US4016269A
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17α-HYDROXY-1,3,5(10),15-ESTRATETRAENES AND PROCESS FOR THEIR PRODUCTION
Assignee: Bayer Pharma AG
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Filing: 1975-08-11
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Granted: 1977-04-05
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Expires: 1995-08-11
Abstract
Abstract Novel estrogenic 17α-hydroxy-1,3,5(10),15-estratetraenes of the formula ##STR1## wherein R 1 is H, lower alkyl or lower acyl, R 2 is lower alkyl and R 3 is H, lower alkyl, lower acyl or tetrahydropyranyloxy, are produced by (a) reacting a 16α,17α-epoxy-estratriene with lithium halide or HCl in glacial acetic acid; converting the resulting halohydrin into a 16-halo-17-tetrahydropyranyl ether; and splitting off hydrogen halide from therefrom; or (b) reacting the 16α,17α-epoxy-estratriene with diphenylselenide and alkali metal borohydride; oxidizing the thus-produced 17α-hydroxy-16β-phenylselenide to the corresponding phenylselenide oxide; and forming the Δ 15 double bond by heating with removal of phenyl--Se--OH.
Inventors
- 👤 Helmut Hofmeister
- 👤 Klaus Annen
- 👤 Rudolf Wiechert
- 👤 Henry Laurent
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:55
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0051; C07J1/0062; C07J17/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
50 words
A 17α-oxy-1,3,5(10),15-estratetraene of the formula ##STR7## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms; R 2 is ethyl and R 3 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms or tetrahydropyranyl or tetrahydrofuryl.
Claim 2
Dependent Claim
50 words
A 17α-oxy-1,3,5(10),15-estratetraene of the formula ##STR7## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms; R 2 is ethyl and R 3 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms or tetrahydropyranyl or tetrahydrofuryl.
Claim 3
Dependent Claim
9 words
A compound of claim 1, wherein alkanoyl is acetyl.
Claim 4
Dependent Claim
20 words
A compound of claim 1, wherein R 1 is H, methyl or acetyl and R 3 is H or acetyl.
Claim 5
Dependent Claim
6 words
A compound of claim 1, 3-methoxy-18-methoxy-18-methyl-17α-tetrahydropyranyloxy-1,3,5(10),15-estratetraene.
Claim 6
Dependent Claim
6 words
A compound of claim 1, 3-methoxy-18-methyl-1,3,5(10),15-estratetraene-17α-ol.
Claim 7
Dependent Claim
6 words
A compound of claim 1, 17α-acetoxy-3-methoxy-18-methyl-1,3,5(10),15-estratetraene.
Claim 8
Dependent Claim
6 words
A compound of claim 1, 3-methoxy-17α-tetrahydropyranyloxy-1,3,5(10),15-estratetraene.
Claim 9
Dependent Claim
26 words
A pharmaceutical composition comprising an estrogenically effective amount of a compound of claim 1, in unit dosage form and in admixture with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
70 words
A process for the production of 17α-hydroxy-1,3,5(10),15-estratetraenes of claim 1, which comprises the steps of heating, in the presence of an alkaline reagent reactive with hydrogen halide, a 16β-halo-17α-tetrahydropyranyloxy estratriene of the formula ##STR8## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms, halogen is chlorine or bromine and THP is tetrahydropyranyl.
Claim 11
Dependent Claim
43 words
A process according to claim 9, wherein the starting estratetraene is produced by reacting the corresponding 16α,17α-epoxide with lithium halide or HCl in glacial acetic acid and converting the halohydrin into the 17-tetrahydropyranyl ether by reaction with dihydropyran in the presence of acid.
Claim 12
Dependent Claim
12 words
A process for the production of 17α-hydroxy-1,3,5(10),15-estratetraenes of claim 1, which comprises
Claim 13
Dependent Claim
64 words
a. reacting a 16α,17α-epoxy-estratriene of the formula ##STR9## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms, with diphenyldiselenide to the corresponding selenium oxide of the formula ##STR10## and introducing the Δ 15 -double bond by heating the thus-produced selenium oxide while splitting off Ph-Se-OH; or
Claim 14
Dependent Claim
64 words
a. reacting a 16α,17α-epoxy-estratriene of the formula ##STR9## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms, with diphenyldiselenide to the corresponding selenium oxide of the formula ##STR10## and introducing the Δ 15 -double bond by heating the thus-produced selenium oxide while splitting off Ph-Se-OH; or
Claim 15
Dependent Claim
13 words
b. reacting the starting 16α,17α-epoxy-estratriene with the lithium salt of a strong base.
Claim 16
Dependent Claim
13 words
b. reacting the starting 16α,17α-epoxy-estratriene with the lithium salt of a strong base.
Claim 17
Dependent Claim
34 words
A 16β-halo-17α-tetrahydropyranyloxy estratriene of the formula ##STR11## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms.
Claim 18
Dependent Claim
34 words
A 16β-halo-17α-tetrahydropyranyloxy estratriene of the formula ##STR11## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms.
Claim 19
Dependent Claim
24 words
A 16α,17α-epoxy-estratriene of the formula ##STR12## wherein R 1 is a hydrogen atom or alkanoyl of 1-5 carbon atoms and R 2 is ethyl.
Claim 20
Dependent Claim
24 words
A 16α,17α-epoxy-estratriene of the formula ##STR12## wherein R 1 is a hydrogen atom or alkanoyl of 1-5 carbon atoms and R 2 is ethyl.
Claim 21
Dependent Claim
33 words
A compound of the formula ##STR13## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms.
Claim 22
Dependent Claim
33 words
A compound of the formula ##STR13## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and R 2 is alkyl of 1-5 carbon atoms.
Claim 23
Dependent Claim
28 words
A 17α-tetrahydropyranyloxy-1,3,5(10),15-estratetraene of the formula ##STR14## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and THP is tetrahydropyranyl.
Claim 24
Dependent Claim
28 words
A 17α-tetrahydropyranyloxy-1,3,5(10),15-estratetraene of the formula ##STR14## wherein R 1 is a hydrogen atom, alkyl of 1-5 carbon atoms or alkanoyl of 1-5 carbon atoms and THP is tetrahydropyranyl.
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) | 1980-04-04 | 1980-10-04 | 1981-04-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-04 | 1984-10-04 | 1985-04-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-04 | 1988-10-04 | 1989-04-05 | $7700.00 | Window Closed / Lapsed |