Patents Examined by Richard J. Gallagher
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Patent number: 4069319Abstract: Novel thiadiazoles of the formula ##STR1## wherein R is alkyl of 1 to 3 carbon atoms, W is selected from the group consisting of oxygen and sulfur, X is selected from the group consisting of --O--, --S-- and ##STR2## R" is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, n is 1, 2, 3 or 4 and R' is selected from the group consisting of hydrogen, --CN, alkoxy of 1 to 3 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, phenyl optionally substituted with one member of the group consisting of halogen, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms or substituted with two members of the group consisting of halogen, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms, having insecticidal and nematocidal activity.Type: GrantFiled: September 8, 1976Date of Patent: January 17, 1978Assignee: Roussel UCLAFInventors: Jacques Perronnet, Laurent Taliani
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Patent number: 4069336Abstract: The present invention pertains to novel (2-oxo-pyrrolidine-1)-acetic hydrazides, methods for preparation and subsequent treatment therewith, and pharmaceutical preparations containing the same.Type: GrantFiled: February 25, 1976Date of Patent: January 17, 1978Assignee: Chemisches Laboratorium Fritz-Walter Lange GmbH & Co KGInventors: Fritz-Walter Lange, Haireddin Jacobi, Jens Muller
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Patent number: 4067720Abstract: Novel thiadiazoles of the formula ##STR1## wherein R is selected from the group consisting of alkoxy of 1 to 8 carbon atoms, cycloalkyloxy of 3 to 7 carbon atoms, alkylthio of 1 to 8 carbon atoms optionally substituted with carbalkoxy of 2 to 5 carbon atoms, alkenylthio of 2 to 4 carbon atoms, ##STR2## and benzyloxy, benzylthio, benzyl and phenyl, all aryl being optionally substituted with 1 to 2 members of the group consisting of chlorine, bromine, alkyl of 1 to 3 carbon atoms and alkoxy of 1 to 3 carbon atoms, Z and Z.sub.1 are alkyl of 1 to 4 carbon atoms and R.sub.Type: GrantFiled: April 22, 1976Date of Patent: January 10, 1978Assignee: Roussel UclafInventors: Jacques Perronnet, Laurent Taliani, Andre Teche
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Patent number: 4066766Abstract: A novel series of 1-oxo-1H-6-substitutedpyrimido[1,2-a]quinoline-2-carboxylic acids of the formula ##STR1## wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen, alkyl having from 1 to 5 carbon atoms, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio or methylsulfinyl; with the proviso that no more than two of R.sub.1, R.sub.2 and R.sub.3 are bulky groups; i.e., branched-chain alkyl or branched-chain alkoxy, and when two of said R.sub.1, R.sub.2 and R.sub.3 are bulky groups they are located on non-adjacent positions; R.sub.4 is selected from the group consisting of chloro and bromo and --OR.sub.4 ' wherein OR.sub.4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R.sub.5 is hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; R.sub.2 and R.sub.Type: GrantFiled: January 20, 1976Date of Patent: January 3, 1978Assignee: Pfizer Inc.Inventor: Saul B. Kadin
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Patent number: 4066776Abstract: Novel 1,4-disubstituted-3-nitropyrazoles having antimicrobial, parasiticidal, and herbicidal activity are prepared by a reaction sequence of which the individual steps are conventional. The new 3-nitropyrazoles are characterized by a 1-substituent and a usually carbonyl-containing 4-substituent. The novel 3(5)-nitro-4-pyrazole-carbonitrile is obtained as an intermediate in the preparation of the biologically-active compounds. Preferred compounds are 1-alkyl or -alkenyl-4-pyrazolecarboxamides and carbonitriles. The new compounds are particularly useful for the control of bacterial animal diseases.Type: GrantFiled: June 18, 1976Date of Patent: January 3, 1978Assignee: Eli Lilly and CompanyInventors: Reuben G. Jones, Norman H. Terando
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Patent number: 4066653Abstract: This invention relates to novel compounds of the isoindolenine series. More particularly, the present invention relates to certain novel 1-imono-3-(4-imino-5-thiazolidinylidene)isoindolines, 1-imino-3-(4-imino-2-thiazolin-5-ylidene)isoindolines, water-insoluble pigments prepared therefrom, and to methods for their preparation.Type: GrantFiled: June 1, 1976Date of Patent: January 3, 1978Assignee: Sterling Drug Inc.Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
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Patent number: 4066775Abstract: This invention relates to new and valuable 2-halo-5-trichloromethyl-1,3,4-thiadiazoles having a good fungicidal action, fungicides containing these compounds as active ingredients, a method of controlling fungi with these compounds, and a process for their manufacture.Type: GrantFiled: May 21, 1976Date of Patent: January 3, 1978Assignee: BASF AktiengesellschaftInventors: Ernst-Heinrich Pommer, Helmut Hagen, Helmut Fleig
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Patent number: 4066657Abstract: The present invention discloses novel 6-acylamino-2,2-dimethyl-3-phosphonopenams and certain lower alkyl esters thereof possessing antibacterial activity, methods for their production, and intermediates therefor; the production comprises the steps of reacting 6-triphenylmethylamino-2,2-dimethylpenam-3-carboxylic acid with lead tetraacetate to form the corresponding 3-acetoxy compound, the latter is converted to .alpha.-triphenylmethylamino-5,5-dimethyl-3-thiazoline-2-acetic acid which is condensed with dimethyl phosphite to produce .alpha.-triphenylmethylamino-5,5-dimethyl-4(0,0-dimethylphosphono)-thiazol idine-2-acetic acid which is cyclized to 6-triphenylmethylamino-2,2-dimethyl-3-(0,0-dimethylphosphono)penam and the latter is subsequently deblocked and acylated.Type: GrantFiled: October 29, 1976Date of Patent: January 3, 1978Assignee: Pfizer Inc.Inventor: Wayne E. Barth
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Patent number: 4064136Abstract: Process for the manufacture of a heterocyclic compound of the formula I ##STR1## in which Y denotes a --CN, --COOR' or ##STR2## group, in which R' can be an optionally substituted alkyl or aryl radical and R" and R"' independently of one another can have the same meaning as R' or can be hydrogen or, conjointly with the nitrogen atom, can form a heterocyclic 5-membered or 6-membered ring and X denotes a --S-- or --O-- atom or a --NR"-- group and the ring A can carry non-ionic substituents or optionally substituted fused rings, wherein a nitrile of the formula IInc -- ch.sub.2 -- y (ii)is reacted, in organic solvents, with a lower alcohol of the formula IIIr -- oh (iii)using a molar ratio of nitrile to alcohol of 1:0.9 to 1:1.2, in the presence of an anhydrous strong acid at temperatures of -10.degree. to +40.degree.Type: GrantFiled: July 13, 1976Date of Patent: December 20, 1977Assignee: Ciba-Geigy AGInventors: Peter Loew, Hansrudolf Schwander, Haukur Kristinsson
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Patent number: 4064258Abstract: 1-Alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene-N-alkyloxazolid ine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dines and derivatives are also intermediates for the 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s. The 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s can be prepared by base or acid hydrolysis of the corresponding 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative; or by treatment of the corresponding 3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.Type: GrantFiled: July 19, 1976Date of Patent: December 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Brian Lewis, Stefan H. Unger, Karl G. Untch
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Patent number: 4064259Abstract: 1-Alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.Type: GrantFiled: July 19, 1976Date of Patent: December 20, 1977Assignee: Syntex (U.S.A.) Inc.Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger
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Patent number: 4062860Abstract: 3,4-DICYANO-1,2,5-THIADIAZOLE IS PREPARED BY REACTING DIAMINOMALEONITRILE (DAMN) with thionyl chloride (SOCl.sub.2) at a temperature of 40.degree. C. up to the boiling point of thionyl chloride wherein the molar ratio of SOCl.sub.2 /DAMN is between 2:1 and 10:1.Type: GrantFiled: October 19, 1976Date of Patent: December 13, 1977Assignee: Montedison S.p.A.Inventors: Giuseppe Ribaldone, Renato Grecu
