GB1070044A - New steroid compound and novel intermediates useful in the preparation thereof - Google Patents
New steroid compound and novel intermediates useful in the preparation thereofInfo
- Publication number
- GB1070044A GB1070044A GB9407/66A GB940766A GB1070044A GB 1070044 A GB1070044 A GB 1070044A GB 9407/66 A GB9407/66 A GB 9407/66A GB 940766 A GB940766 A GB 940766A GB 1070044 A GB1070044 A GB 1070044A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- ethylthio
- methyl
- preparation
- novel intermediates
- 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
- -1 steroid compound Chemical class 0.000 title abstract 3
- 239000000543 intermediate Substances 0.000 title 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 2
- ZVUZCNRYILDRQB-RZUHSPRBSA-N (5R,7R,8R,9S,10S,13S,14S,17S)-7-ethylsulfanyl-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C(C)S[C@H]1[C@H]2[C@@H]3CC[C@]([C@@]3(C)CC[C@@H]2[C@]2(CC(C(C[C@@H]2C1)=O)=CO)C)(C)O ZVUZCNRYILDRQB-RZUHSPRBSA-N 0.000 abstract 1
- BSEUVDXFCVEESF-KAKDVIIHSA-N (7R,8R,9S,10R,13S,14S,17S)-7-ethylsulfanyl-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one Chemical compound C(C)S[C@H]1[C@H]2[C@@H]3CC[C@]([C@@]3(C)CC[C@@H]2[C@]2(CCC(C=C2C1)=O)C)(C)O BSEUVDXFCVEESF-KAKDVIIHSA-N 0.000 abstract 1
- 230000001195 anabolic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Novel compounds of the formula <FORM:1070044/C2/1> wherein X represents two hydrogen atoms or a hydroxymethylene group and Y represents an oxygen atom, or X and Y together represent the group <FORM:1070044/C2/2> are obtained by reducing the double bond in 7a - ethylthio - 17b - hydroxy - 17a - methylandrost - 4 - en - 3 - one to give 7a - ethyl thio - 17b - hydroxy - 17a - methyl - 5a - androstan-3-one, reacting the latter with an alkyl formate under strong basic conditions to obtain 7a - ethylthio - 17b - hydroxy - 2 - hydroxymethylene - 17a - methyl - 5a - androstan-3-one and reacting the latter with hydrazine to give 7a - ethylthio - 17b - hydroxy - 17a - methyl - 5a - androstano - [3,2,c] pyrazole. Pharmaceutical compositions having anabolic activity and containing the above pyrazole are administered orally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1229465 | 1965-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1070044A true GB1070044A (en) | 1967-05-24 |
Family
ID=11801296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9407/66A Expired GB1070044A (en) | 1965-03-03 | 1966-03-03 | New steroid compound and novel intermediates useful in the preparation thereof |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1568372C3 (en) |
| FR (1) | FR7296M (en) |
| GB (1) | GB1070044A (en) |
-
1966
- 1966-03-01 DE DE1568372A patent/DE1568372C3/en not_active Expired
- 1966-03-03 FR FR51902A patent/FR7296M/fr not_active Expired
- 1966-03-03 GB GB9407/66A patent/GB1070044A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1568372B2 (en) | 1974-09-12 |
| DE1568372C3 (en) | 1975-05-28 |
| DE1568372A1 (en) | 1970-03-19 |
| FR7296M (en) | 1969-09-29 |
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