US4533667A
Expired / Lapsed
US
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Imidazolidinedione derivatives
Assignee: Pfizer Inc
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Filing: 1984-04-16
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Granted: 1985-08-06
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Expires: 2004-04-16
Abstract
Abstract A series of novel spiro-oxindole imidazolidinedione derivatives have been prepared, including their pharmaceutically acceptable salts. These compounds are useful in therapy as aldose reductose inhibitors for the control of certain chronic diabetic complications. Preferred compounds include 6'-amino-spiro-[imidazolidine-4,3'-indoline]-2,2',5-trione, 5'-chloro-7'-aminospiro-[imidazolidine-4,3'-indoline]-2,2',5-trione, 1'-(3-pyridylmethyl)-5'-fluoro-spiro-[imidazolidine-4,3'-indoline]-2,2 ',5-trione, 1'-(3-pyridylmethyl)-5',7'-dichloro-spiro-[imidazolidine-4,3'-indoline ]-2,2',5-trione and spiro-[imidazolidine-4,3'-(6-azaindoline)]-2,2',5-trione. Methods for preparing these compounds from known starting materials are provided.
Inventors
- 👤 Alan J. Hutchison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 07:19
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/10
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
187 words
A compound selected from the group consisting of spiro-hydantoin derivatives of the formulae: ##STR3## and the pharmaceutically acceptable salts thereof, wherein X and Y are each hydrogen, fluorine, chlorine, bromine, nitro or amino; Z is hydrogen or amino, with the proviso that at least one of X, Y and Z is amino and with the further proviso that said Z is always other than amino when at least one of X and Y is other than hydrogen; R is hydrogen; ═A--B═D-- of formula II represents ═N--CH═CH--, ═CH--CH═N-- or ═CH--N═CH--; R' is a member selected from the group consisting of hydrogen, alkyl having from one to four carbon atoms, aryl and aralkyl having up to three carbon atoms in the alkyl moiety wherein each of said aryl moieties is chosen from the group consisting of pyridyl, thienyl, phenyl and mono and di-substituted phenyl, with each ring substituent being chosen from the group consisting of fluorine, chlorine, bromine, alkyl and alkoxy each having up to four carbon atoms and trifluoromethyl; and R" is hydrogen, hydroxy, fluorine, chlorine, alkyl or alkoxy each having up to four carbon atoms or trifluoromethyl.
Claim 2
Dependent Claim
187 words
A compound selected from the group consisting of spiro-hydantoin derivatives of the formulae: ##STR3## and the pharmaceutically acceptable salts thereof, wherein X and Y are each hydrogen, fluorine, chlorine, bromine, nitro or amino; Z is hydrogen or amino, with the proviso that at least one of X, Y and Z is amino and with the further proviso that said Z is always other than amino when at least one of X and Y is other than hydrogen; R is hydrogen; ═A--B═D-- of formula II represents ═N--CH═CH--, ═CH--CH═N-- or ═CH--N═CH--; R' is a member selected from the group consisting of hydrogen, alkyl having from one to four carbon atoms, aryl and aralkyl having up to three carbon atoms in the alkyl moiety wherein each of said aryl moieties is chosen from the group consisting of pyridyl, thienyl, phenyl and mono and di-substituted phenyl, with each ring substituent being chosen from the group consisting of fluorine, chlorine, bromine, alkyl and alkoxy each having up to four carbon atoms and trifluoromethyl; and R" is hydrogen, hydroxy, fluorine, chlorine, alkyl or alkoxy each having up to four carbon atoms or trifluoromethyl.
Claim 3
Dependent Claim
22 words
A compound as claimed in claim 1 of the formula I wherein X is chlorine, Y is amino and Z is hydrogen.
Claim 4
Dependent Claim
22 words
A compound as claimed in claim 1 of the formula I wherein X and Y are each hydrogen and Z is amino.
Claim 5
Dependent Claim
15 words
A compound as claimed in claim 1 of the formula II wherein ═A--B═D-- is ═N--CH═CH--.
Claim 6
Dependent Claim
15 words
A compound as claimed in claim 1 of the formula II wherein ═A--B═D-- is ═CH--CH═N--.
Claim 7
Dependent Claim
15 words
A compound as claimed in claim 1 of the formula II wherein ═A--B═D-- is ═CH--N═CH--.
Claim 8
Dependent Claim
14 words
A compound as claimed in claim 6 wherein R' and R" are each hydrogen.
Claim 9
Dependent Claim
22 words
A compound as claimed in claim 6 wherein R' is alkyl having from one to four carbon atoms and R" is hydrogen.
Claim 10
Dependent Claim
11 words
A compound as claimed in claim 8 wherein R' is isopropyl.
Claim 11
Dependent Claim
26 words
A compound as claimed in claim 6 wherein R' is mono-substituted phenylalkyl having up to three carbon atoms in the alkyl moiety and R" is hydrogen.
Claim 12
Dependent Claim
11 words
A compound as claimed in claim 10 wherein R' is p-chlorobenzyl.
Claim 13
Dependent Claim
26 words
A compound as claimed in claim 6 wherein R' is di-substituted phenylalkyl having up to three carbon atoms in the alkyl moiety and R" is hydrogen.
Claim 14
Dependent Claim
11 words
A compound as claimed in claim 12 wherein R' is 3,4-dichlorobenzyl.
Claim 15
Dependent Claim
33 words
A compound as claimed in claim 6 wherein R' is mono-substituted phenylalkyl having up to three carbon atoms in the alkyl moiety and R" is alkyl having from one to four carbon atoms.
Claim 16
Dependent Claim
15 words
A compound as claimed in claim 14 wherein R' is p-fluorobenzyl and R" is methyl.
Claim 17
Dependent Claim
16 words
A compound as claimed in claim 6 wherein R' is mono-substituted phenyl and R" is hydrogen.
Claim 18
Dependent Claim
11 words
A compound as claimed in claim 16 wherein R' is p-fluorophenyl.
Claim 19
Dependent Claim
31 words
A pharmaceutical composition suitable for oral administration comprising a pharmaceutically acceptable carrier and a compound as claimed in claim 1 in an amount effective for the treatment of diabetes-associated chronic complications.
Claim 20
Dependent Claim
35 words
A method for treating a diabetic host to prevent or alleviate chronic complications arising in said host, which comprises administering to said diabetic host an effective amount of a compound 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) | 1988-08-05 | 1989-02-04 | 1989-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-05 | 1993-02-04 | 1993-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-05 | 1997-02-04 | 1997-08-06 | $7700.00 | Window Closed / Lapsed |