EP1194419A1 - Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique - Google Patents

Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique

Info

Publication number
EP1194419A1
EP1194419A1 EP00940367A EP00940367A EP1194419A1 EP 1194419 A1 EP1194419 A1 EP 1194419A1 EP 00940367 A EP00940367 A EP 00940367A EP 00940367 A EP00940367 A EP 00940367A EP 1194419 A1 EP1194419 A1 EP 1194419A1
Authority
EP
European Patent Office
Prior art keywords
halogen
optionally
carbon atoms
substituted
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP00940367A
Other languages
German (de)
English (en)
Inventor
Heinz-Jürgen Wroblowsky
Otto Schallner
Hans-Georg Schwarz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1194419A1 publication Critical patent/EP1194419A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/04—1,2,3-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

  • the invention relates to a new process for the preparation of 2-heterocyclyl-methyl-benzoic acid derivatives, which as intermediates for the preparation of
  • Active ingredients for pharmaceutical and agricultural applications can be used.
  • n the numbers 0, 1, 2 or 3
  • X stands for nitro, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and Z represents heterocyclyl bound via N (nitrogen),
  • n and X have the meaning given above,
  • the 2-heterocyclylmethyl-benzoic acid derivatives of the general formula (1) can be obtained selectively in good yields and in high purity by the process according to the invention, although according to the prior art given above, the formation of N-heterocyclyl to a large extent as a side reaction -2-hydroxymethyl-benzamide derivatives was expected.
  • the process according to the invention represents a technically well practicable route to 2-heterocyclylmethyl-benzoic acid derivatives based on phthalides which are easily accessible by known methods.
  • the desired benzoic acid derivatives are immediately obtained when the ring is opened. i
  • n is preferably the number 0, 1, 2 or 3.
  • X preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen, each optionally substituted by halogen, Cj -C ⁇ alkoxy, C] -C4-alkylthio, C] -C4-alkylsulfinyl or -C-C4-alkylsulfonyl-substituted alkyl, alkoxy,
  • Z preferably represents one of the heterocyclic group
  • Q oxygen or sulfur
  • Rl for hydrogen, hydroxyl, mercapto, cyano, halogen, for alkyl optionally substituted by cyano, halogen, C 1 -C 4 alkoxy, C] -C 4 alkylthio, C 1 -C 4 alkylsulfinyl or C 1 -C 4 alkylsulfonyl , Alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms in the alkyl groups, for each alkylamino or dialkylamino optionally substituted by halogen, each having up to 6 carbon atoms in the alkyl groups, each optionally using halogen Substituted alkenyl, alkynyl, alkenyloxy, alkenylthio or alkenylamino, each having up to 6 carbon atoms in the alkenyl or alkyny
  • Cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl part, or for each optionally by Halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or - in the event that two adjacent radicals R 1 and R 1 are attached to a double bond are - together with the adjacent radical R 1 also represents a benzo group, and
  • R ⁇ for hydrogen, hydroxy, A ino, alkylidene amino with up to 4 carbon atoms, for each optionally substituted by cyano, halogen or C ] -C4-alkoxy alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino each with up to 6 carbon atoms in the alkyl groups, each for alkenyl, alkynyl or alkenyloxy optionally substituted by halogen, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkylalkyl or cycloalkylamino, each optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted in each case by halogen, C1-C4-alkyl or Cj
  • n particularly preferably represents the numbers 0, 1 or 2.
  • X particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl,
  • Q represents oxygen or sulfur
  • R ' for hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i -Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i- propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy
  • Benzo grouping stands, and R ⁇ for hydrogen, hydroxyl, amino, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy or i-propoxy, methylamino, ethylamino or dimethylamino, for each optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, ethynyl, propynyl or propenyloxy, for each optionally substituted by fluorine and / or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl , Cyclobutylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, or for each optionally by fluorine, chlorine
  • R 1 and R 2 are defined as in the particularly preferred definitions of Z.
  • R 1 and R 2 are defined as in the most particularly preferred definitions of Z.
  • the phthalides of the general formula (II) required as starting materials in the process according to the invention are known and / or can be prepared by processes known per se (cf. Heterocycles 31 (1990), 1261-1270; Synth. Commun. 20 (1990), 2641 -2652; J. Org. Chem. 57 (1992), 2029-2033).
  • the alkali metal and alkaline earth metal salts such as the lithium, sodium, rubidium, cesium, magnesium, calcium and barium salts, very particularly preferably the sodium and potassium salts of these compounds become.
  • Formula (I) is carried out using an aprotic polar diluent.
  • aprotic polar diluent include in particular ethers such as diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone, butanone, methyl isopropyl ketone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide,
  • Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, and sulfones such as tetramethylene sulfone (sulfolane).
  • Ketones such as methyl isobutyl ketone
  • amides such as N, N-dimethyl formamide and N, N-dimethyl acetamide, are very particularly preferred as diluents.
  • the process according to the invention for the preparation of the compounds of the general formula (I) is optionally carried out using a basic reaction auxiliary.
  • the usual inorganic or organic bases or acid acceptors are generally suitable. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, Sodium or potassium methoxide, ethanolate, n or i-propanolate, n, i, s or t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl diisopropylamine, N, N-
  • Alkali metal and alkaline earth metal hydrides, hydroxides and alkanolates such as lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, - ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate are very particularly preferred as basic reaction auxiliaries.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 180 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar.
  • 1 mole of phthalide of the general formula (II) is generally between 0.8 and 1.2 mole, preferably between 0.95 and 1.05 mole, of nitrogen heterocycle of the general formula (III) or a salt of this one.
  • reaction components are mixed at room temperature or with cooling and the reaction mixture is then
  • the workup can be carried out according to customary methods.
  • the mixture is concentrated under reduced pressure, the residue is washed with an organic solvent which is practically immiscible with water, then in
  • the 2-heterocyclylmethylbenzoic acid derivatives of the general formula (I) to be prepared by the process according to the invention can be used as intermediates for

