HRP20110168T1 - Postupak priprave drospirenona - Google Patents
Postupak priprave drospirenona Download PDFInfo
- Publication number
- HRP20110168T1 HRP20110168T1 HR20110168T HRP20110168T HRP20110168T1 HR P20110168 T1 HRP20110168 T1 HR P20110168T1 HR 20110168 T HR20110168 T HR 20110168T HR P20110168 T HRP20110168 T HR P20110168T HR P20110168 T1 HRP20110168 T1 HR P20110168T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- image
- methylene
- reaction
- pivaloyloxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 10
- METQSPRSQINEEU-UHFFFAOYSA-N dihydrospirorenone Natural products CC12CCC(C3(CCC(=O)C=C3C3CC33)C)C3C1C1CC1C21CCC(=O)O1 METQSPRSQINEEU-UHFFFAOYSA-N 0.000 title claims abstract 4
- METQSPRSQINEEU-HXCATZOESA-N drospirenone Chemical compound C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 METQSPRSQINEEU-HXCATZOESA-N 0.000 title claims abstract 4
- 229960004845 drospirenone Drugs 0.000 title claims abstract 4
- 238000002360 preparation method Methods 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 9
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- MLROWSBVFNKEEF-AWBCXTIISA-N 82543-09-7 Chemical compound C([C@@H]12)C[C@]3(C)C(=O)[C@H]4C[C@H]4[C@H]3[C@@H]1[C@@H](O)C=C1[C@]2(C)CC[C@H](OC(=O)C(C)(C)C)C1 MLROWSBVFNKEEF-AWBCXTIISA-N 0.000 claims 2
- 229910016887 MnIV Inorganic materials 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 claims 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims 1
- IYCDFUCBUZDDIU-MBYPHNFESA-N 82543-15-5 Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C([C@H]4C[C@H]44)=O)[C@@H]4[C@@H]3C=C[C@@]21O IYCDFUCBUZDDIU-MBYPHNFESA-N 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- WLKSETNDPGMVPB-LDXXCXQDSA-N [(1S,2R,5S,7S,9R,10R,11R,12S,13S,15S,17S)-10-hydroxy-2,17-dimethyl-16-oxo-8-oxahexacyclo[9.8.0.02,7.07,9.012,17.013,15]nonadecan-5-yl] 2,2-dimethylpropanoate Chemical compound C([C@@H]1[C@@]2(C)CC[C@@H](C3)OC(=O)C(C)(C)C)C[C@]4(C)C(=O)[C@H]5C[C@H]5[C@H]4[C@@H]1[C@@H](O)[C@@H]1[C@@]23O1 WLKSETNDPGMVPB-LDXXCXQDSA-N 0.000 claims 1
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims 1
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 239000012286 potassium permanganate Substances 0.000 claims 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 claims 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/008—3 membered carbocyclic rings in position 15/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Postupak priprave 6?,7?,15?,16?-dimetilen-3-oksi-17α-pregn-4-en-21,17-karbolaktona (I), naznačen time da obuhvaća sljedeće korake: 1) reakcija spoja 66sa spojem formule II:IIu kojoj je X halogen, a R- je -CH2-ORI, pri čemu je RI jedna od sljedećih zaštitnih skupina hidroksila: i) sililni derivat Q3Si-, u kojem Q neovisno jedan od drugog predstavljaju (C1-C6)alkil, (C6-C10)aril, (C1-C4)alkilaril ili (C1-C4)alkoksiaril, ii) u kojoj n jest 1 ili 2; pri čemu je dobiven spoj 8:82) oksidacija spoja 8 s oksidansom zasnovanom na MnIV/VII uz uklanjanje skupine RI i time dobivanje drozpirenona I:Patent sadrži još 7 patentnih zahtjeva.
Claims (8)
1. Postupak priprave 6β,7β,15β,16β-dimetilen-3-oksi-17α-pregn-4-en-21,17-karbolaktona (I), naznačen time da obuhvaća sljedeće korake:
1) reakcija spoja 6
[image]
6
sa spojem formule II:
[image]
II
u kojoj je X halogen, a R- je -CH2-ORI, pri čemu je RI jedna od sljedećih zaštitnih skupina hidroksila:
i) sililni derivat Q3Si-, u kojem Q neovisno jedan od drugog predstavljaju (C1-C6)alkil, (C6-C10)aril, (C1-C4)alkilaril ili (C1-C4)alkoksiaril,
ii)
[image]
u kojoj n jest 1 ili 2;
pri čemu je dobiven spoj 8:
[image]
8
2) oksidacija spoja 8 s oksidansom zasnovanom na MnIV/VII uz uklanjanje skupine RI i time dobivanje drozpirenona I:
[image]
2. Postupak prema patentnom zahtjevu 1, naznačen time da se korak (1) provodi u aprotonskom otapalu u prisutnosti litija.
