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US 2004/0167335 A1Published application
Antiviral pyrazolopyridine compounds
AssigneeSmithKline Beecham Corporation
InventorsMui Cheung, Kristjan Gudmundsson, Brian A. Johns
Life of this patent
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Abstract
The present invention provides compounds of formula (I), pharmaceutical compositions containing the same, processes for preparing the same and their use as pharmaceutical agents. The compounds are useful in the prophylaxis treatment of herpes viral infections. 1
Claims36
A compound of formula (I):
- 86
- wherein:
- R1 is H;
- R2 is selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, Ay, Het, —OR7, —OAy, —OHet, —OR10Het, —S(O)nR9, —S(O)nAy, —S(O)nHet, —S(O)nNR7R8, —NR7R8, —NHHet, —NHR10Het, —NHR10Ay, —R10NR7R8 and —R10NR7Ay;
- each R7 and R8 are the same or different and are independently selected from the group consisting of H, alkyl, cycloalkyl, alkenyl, cycloalkenyl, —OR9, —C(O)R9, —CO2R9, —C(O)NR9R11, —C(S)NR9R11, —C(NH)NR9R11, —SO2R10, —SO2NR9R11, —R10cycloalkyl, —R10OR9, —R10NR9R11, —R10C(O)R9, —R10CO2R9, —R10C(O)NR9R11, —R10C(S)NR9R11, —R10NHC(NH)NR9R11, —R10C(NH)NR9R11, —R10SO2R10, —R10SO2NR9R11, —R10NHSO2R9, —R10NHCOR9 and —R10SO2NHCOR9;
- each R9 and R11 are the same or different and are independently selected from the group consisting of H, alkyl, cycloalkyl, —R10cycloalkyl, —R10OH, —R10(OR10)w where w is 1-10, and —R10NR10R10;
- each R10 is the same or different and is independently selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl;
- n is 0, 1 or 2;
- Ay is aryl;
- Het is a 5- or 6-membered heterocyclic or heteroaryl group;
- Y is N or CH;
- R3 and R4 are the same or different and are each independently selected from the group consisting of H, halo, alkyl, cycloalkyl, alkenyl, Ay, Het, —OR7, —OAy, —C(O)R7, —C(O)Ay, —CO2R7, —CO2Ay, —SO2NHR9, —NR7R8, —NR7Ay, —NHHet, —NHR10Het, —R10OR7, —R10OAy, —R10NR7R8 and R10NR7Ay;
- q is 0, 1, 2, 3, 4 or 5;
- each R5 is the same or different and is independently selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, Ay, Het, —OR7, —OAy, —OHet, —C(O)R9, —CO2R9, —C(O)NR7R8, —C(O)Ay, —C(O)NR7Ay, —C(O)Het, —C(O)NHR10Het, —C(S)NR9R11, —C(NH)NR7R8, —C(NH)NR7Ay, —S(O)nR9, —S(O)2NR7R8, —S(O)2NR7Ay, —NR7R8, —NR7Ay, —NHHet, —NHR10Ay, —NHR10Het, —R10cycloalkyl, —R10OR9, —R10NR7R8, —R10NR7Ay, —R10C(O)R9, —R10CO2R9, —R10C(O)NR9R11, —R10C(S)NR9R11, —R10NHC(NH)NR9R11, —R10C(NH)NR9R11, —R10SO2R9, —R10SO2NHCOR9, —R10SO2NR9R11, cyano, nitro and azido;
- or
- two adjacent R5 groups together with the atoms to which they are bonded form a C5-6 cycloalkyl or aryl;
- p is 0, 1 or 2;
- and
- each R6 is the same or different and is independently selected from the group consisting of halo, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, Ay, Het, —OR7, —OAy, —OHet, —OR10Ay, —OR10Het, —C(O)R9, —CO2R9, —C(O)NR7R9, —C(O)Ay, —C(O)NR7Ay, —C(O)NHR10Ay, —C(O)Het, —C(O)NHR10Het, —C(S)NR9R11, —C(NH)NR7R8, —C(NH)NR7Ay, —S(O)nR9, —S(O)nAy, —S(O)nHet, —S(O)2NR7R8, —S(O)2NR7Ay, —NR7R8, —NR7Ay, —NHR10Ay, —NHHet, —NHR10Het, —R10cycloalkyl, —R10Ay, —R10Het, —R10OR9, —R10—O—C(O)R9, —R10—O—C(O)Ay, —R10—O—C(O)Het, —R10—O—S(O)nR9, —R10NR7R8, —R10NR7Ay, —R10C(O)R9, —R10CO2R9, —R10C(O)NR9R11, —R10C(S)NR9R11, —R10NHC(NH)NR9R11, —R10C(NH)NR9R11, —R10SO2R9, —R10SO2NHCOR9, —R10SO2NR9R11, cyano, nitro and azido;
- or
- two adjacent R6 groups together with the atoms to which they are bonded form a C5-6cycloalkyl or a 5- or 6-membered heterocyclic group containing 1 or 2 heteroatoms;
- wherein at least one R6 is selected from the group consisting of —NR7R8, —NR7Ay, —NHHet, —NHR10Ay and —NHR10Het;
- and
- wherein when Y is CH, R3 is not —NR7Ay;
- and pharmaceutically acceptable salts, solvates and physiologically functional derivatives thereof.
22 more elements
A compound selected from the group consisting of:
- N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo-[1,5-α]pyridin-5-amine;
- 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-amine;
- N-[3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-yl]methanesulfonamide;
- 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-6amine;
- N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-6-amine;
- 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(5-fluorophenyl)-N-isopropylpyrazolo[1,5-α]pyridin-6-amine;
- 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-α]pyridin-5-amine;
- 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-isopropylpyrazolo[1,5-α]pyridin-5-amine;
- N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-5-amine;
- and
- 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-N-isopropyl-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-5-amine;
- 4-Bromo-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-amine;
- 4-Chloro-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-5-amine;
- 4-Bromo-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-5-amine,
- 4-Chloro-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-methoxyphenyl)pyrazolo[1,5-α]pyridin-5-amine;
- N-Butyl-3-[2-(butylamino)pyridin-4-yl]-2-(4-fluorophenyl)pyrazolo-[1,5-α]pyridin-4-amine;
- 4-{5-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-α]pyridin-2-yl}phenol;
- N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-isobutoxyphenyl)pyrazolo[1,5-α]pyridin-5-amine;
- and
- N-Cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-[4-(cyclopropylmethoxy)phenyl]pyrazolo[1,5-α]pyridin-5-amine, and
- pharmaceutically acceptable salts, solvates and physiologically functional derivatives thereof.
18 more elements
Dependencies are inferred from the claim text.