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé pour produire des dérivés d'acide 2-hétérocyclylméthylbenzoïque de formule générale (I), avec un bon rendement et un pureté élevée. L'invention est caractérisée en ce que les phtalides de formule générale (II) réagissent avec des composés hétérocycliques d'azote de formule générale (III): H-Z, dans laquelle Z représente un composé hétérocyclique lié à l'azote, ou avec des sels métalliques de composés hétérocycliques d'azote de formule générale (II), en présence d'un diluant polaire aprotique et éventuellement en présence d'un auxiliaire de réaction basique.
EP00940367A 1999-06-26 2000-06-13 Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique Withdrawn EP1194419A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19929348A DE19929348A1 (de) 1999-06-26 1999-06-26 Verfahren zur Herstellung von 2-Heterocyclylmethyl-benzoesäurederivaten
DE19929348 1999-06-26
PCT/EP2000/005412 WO2001000595A1 (fr) 1999-06-26 2000-06-13 Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique

Publications (1)

Publication Number Publication Date
EP1194419A1 true EP1194419A1 (fr) 2002-04-10

Family

ID=7912666

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00940367A Withdrawn EP1194419A1 (fr) 1999-06-26 2000-06-13 Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique

Country Status (10)

Country Link
EP (1) EP1194419A1 (fr)
JP (1) JP2003503396A (fr)
CN (1) CN1358176A (fr)
AU (1) AU5532500A (fr)
BR (1) BR0012451A (fr)
DE (1) DE19929348A1 (fr)
HK (1) HK1047932A1 (fr)
IL (1) IL146662A0 (fr)
MX (1) MXPA01013263A (fr)
WO (1) WO2001000595A1 (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6914082B2 (en) 2001-12-14 2005-07-05 Conocophillips Company Slurry bubble reactor operated in well-mixed gas flow regime
US7230035B2 (en) 2002-12-30 2007-06-12 Conocophillips Company Catalysts for the conversion of methane to synthesis gas
DE102006024024A1 (de) 2006-05-23 2007-11-29 Bayer Healthcare Aktiengesellschaft Substituierte Arylimidazolone und -triazolone sowie ihre Verwendung
WO2008106128A2 (fr) 2007-02-26 2008-09-04 Vitae Pharmaceuticals, Inc. Inhibiteurs d'urée et de carbamate de 11b-hydroxystéroïde déshydrogénase 1 cycliques
JP5470557B2 (ja) 2007-07-26 2014-04-16 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の阻害剤の合成
JP5490014B2 (ja) 2007-12-11 2014-05-14 ヴァイティー ファーマシューティカルズ，インコーポレイテッド １１β−ヒドロキシステロイドデヒドロゲナーゼ１型の環状尿素阻害剤
TW200934490A (en) 2008-01-07 2009-08-16 Vitae Pharmaceuticals Inc Lactam inhibitors of 11 &abgr;-hydroxysteroid dehydrogenase 1
US8592409B2 (en) 2008-01-24 2013-11-26 Vitae Pharmaceuticals, Inc. Cyclic carbazate and semicarbazide inhibitors of 11β-hydroxysteroid dehydrogenase 1
WO2009102428A2 (fr) 2008-02-11 2009-08-20 Vitae Pharmaceuticals, Inc. INHIBITEURS 1,3-OXAZEPAN-2-ONE ET 1,3-DIAZEPAN-2-ONE DE LA 11β-HYDROXYSTÉROÏDE DÉSHYDROGÉNASE (TYPE1)
CA2715290A1 (fr) 2008-02-15 2009-08-20 Vitae Pharmaceuticals, Inc. Inhibiteurs de la 11 beta-hydroxysteroide dehydrogenase 1
