[go: up one dir, main page]

WO1997030965A1 - PROCEDE D'ELABORATION DE DERIVES D'ACIDE α-ALKOXYPHENYLACETIQUE - Google Patents

PROCEDE D'ELABORATION DE DERIVES D'ACIDE α-ALKOXYPHENYLACETIQUE Download PDF

Info

Publication number
WO1997030965A1
WO1997030965A1 PCT/JP1997/000456 JP9700456W WO9730965A1 WO 1997030965 A1 WO1997030965 A1 WO 1997030965A1 JP 9700456 W JP9700456 W JP 9700456W WO 9730965 A1 WO9730965 A1 WO 9730965A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
compound represented
halogenating agent
represented
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.)
Ceased
Application number
PCT/JP1997/000456
Other languages
English (en)
Japanese (ja)
Inventor
Toshikazu Ohtsuka
Takami Murashi
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Priority to AU17335/97A priority Critical patent/AU1733597A/en
Publication of WO1997030965A1 publication Critical patent/WO1997030965A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers

Definitions

  • the present invention relates to a method for producing an ⁇ -alkoxyphenylacetic acid derivative useful as an agricultural fungicide.
  • the present inventors have conducted intensive studies on a novel method for synthesizing an ⁇ -alkoxyphenylacetic acid derivative, and as a result, have found a method for efficiently producing an ⁇ -alkoxyphenylacetic acid derivative from a -octaphenylphenylacetic acid derivative.
  • the present invention provides a) a formula (2): PT P97 0456
  • X and Y each independently represent a halogen atom, and ⁇ represents an alkoxy or an optionally substituted amino] in the presence of a base.
  • Q represents an optionally substituted aryl, an optionally substituted heterocyclic group or a mono- or di-substituted methyleneamino] or a metal thereof.
  • R 3 represents alkyl, and other symbols have the same meanings as described above].
  • R 1 and R 2 have the same meanings as described above, and V and W each independently represent a chlorine atom or a bromine atom.
  • the carboxylic acid halogenating agent is used in an amount of 1 to 1.5 equivalents based on compound (3).
  • Y is as defined above, is halogenated using a carboxylic acid halogenating agent and an alkyl side chain halogenating agent, and then a compound represented by the formula (8):
  • the method of the present invention it is possible to derive a target compound from a commercially available compound in a short process as compared with a method for producing a monoalkoxyphenyl carboxylic acid derivative which is useful as a conventional agricultural fungicide.
  • the safety of all reactions used is high, and It is suitable for industrial production, because it can lead to the target at low cost.
  • a carboxylic acid halogenating agent is a reagent that converts a carboxylic acid into an acid halide, and examples thereof include thionyl halide and phosphorus trihalide. In particular, thionyl chloride is preferred.
  • the alkyl side chain halogenating agent is a reagent for halogenating the methylene at the 2-position or the methyl at the o-position of phenylacetic acid, and is preferably sulfonyl nodogenate, particularly preferably sulfuryl chloride.
  • halogen atom represented by X and Y examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Of these, a chlorine atom and a bromine atom are preferred.
  • alkoxy represented by Z examples include alkoxy having 1 to 8 carbon atoms, preferably alkoxy having 1 to 4 carbon atoms, specifically, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec butoxy, tert-alkoxy. Butoxy, etc. can be obtained. Of these, methoxy is preferred.
  • the optionally substituted amino represented by Z is preferably represented by the formula: NR 1 R 2 (wherein R 1 and R 2 are the same or different and are a hydrogen atom or an alkyl).
  • the alkyl represented by RR 2, 1 ⁇ 8 carbon atoms preferably alkyl having 1 to 4 carbon atoms, such as methyl, Echiru, propyl, i Sopu port pills, heptyl, Lee Sopuchiru, sec-heptyl, tert-butyl And so on.
  • R 1 and R 2 is a hydrogen atom and the other is methyl.
  • the optionally substituted aryl represented by Q is, for example, an aryl having 6 to 14 carbon atoms, specifically, phenyl, naphthyl (eg, naphthyl, / 3—naphthyl) Etc.) These are replaced.
