Thiocarboxamides (i.e., Compounds Containing -c(=s)-hnh, Wherein Substitution May Be Made For Hydrogen Only) Patents (Class 564/74)
  • Patent number: 5101071
    Abstract: Pesticidal compositions for use against insects and acarines comprising a compound of Formula (I):R.sup.1 --(CA.dbd.CA').sub.n C(.dbd.S)NR.sup.2 R.sup.3 (I)whereinR.sup.1 is: C.sub.1-14 alkyl optionally substituted by C.sub.1-6 alkoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy, aryl, aryloxy or aryl (C.sub.1-6) alkoxy; aryloxy or aryl (C.sub.1-6) alkoxy; any of which groups may be substituted by halo,n is 1 or 2,each A and A' is independently hydrogen, halo, C.sub.1-4 alkyl or halo (C.sub.1-4) alkyland R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl, either of which may be substituted by one or more of halo, C.sub.2-6 alkenyl, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, C.sub.2-6 alkynyl or cyano, except that, when n is 1 and R.sup.2 is alkyl and R.sup.3 is hydrogen and A and A' are both hydrogen then R.sup.1 is not substituted alkyl.
    Type: Grant
    Filed: July 22, 1991
    Date of Patent: March 31, 1992
    Assignee: Burroughs Wellcome Co.
    Inventors: Robert J. Blade, Robert J. Peek
  • Patent number: 5091420
    Abstract: Pesticidal compositions for use against insects and acarines comprising a compound of Formula (I):R.sup.1 --(CA.dbd.CA').sub.n C(.dbd.S)NR.sup.2 R.sup.3 (I)wherein R.sup.1 is: C.sub.1-14 alkyl optionally substituted by C.sub.1-6 alkoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.2-6 alkenyloxy, C.sub.2-6 alkynyloxy, aryl, aryloxy or aryl (C.sub.1-6) alkoxy; aryloxy or aryl (C.sub.1-6) alkoxy; any of which groups may be substituted by halo,n is 1 or 2,each A and A' is independently hydrogen, halo, C.sub.1-4 alkyl or halo (C.sub.1-4) alkyl and R.sup.2 and R.sup.3 are independently hydrogen, C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl, either of which may be substituted by one or more of halo, C.sub.2-6 alkenyl, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkenyl, C.sub.1-6 alkoxy, C.sub.2-6 alkynyl or cyano, except that, when n is 1 and R.sup.2 is alkyl and R.sup.3 is hydrogen and A and A' are both hydrogen then R.sup.1 is not substituted alkyl.Most of the compounds of Formula (I) are novel.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: February 25, 1992
    Assignee: Burroughs Wellcome Co.
    Inventors: Robert J. Blade, Robert J. Peek
  • Patent number: 5043466
    Abstract: The preparation of compounds having the formula I ##STR1## where R.sup.1 is --CN, --CO--N(CH.sub.3).sub.2 or --CS--N(CH.sub.3).sub.2 and R.sup.2 is hydrogen, methyl or a removable protecting group is carried out by condensing a compound having the formula ##STR2## where M is lithium, sodium, potassium or halomagnesium and R.sup.3 is methyl or a removable protecting group in a solvent comprising 80-100% of one or more hydrocarbons and 0-20% of one or more ethers.The solvent enables less inconvenient reaction temperatures to be used and higher yields to be obtained. Compounds (I) are new per se where R.sup.1 is --CS--N(CH.sub.3).sub.2. Compounds (I) are chemical intermediates for preparing N,N-dimethyl-2-(1-hydroxycyclohexyl)-2-(4-hydroxyphenyl or 4-methoxyphenyl) ethylamine and pharmaceutically acceptable salts thereof. These end products are antidepressants.
