HRP20161256T1 - Postupak priprave 17-supstituiranih steroida - Google Patents
Postupak priprave 17-supstituiranih steroida Download PDFInfo
- Publication number
- HRP20161256T1 HRP20161256T1 HRP20161256TT HRP20161256T HRP20161256T1 HR P20161256 T1 HRP20161256 T1 HR P20161256T1 HR P20161256T T HRP20161256T T HR P20161256TT HR P20161256 T HRP20161256 T HR P20161256T HR P20161256 T1 HRP20161256 T1 HR P20161256T1
- Authority
- HR
- Croatia
- Prior art keywords
- abiraterone
- formula
- compound
- carried out
- image
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims 13
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 229960000853 abiraterone Drugs 0.000 claims 5
- GZOSMCIZMLWJML-VJLLXTKPSA-N abiraterone Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CC[C@H](O)CC3=CC2)C)CC[C@@]11C)C=C1C1=CC=CN=C1 GZOSMCIZMLWJML-VJLLXTKPSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 229960004103 abiraterone acetate Drugs 0.000 claims 3
- UVIQSJCZCSLXRZ-UBUQANBQSA-N abiraterone acetate Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CC[C@@H](CC4=CC[C@H]31)OC(=O)C)C=C2C1=CC=CN=C1 UVIQSJCZCSLXRZ-UBUQANBQSA-N 0.000 claims 3
- 230000001476 alcoholic effect Effects 0.000 claims 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims 2
- HSXOYJPVRGBXKE-UHFFFAOYSA-N BC1=CC=CN=C1 Chemical class BC1=CC=CN=C1 HSXOYJPVRGBXKE-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- ZVNOFPTXVOXIGG-PGRUEHTASA-N (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthrene-3-carboxylic acid Chemical group C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](CC[C@]34C)C(O)=O)[C@@H]1CC=C2c1cccnc1 ZVNOFPTXVOXIGG-PGRUEHTASA-N 0.000 claims 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 229920001429 chelating resin Polymers 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- -1 triflate compound Chemical class 0.000 claims 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0059—Estrane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Claims (15)
1. Postupak priprave abiraterona, naznačen time što obuhvaća:
a) trifliranje spoja formule
[image]
u prisutnosti baze kako bi se dobio spoj formule
[image]
b) stavljanje sirovog spoja formule (VI) u kontakt s derivatom 3-piridilborana u uvjetima Suzukijevog ukriženog konjugiranja kako bi se dobio 3β-formiloksi ester abiraterona formule
[image]
;
c) hidrolizu sirovog 3β-formiloksi estera abiraterona formule (VII); i
d) izdvajanje dobivenog abiraterona iz alkoholnog otapala.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što se korak a) provodi u prisutnosti baze koju se bira između trietilamina, metilimidazola i 2,6-lutidina.
3. Postupak u skladu s patentnim zahtjevom 2, naznačen time što se korak a) provodi u prisutnosti 2,6-lutidina.
4. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što se korak a) provodi na sobnoj temperaturi.
5. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što se u koraku a) spoju formule (V) istodobno doda 1 ekvivalent organske baze i 1,1 ekvivalent anhidrida trifluormetansulfonske kiseline.
6. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što se u koraku b) upotrebljava 1,1 ekv. derivata 3-piridilborana u odnosu na triflatni spoj formule (VI).
7. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što se korak b) provodi na temperaturi refluksa.
8. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 7, naznačen time što se korak b) provodi u prisutnosti bis(trifenilfosfin)paladijevog diklorida.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 8, naznačen time što je u koraku d) alkoholno otapalo metanol.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što se dodatno sastoji u prevođenju abiraterona u abirateron-acetat.
11. Postupak u skladu s patentnim zahtjevom 10, naznačen time što abirateron-acetat se kristalitira iz heksanske i etanolne otopine.
12. Postupak u skladu s patentnim zahtjevom 11, naznačen time što se u navedenu heksansku i etanolnu otopinu abirateron-acetata dodaju drveni ugljen i kelirajuća smola.
