ME01217B - Inhibitori replikacije virusa ljudske imunodeficijencije - Google Patents

Inhibitori replikacije virusa ljudske imunodeficijencije

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Publication number
ME01217B
ME01217B MEP-2010-192A MEP19210A ME01217B ME 01217 B ME01217 B ME 01217B ME P19210 A MEP19210 A ME P19210A ME 01217 B ME01217 B ME 01217B
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Montenegro
Prior art keywords
alkyl
bond
optionally substituted
cycloalkyl
het
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MEP-2010-192A
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English (en)
French (fr)
Inventor
Youla S Tsantrizos
Michael Boes
Christian Brochu
Craig Fenwick
Eric Malenfant
Stephen Mason
Marc Pesant
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Gilead Sciences Inc
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Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Publication of ME01217B publication Critical patent/ME01217B/me

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    • C07D311/14—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 6 and unsubstituted in position 7
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Claims (15)

1.Antropizomer, racemat, enantiomer, diastereomer ili tautomer jedinjenja predstavljeno formulom (I): u kojoj veza a je dvostruka veza, a veza b je jednostruka veza ili veza a je jednostruka veza, a veza b je dvostruka veza; X je O ili NR1 kada je veza a jednostruka veza; ili X je N kada je veza a dvostruka veza; R1 je H, (C1-6)alkil, (C1-6)haloalkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- ili Het-(C1-6) alkil-; gde svaki od (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- i Het-(C1-6)alkil- je opciono supstituisan sa -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil ili -N((C1-6)alkil)2; R2 je H, (C1-6)alkil ili -O(C1-6)alkil kada je veza b jednostruka veza; ili R2 je O kada je veza b dvostruka veza; R3 je (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil-, Het-(C1-6)alkil- ili -Y- R31, a veza c je jednostruka veza; ili R3 je (C1-6)alkiliden, a veza c je dvostruka veza; gde Y je O ili S, a R31 je (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7) cikloalkil, aril, (C3-7)cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil- ili Het-(C1-6)alkil-; gde svaki od (C1-6)alkiliden, (C1-6)alkil, (C1-6)haloalkil, (C2-6)alkenil, (C2-6)alkinil, (C3-7) cikloalkil-(C1-6)alkil-, aril-(C1-6)alkil-, Het-(C1-6)alkil- i -Y-R31 je opciono supstituisan sa 1 do 3 supstituenta, svaki nezavisno odabran od (C1-6)alkil, halo, cijano, okso i -O(C1-6)alkil; R4 je aril ili Het, gde svaka aril i Het je opciono supstituisan sa 1 do 5 susptituenata, svaki nezavisno odabran od halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7) cikloalki, -OH, -O(C1-6)alkil-, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i -N((C1-6)alkil)2; gde je (C1-6)alkil opciono supstituisan sa hidroksi, cijano ili okso; R6 i R7 su svaki nezavisno odabrani od H, halo, (C1-6)alkil i (C1-6)haloalkil; pod uslovom da kada veza a je jednostruka veza i veza b je dvostruka veza; i X je NR1; R1 je H; i R2 je O; i R4 je ne supstituisani fenil; R6 je Cl; R7 je H; i veza c je dvostruka veza; onda R3 nije =CH-CH(CH3)2; i gde Het je 4- do 7-člani zasićeni, nezasićeni ili aromatični heterocikl koji ima 1 do 4 heteroatoma, svaki nezavisno odabran od O, N i S, ili 7- do 14-člani zasićeni, nezasićeni ili aromatični heteropolicikl koji gde god je moguće ima 1 do 5 heteroatoma, svaki nezavisno odabran od O, N i S; ili njegova so ili estar.
2.Jedinjenje prema zahtevu 1, gde R4 je naftil ili fenil, gde je fenil opciono supstituisan sa 1 do 3 supstituenta, svaki odabran od halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7) cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i -N((C1-4)alkil)2; gde je (C1-4)alkil opciono supstituisan sa hidroksi, cijano ili okso.
3.Jedinjenje prema zahtevu 1, gde R4 je Het opciono supstituisan sa 1 do 5 supstituenata, svaki nezavisno odabran od halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i -N((C1-6)alkil)2; gde je (C1-6)alkil opciono supstituisan sa hidroksi, cijano ili okso.
