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US 6,686,390 B2Granted
Compounds having antiinflamatory activity: process for their preparation and pharmaceutical compositions containing them
AssigneeDr. Reddy's Laboratories, Inc.
InventorsManojit Pal, Koteswar Rao Yeleswarapu, Rajagopalan Ramanujam, Parimal Misra, Prem Kumar Mamnoor, Seshagiri Rao Casturi
Life of this patent
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Abstract
The present invention relates to novel heterocyclic compounds of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their regioisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.
Claims48
A compound of formula (I),
- wherein R1 represents amino or substituted or unsubstituted groups selected from alkyl, alkylamino, acylamino, cycloalkyl, cyclicamino, carboethoxycarbonylalkyl hydrazino, hydrazido, aminoacid residue, aryl, heteroaryl or —N═CR(NR)2 where R represents hydrogen or lower alkyl group;
- R2 represents halogen, hydroxy, cyano, nitro, azido, formyl, oximealkyl, thio or substituted or unsubstituted groups selected from amino, allyl, alkoxy, hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residue, amino acid residue alkyl, acyl, carbonyloxyalkyl, haloalkyl, aminoalkyl, haloalkoxy, hydroxyalkyl, alkoxyalkyl, thioalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, aryl, aralkyl, aryloxy, aralkoxy, aryloxyalkyl, aralkoxyalkyl, carboxamidoalkyl carbonylaminoalkyl groups or when the groups —S(═O)m—R1 and R2 are present on adjacent carbon atoms, R1 and R2 together with atoms to which they are attached also form a substituted or unsubstituted 5-7 membered cyclic structure containing carbon atoms, a sulfur atom and optionally contain one or two heteroatoms selected from O, S or N;
- R3 represents hydrogen, halogen atom, hydroxy, nitro, cyano, azido or substituted or unsubstituted groups selected from hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residues, alkyl, alkoxy, hydroxyalkyl, alkoxyalkyl, acylamino or amino groups;
- R4 and R5 are same or different and independently represent hydrogen, halogen, hydroxy, cyano, nitro, thio, hydroxylamino, substituted or unsubstituted groups selected from alkyl, alkoxy, acyl, acyloxy, amino, hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residues, aminoacyl, carboxyalkyl, carboxyalkenyl, aryl, aryloxy, aralkyl, aralkoxy, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, heteroaryl, heteroaryloxy, heteroaralkyl, heteroaralkoxy, heteroarylcarbonyl heteroaryloxycarbonyl, heteroaralkylcarbonyl, heteroaralkoxycarbonyl, heterocyclylcarbonyl, aminocarbonyl, aminocarbonylalkyl, carbonylamino, cycloalkylacylamino, alkylaminoalkoxy, alkylaminoacyl, carboxylic acid or its derivatives, saturated or partially saturated or aromatic single or fused 5 to 7 membered carbocycle ring or saturated or partially saturated or aromatic, single or fused 5 to 7 membered heterocycle ring;
- R6 represents hydrogen, halogen, hydroxy, amino, cyano, nitro, thio, hydroxylamino or unsubstituted or substituted groups selected from alkyl, alkoxy, or carboxyalkyl;
- R5 and R6 together represent ═C(Ra)(Rb), where Ra and Rb are same or different and independently represent hydrogen, substituted or unsubstituted (C1-C6)alkyl or aryl;
- ═O or ═NR7 where R7 represents hydrogen, aryl or heteroaryl group;
- X represents oxygen and m is an integer in the range of 0-2, its analogs, its tautomeric forms, its stereoisomers, its regioisomers, its polymorphs, its pharmaceutically acceptable salts, or its pharmaceutically acceptable solvates.
5 more elements
A process for the preparation of compound of formula (I),
- wherein R1 represents amino or substituted or unsubstituted groups selected from alkyl, alkylamino, acylamino, cycloalkyl, cyclicamino, carboethoxycarbonylalkyl, hydrazino, hydrazido, aminoacid residue, aryl, heteroaryl or —N═CR(NR)2 where R represents hydrogen or lower alkyl group;
- R2 represents halogen, hydroxy, cyano, nitro, azido, formyl, oximealkyl, thio or substituted or unsubstituted groups selected from amino, allyl, alkoxy, hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residue, aminoacid residue alkyl, acyl, carbonyloxyalkyl, haloalkyl, aminoalkyl, haloalkoxy, hydroxyalkyl, alkoxyalkyl, thioalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, aryl, aralkyl, aryloxy, aralkoxy, aryloxyalkyl, aralkoxyalkyl, carboxamidoalkyl, carbonylaminoalkyl groups or when the groups —S(═O)m—R1 and R2 are present on adjacent carbon atoms, R1 and R2 together with atoms to which they are attached also form a substituted or unsubstituted 5-7 membered cyclic structure containing carbon atoms, a sulfur atom and optionally contain one or two heteroatoms selected from O, S or N, R3 represents hydrogen, halogen atom, hydroxy, nitro, cyano, azido or substituted or unsubstituted groups selected from hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residues, alkyl, alkoxy, hydroxyalkyl, alkoxyalkyl, acylamino or amino groups, R4 and R5 are same or different and independently represent hydrogen, halogen, hydroxy, cyano, nitro, thio, hydroxylamino, substituted or unsubstituted groups selected from alkyl, alkoxy, acyl, acyloxy, amino, hydrazino, hydrazinoalkyl, hydrazido, hydrazidoalkyl, aminoacid residues, aminoacyl, carboxyalkyl, carboxyalkenyl, aryl, aryloxy, aralkyl, aralkoxy, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, heteroaryl, heteroaryloxy, heteroaralkyl, heteroaralkoxy, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroaralkylcarbonyl, heteroaralkoxycarbonyl, heterocyclylcarbonyl, aminocarbonyl, aminocarbonylalkyl, carbonylamino, cycloalkylacylamino, alkylaminoalkoxy, alkylaminoacyl, carboxylic acid or its derivatives, saturated or partially saturated or aromatic single or fused 5 to 7 membered carbocycle ring or saturated or partially saturated or aromatic, single or fused 5 to 7 membered heterocycle ring;
- R6 represents hydrogen, halogen, hydroxy, amino, cyano, nitro, thio, hydroxylamino or unsubstituted or substituted groups selected from alkyl, alkoxy, or carboxyalkyl;
- R5 and R6 together represent ═C(RaRb), where Ra and Rb are same or different and independently represent hydrogen, (C1-C6)alkyl or aryl;
- ═O or ═NR7, where R7 represents hydrogen, aryl or heteroaryl group;
- X represents oxygen and m is an integer in the range of 0-2;
- its analogs, its tautomeric forms, its stereoisomers, its regioisomers, its polymorphs, its pharmaceutically acceptable salts, or its pharmaceutically acceptable solvates, which comprises:
- (a) reacting compound of formula (II-1)
- where R1, R2, R3, R4 and m are as defined above, with carbon monoxide and water;
- or
- (b) reacting compound of formula (II-1)
- where all the symbols are as defined above, with a transition metal carbonyl complex.
9 more elements
A pharmaceutical composition, which comprises a compound as claimed 10 and a pharmaceutically acceptable carrier, diluent, excipient or solvate.
Dependencies are inferred from the claim text.