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Patent number: 4062670Abstract: Compounds of the formula ##STR1## wherein X is O or NR.sup.3 in which R.sup.3 is hydrogen or alkyl; X.sup.1 is oxygen or sulfur; Y is hydrogen, halogen, cyano, alkyl, alkoxy, haloalkoxy, alkylthio or haloalkyl; Z is hydrogen, halogen, alkyl, alkoxy or haloalkyl; and R.sup.1 and R.sup.2 each independently may be hydrogen, alkyl, aryl or aralkyl and R is hydrogen or methyl are useful as herbicides.Type: GrantFiled: November 4, 1976Date of Patent: December 13, 1977Assignee: Shell Oil CompanyInventor: Kurt H. G. Pilgram
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Patent number: 4061646Abstract: Crude 2-mercaptobenzothiazole is purified by preparing a crude, liquid 2-mercaptobenzothiazole by reacting aniline, carbon disulfide and sulfur under elevated pressure at high temperatures; extracting said crude, liquid 2-mercaptobenzothiazole in the molten state with cold carbon disulfide by liquid-liquid extraction thereby forming a slurry of 2-mercaptobenzothiazole crystals; and filtering and drying said crystals.Type: GrantFiled: June 30, 1976Date of Patent: December 6, 1977Assignee: Sanshin Kagaku Kogyo Company, LimitedInventors: Yutaka Kawaoka, Tatsuo Kifune, Masahiko Teshima, Tatsuya Koizumi
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Patent number: 4061647Abstract: The invention relates to thiazolidine derivatives having in 4-position a hydroxy group and a 3'-sulphamyl-phenyl substituent the phenyl ring of which is di-substituted by halogen or methyl, in 2 position an imino group and in 1-position an aliphatic or cycloaliphatic substituent. Said thiazolidines have diuretic activity.The invention also relates to a process for the manufacture of said compounds.Type: GrantFiled: July 27, 1976Date of Patent: December 6, 1977Assignee: Hoechst AktiengesellschaftInventors: Hans-Jochen Lang, Roman Muschaweck
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Patent number: 4061648Abstract: This invention discloses new compounds of the formula ##STR1## WHEREIN R.sup.1 is selected from the group consisting of alkyl, cycloalkyl, alkenyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl and alkylsulfinyl; R.sup.2 is selected from the group consisting of alkyl, alkenyl, haloalkyl and ##STR2## wherein R.sup.4 and R.sup.5 are each selected from the group consisting of hydrogen and alkyl; p is an integer from 0 to 3; Y is oxygen or sulfur; R.sup.3 is selected from the group consisting of alkyl and halogen; and q is an integer from 0 to 2. Further disclosed is the herbicidal utility of the foregoing compounds.Type: GrantFiled: March 22, 1976Date of Patent: December 6, 1977Assignee: Velsicol Chemical CorporationInventor: John Krenzer
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Patent number: 4061632Abstract: New 3,11-dihydro-6H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[4,3-d]pyrimidin-6 -one derivatives have the general formula ##STR1## The compounds are useful as anti-inflammatory agents.Type: GrantFiled: September 17, 1976Date of Patent: December 6, 1977Assignee: E. R. Squibb & Sons, Inc.Inventors: Theodor Denzel, Hans Hoehn
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Patent number: 4059590Abstract: 4-HALO-5-ARYL-1,2,3-DITHIAZOLE, USEFUL AS FUNGICIDES, OVICIDES, INSECTICIDES AND HERBICIDES, ARE PREPARED BY REACTING A N-aryl cyanothioformamide and a sulfur dihalide in the presence of a catalytic amount of a formamide compound or quaternary ammonium salt.Type: GrantFiled: June 21, 1976Date of Patent: November 22, 1977Assignee: Chevron Research CompanyInventor: Joseph E. Moore
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Patent number: 4059433Abstract: A new class of herbicidal compounds consisting of 1-alkyl- and 1,1-dialkyl-3-(4-substituted-3-alkoxy-5-isothiazolyl)ureas and N-(4-substituted-3-alkoxy-5-isothiazolyl)alkanamides, in which the 4-substituent consists of alkoxycarbonyl, cyano and carbamoyl, exhibits preemergence and postemergence herbicidal activity, controlling effectively the growth of a wide spectrum of grassy and broad-leaved plant species. The synthesis of members of this class is described in detail, and the utility of representative compounds is exemplified.Type: GrantFiled: June 18, 1976Date of Patent: November 22, 1977Assignee: FMC CorporationInventor: Loren Kenneth Gibbons
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Patent number: 4056620Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.Type: GrantFiled: May 24, 1976Date of Patent: November 1, 1977Assignee: Smith Kline & French Laboratories LimitedInventor: George Raymond White