3. Postupak prema patentnom zahtjevu 1, naznačen time da dalje obuhvaća pretvorbu spoja II u odgovarajući alkilmagnezijev derivat prije njegove reakcije sa spojem 6.
4. Postupak prema patentnom zahtjevu 1, naznačen time da je rečeni oksidans zasnovan na MnIV/VII odabran od MnO2 i KMnO4.
5. Postupak prema patentnom zahtjevu 1, naznačen time da je u koraku 2) spoj 8, u kojem R = CH2-ORI gdje RI jest Q3Si-, a Q je kao što je definiran u patentnom zahtjevu 1, prvo oksidiran s manganovim dioksidom čime nastaje međuprodukt 9, koji je zatim hidroliziran da se ukloni RI skupina, čime nastaje međuprodukt 10:
[image]
10
koji je potpuno konačno oksidiran do laktona s manganovim dioksidom, čime nastaje drozpirenon.
6. Postupak prema patentnom zahtjevu 1, naznačen time da je u koraku 2) spoj 8, u kojem R = CH2-ORI gdje RI jest Q3Si- a Q je kao što je definiran u patentnom zahtjevu 1, hidroliziran dajući međuprodukt 11:
[image]
11
koji je zatim oksidiran s manganovim dioksidom pri čemu nastaje drozpirenon.
7. Postupak prema patentnom zahtjevu 1, naznačen time da dalje obuhvaća sljedeće korake u pripravi 3β,5-dihidroksi-6β,7β,15β,16β-dimetilen-5β-androstan-17-ona (spoj 6):
a) epoksidacija 7β-hidroksi-15β,16β-metilen-3β-pivaloiloksi-5-androsten-17-ona (1) s tert-butilhidroperoksidom u prisutnosti vanadil-acetilacetonata u toluenu pri 70-75°C, pri čemu nastaje 5,6β-epoksi-7β-hidroksi-15β,16β-metilen-3β-pivaloiloksi-5β-androstan-17-on 2:
[image]
b) reakcija spoja 2 s heksakloracetonom u diklormetanu koji je dodan s trifenilfosfinom pri temperaturi od 0-5 °C, a zatim zagrijavanje do 10-15 °C, pri čemu nastaje 7α-klor-5,6β-epoksi-15β,16β-metilen-3β-pivaloiloksi-5β-androstan-17-on 3:
[image]
c) otvaranje epoksidnog prstena spoja 3 uz istovremeno uklanjanje atoma klora, a reakcijom s octenom kiselinom i bakrovim bromidom u 1,2-dimetoksietanu zagrijavanjem na 70°C, čime je dobiven 5-hidroksi-15β,16β-metilen-3β-pivaloiloksi-5β-androst-6-en-17-on 4:
[image]
d) uklanjanje pivaloilne skupine u položaju 3 spoja 4 s kalijevim hidroksidom u smjesi tetrahidrofuran/metanola u prisutnosti natrijevog perklorata pri sobnoj temperaturi, nakon čega slijedi dodatak sumporne kiseline do pH 7, čime se dobiva 3β,5-dihidroksi-15β,16β-metilen-5β-androst-6-en-17-on 5:
[image]
e) pretvorba spoja 5 u 3β,5-dihidroksi-6β,7β,15β,16β-dimetilen-5β-androst-17-on 6 reakcijom s dibrommetanom u 1,2-dimetoksietanu u prisutnosti cinka i bakrovog bromida uz zagrijevanje pri 75 °C, te zatim dodatkom octene kiseline i izoproanola:
[image]
8. Spoj, naznačen time da je odabran iz sljedeće skupine:
[image]
gdje je R kao što je definiran u patentnom zahtjevu 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07014742A EP2019114B1 (en) | 2007-07-26 | 2007-07-26 | Process for the preparation of Drospirenone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110168T1 true HRP20110168T1 (hr) | 2011-04-30 |
Family
ID=38705123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110168T HRP20110168T1 (hr) | 2007-07-26 | 2011-03-07 | Postupak priprave drospirenona |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8383809B2 (hr) |
| EP (1) | EP2019114B1 (hr) |
| AT (1) | ATE491717T1 (hr) |
| BR (1) | BRPI0814126A2 (hr) |
| CY (1) | CY1111690T1 (hr) |
| DE (1) | DE602007011250D1 (hr) |
| DK (1) | DK2019114T3 (hr) |
| ES (1) | ES2355586T3 (hr) |
| HR (1) | HRP20110168T1 (hr) |
| PL (1) | PL2019114T3 (hr) |
| PT (1) | PT2019114E (hr) |
| RS (1) | RS51892B (hr) |
| SI (1) | SI2019114T1 (hr) |
| WO (1) | WO2009012955A2 (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8334375B2 (en) | 2009-04-10 | 2012-12-18 | Evestra, Inc. | Methods for the preparation of drospirenone |