13. Postupak u skladu s bilo kojim od patentnih zahtjeva 1 do 12, naznačen time što dodatno obuhvaća prikupljanju neizreagiranog DHEA iz alkoholne otopine u koraku d).
14. Spoj, naznačen time što je (3β)-17-(3-piridinil)androsta-5,16-dien-3-il-formijat.
15. Spoj, naznačen time što je (3β)-formiloksiandrosta-5,16-dien-17-il-trifluormetansulfonat.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11306310 | 2011-10-10 | ||
| PCT/EP2012/069937 WO2013053691A1 (en) | 2011-10-10 | 2012-10-09 | Process for preparing 17-substituted steroids |
| EP12774995.0A EP2766381B1 (en) | 2011-10-10 | 2012-10-09 | Process for preparing 17-substituted steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161256T1 true HRP20161256T1 (hr) | 2016-11-18 |
Family
ID=47045010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161256TT HRP20161256T1 (hr) | 2011-10-10 | 2016-10-03 | Postupak priprave 17-supstituiranih steroida |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9353145B2 (hr) |
| EP (1) | EP2766381B1 (hr) |
| JP (1) | JP6091510B2 (hr) |
| CN (1) | CN104066744B (hr) |
| BR (1) | BR112014008671B1 (hr) |
| CA (1) | CA2851330C (hr) |
| ES (1) | ES2590753T3 (hr) |
| HR (1) | HRP20161256T1 (hr) |
| HU (1) | HUE029523T2 (hr) |
| IL (1) | IL231995A (hr) |
| PL (1) | PL2766381T3 (hr) |
| RS (1) | RS55223B1 (hr) |
| SI (1) | SI2766381T1 (hr) |
| WO (1) | WO2013053691A1 (hr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140053836A (ko) | 2011-01-11 | 2014-05-08 | 글락소스미스클라인 엘엘씨 | 조합물 |
| ITMI20121788A1 (it) * | 2012-10-22 | 2014-04-23 | Olon Spa | Procedimento per la purificazione di abiraterone acetato |
| WO2014111815A2 (en) * | 2013-01-18 | 2014-07-24 | Cortendo Ab (Publ) | Abiraterone and analogs thereof for the treatment of diseases associated with cortisol overproduction |
| PL2792682T3 (pl) | 2013-04-19 | 2017-04-28 | Zach System | Sposób wytwarzania stałej postaci octanu abirateronu |
| KR20160024930A (ko) | 2013-06-28 | 2016-03-07 | 시노팜 타이완 리미티드 | 아비라테론 및 이의 중간체의 제조를 위한 방법 |
| AU2014330780B2 (en) * | 2013-10-01 | 2017-05-25 | Novartis Ag | Enzalutamide in combination with Afuresertib for the treatment of cancer |
| EP3099701B1 (en) | 2014-01-28 | 2019-07-24 | OLON S.p.A. | Procedure for the preparation of abiraterone acetate and intermediates thereof |
| US10722527B2 (en) | 2015-04-10 | 2020-07-28 | Capsugel Belgium Nv | Abiraterone acetate lipid formulations |
| ITUB20155309A1 (it) * | 2015-10-27 | 2017-04-27 | Olon Spa | Procedimento per la preparazione di abiraterone acetato e suoi intermedi |
| CN105503992A (zh) * | 2016-01-22 | 2016-04-20 | 江苏联环药业股份有限公司 | 一种醋酸阿比特龙的制备方法 |
| WO2018071544A1 (en) * | 2016-10-11 | 2018-04-19 | Zhuhai Beihai Biotech Co., Ltd. | Abiraterone derivative and formulations thereof |
| CN108948120A (zh) * | 2018-07-07 | 2018-12-07 | 张正光 | 一种醋酸阿比特龙中间体的制备方法 |
