US3966713A
Expired / Lapsed
US
⏱️ 0.0 years remaining
11β-FLUOROANDROSTENES
Assignee: Bayer Pharma AG
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Filing: 1975-02-25
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Granted: 1976-06-29
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Expires: 1995-02-25
Abstract
Abstract 11β-Fluoroandrostenes of the formula ##SPC1## Wherein R 1 and R 2 are hydrogen atoms, methylene or another C--C bond; R 3 is H or Cl, R 4 is H, F or Cl; and X is carbonyl, β-hydroxymethylene, or an ester or ether thereof or α-alkyl-β-hydroxymethylene or an ester thereof, possess androgenic activity and can be prepared by the dehalogenation of a corresponding 9α-halo-11β-F steroid.
Inventors
- 👤 Helmut Hofmeister
- 👤 Henry Laurent
- 👤 Rudolf Wiechert
- 👤 Klaus Annen
- 👤 Hermann Steinbeck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 19:55
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0003; C07J1/0018; C07J1/0022; C07J1/0029; C07J1/0011; C07J1/0025; C07J1/0033; C07J1/0037; C07J1/004; C07J1/0048; C07J53/00; C07J53/002; C07J53/004; C07J53/005; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
135 words
A 11β-fluoroandrostene of the formula ##SPC4## wherein R 1 and R 2 each are a hydrogen atom or collectively are methylene or a further carbon-to-carbon bond between the C-1 and C-2 carbon atoms; R 3 is a hydrogen atom or a chlorine atom, R 4 is a hydrogen atom, a fluorine atom or a chlorine atom, C C is a single or double bond between the C-6 and C-7 carbon atoms, and X is ##EQU2## wherein R 5 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic acid of 1-18 carbon atoms, alkyl of 1-4 carbon atoms, or tetrahydropyranyl; R 6 is a hydrogen atom or the acyl radical of a hydrocarbon carboxylic acid of 1-18 carbon atoms, and R 7 is alkyl, alkenyl or alkynyl of 1-5 carbon atoms, butadiynyl or chloroethynyl.
Claim 2
Dependent Claim
135 words
A 11β-fluoroandrostene of the formula ##SPC4## wherein R 1 and R 2 each are a hydrogen atom or collectively are methylene or a further carbon-to-carbon bond between the C-1 and C-2 carbon atoms; R 3 is a hydrogen atom or a chlorine atom, R 4 is a hydrogen atom, a fluorine atom or a chlorine atom, C C is a single or double bond between the C-6 and C-7 carbon atoms, and X is ##EQU2## wherein R 5 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic acid of 1-18 carbon atoms, alkyl of 1-4 carbon atoms, or tetrahydropyranyl; R 6 is a hydrogen atom or the acyl radical of a hydrocarbon carboxylic acid of 1-18 carbon atoms, and R 7 is alkyl, alkenyl or alkynyl of 1-5 carbon atoms, butadiynyl or chloroethynyl.
Claim 3
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-4-androsten-3-one, a compound of claim 1.
Claim 4
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-1,4-androstadien-3-one, a compound of claim 1.
Claim 5
Dependent Claim
6 words
11β-Fluoro-17β-hydroxy-4-androsten-3-one, a compound of claim 1.
Claim 6
Dependent Claim
6 words
11β-Fluoro-17β-heptanoyloxy-4-androsten-3-one, a compound of claim 1.
Claim 7
Dependent Claim
6 words
11β-Fluoro-17β-(3'-cyclopentylpropionyloxy)-4-androsten-3-one, a compound of claim 1.
Claim 8
Dependent Claim
6 words
11β-Fluoro-17β-decanoyloxy-4-androsten-3-one, a compound of claim 1.
Claim 9
Dependent Claim
6 words
17β-Benzoyloxy-11β-fluoro-4-androsten-3-one, a compound of claim 1.
Claim 10
Dependent Claim
6 words
11β-Fluoro-17β-methoxy-4-androsten-3-one, a compound of claim 1.
Claim 11
Dependent Claim
6 words
11β-Fluoro-17β-butoxy-4-androsten-3-one, a compound of claim 1.
Claim 12
Dependent Claim
6 words
11β-Fluoro-17β-tetrahydropyranyloxy-4-androsten-3-one, a compound of claim 1.
Claim 13
Dependent Claim
6 words
11β-Fluoro-4-androstene-3,17-dione, a compound of claim 1.
Claim 14
Dependent Claim
6 words
17α-Ethinyl-11β-fluoro-17β-hydroxy-4-androsten-3-one, a compound of claim 1.
Claim 15
Dependent Claim
6 words
17β-Acetoxy-17α-ethinyl-11β-fluoro-4-androsten-3-one, a compound of claim 1.
Claim 16
Dependent Claim
6 words
17α-Ethinyl-11β-fluoro-17β-heptanoyloxy-4-androsten-3-one, a compound of claim 1.
Claim 17
Dependent Claim
6 words
17.alpha.-Ethinyl-11β-fluoro-17β-hexadecanoyloxy-4-androsten-3-one, a compound of claim 1.
