Having -c(=x)-, Also In The Chain, Bonded Directly To The Nitrogen (wherein X Is Chalcogen) Patents (Class 558/392)
  • Patent number: 5609848
    Abstract: Haloaryl compounds are lithiated and thereafter metalated with one of the following organometallic groups: Sn(n--Bu).sub.3 or SnMe.sub.3. The resulting aryltin compound can be transmetalated in site-specific reaction with one of the following organometallic groups: HgX, Hg(OAc).sub.2, BX.sub.3, or BZ.sub.2, wherein X is Cl, Br, or I, and Z is alkyl or alkoxy. The metalated compounds are subsequently radiohalogenated via a demetalation reaction. A functional group suitable for conjugation to protein can be added subsequent or preferably prior to the radiohalogenation.Also compounds of the formula: R.sub.1 --Ar--R.sub.2, wherein R.sub.1 is either a radiohalogen or any one of the organometallic groups stated above, Ar is aromatic or heteroaromatic ring, and R.sub.2 is a short-chain substituent that does not activate the aromatic ring and that bears a functional group, or a precursor thereof, suitable for conjugation to protein under conditions that preserve the biological activity of the protein.
    Type: Grant
    Filed: September 23, 1991
    Date of Patent: March 11, 1997
    Assignee: NeoRx Corporation
    Inventors: D. Scott Wilbur, Alan R. Fritzberg
  • Patent number: 5610190
    Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV Protease.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 11, 1997
    Assignee: G. D. Searle & Co.
    Inventors: John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Ko-Chung Lin, Michael L. Vazquez, Richard A. Mueller, Kathryn L. Reed, Robert M. Heintz, Michael Clare, John N. Freskos, Eric T. Sun
  • Patent number: 5602175
    Abstract: Hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: February 11, 1997
    Assignee: G.D. Searle & Co.
    Inventors: John J. Talley, Kathryn L. Reed
  • Patent number: 5508436
    Abstract: The present invention relates to novel N-phenylacetamino nitriles of the general formula (I), ##STR1## in which R.sup.1 represents hydrogen, or represents alkyl, alkenyl, cycloalkyl, aryl or heterocyclyl which are in each case optionally substituted, andR.sup.2 represents hydrogen, or represents alkyl which is optionally substituted, orR.sup.1 and R.sup.2, together with the carbon atom to which they are bonded, represent cycloalkyl or heterocyclyl which are in each case optionally substituted,R.sup.3 represents halogen, alkyl or alkoxy,R.sup.4 represents hydrogen, halogen, alkyl, halogenoalkyl or alkoxy,R.sup.5 represents halogen, alkyl or alkoxy, andm represents a number 0, 1, 2 or 3, processes for their preparation and their use for the preparation of agents for controlling pests.
    Type: Grant
    Filed: October 21, 1993
    Date of Patent: April 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reiner Fischer, Gunther Beck
  • Patent number: 5496855
    Abstract: This invention relates to the novel compounds and pharmaceutical compositions of Formulas (I) and (II).This invention also relates to a method of treating or reducing inflammation in a mammal in need thereof, which comprises administering to said mammal an effective amount of a compound or composition of Formula (I) or (II).
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: March 5, 1996
    Assignee: SmithKline Beecham Corp.
    Inventors: Jerry L. Adams, Ravi S. Garigipati, Margaret E. Sorenson, James D. Winkler
  • Patent number: 5489690
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: February 6, 1996
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
  • Patent number: 5416111
    Abstract: Non-peptidyl compounds characterized generally as .alpha.-succinamidoacyl aminodiols containing a cyano group and having an N-phenyl-amino-type group at the N-terminus are useful as renin inhibitors for the treatment of hypertension.
