US20040034215A1 - 5-Androsten-3beta-ol steroid intermediates and processes for their preparation - Google Patents
5-Androsten-3beta-ol steroid intermediates and processes for their preparation Download PDFInfo
- Publication number
- US20040034215A1 US20040034215A1 US10/392,955 US39295503A US2004034215A1 US 20040034215 A1 US20040034215 A1 US 20040034215A1 US 39295503 A US39295503 A US 39295503A US 2004034215 A1 US2004034215 A1 US 2004034215A1
- Authority
- US
- United States
- Prior art keywords
- steroid
- preparation
- formula
- dihydroxy
- hydroxy
- 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.)
- Abandoned
Links
- 0 [3*]OC1CCC2(C)C(=C[C@H](O)C3C2CCC2(C)C3CCC2([17*])[18*])C1 Chemical compound [3*]OC1CCC2(C)C(=C[C@H](O)C3C2CCC2(C)C3CCC2([17*])[18*])C1 0.000 description 39
- XSQDTSWAPFCEDH-UHFFFAOYSA-N CC(C)C1(C(C)C)CCC(=O)O1 Chemical compound CC(C)C1(C(C)C)CCC(=O)O1 XSQDTSWAPFCEDH-UHFFFAOYSA-N 0.000 description 27
- GGCAYVSRFBLIQL-ZMVXVLJXSA-N B[IH-].C.C[IH-].F[IH-].[2H][IH-].[H][C@]12C3CCC(=O)[C@@]3(C)C[C@@H](O)[C@]1([H])[C@@]1(C)CC[C@H](O)CC1=C[C@@H]2O.[H][C@]12C3CCC(O)(C#C)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12C3CCC(O)(C#C)[C@@]3(C)C[C@@H](O)[C@]1([H])[C@@]1(C)CC[C@H](O)CC1=C[C@@H]2O.[H][C@]12C3CCC4(CCC(=O)O4)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12C3CCC4(CCC(O)O4)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12[C@H](C)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)C=C1C[C@@H](C)CC[C@@]12C Chemical compound B[IH-].C.C[IH-].F[IH-].[2H][IH-].[H][C@]12C3CCC(=O)[C@@]3(C)C[C@@H](O)[C@]1([H])[C@@]1(C)CC[C@H](O)CC1=C[C@@H]2O.[H][C@]12C3CCC(O)(C#C)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12C3CCC(O)(C#C)[C@@]3(C)C[C@@H](O)[C@]1([H])[C@@]1(C)CC[C@H](O)CC1=C[C@@H]2O.[H][C@]12C3CCC4(CCC(=O)O4)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12C3CCC4(CCC(O)O4)[C@@]3(C)C[C@@H](C)[C@]1([H])[C@@]1(C)CC[C@H](C)CC1=C[C@@H]2C.[H][C@]12[C@H](C)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)C=C1C[C@@H](C)CC[C@@]12C GGCAYVSRFBLIQL-ZMVXVLJXSA-N 0.000 description 1
- NZGCKHWTGUGMSU-XIWNZAOESA-M C.I[IH-].[H]C12=CC[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[H][C@]12C3CCC4(CCC(=O)O4)[C@@]3(C)C[C@H]3O[C@]31[C@@]1(C)CCC(=O)C=C1C[C@H]2C(=O)OC.[H][C@]12[C@H](C)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)C=C1C[C@@H](O)CC[C@@]12C.[H][C@]12[C@H](O)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[H][C@]12[C@H](OC(C)=O)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[I-] Chemical compound C.I[IH-].[H]C12=CC[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[H][C@]12C3CCC4(CCC(=O)O4)[C@@]3(C)C[C@H]3O[C@]31[C@@]1(C)CCC(=O)C=C1C[C@H]2C(=O)OC.[H][C@]12[C@H](C)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)C=C1C[C@@H](O)CC[C@@]12C.[H][C@]12[C@H](O)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[H][C@]12[C@H](OC(C)=O)C[C@@]3(C)C(CCC34CCC(=O)O4)[C@]1([H])[C@H](C(=O)OC)CC1=CC(=O)CC[C@@]12C.[I-] NZGCKHWTGUGMSU-XIWNZAOESA-M 0.000 description 1
- SRIXAYZRZQIECO-UHFFFAOYSA-N CC(C)C(C)(CC1)OC1=O Chemical compound CC(C)C(C)(CC1)OC1=O SRIXAYZRZQIECO-UHFFFAOYSA-N 0.000 description 1
