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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- A61P11/02—Nasal agents, e.g. decongestants
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- 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
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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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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- Wood Science & Technology (AREA)
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| 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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| EP (1) | EP2632254A4 (enExample) |
| JP (1) | JP2014503480A (enExample) |
| KR (1) | KR20140023872A (enExample) |
| CN (1) | CN103188933A (enExample) |
| AU (1) | AU2011320611A1 (enExample) |
| BR (1) | BR112013010308A2 (enExample) |
| CA (1) | CA2816104A1 (enExample) |
| CL (1) | CL2013001101A1 (enExample) |
| EA (1) | EA201390613A1 (enExample) |
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| WO (1) | WO2012058219A2 (enExample) |
| ZA (1) | ZA201303505B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| WO2009089049A1 (en) * | 2008-01-11 | 2009-07-16 | Teva Pharmaceutical Industries, Ltd. | Rasagiline formulations, their preparation and use |
| US20100008983A1 (en) * | 2008-06-10 | 2010-01-14 | Muhammad Safadi | Rasagiline soft gelatin capsules |
| DK2451771T3 (da) | 2009-07-09 | 2014-09-08 | Ratiopharm Gmbh | Salte af rasagilin og farmaceutiske fremstillingsmåder heraf |
| AU2010304755A1 (en) * | 2009-10-09 | 2012-05-24 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Progressive Supranuclear Palsy |
| EP2515891A4 (en) * | 2009-12-22 | 2013-06-05 | Teva Pharma | 3-keto-N-propargyl-1-aminoindan |
| RU2587330C2 (ru) | 2010-07-27 | 2016-06-20 | Тева Фармасьютикал Индастриз Лтд. | Применение разагилина для лечения обонятельной дисфункции |
| WO2012015946A1 (en) | 2010-07-27 | 2012-02-02 | Teva Pharmaceutical Industries Ltd. | Dispersion of rasagiline citrate |
| HK1200314A1 (en) | 2011-10-10 | 2015-08-07 | Teva Pharmaceuticals Usa, Inc. | R(+)-n-methyl-propargyl-aminoindan |
| HK1200315A1 (en) | 2011-10-10 | 2015-08-07 | Teva Pharmaceutical Industries Ltd. | R(+)-n-formyl-propargyl-aminoindan |
| US9308182B2 (en) | 2012-08-17 | 2016-04-12 | Teva Pharmaceutical Industries, Ltd. | Parenteral formulations of rasagiline |
| BR112021010923A2 (pt) * | 2018-12-06 | 2021-08-24 | Intrabio Ltd | Análogos deuterados de acetileucina |
| 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 |
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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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| 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 |
| EP1778196A4 (en) * | 2004-07-26 | 2008-12-17 | Teva Pharma | PHARMACEUTICAL DOSAGES CONTAINING RASAGILINE |
| US20090111892A1 (en) * | 2004-11-24 | 2009-04-30 | Shulamit Patashnik | Rasagiline Orally Disintegrating Compositions |
| JP2009514946A (ja) * | 2005-11-06 | 2009-04-09 | ブレイン ウォッチ エルティディ | 磁気共鳴画像／分光手段およびその方法 |
| BRPI0909894A2 (pt) * | 2008-06-13 | 2015-07-28 | Teva Pharma | "método de redução da velocidade de progressão de mal de parkinson em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão de mal de parkinson, método de atraso da necessidade de terapia antiparkinsoniana sintomática em um paciente de mal de parkinson em estágio inicial, método de redução do risco de um paciente com mal de parkinson que necessita de terapia antiparkinsoniana, método de redução do declínio funcional de um paciente com mal de parkinson em estágio inicial, método de redução do declínio funcional em um paciente com mal de parkinson, método de tratamento de um paciente que exibe sinais iniciais de mal de parkinson, método de redução da fadiga em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão clínica e tratamento de sintomas de mal de parkinson em um paciente com mal de parkinson, rasagilina ou um sal farmaceuticamente aceitável de rasagilina, composição farmacêutica. |
| 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 AU AU2011320611A patent/AU2011320611A1/en not_active Abandoned
- 2011-10-25 EA EA201390613A patent/EA201390613A1/ru unknown
- 2011-10-25 EP EP11836950.3A patent/EP2632254A4/en not_active Withdrawn
- 2011-10-25 CN CN2011800519198A patent/CN103188933A/zh active Pending
- 2011-10-25 WO PCT/US2011/057698 patent/WO2012058219A2/en not_active Ceased
- 2011-10-25 NZ NZ610526A patent/NZ610526A/en not_active IP Right Cessation
- 2011-10-25 PH PH1/2013/500821A patent/PH12013500821A1/en unknown
- 2011-10-25 US US13/281,054 patent/US20120101168A1/en not_active Abandoned
- 2011-10-25 SG SG10201508771TA patent/SG10201508771TA/en unknown
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2013
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2014
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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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| Title |
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| JPN5010005926; ＫＵＳＨＮＥＲ ＤＪ: ＣＡＮＡＤＩＡＮ ＪＯＵＲＮＡＬ ＯＦ ＰＨＹＳＩＯＬＯＧＹ ＡＮＤ ＰＨＡＲＭＡＣＯＬＯＧＹ Ｖ７７ Ｎ２, 19990201, Ｐ７９-８８ * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2632254A4 (en) | 2015-08-05 |
| CL2013001101A1 (es) | 2013-09-06 |
| CA2816104A1 (en) | 2012-05-03 |
| BR112013010308A2 (pt) | 2016-07-05 |
| SG10201508771TA (en) | 2015-11-27 |
| IL225852A0 (en) | 2013-06-27 |
| US20120101168A1 (en) | 2012-04-26 |
| PH12013500821A1 (en) | 2019-07-03 |
| ZA201303505B (en) | 2015-08-26 |
| US20140364506A1 (en) | 2014-12-11 |
| CN103188933A (zh) | 2013-07-03 |
| AU2011320611A1 (en) | 2013-06-13 |
| EP2632254A2 (en) | 2013-09-04 |
| WO2012058219A2 (en) | 2012-05-03 |
| EA201390613A1 (ru) | 2013-11-29 |
| SG189454A1 (en) | 2013-05-31 |
| NZ610526A (en) | 2015-10-30 |
| KR20140023872A (ko) | 2014-02-27 |
| MX2013004598A (es) | 2013-07-17 |
| WO2012058219A3 (en) | 2012-07-26 |
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