  • the substituent When the substituent is lower, it is lower (C 1-8, preferably C 1-6, more preferably C 1-4); ) Alkyl (eg, methyl, ethyl, propyl, butyl, etc.), lower alkenyl (eg, vinyl, aryl, crotyl, etc.), lower alkynyl (eg, ethynyl, propargyl, butynyl, etc.), cycloalkyl (eg, cyclopropyl, cyclopentyl) , Cyclohexyl, etc.), lower alkoxy lower alkyl (eg, methoxymethyl, ethoxymethyl, 2-methoxyethyl, etc.), cycloalkenyl (eg, cyclopentenyl, cyclohexenyl, etc.), lower alkylcarbonyl (eg, , Acetyl, propionyl, isobutyryl, etc.), lower alkyls
  • substituents may be located at any substitutable position on the ring.
  • the total number of substitution groups is from 1 to 5, preferably 1 to 4, more preferably 1 to There are three and these may be the same or different.
  • Examples of the optionally substituted heterocyclic group represented by Q include 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur as ring-constituting atoms. Membered heterocyclic groups. These heterocyclic groups may form a condensed ring with another hetero ring or a benzene ring.
  • pyridyl which may be substituted (eg, pyridin-1-yl, pyridin-13-yl, etc.), pyrimidinyl (eg, pyrimidine-14-yl, Pyrimidine-1-yl, quinolyl (eg, quinolin-4-yl), quinazolinyl (eg, quinazolin-14-yl, etc.), benzothiazolyl (eg, benzothiazol-2-yl) ), Birazolyl
  • examples of the substituent include the groups exemplified as the aryl substituent represented by the above Q. Of these, a halogen atom, haloalkyl, alkoxy, alkoxycarbonyl or formyl is preferable, and a chlorine atom or trifluoroethyl is more preferable. These substituents may be located at any substitutable position on the ring. The number of the substituents is 1 to 5, preferably 1 to 4, and more preferably 1 to 3, and they may be the same or different.
  • the mono-substituted or di-substituted methylamine amino represented by Q is, for example, of the formula
  • R ', R 5 are the same or different and each represents a hydrogen atom, an alkyl but it may also be substituted, Ashiru, alkylthio, alkylsulfinyl, alkyl sulfonyl, optionally substituted ⁇ Mi also be Bruno, a cycloalkyl, substituted Is Forming a polycyclic was good monocyclic or even contain heteroatoms bonded force or R 4 and R 5 showing the heterocyclic group to be optionally be also good ⁇ Li Lumpur or substituted optionally To indicate that you are doing this).
  • the substituted alkyl exemplified as the substituent of the optionally substituted aryl represented by Q can be used. And the same groups as the alkyl which may be used. Of these, methyl and ethyl are preferred.
  • R ⁇ " as the Ashiru represented by R 5, for example, alkylcarbonyl, as the.
  • the alkylcarbonyl etc. ⁇ re Rukarubo two Le can be mentioned, for example, 1 to 6 carbon atoms, preferably alkyl having 1 to 4 carbon atoms
  • Examples of the alkyl carbonyl include acetyl, trifluoroacetyl, propionyl, and butyryl, etc.
  • the arylcarbonyl include, for example, aryl having 6 to 14 carbon atoms.
  • Arylcarbonyl specifically, benzoyl, naphthoyl and the like.
  • Examples of the alkylthio represented by R 4 and R 5 include the same groups as the alkylthio exemplified as the substituent of the optionally substituted aryl represented by Q.
  • R 4 is as a alkylsulfides alkylsulfonyl represented by R [delta], for example 1 to 8 carbon atoms, preferably an alkyl sulfides alkylsulfonyl of 1 to 4 carbon atoms, specifically, Mechirusurufi sulfonyl, E chill sulfinyl, pro Pyrsulfinyl and the like.
  • the alkylsulfonyl represented by R 4 and R 5 includes, for example, alkylsulfonyl having 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, specifically, methylsulfonyl, ethylsulfonyl, propylsulfonyl and the like.
  • alkylsulfonyl having 1 to 8 carbon atoms preferably 1 to 4 carbon atoms, specifically, methylsulfonyl, ethylsulfonyl, propylsulfonyl and the like.
  • Examples of the optionally substituted amino represented by R 4 > R 5 include, for example, the substituents of the optionally substituted aryl shown by the aforementioned Q Examples include the same groups as those for amino which may be substituted.
  • cycloalkyl represented by R 4 and R 5 cycloalkyl having 3 to 7 carbon atoms, preferably 5 to 6 carbon atoms, specifically, cyclopropyl, cyclopropyl, cyclopentyl and cycloalkyl hexyl, heptyl and the like force 3 ', such as to a consequent Russia.
