Patent US4461904A successfully refreshed from Google Patents.
US4461904A
Expired / Lapsed
US
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2-(Trisubstituted phenylimino)-imidazolines
Assignee: Alcon Research LLC
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Filing: 1981-11-20
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Granted: 1984-07-24
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Expires: 2001-11-20
Abstract
Abstract 2-Trisubstituted Phenylimino-imidazolines also known as 2-(trisubstituted anilino)-1,3 diazacyclopentene-(2) compounds and their use for lowering intraocular pressure are disclosed.
Inventors
- 👤 Billie M. York, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 14:27
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/44; C07D233/50; A; A61; A61P; A61P27/00; A61P27/02; A61P27/06
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
270 words
A 2-(trisubstituted phenylimino)-imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR10## wherein I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, R 3 is selected from ##STR11## R 5' or R 5 =H or lower alkyl, R 6' or R 6 =H or lower alkyl, but if R 6' =methyl then R 1 and R 2 are not both chloro, the sum of the carbon atoms in R 5 and R 6 or R 5' and R 6' being 4 or less, and R 4 =H; or II. R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR12## R 5 =H or lower alkyl, R 6 =H or lower alkyl, the sum of the carbon atoms in R 5 and R 6 being 4 or less; or III. R 1 =R 2 =trifluoromethyl, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo and at least one of R 1 or R 2 =trifluoromethyl, ##STR13## R 5 =H or lower alkyl, R 7 =H, lower alkyl, 2-hydroxyethyl, 2-hydroxlpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, and R 4 =H; or IV. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro, or bromo, ##STR14## R 5 =H or lower alkyl R 7 =2-hydroxyethyl, 2-hydroxylpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, but if R 3 =H then R 1 =R 2 =ethyl.
Claim 2
Dependent Claim
270 words
A 2-(trisubstituted phenylimino)-imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR10## wherein I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, R 3 is selected from ##STR11## R 5' or R 5 =H or lower alkyl, R 6' or R 6 =H or lower alkyl, but if R 6' =methyl then R 1 and R 2 are not both chloro, the sum of the carbon atoms in R 5 and R 6 or R 5' and R 6' being 4 or less, and R 4 =H; or II. R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR12## R 5 =H or lower alkyl, R 6 =H or lower alkyl, the sum of the carbon atoms in R 5 and R 6 being 4 or less; or III. R 1 =R 2 =trifluoromethyl, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo and at least one of R 1 or R 2 =trifluoromethyl, ##STR13## R 5 =H or lower alkyl, R 7 =H, lower alkyl, 2-hydroxyethyl, 2-hydroxlpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, and R 4 =H; or IV. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro, or bromo, ##STR14## R 5 =H or lower alkyl R 7 =2-hydroxyethyl, 2-hydroxylpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, but if R 3 =H then R 1 =R 2 =ethyl.
Claim 3
Dependent Claim
145 words
A 2-(trisubstituted phenylimino) imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR15## wherein I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, R 3 is selected from ##STR16## R 5' or R 5 =H or lower alkyl, R 6' or R 6 =H or lower alkyl, but if R 6' =methyl then R 1 and R 2 are not both chloro, the sum of the carbon atoms in R 5 and R 6 or R 5' and R 6' being 4 or less, and R 4 =H; or II. R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR17## R 5 =H or lower alkyl, R 6 =H or lower alkyl, the sum of the carbon atoms in R 5 and R 6 being 4 or less.
Claim 4
Dependent Claim
145 words
A 2-(trisubstituted phenylimino) imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR15## wherein I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, R 3 is selected from ##STR16## R 5' or R 5 =H or lower alkyl, R 6' or R 6 =H or lower alkyl, but if R 6' =methyl then R 1 and R 2 are not both chloro, the sum of the carbon atoms in R 5 and R 6 or R 5' and R 6' being 4 or less, and R 4 =H; or II. R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR17## R 5 =H or lower alkyl, R 6 =H or lower alkyl, the sum of the carbon atoms in R 5 and R 6 being 4 or less.
Claim 5
Dependent Claim
12 words
A 2-(trisubstituted phenylimino)-imidazoline in accordance with claim 2 having the formula ##STR18##
Claim 6
Dependent Claim
12 words
A 2-(trisubstituted phenylimino)-imidazoline in accordance with claim 2 having the formula ##STR19##
Claim 7
Dependent Claim
31 words
A 2-(trisubstituted phenylimino) imidazoline compound as recited in claim 2 wherein in I if R 6' =lower alkyl, R 1 and R 2 are each selected from methyl, ethyl or trifluoromethyl.
Claim 8
Dependent Claim
97 words
A 2-(trisubstituted phenylimino)-imidazoline compound as recited in claim 2 wherein I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, R 3 is selected from ##STR20## R 5' or R 5 =H or lower alkyl, R 6' or R 6 =H or lower alkyl, but if R 6' =methyl then R 1 and R 2 are not both chloro, the sum of the carbon atoms in R 5 and R 6 or R 5' and R 6' being 4 or less, and R 4 =H.
Claim 9
Dependent Claim
50 words
A 2-(trisubstituted phenylimino)-imidazoline compound as recited in claim 2 wherein R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR21## R 5 =H or lower alkyl, R 6 =H or lower alkyl, the sum of the carbon atoms in R 5 and R 6 being 4 or less.
Claim 10
Dependent Claim
70 words
A 2-(trisubstituted phenylimino)-imidazoline compound as recited in claim 1 wherein R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo, ##STR22## R 5 =H or lower alkyl R 7 =2-hydroxylethyl, 2-hydroxylpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, but if R 3 =H then R 1 =R 2 =ethyl.
Claim 11
Dependent Claim
67 words
A 2-(trisubstituted phenylimino) imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR23## wherein R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR24## R 5 =H or lower alkyl, R 6 =H or lower alkyl, R 7 =2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of carbon atoms in R 5 and R 7 or R 6 and R 5 being 4 or less.
Claim 12
Dependent Claim
67 words
A 2-(trisubstituted phenylimino) imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR23## wherein R 1 =R 2 =ethyl R 3 =H, R 4 = ##STR24## R 5 =H or lower alkyl, R 6 =H or lower alkyl, R 7 =2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of carbon atoms in R 5 and R 7 or R 6 and R 5 being 4 or less.
Claim 13
Dependent Claim
77 words
A 2-(trisubstituted phenylimino)-imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR25## wherein R 1 =R 2 trifluoromethyl, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo and at least one of R 1 or R 2 =trifluoromethyl, ##STR26## R 5 =H or lower alkyl, R 7 =H, lower alkyl, 2-hydroxyethyl, 2-hydroxylpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, and R 4 =H.
Claim 14
Dependent Claim
77 words
A 2-(trisubstituted phenylimino)-imidazoline compound of the formula or a pharmaceutically acceptable salt thereof: ##STR25## wherein R 1 =R 2 trifluoromethyl, R 1 ≠R 2 =methyl, ethyl, trifluoromethyl, fluoro, chloro or bromo and at least one of R 1 or R 2 =trifluoromethyl, ##STR26## R 5 =H or lower alkyl, R 7 =H, lower alkyl, 2-hydroxyethyl, 2-hydroxylpropyl or 3-hydroxylpropyl, the sum of carbon atoms in R 5 and R 7 being 4 or less, and R 4 =H.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-07-24 | 1988-01-23 | 1988-07-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-07-24 | 1992-01-23 | 1992-07-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-07-24 | 1996-01-23 | 1996-07-24 | $7700.00 | Window Closed / Lapsed |