GB1424212A - Process for the manufacture of 16,17-unsaturated steroids - Google Patents
Process for the manufacture of 16,17-unsaturated steroidsInfo
- Publication number
- GB1424212A GB1424212A GB682073A GB682073A GB1424212A GB 1424212 A GB1424212 A GB 1424212A GB 682073 A GB682073 A GB 682073A GB 682073 A GB682073 A GB 682073A GB 1424212 A GB1424212 A GB 1424212A
- Authority
- GB
- United Kingdom
- Prior art keywords
- steroids
- formula
- acid
- feb
- prepared
- 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.)
- Expired
Links
- 150000003431 steroids Chemical class 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- -1 C2U Steroids Chemical class 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- UOQFZGVGGMHGEE-UHFFFAOYSA-N 1,1-dihydroxypropan-2-one Chemical group CC(=O)C(O)O UOQFZGVGGMHGEE-UHFFFAOYSA-N 0.000 abstract 1
- QRFGDGZPNFSNCE-UHFFFAOYSA-N 2-hydroxyprop-2-enal Chemical compound OC(=C)C=O QRFGDGZPNFSNCE-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207420A DE2207420A1 (de) | 1972-02-11 | 1972-02-11 | Verfahren zur herstellung von 16,17ungesaettigten steroiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1424212A true GB1424212A (en) | 1976-02-11 |
Family
ID=5836210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB682073A Expired GB1424212A (en) | 1972-02-11 | 1973-02-12 | Process for the manufacture of 16,17-unsaturated steroids |
Country Status (15)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4216159A (en) * | 1978-05-25 | 1980-08-05 | The Upjohn Company | Synthesis of 16-unsaturated pregnanes from 17-keto steroids |
| DE3852252T2 (de) * | 1987-09-11 | 1995-04-06 | Nippon Zeon Co | Verfahren zur Herstellung einer alpha-acyloxy-alpha-beta-ungesättigten Verbindung und eines 20-acyloxy-17(20)-methylen-21-al-steroidderivats. |
| US5169966A (en) * | 1987-09-11 | 1992-12-08 | Nippon Zeon Co., Ltd | Process for producing an α-acyloxy-α, β-unsaturated carbonyl compound and a 20-acyloxy-17(20)-methylen-21-al-steroid compound |
| CN103739647B (zh) * | 2008-05-28 | 2017-06-09 | 雷沃根生物医药有限公司 | 用于治疗疾病的NF‑κB的非激素甾体调节剂 |
| EP2556083A4 (en) | 2010-04-05 | 2013-12-04 | Validus Biopharma Inc | NONHORMONAL STEROID MODULATORS OF NF-KAPPA-B FOR DISEASE TREATMENT |
| CN102603843B (zh) * | 2012-02-20 | 2013-07-31 | 湖南诺凯生物医药有限公司 | 一种地塞米松中间体的制备方法 |
| 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 |
-
0
- BE BE795243D patent/BE795243A/xx unknown
-
1972
- 1972-02-11 DE DE2207420A patent/DE2207420A1/de active Pending
-
1973
- 1973-01-17 DD DD168292A patent/DD100942A5/xx unknown
- 1973-01-29 DK DK48373*#A patent/DK131942C/da active
- 1973-01-30 CS CS722A patent/CS165381B2/cs unknown
- 1973-02-07 AU AU51931/73A patent/AU468856B2/en not_active Expired
- 1973-02-08 AT AT112373A patent/AT328102B/de not_active IP Right Cessation
- 1973-02-09 HU HUSE1665A patent/HU165442B/hu unknown
- 1973-02-09 FR FR7304677A patent/FR2171374B1/fr not_active Expired
- 1973-02-09 CH CH186473A patent/CH586719A5/xx not_active IP Right Cessation
- 1973-02-09 US US00331060A patent/US3842105A/en not_active Expired - Lifetime
- 1973-02-12 GB GB682073A patent/GB1424212A/en not_active Expired
- 1973-02-12 JP JP48017358A patent/JPS4886854A/ja active Pending
- 1973-02-12 NL NL7301975A patent/NL7301975A/xx not_active Application Discontinuation
- 1973-02-12 SE SE7301934A patent/SE385591B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS165381B2 (US06826419-20041130-M00005.png) | 1975-12-22 |
| HU165442B (US06826419-20041130-M00005.png) | 1974-08-28 |
| DD100942A5 (US06826419-20041130-M00005.png) | 1973-10-12 |
| DK131942C (da) | 1976-02-23 |
| AU468856B2 (en) | 1976-01-22 |
| CH586719A5 (US06826419-20041130-M00005.png) | 1977-04-15 |
| ATA112373A (de) | 1975-05-15 |
| NL7301975A (US06826419-20041130-M00005.png) | 1973-08-14 |
| AT328102B (de) | 1976-03-10 |
| JPS4886854A (US06826419-20041130-M00005.png) | 1973-11-15 |
| SE385591B (sv) | 1976-07-12 |
| BE795243A (fr) | 1973-08-09 |
| DE2207420A1 (de) | 1973-08-16 |
| DK131942B (da) | 1975-09-29 |
| FR2171374A1 (US06826419-20041130-M00005.png) | 1973-09-21 |
| US3842105A (en) | 1974-10-15 |
| AU5193173A (en) | 1974-08-08 |
| FR2171374B1 (US06826419-20041130-M00005.png) | 1976-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |