US3978048A
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17β-SUBSTITUTED-ALLENE-BEARING STEROIDS
Assignee: Sandoz Inc
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Filing: 1975-02-25
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Granted: 1976-08-31
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Expires: 1995-02-25
Abstract
Abstract Steroidal compounds of the invention bear a 17 beta -oxygenated group and a 17 alpha - PSI -alkyl substituted allene group, e.g., 17 alpha -(penta-1'-2'-dienyl)-estra-4,9-dien-17 beta -ol-3-one, and are prepared by a procedure, e.g., involving reacting a corresponding intermediate bearing a 17 alpha -(3'-dialkylamino-3'-alkyl-substituted-1'-propynyl)-group with a complex hydride. The steroidal compounds are useful as pharmaceuticals, e.g., as progestational agents.
Inventors
- 👤 Imre Bacso
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 09:19
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0051; C07J1/0081; C07J1/0088; C07J1/0092; C07J43/00; C07J43/003
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
221 words
A compound of the formula ##SPC23## wherein R is alkyl having from 1 to 4 carbon atoms; R a is a hydrogen atom, or the residue of a hydrolyzable ether or ester; R 1 is a hydrogen atom or alkyl having from 1 to 6 carbon atoms, R 2 is a hydrogen atom or alkyl having from 1 to 8 carbon atoms, R 3 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms, phenyl, or phenyl having one or two substituents, independently, from the group of fluoro or alkyl having from 1 to 6 carbon atoms; or R 1 and R 3 may be joined so as to form a polymethylene bridge having from 3 to 12 carbon atoms; and St is a gonene residue selected from the group consisting of: ##SPC24## ##SPC25## wherein R 7 is oxo or ##EQU16## or ##EQU17## R 8 is a hydrogen atom, a hydrolyzable ether or ester residue; R 9 is a hydrogen atom or methyl; and R 10 is a hydrogen atom, 6α-methyl or 7α-methyl, provided that when any of R 2 and R 3 is a hydrogen atom or alkyl, R 1 is a hydrogen atom and the total number of carbon atoms in R 2 and R 3 does not exceed 4, then St is not of type (2).
Claim 2
Dependent Claim
221 words
A compound of the formula ##SPC23## wherein R is alkyl having from 1 to 4 carbon atoms; R a is a hydrogen atom, or the residue of a hydrolyzable ether or ester; R 1 is a hydrogen atom or alkyl having from 1 to 6 carbon atoms, R 2 is a hydrogen atom or alkyl having from 1 to 8 carbon atoms, R 3 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms, phenyl, or phenyl having one or two substituents, independently, from the group of fluoro or alkyl having from 1 to 6 carbon atoms; or R 1 and R 3 may be joined so as to form a polymethylene bridge having from 3 to 12 carbon atoms; and St is a gonene residue selected from the group consisting of: ##SPC24## ##SPC25## wherein R 7 is oxo or ##EQU16## or ##EQU17## R 8 is a hydrogen atom, a hydrolyzable ether or ester residue; R 9 is a hydrogen atom or methyl; and R 10 is a hydrogen atom, 6α-methyl or 7α-methyl, provided that when any of R 2 and R 3 is a hydrogen atom or alkyl, R 1 is a hydrogen atom and the total number of carbon atoms in R 2 and R 3 does not exceed 4, then St is not of type (2).
Claim 3
Dependent Claim
12 words
A compound of claim 1 wherein R a is a hydrogen atom.
Claim 4
Dependent Claim
11 words
A compound of claim 2 wherein St is of type (1).
Claim 5
Dependent Claim
8 words
The compound of claim 3 which is 17α-(penta-1',2'-dien-1'-yl)estra-4-en-17β-ol-3-one.
Claim 6
Dependent Claim
8 words
The compound of claim 3 which is 17α-(penta-1',2'-dien-1'-yl)-estra-4-en-3β,17β-diol
Claim 7
Dependent Claim
11 words
A compound of claim 2 wherein St is of type (2).
