HRP20200922T1 - Postupak za proizvodnju kristalnog oblika modifikacije a kalkobutrola - Google Patents
Postupak za proizvodnju kristalnog oblika modifikacije a kalkobutrola Download PDFInfo
- Publication number
- HRP20200922T1 HRP20200922T1 HRP20200922TT HRP20200922T HRP20200922T1 HR P20200922 T1 HRP20200922 T1 HR P20200922T1 HR P20200922T T HRP20200922T T HR P20200922TT HR P20200922 T HRP20200922 T HR P20200922T HR P20200922 T1 HRP20200922 T1 HR P20200922T1
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- HR
- Croatia
- Prior art keywords
- compound
- formula
- production
- solution
- water
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 6
- 230000004048 modification Effects 0.000 title claims 2
- 238000012986 modification Methods 0.000 title claims 2
- 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 1
- 229950006450 calcobutrol Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 4
- 150000002500 ions Chemical class 0.000 claims 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 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 238000010668 complexation reaction Methods 0.000 claims 3
- 229960003411 gadobutrol Drugs 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 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 claims 2
- SXNRJXPFKZHLFP-UHFFFAOYSA-N 2-[4,5-bis(carboxymethyl)-1,12-dihydroxy-2-(hydroxymethyl)-3-propyl-1,2,3,4-tetrazacyclododec-5-yl]acetic acid Chemical compound CCCN1N(CO)N(O)C(O)CCCCCCC(CC(O)=O)(CC(O)=O)N1CC(O)=O SXNRJXPFKZHLFP-UHFFFAOYSA-N 0.000 claims 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 150000000921 Gadolinium Chemical class 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 239000003637 basic solution Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- SQORATIMOBOFKR-UHFFFAOYSA-H gadolinium(3+);oxalate Chemical compound [Gd+3].[Gd+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O SQORATIMOBOFKR-UHFFFAOYSA-H 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000004682 monohydrates Chemical group 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
- A61K49/10—Organic compounds
- A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
- A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
- A61K49/108—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA the metal complex being Gd-DOTA
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Radiology & Medical Imaging (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (10)
1. Spoj s formulom (I) u kristalnom obliku modifikacije A
[image]
naznačen time što dijagram rendgenske difrakcije praška spoja pokazuje vrhove maksimuma kuta 2-theta na 7,6°, 9,1°, 11,1°, 11,3°, 11,9° i 12,3°.
2. Spoj s formulom (I) prema patentnom zahtjevu 1, naznačen time što je monohidrat s 2,0 – 2,5 masenih % etanola.
3. Postupak za proizvodnju spoja s formulom (I) prema patentnom zahtjevu 1 ili 2, naznačen time što se dekompleksira gadolinijev kompleks dihidroksi-hidroksi-metilpropil-tetraazaciklododekan-trioctene kiseline (gadobutrol), istaložena gadolinijeva sol se uklanja, zatim se otopina sa slobodnim ligandima veže na kiseli ionski izmjenjivač, zatim se eluira s vodenom baznom otopinom, zatim se kompleksira s kalcij2+ ionima, zatim se stehiometrija Ca:butrol prilagođava na 1:1, zatim se provodi kristalizacija iz vodene otopine etanola s udjelom vode od 9 - 11 masenih % vode i zatim se proizvod suši, te se tako izolira spoj s formulom (I) prema patentnom zahtjevu 1 ili 2.
4. Postupak za proizvodnju spoja s formulom (I) prema patentnom zahtjevu 1 ili 2, naznačen time što se gadolinijev kompleks dihidroksi-hidroksi-metilpropil- tetraazaciklododekan-trioctene kiseline (gadobutrol) dekompleksira s oksalnom kiselinom u vodi uz zagrijavanje, istaloženi gadolinijev oksalat se odfiltrira, zatim se slobodni ligand veže na kiseli ionski izmjenjivač, zatim se eluira vodenom otopinom amonijaka, te se nakon koncentriranja otopina kompleksira s kalcij2+ ionima, zatim se stehiometrija Ca:butrol prilagođava na 1:1, zatim se zagrijava pod refluksom iz vodenog etanola s udjelom vode od 9 - 11 masenih % vode, zatim se hladi, nakon izolacije se suši, te se tako izolira spoj s formulom (I) prema patentnom zahtjevu 1 ili 2.
5. Postupak za proizvodnju spoja s formulom (I) prema patentnom zahtjevu 3 ili 4, naznačen time što se za kompleksiranje upotrebljava kalcijev karbonat.
