Carbonyl, Sulfur, Or Cyano Attached Directly To Thiourea Nitrogen By Nonionic Bonding Patents (Class 564/23)
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Patent number: 5096928Abstract: Insecticidal substituted benzoyl(thio) ureas of the formula ##STR1## in which Q stands for oxygen or sulphur,R.sup.1 stands for hydrogen, halogen, nitro, methyl or trifluoromethyl,R.sup.2 stands for hydrogen, fluorine or chlorine,R.sup.3 stands for hydrogen, fluorine or chlorine,R.sup.4 stands for hydrogen or fluorine,R.sup.5 stands for hydrogen or halogen andn stands for the numbers 2, 3 or 4.Intermediates of the formula ##STR2## are also new.Type: GrantFiled: September 24, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Albrecht Marhold, Benedikt Becker, Wilhelm Stendel
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Patent number: 5001157Abstract: New substituted N-[[2-(aminocarbonyl)phenylamino]-thioxomethyl]benzamides which are useful as congnition stimulators in mammals.Type: GrantFiled: February 2, 1989Date of Patent: March 19, 1991Assignee: American Cyanamid CompanyInventors: William J. Fanshawe, Joseph W. Epstein
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Patent number: 4971994Abstract: Novel N-phenyl-N-carbonylthioureas of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.10 alkyl, phenyl-C.sub.1 -C.sub.7 alkyl; C.sub.1 -C.sub.10 alkyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; C hd 3-C.sub.8 cycloalkyl which is monosubstituted or polysubstituted by halogen or C.sub.1 -C.sub.5 alkyl; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 is C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, phenyl, phenyl-C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.8 cycloalkyl; C.sub.1 14 C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl or phenyl-C.sub.1 -C.sub.7 alkyl each of which is monohalogenated or polyhalogenated or interrupted once or more than once by oxygen and/or sulfur; C.sub.3 -C.sub.8 cycloalkyl; phenyl or C.sub.3 -C.sub.8 cycloalkyl each of which is monosubstituted or polysubstituted by halogen or C.Type: GrantFiled: April 11, 1989Date of Patent: November 20, 1990Assignee: Ciba-Geigy CorporationInventors: Jozef Drabek, Manfred Boger, Josef Ehrenfreund
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Patent number: 4954529Abstract: Compounds of the general formula I ##STR1## in which A denotes a radical of the formula A.sup.1, A.sup.2 or A.sup.3 ##STR2## R.sup.1 to R.sup.3 in each case independently of one another denote hydrogen or halogen,the radicals R.sup.4 in each case independently of one another denote halogen, (C.sub.1 -C.sub.3)halogenoalkyl or nitro,R.sup.5 denotes (C.sub.1 -C.sub.5)alkyl, which can be halogenated,X denotes oxygen or sulfur,n denotes a number from 0 to 2 andm denotes a number from 1 to 4 with the proviso that (R.sup.4).sub.m does not by itself denote halogen or by itself denote nitro, and where A=A.sup.1, salts thereof which can be used in agriculture, have advantageous acaricidal and insecticidal properties.Processes for the preparation of the compounds of the formula I are furthermore described.Type: GrantFiled: December 2, 1988Date of Patent: September 4, 1990Assignee: Hoechst AktiengesellschaftInventors: Volker Koch, Stefan Schnatterer, Werner Bonin, Manfred Kern, Werner Knauf, Anna Waltersdorfer
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Patent number: 4873264Abstract: Novel 1-(alkylphenoxyphenyl)-3-benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal composition.Type: GrantFiled: March 7, 1988Date of Patent: October 10, 1989Assignee: Rhone-Poulenc Nederlands B.V.Inventors: David T. Chou, Paul A. Cain
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Patent number: 4868215Abstract: N-aroyl N'-phenyl ureas having the formula ##STR1## wherein: Ar is a substituted phenyl, pyridyl or pyrimidinyl radical wherein the substituents are chloro, bromo, fluoro C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, with the proviso that at least one substituent is positioned ortho to the carbonyl group; R.sub.3 and R.sub.4 are individually H or C.sub.1 -C.sub.4 alkyl or together they form the group ##STR2## Y is O or S; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are individually H, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, alkylcarbonyl, alkoxycarbonyl, C.sub.1 -C.sub.3 alkylthio, NO.sub.2, CN or NR.sub.5 R.sub.6 wherein R.sub.5 and R.sub.6 are H or C.sub.1 -C.sub.3 alkyl with the provisos that at least one of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is other than H and (a) when three of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 are H, the fourth substitution cannot be halogen or alkyl, (b) when X.sub.1 and X.sub.3 are H, X.sub.2 and X.sub.4 cannot both be halogen, (c) when X.sub.2 and X.sub.Type: GrantFiled: September 24, 1984Date of Patent: September 19, 1989Assignee: The Dow Chemical CompanyInventors: Barat Bisabri-Ershadi, Raymond H. Rigterink
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Patent number: 4782091Abstract: Arthropodicidally active novel benzoyl(thio)ureas of the formula ##STR1## in which X is oxygen or sulphur,R.sup.1 is halogen andR.sup.2 is halogen.Type: GrantFiled: November 10, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehen, Wilhelm Stendel
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Patent number: 4782090Abstract: Arthropodicidally active novel benzoyl(thio)ureas of the formula ##STR1## in which X is oxygen or sulphur, andR.sup.1 and R.sup.2 each independently is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl.Type: GrantFiled: November 16, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Benedikt Becker, Wolfgang Behrenz, Ingomar Krehan, Wilhelm Stendel
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Patent number: 4774260Abstract: 1-Phenyl-3-benzoyl-(thio)ureas of the formula ##STR1## in which X represents oxygen or sulphur,R.sup.1 represents hydrogen, halogen, nitro, alkyl or alkylthio,R.sup.2, R.sup.4 and R.sup.5 are identical or different and represent hydrogen or halogen,R.sup.3 represents hydrogen, halogen or nitro,R.sup.6 and R.sup.7 are identical or different and represent hydrogen, halogen or alkyl,R.sup.8 and R.sup.9 are identical or different and represent hydrogen or halogen andR.sup.10 represents halogenoalkylthio or halogenoalkoxy,with certain exclusions, which possess insecticidal and acaricidal activity.Type: GrantFiled: March 24, 1986Date of Patent: September 27, 1988Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Benedikt Becker, Ingomar Krehan, Wilhelm Stendel
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Patent number: 4734436Abstract: Disclosed is a compound of the formula: ##STR1## wherein X.sub.1 and X.sub.3 represent chloro or fluoro, X.sub.2 represents hydrogen, chloro or fluoro, X.sub.4 represents hydrogen or halogen, X.sub.5 represents --CF.sub.3 or --OCF.sub.3, Y represents oxygen or sulfur and an insecticidal composition containing said compound, a method for killing insect pests and a process for producing said compound and its use as pesticide.Type: GrantFiled: December 9, 1985Date of Patent: March 29, 1988Assignee: Nippon Kayaku Kabushiki KaishaInventors: Akira Kurozumi, Satoshi Ototake, Hitoshi Sato, Satoshi Tanabe, Tatsumi Hayaoka, Akio Masui
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Patent number: 4713396Abstract: A compound having the formula ##STR1## wherein R.sub.1 represents halogen or methyl;R.sub.2 represents hydrogen or halogen;each of R.sub.3 and R.sub.4 represents halogen; andeach of X and Y represents oxygen or sulfur.The compound is useful as insecticide.Type: GrantFiled: September 9, 1985Date of Patent: December 15, 1987Assignee: Nippon Soda Co., Ltd.Inventors: Katsuyata Ikura, Kenji Hagiwara, Fumihiko Nagasaki, Tomio Yamada, Hidemitsu Takahashi, Renpei Hatano
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Patent number: 4665097Abstract: Novel bicyclooxyaryl thioureas are provided together with methods for their preparation and use as the active toxicant in pesticidal compositions.Type: GrantFiled: March 31, 1983Date of Patent: May 12, 1987Assignee: Union Carbide CorporationInventor: Paul A. Cain
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Patent number: 4638088Abstract: Novel biphenylyloxy and biphenylylalkoxy aryl acyl urea compounds are provided together with methods for their preparation and the use of said compounds as the active toxicant in pesticidal compositions.Type: GrantFiled: November 15, 1984Date of Patent: January 20, 1987Assignee: Union Carbide CorporationInventors: David T. Chou, Robert C. Ligon
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Patent number: 4622340Abstract: This invention relates to compounds of the formula ##STR1## Z' is chlorine or fluorine, with the proviso that Z' is chlorine when Q is the moiety of Formula III. The invention also relates to the preparation of the compounds, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds as active ingredients.Type: GrantFiled: April 26, 1984Date of Patent: November 11, 1986Assignee: Celamerck GmbH & Co., KGInventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
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Patent number: 4613356Abstract: Substituted aryloxyphenoxy propionyl thiourea compounds useful as herbicides, and their methods of use, a representative one of which has the structural formula ##STR1## The method comprises applying the above referenced compound to the locus where control is desired.Type: GrantFiled: August 6, 1984Date of Patent: September 23, 1986Assignee: Stauffer Chemical CompanyInventor: Ferenc M. Pallos