Claim 18
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-4,6-androstadien-3-one, a compound of claim 1.
Claim 19
Dependent Claim
6 words
17β-Acetoxy-6-chloro-11β-fluoro-4,6-androstadien-3-one, a compound of claim 1.
Claim 20
Dependent Claim
6 words
11β-Fluoro-4,6-androstadiene-3,17-dione, a compound of claim 1.
Claim 21
Dependent Claim
6 words
17α-Ethinyl-11β-fluoro-17β-hydroxy-4,6-androstadien-3-one, a compound of claim 1.
Claim 22
Dependent Claim
6 words
17α-Ethinyl-6-chloro-11β-fluoro-17β-hydroxy-4,6-androstadien-3-one, a compound of claim 1.
Claim 23
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-1,4,6-androstatrien-3-one, a compound of claim 1.
Claim 24
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-1α,2α-methylene-4,6-androstadien-3-one, a compound of claim 1.
Claim 25
Dependent Claim
6 words
17β-Acetoxy-4-chloro-11β-fluoro-4-androsten-3-one, a compound of claim 1.
Claim 26
Dependent Claim
6 words
11β-Fluoro-17β-hydroxy-17α-methyl-4-androsten-3-one, a compound of claim 1.
Claim 27
Dependent Claim
6 words
17β-Acetoxy-6,11β-difluoro-4,6-androstadien-3-one, a compound of claim 1.
Claim 28
Dependent Claim
6 words
17β-Acetoxy-6β-chloro-11β-fluoro-4-androsten-3-one, a compound of claim 1.
Claim 29
Dependent Claim
7 words
17β-Acetoxy-6α-chloro-11β-fluoro-4-androsten-3 -one, a compound of claim 1.
Claim 30
Dependent Claim
6 words
17β-Acetoxy-4,6-dichloro-11β-fluoro-4,6-androstadien-3-one, a compound of claim 1.
Claim 31
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-4,6-androstadien-3-one, a compound of claim 1.
Claim 32
Dependent Claim
6 words
11β-Fluoro-17β-propionyloxy-4-androsten-3-one, a compound of claim 1.
Claim 33
Dependent Claim
6 words
17β-Acetoxy-11β-fluoro-1,4,6-androstatrien-3-one, a compound of claim 1.
Claim 34
Dependent Claim
145 words
A process for the production of a compound of formula ##SPC5## wherein R 1 and R 2 each are a hydrogen atom or collectively are methylene or a further carbon-to-carbon bond between the C-1 and C-2 carbon atoms; R 3 is a hydrogen atom or a chlorine atom, R 4 is a hydrogen atom, a fluorine atom or a chlorine atom, C C is a single or double bond between the C-6 and C-7 carbon atoms, and X is carbonyl, β-hydroxy-methylene or an ester or ether thereof or α-alkyl-β-hydroxy-methylene or an ester thereof, which comprises dehalogenating a corresponding 9α-bromo- or 9α-chloro-11β-fluoro steroid of the formula ##SPC6## wherein C C, R 1 , R 2 , R 3 , R 4 and X have the values given above and Z is Cl or Br, with a tin hydride in an inert solvent at about room temperature.
Claim 35
Dependent Claim
145 words
A process for the production of a compound of formula ##SPC5## wherein R 1 and R 2 each are a hydrogen atom or collectively are methylene or a further carbon-to-carbon bond between the C-1 and C-2 carbon atoms; R 3 is a hydrogen atom or a chlorine atom, R 4 is a hydrogen atom, a fluorine atom or a chlorine atom, C C is a single or double bond between the C-6 and C-7 carbon atoms, and X is carbonyl, β-hydroxy-methylene or an ester or ether thereof or α-alkyl-β-hydroxy-methylene or an ester thereof, which comprises dehalogenating a corresponding 9α-bromo- or 9α-chloro-11β-fluoro steroid of the formula ##SPC6## wherein C C, R 1 , R 2 , R 3 , R 4 and X have the values given above and Z is Cl or Br, with a tin hydride in an inert solvent at about room temperature.
Claim 36
Dependent Claim
19 words
A process according to claim 33, wherein the 9α-halogen atom is dehalogenated with a trialkyltin hydride or triaryltin hydride.
Claim 37
Dependent Claim
14 words
A process according to claim 34, wherein the tin hydride is a triaryltin hydride.
Claim 38
Dependent Claim
13 words
A process according to claim 35, wherein the tin hydride is triphenyltin hydride.
Claim 39
Dependent Claim
25 words
A method of increasing the androgen blood levels in a patient which comprises administering thereto an androgenically effective amount of a compound of claim 1.
Claim 40
Dependent Claim
26 words
A pharmaceutical composition comprising an androgenically effective amount per unit dosage of one or more compounds of claim 1 in admixture with a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-29 | 1979-12-29 | 1980-06-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-29 | 1983-12-29 | 1984-06-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-29 | 1987-12-29 | 1988-06-29 | $7700.00 | Window Closed / Lapsed |