WO2009134387A1 (fr) 2008-05-01 2009-11-05 Vitae Pharmaceuticals, Inc. Inhibiteurs cycliques de la 11-bêta-hydroxystéroïde déhydrogénase 1
US8138178B2 (en) 2008-05-01 2012-03-20 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
CA2723032A1 (fr) 2008-05-01 2009-11-05 Vitae Pharmaceuticals, Inc. Inhibiteurs cycliques de la 11-beta-hydroxysteroide dehydrogenase 1
US8569292B2 (en) 2008-05-01 2013-10-29 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1
TW201016691A (en) 2008-07-25 2010-05-01 Boehringer Ingelheim Int Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
NZ590495A (en) 2008-07-25 2012-10-26 Vitae Pharmaceuticals Inc Dihydropyridin-phenyl-3-oxazinan-2-ones as inhibitors of 11beta-hydroxysteroid dehydrogenase 1
DE102008060967A1 (de) * 2008-12-06 2010-06-10 Bayer Schering Pharma Aktiengesellschaft Substituierte Phenylsulfonyltriazolone und ihre Verwendung
US8637505B2 (en) 2009-02-04 2014-01-28 Boehringer Ingelheim International Gmbh Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
DE102010001064A1 (de) 2009-03-18 2010-09-23 Bayer Schering Pharma Aktiengesellschaft Substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung
US8680093B2 (en) 2009-04-30 2014-03-25 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
US8927539B2 (en) 2009-06-11 2015-01-06 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
US8883778B2 (en) 2009-07-01 2014-11-11 Vitae Pharmaceuticals, Inc. Cyclic inhibitors of 11 beta-hydroxysteroid dehydrogenase 1
MY169980A (en) 2010-02-27 2019-06-19 Bayer Ip Gmbh Bisaryl-linked aryltriazolones and their use
US8933072B2 (en) 2010-06-16 2015-01-13 Vitae Pharmaceuticals, Inc. Substituted 5-,6- and 7-membered heterocycles, medicaments containing such compounds, and their use
WO2011161128A1 (fr) 2010-06-25 2011-12-29 Boehringer Ingelheim International Gmbh Azaspirohexanones comme inhibiteurs de 11-β-hsd1 pour le traitement de troubles métaboliques
DE102010040187A1 (de) 2010-09-02 2012-03-08 Bayer Schering Pharma Aktiengesellschaft Substituierte N-Phenethyl-triazolonacetamide und ihre Verwendung
DE102010040924A1 (de) 2010-09-16 2012-03-22 Bayer Schering Pharma Aktiengesellschaft Substituierte Phenylacet- und Phenylpropanamide und ihre Verwendung
EA201300522A1 (ru) 2010-11-02 2013-11-29 Бёрингер Ингельхайм Интернациональ Гмбх Фармацевтические комбинации для лечения метаболических нарушений
AU2015342017B2 (en) 2014-11-03 2020-02-06 Bayer Pharma Aktiengesellschaft Hydroxyalkyl-substituted phenyltriazole derivatives and uses thereof
US9988367B2 (en) 2016-05-03 2018-06-05 Bayer Pharma Aktiengesellschaft Amide-substituted pyridinyltriazole derivatives and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19627901A1 (de) * 1996-07-11 1998-01-15 Bayer Ag Substituierte aromatische Carbonylverbindungen und ihre Derivate
DE19921732A1 (de) * 1998-07-24 2000-01-27 Bayer Ag Substituierte Benzoylcyclohexandione

