CA2419960A1 - Method for the preparation of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) - Google Patents
Method for the preparation of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) Download PDFInfo
- Publication number
- CA2419960A1 CA2419960A1 CA002419960A CA2419960A CA2419960A1 CA 2419960 A1 CA2419960 A1 CA 2419960A1 CA 002419960 A CA002419960 A CA 002419960A CA 2419960 A CA2419960 A CA 2419960A CA 2419960 A1 CA2419960 A1 CA 2419960A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- oxidoprogesterone
- dichloromethane
- derivative
- acid
- 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
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title description 5
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 6
- 239000010452 phosphate Substances 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- MDJRZSNPHZEMJH-MTMZYOSNSA-N artisone acetate Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 MDJRZSNPHZEMJH-MTMZYOSNSA-N 0.000 claims description 8
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- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims description 8
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- 230000000397 acetylating effect Effects 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00119494.3 | 2000-09-18 | ||
| EP00119494 | 2000-09-18 | ||
| PCT/EP2001/010734 WO2002022646A2 (en) | 2000-09-18 | 2001-09-17 | Method for the preparation of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2419960A1 true CA2419960A1 (en) | 2002-03-21 |
Family
ID=8169774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002419960A Abandoned CA2419960A1 (en) | 2000-09-18 | 2001-09-17 | Method for the preparation of 21-hydroxy-6,19-oxidoprogesterone (21oh-6op) |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US7071328B2 (https=) |
| EP (1) | EP1325022B1 (https=) |
| JP (1) | JP2004509131A (https=) |
| AT (1) | ATE344273T1 (https=) |
| AU (2) | AU1817902A (https=) |
| CA (1) | CA2419960A1 (https=) |
| DE (1) | DE60124289T2 (https=) |
| DK (1) | DK1325022T3 (https=) |
| ES (1) | ES2271090T3 (https=) |
| IL (2) | IL154776A0 (https=) |
| PT (1) | PT1325022E (https=) |
| SI (1) | SI1325022T1 (https=) |
| WO (1) | WO2002022646A2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1325022T1 (sl) * | 2000-09-18 | 2007-04-30 | Applied Research Systems | Metoda za pripravo 21-hidroksi-6,19-oksidoprogesterona (21oh-6op) |
| SI1330468T1 (sl) * | 2000-09-18 | 2007-10-31 | Serono Lab | Ĺ˝veplovi analogi 21-hidroksi-6,19-oksido-progesterona (21oh-6op) za zdravljenje preseĺ˝ka glukokortikoidov |
| WO2007106385A2 (en) * | 2006-03-10 | 2007-09-20 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Use of a ghrelin agonist to improve the catabolic effects of glucocorticoid treatment |
| EP1862468A1 (de) * | 2006-06-02 | 2007-12-05 | Bayer Schering Pharma Aktiengesellschaft | Kristallines 11beta-(4-Acetylphenyl)-20,20,21,21,21-pentafluor-17-hydroxy-19-nor-17alpha-pregna-4,9-dien-3-on |
| DE102009034367A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-benzyliden-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| DE102009034366A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-methylenoxyalkylenaryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034362A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034368A1 (de) | 2009-07-20 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-acyloxyalkylenphenyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034525A1 (de) | 2009-07-21 | 2011-01-27 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-aryl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Behandlung von Krankheiten |
| DE102009034526A1 (de) | 2009-07-21 | 2011-02-10 | Bayer Schering Pharma Aktiengesellschaft | 17-Hydroxy-17-pentafluorethyl-estra-4,9(10)-dien-11-ethinylphenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Behandlung von Krankheiten |
| DE102010007722A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
| DE102010007719A1 (de) | 2010-02-10 | 2011-08-11 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Progesteronrezeptorantagonisten |
| MX2015004606A (es) | 2012-10-09 | 2017-04-04 | Avery Dennison Corp | Adhesivos y metodos relacionados. |
| US20210355154A1 (en) * | 2018-09-28 | 2021-11-18 | The Regents Of The University Of Michigan | Halogenated Cholesterol Analogues and Methods of Making and Using Same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036068A (en) * | 1960-01-06 | 1962-05-22 | Syntex Sa | C-6, 19-steroidal lactones |
| LU77457A1 (https=) * | 1977-05-31 | 1979-01-19 | ||
| US4814333A (en) * | 1987-07-28 | 1989-03-21 | The Trustees Of Dartmouth College | Method for treatment of hypercortisolemic, depressed patients |
| GB9606016D0 (en) * | 1996-03-22 | 1996-05-22 | Smithkline Beecham Plc | Novel use |
| EP0903146A1 (en) * | 1997-09-23 | 1999-03-24 | Applied Research Systems ARS Holdings N.V. | 21-Hydroy-6,19-oxidoprogesterone (210h-60p) as antiglucocorticoid |
| ATE332696T1 (de) * | 1997-10-06 | 2006-08-15 | Univ Leland Stanford Junior | Methode zur behandlung von durch glycocorticoidstörungen verursachten psychosen |
| SI1330468T1 (sl) * | 2000-09-18 | 2007-10-31 | Serono Lab | Ĺ˝veplovi analogi 21-hidroksi-6,19-oksido-progesterona (21oh-6op) za zdravljenje preseĺ˝ka glukokortikoidov |
| SI1325022T1 (sl) * | 2000-09-18 | 2007-04-30 | Applied Research Systems | Metoda za pripravo 21-hidroksi-6,19-oksidoprogesterona (21oh-6op) |
-
2001
- 2001-09-17 SI SI200130675T patent/SI1325022T1/sl unknown
- 2001-09-17 DE DE60124289T patent/DE60124289T2/de not_active Expired - Fee Related
- 2001-09-17 AU AU1817902A patent/AU1817902A/xx active Pending
- 2001-09-17 CA CA002419960A patent/CA2419960A1/en not_active Abandoned
- 2001-09-17 US US10/380,167 patent/US7071328B2/en not_active Expired - Fee Related
- 2001-09-17 AU AU2002218179A patent/AU2002218179B2/en not_active Ceased
- 2001-09-17 ES ES01984642T patent/ES2271090T3/es not_active Expired - Lifetime
- 2001-09-17 EP EP01984642A patent/EP1325022B1/en not_active Expired - Lifetime
- 2001-09-17 IL IL15477601A patent/IL154776A0/xx active IP Right Grant
- 2001-09-17 DK DK01984642T patent/DK1325022T3/da active
- 2001-09-17 WO PCT/EP2001/010734 patent/WO2002022646A2/en not_active Ceased
- 2001-09-17 JP JP2002526897A patent/JP2004509131A/ja active Pending
- 2001-09-17 AT AT01984642T patent/ATE344273T1/de not_active IP Right Cessation
- 2001-09-17 PT PT01984642T patent/PT1325022E/pt unknown
-
2003
- 2003-03-05 IL IL154776A patent/IL154776A/en not_active IP Right Cessation
-
2005
- 2005-06-01 US US11/141,029 patent/US20050277769A1/en not_active Abandoned
-
2007
- 2007-04-12 US US11/734,628 patent/US20070249826A1/en not_active Abandoned
-
2009
- 2009-02-09 US US12/367,859 patent/US20090216008A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ATE344273T1 (de) | 2006-11-15 |
| ES2271090T3 (es) | 2007-04-16 |
| AU2002218179B2 (en) | 2006-11-16 |
| AU1817902A (en) | 2002-03-26 |
| SI1325022T1 (sl) | 2007-04-30 |
| EP1325022B1 (en) | 2006-11-02 |
| PT1325022E (pt) | 2006-12-29 |
| WO2002022646A2 (en) | 2002-03-21 |
| IL154776A (en) | 2007-07-04 |
| WO2002022646A3 (en) | 2002-06-06 |
| JP2004509131A (ja) | 2004-03-25 |
| DE60124289T2 (de) | 2007-09-06 |
| US20050277769A1 (en) | 2005-12-15 |
| US20040092733A1 (en) | 2004-05-13 |
| US20090216008A1 (en) | 2009-08-27 |
| DK1325022T3 (da) | 2007-02-19 |
| EP1325022A2 (en) | 2003-07-09 |
| IL154776A0 (en) | 2003-10-31 |
| US7071328B2 (en) | 2006-07-04 |
| WO2002022646A9 (en) | 2002-09-19 |
| DE60124289D1 (de) | 2006-12-14 |
| US20070249826A1 (en) | 2007-10-25 |
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| EEER | Examination request | ||
| FZDE | Discontinued |