JP2020023533A - ハロゲン化環式化合物の合成方法 - Google Patents
ハロゲン化環式化合物の合成方法 Download PDFInfo
- Publication number
- JP2020023533A JP2020023533A JP2019186868A JP2019186868A JP2020023533A JP 2020023533 A JP2020023533 A JP 2020023533A JP 2019186868 A JP2019186868 A JP 2019186868A JP 2019186868 A JP2019186868 A JP 2019186868A JP 2020023533 A JP2020023533 A JP 2020023533A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl group
- group
- compound
- addition product
- 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.)
- Pending
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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
ZおよびYは独立して、炭素またはヘテロ原子を表し、
Aは、環において0、1、2または3個の原子を含む、ZとYの間の結合基である)
の環式化合物を製造する方法であって、
(a)式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2はアルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加して、付加生成物を生成する工程と、(b)前記付加生成物を式(III)Y−A−Z(III)(Z、YおよびAは上記で定義されるとおりである)の化合物と反応させる工程と、を含む方法に関する。
のうちの1つに相当する、本発明の式(I)の化合物の製造に適切に用いられる。後者の場合、Aは適切には、−CH2−、−C(=O)−、−CH2−CH2およびCH2−C(=O)−および−C(=S)−から選択され、R3はHまたはC1〜C6アルキルである。
ZおよびYは独立して、炭素またはヘテロ原子を表し、
Aは、環において0、1、2または3個の原子を含む、ZとYの間の結合基である)の環式化合物を合成する方法であって、
式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2は、アルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加することによって得られる付加生成物を、ハロゲン化水素、特に塩化水素の存在下にて、式(III)Y−A−Z(III)(Z、YおよびAは上記で定義されるとおりである)の化合物と反応させる、方法にも関する。
6−(トリフルオロメチル)ピリミジン−2(1H)−オンの製造
トリフルオロアセチルクロリドをエチルビニルエーテルに付加することによって製造された、等モル量の4−エトキシ−1,1,1−トリフルオロ−3−ブテン−2−オン(ETFBO)を、機械攪拌機、還流冷却器および滴下漏斗を備えた三つ口フラスコにおけるメタノール2.2L中の尿素8.74モルの溶液に、N2雰囲気下にて約3時間にわたって、一滴ずつ添加した。反応混合物の温度を15℃未満に維持した。15分後、濃HCl溶液(32%)1.35Lを得られた冷却懸濁液に添加し、透明な溶液が得られた。その溶液をゆっくりと60℃に加熱し、2時間攪拌した後、懸濁液が形成した。60℃で一晩攪拌し、続いて0〜5℃で1時間攪拌した後、沈殿物を濾過除去した。pHが中性になるまで、残留物を水で洗浄し、続いてヘキサン(約500ml)で洗浄した。減圧下にて2Lフラスコ中で回転蒸発器にて一晩乾燥させた後、6−(トリフルオロメチル)ピリミジン−2(1H)−オンが無色の結晶として得られた。収量は1.2kgであった(理論収量85%)。
3−(トリフルオロメチル)1H−ピラゾールの製造
トリフルオロアセチルクロリドをエチルビニルエーテルに付加することによって製造された、等モル量のETFBOを、機械攪拌機、還流冷却器および滴下漏斗を備えた三つ口フラスコにおけるメタノール2.2L中のヒドラジン塩酸塩4.4モルの溶液に、N2雰囲気下にて約4時間にわたって、一滴ずつ添加した。反応混合物の温度を15℃未満に維持した。12時間還流した後、反応バッチを2Lフラスコにおいて濾過し、真空下で濃縮した(同一バッチが同一条件下で製造され、どちらの粗生成物の収率も約95%であった)。続いて、27ミリバールでショートパス真空蒸留によって、合わせた粗生成物を精製した。収量は1105gであり、理論収量92%に相当する。
CETFBOからの6−(トリフルオロメチル)ピリミジン−2(1H)−オンの製造
CETFBOの合成:約−30℃で約2時間冷却された三つ口フラスコ中で、トリフルオロアセチルクロリド4.0モルを濃縮した。−30℃で約2.5時間冷却された液体トリフルオロアセチルクロリドに、エチルビニルエーテル4.0モルを一滴ずつ添加した。HClを除去することなく、CETFBOが定量的に得られた。
3−ピリジンカルボン酸,1,2−ジヒドロ−2−オキソ−6−(トリフルオロメチル)−メチルエステル(MTFPMOC)の製造
約20分間にわたって激しく攪拌しながら、メチルマロンアミド(MMA)420ミリモルを氷冷トリエチルアミン(420ミリモル)に添加した。次いで、エチルビニルエーテルにTFACを付加することによって製造されたETFBOを、氷冷下にて約30分間にわたって一滴ずつ添加し、反応混合物の温度を10℃未満に維持した。次いで、反応混合物をさらに室温で20時間攪拌した。pHが3になるまで、その溶液に濃HCl溶液(2N)を添加した。溶液を酢酸エチルで抽出した後、有機相を水で洗浄し、硫酸ナトリウムで乾燥させた。回転蒸発器で揮発性化合物を除去した後、粗生成物が収率86%で得られた。メタノール/水から結晶化した後、MTFPMOCが純度>98%(GC)で得られた。
3−ピリジンカルボン酸,1,2−ジヒドロ−2−オキソ−6−(トリフルオロメチル)−エチルエステル(ETFPMOC)の製造