    Type: Grant
    Filed: December 16, 1993
    Date of Patent: May 16, 1995
    Assignee: G.D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran
  • Patent number: 5416112
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of ##STR2## Z.sub.1 and Z.sub.2 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN and alkyl of 1 to 3 carbon atoms, R.sub.3 is hydrogen or alkyl of 1 to 3 carbon atoms, m is an integer from 0 to 6, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are individually selected from the group consisting of hydrogen, halogen, --CN, --NO.sub.2, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.10, --(CH.sub.2).sub.n --CX.sub.3, --O--(CH.sub.2).sub.n CX.sub.3 and --S--(CH.sub.2).sub.n --CX.sub.3, R.sub.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: May 16, 1995
    Assignee: Roussel Uclaf
    Inventor: Elizabeth A. Kuo
  • Patent number: 5405987
    Abstract: The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: April 11, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Varadaraj Elango, Donald R. Larkin, John R. Fritch, Michael P. Bodman, Werner H. Mueller, Bernard F. Gupton, John C. Saukaitis
  • Patent number: 5389652
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, W is selected from the group consisting of --O--, --S--, --SO-- and --SO.sub.2 --, Z and Y are --CH-- or one is --CH-- and the other is --N--, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, halogen, methoxy, methylthio, alkyl of 1 to 4 carbon atoms, --WCF.sub.3, --CF.sub.3, --NO.sub.2, --CN--, --W--(CH.sub.2).sub.n --CF.sub.3, --W--(CF.sub.2).sub.n --CF.sub.3, --(CF.sub.2).sub.n --CF.sub.3 and --(CH.sub.2).sub.n --CX.sub.3, n is an integer from 1 to 3, X is a halogen or R.sub.3 and R.sub.4 together are --O--(CH.sub.2)--O-- and R.sub.2, R.sub.5 and R.sub.6 are as defined above, R.sub.7 and R.sub.8 are individually hydrogen or alkyl of 1 to 6 carbon atoms, R.sub.9 is cycloalkyl of 3 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable salts with bases.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: February 14, 1995
    Assignee: Roussel-Uclaf
    Inventor: Elizabeth A. Kuo
  • Patent number: 5389619
    Abstract: Compounds of the formula I ##STR1## where n, W, X, Y, Z, R.sup.1, R.sup.2, and R.sup.3 are as defined herein exhibit fungicidal, insecticidal, and acaracidal activity.
    Type: Grant
    Filed: March 29, 1993
    Date of Patent: February 14, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhard Doetzer, Hubert Sauter, Horst Wingert, Reinhard Kirstgen, Albrecht Harreus, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5384423
    Abstract: A compound selected from the group consisting of all tautomeric forms of a cycloalkyl-propanamide of the formula ##STR1## wherein R.sub.1 is cycloalkyl of 3 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, azido, --CN, alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, --(CH.sub.2).sub.m --CF.sub.3, --O--(CH.sub.2).sub.m --CF.sub.3, --S--(CH.sub.2).sub.m --CF.sub.3, m is an integer from 0 to 3, --CF.sub.2 --Hal, --OCF.sub.2 --Hal, ##STR2## n is an integer from 1 to 3, Hal, Hal.sub.1, and Hal.sub.2 and Hal.sub.3 are individually halogen, and --COR', R' is --OH or alkyl or alkoxy of 1 to 3 carbon atoms or R.sub.4 and R.sub.5 together are --O--CH.sub.2 --O-- and their non-toxic, pharmaceutically acceptable basic salts having anti-inflammatory activity.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: January 24, 1995
    Assignee: Roussel-Uclaf
    Inventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully
  • Patent number: 5342952
    Abstract: An improved process for the preparation of trans-6-[2-(substituted-pyrrole-1-yl)alkyl]pyran-2-ones by a novel synthesis is described where .alpha.-metalated N,N-disubstituted acetamide is converted in seven operations to the desired products, and specifically, a process for preparing (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahy dro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide, as well as other valuable intermediates used in the processes and prodrugs which are bioconverted to hypolipidemic and hypocholesterolemic agents and pharmaceutical compositions of the same.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: August 30, 1994
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
  • Patent number: 5312830
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, W is selected from the group consisting of --O--, --S--, --SO-- and --SO.sub.2 --, Z and Y are --CH-- or one is --CH-- and the other is --N--, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are individually selected from the group consisting of hydrogen, halogen, methoxy, methylthio, alkyl of 1 to 4 carbon atoms, --WCF.sub.3, --CF.sub.3, --NO.sub.2, --CN--, --W--(CH.sub.2).sub.n --CF.sub.3, --W--(CF.sub.2).sub.n --CF.sub.3, --(CF.sub.2).sub.n --CF.sub.3 and --(CH.sub.2).sub.n --CX.sub.3, is an integer from 1 to 3, X is a halogen or R.sub.3 and R.sub.4 together are --O--(CH.sub.2)--O-- and R.sub.2, R.sub.5 and R.sub.6 are as defined above, R.sub.7 and R.sub.8 are individually hydrogen or alkyl of 1 to 6 carbon atoms, R.sub.9 is cycloalkyl of 3 to 6 carbon atoms and their non-toxic, pharmaceutically acceptable salts with bases.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: May 17, 1994
    Assignee: Roussel-Uclaf
    Inventor: Elizabeth A. Kuo
  • Patent number: 5308865
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of ##STR2## R.sub.13, R.sub.14 and R.sub.15 are individually selected from the group consisting of hydrogen, halogen and alkyl of 1 to 3 carbon atoms, n is an integer from 1 to 3, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4 R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, alkylcarbonyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, ##STR3## m is 0, 1, 2 or 3, n is 1, 2 or 3; Hal, Hal.sub.1, Hal.sub.2 and Hal.sub.3 are individually halogen and ##STR4## R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are individually any of the groups defined above for R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 or R.sub.4 and R.sub.5 together form --O--CH.sub.