    Type: Grant
    Filed: January 26, 1990
    Date of Patent: August 27, 1991
    Assignee: John Wyeth & Bro., Limited
    Inventor: Robin G. Shepard
  • Patent number: 5041663
    Abstract: The invention relates to novel oxime ethers of the formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, lower alkylthio, lower haloalkylthio, lower alkylsulfinyl, lower alkylsulfonyl, lower haloalkylsulfinyl, lower haloalkylsulfonyl or nitro, each of R.sub.2 and R.sub.3 is hydrogen, halogen, lower alkyl, lower alkoxy or lower haloalkoxy, and Q is an unsubstituted or substituted lower alkyl, lower alkenyl, lower alkynyl or cycloalkyl group, a lower alkanoyl radical, an aliphatic, cycloaliphatic, aromatic or heterocyclic acyl radical which may be substituted or unsubstituted, a carbonyl or thiocarbonyl radical, an aryl or aralkyl radical, an acylimidomethyl radical, a phthalimidomethyl radical or a heterocyclic radical.These compounds are able to act as antidotes or safeners for protecting cultivated plants from the phytotoxic action of aggressive herbicides.
    Type: Grant
    Filed: December 11, 1990
    Date of Patent: August 20, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Henry Martin, Urs Fricker
  • Patent number: 5041653
    Abstract: A method for sensitizing hypoxic tumor cells to radiation using derivatives of benzamide are disclosed. Some of the compounds useful in the method of the invention are novel.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: August 20, 1991
    Assignee: SRI International
    Inventors: William W. Lee, Edward W. Grange, J. Martin Brown
  • Patent number: 5021414
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --,wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: June 4, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
  • Patent number: 5013759
    Abstract: Substituted phenylacetic acid amide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R.sub.1 is H, OH or CH.sub.3 ; R.sub.2 is straight chain alkenyl, branched chain or cyclic hydrocarbon having from about 7 to about 24 carbon atoms; R.sub.3 is OH, OSO.sub.3.sup.-, OPO.sub.3.sup.-- or a short chain ester with from about 1 to about 6 carbon atoms.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: May 7, 1991
    Assignee: The Procter & Gamble Company
    Inventors: Elizabeth F. Berman, Brian L. Buckwalter, Thomas L. Cupps, Joseph H. Gardner
  • Patent number: 4997980
    Abstract: Disclosed are novel compounds of the formula: ##STR1## wherein: X=--NR.sub.5 R.sub.6, or --OR.sub.7 ;R.sub.1 and R.sub.2 are independently hydrogen, substituted or unsubstituted alkyl, haloalkyl, hydroxyalkyl alkoxyalkyl, alkylaminoalkyl or arylalkyl having up to 18 carbons, cycloalkyl; phenyl or naphthyl; alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituents;R.sub.3 is hydrogen, benzyl, alkoxybenzyl, halobenzyl or alkylbenzyl, provided that if neither R.sub.1 nor R.sub.2 is hydrogen, then R.sub.3 is hydrogen;R.sub.4 is a divalent aromatic group which is substituted or unsubstituted;R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen, alkyl, hydroxyalkyl, haloalkyl, alkoxyalkyl, alkylaminoalkyl, acylaminoalkyl, aminoalkyl or phenylalkyl having up to 12 carbons; a cycloalkyl substitutent; phenyl or naphthyl; an alkylphenyl, cyanophenyl, halophenyl or alkoxyphenyl substituent;Furthermore, either R.sub.1 and R.sub.3 or R.sub.1 and R.sub.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: March 5, 1991
    Assignee: Anitec Image Corporation
    Inventors: Bruce M. Resnick, Allan J. Wexler
  • Patent number: 4983630
    Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
  • Patent number: 4968677
    Abstract: 1-Aryl-2-naphthoylamines of formula I are described ##STR1## wherein R.sub.1 is halogen, nitro, cyano, C.sub.1 -C.sub.6 alkyl that is unsubstituted or mono- or poly-substituted by halogen and/or C.sub.1 -C.sub.3 alkoxy, or is C.sub.3 -C.sub.6 cycloalkyl, OR.sub.4, NR.sub.5 R.sub.6, CO2R.sub.5, CONR.sub.5 R.sub.6 or NHCOR.sub.7, or wherein two adjacent positions in the nucleus are bridged by a methylenedioxy or ethylenedioxy group that is unsubstituted or mono- or poly-substituted by fluorine, wherein further R.sub.4 is hydrogen or C.sub.1 -C.sub.6 alkyl that is unsubstituted or substituted by C.sub.1 -C.sub.3 alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.4 alkenyl, 2-propynyl, 3-halo-2-propynyl, ##STR2## or COR.sub.7, each of R.sub.5 and R.sub.6, independently of the other, is H or C.sub.1 -C.sub.4 alkyl, R.sub.7 is C.sub.1 -C.sub.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: November 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Riebli
  • Patent number: 4962224
    Abstract: Disclosed herein are N-naphthoylglycines and methods of their preparation. The N-naphthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: August 22, 1989
    Date of Patent: October 9, 1990
    Assignee: American Home Products Corporation
    Inventors: Jay E. Wrobel, Kazimir Sestanj
  • Patent number: 4950789
    Abstract: Aromatic polyalkyleneoxy polyamines which are the reaction products of an aminocarbonyl, a polyalkyleneoxy polyamine, and aromatic diamines are useful in reaction injection molding processes to enhance the physical properties of the products produced. In addition, the polyamines of this invention are also useful as compatiblilizing agents in RIM systems to compatibilize mixtures of high molecular weight and low molecular weight polyols.
