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US4536401A
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11β-aryl estradienes, processes for their production and pharmaceutical preparations containing them
Assignee: Bayer Pharma AG
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Filing: 1984-02-21
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Granted: 1985-08-20
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Expires: 2004-02-21
Abstract
Abstract Compounds of the formula I ##STR1## wherein R 1 is ##STR2## wherein R I and R II each independently is alkyl of 1-4 carbon atoms, or R I and R II together with the connecting N-atom form a 5- or 6-membered heterocyclic ring whose remaining atoms are all C-atoms, or which also includes and additional N-atom, an additional O or S atom or a combination thereof; ##STR3## wherein R I and R II are as defined above; --SR III , wherein R III is methyl, ethyl or phenyl; or --OR IV , wherein R IV is methyl, ethyl, propyl, methoxymethyl, allyl, or β-dimethylaminoethyl; R 2 is hydrogen, methyl, or ethyl; ##STR4## wherein the wavy lines mean that the substituent is in the α- or β-position, and ##STR5## M is Na, K or Li; and R V , R VI , R VII and R VIII each independently is alkyl of 1-4 carbon atoms, have valuable pharmacological properties, e.g., a combination of antiprogestational and antimineralocorticordal effects.
Inventors
- 👤 Guenter Neef
- 👤 Gerhard Sauer
- 👤 Rudolf Wiechert
- 👤 Helmut Hofmeister
- 👤 Ralph Rohde
- 👤 Klaus Annen
- 👤 Henry Laurent
- 👤 Sybille Beier
- 👤 Wolfgang Losert
- 👤 Walter Elger
- 👤 David Henderson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:36
CPC Classifications
C; C07; C07J; C07J41/00; C07J41/0033; C07J41/0077; C07J41/0083; C07J1/00; C07J1/0051; C07J1/0081; C07J21/00; C07J21/001; C07J21/003; C07J21/005; C07J21/006; C07J31/00; C07J31/006; C07J33/00; C07J33/005; C07J41/0088; C07J43/00; C07J43/003; C07J43/006; C07J63/00; C07J63/008; C07J71/00; C07J71/0005; C07J71/001
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
154 words
An 11β-aryl estradiene of Formula I ##STR28## wherein R 1 is ##STR29## wherein R I and R II each independently is alkyl of 1-4 carbon atoms, or R I and R II together with the connecting N-atom form a 5- or 6-membered hererocyclic ring whose remaining atoms are all C-atoms, or which also includes an additional N-atom, an additional O or S atom or a combination thereof; ##STR30## wherein R I and R II are as defined above; --SR III , wherein R III is methyl, ethyl or phenyl; or --OR IV , wherein R IV is methyl, ethyl, propyl, methoxymethyl, allyl, or β-dimethylaminoethyl; R 2 is hydrogen, methyl, or ethyl; ##STR31## wherein the wavy lines mean that the substituent is in the α- or β-position, and ##STR32## M is Na, K or Li; and R V , R VI , R VII and R VIII each independently is alkyl of 1-4 carbon atoms.
Claim 2
Dependent Claim
154 words
An 11β-aryl estradiene of Formula I ##STR28## wherein R 1 is ##STR29## wherein R I and R II each independently is alkyl of 1-4 carbon atoms, or R I and R II together with the connecting N-atom form a 5- or 6-membered hererocyclic ring whose remaining atoms are all C-atoms, or which also includes an additional N-atom, an additional O or S atom or a combination thereof; ##STR30## wherein R I and R II are as defined above; --SR III , wherein R III is methyl, ethyl or phenyl; or --OR IV , wherein R IV is methyl, ethyl, propyl, methoxymethyl, allyl, or β-dimethylaminoethyl; R 2 is hydrogen, methyl, or ethyl; ##STR31## wherein the wavy lines mean that the substituent is in the α- or β-position, and ##STR32## M is Na, K or Li; and R V , R VI , R VII and R VIII each independently is alkyl of 1-4 carbon atoms.
Claim 3
Dependent Claim
13 words
A lactone or potassium salt of 3-[11β-(4-dimethylaminophenyl)-17β-hydroxy-3-oxo-4,9(10)-estradien-17α-yl]propionic acid, a compound of claim 1.
