Patents Examined by Richard J. Gallagher
  • Patent number: 4069319
    Abstract: 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: Grant
    Filed: September 8, 1976
    Date of Patent: January 17, 1978
    Assignee: Roussel UCLAF
    Inventors: Jacques Perronnet, Laurent Taliani
  • Patent number: 4069336
    Abstract: 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: Grant
    Filed: February 25, 1976
    Date of Patent: January 17, 1978
    Assignee: Chemisches Laboratorium Fritz-Walter Lange GmbH & Co KG
    Inventors: Fritz-Walter Lange, Haireddin Jacobi, Jens Muller
  • Patent number: 4067720
    Abstract: 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: Grant
    Filed: April 22, 1976
    Date of Patent: January 10, 1978
    Assignee: Roussel Uclaf
    Inventors: Jacques Perronnet, Laurent Taliani, Andre Teche
  • Patent number: 4066766
    Abstract: 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: Grant
    Filed: January 20, 1976
    Date of Patent: January 3, 1978
    Assignee: Pfizer Inc.
    Inventor: Saul B. Kadin
  • Patent number: 4066776
    Abstract: 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: Grant
    Filed: June 18, 1976
    Date of Patent: January 3, 1978
    Assignee: Eli Lilly and Company
    Inventors: Reuben G. Jones, Norman H. Terando
  • Patent number: 4066653
    Abstract: 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: Grant
    Filed: June 1, 1976
    Date of Patent: January 3, 1978
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Nicholas A. Ambrosiano
  • Patent number: 4066775
    Abstract: 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: Grant
    Filed: May 21, 1976
    Date of Patent: January 3, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst-Heinrich Pommer, Helmut Hagen, Helmut Fleig
  • Patent number: 4066657
    Abstract: 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: Grant
    Filed: October 29, 1976
    Date of Patent: January 3, 1978
    Assignee: Pfizer Inc.
    Inventor: Wayne E. Barth
  • Patent number: 4064136
    Abstract: 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: Grant
    Filed: July 13, 1976
    Date of Patent: December 20, 1977
    Assignee: Ciba-Geigy AG
    Inventors: Peter Loew, Hansrudolf Schwander, Haukur Kristinsson
  • Patent number: 4064258
    Abstract: 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: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Brian Lewis, Stefan H. Unger, Karl G. Untch
  • Patent number: 4064259
    Abstract: 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: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger
  • Patent number: 4062860
    Abstract: 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: Grant
    Filed: October 19, 1976
    Date of Patent: December 13, 1977
    Assignee: Montedison S.p.A.
    Inventors: Giuseppe Ribaldone, Renato Grecu
  • Patent number: 4062670
    Abstract: 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: Grant
    Filed: November 4, 1976
    Date of Patent: December 13, 1977
    Assignee: Shell Oil Company
    Inventor: Kurt H. G. Pilgram
  • Patent number: 4061646
    Abstract: 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: Grant
    Filed: June 30, 1976
    Date of Patent: December 6, 1977
    Assignee: Sanshin Kagaku Kogyo Company, Limited
    Inventors: Yutaka Kawaoka, Tatsuo Kifune, Masahiko Teshima, Tatsuya Koizumi
  • Patent number: 4061647
    Abstract: 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: Grant
    Filed: July 27, 1976
    Date of Patent: December 6, 1977
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jochen Lang, Roman Muschaweck
  • Patent number: 4061648
    Abstract: 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: Grant
    Filed: March 22, 1976
    Date of Patent: December 6, 1977
    Assignee: Velsicol Chemical Corporation
    Inventor: John Krenzer
  • Patent number: 4061632
    Abstract: 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: Grant
    Filed: September 17, 1976
    Date of Patent: December 6, 1977
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Theodor Denzel, Hans Hoehn
  • Patent number: 4059590
    Abstract: 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: Grant
    Filed: June 21, 1976
    Date of Patent: November 22, 1977
    Assignee: Chevron Research Company
    Inventor: Joseph E. Moore
  • Patent number: 4059433
    Abstract: 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: Grant
    Filed: June 18, 1976
    Date of Patent: November 22, 1977
    Assignee: FMC Corporation
    Inventor: Loren Kenneth Gibbons
  • Patent number: 4056620
    Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.
    Type: Grant
    Filed: May 24, 1976
    Date of Patent: November 1, 1977
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George Raymond White