    Type: Grant
    Filed: January 25, 1989
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Benny G. Barron
  • Patent number: 4935513
    Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of a Group IIA metal fluoride as an adjuvant.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4935514
    Abstract: An amide is thiated to the corresponding thioamide by reacting it with phosphorus pentasulfide in the presence of an adjuvant selected from diatomaceous earth, zeolites, and molecular sieves.
    Type: Grant
    Filed: June 6, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4935510
    Abstract: Ammonium hydroxide is used in the recovery of a thiono compound prepared by reacting an organic carbonyl compound with phosphorus pentasulfide to improve the product yield.
    Type: Grant
    Filed: June 7, 1989
    Date of Patent: June 19, 1990
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4904661
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined bis-phenolic nucleus including a hydroxyphenyl-hydroxynaphthyl; hydroxyphenyl-hydroxyindanyl, hydroxyphenyl-hydroxybenzothienyl or di-hydroxyphenyl-ethylene or vinylene nucleus;wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages,wherein R.sup.1 is hydrogen, or alkyl, alkenyl, cycloalkyl, halogenoalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 -- or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --S--, --SO-- or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene;wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro;or a salt thereof when appropriate.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: February 27, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: William R. Pilgrim, Derek W. Young, Brian S. Tait, Graham C. Crawley, Philip N. Edwards, George B. Hill
  • Patent number: 4885027
    Abstract: Arylmethylenesulfonamidoacetamide and thioacetamide derivatives and arylmethylenesulfonamidoester intermediates therefor. The compounds are useful as selective herbicides especially with respect to the prevention and elimination of barnyardgrass in grass crops, especially in rice crops.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: December 5, 1989
    Assignee: Chevron Research Company
    Inventor: Patricia B. Pomidor
  • Patent number: 4863966
    Abstract: Compounds of formula (I) are pesticides having activity against arthropods: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H, alkyl, alkoxy, halo, cyano or trifluoromethyl, or two of R.sup.1, R.sup.2 and R.sup.3 are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl; andR.sup.4 and R.sup.5 are H, alkenyl or haloalkenyl or optionally substituted alkyl, aryl or aralkyl, or NR.sup.4 R.sup.5 represents a heterocyclic ring; or an acid addition salt thereof.The invention further provides methods for the preparation of the compounds, pesticidal formulations containing them, and their use in controlling arthropod pests.
    Type: Grant
    Filed: February 17, 1981
    Date of Patent: September 5, 1989
    Assignee: Burroughs Wellcome Co.
    Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
  • Patent number: 4853484
    Abstract: Disclosed herein are N-[[6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]thioxomethyl]-N-methylgly cine S-oxide (tolrestat S-oxide) and the amide thereof and methods of their preparation. The S-oxides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: October 28, 1987
    Date of Patent: August 1, 1989
    Assignee: American Home Products Corporation
    Inventors: Eckhardt S. Ferdinandi, Michael S. Malamas, Kazimir Sestanj, Surendra N. Sehgal
  • Patent number: 4808628
    Abstract: An amide derivative of the formula (I): ##STR1## or a tautomeric form thereof, wherein R is a phenyl group substituted in the 4-position by a group of R.sup.1 XCH.sub.2--, where R.sup.1 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 alkylcarbonyl, or H, and X is oxygen or sulphur; E is CN, or CSNH.sub.2, or CONH.sub.2 ; and Y is C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, 1-pyrazolyl or 2-furyl. Compositions and processes for using these derivatives to combat plant fungi are also disclosed.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: February 28, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Margaret C. Shephard, Patrick J. Crowley
  • Patent number: 4795487
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: the substituent X is chosen from cyano, carbamoyl and thiocarbamoyl;Z is selected from hydrogen, methyl, C.sub.1 to C.sub.4 alkanoyl, sulfamoyl, dimethylsulfamoyl and trifluoroacetylamino;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl and alkynyl;R.sup.3 is selected from alkyl; andR.sup.4 is selected from hydrogen, alkyl, and alkoxycarbonyl.The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments and the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.
    Type: Grant
    Filed: July 16, 1986
    Date of Patent: January 3, 1989
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Craig G. Lovel
  • Patent number: 4753934
    Abstract: Compounds of the formula ##STR1## wherein A, B, R.sub.1, X and Q are substituents of various types, and acid addition salts thereof. The compounds are useful as fungicides.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: June 28, 1988
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Josef Nickl, Helmut Pieper, Jurgen Curtze, Christo Drandarevski, Sigmund Lust
  • Patent number: 4752615
    Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.
    Type: Grant
    Filed: November 13, 1986
    Date of Patent: June 21, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
  • Patent number: 4752321
    Abstract: A compound of the general formula (I): ##STR1## wherein R is C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, both optionally substituted by lower alkyl, halogen or trialkylsilyl; E is CN or CSHN.sub.2 ; and Y is C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, 1-pyrazolyl or 2-furyl. The compounds have fungicidal and plant growth regulating activity.
    Type: Grant
    Filed: November 18, 1986
    Date of Patent: June 21, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Stephen P. Heaney, Patrick J. Crowley, Laurence G. Reynolds
  • Patent number: 4741897
    Abstract: The present invention relates to new compounds of the general formula: ##STR1## where X is iodine or hydrogen; A is a linking portion; and R is an iodinatable aryl or heteroaryl group having electron donating substituents. These compounds are useful precursors to the iodinated thyroid hormones for radioimmunoassay determination of thyroid hormones in biological fluids.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: May 3, 1988
    Assignee: Baxter Travenol
    Inventors: Judith Andrews, Christine Burns, James Quick
  • Patent number: 4736056
    Abstract: This invention relates to a process for preparing a malonic acid derivative compound of formula (i) depicted herein in high yield and high purity by reacting a malonic acid derivative compound of formula (ii) depicted herein with an alkylating agent of formula (iii) depicted herein in the presence of a solvent and a base.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: April 5, 1988
