The -c(=x)- Is Part Of A -c(=x)x- Group, Wherein The X's Are The Same Of Diverse Chalcogens Patents (Class 546/341)
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Patent number: 5061716Abstract: Compounds having the structure ##STR1## wherein: R and R.sup.1 are each independently members selected from the group consisting ofC.sub.1 -C.sub.10 alkyl,C.sub.1 -C.sub.10 cyanoalkyl,C.sub.7 -C.sub.13 arylalkyl,C.sub.2 -C.sub.9 alkenyl,C.sub.3 -C.sub.9 haloalkenylC.sub.3 -C.sub.10 alkoxyalkyl,C.sub.3 -C.sub.10 alkylthioalkyl,C.sub.3 -C.sub.10 alkylsulfonylalkyl,C.sub.3 -C.sub.8 carbalkoxyalkyl,C.sub.4 -C.sub.10 alkylenedioxyalkyl,C.sub.7 -C.sub.13 aryloxyalkyl, andC.sub.5 -C.sub.8 alkenyloxyalkyl; andR.sup.2 is C.sub.1 -C.sub.5 alkyl,are disclosed which have fungicidal activity. Fungicidal compositions comprising the compounds and a carrier are also disclosed, as are methods for controlling the growth of phytopathogenic fungi utilizing the compounds. Methods for the preparation of such compounds are also disclosed.Type: GrantFiled: September 13, 1990Date of Patent: October 29, 1991Assignee: Uniroyal Chemical Company, Inc.Inventors: Douglas I. Relyea, Robert A. Davis
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Patent number: 5057518Abstract: The synthesis and application of N(1)-n-alkyl-pyrimidinium-salts are described. These surfactants have a very small critical micelle concentration (CMC) in the order of 10.sup.-5 -10.sup.-7 Mol/Liter. These N(1)-n-alkyl-pyrimidinium components have pharmacological activities and can act as antimetabolites.Type: GrantFiled: May 24, 1990Date of Patent: October 15, 1991Assignee: Medice Hem.-Pharm. Fabrik Putter GmbH & Co. KGInventor: Henrich H. Paradies
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Patent number: 5041613Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.Type: GrantFiled: August 28, 1989Date of Patent: August 20, 1991Assignee: Eastman Kodak CompanyInventor: Charles A. McCombs
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Patent number: 5039810Abstract: (E)-methyl 2-(2-chloropyrid-3-yl)-3-methoxypropenoate.Type: GrantFiled: October 17, 1988Date of Patent: August 13, 1991Assignee: Imperial Chemical Industries PLCInventors: Kenneth Anderson, John M. Clough, Christopher R. A. Godfrey
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Patent number: 5017583Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: February 23, 1988Date of Patent: May 21, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
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Patent number: 5008276Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 5004743Abstract: Compounds having the formula: ##STR1## are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.Type: GrantFiled: November 25, 1987Date of Patent: April 2, 1991Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Robert Zamboni, Jacques Y. Gauthier
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Patent number: 5002694Abstract: Nitrogen-containing heterocyclic compounds of the formula II ##STR1## wherein R.sup.1 and R.sup.2 in each case denote an alkyl group having 1 to 15 C atoms, wherein one or more CH.sub.2 groups may also be replaced by a grouping selected from the group comprising --O--, --S--, --CO--, --O--CO--, --O--COO--, --CO--O--, --CH.dbd.CH--, --CH--halogen and --CHCN--, or else by a combination of two suitable groupings, two heteroatoms not being directly linked to each other,m denotes 0 or 1,Ar denotes 1,4-phenylene, 4,4'-biphenylyl or 2,6-naphthylene, wherein one or more CH groups are in each case replaced by N,Z denotes --C--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CHCN--, --CHCNCH.sub.2 --, --CH.dbd.CH or a single bond, andA denotes unsubstituted 1,4-cyclonexylene or 11,4-cyclohexylene substituted in position 1 or position 4 by CN,with the proviso that if A=unsubstituted 1,4-cyclonexylene, Z denotes --CHCNCH.sub.2 -- or --CH.sub.2 CHCN-- and/or at least one CH.sub.Type: GrantFiled: May 13, 1987Date of Patent: March 26, 1991Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Bernhard Scheuble
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Patent number: 5001156Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.Type: GrantFiled: December 1, 1987Date of Patent: March 19, 1991Assignee: L'OrealInventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
