyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl, a phenylalkyl, or a phenylalkenyl;R.sub.4 and R.sub.5 are each independently a C.sub.1 -C.sub.6 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl or a phenylalkyl; orR.sub.4 and R.sub.5, bonded together, are either a group of the formula (CH.sub.2).sub.n or a group of the formula (CH.sub.2).sub.p Y (CH.sub.2).sub.Type: GrantFiled: February 28, 1992Date of Patent: December 7, 1993Assignee: Elf SanofiInventors: Claude Bernhart, Bernard Ferrari, Pierre Perreaut
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Patent number: 5256632Abstract: Herbicidal sulphonylated carboxamides of the formulaR.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)in whichn represents the numbers 0 or 1,A represents oxygen, iminio (NH) or methylene (CH.sub.2),R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, andR.sup.2 represents aryl or heteroaryl which are in each case optionally substituted,or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.Type: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5256680Abstract: The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.Type: GrantFiled: June 29, 1992Date of Patent: October 26, 1993Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Michael D. Mullican, Gary P. Shrum, Paul C. Unangst, Michael W. Wilson
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Patent number: 5243054Type: GrantFiled: June 25, 1992Date of Patent: September 7, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Takehiko Naka, Yoshiyuki Inada
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Patent number: 5242890Abstract: The present invention relates to 1,2,4-oxadiazole derivative of the formula (I) ##STR1## wherein X represents a chlorine or fluorine atom or methyl group,Y represents a chlorine or fluorine atom,n is an integer of 1 or 3.The compounds of the invention have a extremely high selectively between paddy rice or crop plants and weeds, and a strong activity on various weeds. Moreover, the compounds have a very low phytotoxicity to paddy rice and crop plants.Type: GrantFiled: February 3, 1992Date of Patent: September 7, 1993Assignee: Korea Research Institute of Chemical TechnologyInventors: Kwang Y. Cho, In H. Jeong
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Patent number: 5240946Abstract: A compound of the formula: ##STR1## in which R.sup.1 is hydrogen, alkyl or phenylalkyl; R.sup.2 is hydrogen, alkyl, alkenyl or phenylalkyl; or R.sup.1 and R.sup.2 taken together are --CH.sub.2 CH.sub.2 --, --CH.sub.2 C(R.sup.6)(R.sup.7)CH.sub.2 -- or --CH.sub.2 C(R.sup.8)(R.sup.9)--C(R.sup.10)(R.sup.11)CH.sub.2 --, where R.sup.6, R.sup.8 and R.sup.10 are, independently, hydrogen, alkyl of 1 to 6 carbon atoms or hydroxyl and R.sup.7, R.sup.9 and R.sup.11 are, independently, hydrogen or alkyl of 1 to 6 carbon atoms; A is alkylene or alkenylene; X is CO.sub.2 R.sup.3 in which R.sup.3 is hydrogen or alkyl, P(O)(OR.sup.4)(OR.sup.5) in which R.sup.4 and R.sup.5 are, independently, hydrogen or alkyl, 3,5-dioxo-1,2,4-oxadiazolidin-2-yl or 5-tetrazolyl; or a pharmaceutically acceptable salt thereof are useful as neuroprotectants.Type: GrantFiled: April 29, 1992Date of Patent: August 31, 1993Assignee: American Home Products CorporationInventors: William A. Kinney, Deanna C. Garrison
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Patent number: 5223616Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.Type: GrantFiled: November 4, 1991Date of Patent: June 29, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
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Patent number: 5221684Abstract: Hydroquinone diethers of the formula I ##STR1## where A.sup.1 and A.sup.2 are substituted or unsubstituted alkylene;R.sup.1 is hydrogen, halogen or alkyl;R.sup.2 is substituted or unsubstituted pyrazolyl or pyridyl;X is a substituted or unsubstituted 5-membered heteroaromatic radical, are prepared as described using the described intermediates, and are used as pesticides.Type: GrantFiled: October 8, 1991Date of Patent: June 22, 1993Assignee: BASF AktiengesellschaftInventors: Christoph Nuebling, Hans Theobald, Wolfgang Krieg, Uwe Kardorff, Christoph Kuenast
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Patent number: 5210204Abstract: Heterocyclic methyl derivatives of biphenyl oxadiazoles and thiadiazoles are described, as well as methods for the preparation of said derivatives and pharmaceutical compositions of the same, which are useful as antagonists of the angiotensin II enzyme and thus useful in treating hypertension, hyperaldosteronism, congestive heart failure, and glaucoma.Type: GrantFiled: June 16, 1992Date of Patent: May 11, 1993Assignee: Warner-Lambert CompanyInventors: David T. Connor, Catherine R. Kostlan
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Patent number: 5208248Abstract: A class of indazole-substituted five-membered heteroaromatic compounds are specific agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.Type: GrantFiled: July 16, 1991Date of Patent: May 4, 1993Assignee: Merck Sharpe & Dohme, Ltd.Inventors: Raymond Baker, Mark S. Chambers, Leslie J. Street
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Patent number: 5207816Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a substituted or unsubstituted five-membered heteroaromatic radical, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, processes for their manufacture, and the use of these compounds for controlling undesirable plant growth.Type: GrantFiled: June 6, 1991Date of Patent: May 4, 1993Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
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Patent number: 5185353Abstract: A method for killing or controlling nematode pests which comprises applying to the locus of the pests or to a plant susceptible to attack by the pest an effective amount of a compound of formula (I): ##STR1## wherein R.sup.1 is an optionally substituted aryl or optionally substituted heterocyclic group and novel compounds of formula (I) where R.sup.1 is not phenyl.Type: GrantFiled: November 8, 1990Date of Patent: February 9, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Turnbull, Robert W. Parsons, Andrew D. S. Watkins