6. Postupak za proizvodnju spoja s formulom (I) prema patentnom zahtjevu 3, 4 ili 5, naznačen time što se za kompleksiranje upotrebljava kalcijev karbonat i što se kompleksiranje provodi u temperaturnom rasponu od ≥ 20 °C i ≤ 25 °C.
7. Spoj s formulom (I) prema patentnim zahtjevima 1 ili 2, naznačen time što je proizveden jednim od postupaka prema jednom od zahtjeva 3, 4, 5 ili 6.
8. Spoj s formulom (I) prema patentnim zahtjevima 1 ili 2 s čistoćom od ≥ 99,0%.
9. Spoj s formulom (I) prema patentnim zahtjevima 1 ili 2 s čistoćom od ≥ 99,7%.
10. Uporaba spoja s formulom (I) prema jednom od zahtjeva 1, 2, 7, 8 ili 9 naznačena time što je za proizvodnju galenskih formulacija gadobutrola.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16190812 | 2016-09-27 | ||
| EP17768733.2A EP3519394B1 (en) | 2016-09-27 | 2017-09-11 | Method for producing the crystalline form of modification a of calcobutrol |
| PCT/EP2017/072683 WO2018059914A1 (en) | 2016-09-27 | 2017-09-11 | Method for producing the crystalline form of modification a of calcobutrol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20200922T1 true HRP20200922T1 (hr) | 2020-09-18 |
Family
ID=57003447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20200922TT HRP20200922T1 (hr) | 2016-09-27 | 2020-06-09 | Postupak za proizvodnju kristalnog oblika modifikacije a kalkobutrola |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US10793532B2 (hr) |
| EP (1) | EP3519394B1 (hr) |
| JP (2) | JP7053590B2 (hr) |
| KR (1) | KR102395523B1 (hr) |
| CN (1) | CN109803958B (hr) |
| AR (1) | AR109729A1 (hr) |
| AU (1) | AU2017333698B2 (hr) |
| BR (1) | BR112019006066A2 (hr) |
| CA (1) | CA3038036C (hr) |
| CY (1) | CY1123317T1 (hr) |
| DK (1) | DK3519394T3 (hr) |
| ES (1) | ES2809736T3 (hr) |
| HR (1) | HRP20200922T1 (hr) |
| HU (1) | HUE050553T2 (hr) |
| IL (1) | IL265536B (hr) |
| LT (1) | LT3519394T (hr) |
| MX (1) | MX2019003540A (hr) |
| NZ (1) | NZ751256A (hr) |
| PL (1) | PL3519394T3 (hr) |
| PT (1) | PT3519394T (hr) |
| RS (1) | RS60392B1 (hr) |
| SG (1) | SG11201901460UA (hr) |
| SI (1) | SI3519394T1 (hr) |
| TW (1) | TWI765913B (hr) |
| UY (1) | UY37421A (hr) |
| WO (1) | WO2018059914A1 (hr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL265536B (en) * | 2016-09-27 | 2022-07-01 | Bayer Pharma AG | A method for the production of a crystalline form of the a modification of calcobuterol |
| 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-TETRAAZACYCLODODECAN-1,4 ,7-TRIYL)-TRIACETIC ACID AND THEIR COMPLEXES |
| EP3870569A4 (en) * | 2018-10-24 | 2022-08-24 | Biophore India Pharmaceuticals Pvt. Ltd. | NEW PROCESS FOR THE PREPARATION OF MACROCYCLIC CHELATING TRIACETIC ACID 2,2',2''-(10-(2-HYDROXYPROPYL)-1,4,7,10-TETRA AZACYCLODODECANE-1,4,7-TRIYL) AND ITS COMPLEXES WITH PARAMAGNETIC METALLIC IONS |
| 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 |
| 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 |
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| GB1491129A (en) | 1975-06-04 | 1977-11-09 | Guerbet Sa | Iodo-benzene derivatives and an x-ray contrast medium containing them |
| US4284620A (en) | 1979-03-23 | 1981-08-18 | Mallinckrodt, Inc. | N-(2-Hydroxyethyl)-2,4,6-triiodo-3,5-bis-(2-keto-L-gulonamido)benzamide and radiological compositions containing same |
| NO161560C (no) | 1980-04-17 | 1989-09-06 | Univ California | Symmetriske trijodisoftaldiamid-derivater og roentgenkontrastmidler inneholdende disse. |
| DE3150916A1 (de) | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-hydroxyaethylierte 2,4,6-trijodaminoisiophthalsaeure-bis- trihydroxybutylamide, deren herstellung und diese enthaltende roentgenkontrastmittel" |