  • Examples of the aryl of the optionally substituted aryl represented by R 4 and R S include the groups exemplified as the optionally substituted aryl represented by the above Q Similar groups are used. Of these, phenyl is preferred. The aryl may be substituted at any possible position of these ring groups, and the number of substituents is 1 to 3. Specific examples of the substituent include a halogen atom, an optionally substituted alkyl, an optionally substituted hydroxyl group, an alkylthio, an optionally substituted amino, nitro, phenyl, cyano and the like. Is lost.
  • Examples of good aminos include the same groups as the groups exemplified as the substituents on the optionally substituted aryl represented by Q.
  • Examples of the optionally substituted heterocyclic group represented by R 4 and R 5 include, for example, a 5- to 7-membered member having 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur as ring-constituting atoms.
  • Heterocyclic groups include, for example, pyridyl, pyridazinyl, pyrazolyl, pyrimidinyl, furyl, chenyl, oxazolyl, isoxazolyl, benzothiazolyl, quinolyl, quinazolinyl, vilazinyl, morpholino, piperazinyl and the like.
  • R 4 and R 5 are bonded to a single ring or multi-ring may contain hetero atom is formed is a R 4 and R 5 are those formed with the carbon atoms to which they are attached heteroatom (e.g. , Oxygen, nitrogen, sulfur, etc.), which may form a condensed ring with another ring.
  • heteroatom e.g. , Oxygen, nitrogen, sulfur, etc.
  • Specific examples of the ring include cyclopentane, cyclohexane, indane, 1,2,3.4-tetrahydrodronaphthalene, 5,6,7,8 tetrahydroquinoline, 4, 5, 6 7 — Tetrahydrobenzo [b] franc and the like. These rings may have a divalent bond at any possible position.
  • the alkyl represented by R 3 is an alkyl having 18 carbon atoms, preferably an alkyl having 14 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl, tert-butyl and the like. Are mentioned. Of these, methyl is preferred.
  • compound (6) or a metal salt thereof is condensed with compound (2) in the presence of a base to obtain compound (11).
  • Examples of the metal salt of compound (6) include alkali metal salts (such as sodium salt and potassium salt).
  • Compound (6) or its metal salt is used in 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to compound (2).
  • the base examples include an organic base (such as sodium methoxide, sodium ethoxide, and potassium t-butoxide), and an inorganic base (such as sodium hydroxide and potassium hydroxide).
  • organic base such as sodium methoxide, sodium ethoxide, and potassium t-butoxide
  • inorganic base such as sodium hydroxide and potassium hydroxide.
  • Lithium, potassium carbonate, sodium hydride, potassium hydride and the like which are added to the compound (2) in an amount of from 0.5 to 10, 4 to 4 and preferably from 1 to 4. Use 3 equivalents.
  • reaction solvent examples include aromatic hydrocarbons (toluene, etc.); ethers (tetrahydrofuran, etc.); ditylformamide, dimethylsulfoxide or water. These may be used alone or as a mixture. be able to. However, when water is used, a phase transfer catalyst may be used.
  • the reaction temperature is a suitable temperature from 0 ° C to the reflux temperature of the solvent, preferably 0 to 80 ° C, and the reaction time is 1 to 48 hours.
  • the obtained compound (11) is used as a crude product in the form of the reaction solution, or is separated and purified by a conventional method (eg, chromatography, recrystallization, etc.), and then a metal salt of alcohol is obtained.
  • a conventional method eg, chromatography, recrystallization, etc.
  • metal salt of alcohol for example, sodium methoxide, potassium isopropoxide, potassium monobutoxide or the like may be used directly, or alcohols (eg, methanol , Ethanol, etc.) Metal salts (eg, sodium, potassium, etc.) or metal hydrides (eg, sodium hydride, potassium hydride, etc.) to form metal salts of alcohols Used. In either case, the metal salt of alcohol is used in an amount of 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to compound (11). As the metal salt of alcohol, sodium methoxide is preferable.
