JP2012508178A5 - - Google Patents
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- Publication number
- JP2012508178A5 JP2012508178A5 JP2011534915A JP2011534915A JP2012508178A5 JP 2012508178 A5 JP2012508178 A5 JP 2012508178A5 JP 2011534915 A JP2011534915 A JP 2011534915A JP 2011534915 A JP2011534915 A JP 2011534915A JP 2012508178 A5 JP2012508178 A5 JP 2012508178A5
- Authority
- JP
- Japan
- Prior art keywords
- nilotinib hcl
- degrees
- crystalline
- powder
- ray diffraction
- 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
- VTGGYCCJUPYZSX-UHFFFAOYSA-N 4-methyl-n-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide;hydrochloride Chemical compound Cl.C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 VTGGYCCJUPYZSX-UHFFFAOYSA-N 0.000 claims description 90
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 20
- 239000002002 slurry Substances 0.000 claims description 12
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005536 L01XE08 - Nilotinib Substances 0.000 claims description 5
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 claims description 5
- 229960001346 nilotinib Drugs 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 3
- 239000012453 solvate Substances 0.000 description 1
Applications Claiming Priority (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11156108P | 2008-11-05 | 2008-11-05 | |
| US61/111,561 | 2008-11-05 | ||
| US15578909P | 2009-02-26 | 2009-02-26 | |
| US61/155,789 | 2009-02-26 | ||
| US17745409P | 2009-05-12 | 2009-05-12 | |
| US61/177,454 | 2009-05-12 | ||
| US22721009P | 2009-07-21 | 2009-07-21 | |
| US61/227,210 | 2009-07-21 | ||
| US24070909P | 2009-09-09 | 2009-09-09 | |
| US61/240,709 | 2009-09-09 | ||
| US24251409P | 2009-09-15 | 2009-09-15 | |
| US61/242,514 | 2009-09-15 | ||
| US24679909P | 2009-09-29 | 2009-09-29 | |
| US61/246,799 | 2009-09-29 | ||
| US24937609P | 2009-10-07 | 2009-10-07 | |
| US61/249,376 | 2009-10-07 | ||
| PCT/US2009/063365 WO2010054056A2 (en) | 2008-11-05 | 2009-11-05 | Nilotinib hci crystalline forms |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012508178A JP2012508178A (ja) | 2012-04-05 |
| JP2012508178A5 true JP2012508178A5 (enExample) | 2012-12-20 |
| JP5486012B2 JP5486012B2 (ja) | 2014-05-07 |
Family
ID=41666779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011534915A Active JP5486012B2 (ja) | 2008-11-05 | 2009-11-05 | ニロチニブＨＣｌ結晶形 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8227477B2 (enExample) |
| EP (2) | EP2262793B1 (enExample) |
| JP (1) | JP5486012B2 (enExample) |
| KR (2) | KR20120111743A (enExample) |
| CN (1) | CN102203084B (enExample) |
| CA (1) | CA2740794A1 (enExample) |
| DK (1) | DK2262793T3 (enExample) |
| ES (1) | ES2394258T3 (enExample) |
| HR (1) | HRP20120793T1 (enExample) |
| PL (1) | PL2262793T3 (enExample) |
| TW (1) | TW201022240A (enExample) |
| WO (1) | WO2010054056A2 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN2010KO00035A (enExample) * | 2010-01-15 | 2016-09-02 | ||
| WO2011133675A1 (en) * | 2010-04-21 | 2011-10-27 | Teva Pharmaceutical Industries Ltd. | Gabapentin enacarbil compositions |
| CN103038227A (zh) * | 2010-06-21 | 2013-04-10 | 特瓦制药工业有限公司 | 尼洛替尼盐及其晶形 |
| EP2966072A3 (en) | 2010-06-21 | 2016-02-24 | Teva Pharmaceutical Industries, Ltd. | Crystalline forms of nilotinib hydrobromide, succinate, glutamate, acetate, l-malate and maleate |
| CN102453024B (zh) * | 2010-10-27 | 2014-09-03 | 浙江九洲药业股份有限公司 | 一种尼罗替尼盐酸盐晶型及其制备方法 |
| IN2010CH03577A (enExample) * | 2010-11-26 | 2012-07-20 | Hetero Research Foundation | |
| WO2012164578A1 (en) * | 2011-06-02 | 2012-12-06 | Hetero Research Foundation | Compositions and methods for preparing immediate release formulations of nilotinib |
| AR086913A1 (es) * | 2011-06-14 | 2014-01-29 | Novartis Ag | 4-metil-3-[[4-(3-piridinil)-2-pirimidinil]-amino]-n-[5-(4-metil-1h-imidazol-1-il)-3-(trifluoro-metil)-fenil]-benzamida amorfa, forma de dosificacion que la contiene y metodo para prepararlas |
| EP2626355B1 (en) * | 2012-02-09 | 2016-02-03 | Natco Pharma Limited | Process for the preparation of nilotinib hydrochloride |
| US9061028B2 (en) | 2012-02-15 | 2015-06-23 | Natco Pharma Limited | Process for the preparation of Nilotinib |
| WO2014059518A1 (en) * | 2012-10-15 | 2014-04-24 | Apotex Technologies Inc. | Solid forms of nilotinib hydrochloride |
| EP2909191B1 (en) | 2012-10-19 | 2019-03-20 | Basf Se | Multicomponent crystalline system comprising nilotinib and selected co-crystal formers |
| AU2014259029B2 (en) * | 2013-04-24 | 2018-08-16 | Dr. Reddys Laboratories Limited | Polymorphic forms of nilotinib hydrochloride |
| US9636340B2 (en) | 2013-11-12 | 2017-05-02 | Ayyappan K. Rajasekaran | Kinase inhibitors |
| WO2015092624A1 (en) | 2013-12-16 | 2015-06-25 | Ranbaxy Laboratories Limited | Nilotinib mono-oxalate and its crystalline form |
| WO2016020891A1 (en) | 2014-08-08 | 2016-02-11 | Dr. Reddy’S Laboratories Limited | Process for the preparation of polymorphic forms of nilotinib |
| MX2017004770A (es) | 2014-10-16 | 2017-07-26 | Apotex Inc | Formas solidas del clorhidrato de nilotinib. |
| CN106478603B (zh) * | 2015-08-25 | 2021-01-01 | 江苏豪森药业集团有限公司 | 尼洛替尼盐酸盐的新晶型及其制备方法和医药用途 |
| WO2017064538A1 (en) * | 2015-10-16 | 2017-04-20 | Nobel Ilac Sanayii Ve Ticaret A.S. | Pharmaceutical compositions of nilotinib hydrochloride |
| WO2017129694A1 (en) | 2016-01-26 | 2017-08-03 | Farma Grs, D.O.O. | Nilotinib dinitrate (v) and crystalline forms thereof |
| US10640487B2 (en) | 2016-03-14 | 2020-05-05 | Teva Pharmaceuticals Usa, Inc. | Solid state forms of Nilotinib salts |
| EP3404025B1 (en) * | 2017-05-16 | 2019-12-04 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Process for the preparation of pure nilotinib and its salt |
| CZ2017821A3 (cs) | 2017-12-20 | 2019-07-03 | Zentiva, K.S. | Léková forma obsahující krystalický nilotinib |
| CN115192540A (zh) | 2018-06-15 | 2022-10-18 | 汉达癌症医药责任有限公司 | 激酶抑制剂的盐类及其组合物 |
| WO2020095187A1 (en) * | 2018-11-05 | 2020-05-14 | Laurus Labs Limited | Crystalline form of nilotinib hydrochloride, process for its preparation and pharmaceutical composition containing the same |
| US20240316044A1 (en) | 2021-06-19 | 2024-09-26 | Helm Ag | Granulate composition comprising nilotinib |
| EP4122452A1 (en) | 2021-07-23 | 2023-01-25 | KRKA, d.d., Novo mesto | Pharmaceutical composition comprising nilotinib and method of manufacturing the same |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| GB0325031D0 (en) | 2003-10-27 | 2003-12-03 | Novartis Ag | Organic compounds |
| MY146795A (en) | 2005-06-09 | 2012-09-28 | Novartis Ag | Process for the synthesis of organic compounds |
| SA06270147B1 (ar) | 2005-06-09 | 2009-12-22 | نوفارتيس ايه جي | عملية لتخليق 5-(مثيل–1h–إيميدازول–1-يل )–3-(ثلاثي فلـورو مثيل)–بنزامـين |
| GT200600315A (es) * | 2005-07-20 | 2007-03-19 | Formas cristalinas de 4-metilo-n-[3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo]-3-(4-pyridina-3-ilo-pirimidina-2-iloamino)-benzamida | |
| GT200600316A (es) * | 2005-07-20 | 2007-04-02 | Sales de 4-metilo-n-(3-(4-metilo-imidazol-1-ilo)-5-trifluorometilo-fenilo)-3-(4-piridina-3-ilo-pirimidina-2-iloamino)- benzamida. | |
| CN101228150B (zh) * | 2005-07-20 | 2014-10-15 | 诺华股份有限公司 | 4-甲基-n-[3-(4-甲基-咪唑-1-基)-5-三氟甲基-苯基]-3-(4-吡啶-3-基-嘧啶-2-基氨基)-苯甲酰胺的晶形 |
| FR2889524B1 (fr) | 2005-08-05 | 2008-08-29 | Rhodia Chimie Sas | Procede de formation d'une liaison carbone-azote |
| KR100674813B1 (ko) | 2005-08-05 | 2007-01-29 | 일양약품주식회사 | Ｎ-페닐-2-피리미딘-아민 유도체 및 그의 제조방법 |
| US20100016590A1 (en) * | 2008-07-17 | 2010-01-21 | Teva Pharmaceutical Industries Ltd. | Nilotinib intermediates and preparation thereof |
-
2009
- 2009-11-05 CN CN200980144606.XA patent/CN102203084B/zh active Active
- 2009-11-05 KR KR1020127021115A patent/KR20120111743A/ko not_active Ceased
- 2009-11-05 PL PL09752057T patent/PL2262793T3/pl unknown
- 2009-11-05 DK DK09752057.1T patent/DK2262793T3/da active
- 2009-11-05 KR KR1020107014884A patent/KR101251726B1/ko active Active
- 2009-11-05 EP EP09752057A patent/EP2262793B1/en not_active Revoked
- 2009-11-05 US US12/612,943 patent/US8227477B2/en active Active
- 2009-11-05 TW TW098137645A patent/TW201022240A/zh unknown
- 2009-11-05 JP JP2011534915A patent/JP5486012B2/ja active Active
- 2009-11-05 CA CA2740794A patent/CA2740794A1/en not_active Abandoned
- 2009-11-05 ES ES09752057T patent/ES2394258T3/es active Active
- 2009-11-05 WO PCT/US2009/063365 patent/WO2010054056A2/en not_active Ceased
- 2009-11-05 EP EP12182091.4A patent/EP2530081A3/en not_active Withdrawn
- 2009-11-05 HR HRP20120793AT patent/HRP20120793T1/hr unknown
-
2012
- 2012-06-27 US US13/535,105 patent/US8592442B2/en not_active Expired - Fee Related