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Patent number: 4997837Abstract: Certain trans-6-[[(substituted)pyridin-3-yl]-alkyl- and alkenyl]tetrahydro-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.Type: GrantFiled: October 6, 1989Date of Patent: March 5, 1991Assignee: Warner-Lambert CompanyInventors: Alexander W. Chucholowski, Mark W. Creswell, Bruce D. Roth, Drago R. Sliskovic
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Patent number: 4987053Abstract: Compounds of the general formula I ##STR1## are described in which Q denotes ##STR2## R denotes alkyl, hydroxyalkyl or aryl, R.sup.1 and R.sup.2 denote H, alkyl or alkoxyalkyl,R.sup.3 denotes H, methyl or ethyl,D.sup.1 and D.sup.2 denote saturated hydrocarbon groups,E denotes alkylene, cycloalkylene, arylene, saturated or unsaturated heteroyls or a group of the formula II ##STR3## a and b denote integers from 1 to 4. c denotes an integer from 1 to 3,m denotes 2, 3 or 4, depending on the valency of Q, andn denotes an integer from 1 to m, where all radicals of the same definition may be identical to or different from one another.The compounds are suitable as polymerizable compounds for photopolymerizable mixtures and are distinguished by ready polymerizability in combination with photoinitiators and long shelf lives in the layer.Type: GrantFiled: November 14, 1988Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Joachim Gersdorf, Klaus Rose
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Patent number: 4977059Abstract: A method for forming microcapsules by enwrapping an oily core material in a formaldehyde condensation product formed in situ wherein a dispersant is used of the formula (I): ##STR1## where: M is an alkali metal cation or a quaternary ammonium group,L is --(CH.sub.2).sub.p, --COO(CH.sub.2).sub.p, --C.sub.6 H.sub.4 -- or a direct bond;R, R.sup.2 and R.sup.6 are the same or different and represent a hydrogen atom or a methyl group;R.sup.1 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or --SO.sub.3 M where M is defined as above; R.sup.3 is --COOR.sup.4, --CONHR.sup.4, --CO--R.sup.4, a pyridinyl group or quaternary salt thereof, --COOCH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 --, --COOCH.sub.2 CH.sub.2 N.sub.4 (CH.sub.3).sub.3 Cl-- group having 1 to 12 carbon atoms, an aralkyl group, an aryl group, or --(CH.sub.2).sub.m --OOC--CR.sup.2 CH.sub.2, --(OCH.sub.2 CHhd 2).sub.m COO--CR.sup.2 CH.sub.2 or --(CH.sub.2).sub.m NHCO--CR.sup.2 CH.sub.2 ;x is about 0.4 to 0.8;y is about 0.2 to 0.6;z is about 0 to 0.Type: GrantFiled: May 12, 1989Date of Patent: December 11, 1990Assignee: The Mead CorporationInventors: Rong-Chang Liang, William H. Simpson, Katherine A. Gyure, Kenneth P. Carpenter
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Patent number: 4977279Abstract: A process for the preparation of optically active 3-demethylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups.Type: GrantFiled: November 20, 1989Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4970313Abstract: A process for the preparation of optically active 3-de-methylmevalonic acid derivatives, and intermediates A process for the preparation of optically active 3-de-methylmevalonic acid derivatives of the formula I ##STR1## (3,5-dihydroxy carboxylic acid derivatives) or of the formula II ##STR2## (.beta.-hydroxy lactones) in which R, R.sup.1 and Y have the indicated meanings, is described. The invention furthermore relates to aldehydes of the formula XII ##STR3## in which M represents the indicated protective groups. The 3-demethylmevalonic acid derivatives of this invention are useful for lowering cholesterol levels of a host.Type: GrantFiled: December 6, 1988Date of Patent: November 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunther Wess, Kurt Kesseler, Ekkehard Baader, Gerhard Beck
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Patent number: 4950675Abstract: Certain trans-6,6'-[[(substituted)pyridin-3,5-diyl]-dialkane- and dialkene-diyl]bis [tetrahydro-4-hydroxypyran]-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methyl-glutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.Type: GrantFiled: December 21, 1988Date of Patent: August 21, 1990Assignee: Warner-Lambert CompanyInventor: Alexander Chucholowski
