US4011314A
Expired / Lapsed
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7-hydroxyestradiols
Assignee: Bayer Pharma AG
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Filing: 1975-10-09
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Granted: 1977-03-08
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Expires: 1995-10-09
Abstract
Abstract 7-Hydroxyestradiols of the formula ##STR1## wherein R 1 is hydrogen, acyl, alkyl, cycloalkyl, an oxygenated saturated heterocyclic group or hydrocarbylsulfonyl; R 2 and R 3 each are hydrogen, acyl, oxygenated saturated heterocyclic group or R 2 is hydrocarbylsulfonyl and R 4 is alkyl, alkenyl, chlorinated alkenyl, alkynyl or chlorinated alkynyl, are useful for treating estrogen deficiency symptoms.
Inventors
- 👤 Karl Petzoldt
- 👤 Hans-Jorg Vidic
- 👤 Klaus Prezewowsky
- 👤 Yukishige Nishino
- 👤 Rudolf Wiechert
- 👤 Henry Laurent
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 18:21
CPC Classifications
C; C07; C07J; C07J31/00; C07J31/006; C07J1/00; C07J1/0051; C07J1/0059; C07J1/0081; C07J1/0088; C07J1/0096; C07J17/00; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/911; Y10S435/912; Y10S435/913; Y10S435/939
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
83 words
A hydroxyestradiol of the formula ##STR6## wherein R 1 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, alkyl of 1-8 carbon atoms, cycloalkyl of 3-7 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; R 2 and R 3 each are a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; and R 4 is alkenyl, chloroalkenyl, alkynyl or chloroalkynyl, each of up to 5 carbon atoms.
Claim 2
Dependent Claim
83 words
A hydroxyestradiol of the formula ##STR6## wherein R 1 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, alkyl of 1-8 carbon atoms, cycloalkyl of 3-7 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; R 2 and R 3 each are a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; and R 4 is alkenyl, chloroalkenyl, alkynyl or chloroalkynyl, each of up to 5 carbon atoms.
Claim 3
Dependent Claim
38 words
A compound of claim 1, wherein R 1 , R 2 and R 3 each are hydrogen or alkanoyl of 1-7 carbon atoms, the 7-oxygen atom is in the α-position and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 4
Dependent Claim
38 words
A compound of claim 1, wherein R 1 , R 2 and R 3 each are hydrogen or alkanoyl of 1-7 carbon atoms, the 7-oxygen atom is in the β-position and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 5
Dependent Claim
36 words
A compound of claim 1, wherein R 1 is cycloalkyl of 3-8 carbon atoms, R 2 and R 3 each are hydrogen or alkanoyl of 1-7 carbon atoms and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 6
Dependent Claim
35 words
A compound of claim 1, wherein R 1 and R 2 each are hydrogen, tetrahydropyranyl or tetrahydrofuryl, R 3 is hydrogen or alkanoyl of 1-7 carbon atoms and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 7
Dependent Claim
44 words
A compound of claim 1, wherein R 1 and R 2 each are hydrogen, alkanoyl of 1-7 carbon atoms or alkanesulfonyl of 1-4 carbon atoms; R 3 is hydrogen, alkanoyl of 1-7 carbons, tetrahydrofuryl or tetrahydropyranyl; and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 8
Dependent Claim
24 words
A compound of claim 1, wherein R 1 is hydrogen or alkyl of 1-5 carbon atoms and R 4 is vinyl, ethynyl or chloroethynyl.
Claim 9
Dependent Claim
6 words
17α-Ethynyl-1,3,5(10)-estratriene-3,7α,17β-triol, a compound of claim 1.
Claim 10
Dependent Claim
6 words
3-Acetoxy-17.alpha.-ethynyl-1,3,5(10)-estratriene-7α,17β-diol, a compound of claim 1.
Claim 11
Dependent Claim
6 words
3,7α,17β-Triacetoxy-17α-ethynyl-1,3,5(10)-estratriene, a compound of claim 1.
Claim 12
Dependent Claim
6 words
3,7α-Diacetoxy-17α-ethynyl-1,3,5(10)-estratriene-17β-ol, a compound of claim 1.
Claim 13
Dependent Claim
6 words
17α-Ethynyl-3-cyclopentoxy-1,3,5(10)-estratriene-7α,17β-diol, a compound of claim 1.
