WO2008102720A1 - 光学活性３－アミノピペリジン又はその塩の製造方法 - Google Patents

光学活性３－アミノピペリジン又はその塩の製造方法 Download PDF

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Publication number
WO2008102720A1
WO2008102720A1 PCT/JP2008/052618 JP2008052618W WO2008102720A1 WO 2008102720 A1 WO2008102720 A1 WO 2008102720A1 JP 2008052618 W JP2008052618 W JP 2008052618W WO 2008102720 A1 WO2008102720 A1 WO 2008102720A1
Authority
WO
WIPO (PCT)
Prior art keywords
optically active
aminopiperidine
salt
nipecotamide
deprotection
Prior art date
Application number
PCT/JP2008/052618
Other languages
English (en)
French (fr)
Inventor
Kohei Mori
Masutoshi Nojiri
Akira Nishiyama
Naoaki Taoka
Original Assignee
Kaneka Corporation
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 Kaneka Corporation filed Critical Kaneka Corporation
Priority to JP2009500168A priority Critical patent/JP5265513B2/ja
Priority to EP08711442.7A priority patent/EP2123769B1/en
Priority to US12/449,645 priority patent/US8338142B2/en
Publication of WO2008102720A1 publication Critical patent/WO2008102720A1/ja
Priority to US13/682,840 priority patent/US20130079525A1/en
Priority to US14/633,622 priority patent/US20150166481A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/56—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

Abstract

　本発明は、光学活性３－アミノピペリジン又はその塩の製造法であって、ラセミのニペコタミドを微生物由来の酵素源の存在下、立体選択的に加水分解することにより、光学活性なニペコタミドと光学活性なニペコチン酸に変換した後、光学活性なニペコタミドをアロイル化、ホフマン転位、アミノ基の保護、更に脱保護を経て光学活性アミノピペリジン又はその塩に誘導するか、又は、光学活性なニペコタミドの選択的なＢＯＣ化、ホフマン転位、更に脱保護することにより光学活性アミノピペリジン又はその塩に誘導する方法である。本発明によれば、医薬品中間体として有用な光学活性３－アミノピペリジン又はその塩を、安価で入手容易な原料から工業生産に適用可能な簡便な方法で製造することができる。さらに当該製造法に有用な中間体が提供される。                                                                               
PCT/JP2008/052618 2007-02-19 2008-02-18 光学活性３－アミノピペリジン又はその塩の製造方法 WO2008102720A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2009500168A JP5265513B2 (ja) 2007-02-19 2008-02-18 光学活性３−アミノピペリジン又はその塩の製造方法
EP08711442.7A EP2123769B1 (en) 2007-02-19 2008-02-18 Method for producing optically active 3-aminopiperidine or salt thereof
US12/449,645 US8338142B2 (en) 2007-02-19 2008-02-18 Method for producing optically active 3-aminopiperidine or salt thereof
US13/682,840 US20130079525A1 (en) 2007-02-19 2012-11-21 Method for producing optically active 3-aminopiperidine or salt thereof
US14/633,622 US20150166481A1 (en) 2007-02-19 2015-02-27 Method for producing optically active 3-aminopiperidine or salt thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-037598 2007-02-19
JP2007037598 2007-02-19

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/682,840 Division US20130079525A1 (en) 2007-02-19 2012-11-21 Method for producing optically active 3-aminopiperidine or salt thereof

Publications (1)

Publication Number Publication Date
WO2008102720A1 true WO2008102720A1 (ja) 2008-08-28

Family

ID=39709997

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/052618 WO2008102720A1 (ja) 2007-02-19 2008-02-18 光学活性３－アミノピペリジン又はその塩の製造方法

Country Status (4)

Country Link
US (3) US8338142B2 (ja)
EP (1) EP2123769B1 (ja)
JP (2) JP5265513B2 (ja)
WO (1) WO2008102720A1 (ja)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011010579A1 (ja) 2009-07-21 2011-01-27 住友化学株式会社 光学活性ニペコタミドの製造方法
WO2011034014A1 (ja) * 2009-09-18 2011-03-24 住友化学株式会社 ３－アミノ－１－ｔｅｒｔ－ブトキシカルボニルピペリジンの精製方法
JP2011236157A (ja) * 2010-05-11 2011-11-24 Toray Fine Chemicals Co Ltd 光学活性ニペコチン酸誘導体の製造方法
JP2013500249A (ja) * 2009-07-24 2013-01-07 シンジェンタ リミテッド 製剤
KR20150123267A (ko) * 2013-02-20 2015-11-03 로이터 케미쉐 아파라테바우 카게 거울상 이성질체 농후화된 3-아미노피페리딘의 제조 방법
US9809569B2 (en) 2014-03-14 2017-11-07 Takeda Pharmaceutical Company Limited Process for producing heterocyclic compound
WO2019225267A1 (ja) * 2018-05-22 2019-11-28 株式会社カネカ 光学活性－ｃｉｓ－アミノピペリジンの製造方法

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013533866A (ja) * 2010-06-17 2013-08-29 ドクター レディズ ラボラトリーズ リミテッド ３−アミノピペリジンジヒドロクロリドの単一の鏡像異性体を調製するための方法
CN103319399B (zh) * 2013-05-29 2016-09-21 威海迪素制药有限公司 阿格列汀中间体r-3-氨基哌啶双盐酸盐的制备方法
CN103435538B (zh) * 2013-08-08 2015-10-28 爱斯特（成都）医药技术有限公司 (r)-3-氨基哌啶盐酸盐的制备方法
EP3375778A1 (en) * 2017-03-14 2018-09-19 Artax Biopharma Inc. Aryl-piperidine derivatives
CN112094224B (zh) * 2019-06-18 2022-08-26 浙江医药股份有限公司新昌制药厂 一种带保护基的3-取代-5-氨基哌啶的制备方法
JP7125383B2 (ja) 2019-12-19 2022-08-24 日立造船株式会社 情報処理装置、情報処理方法、および情報処理プログラム
CN111549011B (zh) * 2020-06-03 2023-05-23 卡柔恩赛生物技术湖北有限公司 来源于土曲霉菌的转氨酶突变体及其应用
CN116143687A (zh) * 2023-03-10 2023-05-23 山东汇智药物研究有限公司 一种(r)-3-氨基哌啶双盐酸盐的制备方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07133273A (ja) 1993-09-17 1995-05-23 Kyorin Pharmaceut Co Ltd 光学活性イミダゾリジノン誘導体とその製造方法
JPH07330732A (ja) 1994-06-10 1995-12-19 Kyorin Pharmaceut Co Ltd 光学活性な３−アミノ−１−ベンジルピペリジン誘導体
WO1998035025A1 (fr) 1997-02-07 1998-08-13 Kaneka Corporation Nouvelle carbonyle reductase, gene codant celle-ci et procede d'utilisation
WO2001068604A2 (en) 2000-03-14 2001-09-20 Sepracor, Inc. 3-substituted piperidines comprising urea functionality, and methods of use thereof
JP2002371060A (ja) * 2001-06-18 2002-12-26 Kanegafuchi Chem Ind Co Ltd 光学活性アミノピペリジン誘導体の製造方法
WO2003004496A1 (en) 2001-07-03 2003-01-16 Novo Nordisk A/S Dpp-iv-inhibiting purine derivatives for the treatment of diabetes
JP2004105152A (ja) * 2002-09-20 2004-04-08 Mitsubishi Chemicals Corp （ｒ）−体のアミド結合を選択的に加水分解するアミダーゼ遺伝子及びその利用

