GB1338547A - 17beta-tetrahydropyran-4-yloxy- steroids - Google Patents

17beta-tetrahydropyran-4-yloxy- steroids

Info

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
Application number
GB1577472A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Palo Alto LLC
Original Assignee
Roche Palo Alto LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roche Palo Alto LLC filed Critical Roche Palo Alto LLC
Publication of GB1338547A publication Critical patent/GB1338547A/en
Expired legal-status Critical Current

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

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.
GB1577472A 1971-04-20 1972-04-05 17beta-tetrahydropyran-4-yloxy- steroids Expired GB1338547A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1272102A (en) * 1968-05-22 1972-04-26 Syntex Corp Steroid ethers

Cited By (2)

* Cited by examiner, † Cited by third party
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
DE2218000B2 (en) 1976-04-08
DE2218000A1 (en) 1972-10-26
FR2133854B1 (en) 1975-06-20
ES401765A1 (en) 1975-11-01
FR2133854A1 (en) 1972-12-01

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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