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 | ||
| US12/456,029 | 2009-06-09 | ||
| US12/456,001 US20100189791A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline malate formulation |
| US12/455,976 | 2009-06-09 | ||
| US12/456,029 US20100189790A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline formulation |
| US12/456,001 | 2009-06-09 | ||
| US12/455,976 US8080584B2 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline citrate formulation |
| US12/456,031 | 2009-06-09 | ||
| US12/456,031 US20100189788A1 (en) | 2009-01-23 | 2009-06-09 | Delayed release rasagiline base formulation |
| US12/689,044 US7855233B2 (en) | 2009-01-23 | 2010-01-18 | Citrate salt of Rasagiline |
| US12/689,044 | 2010-01-18 | ||
| 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 (cg-RX-API-DMAC7.html) | 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) | US20100189791A1 (cg-RX-API-DMAC7.html) |
| EP (3) | EP2381767B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5774495B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102333442B (cg-RX-API-DMAC7.html) |
| AR (1) | AR075148A1 (cg-RX-API-DMAC7.html) |
| AT (3) | AT12508U1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2010206970B2 (cg-RX-API-DMAC7.html) |
| CA (3) | CA2799515A1 (cg-RX-API-DMAC7.html) |
| CY (2) | CY1112486T1 (cg-RX-API-DMAC7.html) |
| CZ (1) | CZ22819U1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE202010017129U1 (cg-RX-API-DMAC7.html) |
| DK (3) | DK2246321T3 (cg-RX-API-DMAC7.html) |
| EA (1) | EA029262B1 (cg-RX-API-DMAC7.html) |
| ES (3) | ES2564317T3 (cg-RX-API-DMAC7.html) |
| HR (2) | HRP20110745T1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL214220A (cg-RX-API-DMAC7.html) |
| PL (2) | PL2246321T3 (cg-RX-API-DMAC7.html) |
| PT (2) | PT2308477E (cg-RX-API-DMAC7.html) |
| RS (2) | RS52033B (cg-RX-API-DMAC7.html) |
| SI (2) | SI2308477T1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2010085354A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2007217349B9 (en) * | 2006-02-21 | 2013-06-27 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Multiple System Atrophy |
| CA2646250A1 (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 |
| PT2101569E (pt) * | 2006-12-14 | 2012-01-13 | Teva Pharma | Base de rasagilina sólida cristalina |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| US20090062400A1 (en) * | 2007-09-05 | 2009-03-05 | Laurence Oron | Method of treating glaucoma using 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 |
| KR20100107028A (ko) * | 2008-01-11 | 2010-10-04 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라사길린 제형, 그들의 제법 및 용도 |
| EP2285214B1 (en) * | 2008-06-10 | 2012-05-16 | Teva Pharmaceutical Industries Ltd. | Rasagiline soft gelatin capsules |
| 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. |
| AU2009260733B2 (en) * | 2008-06-19 | 2015-01-29 | Teva Pharmaceutical Industries, Ltd. | Process for purifying rasagiline base |
| US7968749B2 (en) * | 2008-06-19 | 2011-06-28 | Teva Pharmaceutical Industries, Ltd. | Process for preparing and drying solid rasagiline base |
| US20100189791A1 (en) * | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline malate formulation |
| ITPR20090047A1 (it) * | 2009-06-16 | 2010-12-17 | Agricola Cerasaro S S Soc | Procedimento per la produzione di un trito o crema di aglio e trito o crema di aglio cosi' ottenuta |
| PL2451771T3 (pl) | 2009-07-09 | 2014-12-31 | Ratiopharm Gmbh | Sole rasagiliny i ich preparaty farmaceutyczne |
| 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 |
| WO2011042812A1 (en) * | 2009-10-09 | 2011-04-14 | Stefan Lorenzl | 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 |
| MX2012007375A (es) * | 2009-12-22 | 2012-07-30 | Teva Pharma | 3-ceto-n-propargil 1-aminoindano. |
| JP2013537530A (ja) | 2010-07-27 | 2013-10-03 | 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 | ラサギリンシトレートの分散物 |
| EP2603212A4 (en) | 2010-07-27 | 2014-01-08 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF SMOKING DISORDER |
| BR112013010308A2 (pt) * | 2010-10-26 | 2016-07-05 | Teva Pharma | rasagilina de deutério enriquecido |
| 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 |
| BR112014008555A2 (pt) | 2011-10-10 | 2017-04-18 | Teva Pharma | r(+)-n-formil-propargil-aminoindano |
| 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 |
| ES2584059T3 (es) | 2012-03-21 | 2016-09-23 | Synthon Bv | Composiciones farmacéuticas estabilizadas que comprenden sales de rasagilina |
| WO2014028868A1 (en) * | 2012-08-17 | 2014-02-20 | Teva Pharmaceutical Industries Ltd. | Parenteral formulation of rasagiline |
| 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 |
| WO2014110154A1 (en) | 2013-01-08 | 2014-07-17 | Pathologica Llc | Methods and comp0stions for treatment of demyelinating diseases |
| 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
- 2009-06-09 US US12/456,001 patent/US20100189791A1/en not_active Abandoned
- 2009-06-09 US US12/455,976 patent/US8080584B2/en not_active Expired - Fee Related
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