| CPC C07D 401/12 (2013.01) [A61P 31/12 (2018.01); C07C 233/65 (2013.01); C07C 237/40 (2013.01); C07C 255/50 (2013.01); C07C 311/16 (2013.01); C07D 205/04 (2013.01); C07D 213/38 (2013.01); C07D 213/74 (2013.01); C07D 213/75 (2013.01); C07D 213/81 (2013.01); C07D 239/16 (2013.01); C07D 239/22 (2013.01); C07D 239/42 (2013.01); C07D 241/12 (2013.01); C07D 403/12 (2013.01); C07D 405/12 (2013.01); C07D 413/12 (2013.01); C07F 7/1804 (2013.01)] | 17 Claims |
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1. A compound of formula (Ic) or a pharmaceutically acceptable salt thereof:
 Z is phenylene or pyridylene,
Z′ is phenylene or pyridylene, where the ring is connected to the adjacent —C(O)— and —N(H)— in the para-orientation,
Z″ is —CH2— or —CO—,
Rg and Rh are each independently H or (C1-C4)alkyl,
X2 is —CO—NRk—, —NH—CO—NH—, —OCH2—, —CH(OH)—, —NH—CO—, —O—, —O—(CH2)s—O—, —CO—, —SO2—, —NH—SO2—, —NH—, —SO2—NH—, or a divalent 5-membered heteroaromatic ring comprising 1, 2, 3 or 4 heteroatoms,
wherein Rk is H or methyl,
n is 0, 1, 2, or 3,
s is 2 or 3,
R and R′ are each independently (C1-C4)alkyl optionally interrupted by —SO2- or —SO—, (C3-C6)cycloalkyl, trifluoromethyl, halogen, (C1-C5)alkoxy, —SO2—NRaRb, —SO3H, —OH, —O—SO2—ORc, or —O—P(═O)—(ORc)(ORd),
wherein m and m′ are independently 0, 1, or 2 and
Ra, Rb, Rc and Rd are independently H or (C1-C4)alkyl;
and
Y2 is H, halogen, hydroxyl, (Ci-C4)alkoxy, piperazinyl, piperidinyl, —CR1R2R3,
   or morpholinyl optionally substituted by (C1-C4)alkyl,
wherein Rf is (C1-C4)alkyl or cyano,
Rq and R′q are each independently H or methyl, and
R1, R2, and R3 are each independently H, F, or (C1-C4)alkyl, said (C1-C4)alkyl optionally substituted by trifluoromethyl and/or hydroxyl, with the proviso that no more than one of R1, R2, and R3 is a hydrogen atom,
or R1 and R2 are taken together with the carbon atom bearing them form a (C3-C8)cycloalkyl optionally interrupted by 1 or 2 oxygen ring atom(s) and optionally substituted by one or two (C1-C4)alkyl, halogen, hydroxy, or (C1-C4)alkoxy.
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14. A method of treating a RNA virus infection or a disease caused by a RNA virus belonging to group IV or V of the Baltimore classification, comprising administering a therapeutically effective amount of a compound of formula (Ic) according to claim 1, or a pharmaceutically acceptable salt thereof, to a patient in need thereof.
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15. The method according to claim 14, wherein the RNA virus infection caused by a RNA virus belonging to group IV or V of the Baltimore classification is selected from RSV infection, Chikungunya, influenza and Dengue.
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17. A process for the preparation of
a) a compound of formula (Ic) or a pharmaceutically acceptable salt thereof according to claim 1; or
b) a compound selected from 19-31 and 91-181
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or a pharmaceutically acceptable salt thereof;
comprising:
coupling a compound of the formula
 with a compound of the formula
 wherein, X is Cl, I, or Br,
in the presence of an inorganic base, a diphosphine, and an organometallic catalyst, to obtain:
a) a compound of formula (Ic) or a pharmaceutically acceptable salt thereof according to claim 1; or
b) a compound selected from 19-31 and 91-181, or a pharmaceutically acceptable salt thereof.
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