    Inventors: Oliver W. Smith, Russell J. Outcalt
  • Patent number: 4690708
    Abstract: A herbicide of the formula: ##STR1## in which: Z is N or CX',W, Y, Y', X, Z' and X' represent H, a halogen atom, NO.sub.2, CN or a polyhalogenoalkyl, alkyl or alkoxy group,R.sup.2 represents H, halogen, substituted alkyl, allyl, propargyl, CN, NR.sup.4 R.sup.5, C(X.sup.2)R.sup.7, C(X.sup.2)X.sup.3 R.sup.8, C(X.sup.2)NR.sup.4 R.sup.5, SO.sub.2 F, SO.sub.2 OR.sup.8, SO.sub.2 NR.sup.4 R.sup.5 or P(X.sup.2)R.sup.9 R.sup.10,R.sup.1 is halogen, X.sup.2 R.sup.3 or NR.sup.4 R.sup.5,R.sup.3 is optionally substituted alkyl or is allyl or propargyl,R.sup.4, R.sup.7 and R.sup.8 represent H, alkyl, cycloalkyl, phenyl, allyl, propargyl or the like,R.sup.5 represents R.sup.4, a cation or OR.sup.6, R.sup.6 being H, a cation or alkyl,X.sup.2 and X.sup.3 are O or S,R.sup.9 and R.sup.10 are H, alkyl, OH, OM or R.sup.1, andM is a cation.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: September 1, 1987
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Alain Chene, Guy Borrod
  • Patent number: 4686232
    Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly strains thereof which are resistant to benzimidazole or thiophanate fungicides and/or cyclic imide fungicides.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: August 11, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Mitsuru Sasaki, Hiroshi Noguchi, Toshiro Kato
  • Patent number: 4672059
    Abstract: Disclosed herein are tolrestat and oxotolrestat amides and methods of preparation. The amides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: November 18, 1985
    Date of Patent: June 9, 1987
    Assignee: American Home Products Corporation
    Inventors: Kazimir Sestanj, Eckhardt S. Ferdinandi
  • Patent number: 4672058
    Abstract: Disclosed herein are tolrestat amides and methods of preparation. The amides are new aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: June 9, 1987
    Assignee: American Home Products Corporation
    Inventors: Francesco Bellini, Kazimir Sestanj, Michael Kraml
  • Patent number: 4652303
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: W are selected from the group consisting of:the groups R.sup.5 --CO-- and R.sup.5 --CS-- wherein: R.sup.5 is selected from alkenyl, alkynyl, benzyl, phenyl, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted benzyl, substituted phenyl and the acetal, hemiacetal, oxime, imine and Schiff base derivatives of the group R.sup.5 --CO--;the groups Y--CO-- and Y--CS-- wherein Y is selected from hydroxy, mercapto, alkylthio and the groups MO-- and MS-- wherein M is an organic or an inorganic cation;the groups R.sup.6 R.sup.7 NCO-- and R.sup.6 R.sup.7 NCS-- wherein R.sup.6 and R.sup.7 are independently selected from hydrogen, alkyl, substituted alkyl, alkanoyl, carboxy, alkoxycarbonyl, alkylsulfonyl, benzoyl, benzenesulfonyl, substituted benzoyl, substituted benzenesulfonyl, or R.sup.6 and R.sup.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: March 24, 1987
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4643763
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;x are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino; the group --NHC(.dbd.B(NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: February 17, 1987
    Assignee: ICI Australia Limited
    Inventors: Graeme J. Farquharson, Keith G. Watson, Graham J. Bird
  • Patent number: 4633014
    Abstract: Substituted 3-hydrazinopropionates comprising compounds of the general fola: ##STR1## wherein R.sup.1, R.sup.2 =H, an alkyl, a substituted alkyl, hydroxycarbonyl, alkoxycarbonyl, an aryl, an aralkyl, an unsaturated alkyl, a substituted aryl or a substituted aralkyl: ##STR2## wherein R.sup.7, R.sup.8 =H, an alkyl, an unsaturated alkyl, an aralkyl, an aryl, a substituted alkyl,R.sup.9 =OH, an alkoxy, an aralkoxy, an alkyl, an unsaturated alkyl, an aryl, a substituted aryl, an aralkyl;R.sup.4 is --C.tbd.N, --COR.sup.10, wherein R.sup.10 =OR.sup.11, NR.sup.12 R.sup.13, where R.sup.11 is H, an alkyl, an aralkyl and an alkali metal, R.sup.11 and R.sup.12 are each H, an alkyl, an aralkyl, an aryl;R.sup.5, R.sup.6 = an alkyl, an aryl, an aralkyl.
