Patent US4443465A successfully refreshed from Google Patents.
US4443465A
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Aldose reductase inhibitory pyrrole derivatives
Assignee: Imperial Chemical Industries Ltd
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Filing: 1982-05-11
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Granted: 1984-04-17
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Expires: 2002-05-11
Abstract
Abstract The invention provides an aldose reductase inhibitory pyrrole derivative of the formula: ##STR1## in which Ra is an optionally substituted benzyl or cinnamyl radical, and ring A is the benzene ring of an optionally substituted benzo[b]thiophene, benzo[b]furan, quinoline or N-alkylquinolone, together with pharmaceutically acceptable salts and non-toxic biodegradable precursors thereof. The compounds of formula I are useful in the treatment of prophylaxis of the side-effects of diabetes or galactosemia.
Inventors
- 👤 David R. Brittain
- 👤 Robin Wood
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:41
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/50; C07D333/52; C07D333/54; A; A61; A61P; A61P3/00; A61P3/08; A61P3/10; C07D495/00; C07D495/02; C07D495/04
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
87 words
A 1-substituted-spiro[4-pyrroline-3,4'-imidazolidine]-2,2',5'-trione of the formula: ##STR14## wherein Ra is a benzyl radical optionally bearing up to three substituents independently selected from halogeno, trifluoromethyl, (1-4 C)alkyl, (1-4 C)alkoxy, nitro, (1-4 C)alkylthio and cyano radicals; or a halogenocinnamyl radical; and ring A stands for the benzene ring of a benzo[b]thiophene or benzo[b]furan which may bear one or two substituents independently selected from (1-4 C)alkyl, (1-4 C)alkoxy and phenyl substituents located on the benzene or heterocyclic ring; or a pharmaceutically acceptable base-addition salt thereof; or a non-toxic, biodegradable precursor thereof.
Claim 2
Dependent Claim
87 words
A 1-substituted-spiro[4-pyrroline-3,4'-imidazolidine]-2,2',5'-trione of the formula: ##STR14## wherein Ra is a benzyl radical optionally bearing up to three substituents independently selected from halogeno, trifluoromethyl, (1-4 C)alkyl, (1-4 C)alkoxy, nitro, (1-4 C)alkylthio and cyano radicals; or a halogenocinnamyl radical; and ring A stands for the benzene ring of a benzo[b]thiophene or benzo[b]furan which may bear one or two substituents independently selected from (1-4 C)alkyl, (1-4 C)alkoxy and phenyl substituents located on the benzene or heterocyclic ring; or a pharmaceutically acceptable base-addition salt thereof; or a non-toxic, biodegradable precursor thereof.
Claim 3
Dependent Claim
84 words
A compound of formula I wherein Ra is a benzyl radical optionally bearing up to three substituents independently selected from fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, ethyl, methoxy, ethoxy, nitro, methylthio, ethylthio and cyano radicals; or a cinnamyl radical bearing one or two halogeno radicals independently selected from fluoro, chloro, bromo and iodo radicals; and ring A stands for the benzene ring of a benzo[b]thiophene or benzo[b]furan which may bear one or two substituents independently selected from methyl, ethyl, methoxy, ethoxy and phenyl radicals.
Claim 4
Dependent Claim
84 words
A compound of formula I wherein Ra is a benzyl radical optionally bearing up to three substituents independently selected from fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, ethyl, methoxy, ethoxy, nitro, methylthio, ethylthio and cyano radicals; or a cinnamyl radical bearing one or two halogeno radicals independently selected from fluoro, chloro, bromo and iodo radicals; and ring A stands for the benzene ring of a benzo[b]thiophene or benzo[b]furan which may bear one or two substituents independently selected from methyl, ethyl, methoxy, ethoxy and phenyl radicals.
Claim 5
Dependent Claim
20 words
A compound as claimed in claim 1 wherein Ra is a 4-halogeno-, 2,4-dihalogeno-, 3,4-dihalogeno- or 3,5-dihalogeno-benzyl, or a dihalogenocinnamyl radical;
Claim 6
Dependent Claim
25 words
A compound as claimed in claim 3 wherein Ra is a 4-bromo-, 4-bromo-2-fluoro-, 2-fluoro-4-iodo-, 3,4-dichloro-, 4-bromo-3-chloro- or 3,5-dichlorobenzyl, or a 4-chloro-, 4-bromo- or 3,4-dichloro-cinnamyl radical.
Claim 7
Dependent Claim
14 words
6'-(3,4-Dichlorobenzyl)-spiro[imidazoline-4,8'-thieno[3,2-e]indoline]-2,5,7'-trione; or a pharmaceutically acceptable base-addition salt thereof; or a non-toxic biodegradable precursor thereof.
Claim 8
Dependent Claim
14 words
6'-(3,4-Dichlorobenzyl)-spiro[imidazoline-4,8'-thieno[3,2-e]indoline]-2,5,7'-trione; or a pharmaceutically acceptable base-addition salt thereof; or a non-toxic biodegradable precursor thereof.
Claim 9
Dependent Claim
26 words
A salt of a compound of formula I as claimed in claim 1 which is an alkali metal, alkaline earth metal, aluminium, ammonium or triethanolamine salt.
Claim 10
Dependent Claim
52 words
A pharmaceutical composition suitable for inhibiting the enzyme aldose reductase which comprises as active ingredient an effective amount of a 1-substituted-spiro[4-pyrroline-3,4'-imidazolidine]-2-2', 5-trione of the formula I, or a pharmaceutically acceptable base-addition salt thereof, or a non-toxic biodegradable precursor thereof, as claimed in claim 1; together with a pharmaceutically acceptable diluent or carrier.
Claim 11
Dependent Claim
20 words
A composition as claimed in claim 7 which is in a form suitable for oral, parenteral, rectal or topical administration.
Claim 12
Dependent Claim
51 words
A method of inhibiting the enzyme aldose reductase in a warm-blooded animal requiring such treatment which comprises administering to said animal an aldose reductase inhibitory amount of a 1-substituted-sprio[4-pyrroline-3,4'-imidazolidine]-2,2',5'-trione of the formula I, or a pharmaceutically acceptable base-addition salt thereof, or a non-toxic biodegradable precursor thereof as claimed in 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) | 1987-04-17 | 1987-10-17 | 1988-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-04-17 | 1991-10-17 | 1992-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-04-17 | 1995-10-17 | 1996-04-17 | $7700.00 | Window Closed / Lapsed |