JP2013537530A5 - - Google Patents
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- Publication number
- JP2013537530A5 JP2013537530A5 JP2013521947A JP2013521947A JP2013537530A5 JP 2013537530 A5 JP2013537530 A5 JP 2013537530A5 JP 2013521947 A JP2013521947 A JP 2013521947A JP 2013521947 A JP2013521947 A JP 2013521947A JP 2013537530 A5 JP2013537530 A5 JP 2013537530A5
- Authority
- JP
- Japan
- Prior art keywords
- rasagiline
- solvent
- mixture
- solid dispersion
- der
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims description 34
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 claims description 30
- 229960000245 rasagiline Drugs 0.000 claims description 30
- 239000007962 solid dispersion Substances 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 229920003168 pharmaceutical polymer Polymers 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 238000001238 wet grinding Methods 0.000 claims description 4
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 2
- 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 2
- 239000008247 solid mixture Substances 0.000 claims description 2
- 238000009837 dry grinding Methods 0.000 claims 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 3
- 229920003139 Eudragit® L 100 Polymers 0.000 description 2
- GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- FYUWIEKAVLOHSE-UHFFFAOYSA-N ethenyl acetate;1-ethenylpyrrolidin-2-one Chemical compound CC(=O)OC=C.C=CN1CCCC1=O FYUWIEKAVLOHSE-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40036910P | 2010-07-27 | 2010-07-27 | |
| US61/400,369 | 2010-07-27 | ||
| PCT/US2011/045569 WO2012015946A1 (en) | 2010-07-27 | 2011-07-27 | Dispersion of rasagiline citrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013537530A JP2013537530A (ja) | 2013-10-03 |
| JP2013537530A5 true JP2013537530A5 (enExample) | 2014-09-18 |
Family
ID=45530490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013521947A Withdrawn JP2013537530A (ja) | 2010-07-27 | 2011-07-27 | ラサギリンシトレートの分散物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8691872B2 (enExample) |
| EP (1) | EP2598136A4 (enExample) |
| JP (1) | JP2013537530A (enExample) |
| AU (1) | AU2011282716A1 (enExample) |
| CA (1) | CA2806737A1 (enExample) |
| RU (1) | RU2013108256A (enExample) |
| WO (1) | WO2012015946A1 (enExample) |
Families Citing this family (17)
| 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 |
| 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 |
| AU2011282720B2 (en) | 2010-07-27 | 2016-12-22 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of olfactory dysfunction |
| AU2011282716A1 (en) | 2010-07-27 | 2013-03-14 | Teva Pharmaceutical Industries Ltd. | Dispersions of rasagiline citrate |
| 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 |
| WO2020098774A1 (zh) * | 2018-11-16 | 2020-05-22 | 江苏恒瑞医药股份有限公司 | 一种包含parp抑制剂的药物组合物 |
| WO2022162612A1 (en) | 2021-01-30 | 2022-08-04 | Intas Pharmaceuticals Ltd. | An orodispersible pharmaceutical solid dosage form of rasagiline |
| EP4035654A1 (en) | 2021-01-30 | 2022-08-03 | Intas Pharmaceuticals Limited | An orodispersible pharmaceutical solid dosage form of rasagiline |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IL99759A (en) | 1991-10-16 | 1997-06-10 | Teva Pharma | Mono-fluorinated derivatives of n-propargyl-1-aminoindan, their preparation and pharmaceutical compositions containing them |
| IL115357A (en) | 1995-09-20 | 2000-01-31 | Teva Pharma | Stable compositions containing N-propargyl-1-aminoindan and polyhydric alcohols |
| IL118836A (en) | 1996-07-11 | 2001-01-11 | Teva Pharma | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-aminoindan |
| DE69732984T2 (de) | 1996-12-18 | 2006-02-16 | Teva Pharmaceutical Industries Ltd. | Aminoindanderivate |
