NZ589486A - A process for the preparation of enantiomerically pure 1-(R)-(2-propynylamino)indan - Google Patents
A process for the preparation of enantiomerically pure 1-(R)-(2-propynylamino)indanInfo
- Publication number
- NZ589486A NZ589486A NZ589486A NZ58948609A NZ589486A NZ 589486 A NZ589486 A NZ 589486A NZ 589486 A NZ589486 A NZ 589486A NZ 58948609 A NZ58948609 A NZ 58948609A NZ 589486 A NZ589486 A NZ 589486A
- Authority
- NZ
- New Zealand
- Prior art keywords
- aminoindan
- preparation
- organic solvent
- enantiomerically pure
- salt
- Prior art date
Links
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- XJEVHMGJSYVQBQ-SECBINFHSA-N (1r)-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2[C@H](N)CCC2=C1 XJEVHMGJSYVQBQ-SECBINFHSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003960 organic solvent Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- JDBJJCWRXSVHOQ-UTONKHPSSA-N methanesulfonic acid;(1r)-n-prop-2-ynyl-2,3-dihydro-1h-inden-1-amine Chemical class CS(O)(=O)=O.C1=CC=C2[C@H](NCC#C)CCC2=C1 JDBJJCWRXSVHOQ-UTONKHPSSA-N 0.000 abstract 1
- 229960000245 rasagiline Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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
Landscapes
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| NZ589486A true NZ589486A (en) | 2012-08-31 |
Family
ID=40874479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ589486A NZ589486A (en) | 2008-06-02 | 2009-06-02 | A process for the preparation of enantiomerically pure 1-(R)-(2-propynylamino)indan |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8569545B2 (enExample) |
| EP (1) | EP2285769B1 (enExample) |
| JP (1) | JP5487440B2 (enExample) |
| CN (2) | CN103896779B (enExample) |
| AU (1) | AU2009254927B2 (enExample) |
| CA (2) | CA2723869C (enExample) |
| CY (1) | CY1115577T1 (enExample) |
| NZ (1) | NZ589486A (enExample) |
| PL (1) | PL2285769T3 (enExample) |
| WO (1) | WO2009147430A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009254927B2 (en) * | 2008-06-02 | 2014-03-13 | 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 |
| WO2015033261A1 (en) | 2013-09-03 | 2015-03-12 | 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 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3198834A (en) | 1964-07-27 | 1965-08-03 | Snc Science Union Et Compagnie | Optical isomers of trifluoromethylated phenethylamines |
| US3728388A (en) | 1970-08-10 | 1973-04-17 | Sterling Drug Inc | 1-amino-2,3-disubstituted cyclopropenylium salts |
| US3855227A (en) * | 1972-05-08 | 1974-12-17 | C Hollander | ({31 )-di-o-isopropylidene-2-keto-l-gulonates |
| US3912761A (en) | 1972-05-08 | 1975-10-14 | Hoffmann La Roche | (-)-Di-O-isopropylidene-2-keto-L-gulonates |
| US3928621A (en) | 1974-10-10 | 1975-12-23 | Hoffmann La Roche | Antiinflammatory 2-(2-aminoalkylamino)-1,2-diphenylethanols |
| JPS5283938A (en) | 1976-01-01 | 1977-07-13 | Hoffmann La Roche | Antiiinflammation agent and process for preparing same |
| HU187775B (en) | 1982-07-14 | 1986-02-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | New process for producing propargile-amines of pharmaceutical activity |
| US4833273A (en) | 1986-02-03 | 1989-05-23 | Warner-Lambert Company | Process for the resolution of 1-aminoindanes |
| AU607437B2 (en) | 1986-09-02 | 1991-03-07 | Du Pont Pharmaceuticals Company | Resolution of dl-methyl 3-(4-(2-hydroxy-3-isopropylamino) propoxy)phenylpropionate((dl-esmolol)) |
| CS269271B1 (en) | 1988-05-30 | 1990-04-11 | Hajicek Josef | Method of selegiline's hydrochloride production |
| IL92952A (en) | 1990-01-03 | 1994-06-24 | Teva Pharma | R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them |
| US5744500A (en) | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| US5030725A (en) | 1990-02-06 | 1991-07-09 | Eli Lilly And Company | Method of resolving cis 3-amino-4-[2-(2-furyl)eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one using (-)-DAG |
| CN1031995C (zh) | 1991-01-02 | 1996-06-12 | 奥韦特有限公司 | N-炔丙基-1-氨基茚满的r-对映体的制法 |