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK161690D0 (da) * 1990-07-05 1990-07-05 Novo Nordisk As Fremgangsmaade til fremstilling af enantiomere forbindelser
CA2150526C (en) * 1994-06-09 2005-11-15 Andreas Kiener Biotechnological process for the preparation of cyclic s-.alpha.-amino carboxylic acids and r-.alpha.-amino carboxamides
AU5693996A (en) * 1995-05-08 1996-11-29 Lonza A.G. Biotechnical production process of piperazine r-alpha-carbox ylic acids and piperazine s-alpha-carboxylic acid amide
JPH10127280A (ja) * 1996-10-31 1998-05-19 Tosoh Corp アミダーゼ及びそれを用いたピペリジンカルボン酸類の製法
JP2003517266A (ja) * 1998-02-17 2003-05-27 ジー・ディー・サール・アンド・カンパニー ラクタムの酵素分割方法
AU2001296653A1 (en) * 2000-10-04 2002-04-15 Maxygen, Inc. Enantioselective production of amino carboxylic acids
JP2003199595A (ja) * 2001-10-24 2003-07-15 Daicel Chem Ind Ltd 光学活性マンデル酸誘導体の製造方法
AU2003269850A1 (en) * 2002-10-08 2004-05-04 Novo Nordisk A/S Hemisuccinate salts of heterocyclic dpp-iv inhibitors
US20060122197A1 (en) * 2004-08-10 2006-06-08 Wenqing Yao Amido compounds and their use as pharmaceuticals
EP1851311A2 (en) * 2005-02-10 2007-11-07 Novozymes A/S Enzymatic enantioselective ester or amide hydrolysis or synthesis
BRPI0608392A2 (pt) * 2005-03-02 2009-12-29 Theravance Inc compostos de quinolinona como agonistas do receptor 5-ht4
GB0510139D0 (en) * 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds B1
JP2007001874A (ja) * 2005-06-21 2007-01-11 Dainippon Sumitomo Pharma Co Ltd 環状アミン誘導体の製造方法
JP2007117034A (ja) * 2005-10-31 2007-05-17 Koei Chem Co Ltd 光学活性ニペコチン酸化合物の製造方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07133273A (ja) 1993-09-17 1995-05-23 Kyorin Pharmaceut Co Ltd 光学活性イミダゾリジノン誘導体とその製造方法
JPH07330732A (ja) 1994-06-10 1995-12-19 Kyorin Pharmaceut Co Ltd 光学活性な３−アミノ−１−ベンジルピペリジン誘導体
WO1998035025A1 (fr) 1997-02-07 1998-08-13 Kaneka Corporation Nouvelle carbonyle reductase, gene codant celle-ci et procede d'utilisation
WO2001068604A2 (en) 2000-03-14 2001-09-20 Sepracor, Inc. 3-substituted piperidines comprising urea functionality, and methods of use thereof
JP2002371060A (ja) * 2001-06-18 2002-12-26 Kanegafuchi Chem Ind Co Ltd 光学活性アミノピペリジン誘導体の製造方法
WO2003004496A1 (en) 2001-07-03 2003-01-16 Novo Nordisk A/S Dpp-iv-inhibiting purine derivatives for the treatment of diabetes
JP2004105152A (ja) * 2002-09-20 2004-04-08 Mitsubishi Chemicals Corp （ｒ）−体のアミド結合を選択的に加水分解するアミダーゼ遺伝子及びその利用

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
J. CHEM. SOC., 1987, pages 1127 - 1132
J. ORG. CHEM., vol. 65, 2000, pages 7406 - 7416
KOMEDA H. ET AL.: "A Novel R-Stereoselective Amidase from Pseudomonas sp. MCI3434 Acting on Piperazine-2-tert-butylcarboxamide", EUR. J. BIOCHEM., vol. 271, no. 8, 2004, pages 1580 - 1590, XP008112461 *
KOMEDA H. ET AL.: "S-Stereoselective Piperazine-2-tert-butylcarboxamide Hydrolase from Pseudomonas azotoformans IAM 1603 is a Novel L-Amino Acid Amidase", EUR. J. BIOCHEM., vol. 271, no. 8, 2004, pages 1465 - 1475, XP008112459 *
See also references of EP2123769A4 *
SYNTHETIC COMMUNICATIONS, vol. 28, 1998, pages 3919 - 3926

