CU24105B1 - Proceso para la preparación del calcobutrol - Google Patents
Proceso para la preparación del calcobutrolInfo
- Publication number
- CU24105B1 CU24105B1 CU2012000072A CU20120072A CU24105B1 CU 24105 B1 CU24105 B1 CU 24105B1 CU 2012000072 A CU2012000072 A CU 2012000072A CU 20120072 A CU20120072 A CU 20120072A CU 24105 B1 CU24105 B1 CU 24105B1
- Authority
- CU
- Cuba
- Prior art keywords
- calcobutrol
- gadobutrol
- complex
- purity
- gadolinium
- Prior art date
Links
- GCLKDXFGQNCFQW-CTHHTMFSSA-L calcium 2-[4,10-bis(carboxylatomethyl)-7-[(2R,3S)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate hydron Chemical compound [H+].[Ca+2].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GCLKDXFGQNCFQW-CTHHTMFSSA-L 0.000 title abstract 5
- 229950006450 calcobutrol Drugs 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 4
- ZPDFIIGFYAHNSK-CTHHTMFSSA-K 2-[4,10-bis(carboxylatomethyl)-7-[(2r,3s)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+) Chemical compound [Gd+3].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 ZPDFIIGFYAHNSK-CTHHTMFSSA-K 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 229960003411 gadobutrol Drugs 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052688 Gadolinium Inorganic materials 0.000 abstract 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- JZNZSKXIEDHOBD-HUUCEWRRSA-N 2-[4,10-bis(carboxymethyl)-7-[(2r,3s)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid Chemical compound OC[C@@H](O)[C@@H](CO)N1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 JZNZSKXIEDHOBD-HUUCEWRRSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- ZPDFIIGFYAHNSK-UHFFFAOYSA-K gadobutrol Chemical compound [Gd+3].OCC(O)C(CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 ZPDFIIGFYAHNSK-UHFFFAOYSA-K 0.000 abstract 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/04—Calcium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
Se describe un proceso para la preparación del complejo con calcio del ácido 0-(2,3-Dihidroxi-1-(hidroximetil)propil)-1,4,7,10-tetraazaciclodecano-1,4,7-triacético, que también se conoce como calcobutrol, a partir del correspondiente complejo con gadolinio (Gadobutrol) puro. El gadolinio es eliminado del complejo Gadobutrol por descomplejación con una solución de ácido oxálico dihidratado en agua para obtener el ligando (butrol) con una alta pureza, que subsiguientemente se compleja con una solución acuosa de oxalato de calcio. Finalmente, el calcobutrol obtenido se cristaliza de etanol. El proceso conforme a la presente invención permite obtener Calcobutrol con una calidad muy alta, es decir, muy puro con el mayor rendimiento posible, y en forma cristalina. Este producto es incoloro y soluble en agua y tiene una pureza de 99,0% o más, en algunos lotes del 99,4% o más (pureza de acuerdo con HPLC, método 100%). El proceso completo, desde el Gadobutrol hasta el Calcobutrol se caracteriza por ser altamente reproducible y factible. El rendimiento total de 91,2% es muy bueno. El producto es estable ante el almacenamiento y se puede utilizar para la formulación de soluciones Gadovist.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009053171A DE102009053171B4 (de) | 2009-11-04 | 2009-11-04 | Verfahren zur Herstellung des Calcium-Komplexes von Dihydroxy-hydroxy-methylpropyl-tetraazacyclododecan-triessigsäure (Calcobutrol) |
| PCT/EP2010/066655 WO2011054827A1 (en) | 2009-11-04 | 2010-11-02 | Process for the preparation of calcobutrol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CU20120072A7 CU20120072A7 (es) | 2012-10-15 |
| CU24105B1 true CU24105B1 (es) | 2015-07-30 |
Family
ID=43297060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU2012000072A CU24105B1 (es) | 2009-11-04 | 2010-11-02 | Proceso para la preparación del calcobutrol |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US9447053B2 (es) |
| EP (2) | EP2496562B1 (es) |
| JP (1) | JP5733800B2 (es) |
| KR (3) | KR20120093388A (es) |
| CN (1) | CN102164901B (es) |
| AR (1) | AR078906A1 (es) |
| AU (1) | AU2010317166C1 (es) |
| BR (1) | BR112012010320B1 (es) |
| CA (1) | CA2777314C (es) |
| CL (1) | CL2012001172A1 (es) |
| CO (1) | CO6551758A2 (es) |
| CR (1) | CR20120235A (es) |
| CU (1) | CU24105B1 (es) |
| CY (1) | CY1115051T1 (es) |
| DE (1) | DE102009053171B4 (es) |
| DK (1) | DK2496562T3 (es) |
| DO (1) | DOP2012000126A (es) |
| EA (2) | EA201300789A1 (es) |
| EC (1) | ECSP12011866A (es) |
| ES (1) | ES2462970T3 (es) |
| HR (1) | HRP20140399T1 (es) |
| IL (1) | IL219012A0 (es) |
| MX (1) | MX2012005283A (es) |
| MY (1) | MY158421A (es) |
| NZ (2) | NZ599705A (es) |
| PE (1) | PE20130224A1 (es) |
| PH (1) | PH12012500891A1 (es) |
| PL (1) | PL2496562T3 (es) |
| PT (1) | PT2496562E (es) |
| RS (1) | RS53287B (es) |
| SI (1) | SI2496562T1 (es) |
| TW (1) | TWI473794B (es) |
| UY (1) | UY33002A (es) |
| WO (1) | WO2011054827A1 (es) |
| ZA (1) | ZA201202504B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2780599T3 (es) | 2011-04-21 | 2020-08-26 | Bayer Ip Gmbh | Preparación de gadobutrol de alta pureza |
| EP2786768A1 (en) | 2013-04-04 | 2014-10-08 | Agfa Healthcare | Process for preparing a material comprising a macrocyclic ligand and for producing a pharmaceutical formulation comprising said ligand with a lanthanide |
| KR101693400B1 (ko) | 2014-09-17 | 2017-01-05 | 에스티팜 주식회사 | 칼코부트롤의 제조방법 |
| KR101646211B1 (ko) * | 2014-11-12 | 2016-08-05 | (주)디아이테크 | 자기공명영상용 조영제의 제조방법 |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| CN105037288B (zh) * | 2015-07-23 | 2017-11-03 | 上海现代制药海门有限公司 | 一种布醇的制备方法 |
| CN106620726B (zh) * | 2015-10-29 | 2020-10-02 | 山东威智百科药业有限公司 | 一种钆布醇注射液及其制备方法 |
| CN106187930B (zh) * | 2016-07-12 | 2018-10-19 | 嘉实（湖南）医药科技有限公司 | 高纯度考布曲钙的制备方法 |
| HUE050553T2 (hu) * | 2016-09-27 | 2020-12-28 | Bayer Pharma AG | Eljárás A módosulatú kalkobutrol kristályos alakjának elõállítására |
| WO2018096082A1 (en) | 2016-11-28 | 2018-05-31 | Bayer Pharma Aktiengesellschaft | High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging |
| CN109384737A (zh) * | 2017-08-04 | 2019-02-26 | 天津科伦药物研究有限公司 | 一种四氮杂环钇络合物及其制备方法和应用 |
| KR101971435B1 (ko) * | 2017-08-29 | 2019-04-24 | 주식회사 엔지켐생명과학 | 가도부트롤 중간체 및 이를 이용한 가도부트롤의 제조 방법 |
| KR20190088793A (ko) * | 2018-01-19 | 2019-07-29 | 주식회사 엔지켐생명과학 | 칼코부트롤의 제조방법 |
| EP3820853A4 (en) | 2018-07-10 | 2022-08-17 | Biophore India Pharmaceuticals Pvt. Ltd. | PROCESS FOR THE PREPARATION OF 2,2',2''-(10-((2R,3S)-1,3,4-TRIHYDROXY BUTAN-2-YL)-1,4,7,10-TETRAAZACYCLODODECANE-1 ACID ,4,7-TRIYL) TRIACETIC AND ITS COMPLEXES |
| WO2020084504A1 (en) * | 2018-10-24 | 2020-04-30 | Biophore India Pharmaceuticals Pvt. Ltd | Novel process for the preparation of macrocyclic chelant 2,2',2''-(10-(2-hydroxypropyl)-1,4,7,10-tetra azacyclododecane-1,4,7-triyl) triacetic acid and it's complexes with paramagnetic metal ions |
| AU2019382881B2 (en) * | 2018-11-23 | 2025-06-12 | Bayer Aktiengesellschaft | Formulation of contrast media and process of preparation thereof |
| KR101979836B1 (ko) * | 2019-01-02 | 2019-05-21 | 동국생명과학 주식회사 | 칼코부트롤의 제조방법 |
| CN111039885B (zh) * | 2019-12-06 | 2021-03-05 | 广州康瑞泰药业有限公司 | 一种制备高纯度考布曲钙的方法 |
| US11667601B2 (en) | 2019-12-20 | 2023-06-06 | Bracco Imaging S.P.A. | Calcium BOPTA complex |
| KR20210112910A (ko) | 2020-03-06 | 2021-09-15 | 주식회사 엔지켐생명과학 | 가도부트롤 주사제 제조를 위한 부형제인 칼코부트롤의 제조 방법 |
| KR20210114742A (ko) * | 2020-03-11 | 2021-09-24 | 주식회사 엔지켐생명과학 | 칼테리돌의 제조방법 |
| CN114573522A (zh) * | 2020-11-30 | 2022-06-03 | 江苏恒瑞医药股份有限公司 | 一种考布曲钙的新晶型及其制备方法 |
| CN115779105B (zh) * | 2022-11-17 | 2025-05-27 | 华润双鹤药业股份有限公司 | 一种钆布醇注射液及其制备方法 |
| CN119143689B (zh) * | 2024-11-15 | 2025-05-30 | 苏州美诺医药科技有限公司 | 考布曲钙和其中间体的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3625417C2 (de) | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecan-Derivate |
| DE3640708C2 (de) * | 1986-11-28 | 1995-05-18 | Schering Ag | Verbesserte metallhaltige Pharmazeutika |
| DE4009119A1 (de) | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| IE910955A1 (en) | 1990-03-23 | 1991-09-25 | Yamanouchi Europ Bv | Il-6 inhibiting compositions |
| DE4237943C2 (de) * | 1992-11-06 | 1997-10-23 | Schering Ag | Verfahren zur Herstellung von Metallkomplexen der N-beta-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,7,10-tetraazacyclododecan- und N-beta-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivate |
| DE4218744C2 (de) * | 1992-06-04 | 1997-11-06 | Schering Ag | Verfahren zur Herstellung von N-ß-Hxdroxyalkyl-tri-N-carboxylalkyl-1,4,7,10-tetraazacyclododecan- und N-ß-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivaten und deren Metallkomplexe |
| IT1275426B (it) | 1995-05-16 | 1997-08-07 | Bracco Spa | Recupero del gadolinio e dei suoi agenti complessanti da soluzioni acquose contenenti i loro complessi |
| DE19724186C2 (de) * | 1997-06-02 | 2002-07-18 | Schering Ag | Verfahren zur Mono- und 1,7-Bis-N-ß-Hydroxyalkylierung von Cyclen und die entsprechenden N-ß-Hydroxyalkyl-1,4,7,10-tetraazacyclododecan-Li-Salz-Komplexe |
| IT1292130B1 (it) | 1997-06-11 | 1999-01-25 | Bracco Spa | Processo per la preparazione dell'acido 1,4,7,10-tetraazaciclododecan -1,4,7-triacetico e suoi derivati |
| IT1293778B1 (it) | 1997-07-25 | 1999-03-10 | Bracco Spa | 1,4,7,10-tetraazabiciclo(8.2.2.)tetradecan-2 one, sua preparazione e suo uso per la preparazione di tetraazamacrocicli |
| US9016221B2 (en) * | 2004-02-17 | 2015-04-28 | University Of Florida Research Foundation, Inc. | Surface topographies for non-toxic bioadhesion control |
