JP5487440B2 - 鏡像異性的に純粋なアミンの調製方法 - Google Patents
鏡像異性的に純粋なアミンの調製方法 Download PDFInfo
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- JP5487440B2 JP5487440B2 JP2011512213A JP2011512213A JP5487440B2 JP 5487440 B2 JP5487440 B2 JP 5487440B2 JP 2011512213 A JP2011512213 A JP 2011512213A JP 2011512213 A JP2011512213 A JP 2011512213A JP 5487440 B2 JP5487440 B2 JP 5487440B2
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- acid
- rasagiline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- 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
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
- C07C209/88—Separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
鏡像異性的に純粋な(R)−1−アミノインダン(2)およびラサジリン(1)の調製において、先行技術に伴われる困難な点は、本発明で成功裏に解決された。
本発明は、ラサジリン(1)およびラサジリンメシレート等のその薬学上許容される塩に容易に変換できる(参照:例えば、US5457133に記載の方法)、鏡像異性的に純粋な(R)−1−アミノインダン(2)の単純で、簡便で、高価ではない調製方法を提供する。本発明の方法で得られる生成物は、厄介な精製技術を必要とせず、驚くほど非常に純粋である。
(a)ラセミの1−アミノインダンとアルコールの混合物を調整する工程;
(b)必要に応じて水と混合される同じアルコールの中の2,3,4,6−ジ−O−イソプロピリデン−2−ケト−L−グロン酸一水和物を加える工程;
(c)その塩をろ過する工程;
(d)必要に応じて、アルコールと水との混合物の中のその塩を加熱し、冷却して、その塩を単離する工程;
(e)その塩を、無機塩基と水の混合物の中で攪拌する工程;
(f)水非混和性溶媒で抽出する工程;および
(g)その溶媒を留去する工程。
工程(e)において、好ましくは、その塩は、炭酸ナトリウム、炭酸水素ナトリウム、水酸化ナトリウム、炭酸カリウム、水酸化カリウムおよび水酸化アンモニウムを含む群から選択される無機塩基の水溶液と攪拌される。
ラセミの1−アミノインダン(1当量)をメタノール(3 vol)に溶解させて、2,3,4,6−ジ−O−イソプロピリデン−2−ケト−L−グロン酸一水和物(1当量)のメタノール溶液を加えた。沈殿した固体を濾取し、メタノール(1 vol)で洗浄して、真空下、40℃で乾燥した。生成物を白色固体として得た。
収率=40%
化学純度=99.95%(HPLCで測定)
光学純度=96.5%(キラルHPLCで測定)
ラセミの1−アミノインダン(1当量)をメタノール(7 vol)に溶解させて、加熱還流した。2,3,4,6−ジ−O−イソプロピリデン−2−ケト−L−グロン酸一水和物(0.75当量)のメタノール(7 vol)の溶液を調整して、水(7 vol)を加えた。そのグロン酸の溶液を、その反応混合物に還流温度で加えた。その混合物を、1時間加熱還流して、攪拌しながら、ゆっくりと25〜30℃まで放冷した。沈殿した固体を濾取し、メタノール(2 vol)で洗浄して、真空下、40℃で乾燥した。生成物を白色固体として得た。
収率=41〜42%
化学純度=99.96%(HPLCで測定)
光学純度=96.8%(キラルHPLCで測定)
Claims (16)
- 1−アミノインダンと2,3,4,6−ジ−O−イソプロピリデン−2−ケト−L−グロン酸とのジアステレオマー塩の形成工程を含む、鏡像異性的に純粋な(R)−1−アミノインダン(2)の調製方法。
- 塩形成が、有機溶媒または有機溶媒と水との混合物の中で行われる、請求項1記載の方法。
- 有機溶媒が、C1−C6アルコールである、請求項2記載の方法。
- 有機溶媒が、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソブタノール、tert−ブタノールおよびこれらの混合物を含む群から選択される、請求項3記載の方法。
- 有機溶媒が、メタノールまたはメタノールと水との混合物である、請求項4記載の方法。
- 形成されたジアステレオマー塩を再結晶する、先行するいずれかの請求項に記載の方法。
- 形成されたジアステレオマー塩を、有機溶媒、水、またはこれらの混合物から再結晶する、請求項6記載の方法。
- 形成されたジアステレオマー塩を、有機溶媒と水との混合物から再結晶する、請求項7記載の方法。
- 有機溶媒が、C1−C6アルコールである、請求項7または8記載の方法。
- 有機溶媒が、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、イソブタノール、tert−ブタノールおよびこれらの混合物を含む群から選択される、請求項9記載の方法。
- 形成されたジアステレオマー塩を、メタノールと水との混合物から再結晶する、請求項10記載の方法。
- メタノールと水との比が、約1:0.75〜1:1.5の間である、請求項11記載の方法。
- 生成された(R)−1−アミノインダン(2)が、ラサジリン(1)またはその薬学上許容される塩に変換される、先行するいずれかの請求項に記載の方法。
- 薬学上許容される塩が、メシレート塩である、請求項13記載の方法。
- 2−メチルアミノ−1−フェニル−プロパンと2,3,4,6−ジ−O−イソプロピリデン−2−ケト−L−グロン酸とのジアステレオマー塩の形成工程を含む、鏡像異性的に純粋な(R)−2−メチルアミノ−1−フェニル−プロパンの調製方法。
- 生成された(R)−2−メチルアミノ−1−フェニル−プロパンが、セレギリンまたはその薬学上許容される塩に変換される、請求項15に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN973/KOL/2008 | 2008-06-02 | ||
IN973KO2008 | 2008-06-02 | ||
PCT/GB2009/050608 WO2009147430A1 (en) | 2008-06-02 | 2009-06-02 | A process for the preparation of enantiomerically pure amines |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2011522023A JP2011522023A (ja) | 2011-07-28 |
JP2011522023A5 JP2011522023A5 (ja) | 2012-07-19 |
JP5487440B2 true JP5487440B2 (ja) | 2014-05-07 |
Family
ID=40874479
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011512213A Expired - Fee Related JP5487440B2 (ja) | 2008-06-02 | 2009-06-02 | 鏡像異性的に純粋なアミンの調製方法 |
Country Status (10)
Country | Link |
---|---|
US (2) | US8569545B2 (ja) |
EP (1) | EP2285769B1 (ja) |
JP (1) | JP5487440B2 (ja) |
CN (2) | CN103896779B (ja) |
AU (1) | AU2009254927B2 (ja) |
CA (2) | CA2723869C (ja) |
CY (1) | CY1115577T1 (ja) |
NZ (1) | NZ589486A (ja) |
PL (1) | PL2285769T3 (ja) |
WO (1) | WO2009147430A1 (ja) |
Families Citing this family (9)
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CA2723869C (en) * | 2008-06-02 | 2013-07-16 | Generics [Uk] Limited | A process for the preparation of enantiomerically pure amines |
EP2681186B1 (en) | 2011-03-03 | 2016-05-11 | Synthon BV | Process of resolution of 1-aminoindan |
EP3041824A1 (en) | 2013-09-03 | 2016-07-13 | Universidade de Évora | Process for preparing cyclic chiral amines and alcohols by intramolecular catalytic arylation of boronic acid or ester aldehydes and imine substrates |
CN104326920B (zh) * | 2014-10-13 | 2016-03-16 | 江苏清泉化学股份有限公司 | 一种去除间苯二甲胺中杂质的方法 |
CN105018560B (zh) * | 2015-08-13 | 2018-09-14 | 陈永军 | 动态动力学拆分制备(s)-6-甲氧基-1-氨基茚满 |
CN105063161B (zh) * | 2015-08-18 | 2018-11-09 | 陈永军 | 一种r-1-氨基茚满的制备方法 |
CN105087742B (zh) * | 2015-08-18 | 2018-09-14 | 陈永军 | 动态动力学拆分制备r-6-羟基-1-氨基茚满 |
CN105177103B (zh) * | 2015-08-19 | 2019-03-12 | 陈永军 | 一种r-6-羟基-1-氨基茚满的制备方法 |
AR110150A1 (es) * | 2016-11-09 | 2019-02-27 | Roivant Sciences Gmbh | Procesos para la preparación de inhibidores de tph1 |
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CA2723869C (en) * | 2008-06-02 | 2013-07-16 | Generics [Uk] Limited | A process for the preparation of enantiomerically pure amines |
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-
2009
- 2009-06-02 CA CA2723869A patent/CA2723869C/en not_active Expired - Fee Related
- 2009-06-02 NZ NZ589486A patent/NZ589486A/xx not_active IP Right Cessation
- 2009-06-02 AU AU2009254927A patent/AU2009254927B2/en not_active Ceased
- 2009-06-02 US US12/992,451 patent/US8569545B2/en not_active Expired - Fee Related
- 2009-06-02 JP JP2011512213A patent/JP5487440B2/ja not_active Expired - Fee Related
- 2009-06-02 CA CA2812006A patent/CA2812006C/en not_active Expired - Fee Related
- 2009-06-02 WO PCT/GB2009/050608 patent/WO2009147430A1/en active Application Filing
- 2009-06-02 PL PL09757802T patent/PL2285769T3/pl unknown
- 2009-06-02 CN CN201410143892.0A patent/CN103896779B/zh not_active Expired - Fee Related
- 2009-06-02 EP EP09757802.5A patent/EP2285769B1/en active Active
- 2009-06-02 CN CN200980129438.7A patent/CN102123980B/zh not_active Expired - Fee Related
-
2013
- 2013-07-18 US US13/944,956 patent/US8809589B2/en active Active
-
2014
- 2014-09-23 CY CY20141100771T patent/CY1115577T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
AU2009254927B2 (en) | 2014-03-13 |
WO2009147430A1 (en) | 2009-12-10 |
AU2009254927A1 (en) | 2009-12-10 |
US20110251288A1 (en) | 2011-10-13 |
US20130303741A1 (en) | 2013-11-14 |
CN103896779A (zh) | 2014-07-02 |
CN103896779B (zh) | 2015-12-30 |
JP2011522023A (ja) | 2011-07-28 |
CA2723869C (en) | 2013-07-16 |
CN102123980B (zh) | 2014-05-07 |
US8809589B2 (en) | 2014-08-19 |
EP2285769A1 (en) | 2011-02-23 |
EP2285769B1 (en) | 2014-08-13 |
US8569545B2 (en) | 2013-10-29 |
CA2812006A1 (en) | 2009-12-10 |
CA2723869A1 (en) | 2009-12-10 |
CY1115577T1 (el) | 2017-01-04 |
CA2812006C (en) | 2016-07-26 |
NZ589486A (en) | 2012-08-31 |
PL2285769T3 (pl) | 2015-01-30 |
CN102123980A (zh) | 2011-07-13 |
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