    Type: Grant
    Filed: January 6, 1993
    Date of Patent: May 3, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert R. Bartlett, David P. Kay, Elizabeth A. Kuo, Rudolf Schleyerbach, Wilfried Schwab
  • Patent number: 5254584
    Abstract: Certain N-acetonylbenzamides exhibit low phytotoxicity and are useful for control of a wide range of fungi, including phytopathogenic fungi of the classes Oomycetes, Ascomycetes, Deuteromycetes and Basidiomycetes.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: October 19, 1993
    Assignee: Rohm and Haas Company
    Inventors: Enrique L. Michelotti, Robert R. Raney, David H. Young
  • Patent number: 5246958
    Abstract: Disclosed are antihypertensive pharmaceutical compositions and compounds which include the thiocarbamoylacetonitrile having the formula: ##STR1## wherein: R.sup.1 is selected from the group consisting of hydrogen, a C.sub.1 to C.sub.6 alkyl, a C.sub.3 to C.sub.6 cycloalkyl or --(CH.sub.2).sub.n --A (where A is selected from the group consisting of a C.sub.6 to C.sub.12 aryl, a 5- or 6-membered heterocyclic group or a fused heterocyclic group constituted by 9 or 10 atoms, each of which may be substituted by at least one substitute group selected from a C.sub.1 to C.sub.6 alkyl and a halogen and n is 0 or an integer of 1 to 6),R.sup.2 represents a C.sub.1 to C.sub.10 alkyl, and Ar represents an aryl, a 5- or 6-membered heterocyclic group or a fused heterocyclic group, each of which may be substituted by at least one substituent group selected from the group consisting of a C.sub.1 to C.sub.6 alkyl, a C.sub.1 to C.sub.6 alkoxy, a C.sub.2 to C.sub.7 alkylcarbonyl, a C.sub.7 to C.sub.
    Type: Grant
    Filed: March 4, 1991
    Date of Patent: September 21, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hiromi Okushima, Akihiro Tobe, Makio Kobayashi, Tetsuro Shimpuku, Hideki Bessho, Junko Hayashi, Asami Seino
  • Patent number: 5240960
    Abstract: A compound selected from the group consisting of all tautomeric forms of a cycloalky-propanamide of the formula ##STR1## wherein R.sub.1 is cycloalkyl of 3 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, azido, --CN, alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, --(CH.sub.2).sub.m --CF.sub.3, --O--(CH.sub.2).sub.m --CF.sub.3, --S--(CH.sub.2).sub.m --CF.sub.3, m is an integer from 0 to 3, --CF.sub.2 --Hal, --OCF.sub.2 --Hal, ##STR2## n is an integer from 1 to 3, Hal, Hal.sub.1, Hal.sub.2 and Hal.sub.3 are individually halogen, and --COR', R' is --OH or alkyl or alkoxy of 1 to 3 carbon atoms or R.sub.4 and R.sub.5 together are --O--CH.sub.2 --O-- and their non-toxic, pharmaceutically acceptable basic salts having anti-inflammatory activity.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: August 31, 1993
    Assignee: Roussel Uclaf
    Inventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully
  • Patent number: 5185460
    Abstract: Aminoacetonitrile derivatives, where the 2-position of aminoacetonitrile is optionally substituted by alkylthio groups, arylthio groups and heterocyclicthio groups. The process for making such compounds comprises reacting hydrogen cyanide with the desired corresponding R-S-H and recovering the crystallized salt thereof. The aminoacetonitrile derivatives are useful as starting materials to produce pharmaceutical and agricultural intermediates such as benzomide derivatives with fungicidal and herbicidal activities.