    Type: Grant
    Filed: July 6, 1984
    Date of Patent: December 30, 1986
    Assignee: Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr
    Inventors: Gunar A. Bremanis, Ivars Y. Kalvinsh, Irene B. Antsena, Edmund Y. Lukevits, Maris M. Veveris, Valeryans Y. Kauss, Peter T. Trapentsier, Edvards E. Liepinsh
  • Patent number: 4629498
    Abstract: Phenoxyphenoxyalkanoylthioamides of the formula I ##STR1## wherein X.sub.1 is chlorine or trifluoromethyl, X.sub.2 is chlorine or nitro, R.sub.1 is C.sub.1 -C.sub.4 alkyl, and R.sub.2 is the amino group or an amidino group ##STR2## wherein each of R.sub.3 and R.sub.4 independently is hydrogen or C.sub.1 --C.sub.4 alkyl or taken together they form a C.sub.4 --C.sub.5 alkylene chain, have herbicidal and growth regulating properties. They are suitable for selectively controlling weeds in crops of useful plants, especially in cereals and rice.
    Type: Grant
    Filed: May 2, 1985
    Date of Patent: December 16, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Otto Rohr, Georg Pissiotas
  • Patent number: 4628061
    Abstract: Novel compounds have a formula (I) ##STR1## wherein ##STR2## represents a bicyclo [2,2,1] hept-2Z-ene, bicyclo [2,2,1] heptane, 7-oxa-bicyclo [2,2,1] hept-2Z-ene, 7-oxa-bicyclo [2,2,1] heptane, bicyclo [2,2,2] oct-2Z-ene or bicyclo [2,2,2] octane substituted at the 5-position by the group R.sup.1 and at the 6-position by the group ANR.sup.2 R, a 6,6-dimethyl-bicyclo [3,1,1] heptane substituted at the 2-position by the group R.sup.1 and at the 3-position by the group ANR.sup.2 R or at the 2-position by the group ANR.sup.2 R and at the 3-position by the group R.sup.1, a cyclohex-1-ene or cyclohexane substituted at the 4-position by the group R.sup.1 and at the 5-position by the group ANR.sup.2 R or a 1-hydroxycyclopentane substituted at the 2-position by the group R.sup.1 and at the 2-position by the group ANR.sup.2 R, R.sup.
    Type: Grant
    Filed: August 23, 1983
    Date of Patent: December 9, 1986
    Assignee: National Research Development Corporation
    Inventors: Robert L. Jones, Norman H. Wilson
  • Patent number: 4625048
    Abstract: Carbamic acid esters of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, X, and Y are as defined hereinafter, process for their preparation, as well as pesticidal compositions containing these compounds as the active ingredient and methods for using the pesticidal compositions for the control of pests are described.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: November 25, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Rene Zurfluh
  • Patent number: 4604128
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: m is an integer selected from 1 to 4;n is zero or an integer selected from 1 to 4;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, alkylthio, sulfamoyl, substituted sulfamoyl, amino, substituted amino, the group --(CH.sub.2).sub.p C(.dbd.A)Z in which p is zero or one A is oxygen or sulfur, and Z is hydrogen, hydroxy, alkoxy, alkylthio, alkyl, substituted alkyl, amino or substituted amino, the group --NHC(.dbd.B)NR.sup.7 R.sup.8 in which B is oxygen or sulfur and R.sup.7 and R.sup.8 are hydrogen or alkyl;R.sup.1 is selected from hydrogen, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.4 is selected from hydrogen, halogen, alkyl, cyano and alkoxycarbonyl.
    Type: Grant
    Filed: September 10, 1985
    Date of Patent: August 5, 1986
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, John D. Wishart, Graeme J. Farquharson, Graham J. Bird, Lindsay E. Cross
  • Patent number: 4581375
    Abstract: The present invention relates to new substituted hydroxy-malonic acid amide-thioamides of the formula (I) ##STR1## in which R represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl,and a process for their preparation and their use as agents for combating pests, in particular insecticides and acaricides.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: April 8, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Fauss, Kurt Findeisen, Benedikt Becker, Ingeborg Hammann, Bernhard Homeyer
  • Patent number: 4579581
    Abstract: Herbicidal and fungicidal benzamide derivatives of the formula (I) ##STR1## wherein R.sup.1 is an optionally substituted alkyl, alkenyl, aryl, heterocyclyl, benzyl, or heterocyclylmethyl radical;R.sup.2 is hydrogen, or an optionally substituted alkyl, alkenyl, benzyl, or heterocyclylmethyl, radical;X is oxygen, sulphur, or an --NH-- group;R.sup.3 is an optionally substituted alkyl or alkenyl radical when X is oxygen or sulphur, or is an optionally substituted alkanoyl radical when X is --NH--;and E is a --CN, --CONH.sub.2, --CSNH.sub.2, or --CONR.sup.4 R.sup.5 group wherein each R.sup.4 and R.sup.5 is an optionally substituted alkyl or alkenyl group.