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Patent number: 4602109Abstract: Novel phenoxyphenyl and phenoxypyridyl benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal compositions.Type: GrantFiled: December 27, 1984Date of Patent: July 22, 1986Assignee: Union Carbide CorporationInventors: David T. Chou, John A. Durden, Themistocles D. J. D'Silva
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Patent number: 4571266Abstract: There is described a process for the separation and purification of the platinum group metals from base metal out of acidic aqueous solutions. For this purpose there is used a substituted thiourea of the formulaR.sub.1 R.sub.2 N--CS--NH--CO--R.sub.3orR.sub.1 R.sub.2 N--CS--NH--COOR.sub.3as the extraction agent. Preferably there are employed N,N-dialkyl-N'-benzoylthiourea wherein R.sub.1 and R.sub.2 are methyl, n-butyl, or n-hexyl.Type: GrantFiled: November 2, 1984Date of Patent: February 18, 1986Assignee: Degussa AktiengesellschaftInventors: Karl-Heinz Konig, Michael Schuster, Gerd Schneeweis, Bernd Steinbrech, Rainer Schlodder
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Patent number: 4571265Abstract: There is described a process for the separation and purification of the platinum group metals from base metal out of acidic aqueous solutions. For this purpose there is used a substituted thiourea of the formulaR.sub.1 R.sub.2 N--CS--NH--CO--R.sub.3orR.sub.1 R.sub.2 N--CS--NH--COOR.sub.3as the precipitation agent. Preferably there are employed N,N-diaklyl-N'-benzoylthiourea wherein R.sub.1 and R.sub.2 are methyl, n-butyl, or n-hexyl.Type: GrantFiled: November 2, 1984Date of Patent: February 18, 1986Assignee: Degussa AktiengesellschaftInventors: Karl-Heinz Konig, Michael Schuster, Dieter Hollmann, Rainer Schlodder
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Patent number: 4562210Abstract: Novel N-[2-(1,2-dichlorovinyloxy)phenylsulfonyl]-(thio)ureas of the general formula I ##STR1## in which X is oxygen or sulfur, R.sub.1 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkinyl; and R.sub.2 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkinyl or C.sub.1 -C.sub.6 -alkoxy; and the salts of these compounds are described.These compounds have pronounced bactericidal properties and can be used without problems against bacteria which damage plants, especially in the agricultural sector.Type: GrantFiled: December 21, 1983Date of Patent: December 31, 1985Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner Topfl, Haukur Kristinsson, Wolfgang Eckhardt
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Patent number: 4560751Abstract: Compounds of the general formula I ##STR1## where R is unsubstituted or substituted alkyl, alkenyl, aryl or hetaryl and R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted alkyl or aryl, or, together with the nitrogen, form a heterocyclic ring, are prepared by a process wherein a compound of the general formula II ##STR2## is reacted with a water-soluble monohaloacetate in an aqueous alkaline medium. They are very useful coupling components for the preparation of azo dyes.Type: GrantFiled: June 30, 1983Date of Patent: December 24, 1985Assignee: BASF AktiengesellschaftInventor: Guenther Seybold
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Patent number: 4550202Abstract: The invention relates to new benzoylurea compounds of the general formula ##STR1## wherein R.sub.1 is a halogen atom,R.sub.2 is a hydrogen atom or a halogen atom,R.sub.3 is a hydrogen atom or represents 1 or 2 substituents which are selected from the group consisting of chlorine, methyl and trifluoromethyl,R.sub.4 is a hydrogen atom, an alkyl group having 1-6 carbon atoms or a cycloalkyl group having 3-6 carbon atoms,R.sub.5 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, andA is a phenyl group or a heteroaryl group having 1 or 2 nitrogen atoms, which groups may be substituted with 1-3 substituents which are selected from the group consisting of halogen, and alkyl, alkoxy, haloalkyl and haloalkoxy having 1-4 carbon atoms.The compounds have an insecticidal and acaricidal activity. After having been processed to compositions, the compounds may be used for control of insects and/or mites in a dosage from 1 to 5000 g of active substance per hectare.Type: GrantFiled: January 19, 1984Date of Patent: October 29, 1985Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4537620Abstract: Substituted aryloxyphenoxy acylisothioureas useful as herbicides having the formula ##STR1## wherein R is CF.sub.3 or halogen; X is hydrogen or halogen; A is CH or nitrogen; R.sub.1 is hydrogen, lower alkyl, alkenyl, alkynyl, phenyl, cyanoalkyl, alkoxyalkyl, or alkoxycarbonylalkyl; R.sub.2 is hydrogen, lower alkyl, phenyl, or substituted phenyl; and R.sub.3 is acyl or halogen substituted acyl selected from the group consisting of propionyl, dichloro bromoacetyl, propionaminocarbonyl and phenylaminocarbonyl.Type: GrantFiled: July 2, 1984Date of Patent: August 27, 1985Assignee: Stauffer Chemical CompanyInventor: Ferenc M. Pallos
