JP2012515775A5 - - Google Patents
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- Publication number
- JP2012515775A5 JP2012515775A5 JP2011547964A JP2011547964A JP2012515775A5 JP 2012515775 A5 JP2012515775 A5 JP 2012515775A5 JP 2011547964 A JP2011547964 A JP 2011547964A JP 2011547964 A JP2011547964 A JP 2011547964A JP 2012515775 A5 JP2012515775 A5 JP 2012515775A5
- Authority
- JP
- Japan
- Prior art keywords
- rasagiline
- dosage form
- citrate
- pharmaceutically acceptable
- acid
- 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.)
- Granted
Links
- 229960000245 rasagiline Drugs 0.000 claims description 106
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical group C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 claims description 105
- 239000002552 dosage form Substances 0.000 claims description 67
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 39
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 14
- 239000000454 talc Substances 0.000 claims description 14
- 229910052623 talc Inorganic materials 0.000 claims description 14
- 235000012222 talc Nutrition 0.000 claims description 14
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229920000881 Modified starch Polymers 0.000 claims description 7
- 235000021355 Stearic acid Nutrition 0.000 claims description 7
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 7
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 7
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 7
- 229960003943 hypromellose Drugs 0.000 claims description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 7
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004014 plasticizer Substances 0.000 claims description 7
- 239000008117 stearic acid Substances 0.000 claims description 7
- 239000001069 triethyl citrate Substances 0.000 claims description 7
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 7
- 235000013769 triethyl citrate Nutrition 0.000 claims description 7
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 6
- 229930195725 Mannitol Natural products 0.000 claims description 6
- 239000007884 disintegrant Substances 0.000 claims description 6
- 239000000594 mannitol Substances 0.000 claims description 6
- 235000010355 mannitol Nutrition 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229920002472 Starch Polymers 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000006186 oral dosage form Substances 0.000 claims description 5
- 230000000291 postprandial effect Effects 0.000 claims description 5
- 239000008107 starch Substances 0.000 claims description 5
- 235000019698 starch Nutrition 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229910002012 Aerosil® Inorganic materials 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 206010021518 Impaired gastric emptying Diseases 0.000 claims description 2
- 238000003109 Karl Fischer titration Methods 0.000 claims description 2
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 2
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 claims description 2
- 238000009500 colour coating Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 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 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20583309P | 2009-01-23 | 2009-01-23 | |
| US61/205,833 | 2009-01-23 | ||
| US12/456,031 US20100189788A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline base formulation |
| US12/456,031 | 2009-06-09 | ||
| US12/455,976 | 2009-06-09 | ||
| US12/456,001 | 2009-06-09 | ||
| US12/456,001 US20100189791A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline malate formulation |
| US12/456,029 US20100189790A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline formulation |
| US12/456,029 | 2009-06-09 | ||
| US12/455,976 US8080584B2 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline citrate formulation |
| US12/689,044 | 2010-01-18 | ||
| US12/689,044 US7855233B2 (en) | 2009-01-23 | 2010-01-18 | Citrate salt of Rasagiline |
| PCT/US2010/000174 WO2010085354A1 (en) | 2009-01-23 | 2010-01-21 | Delayed release rasagiline formulation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014239283A Division JP2015091813A (ja) | 2009-01-23 | 2014-11-26 | 遅延放出ラサギリン製剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012515775A JP2012515775A (ja) | 2012-07-12 |
| JP2012515775A5 true JP2012515775A5 (enExample) | 2013-03-07 |
| JP5774495B2 JP5774495B2 (ja) | 2015-09-09 |
Family
ID=42354337
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011547964A Expired - Fee Related JP5774495B2 (ja) | 2009-01-23 | 2010-01-21 | 遅延放出ラサギリン製剤 |
| JP2014239283A Withdrawn JP2015091813A (ja) | 2009-01-23 | 2014-11-26 | 遅延放出ラサギリン製剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014239283A Withdrawn JP2015091813A (ja) | 2009-01-23 | 2014-11-26 | 遅延放出ラサギリン製剤 |
Country Status (21)
| Country | Link |
|---|---|
| US (9) | US8080584B2 (enExample) |
| EP (3) | EP2381767B1 (enExample) |
| JP (2) | JP5774495B2 (enExample) |
| CN (1) | CN102333442B (enExample) |
| AR (1) | AR075148A1 (enExample) |
| AT (3) | ATE556703T1 (enExample) |
| AU (1) | AU2010206970B2 (enExample) |
| CA (3) | CA2727899C (enExample) |
| CY (2) | CY1112486T1 (enExample) |
| CZ (1) | CZ22819U1 (enExample) |
| DE (1) | DE202010017129U1 (enExample) |
| DK (3) | DK2308477T3 (enExample) |
| EA (1) | EA029262B1 (enExample) |
| ES (3) | ES2564317T3 (enExample) |
| HR (2) | HRP20110745T1 (enExample) |
| IL (1) | IL214220A (enExample) |
| PL (2) | PL2308477T3 (enExample) |
| PT (2) | PT2308477E (enExample) |
| RS (2) | RS52421B (enExample) |
| SI (2) | SI2246321T1 (enExample) |
| WO (1) | WO2010085354A1 (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005269416B2 (en) * | 2004-07-26 | 2011-07-28 | Teva Pharmaceutical Industries, Ltd. | Pharmaceutical dosage forms including rasagiline |
| ZA200704917B (en) * | 2004-11-24 | 2008-11-26 | Teva Pharma | Rasagiline orally disintegrating compositions |
| US8809310B2 (en) * | 2006-02-21 | 2014-08-19 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of multiple system atrophy |
| WO2007117431A2 (en) | 2006-04-03 | 2007-10-18 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of restless legs syndrome |
| EP1892233A1 (de) | 2006-08-18 | 2008-02-27 | Ratiopharm GmbH | Neue Salze des Wirkstoffs Rasagilin |
| CN101557706B (zh) * | 2006-12-14 | 2013-08-07 | 泰华制药工业有限公司 | 雷沙吉兰碱结晶固体 |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| JP2010538067A (ja) * | 2007-09-05 | 2010-12-09 | 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 | ラサギリンを使用する緑内障の治療方法 |
| 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 |
| CA2711817A1 (en) * | 2008-01-11 | 2009-07-16 | Teva Pharmaceutical Industries Ltd. | Rasagiline formulations, their preparation and use |
| WO2009151594A1 (en) * | 2008-06-10 | 2009-12-17 | Teva Pharmaceutical Industries, Ltd. | Rasagiline soft gelatin capsules |
| US20090312436A1 (en) * | 2008-06-13 | 2009-12-17 | Ruth Levy | Rasagiline for parkinson's disease modification |
| AU2009260733B2 (en) * | 2008-06-19 | 2015-01-29 | Teva Pharmaceutical Industries, Ltd. | Process for purifying rasagiline base |
| JP2011524907A (ja) * | 2008-06-19 | 2011-09-08 | 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 | 固体ラサギリン塩基を調製および乾燥する方法 |
| US8080584B2 (en) * | 2009-01-23 | 2011-12-20 | Teva Pharmaceuticals Industries, Ltd. | Delayed release rasagiline citrate formulation |
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| US9675566B2 (en) | 2009-07-16 | 2017-06-13 | Pathologica Llc | Method of treatment with anti-inflammatory and analgesic compounds which are GI-, renal-, and platelet-sparing |
| AU2010304755A1 (en) * | 2009-10-09 | 2012-05-24 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Progressive Supranuclear Palsy |
| CN102048717B (zh) | 2009-10-29 | 2014-02-19 | 重庆医药工业研究院有限责任公司 | 一种稳定的雷沙吉兰组合物 |
| CA2785501A1 (en) * | 2009-12-22 | 2011-07-21 | Teva Pharmaceutical Industries Ltd. | 3-keto-n-propargyl-1-aminoindan |
| EP2598136A4 (en) | 2010-07-27 | 2015-03-25 | Teva Pharma | DISPERSIONS OF RASAGILINE CITRATE |
| RU2587330C2 (ru) | 2010-07-27 | 2016-06-20 | Тева Фармасьютикал Индастриз Лтд. | Применение разагилина для лечения обонятельной дисфункции |
| WO2012058219A2 (en) * | 2010-10-26 | 2012-05-03 | Teva Pharmaceutical Industries Ltd. | Deuterium enriched rasagiline |
| HU231054B1 (hu) * | 2010-11-18 | 2020-04-28 | Egis Gyógyszergyár Nyrt. | Gyógyászati készítmény előállítására alkalmazható új sók |
| WO2012100043A2 (en) | 2011-01-19 | 2012-07-26 | Pathlogica LLC | Controlled release oral pharmaceutical dosage forms comprising mgbg |
| EA201490761A1 (ru) | 2011-10-10 | 2014-11-28 | Тева Фармасьютикал Индастриз Лтд. | R(+)-n-формилпропаргиламиноиндан |
| EA201490760A1 (ru) * | 2011-10-10 | 2014-09-30 | Тева Фармасьютикал Индастриз Лтд. | R(+)-n-метилпропаргиламиноиндан |
| BR112014008550A2 (pt) * | 2011-10-10 | 2017-04-18 | Teva Pharma | citramida rasagilina |
| EP2827848B1 (en) | 2012-03-21 | 2016-04-27 | Synthon BV | Stabilized pharmaceutical compositions comprising rasagiline salts |
| AR092168A1 (es) * | 2012-08-17 | 2015-03-25 | Teva Pharma | Formulaciones parenterales de rasagilina |
| JP2014050039A (ja) * | 2012-09-03 | 2014-03-17 | Sony Corp | 画像処理装置、画像処理方法及びコンピュータプログラム |
| CN105163730B (zh) | 2013-01-08 | 2018-10-30 | 帕萨罗杰卡有限公司 | 用于治疗脱髓鞘疾病的方法和组合物 |
| JP6173098B2 (ja) | 2013-07-30 | 2017-08-02 | キヤノン株式会社 | 光学機器 |
| JP5897196B1 (ja) * | 2015-10-05 | 2016-03-30 | 大同化成工業株式会社 | 糖又は糖アルコール、膨潤型結合剤、崩壊剤及び高吸収性賦形剤を含む複合化造粒物及びその製造方法 |
| CN107049985B (zh) * | 2017-06-07 | 2020-06-19 | 广州帝奇医药技术有限公司 | 一种抗帕金森病药物的长效缓释制剂及其制备方法 |
| CN109028765A (zh) * | 2018-07-02 | 2018-12-18 | 无锡富泽药业有限公司 | 一种盐酸替罗非班的干燥方法 |
| CN109832262A (zh) * | 2019-01-25 | 2019-06-04 | 袁隆平农业高科技股份有限公司 | 活体植物保存方法 |
| CN114469902B (zh) * | 2020-10-23 | 2024-10-29 | 上海上药中西制药有限公司 | 雷沙吉兰或其药用盐舌下膜剂及其制备方法、应用 |
| CN115400090A (zh) * | 2022-10-09 | 2022-11-29 | 北京新领先医药科技发展有限公司 | 一种雷沙吉兰的口崩片组合物及其制备方法 |
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- 2009-06-09 US US12/456,031 patent/US20100189788A1/en not_active Abandoned
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