  • Reaction solvents include alcohols (eg, methanol, ethanol, isopropanol, butanol); dimethylformamide; dimethyl sulfoxide; aromatic hydrocarbons (eg, toluene) And the like, and these can be used alone or as a mixture.
  • alcohols eg, methanol, ethanol, isopropanol, butanol
  • dimethylformamide e.g., dimethyl sulfoxide
  • aromatic hydrocarbons eg, toluene
  • the reaction temperature is an appropriate temperature from 0 ° C to the reflux temperature of the solvent, and the reaction time is 1 to 48 hours.
  • the obtained monoalkoxyphenylacetic acid derivative (1) can be used as a bactericide by a known method.
  • the compound (2) used as a raw material in the above reaction formula 1 can be produced by the reactions of the following reaction formulas 2 to 5.
  • a compound in which X and Y are the same that is, a compound represented by the formula (2a) is obtained by halogenating the compound (3) with a carboxylic acid halogenating agent and an alkyl side chain halogenating agent, Then, it can be produced by reacting with compound (8).
  • carboxylic acid halogenating agent examples include thionyl halide (eg, chloride) Thionyl, thionyl bromide, etc.); phosphorus trihalide (eg, phosphorus trichloride, phosphorus tribromide, etc.) and the like, and 1 to 10 equivalents, preferably 3 to 10 equivalents to compound (3). Use 10 equivalents.
  • alkyl side chain halogenating agent examples include sulfuryl chloride; halogen (eg, chlorine, bromine, etc.), and these are used in an amount of 1 to 10 equivalents based on compound (3).
  • reaction solvent for example, thionyl halide and the like have a function as a solvent, but generally ethers (eg, tetrahydrofuran); halogenated hydrocarbons (eg, 1,2-dichloroethane) It is better to use.
  • the reaction temperature is an appropriate temperature from room temperature to the reflux temperature of the solvent, and the reaction time is 1 to 48 hours.
  • Z when Z is alkoxy, it can be subsequently amidated to give an amino which may be substituted with Z. Amidation can be carried out in the same manner as described in Reaction Scheme 4 below.
  • reaction solvent use is made of aromatic hydrocarbons (eg, toluene); ethers (eg, tetrahydrofuran); and halogenated hydrocarbons (eg, methylene chloride, 1,2-dichloroethane).
  • aromatic hydrocarbons eg, toluene
  • ethers eg, tetrahydrofuran
  • halogenated hydrocarbons eg, methylene chloride, 1,2-dichloroethane
  • Compound (8) is used in 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to compound (3).
  • the reaction temperature is a suitable temperature from 0 ° C to the reflux temperature of the solvent, preferably 0 ° C to room temperature, and the reaction time is 1 to 24 hours.
  • the obtained compound (2a) can be separated and purified by a known means (eg, chromatography, recrystallization, etc.).
  • R represents alkyl, and X is as defined above
  • the compound in which X and Y are the same and Z is alkoxy that is, the compound represented by the formula (2b), is produced by halogenating the compound (5).
  • the compound represented by the formula (2b) is produced by halogenating the compound (5).
  • alkyl having 1 to 8 carbon atoms preferably alkyl having 1 to 4 carbon atoms, specifically, methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec-butyl Tert-butyl and the like.
  • halogenating agent examples include N-nitrosuccinimide (eg, N-chlorosuccinimide, N-bromosuccinimide); nodogen (eg, chlorine, bromine, etc.); 1) to 5 equivalents, preferably 1 to 3 equivalents to 5).
  • Benzoyl peroxide or 2,2′-azobis may be used as a reaction initiator in an amount of 0.05 to 0.2 equivalents to compound (5), May be irradiated.
  • aromatic hydrocarbons such as benzene
  • halogenated hydrocarbons such as carbon tetrachloride
  • the reaction temperature is an appropriate temperature from 0 ° C to the reflux temperature of the solvent.
  • the duration of the reaction is between 1 and 24 hours.
  • the obtained compound (2b) can be separated and purified by a known means (eg, chromatography, crystal, etc.).
  • the compound (5) used as a raw material in the reaction of the reaction formula 3 is obtained by reacting a commercially available compound (3) with the presence of a base F, an alkylating agent (eg, alkyl halide, dialkyl sulfate, etc.). It can be manufactured by the following.