- INPIQFXITQDSCK-CIAQGDOXSA-N COC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C2=CC[C@]2(C)C(=O)CCC32)C1.COC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C4CCC(=O)[C@@]4(C)C[C@@H](O)C32)C1.C[C@]12CC[C@H](O)CC1=CCC1C2=CC[C@]2(C)C(=O)CCC12.C[C@]12C[C@@H](O)C3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CCC2=O Chemical compound COC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C2=CC[C@]2(C)C(=O)CCC32)C1.COC(=O)O[C@H]1CC[C@@]2(C)C(=CCC3C4CCC(=O)[C@@]4(C)C[C@@H](O)C32)C1.C[C@]12CC[C@H](O)CC1=CCC1C2=CC[C@]2(C)C(=O)CCC12.C[C@]12C[C@@H](O)C3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CCC2=O INPIQFXITQDSCK-CIAQGDOXSA-N 0.000 description 1
Classifications
-
- 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
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
Definitions
- r.p.m. refers to revolutions per minute.
- Bioconversion cultures are assayed on a daily basis for 5,9(11)-androstadien-3 ⁇ ,7 ⁇ -diol-17-one using the procedure described in EXAMPLE 1. Bioconversion of 5,9(11)-androstadien-3 ⁇ -ol-17-one to 5,9(11)-androstadien-3 ⁇ ,7 ⁇ -diol-17-one is complete approximately 3 days post-inoculation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/392,955 US20040034215A1 (en) | 2002-08-16 | 2003-03-21 | 5-Androsten-3beta-ol steroid intermediates and processes for their preparation |
| US10/858,177 US7002028B2 (en) | 2002-08-16 | 2004-06-01 | 5-androsten-3β-ol steroid intermediates and processes for their preparation |
| US11/137,153 US20070066579A1 (en) | 2002-08-16 | 2005-05-25 | 5-androsten-3beta-ol steroid intermediates and processs for their preparation |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40399002P | 2002-08-16 | 2002-08-16 | |
| US41529302P | 2002-10-01 | 2002-10-01 | |
| US10/392,955 US20040034215A1 (en) | 2002-08-16 | 2003-03-21 | 5-Androsten-3beta-ol steroid intermediates and processes for their preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/858,177 Division US7002028B2 (en) | 2002-08-16 | 2004-06-01 | 5-androsten-3β-ol steroid intermediates and processes for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20040034215A1 true US20040034215A1 (en) | 2004-02-19 |
Family
ID=31891414
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/392,955 Abandoned US20040034215A1 (en) | 2002-08-16 | 2003-03-21 | 5-Androsten-3beta-ol steroid intermediates and processes for their preparation |
| US10/858,177 Expired - Fee Related US7002028B2 (en) | 2002-08-16 | 2004-06-01 | 5-androsten-3β-ol steroid intermediates and processes for their preparation |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/858,177 Expired - Fee Related US7002028B2 (en) | 2002-08-16 | 2004-06-01 | 5-androsten-3β-ol steroid intermediates and processes for their preparation |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US20040034215A1 (de) |
| EP (1) | EP1534732B1 (de) |
| JP (1) | JP2006507369A (de) |
| AT (1) | ATE339437T1 (de) |
| AU (1) | AU2003285485A1 (de) |
| BR (1) | BR0313523A (de) |
| CA (1) | CA2495412A1 (de) |
| DE (1) | DE60308388T2 (de) |
| ES (1) | ES2271636T3 (de) |
| MX (1) | MXPA05001857A (de) |
| TW (1) | TW200406419A (de) |
| WO (1) | WO2004016640A2 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057734A (zh) * | 2019-12-24 | 2020-04-24 | 天津科技大学 | 一种甲基睾丸素高效转化生产11α-羟基-甲基睾丸素的方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20042338A1 (it) * | 2004-12-06 | 2005-03-06 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
| US8084446B2 (en) * | 2005-04-26 | 2011-12-27 | Eric Marchewitz | Use of DHEA derivatives for enhancing physical performance |
| HUE038504T2 (hu) * | 2005-07-21 | 2018-10-29 | Bayer Ip Gmbh | Eljárás 3-oxo-pregn-4-én-21,17-karbolaktonok elõállítására 17-(3-hidroxipropil)-3,17,dihidroxiandrosztánok fémmentes oxidációjával |
| PL1746101T5 (pl) * | 2005-07-21 | 2014-11-28 | Bayer Pharma AG | Sposób wytwarzania 3-oksopreg-4-eno-21,17-karbolaktonów drogą bezmetalowego utleniania 17-(3-hydroksypropylo-3,17-dihydroksyandrostanu |
| US7319154B2 (en) * | 2005-07-21 | 2008-01-15 | Bayer Schering Pharma Ag | Process for the production of 3-oxo-pregn-4-ene-21, 17-carbolactones by the metal free oxidation of 17-(3-hydroxypropyl)-3, 17-dihydroxyandrostanes |
| CN110331182A (zh) * | 2019-08-06 | 2019-10-15 | 江苏远大仙乐药业有限公司 | 一种甾体中间体的生物转化制备方法 |
| CN110885869A (zh) * | 2019-12-24 | 2020-03-17 | 天津科技大学 | 一种利用微生物转化生产7α-羟基-脱氢表雄酮的方法 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294646A (en) * | 1963-10-23 | 1966-12-27 | American Home Prod | Microbiological hydroxylation of norsteroids using aspergillus ochraceus |
| US4031074A (en) * | 1974-09-02 | 1977-06-21 | Akzona Incorporated | Process for the preparation of 11β-hydroxy-18-alkyl-estrane compounds |
| US4045574A (en) * | 1973-11-30 | 1977-08-30 | Schering Aktiengesellschaft | D-homo-20-ketopregnanes |
| US4054563A (en) * | 1975-04-25 | 1977-10-18 | Ciba-Geigy Corporation | Process for the manufacture of spiro compounds of the steroid series |
| US4056633A (en) * | 1974-12-23 | 1977-11-01 | Schering Aktiengesellschaft | D-homo-20-ketopregnanes and method for inducing anesthesia or narcosis |
| US4196203A (en) * | 1976-12-10 | 1980-04-01 | Schering Aktiengesellschaft | Novel corticoids |
| US4336332A (en) * | 1979-02-20 | 1982-06-22 | Hoffmann-La Roche, Inc. | Process for the manufacture of hydroxylated steroids |
| US4416985A (en) * | 1980-11-03 | 1983-11-22 | Schering, Aktiengesellschaft | Process for preparing 3β,7β-dihydroxy-Δ5 -steroids |
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| US5981744A (en) * | 1995-12-11 | 1999-11-09 | G. D. Searle And Co. | Processes for preparation of 9,11-epoxy steroids and intermediates useful therein |
| US6046023A (en) * | 1995-12-12 | 2000-04-04 | Akzo Nobel, N.V. | Microbial 11α-hydroxylation of steroids |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2349022A1 (de) * | 1973-09-26 | 1975-04-10 | Schering Ag | Neue d-homo-steroide |
| AU7978794A (en) * | 1993-10-13 | 1995-05-04 | Neurocrine Biosciences, Inc. | 3,17-dihydroxy-3,7,16 and/or 17-methyl-androst-5-ene compounds, derivatives thereof, and their use |
| FR2771105A1 (fr) | 1997-11-20 | 1999-05-21 | Vitasterol | Utilisation du fusarium monoliforme pour la preparation des derives 7alpha-hydroxyles de la dehydroepiandrosterone et de la pregnenolone |
-
2003
- 2003-03-21 WO PCT/US2003/007791 patent/WO2004016640A2/en active IP Right Grant
- 2003-03-21 EP EP03756776A patent/EP1534732B1/de not_active Expired - Lifetime
- 2003-03-21 ES ES03756776T patent/ES2271636T3/es not_active Expired - Lifetime
- 2003-03-21 JP JP2005502036A patent/JP2006507369A/ja not_active Abandoned
