US 2007/0191373 A1Published application

Heterocyclic compounds for use in the treatment of viral infections

OwnerChristopher McGuigan, Jan Balzarini +1inventors

InventorsChristopher McGuigan, Jan Balzarini, Erik De Clerq

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Abstract

6-substituted-3-substituted-3H-furo[2,3-d]pyrimidin-2-one and 6-substituted-2-substituted-furo[2,3-d]pyrimidine novel compounds are useful in the treatment of viral infection, in particular cytomegalovirus viral infection. The substituents are independently selected from alkyl, aryl, alkenyl and alkynyl. The preferred substituent at the 6 position is alkyl.

Claims25

Dependent claims

A chemical compound having the formula (I):

wherein:
R1 and R4 are independently selected from alkyl, aryl, alkenyl and alkynyl;
Z is selected from O, NH, S, Se, NR1 and (CH2), where n is 1 to 10, and CT2 where T may be the same or different and is selected from hydrogen, alkyl and halogens, and R5 is alkyl, alkenyl or aryl;
Y is selected from N, CH and CR6 where R6 is alkyl, alkenyl, alkynyl or aryl;
Q is selected from O, S, NH, N-alkyl, CH2, CHalkyl and C(alkyl)2;
U is selected from N and CR2, R2 is selected from hydrogen, alkyl, halogen, amino, alkylamino, dialkylamino, nitro, cyano, alkoxy, aryloxy, thiol, alkylthiol, arylthiol and aryl;
V is selected from N and CR3, where R3 is selected from hydrogen, alkyl, halogens, alkyloxy, aryloxy and aryl;
and
when a double bond exists between X and the ring atom to which Q is attached and Q is linked to the ring moiety by a single bond, X is selected from N, CH and CR7, where R7 is selected from alkyl, alkenyl, alkynyl and aryl;
and
when a double bond links Q to the ring moiety and a single bond exists between X and the ring atom to which Q is attached, R4 does not exist and X is NR8, where R8 is alkyl, alkenyl, alkynyl or aryl, except that when Y is N, R8 is not an alkyl or alkenyl group substituted at the fourth atom of the chain of said alkyl or alkenyl group, counted along the shortest route away from the ring moiety including any heteroatom present in said chain, by a member selected from OH, phosphate, diphosphate, triphosphate, phosphonate, diphosphonate, triphosphonate, and pharmacologically acceptable salts, derivatives and prodrugs thereof;
and pharmacologically acceptable salts, derivatives and prodrugs of compounds of formula I.

9 more elements

A compound selected from the group comprising:

6-Butyl-3-cyclopentyl-3H-furo[2,3-d]pyrimidin-2-one (139) [Cf2158]
6-Butyl-2-cyclopentyloxy-furo[2,3-d]pyrimidine (130) [Cf2159]
6-Heptyl-3-cyclopentyl-3H-furo[2,3-d]pyrimidin-2-one (140) [Cf2160]
6-Heptyl-2-cyclopentyloxy-furo[2,3-d]pyrimidine (141) [Cf2161]
6-Butyl-3-(1-ethyl-propyl)-3H-furo[2,3-d]pyrimidin-2-one (142) [Cf2194]
6-Butyl-2-(1-ethyl-propoxy)-furo[2,3-d]pyrimidine (143) [Cf2193]
6-Heptyl-3-(1-ethyl-propyl)-3H-furo[2,3-d]pyrimidin-2-one (144) [Cf2190]
6-Heptyl-2-(1-ethyl-propoxy)-furo[2,3-d]pyrimidine (145) [Cf2189]
6-Butyl-3-pentyl-3H-furo[2,3-d]pyrimidin-2-one (146) [Cf2195]
6-Butyl-2-pentyloxy-furo[2,3-d]pyrimidine (147) [Cf2327]
6-Heptyl-3-pentyl-3H-furo[2,3-d]pyrimidin-2-one (148) [Cf2192]
6-Heptyl-3-pentyloxy-3H-furo[2,3-d]pyrimidin-2-one (149) [Cf2191]
6-Heptyl-3-(tetrahydro-furan-2-yl)-3H-furo[2,3-d]pyrimidin-2-one (154) [Cf2196]
6-Decyl-2-propoxy-furo[2,3-d]pyrimidine Cf2303
6-Decyl-3-propyl-3H-furo[2,3-d]pyrimidin-2-one Cf2304
2-Butoxy-6-decyl-furo[2,3-d]pyrimidine Cf2305
3-Butyl-6-decyl-3H-furo[2,3-d]pyrimidin-2-one Cf2306
6-Decyl-2-pentyloxy-2,3-dihydrofuro[2,3-d]pyrimidine Cf2247
2-Cyclopentyloxy-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidine Cf2250
3-Cyclopentyl-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one Cf2251
2-(1′-Ethyl-propyloxy)-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidine Cf2252
3-(1′-Ethyl-propyl)-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one Cf2253
2-Cyclohexyloxy-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidine Cf2294
3-Cyclohexyl-6-decyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one Cf2295
6-Decyl-3-(tetrahydro-furan-2-ylmethyl)-3H-furo[2,3-d]pyrimidin-2-one 72 Cf2309
2-Cyclohexylmethoxy-6-decyl-furo[2,3-d]pyrimidine Cf2274
3-Cyclohexylmethyl-6-decyl-3H-furo[2,3-d]pyrimidin-2-one Cf2275
2-Benzyloxy-6-decyl-furo[2,3-d]pyrimidine Cf2307
3-Benzyl-6-decyl-3H-furo[2,3-d]pyrimidin-2-one Cf2308
6-Decyl-3-(tetrahydro-furan-2′-yl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one Cf2249
6-Decyl-2-(tetrahydro-furan-3-yloxy)-furo[2,3-d]pyrimidine 58
6-Decyl-3-(tetrahydro-furan-3-yl)-3H-furo]2,3-d]pyrimidin-2-one Cf2276
6-Decyl-2-(tetrahydro-furan-2-ylmethoxy)-furo[2,3-d]pyrimidine 71
6-Decyl-3-(tetrahydro-furan-2-ylmethyl)-3H-furo[2,3-d]pyrimidin-2-one 72
6-Decyl-2-(tetrahydro-pyran-2-ylmethoxy)-furo[2,3-d]pyrimidine 61
6-Decyl-3-(tetrahydro-pyran-2-ylmethyl)-3H-furo[2,3-d]pyrimidin-2-one 62
6-Decyl-2-(4-methoxybenzyloxy)-3H-furo[2,3-d]pyrimidine Cf2315
6-Decyl-3-(4-methoxybenzyl)-3H-furo[2,3-d]pyrimidin-2-one Cf2316
6-Decyl-2-(4-methylbenzyloxy)-3H-furo[2,3-d]pyrimidine Cf2313
6-Decyl-3-(4-methylbenzyl)-3H-furo[2,3-d]pyrimidin-2-one Cf2314
6-Hexyl-3-methyl-3H-furo[2,3-d]pyrimidin-2-one Cf2344
2-Butyloxy-6-hexyl-furo[2,3-d]pyrimidine Cf2346
2-Benzyloxy-6-hexyl-furo[2,3-d]pyrimidine Cf2348
3-Benzyl-6-hexyl-3H-furo[2,3-d]pyrimidin-2-one Cf2349.

41 more elements

Dependencies are inferred from the claim text.

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Abstract