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US 6,958,344 B2Granted
Pyrimidine compounds and their use as modulators of chemokine receptor activity
AssigneeAstraZeneca AB
InventorsRoger Bonnert, Peter Cage, Fraser Hunt, Iain Walters, Paul Willis
Life of this patent
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Abstract
The invention provides certain heterocyclic compounds, processes, and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy; in formula (I), A is a group of formula (a) or (b).
Claims8
A compound of formula (I) and pharmaceutically acceptable salts or solvates thereof:
- in which:
- A is a group of formula (a) or (b):
- R1 represents a C3-C7 carbocydic, C1-C8 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group, the latter four groups may be optionally substituted by one or more substituent groups independently selected from halogen atoms, —OR4, —NR5R6, —CONR5R6, —COOR7, —NR8COR9, —SR10, —SO2R10, —SO2NR5R6, —NR8SO2R10, an aryl or heteroaryl group either of which can be optionally substituted by one or more substituents independently selected from halogen atoms, cyano, nitro, —OR4, —NR5R6, —CONR5R6, —COOR7, —NR8COR9, —SR10, —SO2R10, —SO2NR8R6, —NR5SO2R10, C1-C6 alkyl or trifluor
- R2 and R3 each independently represent hydrogen, a C3-C7 carbocyclic group, C1-C8 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group, the latter four groups may be optionally substituted by one or more substituent groups independently selected from halogen atoms , —OR4, —NR5R6, —CONR5R6, —COOR7, —NR8COR9, —SR10, —SO2R10, —SO2NR5R6, —NR8SO2R10 or
- a 3-8 membered ring optionally containing one or more atoms selected from O, S, NR8 and itself optionally substituted by C1-3-alkyl, halogen,
- R4 represents hydrogen, C1-C6 alkyl or a phenyl group the latter two of which maybe optionally substituted by one or more substituent groups independently selected from halogen atoms, phenyl, —OR11 and —NR12R13;
- R5 and R6 independently represent a hydrogen atom or a C1-C6 alkyl or phenyl group the latter two of which may be optionally substituted by one or more substituent groups independently selected from halogen atoms, phenyl, —OR14 and —NR15R16, —CONR15R16, —NR15COR6, —SO2NR15R16, NR15SO2R6 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, —OR14, —COOR14, NR15R16 —CONR15R16, —NR15COR16, —SO2NR15R16, NR15SO2R16 or C1-C6 alkyl itself optionally substituted by one or more substituents independently selected from halogen atoms and —NR15R16 and —OR17 groups;
- R10 represents a C1-C6 alkyl group or phenyl group, each of which may be optionally substituted by one or more substituent groups independently selected from halogen atoms, phenyl, —OR7 and —NR15R16;
- X is NH;
- Y is N ;
- and
- each of R7, R8, R9, R11, R12, R13, R14R15, R16, and R17, -independently represent a hydrogen atom, C1-C6, alkyl, or a phenyl group.
10 more elements
A compound selected from the group consisting of:
- 7,9-dihydro-6-[[(1R)-2-hydroxy-1-methylethyl]amino]-2-[(phenylmethyl)thio]-8H-purin-8-one,
- (2R)-2-[[8-amino-2-[[(2-fluorophenyl)methyl]thiol-]9H-purin-6-yl]amino]-1-propanol,
- 2-[[8-amino-2-[[(2,3-difluorophenyl)methyl]thio]-9H-purin-6-yl]amino]-1,3-propanediol,
- 2-[[8-amino-2-[[(2,3-difluorophenyl)methyl]thio]-9H-purin-6-yl]amino]-2methyl-1-propanol,
- 2-[[8-amino-2-[[(2,3-difluorophenyl)methyl]thio]-9H-purin-6-yl]amino]-1-butanol,
- 2-[[8-amino-2-[[(2,3-difluorophenymethyl]thio]9H-purin-6yl]amino]-2-methyl-1,3-propanediol,
- (2R)-2-[[8-amino-2-[[(2,3-difluorophenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- 2-[[8-amino-2-[[(2,3-difluorophenyl)methyl]thiol-9H-purin-6-yl]amino]-ethanol
- (2R)-2-[[8-amino-2-[[(3-chlorophenyl)methyl]thiol-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[(phenylmethyl)thio]9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(3-methylphenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(2-methylphenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(3-methoxypheny)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(4-methylphenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(2-bromophenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(3-chloro-2-fluorophenyl)methyl]thio]-9H-purin-6-yl]amino]-1-propanol,
- (2R)-2-[[8-amino-2-[[(3-chloro-4-methoxyphenyl)methyl]thio]-9H-purin]-6-yl]amino]-1-propanol, and
- (2R)-2-[[8-amino-2-](1,3-benzodioxol-4-ylmethyl)thio]-9H-purin-6-yl]amino]1-propanol,
- and their pharmaceutically acceptable salts and solvates.
16 more elements
Dependencies are inferred from the claim text.