JP2014503480A - ジュウテリウムリッチなラサギリン - Google Patents
ジュウテリウムリッチなラサギリン Download PDFInfo
- Publication number
- JP2014503480A JP2014503480A JP2013536727A JP2013536727A JP2014503480A JP 2014503480 A JP2014503480 A JP 2014503480A JP 2013536727 A JP2013536727 A JP 2013536727A JP 2013536727 A JP2013536727 A JP 2013536727A JP 2014503480 A JP2014503480 A JP 2014503480A
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- JP
- Japan
- Prior art keywords
- deuterium
- rich
- compound
- pharmaceutically acceptable
- solvent
- Prior art date
- 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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- 229910052805 deuterium Inorganic materials 0.000 title claims description 98
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 title claims description 97
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 title abstract description 29
- 229960000245 rasagiline Drugs 0.000 title description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims description 127
- 238000000034 method Methods 0.000 claims description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 40
- 208000018737 Parkinson disease Diseases 0.000 claims description 22
- RUOKEQAAGRXIBM-UHFFFAOYSA-N n-prop-2-ynyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(NCC#C)CCC2=C1 RUOKEQAAGRXIBM-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 16
- 239000002552 dosage form Substances 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
- 230000000155 isotopic effect Effects 0.000 claims description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 8
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- JDBJJCWRXSVHOQ-UTONKHPSSA-N methanesulfonic acid;(1r)-n-prop-2-ynyl-2,3-dihydro-1h-inden-1-amine Chemical compound CS(O)(=O)=O.C1=CC=C2[C@H](NCC#C)CCC2=C1 JDBJJCWRXSVHOQ-UTONKHPSSA-N 0.000 description 7
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- 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
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
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- 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
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- 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)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Psychology (AREA)
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- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US40674010P | 2010-10-26 | 2010-10-26 | |
| US61/406,740 | 2010-10-26 | ||
| PCT/US2011/057698 WO2012058219A2 (en) | 2010-10-26 | 2011-10-25 | Deuterium enriched rasagiline |
Publications (2)
| Publication Number | Publication Date |
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| JP2014503480A true JP2014503480A (ja) | 2014-02-13 |
| JP2014503480A5 JP2014503480A5 (enExample) | 2014-12-11 |
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| JP2013536727A Pending JP2014503480A (ja) | 2010-10-26 | 2011-10-25 | ジュウテリウムリッチなラサギリン |
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| EP (1) | EP2632254A4 (enExample) |
| JP (1) | JP2014503480A (enExample) |
| KR (1) | KR20140023872A (enExample) |
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| BR (1) | BR112013010308A2 (enExample) |
| CA (1) | CA2816104A1 (enExample) |
| CL (1) | CL2013001101A1 (enExample) |
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| ZA (1) | ZA201303505B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1991214B1 (en) * | 2006-02-21 | 2015-08-05 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of multiple system atrophy |
| EP2007369A4 (en) | 2006-04-03 | 2009-07-01 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF LEG SYNDROME WITHOUT REST |
| EA016820B1 (ru) * | 2006-12-14 | 2012-07-30 | Тева Фармасьютикал Индастриз, Лтд. | Кристаллическое твердое основание разагилина |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| NZ586025A (en) * | 2008-01-11 | 2012-08-31 | Teva Pharma | Rasagiline mesylate tablet coated with a composisiton comprising methacrylic acid - ethyl acrylate copolymer and triethyl citrate |
| ES2389353T3 (es) * | 2008-06-10 | 2012-10-25 | Teva Pharmaceutical Industries Ltd. | Cápsulas de gelatina blanda de rasagilina |
| RS53504B1 (sr) | 2009-07-09 | 2015-02-27 | Ratiopharm Gmbh | Soli razagilina i njihovi farmaceutski preparati |
| US20110130466A1 (en) * | 2009-10-09 | 2011-06-02 | Stefan Lorenzl | Use of rasagiline for the treatment of progressive supranuclear palsy |
| EP2939669A1 (en) * | 2009-12-22 | 2015-11-04 | Teva Pharmaceutical Industries, Ltd. | 3-keto-n-propargyl-1-aminoindan |
| AU2011282716A1 (en) | 2010-07-27 | 2013-03-14 | Teva Pharmaceutical Industries Ltd. | Dispersions of rasagiline citrate |
| AU2011282720B2 (en) | 2010-07-27 | 2016-12-22 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of olfactory dysfunction |
| KR20140090996A (ko) | 2011-10-10 | 2014-07-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | R(+)-n-폼일-프로파길-아미노인단 |
| AU2012323351A1 (en) | 2011-10-10 | 2014-05-22 | Teva Pharmaceutical Industries Ltd. | R(+)-N-methyl-propargyl-aminoindan |
| JP2015529196A (ja) | 2012-08-17 | 2015-10-05 | 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 | ラサギリンの非経口製剤 |
| CN113348018B (zh) * | 2018-12-06 | 2025-04-01 | 内在生物技术有限公司 | 乙酰基-亮氨酸的氘代类似物 |
| CN111323524B (zh) * | 2020-04-08 | 2022-04-15 | 重庆华森制药股份有限公司 | 一种炔丙胺及其杂质的检测方法 |
| CN115947675B (zh) * | 2022-12-21 | 2024-05-31 | 博济医药科技股份有限公司 | 一种雷沙吉兰中间体及其制备方法和应用 |
Citations (3)
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| JP2008531546A (ja) * | 2005-02-22 | 2008-08-14 | 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 | エナンチオマー性インダニルアミン誘導体の合成のための改良されたプロセス |
| WO2009147432A1 (en) * | 2008-06-02 | 2009-12-10 | Generics [Uk] Limited | An improved process for the preparation of amines |
| WO2010085354A1 (en) * | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries Ltd. | Delayed release rasagiline formulation |
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| 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 |
| 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 |
| EP1778196A4 (en) * | 2004-07-26 | 2008-12-17 | Teva Pharma | PHARMACEUTICAL DOSAGES CONTAINING RASAGILINE |
| CN101098685A (zh) * | 2004-11-24 | 2008-01-02 | 特瓦制药工业有限公司 | 雷沙吉兰经口崩解组合物 |
| AU2006310100B2 (en) * | 2005-11-06 | 2012-12-06 | Brain Watch Ltd. | Magnetic resonance imaging and spectroscopy means and methods thereof |
| JP2011522892A (ja) * | 2008-06-13 | 2011-08-04 | 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 | パーキンソン病緩和のためのラサギリン |
| US20100172916A1 (en) * | 2008-11-10 | 2010-07-08 | Auspex Pharmaceuticals, Inc. | Substituted hydroxyphenylamine compounds |
| US20100286124A1 (en) * | 2009-04-10 | 2010-11-11 | Auspex Pharmaceuticals, Inc. | Prop-2-yn-1-amine inhibitors of monoamine oxidase type b |
| EP2473199A1 (en) * | 2009-08-31 | 2012-07-11 | Brain Watch Ltd. | Isotopically labeled neurochemical agents and uses thereof for diagnosing conditions and disorders |
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2011
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- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
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- 2011-10-25 KR KR1020137013167A patent/KR20140023872A/ko not_active Withdrawn
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
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- 2011-10-25 SG SG2013029293A patent/SG189454A1/en unknown
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- 2011-10-25 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
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2013
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- 2013-05-14 ZA ZA2013/03505A patent/ZA201303505B/en unknown
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2014
- 2014-06-20 US US14/310,321 patent/US20140364506A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008531546A (ja) * | 2005-02-22 | 2008-08-14 | 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 | エナンチオマー性インダニルアミン誘導体の合成のための改良されたプロセス |
| WO2009147432A1 (en) * | 2008-06-02 | 2009-12-10 | Generics [Uk] Limited | An improved process for the preparation of amines |
| WO2010085354A1 (en) * | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries Ltd. | Delayed release rasagiline formulation |
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| JPN5010005926; ＫＵＳＨＮＥＲ ＤＪ: ＣＡＮＡＤＩＡＮ ＪＯＵＲＮＡＬ ＯＦ ＰＨＹＳＩＯＬＯＧＹ ＡＮＤ ＰＨＡＲＭＡＣＯＬＯＧＹ Ｖ７７ Ｎ２, 19990201, Ｐ７９-８８ * |
Also Published As
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| US20140364506A1 (en) | 2014-12-11 |
| PH12013500821A1 (en) | 2019-07-03 |
| WO2012058219A3 (en) | 2012-07-26 |
| SG10201508771TA (en) | 2015-11-27 |
| CL2013001101A1 (es) | 2013-09-06 |
| EP2632254A2 (en) | 2013-09-04 |
| AU2011320611A1 (en) | 2013-06-13 |
| NZ610526A (en) | 2015-10-30 |
| MX2013004598A (es) | 2013-07-17 |
| CA2816104A1 (en) | 2012-05-03 |
| SG189454A1 (en) | 2013-05-31 |
| EA201390613A1 (ru) | 2013-11-29 |
| CN103188933A (zh) | 2013-07-03 |
| EP2632254A4 (en) | 2015-08-05 |
| WO2012058219A2 (en) | 2012-05-03 |
| ZA201303505B (en) | 2015-08-26 |
| KR20140023872A (ko) | 2014-02-27 |
| BR112013010308A2 (pt) | 2016-07-05 |
| US20120101168A1 (en) | 2012-04-26 |
| IL225852A0 (en) | 2013-06-27 |
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