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Patent number: 5124460Abstract: A process for preparing a substantially pure enantiomer of a compound formula (I) ##STR1## wherein X is O or S; andR.sup.2 represents hydrogen, --CF.sub.3, --OR.sup.7, --SR.sup.7, --NR.sup.7 R.sup.8, --CN, --COOR.sup.7, --CONR.sup.7 R.sup.8, or a saturated or unsaturated, substituted or unsubstituted hydrocarbon group, wherein R.sup.7 and R.sup.8 are independently selected from hydrogen and C.sub.1-2 alkyl provided that --NR.sup.7 R.sup.8 is other than NH.sub.2 ;which process comprises cyclization of a compound of formula (10) or salt thereof: ##STR2## wherein X and R.sup.2 are as defined in formula (I); and R.sup.4 is a labile leaving group and optionally epimerizing the endo-diastereomer so prepared to produce the corresponding exo-diastereomer.Type: GrantFiled: May 6, 1991Date of Patent: June 23, 1992Assignee: Merck Sharp & Dohme Ltd.Inventor: Guy R. Humphrey
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Patent number: 5114958Abstract: 1,2,4-Oxadiazole and 1,2,4-thiadiazole derivatives of the fenamic acids, in which the fenamate residue is present at the 3-position of the 1,2,4-oxadiazole or 1,2,4-thiadiazole, pharmaceutically acceptable acid addition or base salts and methods of preparation for such compounds as well as pharmaceutical compositions alone or in combination with a second active ingredient are described. The compounds are active as inhibitors of cyclooxygenase and/or 5-lipoxygenase thereby providing methods of treatment for antiinflammatory diseases.Type: GrantFiled: May 9, 1991Date of Patent: May 19, 1992Assignee: Warner-Lambert CompanyInventors: Diane H. Boschelli, David T. Connor
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Patent number: 5101034Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.Type: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5066662Abstract: Oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones substituted in the 4-position of the oxazolidin-2-one ring and the 3-position of the 1,2,4-oxadiazolin-5-one ring with a 5- or 6-member heteroaromatic, a bicyclic heteroaromatic group or a 5- or 6-member heterocyclic group either directly or via a one or two carbon bridge and derivatives thereof are described, as well as methods for the preparation and pharmaceutical compositions of same, which are useful as centrally acting muscarinic agents and are useful as analgesic agents for the treatment of pain, as sleep aids and as agents for treating the symptoms of senile dementia, Alzheimer's disease, Huntington's chorea, tardive dyskinesia, hyperkinesia, mania, or similar conditions of cerebral insufficiency characterized by decreased cerebral acetycholine production or release.Type: GrantFiled: May 21, 1990Date of Patent: November 19, 1991Assignee: Warner-Lambert CompanyInventors: Sheila H. Hobbs, Stephen J. Johnson
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Patent number: 4996325Abstract: Novel substituted N-amino-1,2,4-triazinones of formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.2 haloalkyl, phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl, or a phenyl, benzyl, phenethyl, phenpropyl, phenbutyl or phenpentyl radical that is mono- or di-substituted by halogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.2 haloalkyl, methoxy and/or by ethoxy,R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, or is phenyl that is unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl, halogen or by C.sub.1 -C.sub.12 haloalkyl, or R.sub.1 and R.sub.2 together form a saturated or unsaturated 3- to 7-membered carbocycle,R.sub.3 is hydrogen or C.sub.1 -C.sub.6 alkyl andZ is --N.dbd.CH-- or --NH--CH.sub.Type: GrantFiled: March 13, 1990Date of Patent: February 26, 1991Assignee: Ciba-Geigy CorporationInventor: Haukur Kristinsson
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Patent number: 4988718Abstract: Fungicidal substituted 4-heterocyclyloximinopyrazolin-5-ones of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another in each case represent hydrogen, alkyl, alkenyl, alkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonyl, hydroxycarbonylalkyl, alkoxycarbonylalkyl, aminocarbonylalkyl, alkylaminocarbonylalkyl or dialkylaminocarbonylalkyl, or represent in each case unsubstituted or in each case substituted oxiranylalkyl, aralkyl, heterocyclyl or aryl andHet represents an unsubstituted or substituted heterocycle.Type: GrantFiled: August 9, 1990Date of Patent: January 29, 1991Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Klaus Jelich, Gerd Hanssler
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Patent number: 4988706Abstract: Novel compounds of formula (I), processes for their preparation, and their use as pharmaceutical agents are described: ##STR1## in which X represents a group ##STR2## wherein one of Y and Z represents nitrogen and the other represents CR where R is selected from halogen, CN, OR.sup.1, SR.sup.1, N(R.sup.1).sub.2, NHR.sup.1, NHCOR.sup.1, NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHOR.sup.1, NHNH.sub.2, COR.sup.1, COR.sup.2, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl or C.sub.1-2 alkyl substituted with OR.sup.1, N(R.sup.1).sub.2, SR.sup.1, CO.sub.2 R.sup.1, CON(R.sup.1).sub.2 or one or two halogen atoms, in which R.sup.1 is hydrogen or C.sub.1-2 alkyl and R.sup.2 is OR.sup.1, NH.sub.2 or NHR.sup.1 ; and each of p and q independently represents an integer of 2 to 4.Type: GrantFiled: April 13, 1989Date of Patent: January 29, 1991Assignee: Beecham Group P.L.C.Inventors: Michael S. Hadley, Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth