JP2010248198A - (2r)−2−プロピルオクタン酸の製造方法 - Google Patents
(2r)−2−プロピルオクタン酸の製造方法 Download PDFInfo
- Publication number
- JP2010248198A JP2010248198A JP2010116000A JP2010116000A JP2010248198A JP 2010248198 A JP2010248198 A JP 2010248198A JP 2010116000 A JP2010116000 A JP 2010116000A JP 2010116000 A JP2010116000 A JP 2010116000A JP 2010248198 A JP2010248198 A JP 2010248198A
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- Prior art keywords
- acid
- optical purity
- octanoic acid
- propyloctanoic acid
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- 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.)
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
Abstract
【解決手段】このような(2R)−2−プロピルオクタン酸は、(2S)−2−(2−プロピニル)オクタン酸または(2S)−2−(2−プロペニル)オクタン酸を白金カーボンを用いて還元反応に付すことにより得ることができる。医薬品としては、アストロサイトの機能異常による神経変性疾患の予防および/または治療剤が挙げられる。
【選択図】なし
Description
その使用量は、原料に対し、好ましくは0.1〜20%、より好ましくは0.1〜10%である。
本発明の方法によれば異性化が起こらず、従来の方法(触媒としてパラジウムカーボンを用いる還元方法)に比べて、光学純度の高い(2R)−2−プロピルオクタン酸を得ることができる。
(2S)−2−(2−プロペニル)オクタン酸 シクロヘキシルアミン塩
(2S)−2−(2−プロペニル)オクタン酸
光学純度(ガスクロマトグラフィにより測定):99.8%e.e.。
白金カーボン触媒による(2R)−2−プロピルオクタン酸の製造
光学純度(HPLCにより測定):99.4%e.e.。
白金カーボン触媒による(2R)−2−プロピルオクタン酸の製造
光学純度(HPLCにより測定):99.34%e.e.。
パラジウム炭素触媒による(2R)−2−プロピルオクタン酸の製造
光学純度(HPLCにより測定):95.2%e.e.。
パラジウム炭素触媒による(2R)−2−プロピルオクタン酸の製造
光学純度(HPLCにより測定):97.14%e.e.。
Claims (3)
- 99.3%e.e.以上の光学純度を有する(2R)−2−プロピルオクタン酸。
- (2S)−2−(2−プロピニル)オクタン酸または(2S)−2−(2−プロペニル)オクタン酸を白金−カーボン触媒を用いて還元反応に付すことにより得られる、99.3%e.e.以上の光学純度を有する(2R)−2−プロピルオクタン酸。
- 99.3%e.e.以上の光学純度を有する(2R)−2−プロピルオクタン酸を含有してなる、アストロサイトの機能異常による神経変性疾患の予防および/または治療剤。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010116000A JP5343925B2 (ja) | 1999-02-18 | 2010-05-20 | (2r)−2−プロピルオクタン酸の製造方法 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1999039758 | 1999-02-18 | ||
JP3975899 | 1999-02-18 | ||
JP2010116000A JP5343925B2 (ja) | 1999-02-18 | 2010-05-20 | (2r)−2−プロピルオクタン酸の製造方法 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000599723A Division JP4752989B2 (ja) | 1999-02-18 | 2000-02-17 | (2r)−2−プロピルオクタン酸の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010248198A true JP2010248198A (ja) | 2010-11-04 |
JP5343925B2 JP5343925B2 (ja) | 2013-11-13 |
Family
ID=12561862
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000599723A Expired - Fee Related JP4752989B2 (ja) | 1999-02-18 | 2000-02-17 | (2r)−2−プロピルオクタン酸の製造方法 |
JP2010116000A Expired - Fee Related JP5343925B2 (ja) | 1999-02-18 | 2010-05-20 | (2r)−2−プロピルオクタン酸の製造方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000599723A Expired - Fee Related JP4752989B2 (ja) | 1999-02-18 | 2000-02-17 | (2r)−2−プロピルオクタン酸の製造方法 |
Country Status (19)
Country | Link |
---|---|
US (1) | US6608221B1 (ja) |
EP (3) | EP1153910B1 (ja) |
JP (2) | JP4752989B2 (ja) |
KR (1) | KR100666423B1 (ja) |
CN (4) | CN101100422A (ja) |
AT (1) | ATE359256T1 (ja) |
AU (1) | AU776927B2 (ja) |
BR (1) | BR0008261A (ja) |
CA (1) | CA2364308C (ja) |
DE (1) | DE60034316T2 (ja) |