    Type: Grant
    Filed: April 22, 1992
    Date of Patent: February 9, 1993
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Seiji Tazaki, Nobuhiro Umeda, Nobuo Matsui, Tomio Yagihara, Katsunori Mikuma
  • Patent number: 5175170
    Abstract: Non-peptidyl compounds characterized generally as cycloalkyl/cycloalkylkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest of the formula ##STR1## wherein R.sub.1 is selected from cycloalkyl and cycloakylalkyl groups, wherein said cycloalkyl group contains three to about eight carbon atoms and the acyclic alkyl portion of said cycloakylalkyl group contains one to about eight carbon atoms; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: December 29, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
  • Patent number: 5155271
    Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## in which Q is substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, A is a direct bond or a bridging member, s is the number 1 or 2, Z is a radical of the formula --CH.sub.2 CH.sub.2 OH, --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, and Y is a leaving group, and the benzene or napthalene nucleus I can be further substituted, which comprises reacting compounds of the formula ##STR2## with compounds of the formulaQ--OH (3)in which A, s, Z and Q are as defined under formula (1), in the presence of hydrogenation catalysts, and then carrying out further conversion reactions where appropriate.The compounds obtained by the process according to the invention are suitable as intermediates for the preparation of reactive dyes.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Aeschlimann
  • Patent number: 5140044
    Abstract: A UCN-1028D derivative represented by the formula: ##STR1## has protein kinase C inhibitory activity and is expected to be used as an active ingredient in anti-tumor agents, etc.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: August 18, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Teruo Kishi, Hiromitsu Saito, Hiroshi Sano, Isami Takahashi, Tatsuya Tamaoki
  • Patent number: 5130456
    Abstract: A bis Reissert can be formed by the initial reaction of an aliphatic or aromatic aldehyde (e.g., propionaldehyde) and primary amine (e.g., methylamine) to form a reaction product which is then reacted with a diacid chloride (e.g., adipoyl chloride).
    Type: Grant
    Filed: April 15, 1991
    Date of Patent: July 14, 1992
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
  • Patent number: 5043467
    Abstract: A process for the production of a substituted amide of the formula: ##STR1## where R.sup.1 is an optionally substituted aryl group, X.sup.1 is --O-- or --S-- and R.sup.2 is an optionally substituted alkyl, alkenyl, or alkynyl group or X.sup.1 R.sup.2 is an N-linked 5-membered nitrogen heterocycle comprising the halogenation, preferably bromination, in an inert solvent of a N-cyanomethyl-amide of the formula R.sup.1 --CONH.CH.sub.2 CN, followed by addition to the halogenated mixture, or to the mixture as halogenation is taking place, of a heterocyclic tertiary amine in a proportion of from about 1.0 to about 2.5 moles, and preferably from 1.3 to 2.1 moles, for each mole of halogen reacted, and finally treatment of the resulting quaternary salt with an alcohol, thiol or amine of the formula R.sup.2 X.sup.1 H.
    Type: Grant
    Filed: March 5, 1990
    Date of Patent: August 27, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Alan Costello, John D. Jones
  • Patent number: 5041601
    Abstract: A bis Reissert can be formed by the initial reaction of an aromatic dialdehyde (e.g., terephthaldicaboxaldehyde) and primary amine (e.g., methylamine) to form a reaction product which is then reacted with an acid chloride (e.g., benzoyl chloride).
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: August 20, 1991
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
  • Patent number: 5041602
    Abstract: A novel amino acid derivative is disclosed, which is produced using a relatively inexpensive amino acid as a starting material for an optically active moiety and shows a chiral nematic phase or a chiral smectic phase over a wide temperature range around room temperature. A process for producing the amino acid derivative is also disclosed.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: August 20, 1991
    Assignee: Showa Denko K.K.
    Inventors: Kimie Nagai, Schuichi Naijoh, Ayako Kurotaki, Koro Shirane, Chozo Inoue
  • Patent number: 5041637
    Abstract: New process for the synthesis of optically active aminoacids of formula ##STR1## by treating compounds of formula ##STR2## which an optically active alcohol of formulaR.sub.4 --OH (III)d or 1To obtain a pair of diastereoiosmer esters of formula ##STR3## which is resolved in basic medium into the single diastereoisomer esters of formula ##STR4## from which the desired optically active aminoacid of formula (I) is obtained by treatment in acid medium.
    Type: Grant
    Filed: July 3, 1989
    Date of Patent: August 20, 1991
    Assignee: Presidenza del Consiglio del Ministri-Ufficio del Ministro per il Coordinamento delle Iniziatjvo per la Ricerca Scientifica E. Technologica
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Claudio Calzolari
  • 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: 5034410
    Abstract: This invention is directed to a method for treating helminthiasis in an animal which method comprises administering to an animal in need thereof an anthelmintically effective amount of a compound of the Formula (I): ##STR1## wherein Z is oxygen or sulfur;R.sup.1 is hydrogen or lower alkyl; andR.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, halo, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, cyano, halophenoxy, haloalkylphenoxy, thiocyano or isothiocyano, provided that R.sup.2 and R.sup.3 cannot simultaneously be hydrogen and that R.sup.4 and R.sup.5 cannot simultaneously be hydrogen; or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions formulated therewith. This invention is also directed to novel anthelmintically active benzenepropanamides of Formula (I) wherein Z is oxygen.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: July 23, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Eric B. Sjogren, Michael A. Rider
  • Patent number: 5024691
    Abstract: As new compounds, substituted aryloxyphenoxy benzamides having the formula ##STR1## in which X is CH or nitrogen; Y is chlorine, bromine, fluorine, iodine, methyl, cyano or hydrogen; Z is hydrogen, chlorine, bromine, fluorine, iodine, CH.sub.n, F.sub.3-n where n is an integer from 0 to 3; R is nitrogen dioxide, hydrogen or halogen; R' is hydrogen, CH.sub.3, lower alkyl, having 1-10 carbon atoms, SCCl.sub.3, ##STR2## or --PO.sub.3 R.sup.3.sub.2 wherein R.sup.3 is hydrogen, alkyl having 1-10 carbon atoms, aryl, or an equivalent of base such as a salt; R" is cyano, --C.tbd.CH, ##STR3## wherein R.sup.4 is hydrogen, alkyl having 1-10 carbon atoms, aryl or an equivalent of base such as a salt; and m is 0, 1, 2 or 3.
    Type: Grant
    Filed: August 4, 1986
    Date of Patent: June 18, 1991
    Assignee: ICI Americas Inc.
    Inventor: Sreeramulu Nagubandi
  • Patent number: 5021454
    Abstract: Benzoylaminoalkanoic acids and esters thereof are fungitoxic and useful for controlling fungi, particularly phytopathogenic fungi.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: June 4, 1991
    Assignee: Rohm and Haas Company
    Inventor: Ashok K. Sharma
  • Patent number: 4996346
    Abstract: Bis Reissert compounds can be formed by reaction of a cyanohydrin, formed by reaction of an aldehyde and a diamine, with benzoyl chloride in the presence of an amine acid acceptor.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: February 26, 1991
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
  • Patent number: 4975462
    Abstract: Disclosed herein are novel .alpha.-arylcarbamoyl cyanoacetic esters, thioesters, and amides which exhibit anti-inflammatory/antiarthritic activities.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: December 4, 1990
    Assignee: Bristol-Myers Company
    Inventor: William T. Han
  • Patent number: 4960881
    Abstract: The invention relates to carbonates of formula: ##STR1## in which X is a fluorine, chlorine or bromine atom and R.sup.1 is different from the ##STR2## group and represents: a substituted or non-substituted, saturated or unsaturated, aliphatic, araliphatic, primary, secondary, tertiary or cycloaliphatic radical. These .alpha.-chlorinated carbonates are prepared by the action of a compound of formula R.sup.1 OH on a chloroformate of formula: ##STR3## in a solvent medium in the presence of an acid scavenger which is added after the two preceding compounds. They are used to block the amine function of amino acids. The .alpha.-chlorinated carbonate and amino acid are reacted in a solvent medium at a temperature of -5.degree. to 100.degree. C. in the presence of an acid scavenger. Blocked amines are very useful in peptide synthesis.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: October 2, 1990
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
  • Patent number: 4946867
    Abstract: A cyanoacetamide derivative of the formula, ##STR1## wherein R represents a C.sub.2 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or C.sub.3 -C.sub.6 cycloalky group, and X represents a chlorine or bromide atom or a trifluoromethyl or lower fluoroalkoxy group and a plant disease protectant comprising the same are disclosed. The cyanoacetamide derivative provided according to the present invention has an extremely high controlling activity against various plant diseases, particularly against rice blast (Pyricularia oryzae).
