GB1434919A - 3alpha-hydroxy androstanes - Google Patents
3alpha-hydroxy androstanesInfo
- Publication number
- GB1434919A GB1434919A GB2811872A GB2811872A GB1434919A GB 1434919 A GB1434919 A GB 1434919A GB 2811872 A GB2811872 A GB 2811872A GB 2811872 A GB2811872 A GB 2811872A GB 1434919 A GB1434919 A GB 1434919A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- cyano
- steroids
- androstan
- positions
- 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 abstract 4
- 150000000315 19-norandrostanes Chemical class 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 abstract 1
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- -1 di-substituted carbamoyl group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
1434919 3α-Hydroxy-steroids GLAXO LABORATORIES Ltd 15 June 1973 [15 June 1972] 28118/72 Heading C2U The invention comprises steroids of the androstane and 19-nor-androstane series possessa 3α-hydroxy group, a 17α-hydrogen atom and in position 17# as cyano, esterified carboxyl or mono- or di-substituted carbamoyl group, other than the steroids claimed in Specifications 1,380,248 and 1,380,246 and 3α-hydroxy-17#- methoxycarbonyl-5α and 5#-androstanes and 3α - hydroxy - 17# - methoxycarbonyl - 5#- androstan-11-one. The steroids, which may possess other substituents at other positions of the nucleus, e.g. the 2#-, 3#- and 11-positions, and which may be unsaturated, e.g. at the #<SP>8(9)</SP>, #<SP>1</SP> and #<SP>4</SP> positions, are prepared by the methods disclosed, inter alia, in Specification 1,380,246. Starting materials.-3α - Nitro - oxy - 17# - (2<SP>1</SP>- morpholinoethoxycarbonyl) - 5# - androstan - 11- one is prepared from the free 3α-hydroxy-17#- carboxylic acid by conversion to the 3-nitrate and esterification of this via the acid chloride. The corresponding 11-unsubstituted compounds are prepared similarly. The acid chlorides are converted to the corresponding 17#-cyano compounds via the 17#-carbamoyl compounds. 17#- Cyano - 5α - androstan - 3 - one and 17#- cyano-5α-androst-2-ene are prepared similarly and the latter is converted to 2#-bromo-17#- cyano - 3α - hydroxy - 5α - androstane via a 2,3-epoxide. The novel steroids possess anaesthetic properties and they may be made up into pharmaceutical compositions with suitable carriers, particularly aqueous solutions of parenterally acceptable non-ionic surface active agents.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2811872A GB1434919A (en) | 1972-06-15 | 1972-06-15 | 3alpha-hydroxy androstanes |
| FR7321743A FR2189034B2 (en) | 1972-06-15 | 1973-06-14 | |
| NL7308267A NL7308267A (en) | 1972-06-15 | 1973-06-14 | |
| CA174,050A CA1040619A (en) | 1972-06-15 | 1973-06-14 | Steroids of the androstane series, having anaesthetic activity |
| DK328673AA DK136157B (en) | 1972-06-15 | 1973-06-14 | Analogous process for the preparation of 3alpha-hydroxy-17beta-carboxylic acid derivatives of the androstane series or salts thereof. |
| BE132254A BE800899R (en) | 1972-06-15 | 1973-06-14 | ANDROSTANE SERIES COMPOUNDS WITH ANESTHESIC ACTIVITY AND THEIR PREPARATION |
| LU67790A LU67790A1 (en) | 1972-06-15 | 1973-06-14 | |
| DE2330342A DE2330342A1 (en) | 1972-06-15 | 1973-06-14 | STEROID CONNECTIONS |
| AU56937/73A AU477852B2 (en) | 1972-06-15 | 1973-06-14 | 3-hydroxy androstanes |
| ZA734037A ZA734037B (en) | 1972-06-15 | 1973-06-14 | Compounds of the androstane series having anaesthetic activity |
| US05/481,227 US3943124A (en) | 1970-12-17 | 1974-06-20 | Chemical compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2811872A GB1434919A (en) | 1972-06-15 | 1972-06-15 | 3alpha-hydroxy androstanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1434919A true GB1434919A (en) | 1976-05-12 |
Family
ID=10270562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2811872A Expired GB1434919A (en) | 1970-12-17 | 1972-06-15 | 3alpha-hydroxy androstanes |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE800899R (en) |