| IL111240A (en) * | 1993-10-18 | 2001-10-31 | Teva Pharma | Salts of r(+) - enantiomers of n- propargyl-1-aminoindan and pharmaceutical compositions comprising them |
| US5877218A (en) * | 1994-01-10 | 1999-03-02 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| EP0738149B1 (en) | 1994-01-10 | 2006-11-29 | Teva Pharmaceutical Industries, Ltd. | 1-aminoindan derivatives and compositions thereof |
| JP2840560B2 (ja) | 1994-11-22 | 1998-12-24 | キノイン・ジヨージセル・エーシユ・ベジエーセテイ・テルメーケク・ジヤーラ・エル・テー | 塩化プロパルギルアンモニウム誘導体の製造方法 |
| IL141690A (en) * | 2001-02-27 | 2004-06-20 | Isp Finetech Ltd | Process for preparation of rasagiline and its salts |
| AR044007A1 (es) * | 2003-04-11 | 2005-08-24 | Newron Pharmaceuticals Inc | Metodos para el tratamiento de la enfermedad de parkinson |
| CA2600008A1 (en) | 2005-02-22 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Improved process for the synthesis of enantiomeric indanylamine derivatives |
| JP2009521402A (ja) | 2005-11-17 | 2009-06-04 | テバ ファーマシューティカル インダストリーズ リミティド | プロパルギル化アミノインダンの分離のための方法 |
| CN101062897B (zh) | 2006-04-25 | 2011-11-23 | 重庆医药工业研究院有限责任公司 | 一种制备2，3-二氢-1h-茚-1-胺及其衍生物的改进方法 |
| RS52183B (sr) | 2006-12-14 | 2012-10-31 | Teva Pharmaceutical Industries, Ltd. | Kristalna čvrsta baza razagilina |
| EP1987816A1 (de) | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| NZ589470A (en) | 2008-06-02 | 2012-08-31 | Generics Uk Ltd | A process for the preparation of rasagiline and its analogues |
| AU2009254927B2 (en) * | 2008-06-02 | 2014-03-13 | Generics [Uk] Limited | A process for the preparation of enantiomerically pure amines |
| WO2010013048A1 (en) | 2008-07-30 | 2010-02-04 | Generics [Uk] Limited | Polymorphic form of rasagiline mesylate |
-
2009
- 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 EP EP09757802.5A patent/EP2285769B1/en active Active
- 2009-06-02 PL PL09757802T patent/PL2285769T3/pl unknown
- 2009-06-02 NZ NZ589486A patent/NZ589486A/xx not_active IP Right Cessation
- 2009-06-02 CA CA2723869A patent/CA2723869C/en not_active Expired - Fee Related
- 2009-06-02 CN CN201410143892.0A patent/CN103896779B/zh 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 not_active Ceased
- 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 |
|---|---|
| US20110251288A1 (en) | 2011-10-13 |
| EP2285769A1 (en) | 2011-02-23 |
| EP2285769B1 (en) | 2014-08-13 |
| PL2285769T3 (pl) | 2015-01-30 |
| US20130303741A1 (en) | 2013-11-14 |
| CA2723869A1 (en) | 2009-12-10 |
| CN102123980B (zh) | 2014-05-07 |
| CA2812006A1 (en) | 2009-12-10 |
| AU2009254927A1 (en) | 2009-12-10 |
| WO2009147430A1 (en) | 2009-12-10 |
| US8809589B2 (en) | 2014-08-19 |
| CA2723869C (en) | 2013-07-16 |
| CN103896779B (zh) | 2015-12-30 |
| AU2009254927B2 (en) | 2014-03-13 |
| JP5487440B2 (ja) | 2014-05-07 |
| CA2812006C (en) | 2016-07-26 |
| CN102123980A (zh) | 2011-07-13 |
| CN103896779A (zh) | 2014-07-02 |
| CY1115577T1 (el) | 2017-01-04 |
| JP2011522023A (ja) | 2011-07-28 |
| US8569545B2 (en) | 2013-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 3 YEARS UNTIL 02 JUN 2016 BY SPRUSON + FERGUSON Effective date: 20130503 |
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| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 02 JUN 2017 BY COMPUTER PACKAGES INC Effective date: 20160518 |
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| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 02 JUN 2018 BY RENEWALS TEAM Effective date: 20170518 |
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| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 02 JUN 2019 BY RENEWALS TEAM Effective date: 20180503 |
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| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 02 JUN 2020 BY RENEWALS TEAM Effective date: 20190514 |
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| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 02 JUN 2021 BY ENVOY Effective date: 20200601 |
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| LAPS | Patent lapsed |