ES (1) | ES2283287T3 (ja) |
HU (1) | HUP0200358A3 (ja) |
MX (1) | MXPA01008241A (ja) |
NO (1) | NO20013971D0 (ja) |
NZ (1) | NZ513569A (ja) |
RU (1) | RU2297406C2 (ja) |
TW (1) | TWI268921B (ja) |
WO (1) | WO2000048982A1 (ja) |
ZA (1) | ZA200106500B (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI268921B (en) * | 1999-02-18 | 2006-12-21 | Ono Pharmaceutical Co | A process for preparing (2R)-2-propyloctanoic acid |
CA2453478A1 (en) | 2001-07-18 | 2003-01-30 | Ono Pharmaceutical Co., Ltd. | Agent for treatment of cerebral ischemic diseases |
JP2005298334A (ja) * | 2001-12-19 | 2005-10-27 | Ono Pharmaceut Co Ltd | 新規な中間体化合物およびそれを用いる化合物の製造方法 |
US7928143B2 (en) * | 2003-10-03 | 2011-04-19 | Ono Pharmaceutical Co., Ltd. | Method for preventing and/or treating neurodegenerative diseases |
CN1889941A (zh) * | 2003-10-03 | 2007-01-03 | 小野药品工业株式会社 | 包含(2r)-2-丙基辛酸作为活性成分的输液制剂 |
KR101144553B1 (ko) | 2003-10-03 | 2012-05-11 | 오노 야꾸힝 고교 가부시키가이샤 | (2r)-2-프로필옥탄산을 유효 성분으로 함유하는 약제 |
EP1741697B1 (en) * | 2004-04-28 | 2012-12-19 | Ono Pharmaceutical Co., Ltd. | Crystal comprising (2r)-2-propyloctanoic acid and dibenzylamine |
KR20070085379A (ko) * | 2004-11-16 | 2007-08-27 | 머크 앤드 캄파니 인코포레이티드 | 뇌졸중 치료용 (2r)-2-프로필옥탄산의 프로드럭 |
WO2006075596A1 (ja) * | 2005-01-13 | 2006-07-20 | Kuraray Co., Ltd. | 2-アリルカルボン酸化合物の製造方法 |
EP1859795A4 (en) | 2005-03-15 | 2008-06-04 | Ono Pharmaceutical Co | THERAPEUTIC AGENT FOR OPHTHALMIC DISEASES |
US8975298B2 (en) | 2005-06-27 | 2015-03-10 | Ono Pharmaceutical Co., Ltd. | Therapeutic agent for pain |
CA2625341A1 (en) | 2005-10-18 | 2007-04-26 | Ono Pharmaceutical Co., Ltd. | Pharmaceutical for protection of motor nerve in patient with amyotrophic lateral sclerosis |
EP1974727A4 (en) | 2005-12-22 | 2009-12-09 | Ono Pharmaceutical Co | THERAPEUTIC AGENT AGAINST ACUTE CEREBRALINE INFARC |
US20090118542A1 (en) * | 2006-02-16 | 2009-05-07 | Shigeya Yamazaki | Process for Production of Optically Active Carboxlic Acid Compound |
EP2015741A4 (en) * | 2006-05-04 | 2009-12-23 | Merck & Co Inc | HISTONE DESACETYLASE INHIBITORS FOR THE TREATMENT OF NEURODEGENERATION |
CN102417445B (zh) * | 2011-11-05 | 2013-11-13 | 中国科学院山西煤炭化学研究所 | 一种由马来酸合成丁二酸的方法 |
CN102675166B (zh) * | 2012-05-11 | 2014-03-26 | 山东齐都药业有限公司 | 用于制备2-丙基庚酸的新中间体、其制备方法及2-丙基庚酸的制备方法 |
CN102786407B (zh) * | 2012-08-15 | 2014-04-16 | 湖北大学 | 一种制备(2r)-2-丙基辛酸的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08291106A (ja) * | 1995-04-24 | 1996-11-05 | Ono Pharmaceut Co Ltd | 光学活性な2−プロピルオクタン酸の製造方法 |
WO2000048982A1 (fr) * | 1999-02-18 | 2000-08-24 | Ono Pharmaceutical Co., Ltd. | Procede de preparation d'acide (2r)-2-propyloctanoique |
WO2005105722A1 (ja) * | 2004-04-28 | 2005-11-10 | Ono Pharmaceutical Co., Ltd. | (2r)−2−プロピルオクタン酸とアミンとからなる結晶 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2317019A1 (de) | 1972-04-27 | 1973-11-08 | Upjohn Co | Neue 4,5-didehydro-prostaglandine |
JPH0672123B2 (ja) * | 1986-08-21 | 1994-09-14 | セントラル硝子株式会社 | トリフルオロメチル基を有するシクロヘキサンカルボン酸の製造方法 |
JP2868183B2 (ja) | 1988-02-29 | 1999-03-10 | 株式式社三和化学研究所 | 光学活性を有する4−オキソ−1−ベンゾピラン−2−カルボン酸誘導体の製法、その合成用中間体並びに該中間体の製法 |
TW248552B (ja) * | 1993-06-01 | 1995-06-01 | Onoda Yakuhin Kogyo Kk | |
JP3084345B2 (ja) * | 1995-04-26 | 2000-09-04 | 小野薬品工業株式会社 | 光学活性な2−プロピルオクタン酸の製造方法 |
TW509672B (en) | 1998-05-12 | 2002-11-11 | Ono Pharmaceutical Co | Novel intermediate compounds and processes for the production of optical active octanoic acid derivatives |
-
2000
- 2000-02-16 TW TW089102580A patent/TWI268921B/zh not_active IP Right Cessation
- 2000-02-17 NZ NZ513569A patent/NZ513569A/xx not_active IP Right Cessation
- 2000-02-17 KR KR1020017010357A patent/KR100666423B1/ko not_active IP Right Cessation
- 2000-02-17 CN CNA2006100997275A patent/CN101100422A/zh active Pending
- 2000-02-17 BR BR0008261-9A patent/BR0008261A/pt not_active Application Discontinuation
- 2000-02-17 WO PCT/JP2000/000900 patent/WO2000048982A1/ja active IP Right Grant
- 2000-02-17 RU RU2001125501/04A patent/RU2297406C2/ru active
- 2000-02-17 CN CNA2006101002245A patent/CN1907938A/zh active Pending
- 2000-02-17 MX MXPA01008241A patent/MXPA01008241A/es active IP Right Grant
- 2000-02-17 EP EP00904007A patent/EP1153910B1/en not_active Expired - Lifetime
- 2000-02-17 EP EP06012511A patent/EP1714956A1/en not_active Withdrawn
- 2000-02-17 CN CNB008040133A patent/CN1183082C/zh not_active Expired - Fee Related
- 2000-02-17 AU AU25730/00A patent/AU776927B2/en not_active Ceased
- 2000-02-17 DE DE60034316T patent/DE60034316T2/de not_active Expired - Lifetime
- 2000-02-17 US US09/890,651 patent/US6608221B1/en not_active Expired - Fee Related
- 2000-02-17 EP EP06012510A patent/EP1721882A1/en not_active Withdrawn
- 2000-02-17 HU HU0200358A patent/HUP0200358A3/hu unknown
- 2000-02-17 AT AT00904007T patent/ATE359256T1/de not_active IP Right Cessation
- 2000-02-17 CA CA002364308A patent/CA2364308C/en not_active Expired - Fee Related
- 2000-02-17 CN CNB2004100927127A patent/CN100430364C/zh not_active Expired - Fee Related
- 2000-02-17 ES ES00904007T patent/ES2283287T3/es not_active Expired - Lifetime
- 2000-02-17 JP JP2000599723A patent/JP4752989B2/ja not_active Expired - Fee Related
-
2001
- 2001-08-07 ZA ZA200106500A patent/ZA200106500B/en unknown
- 2001-08-15 NO NO20013971A patent/NO20013971D0/no not_active Application Discontinuation
-
2010
- 2010-05-20 JP JP2010116000A patent/JP5343925B2/ja not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08291106A (ja) * | 1995-04-24 | 1996-11-05 | Ono Pharmaceut Co Ltd | 光学活性な2−プロピルオクタン酸の製造方法 |
WO2000048982A1 (fr) * | 1999-02-18 | 2000-08-24 | Ono Pharmaceutical Co., Ltd. | Procede de preparation d'acide (2r)-2-propyloctanoique |
WO2005105722A1 (ja) * | 2004-04-28 | 2005-11-10 | Ono Pharmaceutical Co., Ltd. | (2r)−2−プロピルオクタン酸とアミンとからなる結晶 |
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