| CA (1) | CA1040619A (en) |
| DE (1) | DE2330342A1 (en) |
| DK (1) | DK136157B (en) |
| FR (1) | FR2189034B2 (en) |
| GB (1) | GB1434919A (en) |
| LU (1) | LU67790A1 (en) |
| NL (1) | NL7308267A (en) |
| ZA (1) | ZA734037B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117304245A (en) | 2013-04-17 | 2023-12-29 | 萨奇治疗股份有限公司 | 19-nor steroids that stimulate neural activity and methods of use thereof |
| US20160068563A1 (en) | 2013-04-17 | 2016-03-10 | Boyd L. Harrison | 19-nor neuroactive steroids and methods of use thereof |
| JP6470258B2 (en) | 2013-04-17 | 2019-02-13 | セージ セラピューティクス， インコーポレイテッド | 19-nor C 3, 3-disubstituted C21-N-pyrazolyl steroids and methods of use thereof |
| US9725481B2 (en) | 2013-04-17 | 2017-08-08 | Sage Therapeutics, Inc. | 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof |
| PT3021852T (en) | 2013-07-19 | 2021-04-21 | Sage Therapeutics Inc | Neuroactive steroids, compositions, and uses thereof |
| CN113750107B (en) | 2013-08-23 | 2025-02-11 | 萨奇治疗股份有限公司 | Neuroactive steroids, compositions and uses thereof |
| WO2015195962A1 (en) | 2014-06-18 | 2015-12-23 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| ES2808855T3 (en) | 2014-10-16 | 2021-03-02 | Sage Therapeutics Inc | Compositions and methods for treating CNS disorders |
| EP4527461A3 (en) | 2014-10-16 | 2025-06-25 | Sage Therapeutics, Inc. | A compound, compositions thereof and this compound for use in methods of treating cns disorders |
| WO2016082789A1 (en) | 2014-11-27 | 2016-06-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| LT3250210T (en) | 2015-01-26 | 2021-04-12 | Sage Therapeutics, Inc. | COMPOSITIONS AND METHODS FOR THE TREATMENT OF CNS DISORDERS |
| DK3258939T3 (en) | 2015-02-20 | 2022-12-12 | Sage Therapeutics Inc | NEUROACTIVE STEROIDS, COMPOSITIONS AND USES THEREOF |
| NZ790187A (en) | 2016-07-11 | 2025-08-29 | Sage Therapeutics Inc | C7, C12, and C16 substituted neuroactive steroids and their methods of use |
| NZ790226A (en) | 2016-07-11 | 2025-08-29 | Sage Therapeutics Inc | C17, C20, and C21 substituted neuroactive steroids and their methods of use |
| PE20230244A1 (en) | 2019-05-31 | 2023-02-07 | Sage Therapeutics Inc | NEUROACTIVE STEROIDS AND COMPOSITIONS THEREOF |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH273860A (en) * | 1942-04-25 | 1951-02-28 | Nv Organon | Process for the preparation of a compound of the cyclopentanopolyhydrophenanthrene series which contains an oxygen-containing group in ring C. |
| GB1380246A (en) * | 1970-12-17 | 1975-01-08 | Glaxo Lab Ltd | 3alpha-hydroxy-androstanes and esters thereof |
| BE776786A (en) * | 1970-12-17 | 1972-06-16 | Glaxo Lab Ltd | PREGNANE AND ANDROSTANE SERIES COMPOUNDS WITH ANESTHESIC ACTIVITY |
-
1972
- 1972-06-15 GB GB2811872A patent/GB1434919A/en not_active Expired
-
1973
- 1973-06-14 ZA ZA734037A patent/ZA734037B/en unknown
- 1973-06-14 NL NL7308267A patent/NL7308267A/xx not_active Application Discontinuation
- 1973-06-14 DE DE2330342A patent/DE2330342A1/en not_active Ceased
- 1973-06-14 FR FR7321743A patent/FR2189034B2/fr not_active Expired
- 1973-06-14 LU LU67790A patent/LU67790A1/xx unknown
- 1973-06-14 CA CA174,050A patent/CA1040619A/en not_active Expired
- 1973-06-14 DK DK328673AA patent/DK136157B/en unknown
- 1973-06-14 BE BE132254A patent/BE800899R/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL7308267A (en) | 1973-12-18 |
| LU67790A1 (en) | 1973-08-16 |
| ZA734037B (en) | 1974-05-29 |
| FR2189034A2 (en) | 1974-01-25 |
| FR2189034B2 (en) | 1977-01-21 |
| AU5693773A (en) | 1974-12-19 |
| DE2330342A1 (en) | 1974-01-17 |
| CA1040619A (en) | 1978-10-17 |
| BE800899R (en) | 1973-12-14 |
| DK136157C (en) | 1978-01-23 |
| DK136157B (en) | 1977-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |