Having -c(=x)-, Also In The Chain, Bonded Directly To The Nitrogen (wherein X Is Chalcogen) Patents (Class 558/392)
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Patent number: 5609848Abstract: 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: GrantFiled: September 23, 1991Date of Patent: March 11, 1997Assignee: NeoRx CorporationInventors: D. Scott Wilbur, Alan R. Fritzberg
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Patent number: 5610190Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV Protease.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: 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
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Patent number: 5602175Abstract: Hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: May 25, 1995Date of Patent: February 11, 1997Assignee: G.D. Searle & Co.Inventors: John J. Talley, Kathryn L. Reed
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Patent number: 5508436Abstract: 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: GrantFiled: October 21, 1993Date of Patent: April 16, 1996Assignee: Bayer AktiengesellschaftInventors: Reiner Fischer, Gunther Beck
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Patent number: 5496855Abstract: 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: GrantFiled: January 27, 1995Date of Patent: March 5, 1996Assignee: SmithKline Beecham Corp.Inventors: Jerry L. Adams, Ravi S. Garigipati, Margaret E. Sorenson, James D. Winkler
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Process for trans-6[2-(substituted-pyrrol-1-yl)alkyl]pyran-2-one inhibitors of cholesterol synthesis
Patent number: 5489690Abstract: 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: GrantFiled: May 15, 1995Date of Patent: February 6, 1996Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga -
Patent number: 5416111Abstract: 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: GrantFiled: December 16, 1993Date of Patent: May 16, 1995Assignee: G.D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran
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Patent number: 5416112Abstract: 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: GrantFiled: June 6, 1994Date of Patent: May 16, 1995Assignee: Roussel UclafInventor: Elizabeth A. Kuo
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Patent number: 5405987Abstract: 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: GrantFiled: March 28, 1991Date of Patent: April 11, 1995Assignee: Hoechst Celanese CorporationInventors: Varadaraj Elango, Donald R. Larkin, John R. Fritch, Michael P. Bodman, Werner H. Mueller, Bernard F. Gupton, John C. Saukaitis
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Patent number: 5389652Abstract: 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: GrantFiled: January 21, 1994Date of Patent: February 14, 1995Assignee: Roussel-UclafInventor: Elizabeth A. Kuo
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Patent number: 5389619Abstract: 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: GrantFiled: March 29, 1993Date of Patent: February 14, 1995Assignee: BASF AktiengesellschaftInventors: Reinhard Doetzer, Hubert Sauter, Horst Wingert, Reinhard Kirstgen, Albrecht Harreus, Gisela Lorenz, Eberhard Ammermann
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Patent number: 5384423Abstract: 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: GrantFiled: April 22, 1993Date of Patent: January 24, 1995Assignee: Roussel-UclafInventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully
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Patent number: 5342952Abstract: 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: GrantFiled: October 12, 1993Date of Patent: August 30, 1994Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Tung V. Le, Thomas N. Nanninga
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Patent number: 5312830Abstract: 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: GrantFiled: September 14, 1992Date of Patent: May 17, 1994Assignee: Roussel-UclafInventor: Elizabeth A. Kuo
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Patent number: 5308865Abstract: 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: GrantFiled: January 6, 1993Date of Patent: May 3, 1994Assignee: Roussel UclafInventors: Robert R. Bartlett, David P. Kay, Elizabeth A. Kuo, Rudolf Schleyerbach, Wilfried Schwab
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Patent number: 5254584Abstract: 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: GrantFiled: December 18, 1992Date of Patent: October 19, 1993Assignee: Rohm and Haas CompanyInventors: Enrique L. Michelotti, Robert R. Raney, David H. Young
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Patent number: 5246958Abstract: 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: GrantFiled: March 4, 1991Date of Patent: September 21, 1993Assignee: Mitsubishi Kasei CorporationInventors: Hiromi Okushima, Akihiro Tobe, Makio Kobayashi, Tetsuro Shimpuku, Hideki Bessho, Junko Hayashi, Asami Seino
