DK0608178T3 - Fremgangsmåde til 16 alfa-methylering af steroider - Google Patents
Fremgangsmåde til 16 alfa-methylering af steroiderInfo
- Publication number
- DK0608178T3 DK0608178T3 DK94400114.8T DK94400114T DK0608178T3 DK 0608178 T3 DK0608178 T3 DK 0608178T3 DK 94400114 T DK94400114 T DK 94400114T DK 0608178 T3 DK0608178 T3 DK 0608178T3
- Authority
- DK
- Denmark
- Prior art keywords
- alpha
- hydrogen
- beta
- optionally
- residue
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000007069 methylation reaction Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000002085 enols Chemical class 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012022 methylating agents Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9300519A FR2700548B1 (fr) | 1993-01-20 | 1993-01-20 | Nouveau procédé de préparation de stéroïdes 16 alpha-méthylés. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK0608178T3 true DK0608178T3 (da) | 1996-10-07 |
Family
ID=9443202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK94400114.8T DK0608178T3 (da) | 1993-01-20 | 1994-01-19 | Fremgangsmåde til 16 alfa-methylering af steroider |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5508452A (da) |
| EP (1) | EP0608178B1 (da) |
| JP (1) | JP3535555B2 (da) |
| KR (1) | KR100284824B1 (da) |
| CN (1) | CN1040647C (da) |
| AT (1) | ATE140924T1 (da) |
| AU (1) | AU667147B2 (da) |
| CA (1) | CA2113776C (da) |
| DE (1) | DE69400340T2 (da) |
| DK (1) | DK0608178T3 (da) |
| ES (1) | ES2091095T3 (da) |
| FR (1) | FR2700548B1 (da) |
| GR (1) | GR3020751T3 (da) |
| HU (1) | HU221320B1 (da) |
| RU (1) | RU2127278C1 (da) |
| UA (1) | UA44887C2 (da) |
| ZA (1) | ZA94405B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6040468A (en) * | 1996-10-25 | 2000-03-21 | Alcon Laboratories, Inc. | Method of preparing 16α, 17α-dialkylated steroids |
| US6841665B2 (en) | 2000-02-18 | 2005-01-11 | The University Of Hong Kong | Method for synthesizing 5β, 6β-epoxides of steroids by a highly β-selective epoxidation of ΔΔ5-unsaturated steroids catalyzed by ketones |
| DK2444092T3 (da) | 2008-05-28 | 2015-09-28 | Reveragen Biopharma Inc | Ikke-hormonelle steroidmodulatorer af nf-kb til behandling af sygdom |
| EP2556083A4 (en) | 2010-04-05 | 2013-12-04 | Validus Biopharma Inc | NONHORMONAL STEROID MODULATORS OF NF-KAPPA-B FOR DISEASE TREATMENT |
| WO2017004205A1 (en) | 2015-06-29 | 2017-01-05 | Reveragen Biopharma, Inc. | NON-HORMONAL STEROID MODULATORS OF NF-κB FOR TREATMENT OF DISEASE |
| US11382922B2 (en) | 2019-03-07 | 2022-07-12 | Reveragen Biopharma, Inc. | Aqueous oral pharmaceutical suspension compositions |
| CN115322242B (zh) * | 2022-09-14 | 2023-09-12 | 山东赛托生物科技股份有限公司 | 一种高品质甾体药物中间体的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE28369E (en) * | 1957-02-27 | 1975-03-18 | Atcc-zxs | |
| US3080393A (en) * | 1960-02-04 | 1963-03-05 | Syntex Corp | Process for preparing 16alpha-methyl-17alpha-hydroxy-20-keto-pregnanes from the corresponding 16-dehydro-20-keto pregnanes |
| JPS504657B1 (da) * | 1968-07-30 | 1975-02-22 | ||
| US4022769A (en) * | 1974-05-13 | 1977-05-10 | Richardson-Merrell Inc. | Androst-4-en-19-ones |
| NL7607283A (nl) * | 1975-07-23 | 1977-01-25 | Merck & Co Inc | Werkwijze voor het bereiden van nieuwe pregnaansteroiden. |
| US4277409A (en) * | 1977-03-18 | 1981-07-07 | Roussel Uclaf | Preparation of 9α-fluoro-16α-methyl-21-acetoxy-Δ1,4 -pregnadiene-11β-ol-3,20-dione |
| DD225595A3 (de) * | 1982-10-01 | 1985-07-31 | Jenapharm Veb | Verfahren zur herstellung von 11 beta-hydroxysteroiden aus 11 beta-acyloxysteroiden |
| US4990612A (en) * | 1984-06-11 | 1991-02-05 | The Upjohn Company | 16α-methylation process |
| JPS611699A (ja) * | 1984-06-11 | 1986-01-07 | ジ アツプジヨン カンパニー | １６α‐メチル化法 |
| US4704455A (en) * | 1984-06-11 | 1987-11-03 | The Upjohn Company | 16α-methylatedΔ17(20)-corticoids |
| KR960011781B1 (ko) * | 1986-06-04 | 1996-08-30 | 디 엎죤 캄파니 | 16α-메틸화 공정 |
| US4772755A (en) * | 1987-03-19 | 1988-09-20 | Mcneilab, Inc. | 1,2-1,4 addition reaction sequence leading to disubstituted acelylenes |
| FR2643638B1 (fr) * | 1989-02-24 | 1991-06-14 | Roussel Uclaf | Nouveaux 19-nor steroides ayant en position 11beta une chaine carbonee comportant une fonction amide ou carbamate, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| FR2692266B1 (fr) * | 1992-06-11 | 1994-08-05 | Roussel Uclaf | Nouveau procede de preparation de sterouides 16 alpha-methyles. |
-
1993
- 1993-01-20 FR FR9300519A patent/FR2700548B1/fr not_active Expired - Fee Related
-
1994
- 1994-01-12 US US08/180,454 patent/US5508452A/en not_active Expired - Lifetime
- 1994-01-19 KR KR1019940000937A patent/KR100284824B1/ko not_active Expired - Lifetime
- 1994-01-19 DE DE69400340T patent/DE69400340T2/de not_active Expired - Lifetime
- 1994-01-19 AT AT94400114T patent/ATE140924T1/de active
- 1994-01-19 JP JP01776294A patent/JP3535555B2/ja not_active Expired - Lifetime
- 1994-01-19 RU RU94001576A patent/RU2127278C1/ru active
- 1994-01-19 AU AU53847/94A patent/AU667147B2/en not_active Expired
- 1994-01-19 HU HU9400156A patent/HU221320B1/hu unknown
- 1994-01-19 ES ES94400114T patent/ES2091095T3/es not_active Expired - Lifetime
- 1994-01-19 CA CA002113776A patent/CA2113776C/fr not_active Expired - Lifetime
- 1994-01-19 DK DK94400114.8T patent/DK0608178T3/da active
- 1994-01-19 CN CN94101077A patent/CN1040647C/zh not_active Expired - Lifetime
- 1994-01-19 EP EP94400114A patent/EP0608178B1/fr not_active Expired - Lifetime
- 1994-01-19 UA UA94005065A patent/UA44887C2/uk unknown
- 1994-01-20 ZA ZA94405A patent/ZA94405B/xx unknown
-
1996
- 1996-08-08 GR GR960400219T patent/GR3020751T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5508452A (en) | 1996-04-16 |
| ES2091095T3 (es) | 1996-10-16 |
| CN1103643A (zh) | 1995-06-14 |
| ATE140924T1 (de) | 1996-08-15 |
| HU9400156D0 (en) | 1994-05-30 |
| AU5384794A (en) | 1994-07-28 |
| FR2700548B1 (fr) | 1995-03-03 |
| ZA94405B (en) | 1995-01-20 |
| HUT66233A (en) | 1994-10-28 |
| KR100284824B1 (ko) | 2001-03-15 |
| UA44887C2 (uk) | 2002-03-15 |
| JPH06293791A (ja) | 1994-10-21 |
| CN1040647C (zh) | 1998-11-11 |
| HU221320B1 (en) | 2002-09-28 |
| RU2127278C1 (ru) | 1999-03-10 |
| DE69400340T2 (de) | 1997-01-23 |
| JP3535555B2 (ja) | 2004-06-07 |
| GR3020751T3 (en) | 1996-11-30 |
| FR2700548A1 (fr) | 1994-07-22 |
| EP0608178B1 (fr) | 1996-07-31 |
| CA2113776A1 (fr) | 1994-07-21 |
| DE69400340D1 (de) | 1996-09-05 |
| CA2113776C (fr) | 2004-10-05 |
| KR940018396A (ko) | 1994-08-16 |
| EP0608178A1 (fr) | 1994-07-27 |
| AU667147B2 (en) | 1996-03-07 |
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