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011010579A1 (ja) 2009-07-21 2011-01-27 住友化学株式会社 光学活性ニペコタミドの製造方法
JP2011042647A (ja) * 2009-07-21 2011-03-03 Sumitomo Chemical Co Ltd 光学活性ニペコタミドの製造方法
CN102471267A (zh) * 2009-07-21 2012-05-23 住友化学株式会社 光学活性3-哌啶甲酰胺的制造方法
JP2013500249A (ja) * 2009-07-24 2013-01-07 シンジェンタ リミテッド 製剤
WO2011034014A1 (ja) * 2009-09-18 2011-03-24 住友化学株式会社 ３－アミノ－１－ｔｅｒｔ－ブトキシカルボニルピペリジンの精製方法
JP2011063569A (ja) * 2009-09-18 2011-03-31 Sumitomo Chemical Co Ltd ３−アミノ−１−ｔｅｒｔ−ブトキシカルボニルピペリジンの精製方法およびそのクエン酸塩
JP2011236157A (ja) * 2010-05-11 2011-11-24 Toray Fine Chemicals Co Ltd 光学活性ニペコチン酸誘導体の製造方法
JP2016508514A (ja) * 2013-02-20 2016-03-22 ロイター ヒェミッシャー アパラーテバウ コマンディートゲゼルシャフトＲｅｕｔｅｒ Ｃｈｅｍｉｓｃｈｅｒ Ａｐｐａｒａｔｅｂａｕ ＫＧ エナンチオマー濃縮された３−アミノピペリジンの調製のためのプロセス
KR20150123267A (ko) * 2013-02-20 2015-11-03 로이터 케미쉐 아파라테바우 카게 거울상 이성질체 농후화된 3-아미노피페리딘의 제조 방법
JP2018168194A (ja) * 2013-02-20 2018-11-01 ロイター ヒェミッシャー アパラーテバウ コマンディートゲゼルシャフトＲｅｕｔｅｒ Ｃｈｅｍｉｓｃｈｅｒ Ａｐｐａｒａｔｅｂａｕ ＫＧ エナンチオマー濃縮された３−アミノピペリジンの調製のためのプロセス
US10464898B2 (en) 2013-02-20 2019-11-05 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine
KR102236806B1 (ko) * 2013-02-20 2021-04-06 로이터 케미쉐 아파라테바우 이.카. 거울상 이성질체 농후화된 3-아미노피페리딘의 제조 방법
US11472770B2 (en) 2013-02-20 2022-10-18 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine
US11897843B2 (en) 2013-02-20 2024-02-13 Reuter Chemische Apparatebau Kg Process for the preparation of enantiomerically enriched 3-aminopiperidine
US9809569B2 (en) 2014-03-14 2017-11-07 Takeda Pharmaceutical Company Limited Process for producing heterocyclic compound
WO2019225267A1 (ja) * 2018-05-22 2019-11-28 株式会社カネカ 光学活性－ｃｉｓ－アミノピペリジンの製造方法

Also Published As

Publication number Publication date
EP2123769A4 (en) 2012-10-24
EP2123769B1 (en) 2016-05-18
JP5728041B2 (ja) 2015-06-03
JPWO2008102720A1 (ja) 2010-05-27
JP2013136632A (ja) 2013-07-11
US20150166481A1 (en) 2015-06-18
US20100105917A1 (en) 2010-04-29
JP5265513B2 (ja) 2013-08-14
EP2123769A1 (en) 2009-11-25
US20130079525A1 (en) 2013-03-28
US8338142B2 (en) 2012-12-25

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