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Patent number: 5240960Abstract: 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: GrantFiled: October 30, 1991Date of Patent: August 31, 1993Assignee: Roussel UclafInventors: Philip T. Hambleton, Charles J. R. Hedgecock, David P. Kay, Elizabeth A. Kuo, Wilfred R. Tully
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Patent number: 5185460Abstract: 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: GrantFiled: April 22, 1992Date of Patent: February 9, 1993Assignee: Nippon Soda Co., Ltd.Inventors: Seiji Tazaki, Nobuhiro Umeda, Nobuo Matsui, Tomio Yagihara, Katsunori Mikuma
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Patent number: 5175170Abstract: 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: GrantFiled: July 29, 1991Date of Patent: December 29, 1992Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5155271Abstract: 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: GrantFiled: June 25, 1990Date of Patent: October 13, 1992Assignee: Ciba-Geigy CorporationInventor: Peter Aeschlimann
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Patent number: 5140044Abstract: 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: GrantFiled: March 27, 1990Date of Patent: August 18, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Teruo Kishi, Hiromitsu Saito, Hiroshi Sano, Isami Takahashi, Tatsuya Tamaoki
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Patent number: 5130456Abstract: 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: GrantFiled: April 15, 1991Date of Patent: July 14, 1992Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
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Patent number: 5043467Abstract: 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: GrantFiled: March 5, 1990Date of Patent: August 27, 1991Assignee: Imperial Chemical Industries PLCInventors: Alan Costello, John D. Jones
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Patent number: 5041601Abstract: 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: GrantFiled: October 6, 1989Date of Patent: August 20, 1991Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
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Patent number: 5041602Abstract: 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: GrantFiled: March 29, 1990Date of Patent: August 20, 1991Assignee: Showa Denko K.K.Inventors: Kimie Nagai, Schuichi Naijoh, Ayako Kurotaki, Koro Shirane, Chozo Inoue
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Patent number: 5041637Abstract: 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: GrantFiled: July 3, 1989Date of Patent: August 20, 1991Assignee: Presidenza del Consiglio del Ministri-Ufficio del Ministro per il Coordinamento delle Iniziatjvo per la Ricerca Scientifica E. TechnologicaInventors: Vincenzo Cannata, Giancarlo Tamerlani, Claudio Calzolari
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Patent number: 5041663Abstract: 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: GrantFiled: December 11, 1990Date of Patent: August 20, 1991Assignee: Ciba-Geigy CorporationInventors: Henry Martin, Urs Fricker
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Patent number: 5034410Abstract: 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: GrantFiled: October 11, 1989Date of Patent: July 23, 1991Assignee: Syntex (U.S.A.) Inc.Inventors: Eric B. Sjogren, Michael A. Rider
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Patent number: 5024691Abstract: 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: GrantFiled: August 4, 1986Date of Patent: June 18, 1991Assignee: ICI Americas Inc.Inventor: Sreeramulu Nagubandi
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Patent number: 5021454Abstract: Benzoylaminoalkanoic acids and esters thereof are fungitoxic and useful for controlling fungi, particularly phytopathogenic fungi.Type: GrantFiled: October 6, 1989Date of Patent: June 4, 1991Assignee: Rohm and Haas CompanyInventor: Ashok K. Sharma
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Patent number: 4996346Abstract: 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: GrantFiled: October 6, 1989Date of Patent: February 26, 1991Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Harry W. Gibson, Yajnanarayana H. R. Jois
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Patent number: 4975462Abstract: Disclosed herein are novel .alpha.-arylcarbamoyl cyanoacetic esters, thioesters, and amides which exhibit anti-inflammatory/antiarthritic activities.Type: GrantFiled: July 29, 1988Date of Patent: December 4, 1990Assignee: Bristol-Myers CompanyInventor: William T. Han
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Patent number: 4960881Abstract: 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: GrantFiled: June 6, 1988Date of Patent: October 2, 1990Assignee: Societe Nationale des Poudres et ExplosifsInventors: Gerard Barcelo, Jean-Pierre Senet, Gerard Sennyey
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Patent number: 4946867Abstract: 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: GrantFiled: August 22, 1988Date of Patent: August 7, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Akio Manabe, Masato Mizutani, Kiyoto Maeda, Tadashi Ooishi, Hirotaka Takano, Osamu Kirino, deceased
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Patent number: 4921993Abstract: 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: GrantFiled: November 23, 1987Date of Patent: May 1, 1990Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Klaus Jelich, Wolfgang Kramer, Wilhelm Brandes
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Patent number: 4900349Abstract: 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: GrantFiled: April 5, 1988Date of Patent: February 13, 1990Assignee: Imperial Chemical Industries PLCInventors: Stephen P. Heaney, Patrick Crowley, Lawrence G. Reynolds
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Patent number: 4889947Abstract: 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: GrantFiled: July 28, 1988Date of Patent: December 26, 1989Assignee: ICI Americas Inc.Inventors: Charalambos J. Phalangas, Thomas P. Cleary
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Patent number: 4874846Abstract: 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: GrantFiled: May 26, 1987Date of Patent: October 17, 1989Assignee: Rhone-Poulenc Agrochimie S.A.Inventor: Alain Chene
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Patent number: 4874786Abstract: 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: GrantFiled: April 9, 1987Date of Patent: October 17, 1989Assignee: Montedison S.p.A.Inventors: Augusto Menconi, Giovanni Camaggi, Franco Gozzo, Luigi Mirenna, Carlo Garavaglia
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Patent number: 4822902Abstract: Certain N-acetonylbenzamides exhibit low toxicity to plants are particularly useful for control of fungi, especially Phycomycetes.Type: GrantFiled: July 26, 1984Date of Patent: April 18, 1989Assignee: Rohm and Haas CompanyInventors: H. Edwin Carley, Ashok K. Sharma
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Patent number: 4808628Abstract: 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: GrantFiled: November 12, 1987Date of Patent: February 28, 1989Assignee: Imperial Chemical Industries PLCInventors: Margaret C. Shephard, Patrick J. Crowley
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Patent number: 4786747Abstract: 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: GrantFiled: May 11, 1987Date of Patent: November 22, 1988Assignee: Imperial Chemical Industries PLCInventors: John D. Jones, David Schofield
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Patent number: 4785019Abstract: 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: GrantFiled: February 27, 1986Date of Patent: November 15, 1988Assignee: Chevron Research CompanyInventor: Joseph E. Moore
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Patent number: 4741846Abstract: 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: GrantFiled: July 24, 1985Date of Patent: May 3, 1988Assignee: CIBA-GEIGY CorporationInventor: Samuel Evans
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Patent number: 4734520Abstract: 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: GrantFiled: May 29, 1986Date of Patent: March 29, 1988Assignee: Vianova Kunstharz, A.G.Inventors: Helmut Plum, Willibald Paar
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Patent number: 4710514Abstract: 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: GrantFiled: April 26, 1983Date of Patent: December 1, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Katsuzo Kamoshita
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Patent number: 4709036Abstract: 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: GrantFiled: June 13, 1985Date of Patent: November 24, 1987Assignee: American Cyanamid CompanyInventors: Marinus Los, Don W. Long, Gregory P. Withers
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Patent number: 4703055Abstract: 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: GrantFiled: July 7, 1986Date of Patent: October 27, 1987Assignee: Societe d'Etudes Scientifiques et Industrielles de l'Ile-de-FranceInventors: Jacqueline Franceschini, Renee Gardaix-Luthereau, Josette Margarit
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Patent number: 4668800Abstract: 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: GrantFiled: March 4, 1985Date of Patent: May 26, 1987Assignee: Ciba-Geigy CorporationInventors: Willy Meyer, Werner F/o/ ry, Werner T/o/ pfl