US4916144A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-substituted imidazoles as aromatase inhibitors
Assignee: Bayer Pharma AG
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Filing: 1989-03-31
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Granted: 1990-04-10
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Expires: 2009-03-31
Abstract
Abstract The invention relates to N-substituted imidazoles of the formula, ##STR1## processes for their production as well as their use in pharmaceutical agents. The compounds according to the invention have aromatase-inhibiting properties and are suitable for therapy of estrogen-caused diseases.
Inventors
- 👤 Peter Strehlke
- 👤 Rolf Bohlmann
- 👤 David Henderson
- 👤 Yukishige Nishino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:48
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00; A61P35/00; A61P43/00; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
176 words
An imidazole of the formula ##STR8## in which R 1 is hydrogen, a hydrocarbyl radical with 1 to 10 carbon atoms, or a cyclic hydrocarbon radical with 3 to 9 carbon atoms, or a cycloalkylalkyl radical with 4 to 12 carbon atoms or an arylalkyl radical with 7 to 12 carbon atoms, R 2 is a benzyloxy group or benzyloxy substituted with halogen, C 1-4 -alkyl, hydroxyl, methoxy, amino, cyano or combinations thereof, R 3 is a cyano group; an alkanoyl group having 2 to 10 carbon atoms; an alkanoyl group having 2 to 10 carbon atoms which is substituted with halogen, methoxy, amino, hydroxyl, cyano and combinations thereof; a benzoyl group; a benzoyl group substituted with halogen, C 1-4 -alkyl, methoxy, amino, hydroxyl, cyano or combinations thereof; a carboxylic group; a carboxylic acid C 1-6 -alkyl ester; a carboxylic acid amide or the corresponding anilide thereof; a mono- or di-C 1-6 -alkylamide; or a saturated heterocyclic amide wherein the nitrogen atom thereof forms a ring of the formula ##STR9## or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
176 words
An imidazole of the formula ##STR8## in which R 1 is hydrogen, a hydrocarbyl radical with 1 to 10 carbon atoms, or a cyclic hydrocarbon radical with 3 to 9 carbon atoms, or a cycloalkylalkyl radical with 4 to 12 carbon atoms or an arylalkyl radical with 7 to 12 carbon atoms, R 2 is a benzyloxy group or benzyloxy substituted with halogen, C 1-4 -alkyl, hydroxyl, methoxy, amino, cyano or combinations thereof, R 3 is a cyano group; an alkanoyl group having 2 to 10 carbon atoms; an alkanoyl group having 2 to 10 carbon atoms which is substituted with halogen, methoxy, amino, hydroxyl, cyano and combinations thereof; a benzoyl group; a benzoyl group substituted with halogen, C 1-4 -alkyl, methoxy, amino, hydroxyl, cyano or combinations thereof; a carboxylic group; a carboxylic acid C 1-6 -alkyl ester; a carboxylic acid amide or the corresponding anilide thereof; a mono- or di-C 1-6 -alkylamide; or a saturated heterocyclic amide wherein the nitrogen atom thereof forms a ring of the formula ##STR9## or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
28 words
A compound according to claim 1: 4-(2,4-dichlorobenzyloxy)-3-[I-(1-imidazolyl)-butyl]-benzonitrile; {4-(4-bromobenzyloxy)-3-[1-(1-imidazolyl)-butyl]-phenyl}-pentylketone; 4-(4-bromobenzyloxy)-3-[1-(1-imidazolyl)-butyl]benzanilide; 4-(4-bromobenzyloxy)-3-[1-(1-imidazolyl)-butyl]-benzoic acid; 3-(2,4-dichlorobenzyloxy)-4-[1-(1-imidazolyl)-butylbenzonitrile; 3-(2,4-dichlorobenzyloxy)-4-[1-(1-imidazolyl)-butyl]benzoic acid methyl ester; 3-(2,4-dichlorobenzyloxy)-4-[1-(1-imidazolyl)-butyl]benzoic acid; 3-(3-bromobenzyloxy)-4-[1-(1-imidazolyl)-butyl]benzonitrile, hydrochloride; 4-(3-bromobenzyloxy)-3-[1-(1-imidazolyl)-butyl]benzonitrile; 3-(4-bromobenzyloxy)-4-[1-(1-imidazolyl)-butyl]-benzoic acid; 3-(4-bromobenzyloxy)-4-[1-(1-imidazolyl)-butyl]benzanilide; {3-(4-bromobenzyloxy)-4-[1-(1-imidazolyl)-butyl]-phenyl}-pentyl-ketone; 4-(4-bromobenzyloxy)-3-[1-(1-imidazolyl)-butyl]benzonitrile; or 3-(4-bromobenzyloxy)-4-[1-(1-imidazolyl)-butyl]-benzonitrile.
Claim 4
Dependent Claim
17 words
A compound of claim 1, wherein R 2 is 3-bromobenzyloxy, 4-bromobenzyloxy, 4-chlorobenzyloxy, 2,3-dichlorobenzyloxy, 2,4-dichlorobenzyloxy, 4,5-dichlorobenzyloxy or 4,6-dichlorobenzyloxy.
Claim 5
Dependent Claim
19 words
An aromatose-inhibiting pharmaceutical composition comprising an effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
19 words
An aromatose-inhibiting pharmaceutical composition comprising an effective amount of a compound of claim 2 and a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
25 words
A method of treating estrogen-stimulated tumors in a patient in need of such treatment comprising administering an effective amount of a compound of claim 1.
Claim 8
Dependent Claim
13 words
A method according to claim 6, wherein the effective amount if 0.0001-10 mg/kg/day.
Claim 9
Dependent Claim
19 words
A method of ameliorating male infertility in a host comprising an effective amount of a compound of claim 1.
Claim 10
Dependent Claim
13 words
A method according to claim 8, wherein the effective amount if 0.0001-10 mg/kg/day.
Claim 11
Dependent Claim
23 words
A method of inhibiting ovulation comprising administering to a female otherwise capable of ovulation an effective amount of a compound of claim 1.
Claim 12
Dependent Claim
13 words
A method according to claim 10, wherein the effective amount is 0.0001-10 mg/kg/day.
Claim 13
Dependent Claim
26 words
A method of treating imminent myocardial infarction in a patient in need of such treatment, comprising administering an effective amount of a compound of claim 1.
Claim 14
Dependent Claim
13 words
A method according to claim 12, wherein the effective amount is 0.0001-10 mg/kg/day.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-04-09 | 1993-10-09 | 1994-04-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-09 | 1997-10-09 | 1998-04-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-04-09 | 2001-10-09 | 2002-04-10 | $7700.00 | Window Closed / Lapsed |