| EP2526944B1 (en) | 2002-11-15 | 2016-06-01 | Teva Pharmaceutical Industries Limited | Use of rasagiline with or without riluzole to treat amyotrophic lateral sclerosis |
| CA2547657A1 (en) * | 2003-12-01 | 2005-06-16 | Lifecycle Pharma A/S | Pharmaceutical compositions comprising lercanidipine |
| 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 |
| KR20140103356A (ko) | 2005-02-23 | 2014-08-26 | 테바 파마슈티컬 인더스트리즈 리미티드 | 함량 균일성이 개선된 라사길린 제형 |
| EP1954667B1 (en) | 2005-11-17 | 2017-02-08 | Teva Pharmaceutical Industries Ltd | Methods for isolating propargylated aminoindans |
| US7572834B1 (en) | 2005-12-06 | 2009-08-11 | Teva Pharmaceutical Industries, Ltd. | Rasagiline formulations and processes for their preparation |
| EP1991214B1 (en) | 2006-02-21 | 2015-08-05 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of multiple system atrophy |
| CN101032474B (zh) | 2006-03-06 | 2011-02-16 | 重庆医药工业研究院有限责任公司 | 一种治疗或预防神经系统疾病的雷沙吉兰透皮贴片及其制备方法 |
| EP2007369A4 (en) | 2006-04-03 | 2009-07-01 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF LEG SYNDROME WITHOUT REST |
| EP1892233A1 (de) | 2006-08-18 | 2008-02-27 | Ratiopharm GmbH | Neue Salze des Wirkstoffs Rasagilin |
| WO2008076315A1 (en) | 2006-12-14 | 2008-06-26 | Teva Pharmaceutical Industries, Ltd. | Tannate salt of rasagiline |
| 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 |
| EP2194780A4 (en) | 2007-09-05 | 2010-10-27 | Teva Pharma | METHOD FOR TREATING GLAUCOMA BY RASAGILINE |
| US8188149B2 (en) | 2007-09-17 | 2012-05-29 | Teva Pharmaceutical Industries, Ltd. | Use of R(+)-N-propargy1-1-aminoindan to treat or prevent hearing loss |
| 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 |
| 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 |
| CA2727021A1 (en) | 2008-06-19 | 2009-12-23 | Teva Pharmaceutical Industries Ltd. | Process for purifying rasagiline base |
| WO2009154777A2 (en) | 2008-06-19 | 2009-12-23 | Teva Pharmaceutical Industries, Ltd. | Process for preparing and drying solid rasagiline base |
| DE102008064061A1 (de) | 2008-12-19 | 2010-06-24 | Ratiopharm Gmbh | Feste Zusammensetzung mit dem Wirkstoff Rasagilin |
| EP2218444A3 (en) * | 2009-01-23 | 2010-08-25 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline formulation |
| US8080584B2 (en) | 2009-01-23 | 2011-12-20 | Teva Pharmaceuticals Industries, Ltd. | Delayed release rasagiline citrate formulation |
| 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 |
| AU2011282720B2 (en) | 2010-07-27 | 2016-12-22 | Teva Pharmaceutical Industries Ltd. | Use of rasagiline for the treatment of olfactory dysfunction |
| AU2011282716A1 (en) | 2010-07-27 | 2013-03-14 | Teva Pharmaceutical Industries Ltd. | Dispersions of rasagiline citrate |
| EA201390613A1 (ru) | 2010-10-26 | 2013-11-29 | Тева Фармасьютикал Индастриз Лтд. | Обогащенный дейтерием расагилин |
| AU2012323351A1 (en) | 2011-10-10 | 2014-05-22 | Teva Pharmaceutical Industries Ltd. | R(+)-N-methyl-propargyl-aminoindan |
| US20130089611A1 (en) | 2011-10-10 | 2013-04-11 | Teva Pharmaceutical Industries, Ltd. | Rasagiline citramide |
| KR20140090996A (ko) | 2011-10-10 | 2014-07-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | R(+)-n-폼일-프로파길-아미노인단 |
-
2011
- 2011-07-27 AU AU2011282716A patent/AU2011282716A1/en not_active Abandoned
- 2011-07-27 RU RU2013108256/15A patent/RU2013108256A/ru not_active Application Discontinuation
- 2011-07-27 JP JP2013521947A patent/JP2013537530A/ja not_active Withdrawn
- 2011-07-27 EP EP11813128.3A patent/EP2598136A4/en not_active Withdrawn
- 2011-07-27 WO PCT/US2011/045569 patent/WO2012015946A1/en not_active Ceased
- 2011-07-27 CA CA2806737A patent/CA2806737A1/en not_active Abandoned
- 2011-07-27 US US13/192,082 patent/US8691872B2/en not_active Expired - Fee Related
-
2014
- 2014-03-10 US US14/203,209 patent/US20140194510A1/en not_active Abandoned
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