US4517199A
Expired / Lapsed
US
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Method for lowering intraocular pressure using phenylimino-imidazoles
Assignee: Alcon Research LLC
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Filing: 1983-08-03
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Granted: 1985-05-14
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Expires: 2003-08-03
Abstract
Abstract 2-(Trisubstituted phenylimino)-imidazole compounds also known as 2-(trisubstituted anilino)-1,3 diazacyclopentene-(2) compounds are used to lower intraocular pressure.
Inventors
- 👤 Billie M. York, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 18:27
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/44; C07D233/50; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/41; A61K31/415
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
217 words
A method for lowering intraocular pressure comprising topically applying to the eye an effective amount for lowering such intraocular pressure of a 2-(trisubstituted phenylimino)-imidazoline, or a pharmaceutically acceptable salt thereof, having the formula ##STR64## where R 1 , R 2 , R 3 and R 4 are defined in accordance with either I, II, or III as follows: I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo. R 1 ≠R 2 and each=methyl, ethyl, trifluoromethyl, fluoro, chloro and bromo, one of R 3 and R 4 is H and the other is selected from ##STR65## R 5 ≠R 6 =H or lower alkyl, R 5 =R 6 and each=H, lower alkyl, R 7 =H, lower alkyl 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of the carbon atoms in R 5 and R 6 or R 5 and R 7 being 4 or less, or ##STR66## R 8 =lower alkyl; II. R 1 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 2 =H, R 3 =is selected from ##STR67## R 4 =methyl, chloro or bromo R 9 =H or lower alkyl, R 10 =H, lower alkyl, 2-hydroxymethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of the carbon atoms in R 9 and R 10 being 4 or less; III. In no event shall said 2-(trisubstituted phenylimino)-imidazoline have the formula: ##STR68##
Claim 2
Independent Claim
217 words
A method for lowering intraocular pressure comprising topically applying to the eye an effective amount for lowering such intraocular pressure of a 2-(trisubstituted phenylimino)-imidazoline, or a pharmaceutically acceptable salt thereof, having the formula ##STR64## where R 1 , R 2 , R 3 and R 4 are defined in accordance with either I, II, or III as follows: I. R 1 =R 2 =methyl, ethyl, trifluoromethyl, chloro or bromo. R 1 ≠R 2 and each=methyl, ethyl, trifluoromethyl, fluoro, chloro and bromo, one of R 3 and R 4 is H and the other is selected from ##STR65## R 5 ≠R 6 =H or lower alkyl, R 5 =R 6 and each=H, lower alkyl, R 7 =H, lower alkyl 2-hydroxyethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of the carbon atoms in R 5 and R 6 or R 5 and R 7 being 4 or less, or ##STR66## R 8 =lower alkyl; II. R 1 =methyl, ethyl, trifluoromethyl, chloro or bromo, R 2 =H, R 3 =is selected from ##STR67## R 4 =methyl, chloro or bromo R 9 =H or lower alkyl, R 10 =H, lower alkyl, 2-hydroxymethyl, 2-hydroxypropyl or 3-hydroxypropyl, the sum of the carbon atoms in R 9 and R 10 being 4 or less; III. In no event shall said 2-(trisubstituted phenylimino)-imidazoline have the formula: ##STR68##
Claim 3
Dependent Claim
24 words
A method in accordance with claim 1 wherein the 2-(trisubstituted phenylimino)-imidazoline or salt is topically applied to the eye in a pharmaceutically acceptable vehicle.
Claim 4
Dependent Claim
31 words
A method in accordance with claim 2 wherein the concentration of the 2-(trisubstituted phenylimino)-imidazoline or salt is selected such that intraocular pressure is reduced without significantly affecting the central nervous system.
Claim 5
Dependent Claim
24 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 2,6-Dichloro-N 1 -(2-imidazolidinylidene)-1,4-benzenediamine having the structure: ##STR69## or pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
19 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 2,6-Dichloro-N 1 -(2imidazolidinylidene)-1,3-benzenediamine having the structure: ##STR70##
Claim 7
Dependent Claim
5 words
or pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
5 words
or pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
25 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 2,6-Diethyl-N 1 -(2-imidazolidinylidene)-1,4-benzenediamine having the structure of: ##STR71## or pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
22 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is N-[3,5-Diethyl-4-(2-imidazolidinyleneamino)-phenyl]-acetamidne having the structure: ##STR72## or pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
25 words
A method in accordance with claim 3 wherein the 2(trisubstituted phenylimino)-imidazoline is 3,5-Dichloro-4-(2-imidazolidinylideneamino)-phenol and esters thereof having the structure: ##STR73## or pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
25 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 3-chloro-5-methyl-4-(2-imidazolidinylideneamino)-benzoic acid ethyl ester having the structure: ##STR74## or pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
25 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 3-chloro-5-ethyl-4-(2-imidazolidinylideneamino)-benzoic acid ethyl ester having the structure: ##STR75## or pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
22 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is N-[3-chloro-5methyl-4-(2-imidazolidinylideneamino)-phenyl]-acetamide having the structure: ##STR76## or pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
26 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 2 chloro-6methyl-N 1 -(2-imidazolidinylidene)-1,4 benzenediamine having the structure: ##STR77## or pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
25 words
A method in accordance with claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 2-chloro-6ethyl-N 1 -(2-imidazolidinylidene)-1,4 benzenediamine having the structure: ##STR78## or pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
22 words
A method in accordance wtih claim 3 wherein the 2-(trisubstituted phenylimino)-imidazoline is 3-chloro-5methyl-4-(2-imidazolidinylideneamino)-benzenecarboxamide having the structure: ##STR79## or pharmaceutically acceptable salt thereof.
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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) | 1988-05-13 | 1988-11-12 | 1989-05-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-05-13 | 1992-11-12 | 1993-05-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-05-13 | 1996-11-12 | 1997-05-14 | $7700.00 | Window Closed / Lapsed |