- 2003-03-21 AT AT03756776T patent/ATE339437T1/de not_active IP Right Cessation
- 2003-03-21 AU AU2003285485A patent/AU2003285485A1/en not_active Abandoned
- 2003-03-21 CA CA002495412A patent/CA2495412A1/en not_active Abandoned
- 2003-03-21 MX MXPA05001857A patent/MXPA05001857A/es unknown
- 2003-03-21 DE DE60308388T patent/DE60308388T2/de not_active Expired - Fee Related
- 2003-03-21 BR BR0313523-3A patent/BR0313523A/pt not_active IP Right Cessation
- 2003-03-21 TW TW092106331A patent/TW200406419A/zh unknown
- 2003-03-21 US US10/392,955 patent/US20040034215A1/en not_active Abandoned
-
2004
- 2004-06-01 US US10/858,177 patent/US7002028B2/en not_active Expired - Fee Related
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294646A (en) * | 1963-10-23 | 1966-12-27 | American Home Prod | Microbiological hydroxylation of norsteroids using aspergillus ochraceus |
| US4045574A (en) * | 1973-11-30 | 1977-08-30 | Schering Aktiengesellschaft | D-homo-20-ketopregnanes |
| US4031074A (en) * | 1974-09-02 | 1977-06-21 | Akzona Incorporated | Process for the preparation of 11β-hydroxy-18-alkyl-estrane compounds |
| US4056633A (en) * | 1974-12-23 | 1977-11-01 | Schering Aktiengesellschaft | D-homo-20-ketopregnanes and method for inducing anesthesia or narcosis |
| US4054563A (en) * | 1975-04-25 | 1977-10-18 | Ciba-Geigy Corporation | Process for the manufacture of spiro compounds of the steroid series |
| US4196203A (en) * | 1976-12-10 | 1980-04-01 | Schering Aktiengesellschaft | Novel corticoids |
| US4336332A (en) * | 1979-02-20 | 1982-06-22 | Hoffmann-La Roche, Inc. | Process for the manufacture of hydroxylated steroids |
| US4416985A (en) * | 1980-11-03 | 1983-11-22 | Schering, Aktiengesellschaft | Process for preparing 3β,7β-dihydroxy-Δ5 -steroids |
| US4614616A (en) * | 1980-11-03 | 1986-09-30 | Schering Aktiengesellschaft | Process for preparing 3β7β-dihydroxy-Δ5 -steroids |
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| US5981744A (en) * | 1995-12-11 | 1999-11-09 | G. D. Searle And Co. | Processes for preparation of 9,11-epoxy steroids and intermediates useful therein |
| US6046023A (en) * | 1995-12-12 | 2000-04-04 | Akzo Nobel, N.V. | Microbial 11α-hydroxylation of steroids |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057734A (zh) * | 2019-12-24 | 2020-04-24 | 天津科技大学 | 一种甲基睾丸素高效转化生产11α-羟基-甲基睾丸素的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2271636T3 (es) | 2007-04-16 |
| WO2004016640A2 (en) | 2004-02-26 |
| CA2495412A1 (en) | 2004-02-26 |
| US7002028B2 (en) | 2006-02-21 |
| BR0313523A (pt) | 2005-06-28 |
| MXPA05001857A (es) | 2005-06-03 |
| JP2006507369A (ja) | 2006-03-02 |
| EP1534732A2 (de) | 2005-06-01 |
| US20040220158A1 (en) | 2004-11-04 |
| WO2004016640A3 (en) | 2004-07-08 |
| AU2003285485A1 (en) | 2004-03-03 |
| TW200406419A (en) | 2004-05-01 |
| EP1534732B1 (de) | 2006-09-13 |
| DE60308388T2 (de) | 2007-09-20 |
| DE60308388D1 (de) | 2006-10-26 |
| ATE339437T1 (de) | 2006-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: PHARMACIA & UPJOHN COMPANY, MICHIGAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WHITE, MICHAEL J.;WUTS, PETER G.M.;BECK, DORIS;REEL/FRAME:013604/0846 Effective date: 20030421 |
|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |