GB1297962A - - Google Patents
Info
- Publication number
- GB1297962A GB1297962A GB1297962DA GB1297962A GB 1297962 A GB1297962 A GB 1297962A GB 1297962D A GB1297962D A GB 1297962DA GB 1297962 A GB1297962 A GB 1297962A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dien
- methoxy
- alkyl
- propadienyl
- compounds
- 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
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
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)
Abstract
1297962 17α-Propadienyl steroids SANDOZ Ltd 14 Nov 1969 [25 Nov 1968] 55842/69 Heading C2U The invention comprises compounds of formula wherein R 1 is C 1-3 alkyl; R 2 is H, Me or C 2-4 alkanoyl; R 4 is H, OH or C 2-4 alkanoyloxy; and Z, embracing rings A and B and the substituents thereon, represents one of the groups Z1 to Z9 wherein R 5 is H, C 1-3 alkyl, C 5-7 cycloalkyl or C 2-4 alkanoyl; R 6 is H, 6α-Me or 7α-Me; R 7 is H or Me; and R 8 is H, Me, F or C1; with the exclusion of: (i) 3,16α,17#-trihydroxy-17α-propadienyl - 13# - alkylgona - 1,3,5(10) - trienes (unsubstituted at the 6- and 7-positions) and esters thereof (see Specification 1,229,262); (ii) 17α- propadienyl - 17# - hydroxyestra - 4,9 - dien - 3- one (see Specification 1,297,963); (iii) 17α-propadienyl - 17# - hydroxyestr - 4 - en - 3 - one (see Specification 1,297,964); and (iv) 3#-acetoxy- 17α - propadienylestr - 4 - en - 17# - ol (see Specification 1,297,964). Preparation of compounds Ih is by complex metal hydride reduction of corresponding compounds having in the 17α-position the group -[C#C-CH 2 -NRR<SP>1</SP>R<SP>11</SP>]<SP>+</SP>.Y<SP>-</SP> (where R, R<SP>1</SP>. and R<SP>11</SP> are each C 1-3 alkyl, or R is C 1-3 alkyl and NR<SP>1</SP>R<SP>11</SP> is pyrrolidino or piperidino, and Y is Cl, Br, I, OSO 2 Me or O-tosyl) and in the 17#- position a free hydroxyl group, followed when required by 3,16- and/or 17-esterification or 17- O-methylation. The starting material is optionally protected, e.g. as a 3-methoxy-#<SP>2,5(10)</SP>- compound, in which case a deprotection step must follow the metal hydride reduction. 3 - Methoxy - 17α - (3 - dimethylamino - 1- propynyl)estra - 1,3,5(10) - trien - 17# - ol and its methiodide are prepared from the corresponding 17α-ethynyl compound. 3 - Methoxy - 17α - propadienylestra - 2,5(10)- dien-17#-ol is prepared from 3-methoxyestra-2- 5(10) - dien - 17 - one via 3 - methoxy - 17α - (3, dimethylamino - 1 - propynyl)estra - 2,5(10)- dien-17#-ol and the methiodide thereof. Compounds Ih are said to possess estrogenic and progestational activities, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration. Reference has been directed by the Comptroller to Specification 1,222,886.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77877768A | 1968-11-25 | 1968-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1297962A true GB1297962A (en) | 1972-11-29 |
Family
ID=25114361
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1297962D Expired GB1297962A (en) | 1968-11-25 | 1969-11-14 | |
| GB1297963D Expired GB1297963A (en) | 1968-11-25 | 1969-11-14 | |
| GB1297964D Expired GB1297964A (en) | 1968-11-25 | 1969-11-14 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1297963D Expired GB1297963A (en) | 1968-11-25 | 1969-11-14 | |
| GB1297964D Expired GB1297964A (en) | 1968-11-25 | 1969-11-14 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS4826005B1 (en) |
| AT (1) | AT330966B (en) |
| BE (1) | BE742137A (en) |
| BR (1) | BR6914427D0 (en) |
| CA (1) | CA958005A (en) |
| CH (3) | CH579101A5 (en) |
| CS (5) | CS150690B2 (en) |
| DE (1) | DE1966922A1 (en) |
| DK (1) | DK127107B (en) |
| ES (2) | ES387606A1 (en) |
| FI (4) | FI47349C (en) |
| FR (1) | FR2024166B1 (en) |
| GB (3) | GB1297962A (en) |
| HU (1) | HU164121B (en) |
| NL (1) | NL149815B (en) |
| NO (1) | NO134058C (en) |
| PL (5) | PL80336B1 (en) |
| SE (2) | SE369076B (en) |
| SU (3) | SU402209A3 (en) |
| YU (1) | YU34534B (en) |
| ZA (1) | ZA698233B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH571537A5 (en) * | 1970-04-24 | 1976-01-15 | Sandoz Ag | |
| CH558346A (en) * | 1971-06-17 | 1975-01-31 | Sandoz Ag | METHOD FOR PRODUCING NEW 3-OXIMINO-17 (ALPHA) -PROPADIENYL-SUBSTITUTED STEROIDS. |
| JPS5196702U (en) * | 1975-01-31 | 1976-08-03 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392166A (en) * | 1966-03-30 | 1968-07-09 | Syntex Corp | Androst-4-enes and estr-4-enes having a 17alpha-diethylenically unsaturated side chain |
| US3385871A (en) * | 1965-12-15 | 1968-05-28 | Syntex Corp | Halogenated cyclopropyl and cyclopropenyl estratrienes and process for their preparation |
-
1969
- 1969-02-24 SU SU1617457A patent/SU402209A3/ru active
- 1969-11-13 CH CH1695569A patent/CH579101A5/xx not_active IP Right Cessation
- 1969-11-13 CH CH208573A patent/CH580115A5/xx unknown
- 1969-11-13 CH CH208473A patent/CH571538A5/xx not_active IP Right Cessation
- 1969-11-14 GB GB1297962D patent/GB1297962A/en not_active Expired
- 1969-11-14 GB GB1297963D patent/GB1297963A/en not_active Expired
- 1969-11-14 GB GB1297964D patent/GB1297964A/en not_active Expired
- 1969-11-14 NL NL696917209A patent/NL149815B/en not_active IP Right Cessation
- 1969-11-20 DK DK615769AA patent/DK127107B/en unknown
- 1969-11-20 YU YU2911/69A patent/YU34534B/en unknown
- 1969-11-21 FI FI693387A patent/FI47349C/en active
- 1969-11-21 DE DE19691966922 patent/DE1966922A1/en active Pending
- 1969-11-24 BE BE742137D patent/BE742137A/xx unknown
- 1969-11-24 CS CS7721A patent/CS150690B2/cs unknown
- 1969-11-24 SU SU1615145A patent/SU390714A3/ru active
- 1969-11-24 CS CS7196A patent/CS150694B2/cs unknown
- 1969-11-24 SE SE16102/69A patent/SE369076B/xx unknown
- 1969-11-24 CS CS7195A patent/CS150693B2/cs unknown
- 1969-11-24 BR BR214427/69A patent/BR6914427D0/en unknown
- 1969-11-24 PL PL1969137088A patent/PL80336B1/en unknown
- 1969-11-24 FR FR6940364A patent/FR2024166B1/fr not_active Expired
- 1969-11-24 PL PL1969156777A patent/PL82605B1/en unknown
- 1969-11-24 PL PL1969156783A patent/PL82690B1/en unknown
- 1969-11-24 HU HUSA2027A patent/HU164121B/hu unknown
- 1969-11-24 SU SU1380086A patent/SU390715A3/ru active
- 1969-11-24 PL PL1969156778A patent/PL82606B1/en unknown
- 1969-11-24 CS CS7193A patent/CS150691B2/cs unknown
- 1969-11-24 CS CS7194A patent/CS150692B2/cs unknown
- 1969-11-24 NO NO4651/69A patent/NO134058C/no unknown
- 1969-11-24 SE SE7301830A patent/SE378605B/xx unknown
- 1969-11-24 JP JP44093688A patent/JPS4826005B1/ja active Pending
- 1969-11-24 PL PL1969156780A patent/PL82607B1/en unknown
- 1969-11-24 CA CA068,167A patent/CA958005A/en not_active Expired
- 1969-11-24 AT AT1096369A patent/AT330966B/en not_active IP Right Cessation
-
1970
- 1970-11-25 ZA ZA698233A patent/ZA698233B/en unknown
-
1971
- 1971-01-26 ES ES0387606A patent/ES387606A1/en not_active Expired
- 1971-01-26 ES ES0387605A patent/ES387605A1/en not_active Expired
-
1972
- 1972-08-23 FI FI722331A patent/FI48347C/en active
- 1972-08-23 FI FI722332A patent/FI47350C/en active
-
1973
- 1973-04-18 FI FI731256A patent/FI48583C/en active
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |