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US-12617756-B2 - Substituted imidazolidines for treating a RNA virus infection

US12617756B2US 12617756 B2US12617756 B2US 12617756B2US-12617756-B2

Abstract

A compound of formula (I) is: wherein: X 2 represents a —CO—NR k — group, a —NR′ k —CO— group, a —O— group, a —CO— group, a —SO 2 -group, a —CS—NH— group, a —CH 2 —NH—, a group, or a heterocyclyl, wherein the heterocyclyl is a 5- or 6-membered ring comprising 1, 2, 3 or 4 heteroatoms selected from O, S and/or N; Y 2 represents a hydrogen atom, a halogen atom, a hydroxyl group, a morpholinyl group, optionally substituted by a (C 1 -C 4 )alkyl group or a trifluoromethyl group, a bridged morpholinyl group, a (C 5 -C 11 )bicycloalkyl group, an adamantyl group, a piperidinyl group, a (C 1 -C 4 )alkenyl group, a —PO(OR a )(OR b ) group, a 5-membered heteroaromatic ring or a —CR 1 R 2 R 3 group, or any of its pharmaceutically acceptable salt.

Inventors

  • Didier Scherrer
  • Elisa AZZALI
  • Florence Mahuteau
  • Romain Najman
  • Jamal Tazi
  • Julien Santo
  • Cécile APOLIT
  • Frederic LABEGUERE
  • Brice SAUTIER
  • Natacha BIENVENU

Assignees

  • ABIVAX
  • CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
  • UNIVERSITE DE MONTPELLIER
  • INSTITUT CURIE

Dates

Publication Date
20260505
Application Date
20200717
Priority Date
20190719

Claims (19)

  1. 1 . A compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein: ring Z is phenylene or pyridinylene; ring Z′ is phenylene or pyridinylene; Z″ is —CH 2 — or —C(O)—; R g is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; R h is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; Q is —NH— or —O—; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F z or C 1 -C 4 alkyl; and R 2 is H, F z or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F z or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R a is independently H or C 1 -C 4 alkyl; each R b is independently H or C 1 -C 4 alkyl; n is 0, 1, 2, or 3; m is 0, 12 or 2; and m′ is 0, 1, or 2; with the proviso that no more than one of R 1 , R 2 , and R 3 is H.
  2. 2 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein: R g is H; and R h is H.
  3. 3 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein Q is —NH—.
  4. 4 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein: (i) ring Z′ is phenylene; and ring Z is phenylene; or (ii) ring Z′ is phenylene; and ring Z is pyridinylene.
  5. 5 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein: each R is independently C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, Cl, F, CN, or OC 1 -C 5 alkyl; wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; and wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and each R′ is independently C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, —CF 3 , furanyl, Cl, F, CN, or OC 1 -C 5 alkyl, wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; and wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —.
  6. 6 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein X 2 is —C(O)—, —C(O)NH—, —NHC(O)—, —O—, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, O, and S; and wherein the heterocyclyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, C 1 -C 4 alkyl, —C(O)OR p , and ═O.
  7. 7 . The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein Y 2 is H, halogen, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantyl, C 2 -C 4 alkenyl, —PO(OR a )(OR b ), oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, or —CR 1 R 2 R 3 ; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; and wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; one of (i) and (ii) is satisfied: (i) R 1 is H, F z or C 1 -C 4 alkyl; and R 2 is H, F z or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CF 3 , OH, CN, P(O)(OR a )(OR b ), and ═O; and wherein one or two CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —S—, —NH—, and —S(O) 2 —; and R 3 is H, F z or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—.
  8. 8 . The compound according to claim 1 , wherein the compound is selected from the group consisting of: N o Structure 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 or a pharmaceutically acceptable salt thereof.
  9. 9 . A pharmaceutical composition comprising at least one pharmaceutically acceptable excipient and at least one compound according to claim 1 , or a pharmaceutically acceptable salt thereof.
  10. 10 . A method for treating a respiratory syncytial virus (RSV) in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 1 , or a pharmaceutically acceptable salt thereof.
  11. 11 . A method for treating respiratory syncytial virus (RSV) infection in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 8 , or a pharmaceutically acceptable salt thereof.
  12. 12 . A method for treating a ribonucleic acid (RNA) virus infection in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 1 , or a pharmaceutically acceptable salt thereof.
  13. 13 . A method for treating a ribonucleic acid (RNA) virus infection in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 8 , or a pharmaceutically acceptable salt thereof.
  14. 14 . A process for manufacturing a compound of formula (I) according to claim 1 : wherein ring Z is phenylene or pyridinylene; ring Z′ is phenylene or pyridinylene; Z″ is —CH 2 — or —C(O)—; R g is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; R h is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; Q is —NH—; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R a is independently H or C 1 -C 4 alkyl; each R b is independently H or C 1 -C 4 alkyl; n is 0, 1, 2, or 3; m is 0, 1, or 2; and m′ is 0, 1, or 2; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; the process comprising the following steps: (i) coupling a compound of formula (II); wherein: R c is alkyl; ring Z′ is phenylene or pyridinylene; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; and m′ is 0, 1, or 2; with a compound of formula (III) wherein: X is Cl, Br, or I; ring Z is phenylene or pyridinylene; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R a is independently H or C 1 -C 4 alkyl; each R b is independently H or C 1 -C 4 alkyl; n is 0, 1, 2, or 3; and m is 0, 1, or 2; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; in the presence of an inorganic base, a diphosphine, and an organometallic catalyst, to obtain a compound of formula (IV); wherein: R c is alkyl; ring Z is phenylene or pyridinylene; ring Z′ is phenylene or pyridinylene; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R a is independently H or C 1 -C 4 alkyl; each R b is independently H or C 1 -C 4 alkyl; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; n is 0, 1, 2, or 3; m is 0, 1, or 2; and m′ is 0, 1, or 2; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; (ii) hydrolyzing the compound of formula (IV) above, to obtain a compound of formula (V): wherein: R c is H; ring Z′ is phenylene or pyridinylene; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m′ is 0, 1, or 2; ring Z is phenylene or pyridinylene; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m is 0, 1, or 2; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; n is 0, 1, 2, or 3; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R a is independently H or C 1 -C 4 alkyl; and each R b is independently H or C 1 -C 4 alkyl; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; (iii) reacting the compound of formula (V) above with a compound of the following formula: wherein: Z″ is —CH 2 — or —C(O)—; R, is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; and R h is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; in the presence of an organic base and a coupling agent, to obtain the compound of formula (I) above, wherein Q is —NH—.
  15. 15 . A process for manufacturing a compound of formula (I) according to claim 1 : wherein: ring Z is phenylene or pyridinylene; ring Z′ is phenylene or pyridinylene; Z″ is —CH 2 — or —C(O)—; R, is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; R h is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; Q is O—; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; each R a is independently H or C 1 -C 4 alkyl; each R b is independently H or C 1 -C 4 alkyl; n is 0, 1, 2, or 3; m is 0, 1, or 2; and m′ is 0, 1, or 2; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; the process comprising-at-least the following steps: (i) coupling a compound of formula (II′): wherein: R c is alkyl; ring Z′ is phenylene or pyridinylene; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; and m′ is 0, 1, or 2; with a compound of formula (III); wherein: X is F; ring Z is phenylene or pyridinylene; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m is 0, 1, or 2; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; n is 0, 1, 2, or 3; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R a is independently H or C 1 -C 4 alkyl; and each R b is independently H or C 1 -C 4 alkyl; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; in the presence of an inorganic base, to obtain a compound of formula (IV′); wherein: R c is alkyl; ring Z′ is phenylene or pyridinylene; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m′ is 0, 1, or 2; ring Z is phenylene or pyridinylene; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m is 0, 1, or 2; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; n is 0, 1, 2, or 3; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R a is independently H or C 1 -C 4 alkyl; and each R b is independently H or C 1 -C 4 alkyl; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; (ii) hydrolyzing the compound of formula (IV′) above, to obtain a compound of formula (V′): wherein: R c is H; ring Z′ is phenylene or pyridinylene; each R′ is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m′ is 0, 1, or 2; ring Z is phenylene or pyridinylene; each R is independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 6 cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, CF 3 , furanyl, halogen, CN, or OC 1 -C 5 alkyl; wherein one —CH 2 — group of each C 1 -C 4 alkyl is optionally and independently replaced by one group independently selected from the group consisting of —S(O)— and —S(O) 2 —; and wherein each C 1 -C 4 alkyl is optionally and independently substituted by one or more OH substituents; m is 0, 1, or 2; X 2 is —C(O)—NR k —, —NR′ k —C(O)—, —O—, —C(O)—, —S(O) 2 —, —C(S)—NH—, —CH 2 —NH—, -oxetan-3-ylene-NH, or 5- or 6-membered heterocyclyl; wherein the heterocyclyl comprises 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, S, and N; and wherein the heterocyclyl is optionally substituted by one or more substituents selected from the group consisting of C 1 -C 4 alkyl, halogen, —C(O)OR p , and ═O; R k is H or CH 3 ; R′ k is H or CH 3 ; each R p is independently C 1 -C 4 alkyl; n is 0, 1, 2, or 3; Y 2 is H, halogen, OH, morpholinyl, bridged morpholinyl, C 5 -C 11 bicycloalkyl, adamantlyl, piperidinyl, C 2 -C 4 alkenyl, —P(O)(OR a )(OR b ), 5-membered heteroaryl, or —CR 1 R 2 R 3 , wherein the heteroaryl comprises 1 or 2 heteroatom(s) independently selected from the group consisting of O and N; wherein the morpholinyl is optionally substituted by one or more substituents independently selected from the group consisting of C 1 -C 4 alkyl and —CF 3 ; wherein the bridged morpholinyl is optionally substituted by one or more independently selected halogen substituents; and wherein one —CH 2 — group of the piperidinyl is optionally replaced by one S(O) 2 group; one of (i) and (ii) is satisfied: (i) R 1 is H, F, or C 1 -C 4 alkyl; and R 2 is H, F, or C 1 -C 4 alkyl; or (ii) R 1 and R 2 , together with the carbon atom to which they are attached, form a C 3 -C 8 cycloalkyl; wherein the C 3 -C 8 cycloalkyl is optionally substituted by one or two independently selected C 1 -C 4 alkyl substituents; wherein each C 1 -C 4 alkyl substituent is optionally and independently substituted by one or more substituents independently selected from the group consisting of OH, halogen, CF 3 , CN, P(O)(OR a )(OR b ), ═O, and OC 1 -C 4 alkyl; and wherein one or two —CH 2 — groups of the C 3 -C 8 cycloalkyl are optionally and independently replaced by one or two groups independently selected from the group consisting of —O—, —NH—, —S—, and —S(O) 2 —; and R 3 is H, F, or C 1 -C 4 alkyl, wherein one —CH 2 — group of the C 1 -C 4 alkyl is optionally replaced by one —NH—; each R a is independently H or C 1 -C 4 alkyl; and each R b is independently H or C 1 -C 4 alkyl; with the proviso that no more than one of R 1 , R 2 , and R 3 is H; (iii) reacting the compound of formula (V′) above with a compound of the following formula: wherein: Z″ is —CH 2 — or —C(O)—; R, is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; and R h is H, C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, —CH 2 CHF 2 , or —C(O)CH 3 ; to obtain the compound of formula (I) above, wherein Q is —O—.
  16. 16 . A pharmaceutical composition comprising at least one pharmaceutically acceptable excipient and a compound selected from the group consisting of: No Structure 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118 119 120 121 122 123 124 125 126 127 128 129 130 131 132 133 134 135 136 137 138 139 140 141 142 143 144 145 146 147 148 149 150 151 152 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 or a pharmaceutically acceptable salt thereof.
  17. 17 . A compound selected from the group consisting of: 76 83 166 and 171 or a pharmaceutically acceptable salt thereof.
  18. 18 . A method for treating respiratory syncytial virus (RSV) infection in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 17 , or a pharmaceutically acceptable salt thereof.
  19. 19 . A method for treating a ribonucleic acid (RNA) virus infection in a subject, the method comprising administering to the subject in need thereof a therapeutically effective quantity of at least one compound according to claim 17 , or a pharmaceutically acceptable salt thereof.

Description

The present invention relates to new compounds useful for preventing and/or treating a RNA virus infection, and most preferably a RNA virus infection caused by RNA viruses belonging to group V of the Baltimore classification, more particularly Respiratory Syncytial Virus (RSV) infection. The present invention further relates to the use of said compounds, in particular useful for preventing and/or treating a RNA virus infection, and most preferably a RNA virus infection caused by a RNA virus belonging to group V of the Baltimore classification, more particularly Respiratory Syncytial Virus (RSV) infection. It further relates to the pharmaceutical compositions containing said new compounds and to the chemical synthesis processes for obtaining them. BACKGROUND Viruses are one of the major causes of diseases around the world. Viruses are generally defined as small, non-living, infectious agents that replicate only within living cells, as they do not possess a completely autonomous replication mechanism. Although diverse in shape and size, they typically consist of a virus particle (known as a “virion”), made from a protein coat which comprises at least one nucleic acid molecule and optionally, depending on the type of virus, one or more proteins or nucleoproteins. Because viruses do not possess a completely autonomous replication mechanism, they must necessarily rely on the machinery and metabolism of the infected cell or host, in order to replicate and produce multiple copies of themselves. Even though their replication cycle varies greatly between species, it is generally recognized that the life cycle of viruses includes six basic steps: attachment, penetration, uncoating, replication, assembly and release. Depending on the nature of the targeted virus, therapeutic molecules have been designed which may interfere with one or more of those mechanisms. Among those, the replication step involves not only the multiplication of the viral genome, but also the synthesis of viral messenger RNA, of viral protein, and the modulation of the transcription or translation machinery of the host. However, it is also clear that the type of genome (single-stranded, double-stranded, RNA, DNA . . . ) characterizes dramatically this replication step. For instance, most DNA viruses assemble in the nucleus while most RNA viruses develop solely in the cytoplasm. Also, there is increasing evidence that single-stranded RNA viruses such as Influenza use the host RNA splicing and maturation machinery. Accordingly, and considering the implications of a given type of genome in the replication step, the Baltimore classification of viruses was developed. This classification clusters viruses into families (or “groups”) depending on their type of genome. The present virus classification, as in 2018, comprises seven different groups: Group I: double-stranded DNA viruses (dsDNA);Group II: single-stranded DNA viruses (ssDNA);Group III: double-stranded RNA viruses (dsRNA);Group IV: (+)strand or sense RNA viruses ((+)ssRNA);Group V: (−)strand or antisense RNA viruses ((−)ssRNA);Group VI: single-stranded RNA viruses having DNA intermediates (ssRNA-RT);Group VII: double-stranded DNA viruses having RNA intermediates (dsDNA-RT). According to that classification, viruses belonging to the Group VI are not, stricto sensu, RNA viruses. For the same reasons, viruses belonging to the Group VII are not, stricto sensu, DNA viruses. One well-studied example of a virus family belonging to the Group VI is the family Retroviridae (retrovirus) which includes HIV. One well-studied example of a virus family belonging to the Group VII is the family Hepadnaviridae which includes the Hepatitis B virus (HBV). As a representative of viruses pertaining to group V one may cite the Filoviridae virus family encompassing the Ebola virus, the Paramyxoviridae family encompassing the Respiratory Syncytial virus (RSV), the Rhabdoviridae family, the Orthomyxoviridae family encompassing the Influenzavirus A, Influenzavirus B and Influenzavirus C. Groups within the virus families particularly focused in the framework of the present invention are the ones encompassing RNA viruses, especially single-stranded RNA viruses, and more specifically RNA viruses belonging to group V of the Baltimore classification. There are few cures for diseases caused by RNA virus infections, in particular single-stranded RNA viruses, and more specifically RNA virus infections from viruses belonging to group V of the Baltimore classification. Treatment is focused on relieving the symptoms. Therefore, there is still a need to identify new antiviral drugs, in particular small chemical molecules, to treat RNA virus infections, such as RNA virus infections from group V, more particularly Respiratory Syncytial Virus (RSV) infection. Definitions As used herein, the term “patient” refers to either an animal, such as a valuable animal for breeding, company or preservation purposes, or preferably a human or a huma