| US5059412A (en) | 1984-06-04 | 1991-10-22 | The Dow Chemical Company | Macrocyclic aminophosphonic acid complexes for the treatment of calcific tumors |
| US5064633A (en) | 1984-06-04 | 1991-11-12 | The Dow Chemical Company | Macrocyclic aminophosphonic acid complexes, their formulations and use |
| US4885363A (en) | 1987-04-24 | 1989-12-05 | E. R. Squibb & Sons, Inc. | 1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs |
| MX174467B (es) | 1986-01-23 | 1994-05-17 | Squibb & Sons Inc | 1,4,7-triscarboximetil-1,4,7,10-tetraazaciclodo decano substituido en 1 y compuestos analogos |
| 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 |
| JPH0899996A (ja) | 1990-03-23 | 1996-04-16 | Yamanouchi Europ Bv | Ｉｌ−６抑制組成物 |
| DE4035760A1 (de) | 1990-11-08 | 1992-05-14 | Schering Ag | Mono-n-substituierte 1,4,7,10-tetraazacyclododecan-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| 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 |
| US5410043A (en) | 1991-12-06 | 1995-04-25 | Schering Aktiengesellschaft | Process for the production of mono-N-substituted tetraaza macrocycles |
| 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 |
| DE4318369C1 (de) | 1993-05-28 | 1995-02-09 | Schering Ag | Verwendung von makrocyclischen Metallkomplexen als Temperatursonden |
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| PE20141325A1 (es) * | 2011-04-21 | 2014-10-08 | Bayer Ip Gmbh | Preparacion de gadobutrol de alta pureza |
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| KR101693400B1 (ko) | 2014-09-17 | 2017-01-05 | 에스티팜 주식회사 | 칼코부트롤의 제조방법 |
| 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 |
| 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 |
| IL265536B (en) * | 2016-09-27 | 2022-07-01 | Bayer Pharma AG | A method for the production of a crystalline form of the a modification of calcobuterol |
-
2017
- 2017-09-11 IL IL265536A patent/IL265536B/en unknown
- 2017-09-11 RS RS20200654A patent/RS60392B1/sr unknown
- 2017-09-11 AU AU2017333698A patent/AU2017333698B2/en active Active
- 2017-09-11 LT LTEP17768733.2T patent/LT3519394T/lt unknown
- 2017-09-11 EP EP17768733.2A patent/EP3519394B1/en active Active
- 2017-09-11 SG SG11201901460UA patent/SG11201901460UA/en unknown
- 2017-09-11 US US16/336,217 patent/US10793532B2/en active Active
- 2017-09-11 WO PCT/EP2017/072683 patent/WO2018059914A1/en active Application Filing
- 2017-09-11 CN CN201780058632.5A patent/CN109803958B/zh active Active
- 2017-09-11 SI SI201730298T patent/SI3519394T1/sl unknown
- 2017-09-11 DK DK17768733.2T patent/DK3519394T3/da active
- 2017-09-11 CA CA3038036A patent/CA3038036C/en active Active
- 2017-09-11 BR BR112019006066A patent/BR112019006066A2/pt not_active Application Discontinuation
- 2017-09-11 KR KR1020197008763A patent/KR102395523B1/ko active IP Right Grant
- 2017-09-11 PT PT177687332T patent/PT3519394T/pt unknown
- 2017-09-11 MX MX2019003540A patent/MX2019003540A/es unknown
- 2017-09-11 PL PL17768733T patent/PL3519394T3/pl unknown
- 2017-09-11 HU HUE17768733A patent/HUE050553T2/hu unknown
- 2017-09-11 NZ NZ751256A patent/NZ751256A/en unknown
- 2017-09-11 JP JP2019516489A patent/JP7053590B2/ja active Active
- 2017-09-11 ES ES17768733T patent/ES2809736T3/es active Active
- 2017-09-27 TW TW106133043A patent/TWI765913B/zh active
- 2017-09-27 AR ARP170102671A patent/AR109729A1/es unknown
- 2017-09-27 UY UY0001037421A patent/UY37421A/es unknown
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2020
- 2020-06-09 HR HRP20200922TT patent/HRP20200922T1/hr unknown
- 2020-07-30 CY CY20201100709T patent/CY1123317T1/el unknown
- 2020-09-22 US US17/028,467 patent/US11390592B2/en active Active
-
2022
- 2022-03-03 JP JP2022032582A patent/JP7444914B2/ja active Active
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