約20分間にわたって激しく攪拌しながら、エチルマロンアミド(EMA)420ミリモルを氷冷トリエチルアミン(420ミリモル)に添加した。次いで、エチルビニルエーテルにTFACを付加することによって製造されたETFBOを、氷冷下にて約30分間にわたって一滴ずつ添加し、反応混合物の温度を10℃未満に維持した。次いで、反応混合物をさらに室温で20時間攪拌した。pHが3になるまで、その溶液に濃HCl溶液(2N)を添加した。溶液を酢酸エチルで抽出した後、有機相を水で洗浄し、硫酸ナトリウムで乾燥させた。回転蒸発器で揮発性化合物を除去した後、粗生成物が収率86%で得られた。メタノール/水から結晶化した後、ETFPMOCが純度>98%(GC)で得られた。
Claims (11)
- 式(I):
の環式化合物を製造する方法であって、
(a)式R1−C(O)−X(X=フッ素、塩素または臭素であり、R1は上記で示される意味を有する)の酸ハロゲン化物を式(II)CH2=CH−OR2(II)(R2はアルキル基、アラルキル基またはアリール基である)のビニルエーテルに付加して、付加生成物を生成する工程と、
(b)前記付加生成物を式(III)Y−A−Z(III)(Yは−CH2−C(=O)−O−CH3または−CH2−C(=O)−O−C2H5であり、Aは−C(=O)−であり、Zは−NH2であるか、または、Yは−CH2−C(=O)−O−CH3または−CH2−C(=O)−O−C2H5であり、A−Zは−C≡Nである)の化合物と反応させる工程と、
を含む方法。 - R1が、好ましくはCF3、CF2HおよびCF2Clから選択されるC1〜C3ハロゲン化アルキル基である、請求項1に記載の方法。
- R2が、C1〜C4アルキル基、好ましくはエチル基である、請求項1から6のいずれか一項に記載の方法。
- 工程(a)で生成されたHXが、工程(b)に供給される、請求項1から7のいずれか一項に記載の方法。
- 工程(b)に供給された前記付加生成物が、工程(a)からの粗生成物である、請求項1から8のいずれか一項に記載の方法。
- 工程(b)の前記反応が、範囲−15℃〜+80℃の温度で行われる、請求項1から9のいずれか一項に記載の方法。
- 固液分離または蒸留によって、工程(b)の反応媒体から式(I)の前記化合物を単離することをさらに含む、請求項1から10のいずれか一項に記載の方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2021184880A JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08165547.4 | 2008-09-30 | ||
EP08165547 | 2008-09-30 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017225725A Division JP6647268B2 (ja) | 2008-09-30 | 2017-11-24 | ハロゲン化環式化合物の合成方法 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021184880A Division JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2020023533A true JP2020023533A (ja) | 2020-02-13 |
Family
ID=40351699
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011529509A Active JP6180705B2 (ja) | 2008-09-30 | 2009-09-25 | ハロゲン化環式化合物の合成方法 |
JP2015125708A Active JP6511346B2 (ja) | 2008-09-30 | 2015-06-23 | ハロゲン化環式化合物の合成方法 |
JP2017225725A Active JP6647268B2 (ja) | 2008-09-30 | 2017-11-24 | ハロゲン化環式化合物の合成方法 |
JP2019186868A Pending JP2020023533A (ja) | 2008-09-30 | 2019-10-10 | ハロゲン化環式化合物の合成方法 |
JP2021184880A Pending JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011529509A Active JP6180705B2 (ja) | 2008-09-30 | 2009-09-25 | ハロゲン化環式化合物の合成方法 |
JP2015125708A Active JP6511346B2 (ja) | 2008-09-30 | 2015-06-23 | ハロゲン化環式化合物の合成方法 |
JP2017225725A Active JP6647268B2 (ja) | 2008-09-30 | 2017-11-24 | ハロゲン化環式化合物の合成方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021184880A Pending JP2022028792A (ja) | 2008-09-30 | 2021-11-12 | ハロゲン化環式化合物の合成方法 |
Country Status (7)
Country | Link |
---|---|
US (2) | US8431710B2 (ja) |
EP (1) | EP2334645B1 (ja) |
JP (5) | JP6180705B2 (ja) |
KR (3) | KR20160131129A (ja) |
CN (2) | CN106083710B (ja) |
CA (1) | CA2735921C (ja) |
WO (1) | WO2010037688A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5587307B2 (ja) | 2008-07-04 | 2014-09-10 | ソルヴェイ(ソシエテ アノニム) | アルケノンの製造方法 |
KR20160131129A (ko) | 2008-09-30 | 2016-11-15 | 솔베이(소시에떼아노님) | 할로겐화 환형 화합물의 합성 방법 |
GB0903749D0 (en) * | 2009-03-04 | 2009-04-15 | Syngenta Participations Ag | Chemical process |
US8957254B2 (en) | 2009-07-06 | 2015-02-17 | Solvay Sa | Process for chemical synthesis from an alkenone made from a halogenated precursor |