| WO2011054480A1 (de) * | 2009-11-09 | 2011-05-12 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrolherstellung mittels keramischer membran |
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2009
- 2009-11-04 DE DE102009053171A patent/DE102009053171B4/de active Active
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2010
- 2010-11-02 SI SI201030597T patent/SI2496562T1/sl unknown
- 2010-11-02 CA CA2777314A patent/CA2777314C/en active Active
- 2010-11-02 NZ NZ599705A patent/NZ599705A/en unknown
- 2010-11-02 AU AU2010317166A patent/AU2010317166C1/en active Active
- 2010-11-02 RS RS20140225A patent/RS53287B/sr unknown
- 2010-11-02 JP JP2012537372A patent/JP5733800B2/ja active Active
- 2010-11-02 CU CU2012000072A patent/CU24105B1/es active IP Right Grant
- 2010-11-02 BR BR112012010320-2A patent/BR112012010320B1/pt active IP Right Grant
- 2010-11-02 KR KR1020127015861A patent/KR20120093388A/ko not_active Withdrawn
- 2010-11-02 EP EP10774202.5A patent/EP2496562B1/en active Active
- 2010-11-02 PE PE2012000612A patent/PE20130224A1/es active IP Right Grant
- 2010-11-02 KR KR1020117016891A patent/KR101251210B1/ko not_active Ceased
- 2010-11-02 EA EA201300789A patent/EA201300789A1/ru unknown
- 2010-11-02 ES ES10774202.5T patent/ES2462970T3/es active Active
- 2010-11-02 PL PL10774202T patent/PL2496562T3/pl unknown
- 2010-11-02 PH PH1/2012/500891A patent/PH12012500891A1/en unknown
- 2010-11-02 MY MYPI2012001942A patent/MY158421A/en unknown
- 2010-11-02 DK DK10774202.5T patent/DK2496562T3/da active
- 2010-11-02 PT PT107742025T patent/PT2496562E/pt unknown
- 2010-11-02 EP EP13151283.2A patent/EP2599777A1/en not_active Withdrawn
- 2010-11-02 KR KR1020107029604A patent/KR101057939B1/ko active Active
- 2010-11-02 WO PCT/EP2010/066655 patent/WO2011054827A1/en not_active Ceased
- 2010-11-02 CN CN201080002019.XA patent/CN102164901B/zh active Active
- 2010-11-02 NZ NZ612449A patent/NZ612449A/en unknown
- 2010-11-02 MX MX2012005283A patent/MX2012005283A/es active IP Right Grant
- 2010-11-02 US US13/508,198 patent/US9447053B2/en active Active
- 2010-11-02 EA EA201200652A patent/EA020161B9/ru not_active IP Right Cessation
- 2010-11-02 HR HRP20140399AT patent/HRP20140399T1/hr unknown
- 2010-11-04 TW TW99137984A patent/TWI473794B/zh active
- 2010-11-04 AR ARP100104075A patent/AR078906A1/es active IP Right Grant
- 2010-11-04 UY UY0001033002A patent/UY33002A/es not_active Application Discontinuation
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2012
- 2012-04-03 IL IL219012A patent/IL219012A0/en active IP Right Grant
- 2012-04-05 ZA ZA2012/02504A patent/ZA201202504B/en unknown
- 2012-05-04 CR CR20120235A patent/CR20120235A/es unknown
- 2012-05-04 CL CL2012001172A patent/CL2012001172A1/es unknown
- 2012-05-04 CO CO12073057A patent/CO6551758A2/es not_active Application Discontinuation
- 2012-05-04 DO DO2012000126A patent/DOP2012000126A/es unknown
- 2012-05-04 EC ECSP12011866 patent/ECSP12011866A/es unknown
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2014
- 2014-05-07 CY CY20141100325T patent/CY1115051T1/el unknown
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