  • the alkyl halide include methyl chloride, methyl bromide, methyl iodide, butyl bromide, chloro iodide, 1-propane propane, 2-iodopropane, and 1-butane, and dialkyl sulfate.
  • Examples thereof include dimethyl sulfate and getyl sulfate, which are used in an amount of 1 to 5 equivalents, preferably 1 to 2 equivalents, based on the compound (3).
  • bases examples include: organic bases (eg, sodium methoxide, sodium ethoxide, potassium t-butoxide, etc.): inorganic bases (eg, sodium hydroxide, potassium hydroxide) Lithium, sodium hydride, potassium hydride, etc.) are used, and they are used in 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to compound (3).
  • organic bases eg, sodium methoxide, sodium ethoxide, potassium t-butoxide, etc.
  • inorganic bases eg, sodium hydroxide, potassium hydroxide
  • ethers such as getyl ether and tetrahydrofuran; N.N-dimethylformamide; dimethylsulfoxide; toluene, and the like can be used.
  • the reaction temperature is an appropriate temperature from 120 to the reflux temperature of the solvent, preferably 0 to 50 ° C, and the reaction time is 0.5 to 48 ⁇ , preferably 0.5 to 10 hours. is there.
  • the obtained compound (5) can be separated and purified by a known means (eg, chromatography, recrystallization, etc.).
  • the compound (2) can be produced by halogenating the compound (4a) with a carboxylic acid halogenating agent and an alkyl side-chain hepatic agent, and then, if necessary, amidating the compound (4a).
  • Halogenation can be carried out in the same manner as in the reaction of the above Reaction Scheme 3.
  • the amidation is preferably effected by amides (9):
  • the amines (9) are used in 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to compound (4a).
  • reaction solvent examples include alcohols (eg, methanol and ethanol); aromatic hydrocarbons (eg, toluene); and halogenated hydrocarbons (eg, methylene chloride) may be used.
  • alcohols eg, methanol and ethanol
  • aromatic hydrocarbons eg, toluene
  • halogenated hydrocarbons eg, methylene chloride
  • the reaction temperature is 0X: a suitable temperature up to the reflux temperature of the solvent, and the reaction time is 1 to 48 hours.
  • the obtained compound (2) can be separated and purified by a known means (eg, chromatography, recrystallization, etc.).
  • the compound (4) containing the compound (4a) used as a starting material for this reaction can be obtained as a mixture with the compound (2) by the reaction of the above Reaction Scheme 2.
  • Compound (2) can be produced by halogenating compound (10) with a carboxylic acid halogenating agent and an alkyl side chain halogenating agent, and then reacting with compound (8).
  • the halogenation and the reaction with the compound (8) can be carried out in the same manner as in the reaction of the above-mentioned reaction formula 2.
  • the compound (10) as a starting material for this reaction can be produced according to the following reaction formula 6.
  • the compound (10) can be produced by halogenating the compound (3).
  • the halogenation can be carried out in the same manner as in the reaction of the above-mentioned reaction formula 3.
  • the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.
  • the spin coupling constant (J) in the NMR data is indicated by Hertz (Hz).
  • It can be used as an industrial method for producing ⁇ -alkoxyphenylacetic acid derivatives useful as agricultural fungicides.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé d'élaboration de composés de la formule générale (1), se caractérisant par la réaction d'un composé de la formule générale (2) avec un composé de la formule générale (6) QOH, ou sel métallique de ces composés en présence d'une base pour obtenir un composé de la formule générale (11) avant que ce composé ne soit soumis à réaction avec un alcoolat métallique.
PCT/JP1997/000456 1996-02-23 1997-02-20 PROCEDE D'ELABORATION DE DERIVES D'ACIDE α-ALKOXYPHENYLACETIQUE Ceased WO1997030965A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU17335/97A AU1733597A (en) 1996-02-23 1997-02-20 Process for the preparation of alpha-alkoxyphenylacetic acid derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP6212096 1996-02-23
JP8/62120 1996-02-23

