JP2008507566A5 - - Google Patents
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- Publication number
- JP2008507566A5 JP2008507566A5 JP2007522852A JP2007522852A JP2008507566A5 JP 2008507566 A5 JP2008507566 A5 JP 2008507566A5 JP 2007522852 A JP2007522852 A JP 2007522852A JP 2007522852 A JP2007522852 A JP 2007522852A JP 2008507566 A5 JP2008507566 A5 JP 2008507566A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- cinacalcet hydrochloride
- drying
- precipitate
- solution
- 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
- 238000000034 method Methods 0.000 claims 31
- 229960000478 cinacalcet hydrochloride Drugs 0.000 claims 14
- QANQWUQOEJZMLL-PKLMIRHRSA-N cinacalcet hydrochloride Chemical compound Cl.N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 QANQWUQOEJZMLL-PKLMIRHRSA-N 0.000 claims 14
- 238000001035 drying Methods 0.000 claims 9
- 239000002244 precipitate Substances 0.000 claims 9
- 239000002002 slurry Substances 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 5
- 239000012296 anti-solvent Substances 0.000 claims 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 238000005406 washing Methods 0.000 claims 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 229960003315 cinacalcet Drugs 0.000 claims 1
- VDHAWDNDOKGFTD-MRXNPFEDSA-N cinacalcet Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 VDHAWDNDOKGFTD-MRXNPFEDSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical group O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68415205P | 2005-05-23 | 2005-05-23 | |
| US60/684,152 | 2005-05-23 | ||
| US69698105P | 2005-07-05 | 2005-07-05 | |
| US60/696,981 | 2005-07-05 | ||
| US69711105P | 2005-07-06 | 2005-07-06 | |
| US60/697,111 | 2005-07-06 | ||
| US69861305P | 2005-07-11 | 2005-07-11 | |
| US60/698,613 | 2005-07-11 | ||
| US70123205P | 2005-07-20 | 2005-07-20 | |
| US60/701,232 | 2005-07-20 | ||
| US70291805P | 2005-07-26 | 2005-07-26 | |
| US60/702,918 | 2005-07-26 | ||
| US70691005P | 2005-08-09 | 2005-08-09 | |
| US60/706,910 | 2005-08-09 | ||
| US73005005P | 2005-10-24 | 2005-10-24 | |
| US60/730,050 | 2005-10-24 | ||
| US73208305P | 2005-10-31 | 2005-10-31 | |
| US60/732,083 | 2005-10-31 | ||
| US73300805P | 2005-11-02 | 2005-11-02 | |
| US60/733,008 | 2005-11-02 | ||
| US73466905P | 2005-11-07 | 2005-11-07 | |
| US60/734,669 | 2005-11-07 | ||
| US73512605P | 2005-11-08 | 2005-11-08 | |
| US60/735,126 | 2005-11-08 | ||
| US73882705P | 2005-11-21 | 2005-11-21 | |
| US60/738,827 | 2005-11-21 | ||
| US74178705P | 2005-12-01 | 2005-12-01 | |
| US60/741,787 | 2005-12-01 | ||
| US75091005P | 2005-12-15 | 2005-12-15 | |
| US60/750,910 | 2005-12-15 | ||
| US79480406P | 2006-04-24 | 2006-04-24 | |
| US60/794,804 | 2006-04-24 | ||
| PCT/US2006/020304 WO2006127933A1 (en) | 2005-05-23 | 2006-05-23 | Processes for preparing cinacalcet hydrochloride crystal form i |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010197123A Division JP2010280715A (ja) | 2005-05-23 | 2010-09-02 | シナカルセト塩酸塩結晶フォームｉの調製方法 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2008507566A JP2008507566A (ja) | 2008-03-13 |
| JP2008507566A6 JP2008507566A6 (ja) | 2008-07-03 |
| JP2008507566A5 true JP2008507566A5 (enExample) | 2010-03-04 |
| JP4638491B2 JP4638491B2 (ja) | 2011-02-23 |
Family
ID=37101358
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522851A Pending JP2008507565A (ja) | 2005-05-23 | 2006-05-23 | シナカルセトの精製 |
| JP2007522852A Expired - Fee Related JP4638491B2 (ja) | 2005-05-23 | 2006-05-23 | シナカルセト塩酸塩結晶フォームｉの調製方法 |
| JP2010197123A Pending JP2010280715A (ja) | 2005-05-23 | 2010-09-02 | シナカルセト塩酸塩結晶フォームｉの調製方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522851A Pending JP2008507565A (ja) | 2005-05-23 | 2006-05-23 | シナカルセトの精製 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010197123A Pending JP2010280715A (ja) | 2005-05-23 | 2010-09-02 | シナカルセト塩酸塩結晶フォームｉの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7294735B2 (enExample) |
| EP (3) | EP1975150A1 (enExample) |
| JP (3) | JP2008507565A (enExample) |
| KR (2) | KR20070088485A (enExample) |
| CN (1) | CN101180261A (enExample) |
| AT (1) | ATE445587T1 (enExample) |
| CA (2) | CA2606099A1 (enExample) |
| ES (1) | ES2334260T3 (enExample) |
| IL (2) | IL185108A0 (enExample) |
| MX (1) | MX2007000983A (enExample) |
| TW (1) | TW200716512A (enExample) |
| WO (2) | WO2006127932A2 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5309014B2 (ja) * | 2006-03-23 | 2013-10-09 | アムジエン・インコーポレーテツド | シナカルセットの多形体の製造および使用のための方法および組成物 |
| WO2008000422A1 (en) * | 2006-06-27 | 2008-01-03 | Sandoz Ag | Amorphous form of cinacalcet |
| WO2008000423A1 (en) * | 2006-06-27 | 2008-01-03 | Sandoz Ag | Crystalline form of cinacalcet |
| EP1913941A1 (en) * | 2006-10-19 | 2008-04-23 | Sandoz AG | Polymorphic forms and solvates of Cinacalcet hydrochloride |
| EP1945184A2 (en) * | 2006-09-01 | 2008-07-23 | Teva Pharmaceutical Industries Ltd. | Solid composites of a calicum receptor-active compound |
| WO2008058236A2 (en) * | 2006-11-08 | 2008-05-15 | Dr. Reddy's Labortories, Ltd. | Methods for preparing cinacalcet hydrochloride |
| WO2008063645A1 (en) * | 2006-11-20 | 2008-05-29 | Teva Pharmaceutical Industries Ltd. | Process for preparing cinacalcet |
| WO2009002427A2 (en) * | 2007-06-21 | 2008-12-31 | Amgen Inc. | Methods of synthesizing cinacalcet and salts thereof |
| ITMI20071261A1 (it) | 2007-06-22 | 2008-12-23 | Dipharma Francis Srl | Procedimento per la preparazione di cinacalcet |
| US20090093652A1 (en) * | 2007-08-16 | 2009-04-09 | Michal Rafilovich | Crystalline forms cinacalcet fumarate and cinacalcet succinate and processes for preparation thereof |
| CN101932549A (zh) * | 2007-09-18 | 2010-12-29 | 麦迪凯姆股份公司 | 制备西那卡塞盐酸盐的改进方法 |
| US7696372B2 (en) * | 2007-10-01 | 2010-04-13 | Ascenta Therapeutics, Inc. | Process for preparing R-gossypol L-phenylalaninol dienamine |
| US20090275780A1 (en) * | 2008-05-05 | 2009-11-05 | Medichem, S.A. | Process for controlling the particle size of a 3-(trifluoromethyl)phenyl]-1-aminopropane derivative |
| WO2009153814A1 (en) * | 2008-06-18 | 2009-12-23 | Erregierre S.P.A. | A process for the synthesis of cinacalcet hydrochloride |
| EP2328860A2 (en) * | 2008-08-06 | 2011-06-08 | Actavis Group PTC EHF | Unsaturated cinacalcet salts and processes for preparing cinacalcet hydrochloride |
| WO2010067204A1 (en) | 2008-12-08 | 2010-06-17 | Actavis Group Ptc Ehf | Highly pure cinacalcet or a pharmaceutically acceptable salt thereof |
| WO2010094674A2 (en) | 2009-02-19 | 2010-08-26 | Zach System S.P.A. | Process for preparing cinacalcet hydrochloride |
| JP2012519677A (ja) | 2009-03-05 | 2012-08-30 | シプラ・リミテッド | シナカルセト及びその塩の製造方法、並びに該方法に使用する中間体 |
| WO2010128388A2 (en) | 2009-05-08 | 2010-11-11 | Aurobindo Pharma Limited | An improved process for the preparation of intermediate compounds useful for the preparation of cinacalcet |
| JP5685594B2 (ja) | 2009-09-10 | 2015-03-18 | ザック システム エス．ピー．エー．ＺａＣｈ Ｓｙｓｔｅｍ Ｓ．ｐ．Ａ． | シナカルセトの製造方法 |
| US8722732B2 (en) | 2009-09-29 | 2014-05-13 | Nektar Therapeutics | Oligomer-calcimimetic conjugates and related compounds |
| IT1396623B1 (it) | 2009-11-26 | 2012-12-14 | Dipharma Francis Srl | Procedimento per la preparazione di cinacalcet e suoi intermedi |
| CZ303627B6 (cs) * | 2011-11-25 | 2013-01-16 | Zentiva, K.S. | Zpusob výroby Cinacalcetu |
| CN103450027B (zh) | 2012-05-29 | 2015-07-29 | 上海京新生物医药有限公司 | 盐酸西那卡塞的制备方法 |
| FR2995307A1 (fr) | 2012-09-07 | 2014-03-14 | Prod Chim Auxiliaires Et De Synthese | Procede de preparation du cinacalcet et de ses sels pharmaceutiquement acceptables |
| CN103739500B (zh) * | 2012-12-27 | 2016-03-23 | 国药一心制药有限公司 | 一种盐酸西那卡塞的合成与精制方法 |
| CN103193655B (zh) * | 2013-04-15 | 2015-06-24 | 山东新华制药股份有限公司 | 盐酸西那卡塞晶型ⅰ的制备方法 |
| CN104512864B (zh) * | 2013-09-30 | 2017-08-22 | 中国石油化工股份有限公司 | 一种低温脱除微量碳氧化物的方法 |
| EP3068394A4 (en) | 2013-11-15 | 2017-04-26 | Akebia Therapeutics Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino}acetic acid, compositions, and uses thereof |
| BR102015025502B1 (pt) * | 2015-04-30 | 2022-06-21 | Aegerion Pharmaceuticals, Inc | Composição de lomitapida, tablete, produto de lomitapida, métodos para analisar uma composição de amostra de lomitapida e para determinar uma quantidade de uma impureza em uma amostra da composição |
| CN104892428A (zh) * | 2015-06-05 | 2015-09-09 | 南京辰逸生物科技有限公司 | 一种盐酸西那卡塞的制备方法 |
| CN106610404B (zh) * | 2015-10-21 | 2019-01-15 | 华仁药业股份有限公司 | 采用hplc法检测盐酸西那卡塞同分异构体的方法 |
| CN105439818B (zh) * | 2015-12-31 | 2017-11-28 | 苏州汇和药业有限公司 | 一种西那卡塞中间体3‑(3‑三氟甲基苯基)丙醇的合成方法 |
| CN107879939A (zh) * | 2016-09-30 | 2018-04-06 | 上海天慈生物谷生物工程有限公司 | 一种制备 n‑((1r)‑1‑(1‑萘基)乙基)‑3‑(3‑(三氟甲基)苯基)丙‑1‑胺盐酸盐的方法 |
| KR20200022712A (ko) * | 2018-08-23 | 2020-03-04 | 주식회사 오스코텍 | 8-브로모-2-(1-메틸피페리딘-4-일아미노)-4-(4-페녹시페닐아미노)피리도[4,3-d]피리미딘-5(6H)-온 염산염의 결정다형체 및 그 제조방법 |
| CN109096119B (zh) * | 2018-10-29 | 2019-10-25 | 江苏永安制药有限公司 | 一种制备盐酸西那卡塞的方法 |
| CN110041206B (zh) * | 2019-04-29 | 2021-10-19 | 梯尔希（南京）药物研发有限公司 | 一种西那卡塞杂质的制备方法 |
| CN111153832B (zh) * | 2020-01-20 | 2022-02-25 | 广州九植医药科技有限公司 | 一种西那卡塞杂质的制备方法 |
| TW202517274A (zh) * | 2023-06-30 | 2025-05-01 | 韓商鐘根堂股份有限公司 | 化合物之新穎製備方法及新結晶形式 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966988A (en) | 1989-02-17 | 1990-10-30 | Chevron Research Company | Process for preparing acetonitrile 3-trifluoromethyl benzene |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) * | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| CN1312116C (zh) * | 1994-10-21 | 2007-04-25 | Nps药物有限公司 | 钙受体活性化合物 |
| US5648541A (en) * | 1995-09-28 | 1997-07-15 | Nps Pharmaceuticals, Inc. | Chiral reductions of imines leading to the syntheses of optically active amines |
| WO1997041090A1 (en) * | 1996-05-01 | 1997-11-06 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| DK3395338T3 (da) * | 2003-09-12 | 2019-07-22 | Amgen Inc | Hurtigt opløsende formulering af cinacalcet-hcl |
-
2006
- 2006-05-23 JP JP2007522851A patent/JP2008507565A/ja active Pending
- 2006-05-23 US US11/440,246 patent/US7294735B2/en not_active Expired - Fee Related
- 2006-05-23 AT AT06771215T patent/ATE445587T1/de not_active IP Right Cessation
- 2006-05-23 KR KR1020077004036A patent/KR20070088485A/ko not_active Ceased
- 2006-05-23 WO PCT/US2006/020303 patent/WO2006127932A2/en not_active Ceased
- 2006-05-23 ES ES06771215T patent/ES2334260T3/es active Active
- 2006-05-23 EP EP08012814A patent/EP1975150A1/en not_active Withdrawn
- 2006-05-23 CN CNA2006800179392A patent/CN101180261A/zh active Pending
- 2006-05-23 CA CA002606099A patent/CA2606099A1/en not_active Abandoned
- 2006-05-23 US US11/439,570 patent/US7247751B2/en not_active Expired - Fee Related
- 2006-05-23 TW TW095118275A patent/TW200716512A/zh unknown
- 2006-05-23 JP JP2007522852A patent/JP4638491B2/ja not_active Expired - Fee Related
- 2006-05-23 MX MX2007000983A patent/MX2007000983A/es not_active Application Discontinuation
- 2006-05-23 EP EP06771214A patent/EP1805135A2/en not_active Withdrawn
- 2006-05-23 EP EP06771215A patent/EP1883618B1/en not_active Not-in-force
- 2006-05-23 KR KR1020077001966A patent/KR20070083471A/ko not_active Ceased
- 2006-05-23 WO PCT/US2006/020304 patent/WO2006127933A1/en not_active Ceased
- 2006-05-23 CA CA002605736A patent/CA2605736A1/en not_active Abandoned
-
2007
- 2007-08-07 IL IL185108A patent/IL185108A0/en unknown
- 2007-08-23 IL IL185494A patent/IL185494A0/en unknown
-
2010
- 2010-09-02 JP JP2010197123A patent/JP2010280715A/ja active Pending
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