GB1115635A - 13-alkylgonenes related to 19-norprogesterone - Google Patents
13-alkylgonenes related to 19-norprogesteroneInfo
- Publication number
- GB1115635A GB1115635A GB3026665A GB3026665A GB1115635A GB 1115635 A GB1115635 A GB 1115635A GB 3026665 A GB3026665 A GB 3026665A GB 3026665 A GB3026665 A GB 3026665A GB 1115635 A GB1115635 A GB 1115635A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compound
- ethyl
- give
- 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
- NVUUMOOKVFONOM-GPBSYSOESA-N 19-Norprogesterone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 NVUUMOOKVFONOM-GPBSYSOESA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000006027 Birch reduction reaction Methods 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- -1 hydroxymethylene Chemical group 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000005907 ketalization reaction Methods 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000001072 progestational effect Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of formula <FORM:1115635/C2/1> wherein X is a hydroxymethylene, carbonyl or ketalized carbonyl group, the hydrogen atoms at the 9, 8 and 14 positions have the trans-anti trans configuration with respect to the 13-ethyl group and the 10. hydrogen atom is cisto the 13-ethyl group, including racemates of 13b - and 13a -enantiomers, and their preparation by hydrolysis of a compound of formula <FORM:1115635/C2/2> wherein Y, in combination with unsaturation possible as shown, is a group hydrolysable to a keto group, or Y is a group hydrolysable to a hydroxy group in combination with an ethylenic bond terminating at the 5-position, followed where necessary or if desired by (a) 3-oxidation, (b) 20-oxidation, reduction, ketalization or ketal hydrolysis, or (c) acid isomerization to form the desired 4(5) double bond. 3 - Alkoxy - D 2,5(10) starting materials are prepared by Birch reduction of the corresponding 1,3,5(10)-trienes, optionally with 17-deacetoxylation. (\sB) - 17b - Acetoxy - 17a - acetyl - 13b - ethyl3 -methoxy-gona-1,3,5(10)-triene is prepared by acetylation of the corresponding 17b -hydroxy17a -ethynyl compound to give the 17b -acetoxy17a -ethynyl compound, reaction of this with N-bromo-acetamide to give the 17b -acetoxy-17a -dibromoacetyl compound, and treating this with zinc dust in acetic acid. (\sB) - 13b - Ethyl - 17b - (1 - hydroxyethyl) - 3 methoxy - gona - 1,3,5(10)-triene is prepared by reaction of the corresponding 17a -ethyl-17b -ol with phosphorus oxychloride to give the 17ethylidene compound, and treating this with diborane. The 20-keto compounds of the invention have progestational activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral, parenteral or rectal administration.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3026665A GB1115635A (en) | 1965-07-16 | 1965-07-16 | 13-alkylgonenes related to 19-norprogesterone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3026665A GB1115635A (en) | 1965-07-16 | 1965-07-16 | 13-alkylgonenes related to 19-norprogesterone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1115635A true GB1115635A (en) | 1968-05-29 |
Family
ID=10304922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3026665A Expired GB1115635A (en) | 1965-07-16 | 1965-07-16 | 13-alkylgonenes related to 19-norprogesterone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1115635A (en) |
-
1965
- 1965-07-16 GB GB3026665A patent/GB1115635A/en not_active Expired
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