Claim 4
Dependent Claim
6 words
11β-(4-Dimethylaminophenyl)-17β-hydroxy-17α-(3-hydroxypropyl)-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 5
Dependent Claim
13 words
A lactone or potassium salt of 3-[11β-[4-(2-dimethylaminoethoxy)phenyl]-17β-hydroxy-18-methyl-3-oxo-4,9(10)-estradien-17α-yl]propionic acid, a compound of claim 1.
Claim 6
Dependent Claim
6 words
11β-[4-(2-Dimethylaminoethoxy)phenyl]-17β-hydroxy-17α-(3-hydroxypropyl)-18-methyl-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 7
Dependent Claim
13 words
A lactone or sodium salt of 3-[17β-hydroxy-11β-(4-methoxyphenyl)-3oxo-4,9(10)-estradien-17.alpha.-yl]propionic acid, a compound of claim 1.
Claim 8
Dependent Claim
6 words
17β-Hydroxy-17α-(3-hydroxypropyl)-11β-(4-methoxyphenyl)-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 9
Dependent Claim
6 words
11β-(4-Dimethylaminophenyl)-17β-hydroxy-17α-(3-hydroxypropyl)-16β-methyl-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 10
Dependent Claim
8 words
11β-(4-Dimethylaminophenyl)-17β-hydroxy-17α-(3-hydroxypropyl)-18 -methyl-4,9(10)-estradien-3 one, a compound of claim 1.
Claim 11
Dependent Claim
6 words
11β-(4-Dimethylaminophenyl)-17aβ-hydroxy-17aα-(3-hydroxypropyl)-D-homo-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 12
Dependent Claim
6 words
11β-[4-(2,5-Dimethylpyrrol-l-yl)phenyl]-17β-hydroxy-17α-(3-hydroxypropyl)-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 13
Dependent Claim
6 words
17β-Hydroxy-17α-(3-hydroxypropyl)-11β-(4-piperidinophenyl)-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 14
Dependent Claim
6 words
17β-Hydroxy-17α-(3-hydroxypropyl)-11β-[4-(pyrrolidin-1-yl)phenyl]-4,9(10)-estradien-3-one, a compound of claim 1.
Claim 15
Dependent Claim
7 words
11β-(4-Dimethylaminophenyl)-3-oxo-4,9-estradiene [17(β-1')spiro-5'][1,2]oxathiolane-2'oxide, a compound of claim 1.
Claim 16
Dependent Claim
7 words
11β-(4-Methoxyphenyl)-3-oxo-4,9-estradiene [17(β-1')spiro-5'][1,2]oxathiolane-2'-oxide, a compound of claim 1.
Claim 17
Dependent Claim
6 words
11β-(4-Dimethylaminophenyl)-3'-methyl-4,9-estradien-[17(β-1')spiro-5']oxazolidine-2',3-dione, a compound of claim 1.
Claim 18
Dependent Claim
6 words
11β-(4-Methoxyphenyl)-3'-methyl-4,9-estradiene-[17(β-1')spiro-5']oxazolidine-2',3-dione, a compound of claim 1.
Claim 19
Dependent Claim
7 words
11β-(4-Methoxyphenyl)-3'-methyl-3-oxo-4,9-estradiene [17(β-1')spiro-5'][1,2,3]oxathiazolidine-2'-oxide, a compound of claim 1.
Claim 20
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is ##STR33##
Claim 21
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is dimethylamino.
Claim 22
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is alkoxy.
Claim 23
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is methoxy.
Claim 24
Dependent Claim
22 words
A pharmaceutical composition comprising an amount of a compound of claim 1 effective to cause an abortion and a pharmaceutically acceptable carrier.
Claim 25
Dependent Claim
17 words
A pharmaceutical composition comprising 10-1000 mg of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 26
Dependent Claim
22 words
A method inducing an abortion in a patient comprising administering to the patient an effective amount of a compound of claim 1.
Claim 27
Dependent Claim
23 words
A method of treating a patient suffering from aldosteronism comprising administering to the patient an effective amount of a compound of claim 1.
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) | 1988-08-19 | 1989-02-18 | 1989-08-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-19 | 1993-02-18 | 1993-08-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-19 | 1997-02-18 | 1997-08-20 | $7700.00 | Window Closed / Lapsed |