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0100595A1 *

Also Published As

Publication number Publication date
JP2003503396A (ja) 2003-01-28
DE19929348A1 (de) 2000-12-28
HK1047932A1 (zh) 2003-03-14
AU5532500A (en) 2001-01-31
MXPA01013263A (es) 2002-06-21
IL146662A0 (en) 2002-07-25
CN1358176A (zh) 2002-07-10
BR0012451A (pt) 2002-04-02
WO2001000595A1 (fr) 2001-01-04

Similar Documents

Publication Publication Date Title
EP1194419A1 (fr) Procede pour produire des derives d'acide 2-heterocyclylmethylbenzoique
US5051517A (en) Process for the preparation of herbicidally active 3-amino-5-aminocarbonyl-1,2,4-triazoles
EP0758324A1 (fr) Amides aromatiques substitues d'acides thiocarboxyliques et leur utilisation comme herbicides
WO1996018618A1 (fr) Derives de 3-aryl-1,2,4-triazole presentant des proprietes herbicides
DE10005284A1 (de) Verfahren zur Herstellung von 1-Amino-3-aryl-uracilen
EP1172357B1 (fr) Procédé pour la préparation d'esters hydrazinecarboxyliques et produits intermediaires de cet procédé
EP0661277B1 (fr) Procédé et nouveaux intermédiaires pour la préparation de triazolines
EP0708095B1 (fr) Procédé de préparation d'alcoxytriazoles
EP0659746B1 (fr) Procédé pour la préparation de sulfonyaminocarbonyl-triazolinones
EP0703224B1 (fr) Procédé de préparation d'alcoxytriazolinones
EP0757041B1 (fr) Procédé pour la préparation d'aminocarbonyltriazolinones substituées
DE19500439A1 (de) Substituierte aromatische Thiocarbonsäureamide
WO1997033876A1 (fr) Procede de fabrication d'amides aromatiques substitues de l'acide thiocarboxylique
US5688963A (en) Intermediates for the preparation of triazolinones
DE69902886T2 (de) Verfahren zur herstellung von aryloxy- oder alkoxytriazolinonen
DE19504059A1 (de) Verfahren zur Herstellung von substituierten N-Carbamoyl-tetrazolinonen
EP0888312A1 (fr) Procede de fabrication d'amides aromatiques substitues de l'acide thiocarboxylique
EP0398097B1 (fr) Procédé et intermédiaires pour la préparation de dérivés de triazolone
DE60005776T2 (de) Verfahren zur Herstellung von substituierten Triazolinonen
DE10063493A1 (de) Verfahren zur Herstellung von substituierten Arylketonen
US5874586A (en) Process for preparing 1-aryl-4-carbamoyl-tetrazolinones
EP0906270B1 (fr) Procede de preparation d'hydroxyarenes
EP0764642B1 (fr) Procédé pour la préparation de 1-aryl-4-carbamoyl-tétrazolinones
EP0759430A1 (fr) Procédé pour la préparation d'aminotriazolinones
MXPA98007174A (en) Procedure for the obtaining of amidas of tiocarboxilic, aromatic, substitute acids

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20020128

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER CROPSCIENCE AG

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20031231