Patent US1815762A successfully refreshed from Google Patents.
Patent US4134983A successfully refreshed from Google Patents.
US4134983A
Expired / Lapsed
US
⏱️ 0.0 years remaining
3-amino-2-or-propoxyaryl substituted imidazoles
Assignee: Merck and Co Inc
•
Filing: 1975-12-17
•
Granted: 1979-01-16
•
Expires: 1995-12-17
Abstract
Abstract Novel 3-amino-2-OR-propoxyaryl substituted imidazoles and methods for their preparation are disclosed. These imidazoles, and their salts, exhibit pharmacological activity which includes antihypertensive activity and β-adrenergic blocking activity.
Inventors
- 👤 John J. Baldwin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 02:53
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07C; C07C45/00; C07C45/008; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/46; C07D213/48; C07D213/51; C07D213/60; C07D213/78; C07D213/84; C07D213/85; C07D233/66; C07D233/90; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
211 words
Compound having the formula ##STR101## wherein R and R 1 are independently selected from hydrogen, C 1 -C 10 linear or branched alkyl and substituted C 1 -C 10 linear or branched alkyl having 1-3 substituents selected fromhalo, hydroxy or C 1 -C 4 alkoxy. R 2 is hydrogen, C 1 -C 10 linear or branched alkyl, or C 3 -C 6 alkenyl, R 3 is selected from naphthyl and phenyl having the formula ##STR102## R c is selected from halogen, lower-C 1 -C 4 linear or branched alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, hydroxy, cyano and phenyl, and x is 0, 1, 2, 3, or 4, R 4 is hydroxy or ##STR103## wherein R b is C 1 -C 6 linear or branched alkyl, and R 5 and R 6 , when separate, are independently selected from hydrogen, C 3 -C 6 cycloalkyl, C 1 -C 6 linear or branched alkyl and monosubstituted C 1 -C 6 linear or branched alkyl wherein the substituent; is phenyl provided that when one of R 5 and R 6 is said substituted alkyl group, the other is hydrogen and when joined together with the N atom form ##STR104## and pharmacologically acceptable acid addition and quaternary ammonium salts thereof.
Claim 2
Dependent Claim
211 words
Compound having the formula ##STR101## wherein R and R 1 are independently selected from hydrogen, C 1 -C 10 linear or branched alkyl and substituted C 1 -C 10 linear or branched alkyl having 1-3 substituents selected fromhalo, hydroxy or C 1 -C 4 alkoxy. R 2 is hydrogen, C 1 -C 10 linear or branched alkyl, or C 3 -C 6 alkenyl, R 3 is selected from naphthyl and phenyl having the formula ##STR102## R c is selected from halogen, lower-C 1 -C 4 linear or branched alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, hydroxy, cyano and phenyl, and x is 0, 1, 2, 3, or 4, R 4 is hydroxy or ##STR103## wherein R b is C 1 -C 6 linear or branched alkyl, and R 5 and R 6 , when separate, are independently selected from hydrogen, C 3 -C 6 cycloalkyl, C 1 -C 6 linear or branched alkyl and monosubstituted C 1 -C 6 linear or branched alkyl wherein the substituent; is phenyl provided that when one of R 5 and R 6 is said substituted alkyl group, the other is hydrogen and when joined together with the N atom form ##STR104## and pharmacologically acceptable acid addition and quaternary ammonium salts thereof.
Claim 3
Dependent Claim
8 words
Compounds of claim 1 wherein R is hydrogen.
Claim 4
Dependent Claim
9 words
Compounds of claim 2 wherein R 2 is hydrogen.
Claim 5
Dependent Claim
9 words
Compounds of claim 3 wherein R 4 is hydroxy.
Claim 6
Dependent Claim
9 words
Compounds of claim 4 wherein R 4 is hydrogen.
Claim 7
Dependent Claim
8 words
Compounds of claim 1 wherein R is hydrogen.
Claim 8
Dependent Claim
9 words
Compounds of claim 1 wherein R 2 is hydrogen.
Claim 9
Dependent Claim
11 words
Compounds of claim 1 wherein R 3 is said phenyl group.
Claim 10
Dependent Claim
9 words
Compounds of claim 1 wherein R 3 is ##STR105##
Claim 11
Dependent Claim
14 words
Compounds of claim 9 wherein R c is independently selected from chloro and methyl.
Claim 12
Dependent Claim
8 words
Compounds of claim 10 wherein x is 2.
Claim 13
Dependent Claim
8 words
Compounds of claim 10 wherein x is 1.
Claim 14
Dependent Claim
8 words
Compounds of claim 10 wherein x is 0.
Claim 15
Dependent Claim
8 words
Compounds of claim 13 wherein R is hydrogen.
Claim 16
Dependent Claim
9 words
Compounds of claim 14 wherein R 2 is hydrogen.
Claim 17
Dependent Claim
9 words
Compounds of claim 15 wherein R 4 is hydroxy.