Claim 8
Dependent Claim
8 words
A compound of claim 6 which is 17α-(4'-phenylbuta-1',2'-dien-1'-yl)-estra-4,9-dien-17β-ol-3-one.
Claim 9
Dependent Claim
8 words
The compound of claim 6 which is 17α-(2-cyclopentylidenevinyl)-estra-4,9-dien-17β-ol-3-one.
Claim 10
Dependent Claim
8 words
The compound of claim 6 which is 17α-(2-cyclohexylidienevinyl)-estra-4,9-dien-17β-ol-3-one.
Claim 11
Dependent Claim
8 words
The compound of claim 6 which is 17α-(2-cyclododecylenevinyl)-estra-4,9-dien-17β-ol-3-one.
Claim 12
Dependent Claim
8 words
The compound of claim 6 which is 17α-(dodeca-1',2'-dien-1'-yl)-estra-4,9-dien-17β-ol-3-one.
Claim 13
Dependent Claim
8 words
The compound of claim 6 which is 17α-(1'-[3'-ethyl-penta-1',2'-dien-1'-yl)]-estra-4,9-dien-17β-ol-3-one.
Claim 14
Dependent Claim
11 words
A compound of claim 2 wherein St is of type (5).
Claim 15
Dependent Claim
8 words
The compound of claim 13 which is 17α-(buta-1',2'-dien-1'-yl)-9α-methylestra-4-en-17β-ol-3-one.
Claim 16
Dependent Claim
8 words
The compound of claim 13 which is 17α-[1'-(3'-methyl-buta-1',2'-dien-1'-yl)]-9α-methylestra-4-en-17β-ol-3-one.
Claim 17
Dependent Claim
8 words
The compound of claim 13 which is 9α-methyl-17α-(penta-1',2'-dien-1'-yl)-estra-4-en-17β-ol-3-one.
Claim 18
Dependent Claim
102 words
A compound of claim 1 wherein each of R 1 and R 2 is, independently, a hydrogen atom or alkyl having from 1 to 6 carbon atoms; R 3 is a hydrogen atom, alkyl having from 1 to 6 carbon atoms, phenyl, or phenyl having one or two fluoro or alkyl substituents having from 1 to 6 carbon atoms; or R 1 and R 3 may be joined so as to form a polymethylene bridge having from 3 to 5 carbon atoms; and St is a gonene residue selected from the group consisting of: ##SPC26## wherein R 7 is oxo or ##EQU18##
Claim 19
Dependent Claim
12 words
A compound of claim 17 wherein R a is a hydrogen atom.
Claim 20
Dependent Claim
17 words
A compound of claim 18 wherein R a is a hydrogen atom, St is of type (2).
Claim 21
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (1).
Claim 22
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (2).
Claim 23
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (3).
Claim 24
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (4).
Claim 25
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (5).
Claim 26
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (6).
Claim 27
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (7).
Claim 28
Dependent Claim
11 words
A compound of claim 1 wherein St is of type (8).
Claim 29
Dependent Claim
21 words
A compound of claim 21 wherein each of R 2 and R 3 , independently, is a hydrogen atom or alkyl.
Claim 30
Dependent Claim
22 words
A compound of claim 28 wherein the total number of carbon atoms of R 2 plus R 3 does not exceed 4.
Claim 31
Dependent Claim
17 words
A compound of claim 29 wherein R 3 is alkyl having from 1 to 3 carbon atoms.
Claim 32
Dependent Claim
12 words
A compound of claim 30 wherein R 2 is a hydrogen atom.
Claim 33
Dependent Claim
10 words
A compound of claim 30 wherein R 7 is oxo.
Claim 34
Dependent Claim
17 words
A compound of claim 32 wherein each of R 10 and R a is a hydrogen atom.
Claim 35
Dependent Claim
17 words
A compound of claim 28 wherein each of R 2 and R 3 is a hydrogen atom.
Claim 36
Dependent Claim
20 words
A compound of claim 1 wherein R 1 and R 3 are joined so as to form a polymethylene bridge.
Claim 37
Dependent Claim
13 words
A compound of claim 1 wherein R 3 is phenyl or substituted phenyl.
Claim 38
Dependent Claim
20 words
A compound of claim 20 wherein R 1 and R 3 are joined so as to form a polymethylene bridge.
Claim 39
Dependent Claim
13 words
A compound of claim 20 wherein R 3 is phenyl or substituted phenyl.
Claim 40
Dependent Claim
22 words
A compound of claim 20 wherein the total number of carbon atoms of R 2 plus R 3 does not exceed 4.
Claim 41
Dependent Claim
12 words
A compound of claim 39 wherein R 2 is a hydrogen atom.
Claim 42
Dependent Claim
14 words
A compound of claim 39 wherein R 3 is alkyl having 3 carbon atoms.
Claim 43
Dependent Claim
21 words
A compound of claim 20 wherein each of R 2 and R 3 , independently, is a hydrogen atom or alkyl.
Claim 44
Dependent Claim
196 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an amount of a compound of the formula: ##SPC27## wherein R is alkyl having from 1 to 4 carbon atoms; R a is a hydrogen atom, or the residue of a hydrolyzable ether or ester; R 1 is a hydrogen atom or alkyl having from 1 to 6 carbon atoms; R 2 is a hydrogen atom or alkyl having from 1 to 8 carbon atoms; R 3 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms, phenyl, or phenyl having one or two substituents selected, independently, from the group of fluoro or alkyl having from 1 to 6 carbon atoms; or R 1 and R 3 may be joined so as to form a polymethylene bridge having from 3 to 12 carbon atoms; and St is a gonene residue selected from the group consisting of: ##SPC28## wherein R 7 is oxo or ##EQU19## or ##EQU20## R 8 is a hydrogen atom, a hydrolyzable ether or ester residue; R 9 is a hydrogen atom or methyl; and R 10 is a hydrogen atom, 6α-methyl or 7α-methyl; effective in controlling fertility in a warm blodded animal.
Claim 45
Dependent Claim
196 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and an amount of a compound of the formula: ##SPC27## wherein R is alkyl having from 1 to 4 carbon atoms; R a is a hydrogen atom, or the residue of a hydrolyzable ether or ester; R 1 is a hydrogen atom or alkyl having from 1 to 6 carbon atoms; R 2 is a hydrogen atom or alkyl having from 1 to 8 carbon atoms; R 3 is a hydrogen atom, alkyl having from 1 to 8 carbon atoms, phenyl, or phenyl having one or two substituents selected, independently, from the group of fluoro or alkyl having from 1 to 6 carbon atoms; or R 1 and R 3 may be joined so as to form a polymethylene bridge having from 3 to 12 carbon atoms; and St is a gonene residue selected from the group consisting of: ##SPC28## wherein R 7 is oxo or ##EQU19## or ##EQU20## R 8 is a hydrogen atom, a hydrolyzable ether or ester residue; R 9 is a hydrogen atom or methyl; and R 10 is a hydrogen atom, 6α-methyl or 7α-methyl; effective in controlling fertility in a warm blodded animal.
Claim 46
Dependent Claim
56 words
The method of regulating fertility in a warm blooded animal by parenterally or orally administering to said animal, an amount effective for regulating fertility in said animal of a compund of the formula ##SPC29## in which R, R a , R 1 , R 2 , R 3 and St are as defined in claim 43.
References Cited (Backward Citations)
US3888849A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-31 | 1980-03-01 | 1980-08-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-31 | 1984-03-01 | 1984-08-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-31 | 1988-03-01 | 1988-08-31 | $7700.00 | Window Closed / Lapsed |