Patent NZ-509457-A (NZ)
Title: Thiazolopyrimidine compounds suitable for the treatment of inflammatory disorders
Inventor: BAXTER ANDREW
IPC: A61K31/519
Filed: 1999-08-03
Abstract: A compound of general formula (I) wherein R1 represents a hydrogen atom, or a group -N3R4; R3 and R4 each independently represent a hydrogen atom, or a 4-piperidinyl, C3-C6 cycloalkyl or C1-C8 alkyl group, which latter two groups may be optionally substituted by one or more substituent groups independently selected from halogen atoms and -NR5R6, -CONR5R6, -OR7, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, morpholinyl, C1-C4alkyl, C3-C6cycloalkyl, tetrahydrofuranyl and aryl groups, wherein an aryl substituent group may be a phenyl, naphthyl, thienyl, pyridinyl, imidazolyl or indolyl group, each of which may be optionally substituted by one or more substituents independently selected from halogen atoms and cyano, nitro,-NR5R6 ,-CONR5R6, OR7, -NR8COR9, -S02NRSR6,-NR8S02R9, C1-C6 alkyl and trifluoromethyl groups, or R3 and R4 together with the nitrogen atom to which they are attached form a 4-to 7-membered saturated heterocyclic ring system, which may be optionally substituted by one or more substituent groups independently selected from a compound of formula (II), -NR5R6,-CONR5R6, -OR7, -COOR10, -NR8COR9, and C1-C6 alkyl optionally substituted by one or more substituents independently selected from halogen atoms and -NR11R12 and -OR7 groups; X represents an -OH or -NR13R14 group; R13 and R14 each independently represent a hydrogen atom, a 4-piperidinyl group optionally substituted by a C1-C4 alkylphenyl substituent group, or a C3-C7 carbocyclic, C1-C8 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group, which latter four groups may be optionally substituted by one or more substituent groups independently selected from halogen atoms and -NR5R6, -CONR5R6, -OR7, -COOR7, -NR8COR9, -SR10, -S02R10, -S02NR5R6, -NR8S02R9, morpholinyl, C1-C4 alkyl, C3-C6 cycloalkyl and aryl groups, wherein an aryl substituent group may be a phenyl, naphthyl, thienyl, pyridinyl, imidazolyl or indolyl group, each of which may be optionally substituted by one or more substituents independently selected from halogen atoms and cyano, nitro, -NR5R6,-CONR5R6, -OR7, -NR8COR9, -SO2NR5R6, NR8SO2R9, C1-C6 alkyl and trifluoromethyl groups, or R13 and R14 together with the nitrogen atom to which they are attached form a 4-to 7-membered saturated heterocyclic ring system, which ring system may be optionally substituted by one or more substituent groups independently selected from -NR5R6, -CONR5R6, -OR7, -COOR7, -NR8COR9, and C1-C6 alkyl optionally substituted by one or more substituents independently selected from halogen atoms and phenyl, -NR11R12 and -OR7 groups; R2 represents a C1-C6 alkyl or C2-C6 alkenyl group optionally substituted by a phenyl or phenoxy group, wherein the phenyl or phenoxy group may itself be optionally substituted by one or more substituents independently selected from halogen atoms and nitro, C1-C6 alkyl, trifluoromethyl, -OR7, -C(O)R7, -SR10, -NR15R16 and phenyl groups; R5 and R6 each independently represent a hydrogen atom or a C1-C6 alkyl or phenyl group, each of which may be optionally substituted by one or more substituent groups independently selected from halogen atoms, phenyl, -OR and -NR15R16, or R5 and R6 together with the nitrogen atom to which they are attached form a 4-to 7-membered saturated heterocyclic ring system optionally comprising a further heteroatom selected from oxygen and nitrogen atoms, which ring system may be optionally substituted by one or more substituent groups independently selected from phenyl, -OR17, -COOR17, -NR15R16, -CONR15R16, -1NR15COR16, -SONR15R16, and C1-C6 alkyl optionally substituted by one or more substituents independently selected from halogen atoms and -NR15R16 and -OR17 groups; R7 and R9 each independently represent a hydrogen atom or a C1-C6 alkyl or phenyl group, each of which may be optionally substituted by one or more substituent groups independently selected from halogen atoms, phenyl, -OR17 and -NR15R16; and each of R8, R10, R11, R12, R15, R16, and R17 independently represents a hydrogen atom or a C1-C6 alkyl or phenyl group; with the proviso that when R1 and X both represent -NH2, R2 does not represent a methyl group.