    Type: Grant
    Filed: February 22, 1984
    Date of Patent: April 1, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: Ian T. Kay, David Bartholomew, Emyr G. Williams, Robert A. Noon
  • Patent number: 4551169
    Abstract: Carbamate derivatives having the formula: ##STR1## wherein X represents an oxygen atom or a sulfur atom and Y represents a --CH-- group or a nitrogen atom; and herbicides utilizing the same.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: November 5, 1985
    Assignee: Toyo Soda Manufacturing Company, Limited
    Inventors: Tetsuo Takematsu, Makoto Konnai, Hideo Morinaka, Yunji Nonaka, Akira Nakanishi
  • Patent number: 4532139
    Abstract: Alkynamide compounds, and pharmaceutically-acceptable salts thereof, of the formula: ##STR1## wherein X is O or S; R is straight or branched alkyne having from 11 to 23 carbon atoms; R.sub.1 is H, OH, or OCH.sub.3 ; R.sub.2 is OH or a short-chain ester; and wherein at least one of R.sub.1 and R.sub.2 is OH or OCH.sub.3. Compositions, useful for producing analgesia in humans or lower animals, comprise a safe and effective amount of: an alkynamide, pharmaceutically-acceptable salts thereof, or mixtures thereof; and a pharmaceutically-acceptable carrier. Preferably, these alkynamides are N-vanillyl-alkynamides. Methods of treatment, comprising administering a safe and effective amount of these alkynamides, pharmaceutically-acceptable salts thereof, or mixtures thereof, include methods of parenteral, oral, and topical administration.
    Type: Grant
    Filed: July 14, 1983
    Date of Patent: July 30, 1985
    Assignee: The Procter & Gamble Company
    Inventors: John M. Janusz, Thomas R. LaHann
  • Patent number: 4531968
    Abstract: Halothiopyruvic amides, which have viricidal and/or fungicidal activity of the formula: ##STR1## wherein X is chloro, fluoro, bromo or iodo; andR is cyclohexyl substituted with 0, 1 or 2 lower alkyl groups, or phenyl substituted with 0, 1 or 2 lower alkyl groups.
    Type: Grant
    Filed: March 30, 1984
    Date of Patent: July 30, 1985
    Assignee: Chevron Research Company
    Inventors: William L. Schinski, Raymond J. Lukens
  • Patent number: 4512997
    Abstract: Novel 4H-1,2,4-triazoles of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be in different positions of the benzene rings and are individually selected from the group consisting of hydrogen, --OH, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, --CF.sub.3, --NO.sub.2, --NH.sub.2 and --NH--AlK and ##STR2## and AlK, AlK.sub.1 and AlK.sub.2 are alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 together and/or R.sub.3 and R.sub.4 together are methylenedioxy, R is selected from the group consisting hydrogen, alkyl of 1 to 4 carbon atoms, --CH.sub.2 --COOH and --CH.sub.2 --COOAlK.sub.3 and AlK.sub.3 is alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable analgesic activity and a novel method for their preparation.
    Type: Grant
    Filed: November 17, 1983
    Date of Patent: April 23, 1985
    Assignee: Roussel Uclaf
    Inventors: Jean Meier, Francois Clemence
  • Patent number: 4460603
    Abstract: N-[1-(2'-substituted-alkyl)-amidomethyl and carboalkoxymethyl]-substituted-N-acylanilines have fungicidal activity.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 17, 1984
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • Patent number: 4459347
    Abstract: The use of oxythioamido substituted arylhydrazides in producing images in silver halide photographic elements is disclosed. The oxythioamido substituted arylhydrazide can be incorporated in photographic silver halide emulsions. The oxythioamido substituent is capable of promoting adsorption of the arylhydrazide to silver halide grain surfaces. In negative working surface latent image forming emulsions the oxythioamido substituted arylhydrazides permit higher speeds to be achieved. In direct positive internal latent image forming emulsions increased nucleation activity can be achieved.