Publications (1)

Publication Number Publication Date
WO1997030965A1 true WO1997030965A1 (fr) 1997-08-28

Family

ID=13190891

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1997/000456 Ceased WO1997030965A1 (fr) 1996-02-23 1997-02-20 PROCEDE D'ELABORATION DE DERIVES D'ACIDE α-ALKOXYPHENYLACETIQUE

Country Status (2)

Country Link
AU (1) AU1733597A (fr)
WO (1) WO1997030965A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008117884A1 (fr) * 2007-03-28 2008-10-02 Sumitomo Chemical Company, Limited Procédé de production d'un composé trichloropyrimidine

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995027693A1 (fr) * 1994-04-06 1995-10-19 Shionogi & Co., Ltd. DERIVE D'ACIDE PHENYLACETIQUE A SUBSTITUTION α, SON PROCEDE D'OBTENTION ET BACTERICIDE AGRICOLE LE CONTENANT

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995027693A1 (fr) * 1994-04-06 1995-10-19 Shionogi & Co., Ltd. DERIVE D'ACIDE PHENYLACETIQUE A SUBSTITUTION α, SON PROCEDE D'OBTENTION ET BACTERICIDE AGRICOLE LE CONTENANT

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008117884A1 (fr) * 2007-03-28 2008-10-02 Sumitomo Chemical Company, Limited Procédé de production d'un composé trichloropyrimidine
JP2008266316A (ja) * 2007-03-28 2008-11-06 Sumitomo Chemical Co Ltd ４，５，６−トリクロロピリミジン類の製造方法
US8158787B2 (en) 2007-03-28 2012-04-17 Sumitomo Chemical Company, Limited Process for producing trichloropyrimidine compound

Also Published As

Publication number Publication date
AU1733597A (en) 1997-09-10

Similar Documents

Publication Publication Date Title
JP5016583B2 (ja) アミノピリミジン化合物製造の原料化合物とその製造方法
JP6181168B2 (ja) ある種の２−（ピリジン−３−イル）チアゾール類の製造方法
JP2015520189A (ja) ある種の２−（ピリジン−３−イル）チアゾール類の製造方法
WO2009121288A1 (fr) Procédé de préparation de phénylcarboxamides
CN106632087B (zh) 4-芳基-2-(2-(硫三氟甲基)芳基)喹唑啉的制备方法
CN105246878B (zh) 制备4,6‑双(芳氧基)嘧啶衍生物的方法
CN101547901A (zh) 2-取代的-5-((1-烷硫基)烷基)吡啶的制备方法
CA1216849A (fr) Acide quinolone-carboxyliques; methode de preparation et agents antibacteriens qui renferment ces composes
WO2015105129A1 (fr) Composé de pyrazole substitué par un groupe perfluoroalkyle contenant de l'oxygène éthéré
JP6174161B2 (ja) ２−アミノニコチン酸ベンジルエステル誘導体の製造方法
WO1997030965A1 (fr) PROCEDE D'ELABORATION DE DERIVES D'ACIDE α-ALKOXYPHENYLACETIQUE
CN104628653B (zh) 合成瑞舒伐他汀钙关键中间体的方法
JP6256484B2 (ja) ピリダジン化合物の製造方法
WO2017161555A1 (fr) Intermédiaire de malaxage d'un composé 5-hydroxyl-1,7-naphtyridine substitué par un groupe aryle ou hétéroaryle, et son procédé de préparation
SK8922002A3 (en) Method for producing 4-(heteroaryl-methyl)-halogen-1(2h)- phthalazinones
JP4131337B2 (ja) ３―（イソオキサゾール―５―イル）置換安息香酸誘導体およびその製造法
JP4173599B2 (ja) ６−ヒドロキシ−２−オキソ−１，２，３，４−テトラヒドロキノリンの製造方法
WO2001009098A1 (fr) Derives de n-(benzylsulfonyl)picolinamide, leur procede de preparation et herbicides associes
JP2000063377A (ja) 置換ピリジンの製造方法
JPWO1997030965A1 (ja) α−アルコキシフェニル酢酸誘導体の製造法
JP4110633B2 (ja) ３−アミノ−４−フルオロ−２−不飽和カルボン酸エステル及びその製法
JP4194984B2 (ja) フェニルナフチルイミダゾール化合物
CN103030643B (zh) 六环吲哚类生物碱及其制备方法
JP4518065B2 (ja) 新規ジアルコキシアミドオキシム誘導体及びその製法
JP4518066B2 (ja) ジアルコキシニトリル誘導体及びその製法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG US UZ VN YU AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase