Claims
- 1. A compound of formula (I), ##STR126## its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates where one of X, Y or Z represent C.dbd.O or C.dbd.S and one of the remaining of X, Y, and Z represent C.dbd. and the other of the remaining X, Y, and Z represent C.dbd.C; R.sup.1, R.sup.2 and R.sup.3 are substituents either on X, Y or Z or on a nitrogen atom and may be the same or different and represent hydrogen, halogen, hydroxy or nitro, or optionally substituted groups selected from alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, aralkyl, heterocyclyl, heteroaryl, heteroaralkyl, aryl, acyloxy, hydroxyalkyl, amino, acylamino, arylamino, aminoalkyl, aryloxy, alkoxycarbonyl, alkylamino, alkoxyalkyl, thioalkyl, alkylthio or carboxylic acid and its derivatives with the provision that when R.sup.1, R.sup.2 or R.sup.3 is on a nitrogen atom it does not represent hydrogen, halogen, nitro, carboxy or sulfonic acid groups; or any two of R.sup.1, R.sup.2 and R.sup.3 along with the adjacent atoms to which they are attached may form a substituted or unsubstituted cyclic structure of 4 to 7 atoms with one or more double bonds which may be carbocyclic or may contain one or more heteroatoms selected from oxygen, nitrogen and sulfur; the linking group represented by (CH.sub.2).sub.n --O-- may be attached either through nitrogen atom or through X, Y or Z where n is an integer ranging from 1-4; Ar represents an optionally substituted divalent aromatic or heterocyclic group; R.sup.4 represents hydrogen, halogen or lower alkyl group or forms a bond together with the adjacent group A; A represents a nitrogen atom or a group CR.sup.5 where R.sup.5 represents hydrogen, halogen or lower alkyl group or R.sup.5 forms a bond together with R.sup.4 ; B represents an oxygen or a sulfur atom when A is CR.sup.5 and B represents an oxygen atom when A is a nitrogen atom.
- 2. A compound according to claim 1, wherein X is a C.dbd.O or C.dbd.S and one of Y and Z is C.dbd. and the other of Y and Z is C.dbd.C.
- 3. A compound according to claim 1, wherein Y is a C.dbd.O or C.dbd.S and one of X and Z is C.dbd. and the other of Y and Z is C.dbd.C.
- 4. A compound according to claim 1, wherein Z is a C.dbd.O or C.dbd.S and one of X and Y is C.dbd. and the other of Y and Z is C.dbd.C.
- 5. A compound according to claim 1, wherein R.sup.1, R.sup.2 and R.sup.3 are substituents on X, Y or Z which may be same or different and are selected from hydrogen, halogen, hydroxy, nitro, or optionally substituted groups selected from alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, aralkyl heterocyclylheteroaryl, heteroaralkyl, acyl, acyloxy, hydroxyalkyl, amino, acylamino, arylamino, aminoalkyl, aryloxy, alkoxycarbonyl, alkylamino, alkoxyalkyl, thioalkyl, alkylthio or carboxy or its derivatives or sulfonic acid or its derivatives.
- 6. A compound according to claim 1, wherein one of R.sup.1, R.sup.2 or R.sup.3 is substituent on a nitrogen atom and is selected from the group consisting of substituted or unsubstituted (C.sub.1 -C.sub.12)alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; substituted or unsubstituted aralkyl; substituted or unsubstituted heteroaryl; substituted or unsubstituted heterocyclyl; alkoxycarbonyl; aryloxycarbonyl; amino(C.sub.1 -C.sub.6)alkyl; hydroxy(C.sub.1 -C.sub.6)alkyl; thio(C.sub.1 -C.sub.6)alkyl and acyl groups.
- 7. A compound according to claim 1, wherein the cyclic structure formed by any two of R.sup.1, R.sup.2 or R.sup.3 along with the adjacent atoms to which they are attached, is substituted and the substituents are selected from the group consisting of halogen, alkyl, cycloalkyl, alkoxy, cycloalkoxy, aryl, aralkyl, heterocyclyl, heteroaryl, heteroaralkyl, hydroxy, acyl, acyloxy, hydroxyalkyl, amino, acyl, acyloxy, acylamino, aminoalkyl, aryloxy, alkoxycarbonyl, alkylamino, alkoxyalkyl, carboxylic acid or its derivatives or sulfonic acid or its derivatives.
- 8. A pharmaceutical composition which comprises a compound of formula (I) ##STR127## as defined in claim 1 and pharmaceutically acceptable carriers, diluents or solvates.
- 9. A pharmaceutical composition as claimed in claim 8, in the form of a tablet, capsule, powder, syrup, solution or suspension.
- 10. A compound according to claim 1 where Ar represents substituted or unsubstituted divalent phenylene, naphthylene, benzofuryl, indolinyl, azaindolyl, azaindolinyl or benzoxazolyl.
- 11. A compound according to claim 1 which is selected from the group consisting of the following compounds:
- 5-[4-[2-[2,4-dimethyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-butyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]thiazolidine-2,4-dione and its salts and its polymorphs,
- 5-[4-[[3-ethyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-methyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[6,7-dimethoxy-2-ethyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]oxazolidine-2,4-dione and its salts,
- 5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]oxazolidine-2,4-dione and its salts,
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]oxazolidine-2,4-dione and its salts,
- 2-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]-1,2,4-oxadiazolidine-3,5-dione and its salts,
- 2-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]-1,2,4-oxadiazolidine-3,5-dione and its salts,
- 2-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]-1,2,4-oxadiazolidine-3,5-dione and its salts,
- 5-[4-[2-[2,4-dimethyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-methyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[[3-ethyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-methyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[2-[2-ethyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]-3-methoxyphenyl methylene]thiazolidine-2,4-dione and its salts,
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]thiazolidine-2,4-dione, sodium salt and its polymorphs,
- 5-[4-[2-[2-methyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione, sodium salt.
- 5-[4-[2-[2-ethyl-4-oxo-3,4-dihydro-3-quinazolinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione, sodium salt.
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]thiazolidine-2,4-dione, potassium salt.
- 5-[4-[[3-methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methylene]thiazolidine-2,4-dione, sodium salt.
- 12. A composition which comprises a compound according to claim 11 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.
- 13. 5-[4-[[3-Methyl-4-oxo-3,4-dihydro-2-quinazolinyl]methoxy]phenyl methyl]thiazolidine-2,4-dione of the formula ##STR128##
- 14. A composition which comprises a compound according to claim 13 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1150/96 |
Jul 1996 |
INX |
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Parent Case Info
This application is a continuation in part of U.S. application Ser. No. 08/777,627, filed Dec. 31, 1996, now U.S. Pat. No. 5,885,997.
US Referenced Citations (21)
Foreign Referenced Citations (5)
Number |
Date |
Country |
570067 |
|
AUX |
008203A |
Feb 1980 |
EPX |
0139421 |
May 1985 |
EPX |
155845A |
Sep 1985 |
EPX |
0207581 |
Jan 1987 |
EPX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
777627 |
Dec 1996 |
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