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 |
|---|---|---|---|
| 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 |
| JP2007522851A Pending JP2008507565A (ja) | 2005-05-23 | 2006-05-23 | シナカルセトの精製 |
| 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 After (2)
| 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 |
| 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) | EP1883618B1 (enExample) |
| JP (3) | JP4638491B2 (enExample) |
| KR (2) | KR20070088485A (enExample) |
| CN (1) | CN101180261A (enExample) |
| AT (1) | ATE445587T1 (enExample) |
| CA (2) | CA2605736A1 (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 |
|---|---|---|---|---|
| CA2645494C (en) * | 2006-03-23 | 2016-01-12 | Amgen Inc. | Methods and compositions for making and using polymorphs of cinacalcet |
| EP1913941A1 (en) * | 2006-10-19 | 2008-04-23 | Sandoz AG | Polymorphic forms and solvates of Cinacalcet hydrochloride |
| US20090258949A1 (en) * | 2006-06-27 | 2009-10-15 | Johannes Ludescher | Amorphous form of cinacalcet |
| WO2008000423A1 (en) * | 2006-06-27 | 2008-01-03 | Sandoz Ag | Crystalline form of cinacalcet |
| US20080181959A1 (en) * | 2006-09-01 | 2008-07-31 | Ilan Zalit | Solid composites of a calcium 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 |
| CA2691196C (en) * | 2007-06-21 | 2016-05-24 | 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 |
| WO2009039241A2 (en) * | 2007-09-18 | 2009-03-26 | Medichem, S.A. | Improved process for preparing cinacalcet hydrochloride |
| US7696372B2 (en) * | 2007-10-01 | 2010-04-13 | Ascenta Therapeutics, Inc. | Process for preparing R-gossypol L-phenylalaninol dienamine |
| US20110189241A1 (en) * | 2008-05-05 | 2011-08-04 | Medichem, S.A. | Process For Controlling The Particle Size of A [3-(Trifluoromethyl)Phenyl]-1-Aminopropane Derivative |
| EP2321256B1 (en) * | 2008-06-18 | 2014-11-12 | ERREGIERRE S.p.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 |
| US20110318417A1 (en) * | 2008-12-08 | 2011-12-29 | Actavis Group Ptc Ehf | Highly pure cinacalcet or a pharmaceutically acceptable salt thereof |
| EP2398763A2 (en) | 2009-02-19 | 2011-12-28 | ZaCh System S.p.A. | Process for preparing cinacalcet hydrochloride |
| US8575393B2 (en) | 2009-03-05 | 2013-11-05 | Cipla Limited | Process for the preparation of cinacalcet and salts thereof, and intermediates for use in the process |
| 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 |
| CN102548955B (zh) | 2009-09-10 | 2014-06-04 | Zach系统股份公司 | 用于制备西那卡塞特的方法 |
| 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 |
| CZ2011770A3 (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 |
| AU2014348523B2 (en) | 2013-11-15 | 2019-01-03 | 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 |
| KR20250003360A (ko) * | 2023-06-30 | 2025-01-07 | 주식회사 종근당 | 화합물의 신규한 제조방법 및 신규한 결정형 |
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 |
| 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 |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| HU228150B1 (en) * | 1994-10-21 | 2012-12-28 | Nps Pharma Inc | Calcium receptor-active compounds, medicaments comprising them, and the use of said medicaments |
| US5648541A (en) * | 1995-09-28 | 1997-07-15 | Nps Pharmaceuticals, Inc. | Chiral reductions of imines leading to the syntheses of optically active amines |
| EP0907631B1 (en) * | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| US7829595B2 (en) * | 2003-09-12 | 2010-11-09 | Amgen Inc. | Rapid dissolution formulation of a calcium receptor-active compound |
-
2006
- 2006-05-23 EP EP06771215A patent/EP1883618B1/en not_active Not-in-force
- 2006-05-23 ES ES06771215T patent/ES2334260T3/es active Active
- 2006-05-23 US US11/440,246 patent/US7294735B2/en not_active Expired - Fee Related
- 2006-05-23 CA CA002605736A patent/CA2605736A1/en not_active Abandoned
- 2006-05-23 AT AT06771215T patent/ATE445587T1/de not_active IP Right Cessation
- 2006-05-23 EP EP06771214A patent/EP1805135A2/en not_active Withdrawn
- 2006-05-23 JP JP2007522852A patent/JP4638491B2/ja not_active Expired - Fee Related
- 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 EP EP08012814A patent/EP1975150A1/en not_active Withdrawn
- 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 KR KR1020077001966A patent/KR20070083471A/ko not_active Ceased
- 2006-05-23 WO PCT/US2006/020304 patent/WO2006127933A1/en not_active Ceased
- 2006-05-23 MX MX2007000983A patent/MX2007000983A/es not_active Application Discontinuation
- 2006-05-23 JP JP2007522851A patent/JP2008507565A/ja active Pending
- 2006-05-23 TW TW095118275A patent/TW200716512A/zh unknown
- 2006-05-23 CN CNA2006800179392A patent/CN101180261A/zh active Pending
-
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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