Claim 18
Dependent Claim
9 words
Compounds of claim 16 wherein R 5 is hydrogen.
Claim 19
Dependent Claim
20 words
Compounds of claim 17 wherein R 1 is selected from hydrogen, said haloalkyl, and lower C 1 -C 6 alkyl.
Claim 20
Dependent Claim
21 words
Compounds of claim 18 wherein R 1 is selected from trifluoromethyl, and lower C 1 -C 6 linear or branched alkyl.
Claim 21
Dependent Claim
24 words
Compounds of claim 19 wherein R 6 is said C 1 -C 6 linear or branched alkyl or said C 3 -C 6 cycloalkyl.
Claim 22
Dependent Claim
16 words
Compounds of claim 20 wherein R 6 is C 3 -C 4 branched or cyclic alkyl.
Claim 23
Dependent Claim
9 words
Compounds of claim 21 wherein R 6 is isopropyl.
Claim 24
Dependent Claim
9 words
Compounds of claim 21 wherein R 6 is tert-butyl.
Claim 25
Dependent Claim
9 words
Compounds of claim 21 wherein R 6 is cyclopropyl.
Claim 26
Dependent Claim
9 words
Compounds of claim 21 wherein R 1 is trifluoromethyl.
Claim 27
Dependent Claim
21 words
Compounds of claim 1 wherein R is H, R 2 is H, R 5 is H and R 4 is hydroxy.
Claim 28
Dependent Claim
11 words
Compounds of claim 26 wherein R 1 is --CF 3 .
Claim 29
Dependent Claim
35 words
Compounds of claim 9 wherein x is 2 and R 5 and R 6 are independently selected from H, said C 1 -C 6 linear or branched alkyl and said C 3 -C 6 cycloalkyl.
Claim 30
Dependent Claim
8 words
Compounds of claim 28 wherein x is 1.
Claim 31
Dependent Claim
8 words
Compounds of claim 29 wherein x is 0.
Claim 32
Dependent Claim
25 words
Pharmaceutical composition for use as antihypertensive or β-adrenergic blocking agent comprising an effective amount of a compound of claim 1 and pharmacologically acceptable compounding agents.
Claim 33
Dependent Claim
17 words
Method of treating animals having hypertension which comprises administering an antihypertensive amount of compound of claim 1.
Claim 34
Dependent Claim
128 words
Pharmaceutical composition for use an antihypertensive or β-adrenergic blocking agent comprising an effective amount of compound having the formula ##STR106## wherein R 1 is selected from hydrogen and --CF 3 , R 3 is selected from naphthyl and phenyl having the formula wherein R c is selected from halogen, lower --C 1 -C 4 linear or branched alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, hydroxy, cyano and phenyl and x is 0, 1, 2, 3 or 4 and R 6 is selected from hydrogen, C 3 -C 6 cycloalkyl, C 1 -C 6 linear or branched alkyl and monosubstituted C 1 -C 6 linear or branched alkyl wherein the substituent is phenyl or pharmacologically acceptable salts thereof in combination with pharmacologically acceptable compounding agents.
Claim 35
Dependent Claim
128 words
Pharmaceutical composition for use an antihypertensive or β-adrenergic blocking agent comprising an effective amount of compound having the formula ##STR106## wherein R 1 is selected from hydrogen and --CF 3 , R 3 is selected from naphthyl and phenyl having the formula wherein R c is selected from halogen, lower --C 1 -C 4 linear or branched alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, hydroxy, cyano and phenyl and x is 0, 1, 2, 3 or 4 and R 6 is selected from hydrogen, C 3 -C 6 cycloalkyl, C 1 -C 6 linear or branched alkyl and monosubstituted C 1 -C 6 linear or branched alkyl wherein the substituent is phenyl or pharmacologically acceptable salts thereof in combination with pharmacologically acceptable compounding agents.
Claim 36
Dependent Claim
6 words
2-[4(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
Claim 37
Dependent Claim
6 words
2-[4(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
Claim 38
Dependent Claim
6 words
(S)-2-[4-(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
Claim 39
Dependent Claim
6 words
(S)-2-[4-(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
Claim 40
Dependent Claim
6 words
(S)-2-[4-(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-methylimidazole and pharmacologically acceptable salts thereof.
Claim 41
Dependent Claim
6 words
(S)-2-[4-(3-tert-butylamino-2-hydroxypropoxy)-phenyl]-4-methylimidazole and pharmacologically acceptable salts thereof.
Claim 42
Dependent Claim
6 words
2-[4-(3-Cyclopropylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
Claim 43
Dependent Claim
6 words
2-[4-(3-Cyclopropylamino-2-hydroxypropoxy)-phenyl]-4-trifluoromethylimidazole and pharmacologically acceptable salts thereof.
References Cited (Backward Citations)
US3786061A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-15 | 1982-07-17 | 1983-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-15 | 1986-07-17 | 1987-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-15 | 1990-07-17 | 1991-01-16 | $7700.00 | Window Closed / Lapsed |