US4282246A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antidiabetic furancarboxylic and thiphenecarboxylic acids
Assignee: Pfizer Inc
•
Filing: 1980-03-07
•
Granted: 1981-08-04
•
Expires: 2000-03-07
Abstract
Abstract Compounds of the structure <IMAGE> wherein Z is oxygen or sulfur; R is (C1-C2)alkoxy; phenoxy; benzyl; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C1-C3)alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5- positions with methyl, methoxy, chloro, or fluoro; 2,3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; (C2-C6)alkylthio; or halo (bromo or chloro); and the pharmaceutically-acceptable salts thereof are useful in lowering the blood glucose levels of hyperglycemic mammals.
Inventors
- 👤 Gerald F. Holland
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:14
CPC Classifications
C; C07; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/26; C07D333/38; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/68
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
103 words
A method of lowering the blood glucose level in a hyperglycemic mammal which comprises administering a compound of structure ##STR3## wherein Z is oxygen or sulfur; R is (C 1 -C 2 )alkoxy; phenoxy; benzyl; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro; 2,3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; (C 2 -C 6 )alkylthio; or halo (bromo or chloro); or a pharmaceutically-acceptable salt thereof, to said hyperglycemic mammal in an amount sufficient to lower said blood glucose level.
Claim 2
Independent Claim
103 words
A method of lowering the blood glucose level in a hyperglycemic mammal which comprises administering a compound of structure ##STR3## wherein Z is oxygen or sulfur; R is (C 1 -C 2 )alkoxy; phenoxy; benzyl; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro; 2,3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; (C 2 -C 6 )alkylthio; or halo (bromo or chloro); or a pharmaceutically-acceptable salt thereof, to said hyperglycemic mammal in an amount sufficient to lower said blood glucose level.
Claim 3
Dependent Claim
12 words
A method of claim 1 wherein the compound is of structure ##STR4##
Claim 4
Dependent Claim
9 words
A method of claim 2 wherein Z is oxygen.
Claim 5
Dependent Claim
13 words
A method of claim 3 wherein R is methoxy, benzyl, phenylthiomethyl, or phenylthio.
Claim 6
Dependent Claim
9 words
A method of claim 4 wherein R is methoxy.
Claim 7
Dependent Claim
9 words
A method of claim 4 wherein R is benzyl.
Claim 8
Dependent Claim
9 words
A method of claim 4 wherein R is phenylthiomethyl.
Claim 9
Dependent Claim
9 words
A method of claim 4 wherein R is phenylthio.
Claim 10
Dependent Claim
9 words
A method of claim 2 wherein Z is sulfur.
Claim 11
Dependent Claim
13 words
A method of claim 9 wherein R is benzyl, phenylthio, 3-methylphenylthio or 3-chlorophenylthio.
Claim 12
Dependent Claim
12 words
A method of claim 1 wherein the compound is of structure ##STR5##
Claim 13
Dependent Claim
9 words
A method of claim 11 wherein Z is oxygen.
Claim 14
Dependent Claim
27 words
A method of claim 12 wherein R is phenylthio; 3- or 4-methylphenylthio; 2-, 3- or 4-chlorophenylthio; 2-, 3- or 4-fluorophenylthio; 2,5- or 3,5-difluorophenylthio; 2,3,5,6-tetrafluorophenylthio; 3-trifluoromethylphenylthio; or 2-naphthylthio.
Claim 15
Dependent Claim
9 words
A method of claim 13 wherein R is phenylthio.
Claim 16
Dependent Claim
9 words
A method of claim 13 wherein R is 3-chlorophenylthio.
Claim 17
Dependent Claim
9 words
A method of claim 13 wherein R is 2-fluorophenylthio.
Claim 18
Dependent Claim
9 words
A method of claim 13 wherein R is 3-fluorophenylthio.
Claim 19
Dependent Claim
9 words
A method of claim 11 wherein Z is sulfur.
Claim 20
Dependent Claim
9 words
A method of claim 18 wherein R is phenylthio.
Claim 21
Dependent Claim
12 words
A method of claim 1 wherein the compound is of structure ##STR6##
Claim 22
Dependent Claim
9 words
A method of claim 20 wherein Z is oxygen.
Claim 23
Dependent Claim
9 words
A method of claim 21 wherein R is phenylthio.
Claim 24
Dependent Claim
9 words
A method of claim 20 wherein Z is sulfur.
Claim 25
Dependent Claim
9 words
A method of claim 23 wherein R is phenylthio.
Claim 26
Dependent Claim
80 words
A pharmaceutical composition suitable for oral or parenteral administration which comprises an amount sufficient to lower the blood glucose level in a hyperglycemic animal of a compound of the structure ##STR7## wherein Z is oxygen or sulfur; R is (C 1 -C 2 )alkoxy; phenoxy; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro;
Claim 27
Dependent Claim
80 words
A pharmaceutical composition suitable for oral or parenteral administration which comprises an amount sufficient to lower the blood glucose level in a hyperglycemic animal of a compound of the structure ##STR7## wherein Z is oxygen or sulfur; R is (C 1 -C 2 )alkoxy; phenoxy; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro;
Claim 28
Dependent Claim
73 words
3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; or (C 2 -C 6 )alkylthio; and R 1 is phenoxy; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro; 2,3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; or (C 2 -C 6 )alkylthio; or a pharmaceutically-acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent.
Claim 29
Dependent Claim
73 words
3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; or (C 2 -C 6 )alkylthio; and R 1 is phenoxy; phenylthiomethyl; phenylthio; phenylthio monosubstituted in the 2-, 3- or 4-position with (C 1 -C 3 )alkyl, phenyl, methoxy, chloro, fluoro or trifluoromethyl; phenylthio disubstituted in the 2,5- or 3,5-positions with methyl, methoxy, chloro, or fluoro; 2,3,5,6-tetrafluorophenylthio; 1- or 2-naphthylthio; or (C 2 -C 6 )alkylthio; or a pharmaceutically-acceptable salt thereof, together with a pharmaceutically acceptable carrier or diluent.
Claim 30
Dependent Claim
14 words
A pharmaceutical composition of claim 25 wherein the compound is of the structure ##STR8##
Claim 31
Dependent Claim
14 words
A pharmaceutical composition of claim 26 wherein the compound is of the structure ##STR9##
Claim 32
Dependent Claim
14 words
A pharmaceutical composition of claim 26 wherein the compound is of the structure ##STR10##
Claim 33
Dependent Claim
14 words
A pharmaceutical composition of claim 28 wherein R 1 is phenylthio, 3-methylphenylthio or 3-chlorophenylthio.
Claim 34
Dependent Claim
14 words
A pharmaceutical composition of claim 25 wherein the compound is of the structure ##STR11##
Claim 35
Dependent Claim
10 words
A pharmaceutical composition of claim 30 wherein Z is oxygen.
Claim 36
Dependent Claim
28 words
A pharmaceutical composition of claim 31 wherein R is phenylthio; 3- or 4-methylphenylthio; 2-, 3- or 4-chlorophenylthio; 2-, 3- or 4-fluorophenylthio; 2,5- or 3,5-difluorophenylthio; 2,3,5,6-tetrafluorophenylthio; 3-trifluoromethylphenylthio; or 2-naphthylthio.
Claim 37
Dependent Claim
10 words
A pharmaceutical composition of claim 32 wherein R is phenylthio.
Claim 38
Dependent Claim
10 words
A pharmaceutical composition of claim 32 wherein R is 3-chlorophenylthio.
Claim 39
Dependent Claim
10 words
A pharmaceutical composition of claim 32 wherein R is 2-fluorophenylthio.
Claim 40
Dependent Claim
10 words
A pharmaceutical composition of claim 32 wherein R is 3-fluorophenylthio.
Claim 41
Dependent Claim
10 words
A pharmaceutical composition of claim 30 wherein Z is sulfur.
Claim 42
Dependent Claim
10 words
A pharmaceutical composition of claim 37 wherein R is phenylthio.
Claim 43
Dependent Claim
14 words
A pharmaceutical composition of claim 25 wherein the compound is of the structure ##STR12##
Claim 44
Dependent Claim
10 words
A pharmaceutical composition of claim 39 wherein Z is oxygen.
Claim 45
Dependent Claim
10 words
A pharmaceutical composition of claim 40 wherein R is phenylthio.
Claim 46
Dependent Claim
10 words
A pharmaceutical composition of claim 39 wherein Z is sulfur.
Claim 47
Dependent Claim
10 words
A pharmaceutical composition of claim 42 wherein R is phenylthio.
References Cited (Backward Citations)
US4011333A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-08-03 | 1985-02-02 | 1985-08-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-03 | 1989-02-02 | 1989-08-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-03 | 1993-02-02 | 1993-08-04 | $7700.00 | Window Closed / Lapsed |