PL2451763T3 (pl) | 2009-07-06 | 2015-08-31 | Solvay | Sposób wytwarzania halogenowanych prekursorów alkenonów w obecności rozpuszczalnika |
EP2662359A1 (en) | 2012-05-08 | 2013-11-13 | Solvay Sa | Ionic Liquids, Method for manufacturing thereof, and Electrochemical Devices Comprising the Same |
IN2015DN00635A (ja) * | 2012-08-22 | 2015-06-26 | Solvay | |
WO2014096284A1 (en) | 2012-12-20 | 2014-06-26 | Solvay Sa | Salts of n-containing heterocyclic anions as components in electrolytes |
MX2015017640A (es) * | 2013-06-20 | 2016-09-07 | Basf Se | Proceso para preparar compuestos de piridilpirazol y sus derivados de piridilhidrazina. |
EP2987782A1 (en) | 2014-08-22 | 2016-02-24 | Solvay SA | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
WO2016079126A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | Distillation process comprising at least two distillation steps to obtain purified halogenated carboxylic acid halide, and use of the purified halogenated carboxylic acid halide |
EP3031791A1 (en) | 2014-12-10 | 2016-06-15 | Solvay SA | Halogenation process of 1,1-dihaloethene |
EP3199522A1 (en) | 2016-02-01 | 2017-08-02 | Solvay SA | Aminothioate derivatives, production thereof and use |
JP2020532524A (ja) | 2017-09-04 | 2020-11-12 | ソルヴェイ(ソシエテ アノニム) | ジフルオロアセチルクロリドの製造方法及び製造中間体 |
JP6911143B2 (ja) | 2018-11-07 | 2021-07-28 | 福建永晶科技股▲ふん▼有限公司Fujian Yongjing Technology Co., Ltd | ピラゾール又はピリミジノンの新しい製造方法 |
CN113227052A (zh) | 2018-12-27 | 2021-08-06 | 科迪华农业科技有限责任公司 | 磺酰胺除草剂方法中间体的制备 |
CN115038690A (zh) | 2020-01-31 | 2022-09-09 | 索尔维公司 | 用于制造卤代烷基取代的吡啶化合物的方法 |
JP2021079146A (ja) * | 2021-02-22 | 2021-05-27 | 株式会社三洋物産 | 遊技機 |
JP7315071B2 (ja) * | 2021-03-03 | 2023-07-26 | 株式会社三洋物産 | 遊技機 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06505489A (ja) * | 1991-03-07 | 1994-06-23 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 除草性ピリジンスルホンアミド |
JPH09132554A (ja) * | 1995-08-08 | 1997-05-20 | Ishihara Sangyo Kaisha Ltd | 4−アルコキシ−1,1,1−トリフルオロ−3−ブテン−2−オンの製造方法 |
JP2006527170A (ja) * | 2003-06-06 | 2006-11-30 | ゾルファイ フルーオル ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルケノンの簡略化した製法 |
WO2008131860A2 (de) * | 2007-04-30 | 2008-11-06 | Bayer Cropscience Ag | Pyridoncarboxamide, diese enthaltende nutzpflanzenschützende mittel und verfahren zu ihrer herstellung und deren verwendung |
JP6180705B2 (ja) * | 2008-09-30 | 2017-08-16 | ソルヴェイ(ソシエテ アノニム) | ハロゲン化環式化合物の合成方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3420166A1 (de) * | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Pyrimidylphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |
US5235060A (en) | 1991-07-11 | 1993-08-10 | E. I. Du Pont De Nemours And Company | Certain three component ionic substituted pyridine compounds as intermediates for preparation as herbicides |
DE4128828A1 (de) | 1991-08-30 | 1993-03-04 | Basf Ag | Ammonium- oder harnstoffhaltige duengemittel und verfahren zu ihrer herstellung |
JPH08502273A (ja) | 1992-10-13 | 1996-03-12 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | 5−ht▲下4▼レセプターアンタゴニスト用複素環式エステルまたはアミド |
ES2119952T3 (es) | 1993-12-23 | 1998-10-16 | Solvay Fluor & Derivate | Procedimiento para la preparacion de cloruros de acidos polifluoroclorocarboxilicos y perfluorocarboxilicos bajo adicion de cloro. |
GB2305174A (en) * | 1995-09-15 | 1997-04-02 | Zeneca Ltd | Chemical process |
GB9711114D0 (en) * | 1997-05-29 | 1997-07-23 | Merck Sharp & Dohme | Therapeutic agents |
DE19821088A1 (de) | 1998-05-12 | 1999-11-18 | Basf Ag | Modifizierte Polykondensate der Asparaginsäure, Verfahren zu ihrer Herstellung und ihre Verwendung in Düngemitteln |
AU2002235247A1 (en) | 2000-12-29 | 2002-07-16 | Honeywell International, Inc. | Halogenated-alpha,beta-unsaturated-beta-(substituted-amino) carboxylate esters |
DK1601653T3 (da) | 2003-03-07 | 2009-03-30 | Syngenta Participations Ag | Fremgangsmåde til fremstilling af substituerede nikotinsyreestre |
WO2006058201A2 (en) * | 2004-11-23 | 2006-06-01 | Reddy Us Therapeutics, Inc. | Heterocyclic and bicyclic compounds, compositions and methods |
DE102004061593A1 (de) | 2004-12-21 | 2006-06-22 | Abbott Gmbh & Co. Kg | Substituierte N-heterocyclische Verbindungen und ihre therapeutische Verwendung |
EP1940842B1 (en) | 2005-09-29 | 2012-05-30 | Merck Sharp & Dohme Corp. | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
JP5112082B2 (ja) * | 2006-02-02 | 2013-01-09 | クミアイ化学工業株式会社 | ピリドン誘導体及び除草剤 |
EP2422790A1 (en) * | 2007-02-09 | 2012-02-29 | Emory University | Paramyxovirus family inhibitors and methods of use thereof |
EP2008996A1 (en) * | 2007-06-27 | 2008-12-31 | Syngeta Participations AG | Process for the production of pyrazoles |
BRPI0915365B8 (pt) | 2008-07-01 | 2022-06-28 | Dow Agrosciences Llc | Processo para a preparação de 2-triflúor-metil-5-alquil-piridinas substituídas na posição 1 |
JP5587307B2 (ja) | 2008-07-04 | 2014-09-10 | ソルヴェイ(ソシエテ アノニム) | アルケノンの製造方法 |
EP2154167A1 (de) * | 2008-07-30 | 2010-02-17 | Bayer MaterialScience AG | Elektromechanischer Wandler mit einem Polymerelement auf Polyisocyanat-Basis |
JP2012532182A (ja) | 2009-07-06 | 2012-12-13 | ソルヴェイ(ソシエテ アノニム) | 特有の条件下でのアルケノンのハロゲン化前駆体の製造方法 |
PL2451763T3 (pl) | 2009-07-06 | 2015-08-31 | Solvay | Sposób wytwarzania halogenowanych prekursorów alkenonów w obecności rozpuszczalnika |
US8440865B2 (en) | 2009-07-06 | 2013-05-14 | Solvay Sa | Process for the manufacture of alkenones |
JP6194245B2 (ja) * | 2013-12-27 | 2017-09-06 | 株式会社Subaru | 信号機認識装置 |
-
2009
- 2009-09-25 KR KR1020167031136A patent/KR20160131129A/ko active Search and Examination
- 2009-09-25 CN CN201610380671.4A patent/CN106083710B/zh active Active
- 2009-09-25 KR KR1020117009786A patent/KR20110066201A/ko active Search and Examination
- 2009-09-25 US US13/120,505 patent/US8431710B2/en not_active Expired - Fee Related
