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US4147695A
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11β-Substituted-Δ9 -steroids
Assignee: Sanofi Aventis France
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Filing: 1978-01-06
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Granted: 1979-04-03
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Expires: 1998-01-06
Abstract
Abstract Novel 11β-substituted-Δ 9 -ene-5α-ols of the formula ##STR1## wherein K is a blocked ketone in the form of a ketal, thio-ketal or methyloxime, X is a pentagonal or hexagonal ring optionally substituted, R 1 is selected from the group consisting of branched and straight chain alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted, optionally substituted aryl of 6 to 12 carbon atoms, optionally substituted aralkyl of 7 to 13 carbon atoms and heterocycle with at least one hetero oxygen or sulfur atom and R 2 is alkyl of 1 to 4 carbon atoms which are useful intermediates and a process for their preparation.
Inventors
- 👤 Jean G. Teutsch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 21:44
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0051; C07J1/0081; C07J1/0088; C07J1/0096; C07J1/0059; C07J21/00; C07J21/005; C07J21/006; C07J33/00; C07J33/002; C07J51/00; C07J71/00; C07J71/0005; C07J71/001
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
238 words
A compound having the formula ##STR14## wherein L is a ketal, R 1 is selected from the group consisting of branched and straight chain alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted with a member selected from the group alkoxy and alkylthio of 1 to 4 carbon atoms and halogens, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 13 carbon atoms optionally substituted with a member selected from the group consisting of alkoxy and alkylthio of 1 to 4 carbon atoms and halogens, thienyl, isothienyl and furyl, R 2 is alkyl of 1 to 4 carbon atoms and R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkxoy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms and cyano, or one of R 3 and R 4 is a blocked hydroxy in the form of an easily removable ether and the other is cyano, or R 3 and R 4 form a ketone optionally protected as a cyclic ketal.
Claim 2
Dependent Claim
238 words
A compound having the formula ##STR14## wherein L is a ketal, R 1 is selected from the group consisting of branched and straight chain alkyl of 1 to 12 carbon atoms, unsaturated alkyl of 2 to 8 carbon atoms optionally substituted with a member selected from the group alkoxy and alkylthio of 1 to 4 carbon atoms and halogens, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 13 carbon atoms optionally substituted with a member selected from the group consisting of alkoxy and alkylthio of 1 to 4 carbon atoms and halogens, thienyl, isothienyl and furyl, R 2 is alkyl of 1 to 4 carbon atoms and R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkxoy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms and cyano, or one of R 3 and R 4 is a blocked hydroxy in the form of an easily removable ether and the other is cyano, or R 3 and R 4 form a ketone optionally protected as a cyclic ketal.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein L is ethyleneketal.
Claim 4
Dependent Claim
127 words
A compound of claim 1 having the formula ##STR15## wherein L is a ketal and R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms, and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms and cyano or one of R 3 and R 4 is a blocked hydroxy in the form of an easily removable ether and the other is cyano.
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is methyl.
Claim 6
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is ethyl.
Claim 7
Dependent Claim
15 words
A compound of claim 1 wherein R 3 is benzoyloxy and R 4 is hydrogen.
Claim 8
Dependent Claim
15 words
A compound of claim 1 wherein R 3 is cyano and R 4 is trimethylsilyloxy.
Claim 9
Dependent Claim
16 words
A compound of claim 1 wherein R 1 is alkyl of 1 to 12 carbon atoms.
Claim 10
Dependent Claim
35 words
A compound of claim 1 wherein R 1 is an unsaturated alkyl of 2 to 4 carbon atoms optionally substituted with alkoxy or alkylthio of 1 to 4 carbon atoms or at least one fluorine.
Claim 11
Dependent Claim
52 words
A compound of claim 1 wherein R 1 is selected from the group consisting of phenyl and benzyl optionally substituted on the phenyl with at least one member of the group consisting of halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and --CF 3 .
Claim 12
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is thienyl.
Claim 13
Dependent Claim
210 words
A process for the preparation of a compound of claim 1 comprising reacting a compound of the formula ##STR16## wherein L is a ketal and R 3 is selected from the group consisting of hydrogen, hydroxy, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms, alkoxy of 1 to 8 carbon atoms and acyl of an organic carboxylic acid of 1 to 18 carbon atoms and R 4 is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, acyloxy of an organic carboxylic acid of 1 to 18 carbon atoms and cyano, or one of R 3 and R 4 is a blocked hydroxy in the form of an easily removable ether and the other is cyano, or R 3 and R 4 form a ketone optionally protected as a cyclic ketal with a compound of a formula selected from the group consisting of (R 1 ) 2 CuLi, R 1 MgHal and R 1 Li wherein R 1 has the above definition and Hal is a halogen in the presence of a catalytic amount of a cuprous halide when R 1 Mg Hal and R 1 Li are used.
Claim 14
Dependent Claim
21 words
The process of claim 12 wherein R 3 and R 4 are other than a ketone optionally protected as a ketal.
References Cited (Backward Citations)
US2880233A
Cited
FR2237906A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-02 | 1982-10-02 | 1983-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-02 | 1986-10-02 | 1987-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-02 | 1990-10-02 | 1991-04-03 | $7700.00 | Window Closed / Lapsed |