JP7068467B2 - 置換フェニル酢酸誘導体の製造方法 - Google Patents
置換フェニル酢酸誘導体の製造方法 Download PDFInfo
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- 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
- C07C69/67—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 saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
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- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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- C—CHEMISTRY; METALLURGY
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/457—Saturated compounds containing a keto group being part of a ring containing halogen
- C07C49/467—Saturated compounds containing a keto group being part of a ring containing halogen polycyclic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
- C07C59/225—Saturated compounds having only one carboxyl group and containing keto groups containing —CHO groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、医薬製造の分野に属し、置換フェニル酢酸誘導体の製造方法に関し、特に、2-(4-((2-オキソシクロペンチル)メチル)フェニル)プロパン酸に関する。
米国特許第4161538号には、抗炎症、鎮痛および解熱の良好な医薬活性を有する、置換フェニル酢酸誘導体が開示されている。その構造を、以下に示す。
本発明は、ロキソプロフェンを含む置換フェニル酢酸誘導体の合成工程を提供する。本発明の新規な合成工程は、置換フェニル酢酸およびその誘導体を、低コストかつ高収率で合成することができる。
R2は、ハロゲン、CN、OH、-CH2OH、-CHO、CH3NO2、エステル基、-NR4R5、OTf、OTs、OMs、-C=CR6、または
Zは、シクロペンタノン基、および
L1は、ハロゲン、OH、OMs、OTs、OTf等から選択される好適な脱離基であり、
L2は、R2の定義と同じであり、
Zは、シクロペンタノン基、および
R3は、短鎖アルキル基であり、
L1またはL2は、OMs、OTs、OTf、CH3NO2、-CN、
L2が
R3は、短鎖アルキル基である。
R2は、ハロゲン、-CN、-OH、-CH2OH、-CHO、CH3NO2、エステル基、-NR4R5、OTf、OTs、OMs、-C=CR6、
R3は、短鎖アルキル基である。
R1は、Hであり、
R3の定義は、上記と同じである。
R2は、ハロゲンまたはシアノ基であり、
R3は、低置換アルキル基である。
[実施例1]
Claims (8)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710800788.8 | 2017-09-07 | ||
CN201710800788.8A CN109467506B (zh) | 2017-09-07 | 2017-09-07 | 一种取代苯乙酸衍生物的制备方法 |
PCT/CN2018/099121 WO2019047654A1 (zh) | 2017-09-07 | 2018-08-07 | 一种取代苯乙酸衍生物的制备方法 |
Publications (2)
Publication Number | Publication Date |
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JP2020532593A JP2020532593A (ja) | 2020-11-12 |
JP7068467B2 true JP7068467B2 (ja) | 2022-05-16 |
Family
ID=65633472
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Application Number | Title | Priority Date | Filing Date |
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JP2020535284A Active JP7068467B2 (ja) | 2017-09-07 | 2018-08-07 | 置換フェニル酢酸誘導体の製造方法 |
Country Status (6)
Country | Link |
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US (1) | US20210078941A1 (ja) |
EP (1) | EP3680227A4 (ja) |
JP (1) | JP7068467B2 (ja) |
KR (1) | KR102393122B1 (ja) |
CN (1) | CN109467506B (ja) |
WO (1) | WO2019047654A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109553518B (zh) * | 2017-09-27 | 2021-12-07 | 江苏瑞科医药科技有限公司 | 一种取代苯乙酸衍生物的制备方法 |
CN117203189A (zh) * | 2021-04-14 | 2023-12-08 | 株式会社Lg化学 | 制备用于合成鞘氨醇-1-磷酸酯受体激动剂的中间体的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000327603A (ja) | 1999-05-20 | 2000-11-28 | Ohara Yakuhin Kogyo Kk | プロピオン酸誘導体の製造方法 |
CN101412670A (zh) | 2007-10-19 | 2009-04-22 | 浙江普洛医药科技有限公司 | 洛索洛芬钠的合成方法 |
JP5238757B2 (ja) | 2009-06-26 | 2013-07-17 | レ ラボラトワール セルヴィエ | 新規2−メルカプトシクロペンタンカルボン酸化合物、その製造法、およびそれを含有する薬学的組成物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4161538A (en) * | 1977-04-05 | 1979-07-17 | Sankyo Company Limited | Substituted phenylacetic acid derivatives and process for the preparation thereof |
JPH08245517A (ja) | 1995-03-10 | 1996-09-24 | Kureha Chem Ind Co Ltd | アルキルシクロペンタノン誘導体の製造方法 |
CN104326903A (zh) * | 2014-10-14 | 2015-02-04 | 合肥远志医药科技开发有限公司 | 一种高纯度洛索洛芬钠二水合物的工业化生产方法 |
CN104710309A (zh) * | 2015-02-05 | 2015-06-17 | 浙江普洛医药科技有限公司 | 洛索洛芬钠及其中间体的合成方法 |
CN106316837B (zh) * | 2015-06-24 | 2020-04-24 | 浙江九洲药业股份有限公司 | 一种取代苯乙酸衍生物的制备方法 |
CN105017009A (zh) * | 2015-06-29 | 2015-11-04 | 千辉药业(安徽)有限责任公司 | 一种洛索洛芬钠的合成方法 |
-
2017
- 2017-09-07 CN CN201710800788.8A patent/CN109467506B/zh active Active
-
2018
- 2018-08-07 JP JP2020535284A patent/JP7068467B2/ja active Active
- 2018-08-07 US US16/644,205 patent/US20210078941A1/en not_active Abandoned
- 2018-08-07 KR KR1020207006285A patent/KR102393122B1/ko active IP Right Grant
- 2018-08-07 EP EP18853433.3A patent/EP3680227A4/en not_active Withdrawn
- 2018-08-07 WO PCT/CN2018/099121 patent/WO2019047654A1/zh unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000327603A (ja) | 1999-05-20 | 2000-11-28 | Ohara Yakuhin Kogyo Kk | プロピオン酸誘導体の製造方法 |
CN101412670A (zh) | 2007-10-19 | 2009-04-22 | 浙江普洛医药科技有限公司 | 洛索洛芬钠的合成方法 |
JP5238757B2 (ja) | 2009-06-26 | 2013-07-17 | レ ラボラトワール セルヴィエ | 新規2−メルカプトシクロペンタンカルボン酸化合物、その製造法、およびそれを含有する薬学的組成物 |
Also Published As
Publication number | Publication date |
---|---|
CN109467506B (zh) | 2021-12-07 |
CN109467506A (zh) | 2019-03-15 |
KR20200035109A (ko) | 2020-04-01 |
EP3680227A1 (en) | 2020-07-15 |
US20210078941A1 (en) | 2021-03-18 |
KR102393122B1 (ko) | 2022-05-02 |
JP2020532593A (ja) | 2020-11-12 |
EP3680227A4 (en) | 2021-06-02 |
WO2019047654A1 (zh) | 2019-03-14 |
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