Claim 14
Dependent Claim
6 words
7α,17β-Diacetoxy-17α-ethynyl-3-cyclopentoxy-1,3,5(10)-estratriene, a compound of claim 1.
Claim 15
Dependent Claim
6 words
17α-Ethynyl-1,3,5(10)-estratriene-3,7β,17β-triol, a compound of claim 1.
Claim 16
Dependent Claim
6 words
3,7β,17β-Triacetoxy-17α-ethynyl-1,3,5(10)-estratriene, a compound of claim 1.
Claim 17
Dependent Claim
6 words
17α-Ethynyl-3-cyclopentoxy-1,3,5(10)-estratriene-7β,17β-diol, a compound of claim 1.
Claim 18
Dependent Claim
6 words
7.beta.,17β-Diacetoxy-17α-ethynyl-3-cyclopentoxy-1,3,5(10)-estratriene, a compound of claim 1.
Claim 19
Dependent Claim
6 words
3-Butyryloxy-17.alpha.-ethynyl-1,3,5(10)-estratriene-7α,17β-diol, a compound of claim 1.
Claim 20
Dependent Claim
6 words
3,7α-Dibutyryloxy-17α-ethynyl-1,3,5(10)-estratrien-17β-ol, a compound of claim 1.
Claim 21
Dependent Claim
6 words
3,7α-Bis-tetrahydropyranyloxy-17α-chloroethynyl-1,3,5(10)-estratrien-17β-ol, a compound of claim 1.
Claim 22
Dependent Claim
6 words
17α-Chloroethynyl-1,3,5(10)-estratriene-3,7α,17β-triol, a compound of claim 1.
Claim 23
Dependent Claim
6 words
17α-Ethynyl-3-acetoxy-7α-isopropylsulfonyloxy-1,3,5(10)-estratrien-17βol, a compound of claim 1.
Claim 24
Dependent Claim
6 words
17α-Ethynyl-3,7α-bis-isopropylsulfonyloxy-1,3,5(10)-estratrien-17βol, a compound of claim 1.
Claim 25
Dependent Claim
6 words
17α-Ethynyl-3,7α-bis-mexyloxy-17β-tetrahydropyranyloxy-1,3,5(10)-estratrien, a compound of claim 1.
Claim 26
Dependent Claim
6 words
17α-Ethynyl-3,7α-bis-mexyloxy-1,3,5(10)-estratrien-17β-ol, a compound of claim 1.
Claim 27
Dependent Claim
21 words
A pharmaceutical composition comprising an estrogenic amount per unit dosage of a compound of claim 1 in a pharmaceutically effective carrier.
Claim 28
Dependent Claim
6 words
3,7α,17β-Tris(heptanoyloxy)-17α-ethynyl-1,3,5(10)-estratriene, a compound of claim 1.
Claim 29
Independent Claim
117 words
A method of treating estrogen deficiency syndromes in a female mammal which comprises the enteral or parenteral administration of an amount effective to ameliorate symptoms of estrogen deficiency in the female mammal of a hydroxyestradiol of the formula. ##STR7## wherein R 1 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, alkyl of 1-8 carbon atoms, cycloalkyl of 3-7 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; R 2 and R 3 each are a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl and R 4 is alky, alkenyl, chloroalkenyl, alkynyl or chloroalkynyl, each of up to 5 carbon atoms.
Claim 30
Independent Claim
117 words
A method of treating estrogen deficiency syndromes in a female mammal which comprises the enteral or parenteral administration of an amount effective to ameliorate symptoms of estrogen deficiency in the female mammal of a hydroxyestradiol of the formula. ##STR7## wherein R 1 is a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, alkyl of 1-8 carbon atoms, cycloalkyl of 3-7 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl; R 2 and R 3 each are a hydrogen atom, the acyl radical of a hydrocarbon carboxylic or sulfonic acid of 1-15 carbon atoms, tetrahydrofuranyl or tetrahydropyranyl and R 4 is alky, alkenyl, chloroalkenyl, alkynyl or chloroalkynyl, each of up to 5 carbon atoms.
References Cited (Backward Citations)
US3115444A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-07 | 1980-09-06 | 1981-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-07 | 1984-09-06 | 1985-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-07 | 1988-09-06 | 1989-03-08 | $7700.00 | Window Closed / Lapsed |