| DE102009031909B4 (de) | 2009-07-01 | 2017-02-09 | Heyl Chemisch-Pharmazeutische Fabrik Gmbh & Co. Kg | Verfahren zur Herstellung von Drospirenon aus Prasteron |
| WO2011000535A2 (de) * | 2009-07-01 | 2011-01-06 | Heyl Chemisch-Pharmazeutische Fabrik Gmbh & Co. K | Verfahren zur herstellung von drospirenon |
| DE102009031907B4 (de) | 2009-07-01 | 2017-02-09 | Heyl Chemisch-Pharmazeutische Fabrik Gmbh & Co. Kg | Verfahren zur Herstellung von Drospirenon aus Androstendion |
| DE102010006818A1 (de) | 2010-01-31 | 2011-08-04 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG, 14167 | Verfahren zur Herstellung von Drospirenon aus 6ß, 7ß, 15ß, 16ß-Dimethylenandrost-4-en-3,17-dion |
| DE102009038972A1 (de) | 2009-08-23 | 2011-06-30 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co. KG, 14167 | Verfahren zur Herstellung von Drospirenon aus 6,7,15,16-Dimethylenandrost-4-en-3,17-dion |
| DE102009031908B4 (de) | 2009-07-01 | 2017-02-09 | Heyl Chemisch-Pharmazeutische Fabrik Gmbh & Co. Kg | Verfahren zur Herstellung von Drospirenon aus 15-Hydroxyandrostendion |
| ES2419663T3 (es) | 2010-08-03 | 2013-08-21 | Newchem S.P.A. | Métodos para la preparación de Drospirenona y productos intermedios de la misma |
| CN102887934B (zh) * | 2012-09-20 | 2015-05-27 | 杭州福斯特药业有限公司 | 一种屈螺酮的制备方法 |
| MX356791B (es) * | 2013-04-12 | 2018-06-12 | Ind Chimica Srl | Procedimiento para la preparacion de drospirenona. |
| CN114437169B (zh) * | 2022-01-25 | 2023-04-07 | 台州仙琚药业有限公司 | 一种屈螺酮关键中间体溴代物的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3042136A1 (de) * | 1980-11-03 | 1982-06-09 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur herstellung von 3 (beta), 7 (beta) -dihydroxy- (delta) (pfeil hoch)5(pfeil hoch) -steroiden |
| ITMI20040367A1 (it) * | 2004-03-01 | 2004-06-01 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
| HUP0402465A2 (en) * | 2004-11-30 | 2006-07-28 | Richter Gedeon Vegyeszet | Industrial process for preparing 17-hydroxy-6-betha, 7-betha, 15-betha, 16-betha-bis-methylene-3-oxo-17-alpha-pregn-4-ene-21-carboxylic acid gamma lacton and the main intermediates of the process |
| ITMI20042338A1 (it) * | 2004-12-06 | 2005-03-06 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
-
2007
- 2007-07-26 PL PL07014742T patent/PL2019114T3/pl unknown
- 2007-07-26 RS RS20110051A patent/RS51892B/en unknown
- 2007-07-26 SI SI200730528T patent/SI2019114T1/sl unknown
- 2007-07-26 ES ES07014742T patent/ES2355586T3/es active Active
- 2007-07-26 AT AT07014742T patent/ATE491717T1/de active
- 2007-07-26 DE DE602007011250T patent/DE602007011250D1/de active Active
- 2007-07-26 PT PT07014742T patent/PT2019114E/pt unknown
- 2007-07-26 EP EP07014742A patent/EP2019114B1/en active Active
- 2007-07-26 DK DK07014742.6T patent/DK2019114T3/da active
-
2008
- 2008-07-21 US US12/670,065 patent/US8383809B2/en active Active
- 2008-07-21 BR BRPI0814126-6A2A patent/BRPI0814126A2/pt not_active IP Right Cessation
- 2008-07-21 WO PCT/EP2008/005949 patent/WO2009012955A2/en active Application Filing
-
2011
- 2011-02-08 CY CY20111100143T patent/CY1111690T1/el unknown
- 2011-03-07 HR HR20110168T patent/HRP20110168T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS51892B (en) | 2012-02-29 |
| ATE491717T1 (de) | 2011-01-15 |
| DE602007011250D1 (de) | 2011-01-27 |
| US8383809B2 (en) | 2013-02-26 |
| CY1111690T1 (el) | 2015-10-07 |
| WO2009012955A3 (en) | 2009-04-02 |
| US20100222571A1 (en) | 2010-09-02 |
| PL2019114T3 (pl) | 2011-05-31 |
| WO2009012955A2 (en) | 2009-01-29 |
| EP2019114B1 (en) | 2010-12-15 |
| SI2019114T1 (sl) | 2011-04-29 |
| PT2019114E (pt) | 2011-02-07 |
| ES2355586T3 (es) | 2011-03-29 |
| EP2019114A1 (en) | 2009-01-28 |
| DK2019114T3 (da) | 2011-02-14 |
| BRPI0814126A2 (pt) | 2015-02-03 |
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