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Patent number: 4533676Abstract: A 2,5-dihalogenobenzoyl-(thio)urea of the formula ##STR1## in which X represents sulphur or oxygen,X.sup.1 and X.sup.2 are identical or different and represent fluorine, chlorine, bromine or iodine,R.sup.1 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkoxy and alkylthio,R.sup.2 represents hydrogen, halogen, cyano, nitro or optionally substituted radicals from the series comprising alkyl, alkylthio, alkylsulphonyl, alkoxy, aryloxy, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl and alkoxycarbonylalkylthio,R.sup.1 and R.sup.2 together represent an optionally substituted alkylenedioxy radical or represent --CF.sub.2 --O--CF.sub.2 --O--,R.sup.3 represents hydrogen, halogen, or an optionally substituted alkyl, alkoxy or aryloxy radical, andR.sup.4 represents hydrogen, halogen, or optionally substituted radicals from the series comprising alkyl, alkylthio and alkoxy, with the exception of those cases in which X represents oxygen, X.sup.1 and X.sup.Type: GrantFiled: April 22, 1983Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann
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Patent number: 4468405Abstract: Novel N-aroyl N'-phenyl ureas having halogen substituents in the 3- and 5-positions and haloalkyl, haloalkoxy or haloalkylthio in the 4-position of the N'-phenyl are more active and have a broader spectrum of effectiveness than the known benzoylurea insecticides.Type: GrantFiled: July 26, 1982Date of Patent: August 28, 1984Assignee: The Dow Chemical CompanyInventors: Raymond H. Rigterink, Ronald J. Sbragia
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Patent number: 4457943Abstract: This invention relates to compounds of the formula ##STR1## wherein ##STR2## X is oxygen or sulfur; Y is chlorine or fluorine; andZ is hydrogen, chlorine, or fluorine,as well as to the preparation thereof, their use in controlling animal pests in plant protection, and pesticidal agents comprising the compounds of Formula I as active ingredients.Type: GrantFiled: November 16, 1981Date of Patent: July 3, 1984Assignee: Celamerck GmbH & Co. KGInventors: Heinz-Manfred Becher, Ricarda Prokic-Immel, Walter Wirtz
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Patent number: 4350706Abstract: The invention relates to new urea and thiourea compounds as insecticides.The compounds, after having been processed to compositions, can successfully be used to control insects in a dosage from 10 to 5000 g of active substance per hectare.Type: GrantFiled: June 27, 1979Date of Patent: September 21, 1982Assignee: Duphar International Research B.V.Inventors: Marius S. Brouwer, Arnoldus C. Grosscurt
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Patent number: 4321083Abstract: Compounds having the formula ##STR1## in which R is alkyl having 1-4 carbon atoms and have utility for the protection of crops from herbicidal injury.Type: GrantFiled: April 21, 1980Date of Patent: March 23, 1982Assignee: Stauffer Chemical CompanyInventor: Ferenc M. Pallos
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Patent number: 4288454Abstract: The present invention relates to 1-adamantyl-3-(phenylsulfonyl)thioureas of the formula ##STR1## wherein R is lower alkyl, amino or lower alkanoylamino to methods of preparation thereof and to their use in the treatment and prevention of viral infections in mammalian and avian hosts.Type: GrantFiled: December 13, 1979Date of Patent: September 8, 1981Assignee: Hoffman-La Roche Inc.Inventors: Michael J. Kramer, Jefferson W. Tilley
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Patent number: 4276310Abstract: N-(4-Substituted-phenyl)-N'-(2-substituted-benzoyl)-thioureas of the formula ##STR1## in which R.sup.1 represents halogen,R.sup.2 represents hydrogen or halogen,R.sup.3 represents hydrogen, halogen or halogenoalkyl,R.sup.4 represents halogen, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or halogenoalkylsulphonyl, with the proviso that R.sup.3 represents halogenoalkyl if R.sup.4 represents halogen, andR.sup.5 represents hydrogen or halogen,which possess arthropodicidal, fungicidal and bactericidal properties.Type: GrantFiled: August 16, 1979Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Wilhelm Sirrenberg, Erich Klauke, Ingeborg Hammann, Ingomar Krehan, Peter Kraus, Wilhelm Stendel
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Patent number: 4233302Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof, in whichY represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl;R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.Type: GrantFiled: December 18, 1978Date of Patent: November 11, 1980Assignee: Glaxo Group LimitedInventors: Michael Martin-Smith, Barry J. Price, John Bradshaw, John W. Clitherow