- 2009-09-25 CA CA2735921A patent/CA2735921C/en not_active Expired - Fee Related
- 2009-09-25 WO PCT/EP2009/062462 patent/WO2010037688A1/en active Application Filing
- 2009-09-25 EP EP09783436.0A patent/EP2334645B1/en active Active
- 2009-09-25 JP JP2011529509A patent/JP6180705B2/ja active Active
- 2009-09-25 CN CN2009801384364A patent/CN102164898A/zh active Pending
- 2009-09-25 KR KR1020197018768A patent/KR20190080972A/ko not_active Application Discontinuation
-
2013
- 2013-04-29 US US13/872,860 patent/US8981115B2/en not_active Expired - Fee Related
-
2015
- 2015-06-23 JP JP2015125708A patent/JP6511346B2/ja active Active
-
2017
- 2017-11-24 JP JP2017225725A patent/JP6647268B2/ja active Active
-
2019
- 2019-10-10 JP JP2019186868A patent/JP2020023533A/ja active Pending
-
2021
- 2021-11-12 JP JP2021184880A patent/JP2022028792A/ja active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06505489A (ja) * | 1991-03-07 | 1994-06-23 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 除草性ピリジンスルホンアミド |
JPH09132554A (ja) * | 1995-08-08 | 1997-05-20 | Ishihara Sangyo Kaisha Ltd | 4−アルコキシ−1,1,1−トリフルオロ−3−ブテン−2−オンの製造方法 |
JP2006527170A (ja) * | 2003-06-06 | 2006-11-30 | ゾルファイ フルーオル ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルケノンの簡略化した製法 |
WO2008131860A2 (de) * | 2007-04-30 | 2008-11-06 | Bayer Cropscience Ag | Pyridoncarboxamide, diese enthaltende nutzpflanzenschützende mittel und verfahren zu ihrer herstellung und deren verwendung |
JP2010524985A (ja) * | 2007-04-30 | 2010-07-22 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | ピリドンカルボキサミド、それを含む作物保護剤、その製造方法及び使用 |
JP6180705B2 (ja) * | 2008-09-30 | 2017-08-16 | ソルヴェイ(ソシエテ アノニム) | ハロゲン化環式化合物の合成方法 |
Non-Patent Citations (1)
Title |
---|
LANG, ROBERT W. ET AL.: "Synthesis of selectively trifluoromethylated pyridine derivatives as potential antihypertensives", HELVETICA CHIMICA ACTA, vol. 71(3), JPN6020036396, 1988, pages 596 - 601, ISSN: 0004353129 * |
Also Published As
Publication number | Publication date |
---|---|
US8981115B2 (en) | 2015-03-17 |
EP2334645A1 (en) | 2011-06-22 |
JP6511346B2 (ja) | 2019-05-15 |
US8431710B2 (en) | 2013-04-30 |
US20130237710A1 (en) | 2013-09-12 |
WO2010037688A1 (en) | 2010-04-08 |
CN102164898A (zh) | 2011-08-24 |
CA2735921A1 (en) | 2010-04-08 |
EP2334645B1 (en) | 2019-11-06 |
CN106083710A (zh) | 2016-11-09 |
JP2015227339A (ja) | 2015-12-17 |
KR20160131129A (ko) | 2016-11-15 |
CN106083710B (zh) | 2021-03-12 |
CA2735921C (en) | 2017-03-21 |
JP2018058869A (ja) | 2018-04-12 |
KR20110066201A (ko) | 2011-06-16 |
JP2012504153A (ja) | 2012-02-16 |
US20110178297A1 (en) | 2011-07-21 |
KR20190080972A (ko) | 2019-07-08 |
JP6647268B2 (ja) | 2020-02-14 |
JP2022028792A (ja) | 2022-02-16 |
JP6180705B2 (ja) | 2017-08-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6647268B2 (ja) | ハロゲン化環式化合物の合成方法 | |
JP4725977B2 (ja) | 2−ジハロアシル−3−アミノ−アクリル酸エステルおよび3−ジハロメチル−ピラゾール−4−カルボン酸エステルの製造方法 | |
US7585998B2 (en) | Method for producing difluoro-acetyl-acetic acid alkylesters | |
WO2018184196A1 (zh) | 一种制备2-芳基丙二酰胺的方法及其应用 | |
KR100585407B1 (ko) | 피리딘-2,3-디카복실레이트 화합물의 제조를 위한 방법 및중간체 | |
US20100029939A1 (en) | Preparation of ketone amides | |
JP4727576B2 (ja) | ジフルオロアセト酢酸のアルキルエステルを調製するための方法 | |
US6320053B1 (en) | Preparation of heteroarylcarboxamides | |
JPH11130752A (ja) | ヘテロアリールカルボン酸アミド類およびエステル類の製造方法 | |
MXPA06000369A (es) | Procedimiento para la preparacion y purificacion de esteres del acido 2-(alcoxialquiliden)-3-cetoalcanoico a partir de esteres del acido 3-cetoalcanoico. | |
JP2008517967A (ja) | フェニル2−ピリミジニルケトン類の製造方法及びその新規中間体 | |
US6462195B1 (en) | Methods for highly selectively o-alkylating amide compounds with the use of copper salts | |
JP4032861B2 (ja) | β−オキソニトリル誘導体又はそのアルカリ金属塩の製法 | |
JP2991832B2 (ja) | ピリミジン誘導体の製造方法 | |
JP5915004B2 (ja) | ピラゾール化合物の製造方法 | |
JP4663105B2 (ja) | 2−スルホニル−4−オキシピリジン誘導体の製造方法 | |
JP4171965B2 (ja) | 4,4−ジフルオロ−3−ブテン−1−オール誘導体の製造法 | |
JP5790195B2 (ja) | ピラゾール化合物の製造方法 | |
WO2010122793A1 (ja) | ピラジン誘導体の製造方法及びその中間体 | |
JP2009046401A (ja) | ヒドラジン化合物の製造方法およびその製造中間体 | |
JPH11140062A (ja) | 2−置換5−ホルミルチアゾール類の製造方法 | |
JPH1077270A (ja) | 2−(1−クロロビニル)ピリジン誘導体およびその製造方法 | |
JP2008518996A (ja) | ピリミジン−5−カルボキシレートの生成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20191011 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200910 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200928 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20201228 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210329 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20210712 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20211112 |
|
C60 | Trial request (containing other claim documents, opposition documents) |
Free format text: JAPANESE INTERMEDIATE CODE: C60 Effective date: 20211112 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20211126 |
|
C21 | Notice of transfer of a case for reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C21 Effective date: 20211129 |
|
A912 | Re-examination (zenchi) completed and case transferred to appeal board |
Free format text: JAPANESE INTERMEDIATE CODE: A912 Effective date: 20220128 |
|
C211 | Notice of termination of reconsideration by examiners before appeal proceedings |
Free format text: JAPANESE INTERMEDIATE CODE: C211 Effective date: 20220207 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20230104 |
|
C876 | Explanation why request for accelerated appeal examination is justified |
Free format text: JAPANESE INTERMEDIATE CODE: C876 Effective date: 20230208 |
|
C22 | Notice of designation (change) of administrative judge |
Free format text: JAPANESE INTERMEDIATE CODE: C22 Effective date: 20230220 |
|
C305 | Report on accelerated appeal examination |
Free format text: JAPANESE INTERMEDIATE CODE: C305 Effective date: 20230227 |
|
C13 | Notice of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: C13 Effective date: 20230313 |