    Type: Grant
    Filed: August 22, 1988
    Date of Patent: August 7, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akio Manabe, Masato Mizutani, Kiyoto Maeda, Tadashi Ooishi, Hirotaka Takano, Osamu Kirino, deceased
  • Patent number: 4921993
    Abstract: Fungicidally active substituted benzamides of the formula ##STR1## in which R.sup.1 represents alkoxy, alkenyloxy, alkinyloxy or a heterocyclyl radical,R.sup.2 represents cyano, a carbamoyl radical or a thiocarbamoyl radical,X represents an alkanoyl radical or an alkoximinoalkyl radical, andn represents a number 1, 2 or 3.Intermediates wherein R' is replaced by bromine and R.sup.2 is cyano or a carbamoyl radical are also new.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: May 1, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Klaus Jelich, Wolfgang Kramer, Wilhelm Brandes
  • Patent number: 4900349
    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 CSNH.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: April 5, 1988
    Date of Patent: February 13, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Stephen P. Heaney, Patrick Crowley, Lawrence G. Reynolds
  • Patent number: 4889947
    Abstract: Sunscreen compositions are described which contain certain substituted naphthalenylidenes which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: December 26, 1989
    Assignee: ICI Americas Inc.
    Inventors: Charalambos J. Phalangas, Thomas P. Cleary
  • Patent number: 4874846
    Abstract: Process for the preparation of aryloxy-benzoic acids containing a sulphonamide group by the direct reaction of a phenoxy-benzoic acid with a sulphonamide, in the presence of a halogenating agent such as P(O)Cl.sub.3.
    Type: Grant
    Filed: May 26, 1987
    Date of Patent: October 17, 1989
    Assignee: Rhone-Poulenc Agrochimie S.A.
    Inventor: Alain Chene
  • Patent number: 4874786
    Abstract: A method of fighting fungus infections by using compounds having the formula: ##STR1## wherein: R is H, a C.sub.1 -C.sub.4 alkyl, an alkenyl, or an alkynyl radical; n is 1 or 2;A represents a C.sub.1 -C.sub.6 alkylene bridge, an arylene or a heterocyclic bridge;X represents O, S, SO, SO.sub.2 ; andR.sup.1 is selected from the group consisting of C.sub.1 -C.sub.6 alkyl radicals, a phenyl radical, optionally substituted, polyfluoroalkyl radicals containing from 1 to 4 carbon atoms and at least 2 fluorine atoms, polyfluoroalkenyl radicals containing from 2 to 4 carbon atoms and at least 2 fluorine atoms, but excluding compounds having the formula (I) wherein A is an alkylene radical, n is 2, and R.sup.1 is a C.sub.1 -C.sub.6 alkyl radical.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: October 17, 1989
    Assignee: Montedison S.p.A.
