US4556670A
Expired / Lapsed
US
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Spiro-3-hetero-azolones for treatment of diabetic complications
Assignee: Pfizer Inc
•
Filing: 1983-10-28
•
Granted: 1985-12-03
•
Expires: 2003-10-28
Abstract
Abstract Spiro-oxazolidones, -thiazolidones and -imidazolidones are disclosed which are useful as aldose reductase inhibitors and as therapeutic agents for the treatment of complications arising from diabetes. Pharmaceutical compositions containing the spiro compounds and a method of treating diabetic complications are also disclosed.
Inventors
- 👤 Christopher A. Lipinski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:52
CPC Classifications
C; C07; C07D; C07D235/00; C07D235/02; C07D263/00; C07D263/52; C07D277/00; C07D277/60
Claims Analysis
Total Claims: 61
Claim 1
Independent Claim
138 words
A compound of the formula ##STR6## or a pharmaceutically acceptable salt thereof, wherein: U is oxygen, sulfur or nitrogen substituted with hydrogen or alkyl having 1-4 carbon atoms; n is zero or one; W is carbonyl or hydroxymethylene; R is hydrogen or alkyl having 1-4 carbon atoms; X is hydrogen, chloro, bromo, iodo, alkyl having 1-4 carbon atoms, dimethy or (CH 2 ) m Q wherein m is 1 or 2 and Q is phenyl or halophenyl, with the proviso that when X is dimethyl, n is one; Y is hydrogen, halo, nitro, trifluoromethyl, alkoxy having 1-4 carbon atoms or alkyl having 1-4 carbon atoms; and Z is hydrogen, halo, nitro, trifluoromethyl, alkoxy having 1-4 carbon atoms or alkyl having 1-4 carbon atoms, with the proviso that if either Y or Z is nitro the other is hydrogen.
Claim 2
Dependent Claim
138 words
A compound of the formula ##STR6## or a pharmaceutically acceptable salt thereof, wherein: U is oxygen, sulfur or nitrogen substituted with hydrogen or alkyl having 1-4 carbon atoms; n is zero or one; W is carbonyl or hydroxymethylene; R is hydrogen or alkyl having 1-4 carbon atoms; X is hydrogen, chloro, bromo, iodo, alkyl having 1-4 carbon atoms, dimethy or (CH 2 ) m Q wherein m is 1 or 2 and Q is phenyl or halophenyl, with the proviso that when X is dimethyl, n is one; Y is hydrogen, halo, nitro, trifluoromethyl, alkoxy having 1-4 carbon atoms or alkyl having 1-4 carbon atoms; and Z is hydrogen, halo, nitro, trifluoromethyl, alkoxy having 1-4 carbon atoms or alkyl having 1-4 carbon atoms, with the proviso that if either Y or Z is nitro the other is hydrogen.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein U is oxygen.
Claim 4
Dependent Claim
10 words
A compound according to claim 2 wherein n is one.
Claim 5
Dependent Claim
10 words
A compound according to claim 3 wherein W is carbonyl.
Claim 6
Dependent Claim
10 words
A compound according to claim 4 wherein R is hydrogen.
Claim 7
Dependent Claim
17 words
A compound according to claim 5 wherein X is methyl, Y is fluoro and Z is hydrogen.
Claim 8
Dependent Claim
10 words
A compound according to claim 1 wherein U is sulfur.
Claim 9
Dependent Claim
13 words
A compound according to claim 1 wherein U is nitrogen substituted with hydrogen.
Claim 10
Dependent Claim
10 words
A compound according to claim 8 wherein n is zero.
Claim 11
Dependent Claim
10 words
A compound according to claim 9 wherein W is carbonyl.
Claim 12
Dependent Claim
10 words
A compound according to claim 10 wherein R is hydrogen.
Claim 13
Dependent Claim
14 words
A compound according to claim 11 wherein X, Y and Z are each hydrogen.
Claim 14
Dependent Claim
17 words
A compound according to claim 11 wherein X and Z are each hydrogen and Y is fluoro.
Claim 15
Dependent Claim
10 words
A compound according to claim 9 wherein W is hydroxymethylene.
Claim 16
Dependent Claim
10 words
A compound according to claim 14 wherein R is hydrogen.
Claim 17
Dependent Claim
14 words
A compound according to claim 15 wherein X, Y and Z are each hydrogen.
Claim 18
Dependent Claim
17 words
A compound according to claim 15 wherein X and Z are each hydrogen and Y is fluoro.
Claim 19
Dependent Claim
10 words
A compound according to claim 8 wherein n is one.
Claim 20
Dependent Claim
10 words
A compound according to claim 18 wherein W is carbonyl.
Claim 21
Dependent Claim
10 words
A compound according to claim 19 wherein R is hydrogen.
Claim 22
Dependent Claim
10 words
A compound according to claim 20 wherein X is hydrogen.
Claim 23
Dependent Claim
12 words
A compound according to claim 21 wherein Y and Z are hydrogen.
Claim 24
Dependent Claim
14 words
A compound according to claim 21 wherein Y is fluoro and Z is hydrogen.