| CN111349138B (zh) * | 2018-12-24 | 2023-06-16 | 江苏恒瑞医药股份有限公司 | 制备醋酸阿比特龙的方法 |
| AU2020232706A1 (en) | 2019-03-06 | 2021-09-16 | Propella Therapeutics, Inc. | Abiraterone prodrugs |
| CN112812147A (zh) * | 2019-11-15 | 2021-05-18 | 江苏佳尔科药业集团股份有限公司 | 一种醋酸阿比特龙的合成方法及其中间体 |
| WO2022174134A1 (en) | 2021-02-15 | 2022-08-18 | Propella Therapeutics, Inc. | Abiraterone prodrugs |
| CN115466302A (zh) * | 2022-10-26 | 2022-12-13 | 山西振东制药股份有限公司 | 醋酸阿比特龙的合成及纯化方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69327096T2 (de) | 1992-03-31 | 2000-06-21 | Btg Int Ltd | 17-substituierte steroide, verwendbar bei behandlung von krebs |
| ATE176481T1 (de) | 1993-09-30 | 1999-02-15 | Btg Int Ltd | Synthese von 17-(3-pyridyl) steroiden |
| DK1781683T3 (da) | 2004-08-24 | 2012-02-06 | Btg Int Ltd | Fremgangsmåde til fremstilling af 17-vinyl-triflater som halvfabrikata |
| GB0418900D0 (en) | 2004-08-24 | 2004-09-29 | Btg Int Ltd | Novel salt forms |
| CN101768199B (zh) | 2009-12-24 | 2014-03-26 | 深圳万乐药业有限公司 | 醋酸阿比特龙的多晶型物及其制备方法 |
-
2012
- 2012-10-09 WO PCT/EP2012/069937 patent/WO2013053691A1/en active Application Filing
- 2012-10-09 EP EP12774995.0A patent/EP2766381B1/en active Active
- 2012-10-09 HU HUE12774995A patent/HUE029523T2/en unknown
- 2012-10-09 PL PL12774995.0T patent/PL2766381T3/pl unknown
- 2012-10-09 CN CN201280049786.5A patent/CN104066744B/zh active Active
- 2012-10-09 JP JP2014535024A patent/JP6091510B2/ja not_active Expired - Fee Related
- 2012-10-09 RS RS20160827A patent/RS55223B1/sr unknown
- 2012-10-09 BR BR112014008671-0A patent/BR112014008671B1/pt active IP Right Grant
- 2012-10-09 ES ES12774995.0T patent/ES2590753T3/es active Active
- 2012-10-09 SI SI201230729A patent/SI2766381T1/sl unknown
- 2012-10-09 CA CA2851330A patent/CA2851330C/en active Active
- 2012-10-09 US US14/350,456 patent/US9353145B2/en not_active Expired - Fee Related
-
2014
- 2014-04-08 IL IL231995A patent/IL231995A/en active IP Right Grant
-
2016
- 2016-10-03 HR HRP20161256TT patent/HRP20161256T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2766381T3 (pl) | 2016-12-30 |
| BR112014008671A2 (pt) | 2017-04-18 |
| JP2014528461A (ja) | 2014-10-27 |
| US20140256932A1 (en) | 2014-09-11 |
| EP2766381A1 (en) | 2014-08-20 |
| RS55223B1 (sr) | 2017-02-28 |
| HUE029523T2 (en) | 2017-03-28 |
| EP2766381B1 (en) | 2016-07-27 |
| SI2766381T1 (sl) | 2016-11-30 |
| JP6091510B2 (ja) | 2017-03-08 |
| BR112014008671B1 (pt) | 2022-07-12 |
| IL231995A (en) | 2016-05-31 |
| CA2851330A1 (en) | 2013-04-18 |
| CN104066744B (zh) | 2017-03-22 |
| CN104066744A (zh) | 2014-09-24 |
| ES2590753T3 (es) | 2016-11-23 |
| CA2851330C (en) | 2019-07-16 |
| US9353145B2 (en) | 2016-05-31 |
| WO2013053691A1 (en) | 2013-04-18 |
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