    Type: Grant
    Filed: May 11, 1983
    Date of Patent: July 10, 1984
    Assignee: Eastman Kodak Company
    Inventors: Richard L. Parton, James A. Friday
  • Patent number: 4414221
    Abstract: The compounds of the formula: ##STR1## wherein R.sup.1 represents phenyl substituted in at least the 2-position by fluorine, chlorine, bromine or iodine, R.sup.2 represents a group R.sup.3, --OR.sup.3, --SR.sup.3 or --NR.sup.3 R.sup.4 where R.sup.3 represents hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 6 carbon atoms, cycloalkenyl of 3 to 7 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 10 carbon atoms or naphthyl, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy or alkylthio groups of 1 to 6 carbon atoms, nitro groups, cyano groups or mercapto groups, R.sup.4 represents a group as defined for R.sup.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: November 8, 1983
    Assignee: FBC Limited
    Inventors: John H. Parsons, Peter J. West
  • Patent number: 4377532
    Abstract: The invention relates to 3-phenoxybenzyl compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl and R.sub.2 is alkenyl or alkynyl, as intermediates for the production of biocides.The preparation of the 3-phenoxybenzaldehydes employed as intermediates is described. Novel 3-phenoxybenzaldehydes used as starting materials and the production thereof are also disclosed.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: March 22, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
  • Patent number: 4348523
    Abstract: Useful thionamide compounds are prepared by reacting sulfur with imines of the structural formula: ##STR1## where R is an alkyl group of 1 to 18 carbon atoms and is other than a phenyl or cyclohexyl group, R.sub.1 and R.sub.2 are alkyl or phenyl groups of 1 to 18 carbon atoms, and R.sub.3 is a phenyl group of 6 to 18 carbon atoms or is hydrogen, in the presence of a diol or triol compound. The total number of carbons in R, R.sub.1, R.sub.2, and R.sub.3 does not exceed 36 in number.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: September 7, 1982
    Assignee: Ashland Oil, Inc.
    Inventor: Theodore C. Shields
  • Patent number: 4320142
    Abstract: Compounds of formula (I) are pesticides active against arthropods. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are H, alkyl, alkoxy, halo, CN or CF.sub.3 or two are linked to form a 3 or 4 carbon atom group;X is O or NA where A is H or alkyl;R is H or alkyl;R.sup.4 is H or optionally substituted alkyl, aryl, aralkyl, alkenyl or alkynyl; andR.sup.5 is --CB. R.sup.6 where B is O, S or NR.sup.7 where R.sup.7 is H, alkyl, alkoxy, or optionally substituted aryl or aralkyl;R.sup.6 is H, R.sup.8, OR.sup.8, SR.sup.8 or NR.sup.9 R.sup.10 where R.sup.8 is alkyl, alkenyl or optionally substituted aryl, aralkyl or aryloxyalkyl; and R.sup.9 and R.sup.10 are H, alkyl or optionally substituted aryl or aralkyl;The invention also comprises processes for the preparation of compounds (I), formulations containing them, and their use as pesticides.
    Type: Grant
    Filed: May 15, 1980
    Date of Patent: March 16, 1982
    Inventors: Malcolm H. Black, Alexander D. Frenkel, Peter T. Roberts
  • Patent number: 4282169
    Abstract: Disclosed are selected 2-acyl- or 2-thioacyl-1-trichloroacetimidoylhydrazines having the formula: ##STR1## wherein X is an atom selected from the group consisting of oxygen and sulfur; and R is a hydrogen, lower alkyl or lower alkoxy group having 1 to 4 carbon atoms, or an unsubstituted or substituted phenyl group. These compounds are disclosed to be agricultural fungicides.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: August 4, 1981
    Assignee: Olin Corporation
    Inventors: Eugene F. Rothgery, Lawrence E. Katz