Claim 25
Dependent Claim
12 words
A compound according to claim 23 which is the positively rotating enantiomer.
Claim 26
Dependent Claim
10 words
A compound according to claim 20 wherein X is bromo.
Claim 27
Dependent Claim
13 words
A compound according to claim 25 wherein Y and Z are each hydrogen.
Claim 28
Dependent Claim
10 words
A compound according to claim 20 wherein X is methyl.
Claim 29
Dependent Claim
14 words
A compound according to claim 27 wherein Y is fluoro and Z is hydrogen.
Claim 30
Dependent Claim
12 words
A compound according to claim 28 which is the positively rotating enantiomer.
Claim 31
Dependent Claim
10 words
A compound according to claim 20 wherein X is dimethyl.
Claim 32
Dependent Claim
14 words
A compound according to claim 30 wherein Y is chloro and Z is hydrogen.
Claim 33
Dependent Claim
10 words
A compound according to claim 19 wherein R is alkyl.
Claim 34
Dependent Claim
10 words
A compound according to claim 32 wherein R is methyl.
Claim 35
Dependent Claim
10 words
A compound according to claim 33 wherein X is methyl.
Claim 36
Dependent Claim
10 words
A compound according to claim 34 wherein Z is hydrogen.
Claim 37
Dependent Claim
10 words
A compound according to claim 35 wherein Y is fluoro.
Claim 38
Dependent Claim
10 words
A compound according to claim 18 wherein W is hydroxymethylene.
Claim 39
Dependent Claim
10 words
A compound according to claim 37 wherein R is hydrogen.
Claim 40
Dependent Claim
14 words
A compound according to claim 38 wherein X, Y and Z are each hydrogen.
Claim 41
Dependent Claim
16 words
A compound according to claim 38 wherein X and Z are hydrogen and Y is fluoro.
Claim 42
Dependent Claim
13 words
A compound according to claim 1 wherein U is nitrogen substituted by alkyl.
Claim 43
Dependent Claim
13 words
A compound according to claim 41 wherein U is nitrogen substituted by methyl.
Claim 44
Dependent Claim
10 words
A compound according to claim 42 wherein n is one.
Claim 45
Dependent Claim
9 words
A compound according toclaim 43 wherein W is carbonyl.
Claim 46
Dependent Claim
10 words
A compound according to claim 44 wherein X is methyl.
Claim 47
Dependent Claim
10 words
A compound according to claim 45 wherein Z is hydrogen.
Claim 48
Dependent Claim
10 words
A compound according to claim 46 wherein Y is flouoro.
Claim 49
Dependent Claim
10 words
A compound according to claim 47 wherein R is alkyl.
Claim 50
Dependent Claim
10 words
A compound according to claim 48 wherein R is methyl.
Claim 51
Dependent Claim
10 words
A compound according to claim 47 wherein R is hydrogen.
Claim 52
Dependent Claim
39 words
A pharmaceutical composition suitable for oral, parenteral or topical administration comprising a pharmaceutically acceptable carrier or diluent and a compound as claimed in claim 1 in an amount effective for the treatment of ocular or neuritic diabetes-associated chronic complications.
Claim 53
Dependent Claim
39 words
A composition according to claim 51 wherein U is nitrogen substituted with a hydrogen, n is one, R is hydrogen, W is carbonyl, X and Z are hydrogen, Y is fluoro and the compound is the positively rotating enantiomer.
Claim 54
Dependent Claim
33 words
A composition according to claim 51 wherein U is nitrogen substituted with a hydrogen, n is one, R is hydrogen, W is carbonyl, X is methyl, Y is fluoro and Z is hydrogen.
Claim 55
Dependent Claim
14 words
A composition according to claim 53 wherein the compound is the positively rotating enantiomer.
Claim 56
Dependent Claim
42 words
A method for treating a diabetic host to prevent or alleviate ocular or neuritic diabetes-associated chronic complications, which comprises orally, parenterally or topically administering to said diabetic host an alleviating or prophylactically effective amount of a compound as claimed in claim 1.
Claim 57
Dependent Claim
39 words
A method according to claim 55 wherein U is nitrogen substituted with a hydrogen, n is one, R is hydrogen, W is carbonyl, X and Z are hydrogen, Y is fluoro and the compound is the positively rotating enantiomer.
Claim 58
Dependent Claim
33 words
A method according to claim 55 wherein U is nitrogen substituted with a hydrogen, n is one, R is hydrogen, W is carbonyl, X is methyl, Y is fluoro and Z is hydrogen.
Claim 59
Dependent Claim
14 words
A method according to claim 57 wherein the compound is the positively rotating enantiomer.
Claim 60
Dependent Claim
17 words
A compound according to claim 38 wherein X is methyl, Y is fluoro and Z is hydrogen.
Claim 61
Dependent Claim
12 words
A compound according to claim 59 which is the positively rotating enantiomer.
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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) | 1988-12-02 | 1989-06-03 | 1989-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-02 | 1993-06-03 | 1993-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-02 | 1997-06-03 | 1997-12-03 | $7700.00 | Window Closed / Lapsed |