    Inventors: Augusto Menconi, Giovanni Camaggi, Franco Gozzo, Luigi Mirenna, Carlo Garavaglia
  • Patent number: 4822902
    Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: April 18, 1989
    Assignee: Rohm and Haas Company
    Inventors: H. Edwin Carley, Ashok K. Sharma
  • 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: 4786747
    Abstract: Benzamides of the formula (I): ##STR1## in which Ar is optionally substituted aryl; X is O, S or NH and R is optionally substituted alkyl or alkenyl when X is O or S, or is optionally substituted alkanoyl when X is NH, are prepared by(a) reacting a compound of the formula (II):ArCONHCH.sub.2 CN (II)with a brominating agent in a solvent which is substantially chemically inert to the reactants and in which compound (II) is soluble, to form a compound of the formula (III): ##STR2## and (b) reacting the compound (III) with a compound RXH.Preferably, bromination is carried out rapidly in dried ethyl acetate.The process avoids hydration of the CN group of the compound (III) to a carbamoyl group obviating a subsequent dehydration step later.The intermediate compound (III) is novel.The substituted benzamides are useful as herbicides and fungicides.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: November 22, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: John D. Jones, David Schofield
  • Patent number: 4785019
    Abstract: N-cyanoalkyl-N-haloalkylthio alkyl-, aryl- and aralkyl-carboxamides of the general formula: ##STR1## wherein R is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, lower alkenyl of 2 to 6 carbon atoms or lower alkynyl of 2 to 6 carbon atoms, all optionally substituted with 1 to 4 halogen atoms; lower alkoxyalkylene; aryl of 6 to 12 carbon atoms; aralkyl of 7 to 16 carbon atoms; or substituted aryl or substituted aralkyl both substituted with 1 to 3 substituents independently selected from phenyl, lower alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, lower alkylthio of 1 to 6 carbon atoms, halogen, nitro, cyano, ##STR2## wherein R.sup.4 is hydrogen or lower alkyl of 1 to 6 carbon atoms, ##STR3## wherein R.sup.5 and R.sup.6 are independently hydrogen or lower alkyl of 1 to 6 carbon atoms; R.sup.1 and R.sup.2 are independently hydrogen, or lower alkyl of 1 to 6 carbon atoms; and R.sup.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: November 15, 1988
    Assignee: Chevron Research Company
    Inventor: Joseph E. Moore
  • Patent number: 4741846
    Abstract: Novel compounds of the formula I ##STR1## are described. The radicals R.sup.1, R.sup.2 and R.sup.3 are hydroxyl-substituted alkyl, --C(R.sup.4 R.sup.5)--(CHR.sup.6).sub.m --W, --(CH.sub.2).sub.2 --OCOR.sup.10 or ##STR2## and W is --COR.sup.7, --COOR.sup.7, --CON(R.sup.9 R.sup.15) or CN. The other radicals are customary hydrocarbon radicals.The novel substances can be employed as stabilizers for organic polymers or for lubricants.
    Type: Grant
    Filed: July 24, 1985
    Date of Patent: May 3, 1988
    Assignee: CIBA-GEIGY Corporation
    Inventor: Samuel Evans
  • Patent number: 4734520
    Abstract: Crosslinking components for hydroxy and/or primary and/or secondary amino group containing paint binders for the crosslinking of synthetic resins carrying at least two groups capable of ester or amide formation with carboxylic acids. In particular there is disclosed the use of the crosslinking components in compositions for electrodeposition (ED) whereby at 120.degree. C. and above coatings with extraordinary paint performance are obtained. The use of methyl or ethyl esters gives extremely low condensation losses. The crosslinking components are obtained through reaction of one mole of a diisocyanate, preferably at room temperature, in the presence of sodium, or preferably sodium phenolate, as catalyst, with at least one mole of a CH-active alkyl ester of the general formula X--CH.sub.2 --COOR, wherein X is --COOR, --CN or CH.sub.3 --CO-- and R is an alkyl radical with 1 to 8 C-atoms and subsequent reaction of the free isocyanate groups with polyamines of the general formula H.sub.2 N--(R--NH).sub.n --R--NH.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: March 29, 1988
    Assignee: Vianova Kunstharz, A.G.
    Inventors: Helmut Plum, Willibald Paar
  • Patent number: 4710514
    Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or dicarboximide fungicides.
    Type: Grant
    Filed: April 26, 1983
    Date of Patent: December 1, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Toshiro Kato, Katsuzo Kamoshita
  • Patent number: 4709036
    Abstract: The present invention provides a process for the preparation of herbicidal 2-(4,4-disubstituted-5-oxo-2-imidazolin-2-yl) benzoic, nicotinic and quinoline-3-carboxylic acids, esters and salts.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: November 24, 1987
    Assignee: American Cyanamid Company
    Inventors: Marinus Los, Don W. Long, Gregory P. Withers
  • Patent number: 4703055
    Abstract: The invention concerns novel benzamides and their pharmacologically acceptable salts which are useful as gastromotor agents and correspond to the following general formula (I): ##STR1## in which: R.sub.1 is lower alkyl, lower alkenyl or a hydrogen atom;R.sub.2 is alkyl, lower alkenyl, benzyl, cycloalkylalkyl, cycloalkenylalkyl or a hydrogen atom;R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 each are lower alkyl or a hydrogen atom, andX is a halogen atom.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: October 27, 1987
    Assignee: Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-France
    Inventors: Jacqueline Franceschini, Renee Gardaix-Luthereau, Josette Margarit
  • Patent number: 4668800
    Abstract: There is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: May 26, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner F/o/ ry, Werner T/o/ pfl