EP1144380A1 - A meta-nitro phenol derivative and a process for producing it - Google Patents
A meta-nitro phenol derivative and a process for producing itInfo
- Publication number
- EP1144380A1 EP1144380A1 EP99965757A EP99965757A EP1144380A1 EP 1144380 A1 EP1144380 A1 EP 1144380A1 EP 99965757 A EP99965757 A EP 99965757A EP 99965757 A EP99965757 A EP 99965757A EP 1144380 A1 EP1144380 A1 EP 1144380A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- halogen
- cyano
- 6haloalkyl
- compound
- formula
- 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- Withdrawn
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
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/18—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/08—Six-membered rings
Definitions
- the present invention relates to an intermediate for agricultural chemicals and a process for producing it.
- the present inventors have conducted an investigation for overcoming the defect in the method. As a result, the knowledge that the meta nitration reaction is allowed to proceed when the OH group of phenols is substituted by a specific substituent, was obtained.
- One aspect of the present invention is a meta-nitro phenol derivative of the formula (I):
- Ar is pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, s-triazinyl or s-tetrazinyl in which Ar may be substituted with at least one substituent selected from the group consisting of halogen, cyano, Cl-6alkyl, Cl-6haloalkyl, Cl-6alkoxy, Cl-6haloalkoxy, Cl-6alkylsulfonyl and Cl-6haloalkylsulfonyl.
- Another aspect of the present invention is a process for producing a meta-nitro phenol derivative of the formula (I) which comprises reacting a compound of the formula (II):
- halogen indicates fluorine, chlorine, bromine or iodine.
- Cl-6haloalkyl or Cl-6haloalkoxy indicates Cl-6alkyl or Cl-6alkyl moiety partially or fully substituted with halogen atoms which may be same or different.
- Cl-6alkyl indicates either straight chain or branched alkyls containing 1-6 carbon atoms.
- the pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, s-triazinyl or s-tetrazinyl represented by Ar may be substituted with at least one substituent selected from the group consisting of halogen, cyano, Cl-6alkyl, Cl-6haloalkyl, Cl-6alkoxy, Cl- ⁇ haloalkoxy, Cl-6alkylsulfonyl and Cl-6haloalkylsulfonyl. If there are two or more substituents on Ar, they may be the same or different.
- the meta-nitro phenol derivative of the present invention is preferably as follows:
- the nitration may be preformed either using fuming nitric acid alone or in acetic acid; or using nitric acid in the presence of sulfuric acid.
- the amount of nitric acid is usually from 1 to 4 moles ( preferably, 1.0 to 2.0 moles ) per one mole of the compound of the formula (II).
- the reaction is carried out between 0 to 30 °C.
- the reaction time is usually from
- the compound of the formula (II) can be produced, for example, by the following method.
- X, Y, Z and Ar are as defined above, Hal is halogen and R' is alkyl, phenyl or benzyl unsubstituted or substituted with halogen, alkyl, etc.
- the reaction is conducted in the presence of a solvent and base.
- the solvent may, for example, be an aprotic polar solvent such as acetonitrile, methyl ethyl ketone, dimethylsulfoxide or N,N-dimethylfor ⁇ amide.
- the base may, for example, be an nlknli metal hydride such as sodium hydride or potassium hydride; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal alkoxide such as sodium methoxide or sodium ethoxide; an alkali metal carbonate such as sodium carbonate or potassium carbonate; or a tertiary a ine such as triethylamine; or pyridine.
- the reaction temperature is usually from 0° to 250°C, preferably from 20° to 150°C.
- the reaction time is usually from 1 to 12 hours.
- the compound of the formula (I) is useful as an intermediate for agricultural chemicals, especially for herbicidal compounds.
- a herbicidal compound can be prepared by the procedures as described in WO98/41093 from the compound of the formula (I) or the corresponding amino derivative.
- the compound of the formula (I) can be converted into the amino derivative.
- amino derivatives those wherein Y is hydrogen, may be converted into the amino derivatives wherein Y is halogen.
- Halogenation reaction can be carried out by reacting the starting compound with a halogenating agent such as N-chlorosuccinimide, sulfuryl chloride, or chlorine in a solvent in the presence or absence of a dehydrohalogenating agent at a temperature of 10 to 150°C for a period of 1-24 hours.
- a halogenating agent such as N-chlorosuccinimide, sulfuryl chloride, or chlorine
- the amount of halogenating agent and dehydrohalogenating agent may be respectively from 1-4 equivalents and from 0.001 to 1 equivalent to the starting compound.
- solvent for the reaction examples include aliphatic hydrocarbons such as hexane, pentane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene; ethers such as diethyl ether, dioxane, tetrahydrofuran; esters such as ethyl acetate, butyl acetate; nitro compounds such as nitrobenzene; amides such as N,N-dimethylformamide; sulfur compound such as dimethylsulfoxide; amines such as pyridine, triethylamine; etc. These may be used as single solvents or in combination.
- aliphatic hydrocarbons such as hexane, pentane
- halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, chlorobenzene
- ethers such as diethyl ether, dioxane, t
- either organic or inorganic bases can be used. These are exemplified by pyridine, triethylamine, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.
- the product is isolated by ordinary post-treatment e.g. addition of water and extraction with an organic solvent. If necessary, product is purified by methods such as crystallization or chromatography.
- the compound of the formula (I) can be produced, for example, by the following method.
- X, Y, Z and Ar are as defined above and G is halogen; alkyl sulfonyl which may be substituted by halogen or alkyl; phenyl sulfonyl which may be substituted by halogen or alkyl; benzyl sulfonyl which may be substituted by halogen or alkyl.
- the reaction is conducted in the presence of a base.
- the base may, for example, be an alkah metal hydride such as sodium hydride or potassium hydride; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkah metal carbonate such as sodium carbonate or potassium carbonate; or pyridine.
- the reaction is conducted, if necessary, in the presence of a solvent.
- the solvent may, for example, be a polar solvent such as dimethylsulfoxide, N,N- dimethylformamide or 1,3- ⁇ imethyl-imidazolinone; an aromatic solvent such as toluene, xylene or pyridine; an ethers such as tetrahydrofuran or dioxane.
- the reaction is preferably conducted in the presence of a catalyst, which increases the yield.
- the catalyst may, for example, be an alkali halide such as potassium iodide, potassium bromide or potassium chloride; a cuprous halide such as cuprous iodide, cuprous bromide or cuprous chloride; cupric halide such as cupric iodide, cupric bromide or cupric chloride; copper metal.
- an alkali halide such as potassium iodide, potassium bromide or potassium chloride
- a cuprous halide such as cuprous iodide, cuprous bromide or cuprous chloride
- cupric halide such as cupric iodide, cupric bromide or cupric chloride
- copper metal such as copper metal.
- the reaction is conducted, if necessary, under an azeotropic distillation.
- the reaction temperature is usually from 0 to 350°C, preferably from 100 to 200°C.
- the reaction time is usually from 1 to 12 hours.
- the compound of the formula (III) can be produced, for example, by the following equation.
- X, Y, Z and Ar are as defined above.
- the reaction is conducted in the presence of solvents.
- the solvent may be an aprotic polar solvent such as diethyl ether, acetonitrile, methyl ethyl ketone, or dimethylsulfoxide and a protic solvent such as water, ethyl alcohol, or acetic acid.
- aprotic polar solvent such as diethyl ether, acetonitrile, methyl ethyl ketone, or dimethylsulfoxide
- a protic solvent such as water, ethyl alcohol, or acetic acid.
- the mixed solvent of above solvents sometimes gives preferable results.
- diazotizing agent various nitrites such as sodium nitrite, ethyl nitrite, or tert-but i nitrite.
- the reaction temperature is usually from -10°C to 10°C, preferably from -5°C to 5°C.
- the reaction time is usually from 0.5 to 12 hours.
- the compound of the formula (III) is the useful intermediate, which affords by the reaction with a certain (hetero)aromatic boronic acid according to the following equation, the herbicidal compounds (IV), that has the carbon-carbon linkage between the benzene ring and the (hetero)aromatic ring.
- Iron powder (6.79 g) was added to a solution of 2-(2-chloro-4-fluoro-5- nitrophenoxy)pyrimidine (6.56 g) in acetic acid (70 ml) and the resulting mixture was stirred at room temperature for 3 hours (monitored by TLC).
- the reaction mixture was diluted with ethyl acetate (200 ml), washed with water (100 ml), then saturated sodium chloride solution (50 ml) twice.
- the aqueous phase was extracted with ethyl acetate (100 ml).
- the ethyl acetate extract was washed with saturated sodium chloride (20 ml) twice.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20318098A | 1998-11-30 | 1998-11-30 | |
US203180 | 1998-11-30 | ||
US28106799A | 1999-03-09 | 1999-03-09 | |
US281067 | 1999-03-09 | ||
US42600099A | 1999-10-25 | 1999-10-25 | |
US426000 | 1999-10-25 | ||
PCT/US1999/026016 WO2000032573A1 (en) | 1998-11-30 | 1999-11-22 | A meta-nitro phenol derivative and a process for producing it |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1144380A1 true EP1144380A1 (en) | 2001-10-17 |
EP1144380A4 EP1144380A4 (en) | 2003-11-26 |
Family
ID=27394520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99965757A Withdrawn EP1144380A4 (en) | 1998-11-30 | 1999-11-22 | A meta-nitro phenol derivative and a process for producing it |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1144380A4 (en) |
JP (1) | JP2003506312A (en) |
CN (1) | CN1376145A (en) |
AU (1) | AU2145500A (en) |
WO (1) | WO2000032573A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL167954A (en) | 2000-02-04 | 2007-10-31 | Sumitomo Chemical Co | Pyrimidine derivatives |
US6613718B2 (en) | 2001-10-01 | 2003-09-02 | Ishihara Sangyo Kaisha, Ltd. | Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them |
CN103265820B (en) * | 2013-05-23 | 2014-07-30 | 大连理工大学 | Method for preparing azo dye with alkalescent arylamine serving as diazotization ingredient |
CN103288763B (en) * | 2013-06-20 | 2015-06-03 | 郑州福源动物药业有限公司 | Industrial production method of 2,6-dichloropyrazine |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5686162A (en) * | 1979-12-17 | 1981-07-13 | Mitsui Toatsu Chem Inc | Pyridyl-2-oxy-benzene derivative |
EP0065374A1 (en) * | 1981-05-18 | 1982-11-24 | Zoecon Corporation | Substituted phosphinates and phosphinothioates and their use for the control of weeds |
EP0071572A2 (en) * | 1981-07-28 | 1983-02-09 | Ciba-Geigy Ag | Derivatives of 2-nitro-4- or-5-pyridyloxy-phenylphosphonic acid, process for their preparation, their use as herbicides and/or regulators of plant growth and/or microbicides, as well as the intermediates used for their preparation, the process for their preparation and their use as herbicides |
US4526608A (en) * | 1982-07-14 | 1985-07-02 | Zoecon Corporation | Certain 2-pyridyloxyphenyl-oximino-ether-carboxylates, herbicidal compositions containing same and their herbicidal method of use |
US4605434A (en) * | 1983-07-20 | 1986-08-12 | Ciba-Geigy Corporation | Herbicidal and plant-growth-regulating (2-nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivatives and compositions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ188244A (en) * | 1977-09-13 | 1981-04-24 | Ici Australia Ltd | 2-substituted pyrimidines compositions growth regulating processes |
US4326880A (en) * | 1979-08-14 | 1982-04-27 | Ciba-Geigy Corporation | Derivatives of 5-(pyridyl-2-oxy)-2-nitrobenzoic acid, and herbicidal compositions containing them, and herbicidal methods for using same |
AU549117B2 (en) * | 1980-01-10 | 1986-01-16 | Nyegaard & Co. A/S | Pyrimidine-2-sulphides and their 5-oxides |
US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
US4484941A (en) * | 1981-09-01 | 1984-11-27 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use as herbicides |
DE3614060A1 (en) * | 1986-04-23 | 1987-10-29 | Schering Ag | PYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
US4966622A (en) * | 1988-04-12 | 1990-10-30 | Ciba-Geigy Corporation | N-phenyl-N-pyrimidin-2-ylureas |
PL335697A1 (en) * | 1997-03-14 | 2000-05-08 | Isk Americas Inc | Diaryl ethers and methods of obtaining them as well as herbicidal and dehumidifying compositions containing them |
-
1999
- 1999-11-22 AU AU21455/00A patent/AU2145500A/en not_active Abandoned
- 1999-11-22 EP EP99965757A patent/EP1144380A4/en not_active Withdrawn
- 1999-11-22 CN CN 99815841 patent/CN1376145A/en active Pending
- 1999-11-22 JP JP2000585215A patent/JP2003506312A/en active Pending
- 1999-11-22 WO PCT/US1999/026016 patent/WO2000032573A1/en not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5686162A (en) * | 1979-12-17 | 1981-07-13 | Mitsui Toatsu Chem Inc | Pyridyl-2-oxy-benzene derivative |
EP0065374A1 (en) * | 1981-05-18 | 1982-11-24 | Zoecon Corporation | Substituted phosphinates and phosphinothioates and their use for the control of weeds |
EP0071572A2 (en) * | 1981-07-28 | 1983-02-09 | Ciba-Geigy Ag | Derivatives of 2-nitro-4- or-5-pyridyloxy-phenylphosphonic acid, process for their preparation, their use as herbicides and/or regulators of plant growth and/or microbicides, as well as the intermediates used for their preparation, the process for their preparation and their use as herbicides |
US4526608A (en) * | 1982-07-14 | 1985-07-02 | Zoecon Corporation | Certain 2-pyridyloxyphenyl-oximino-ether-carboxylates, herbicidal compositions containing same and their herbicidal method of use |
US4605434A (en) * | 1983-07-20 | 1986-08-12 | Ciba-Geigy Corporation | Herbicidal and plant-growth-regulating (2-nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivatives and compositions |
Non-Patent Citations (2)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 005, no. 156 (C-074), 6 October 1981 (1981-10-06) & JP 56 086162 A (MITSUI TOATSU CHEM INC), 13 July 1981 (1981-07-13) * |
See also references of WO0032573A1 * |
Also Published As
Publication number | Publication date |
---|---|
AU2145500A (en) | 2000-06-19 |
JP2003506312A (en) | 2003-02-18 |
WO2000032573A8 (en) | 2001-09-13 |
CN1376145A (en) | 2002-10-23 |
WO2000032573A1 (en) | 2000-06-08 |
EP1144380A4 (en) | 2003-11-26 |
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