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Patent number: 4945098Abstract: A derivative of 2-methylenepropane-1,3-diol of the general formula I ##STR1## where O--A.sup.1 and O--A.sup.2, which can be the same or different, each represents O, O--C(O), O--C(O)NH, O--C(S)NH or O--C(O)O, R.sup.1 represents an alkyl or alkenyl group of 10-22 carbon atoms, n is an integer from 1 to 11, B.sup.+ represents a quaternary ammonium group, either N.sup.+ R.sup.4 R.sup.5 R.sup.6, or N.sup.+ (Het), where R.sup.4, R.sup.5 and R.sup.6 are similar or different alkyl groups of 1-4 carbon atoms, or two or all of R.sup.4, R.sup.5 and R.sup.6 may be incorporated into a cyclic or bicyclic structure, which may contain additional hetero atoms; X.sup.- means the anion of a pharmceutically acceptable inorganic or organic acid; and R.sup.2 and R.sup.3 are the same or different, and represent hydrogen or alkl groups of 1-4 carbon atoms.Type: GrantFiled: July 10, 1987Date of Patent: July 31, 1990Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Gunnar Grue-Sorensen, Christian K. Nielsen
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Patent number: 4942171Abstract: An antidiabetic agent is disclosed, which comprises a compound represented by formula (I): ##STR1## wherein R represents an imidazolyl group, a thiazolyl group or a pyridyl group; n represents 1 or 2; and m represents an integer of from 1 to 4, or a pharmaceutically acceptable salt thereof as an active ingredient.Type: GrantFiled: July 6, 1988Date of Patent: July 17, 1990Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Hidemi Masumura, Kyoko Sakuma, Shinichiro Ashida
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Patent number: 4935430Abstract: Platelet activating factor antagonists of formula (I): ##STR1## wherein R is phenyl or phenyl substituted by one or more substituents selected from nitro, halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl (C.sub.1 -C.sub.4) alkoxy, fluoro (C.sub.1 -C.sub.4) alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulphonyl, hydroxy, trifluoromethyl and cyano, or is phenyl fused to a dioxole ring;R.sup.1 and R.sup.2 are each independently H or C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.2 together complete a pyrrolidinyl, piperidino, morpholino, piperazinyl, N-(C.sub.1 -C.sub.4 alkyl) piperazinyl or N-(C.sub.2 -C.sub.4 alkanoyl)-piperazinyl group;orR.sup.2 is H or C.sub.1 -C.sub.4 alkyl and R.sup.1 is CN, C.sub.3 -C.sub.7 cycloalkyl, aryl, heteroaryl or a C.sub.1 -C.sub.4 alkyl group substituted by one or more substituents selected from C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, aryl or heteroaryl;Z is selected from C.sub.1 -C.sub.6 alkoxy, aryl (C.sub.1 -C.sub.Type: GrantFiled: September 29, 1988Date of Patent: June 19, 1990Assignee: Pfizer Inc.Inventors: Kelvin Cooper, Michael J. Fray, Kenneth Richardson, John Steele
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Patent number: 4929751Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.Type: GrantFiled: October 19, 1987Date of Patent: May 29, 1990Assignee: Yale UniversityInventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
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Patent number: 4925852Abstract: 3-Demethylmevalonic acid derivatives of the formula I (.delta.-lactone) and II (corresponding dihydroxy carboxylic acid derivative) ##STR1## in which A--B, Z, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the indicated meanings, a process for the preparation of these compounds, their use as medicaments, and pharmaceutical products, are described. In addition, new intermediates for the preparation of the compounds of the formula I and formula II are described.Type: GrantFiled: July 8, 1988Date of Patent: May 15, 1990Assignee: Hoechst AktiengesellschaftInventors: Kurt Kesseler, Gerhard Beck, Wilhelm Bartmann, Ernold Granzer
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Patent number: 4902796Abstract: 2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a halo-aromatic compound and an unsaturated compound in the prosence of a palladium catalyst. The products are chemical intermediates for the preparation of antineo-plastic agents.A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.Type: GrantFiled: August 8, 1988Date of Patent: February 20, 1990Assignee: The Trustees of Princeton UniversityInventors: Edward C. Taylor, George S. K. Wong
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Patent number: 4889953Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.Type: GrantFiled: July 22, 1987Date of Patent: December 26, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
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Patent number: 4876026Abstract: An optically active-2-methylbutyrate capable of imparting a spontaneous polarization value to achiral smectic compositions and also constituting ferroelectric liquid crystal compositions exhibiting a fast response at room temperature, and a liquid crystal composition containing the same, and further a light-switching element therefrom, are provided, which optically active-2-methylbutyrate is expressed by the formula ##STR1## wherein R represents a linear or branched alkyl group or alkoxy group, each of 1 to 18 carbon atoms; A represents ##STR2## wherein X represents any one of F, Cl, Br or cyano group; and * indicates an optically active carbon atom.Type: GrantFiled: December 15, 1987Date of Patent: October 24, 1989Assignee: Chisso CorporationInventors: Shinichi Saito, Hiromichi Inoue, Kazutoshi Miyazawa, Kouji Ohno, Makoto Ushioda
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Patent number: 4873362Abstract: 2-Substituted 4-acyloxy-2-butenals of the general formula I ##STR1## where R.sup.1 is alkyl of 1 to 12 carbon atoms which may be substituted by cycloalphatic, aromatic or heterocyclic radicals, by alkenyl or alkynyl or by hydroxyl, ether, thioether, acetoxy acyl, alkylamino, carboxyl or carbalkoxy, and R.sup.2 is acyloxy, are prepared by reacting a monosubstituted acetaldehyde of the general formula II ##STR2## where R.sup.2 has the abovementioned meaning, with an aldehyde of the general formula III ##STR3## where R.sup.1 has the abovementioned meaning, in the presence of a linear or cyclic secondary amine and of an organic acid at from 20.degree. to 100.degree. C.Type: GrantFiled: November 2, 1987Date of Patent: October 10, 1989Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler
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Patent number: 4834904Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: December 24, 1986Date of Patent: May 30, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 4826531Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.Type: GrantFiled: April 17, 1987Date of Patent: May 2, 1989Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 4818819Abstract: 2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a haloaromatic compound and an unsaturated compound in the presence of a palladium catalyst. The products are chemical intermediates for the preparation of antineoplastic agents.A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.Type: GrantFiled: October 20, 1986Date of Patent: April 4, 1989Assignee: The Trustees of Princeton UniversityInventors: Edward C. Taylor, George S. K. Wong
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Patent number: 4814458Abstract: This invention relates to a novel process for preparing 4-acetyl-1-methyl-7-pyridyl-5,6,7,8-tetrahydro-3(2H)-isoquinolinone characterized by condensing 2-acetyl-4-pyridyl cyclohexanone with acetoacetamide. This compound is useful as pharmaceuticals, particularly cardiotonics.Type: GrantFiled: February 2, 1987Date of Patent: March 21, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Nobuyuki Fukazawa, Tatsuo Kaiho, Hiroyuki Yamashita
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Patent number: 4789745Abstract: The present invention provides novel .omega.-(3-pyridynl) oxa-, thia-, and aza- alkanoic acids and esters thereof, which are useful as thromboxane A.sub.2 (TXA.sub.2) inhibitors and as such represent potent pharmacological agents.Type: GrantFiled: October 16, 1987Date of Patent: December 6, 1988Assignee: The Upjohn CompanyInventor: Chiu-Hong Lin
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Patent number: 4772683Abstract: Disclosed herein is a novel process using novel silyl enol ether intermediates of the formula ##STR1## to generate novel azetidione thiolester intermediates of the formula ##STR2## which can be used to form 1-.beta.-alkyl carbapenem antibiotics. It has now been discovered that if the R.sup.4 group is selected from a small group of moieties having the formula: ##STR3## an increased .beta.-yield of up to approximately 100% can be obtained.Type: GrantFiled: February 24, 1986Date of Patent: September 20, 1988Assignee: Bristol-Myers CompanyInventors: Alain Martel, Jean-Paul Daris, Jacques Corbeil
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Patent number: 4764613Abstract: The invention relates to the novel 2,6-bis(chloromethyloxy-carbonyloxymethyl)pyridine of the formula (I) ##STR1## as well as a process for the preparation of this compound, which is a useful intermediate in the preparation of the anti-atherosclerotic 2,6-bis(hydroxymethyl)pyridine bis(N-methylcarbamate) (pyridinolcarbamate) and other drugs.According to the invention, the compound of the formula (I) is prepared by reacting 2,6-bis(hydroxymethyl)pyridine of the formula (II) ##STR2## with chloromethyl chloroformate of the formula (III) ##STR3## in a polar-aprotic, water-immiscible organic solvent, in the presence of a basic substance between about -30.degree. C. and +10.degree. C.Type: GrantFiled: August 24, 1987Date of Patent: August 16, 1988Assignee: Richter Gedeon Vegyeszeti Gyar Rt.Inventors: Jozsef Toth, Mate Kovatsits, Laszlo Csutoras, Gabor Szabo, Sandor Gorog, Ferenc Trischler, Sandor Holly, Erzsebet Francsics, Bela Losonczi, Gabor Havasi
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Patent number: 4758573Abstract: Compounds of the general formula ##STR1## and pharmaceutically acceptable salts thereof have antithrombotic activity. Het represents 1-[1H-imidazolyl], 1-N-morpholinyl or pyridyl. A representative compound is 6-[2-(1H-Imidazol-1-yl)-1-yl-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]he xanoic acid.Type: GrantFiled: February 3, 1986Date of Patent: July 19, 1988Assignee: G. D. Searle & Co.Inventors: Paul W. Manley, Lai M. Fook
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Patent number: 4742068Abstract: Dihydropyridine compounds having 1,4,4-trisubstitution of the following formula (I): ##STR1## wherein R is one of --COR.sup.3, R.sup.3 being a group such as phenyl or benzyl; R.sup.4 where R.sup.4 is a heterocycle; --(CH.sub.2).sub.n NR.sup.5 R.sup.6, with R.sup.5 and R.sup.6 being alkyl or joined to define a ring; or --(CH.sub.2).sub.n COOR.sup.7, with R.sup.7 being alkyl or benzyl.R.sup.1 and R.sup.2 are alkyl, phenyl or substituted phenyl.The compounds are useful for the treatment of hypertension in mammals, e.g., in humans.Type: GrantFiled: June 9, 1986Date of Patent: May 3, 1988Assignee: McNeilab, Inc.Inventor: Michael J. Kukla
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Patent number: 4732901Abstract: Compounds of formula (I): ##STR1## in which R.sub.1 is hydrogen or C.sub.1-6 alkyl;R.sub.2 is hydrogen or a group --CO.sub.2 R.sub.3 where R.sub.3 is hydrogen or C.sub.1-6 alkyl;n is an integer of from 2 to 12;X represents a double or triple bond, and each of A and B represents hydrogen when X is a double bond, or both A and B are absent when X is a triple bond; and ##STR2## represents an aromatic heterocyclic ring, are disclosed as inhibitors of 5-lipoxygenase.Type: GrantFiled: February 27, 1986Date of Patent: March 22, 1988Assignee: Beecham Group p.l.c.Inventor: Derek R. Buckle
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Patent number: 4723017Abstract: 3-Hydroxy-3-(2-methyl-5-pyridyl)-propionic acid alkyl esters which, as intermediate products that can be industrially produced in a simple manner, can be used for the production of 2-methylpyridine-5-propionic acid alkyl ester.Type: GrantFiled: December 24, 1986Date of Patent: February 2, 1988Assignee: Lonza Ltd.Inventor: James I. Grayson
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Patent number: 4707549Abstract: Esters of optically active 2-arylalkanoic acids I ##STR1## where Ar is an isocyclic or heterocyclic aryl radical and R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 -alkyl, are prepared by subjecting an optically active ester II ##STR2## where X is Cl, Br or --O--SO.sub.2 --Y and Y is Cl or a hydrocarbon radical, to a Friedel-Crafts reaction with an aromatic compound ArH (III).Type: GrantFiled: February 4, 1985Date of Patent: November 17, 1987Assignee: BASF AktiengesellschaftInventors: Gerhard Fritz, Manfred Eggersdorfer, Hardo Siegel
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Patent number: 4691020Abstract: Optically active carboxylic acids ##STR1## where R.sup.1 is an organic radical which is linked to the asymmetric C' atom via a carbon atom and R.sup.2 is one of the radicals R.sup.1 (but not the same radical), halogen or an organic radical which is bonded to the asymmetric C' atom via an oxygen atom, are prepared by reacting a ketene II ##STR2## with an alcohol in a homogeneous liquid phase in the presence of a tertiary amine III and then converting the resulting ester into the acid, using an optically active alcohol IV.Type: GrantFiled: July 23, 1984Date of Patent: September 1, 1987Assignee: BASF AktiengesellschaftInventors: Christoph Ruechardt, Joachim Jaehme, Ulrich Salz
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Patent number: 4687856Abstract: 3-Hydroxy-3-(2-methyl-5-pyridyl)-propionic acid alkyl esters which, as intermediate products that can be industrially produced in a simple manner, can be used for the production of 2-methylpyridine-5-propionic acid alkyl ester.Type: GrantFiled: June 4, 1986Date of Patent: August 18, 1987Assignee: Lonza Ltd.Inventor: James I. Grayson
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Patent number: 4650890Abstract: 7-Substituted lower alkyl hept-6-enoates and 4-hydroxy-tetrahydropyran-2-ones bearing 6-olefinic substituents (E), (Z), ethyl erythro-3,5-dihydroxy-7-phenyl-hept-6-enates are prepared by a multi-step process involving lower alkyl 3,5-dihydroxy-hept-6-enates. The final products are useful as anti hypercholesteremic agents.Type: GrantFiled: July 26, 1985Date of Patent: March 17, 1987Assignee: Sandoz Corp.Inventors: Charles F. Jewell, Jr., James R. Wareing
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Patent number: 4612386Abstract: Carboxylic acid esters are produced by the reaction of a carboxylic acid halide with a carbonate ester in the presence of an initiator. The reaction of a dicarboxylic acid dihalide and a bis(alkyl carbonate) ester produces a polymeric polyester.Type: GrantFiled: December 17, 1981Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4602002Abstract: Compounds of the formula: ##STR1## wherein R.sup.2 is --(CH.sub.2).sub.k --X--(CH.sub.2).sub.j --NHR.sup.3 ; wherein k is 0 to 3, j is 1 or 2; X is F or OH; and, R.sup.3 is hydrogen; loweralkyl or loweraralkyl which may be substituted by hydroxy, carboxy, carbamoyl, or carbalkoxy; or, acyl; and, a pharmaceutically acceptable salt thereof; are inhibitors of angiotensin I converting enzyme useful as antihypertensive agents.Type: GrantFiled: February 7, 1983Date of Patent: July 22, 1986Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, Mu T. Wu
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Patent number: 4590195Abstract: 1,4-Dihydropyridine derivatives of the formula: ##STR1## wherein R is aryl or heteroaryl; R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.4 alkyl or 2-methoxyethyl; n is 2, 3 or 4; R.sup.3 is H, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4 alkyl) or CH.sub.2 CN; and R.sup.4 is a group of the formula COR.sup.5, CSR.sup.5, C(.dbd.NR.sup.6)R.sup.7 or SO.sub.2 R.sup.5, wherein R.sup.5 is C.sub.1 -C.sub.4 alkyl, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), NH(C.sub.3 -C.sub.6 cycloalkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, NHCH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4 alkyl), NHCH.sub.2 CONH.sub.2, NHCH.sub.2 CO.sub.2 H, NH(CH.sub.2).sub.2 NH.sub.2, NHNH.sub.2, NHNRCO.sub.2 (C.sub.1 -C.sub.4 alkyl), NH-aryl, NHCO-aryl or a heterocyclic, NH-heterocyclic or NHCO-heterocyclic group, or when R.sup.4 is C(.dbd.O)R.sup.5, R.sup.5 may be H or CF.sub.3 ; R.sup.6 is H, CN, CO.sub.2 (C.sub.1 -C.sub.4 alkyl), CO(C.sub.1 -C.sub.4 alkyl), SO.sub.2 (C.sub.1 -C.sub.4 alkyl), SO.sub.2 -aryl, SO.sub.2 NH.sub.2, SO.sub.2 N(C.sub.1 -C.Type: GrantFiled: March 5, 1984Date of Patent: May 20, 1986Assignee: Pfizer Inc.Inventors: David Alker, Peter E. Cross, Simon F. Campbell
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Patent number: 4579862Abstract: Compounds of the general formula ##STR1## and pharmaceutically acceptable salts thereof have antithrombotic activity. Het represents 1-[1H-imidazolyl], 1-N-morpholinyl or pyridyl. A representative compound is 6-[2-(1H-Imidazol-1-yl)-1-yl-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]he xanoic acid.Type: GrantFiled: July 5, 1983Date of Patent: April 1, 1986Assignee: G. D. Searle & Co.Inventors: Paul W. Manley, Lai M. Fook
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Patent number: 4579850Abstract: Compounds having the formula ##STR1## in which R is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.1 is halo-(C.sub.2 -C.sub.5 alkyl); halo-(C.sub.2 -C.sub.5 alkenyl) or halo-(1-methyl-cyclopropyl); and n is an integer from 1 to 3, and their amine salts are insect repellents.Type: GrantFiled: February 25, 1985Date of Patent: April 1, 1986Assignee: Stauffer Chemical CompanyInventor: Rayman Y. Wong
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Patent number: 4560763Abstract: A base precursor for heat-developable photosensitive material is disclosed. The precursor is comprised of a compound represented by general formula (I) or (II):(R--C.tbd.C--CO.sub.2 H).sub.x.B (I)R--C.tbd.C--CO.sub.2 H).sub.2.B.sub.y (II)The substituents within the general formulae are defined within the specification. The use of this novel base precursor makes it possible to obtain a material which is very stable at normal temperatures and which smoothly decomposes under heating at 80.degree. C. or higher in order to release a basic constituent.Type: GrantFiled: March 30, 1984Date of Patent: December 24, 1985Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Hiroyuki Hirai
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Patent number: 4551460Abstract: Pyrido[2,1-b]quinazoline derivatives of the formulas ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as hereinafter set forth, are described. The compounds of formulas I and II are useful as agents for the treatment of allergic conditions as well as for the treatment of vascular disorders involving thrombosis.Type: GrantFiled: March 2, 1983Date of Patent: November 5, 1985Assignee: Hoffmann-La Roche Inc.Inventor: Jefferson W. Tilley
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Patent number: 4542220Abstract: The invention relates to a process for the preparation of derivatives of dichloroacetic acid esters, by reaction of a glyoxylic acid ester having the general formula R.sub.1 --CO--COOR.sub.2, wherein R.sub.1 represents an optionally substituted aryl or heteroaryl group and R.sub.2 an alkyl, cycloalkyl or aryl group, with phosphoruspentachloride in the presence of a dispersant suitable for distributing the phosphoruspentachloride.Type: GrantFiled: September 15, 1982Date of Patent: September 17, 1985Assignee: Stamicarbon B.V., Licensing Subsidiary of DSMInventors: Antonius Corvers, Joannes M. C. A. Mulders
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Patent number: 4535084Abstract: A series of 4-(2-hydroxyethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable acid addition salts, having immunoregulatory activity are disclosed. Preferred compounds include 4-(2-hydroxyethylthiomethyl)pyridine itself, as well as 4-(2-hydroxy-1-propylthiomethyl)pyridine, 4-(3-hydroxy-2-butylthiomethyl)pyridine, the acetate esters corresponding to the above compounds, and 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine.Type: GrantFiled: March 18, 1983Date of Patent: August 13, 1985Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert
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Patent number: 4529721Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.Type: GrantFiled: September 21, 1983Date of Patent: July 16, 1985Assignee: Shionogi & Co., Ltd.Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
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Patent number: 4500535Abstract: A series of 4-(2-carboxymethylthiomethyl)pyridines and related compounds, and their pharmaceutically acceptable salts, are disclosed as having immunoregulatory activity. Preferred compounds include 4-(2-carboxymethylthiomethyl)pyridine [alternatively named 2-(4-picolylthio)acetic acid] and (C.sub.1 -C.sub.4)alkyl esters thereof, and 4-(1-formylmethylthiomethyl)-pyridine [alternatively named 2-(4-picolylthio)acetaldehyde] and bis(C.sub.1 -C.sub.4)alkyl or cyclic acetals thereof. These acids, esters, aldehydes and acetals also have utility as intermediates in the synthesis of the corresponding 4-(2-hydroxyethylthiomethyl)pyridines.Type: GrantFiled: March 7, 1983Date of Patent: February 19, 1985Assignee: Pfizer Inc.Inventors: Joseph G. Lombardino, Charles A. Harbert