GB1338547A - 17beta-tetrahydropyran-4-yloxy- steroids - Google Patents
17beta-tetrahydropyran-4-yloxy- steroidsInfo
- Publication number
- GB1338547A GB1338547A GB1577472A GB1577472A GB1338547A GB 1338547 A GB1338547 A GB 1338547A GB 1577472 A GB1577472 A GB 1577472A GB 1577472 A GB1577472 A GB 1577472A GB 1338547 A GB1338547 A GB 1338547A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydropyran
- yloxy
- compound
- acetoxy
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
Abstract
1338547 17#-(Tetrahydropyran-4-yloxy) steroids SYNTEX CORP 5 April 1972 [20 April 1971 3 Feb 1972] 15774/72 Heading C2U Novel steroids of the formulae wherein R<SP>1</SP> is H or CH 3 ; R<SP>2</SP> is H, CH 3 or C 2 H 5 ; R<SP>3</SP> is H or α- or #-CH 3 ; R<SP>4</SP> is =CHOH, H 2 or H(α-CH 3 ); and R<SP>6</SP> is H, C 1-8 alkyl or aryl are prepared from the coresponding 17#-ols and 4- halotetrahydropyrans. Alternatively an appropriate 3-keto-#<SP>4</SP>-17#-ol may be treated with 4- methoxy-5,6-dihydro-2H-pyran in the presence of an acid to give the corresponding 17#-(4- methoxy-tetrahydropyran-4-yl-oxy) compound, this then treated with an acid anhydride or acid chloride in the presence of sodium methoxide in dimethyl sulphoxide, the resulting 3-acyloxy- #<SP>3,5</SP>-compound reduced to the corresponding #<SP>5</SP>-3#-ol, this treated with LiAlH 4 and AlCl 3 to give the corresponding 3#-hydroxy-17#-(tetrahydropyran-4-yloxy)-#<SP>5</SP>-compound and this oxidized to the #<SP>4</SP>-3-one which may then be reduced under Birch conditions to the corresponding 5α-H compound, which can also be obtained by catalytic hydrogenation of the #<SP>5</SP>- 3#-ol and oxidation of the 5α-H-3#-ol thus produced. In variants of this process the treatment with the 4-methoxy-5,6-dihydro-2H- pyran and subsequent treatment with LiAlH 4 and AlCl 3 can be effected on a 3#-acyloxy-#<SP>5</SP>-17#- ol, with subsequent oxidation of the 17#- (tetrahydropyran-4-yloxy)-#<SP>5</SP>-3#-ol produced to the corresponding #<SP>4</SP>-3-one, or on a 3#- acyloxy-5α-H-17#-ol with intermediate hydrolysis of the 3#-acyloxy-17#-(4-methoxytetrahydropyran-4-yloxy)-5α-H compound to the 3#-ol and final oxidation of the 17#-(tetrahydropyran-4-yloxy)-5α-H-3#-ol to the corresponding 3-one. The last-named product may subsequently be treated with ethyl formate in a base to give the corresponding 2-hydroxymethylene compound which on hydrogenation gives the corresponding 2α-methyl compound. In the ring A aromatic series either of the above methods may be used to introduce the 17#- (tetrahydropyran-4-yloxy) grouping, and any resulting 3-acylate may be hydrolysed to the corresponding 3-ol which may then be reesterified. 3#-Acetoxy-5α-androstan-17#-ol is prepared by NaBH 4 reduction of 3#-acetoxy-5α-androstan- 17-one, prepared in turn by catalytic hydrogenation of 3#-acetoxyandrost-5-en-17-one. 3-Acetoxy-estra-1,3,5(10)-trien-17#-ol is prepared by reduction of 3-acetoxy-estra-1,3,5(10)- trien-17-one, in turn prepared by acylation of estra-1,3,5(10)-trien-3-ol-17-one. Similarly prepared are 3-acetoxy-18-methylestra-1,3,5(10)-trien 17#-ol and 3-acetoxy-18-ethylestra-1,3,5(10)-trien- 17#-ol. The novel steroids are stated variously to possess anabolic, androgenic, estrogenic and anti fertility activity, and they may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13575771A | 1971-04-20 | 1971-04-20 | |
US22333972A | 1972-02-03 | 1972-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1338547A true GB1338547A (en) | 1973-11-28 |
Family
ID=26833630
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1577472A Expired GB1338547A (en) | 1971-04-20 | 1972-04-05 | 17beta-tetrahydropyran-4-yloxy- steroids |
Country Status (3)
Country | Link |
---|---|
ES (1) | ES401765A1 (en) |
FR (1) | FR2133854B1 (en) |
GB (1) | GB1338547A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000066612A1 (en) * | 1999-05-04 | 2000-11-09 | Strakan Limited | Androgen glycosides and androgenic activity thereof |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1272102A (en) * | 1968-05-22 | 1972-04-26 | Syntex Corp | Steroid ethers |
-
1972
- 1972-04-05 GB GB1577472A patent/GB1338547A/en not_active Expired
- 1972-04-14 ES ES401765A patent/ES401765A1/en not_active Expired
- 1972-04-18 FR FR7213596A patent/FR2133854B1/fr not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000066612A1 (en) * | 1999-05-04 | 2000-11-09 | Strakan Limited | Androgen glycosides and androgenic activity thereof |
US6630453B1 (en) | 1999-05-04 | 2003-10-07 | Strakan Limited | Androgen derivatives and uses thereof |
Also Published As
Publication number | Publication date |
---|---|
FR2133854B1 (en) | 1975-06-20 |
FR2133854A1 (en) | 1972-12-01 |
DE2218000A1 (en) | 1972-10-26 |
DE2218000B2 (en) | 1976-04-08 |
ES401765A1 (en) | 1975-11-01 |
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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 |