4.Jedinjenje prema zahtevu 1, formule (Ia): u kojoj X je O ili NR1; R1 je H, (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil-, ili Het-(C1-6)alkil-; gde Het je 4- do 7-člani heterocikl koji ima 1 do 3 heteroatoma, svaki nezavisno odabran od N, O i S; i gde svaki od (C1-6)alkil, (C3-7)cikloalkil-(C1-6)alkil-, i Het-(C1-6)alkil- je opciono supstituisan sa -OH, -O(C1-3)alkil, -NH2, -NH(C1-3)alkil ili -N((C1-3)alkil)2; R2 je O; R3 je (C1-6)alkil ili (C2-6)alkenil; a veza c je jednostruka veza; R4 je naftil ili fenil, gde je fenil opciono supstituisan sa 1 do 3 supstituenta, svaki nezavisno odabran od halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i -N((C1-4)alkil)2; gde je (C1-4) alkil opciono supstituisan sa hidroksi, cijano ili okso; R6 je H, halo, (C1-3)alkil ili (C1-3)haloalkil; R7 je H ili F; ili njegova so ili estar.
5.Jedinjenje prema zahtevu 4, gde R4 je fenil opciono supstituisan sa 1 do 3 supstituenta svaki nezavisno odabran od halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i -N((C1-4)alkil)2; gde je (C1-4)alkil opciono supstituisan sa hidroksi, cijano ili okso.
6.Jedinjenje prema jednom ili više zahteva 1 do 5, gde R6 je H, Cl ili Br, a R7 je H.
7.Jedinjenje prema zahtevu 1, formule (Id): u kojoj R2 is (C1-6)alkil ili -O(C1-6)alkil; R3 je (C1-6)alkil, (C2-6)alkenil, -O-(C1-6)alkil, -O-(C1-6)haloalkil, -O-(C2-6)alkenil, -O-(C2-6) alkinil, -O-(C3-7)cikloalkil, -O-aril, (C3-7)cikloalkil-(C1-6)alkil-O-, aril-(C1-6)alkil-O- ili Het-(C1-6)alkil-O-; gde svaki od -O-(C1-6)alkil, -O-(C2-6)alkenil, -O-(C2-6)alkinil, -O-(C3-7)cikloalkil, -O-aril, (C3-7)cikloalkil-(C1-6)alkil-O-, aril-(C1-6)alkil-O- i Het-(C1-6)alkil-O- je opciono supstituisan sa 1 do 3 supstituenta svaki nezavisno odabran od (C1-6)alkil, halo, cijano, okso i -O(C1-6)alkil; a veza c je jednostruka veza; ili R3 je (C1-6)alkiliden, a veza c je dvostruka veza; R4 je naftil ili fenil, gde je fenil opciono supstituisan sa 1 do 3 supstituenta svaki nezavisno odabran od halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i -N((C1-4)alkil)2; gde je (C1-4) alkil opciono supstituisan sa hidroksi, cijano ili okso; ili R4 je Het opciono supstituisan sa 1 do 5 supstituenata svaki nezavisno odabran od halo, (C1-6)alkil, (C2-6)alkenil, (C1-6)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-6)alkil, -SH, -S(C1-6)alkil, -NH2, -NH(C1-6)alkil i -N((C1-6)alkil)2; gde je (C1-6)alkil opciono supstituisan sa hidroksi, cijano ili okso; R6 je H, halo, (C1-3)alkil ili (C1-3)haloalkil; i R7 je H ili F; ili njegova so ili estar.
8.Jedinjenje prema zahtevu 7, gde R4 je fenil opciono supstituisan sa 1 do 3 supstituenta, svaki nezavisno odabran od halo, (C1-4)alkil, (C2-4)alkenil, (C1-4)haloalkil, (C3-7)cikloalkil, -OH, -O(C1-4)alkil, -SH, -S(C1-4)alkil, -NH2, -NH(C1-4)alkil i -N((C1-4)alkil)2; gde je (C1-4)alkil opciono supstituisan sa hidroksi, cijano ili okso.
9.Jedinjenje prema zahtevu 7, gde R4 je Het opciono supstituisan sa 1 do 3 supstituenta svaki nezavisno odabran od halo, (C1-6)alkil i -O(C1-6)alkil; gde Het je 5- ili 6-člani heterocikl koji ima 1 do 3 heteroatoma, svaki nezavisno odabran od N, O i S; ili Het je 9- ili 10-člani heteropolicikl koji ima 1 do 3 heteroatoma, svaki nezavisno odabran od N, O i S.
10.Jedinjenje prema zahtevu 1, formule u kojoj R2, R3, R4, R6 i R7 su definisani prema sledećoj tabeli: Jed. R2 R3 R4 R6 R7 1001 CH3 Br H 1002 CH3 Br H 1003 CH3 Br H 1004 CH3 Br H 1005 CH3 Cl H 1006 CH3 Br H 1007 CH3 Br H 1008 CH3 Cl H Jed. R2 R3 R4 R6 R7 1009 -OCH3 Br H 1010 -CH(CH3)2 Br H 1011 CH3 H H 1012 CH3 Cl H 1013 CH3 Cl H 1014 CH3 Cl H 1015 CH3 Cl H 1016 CH3 Cl H Jed. R2 R3 R4 R6 R7 1017 CH3 Cl H 1018 CH3 Cl H 1019 CH3 Cl H 1020 CH3 Br H 1021 CH3 Cl H 1022 CH3 Br H 1023 CH3 Br H Jed. R2 R3 R4 R6 R7 1024 CH3 Cl H 1025 CH3 Br H 1026 CH3 Br H 1027 CH3 Br H 1028 CH3 Br H 1029 CH3 Cl H 1030 CH3 Cl H 1031 CH3 Cl H Jed. R2 R3 R4 R6 R7 1032 CH3 Br H 1033 CH3 H H 1034 CH3 Cl H 1035 CH3 Br H 1036 CH3 Cl H 1037 CH3 Cl H 1038 CH3 Br H 1039 CH3 Br H Jed. R2 R3 R4 R6 R7 1040 CH3 Br H 1041 CH3 Br H 1042 CH3 Br H 1043 CH3 Br H 1044 CH3 Br H 1045 CH3 Br H 1046 CH3 Br H Jed. R2 R3 R4 R6 R7 1047 CH3 Br H 1048 CH3 Br H 1049 CH3 Br H 1050 CH3 Br H 1051 CH3 Br H 1052 CH3 Br H 1053 CH3 F F 1054 CH3 Cl H Jed. R2 R3 R4 R6 R7 1055 CH3 Br H 1056 CH3 Cl H 1057 CH3 Cl H 1058 CH3 Cl H 1059 CH3 Cl H 1060 CH3 Cl H 1061 CH3 Cl H 1062 CH3 Cl H Jed. R2 R3 R4 R6 R7 1063 CH3 Cl H 1064 CH3 Cl H 1065 CH3 Cl H 1066 CH3 Cl H 1067 CH3 Cl H 1068 CH3 Cl H 1069 CH3 Cl H 1070 CH3 Cl H Jed. R2 R3 R4 R6 R7 1071 CH3 Cl H 1072 CH3 Cl H 1073 CH3 Cl H 1074 CH3 Cl H 1075 CH3 Cl H 1076 CH3 Cl H 1077 CH3 Cl H 1078 CH3 Cl H Jed. R2 R3 R4 R6 R7 1079 CH3 Br H 1080 CH3 Cl H 1081 CH3 Cl H 1082 CH3 H H 1083 CH3 Cl H 1084 CH3 Cl H 1085 CH3 Cl H 1086 CH3 Cl H Jed. R2 R3 R4 R6 R7 1087 CH3 Cl H 1088 CH3 Cl H 1089 CH3 Cl H 1090 CH3 Cl H 1091 CH3 Cl H 1092 CH3 Cl H 1093 CH3 Cl H 1094 CH3 Cl H Jed. R2 R3 R4 R6 R7 1095 CH3 Cl H 1096 CH3 Cl H 1097 CH3 Cl H 1098 CH3 Cl H 1099 CH3 Cl H 1100 CH3 Cl H 1101 -CH2CH3 Cl H 1102 CH3 Cl H Jed. R2 R3 R4 R6 R7 1103 CH3 Cl H 1104 CH3 Cl H 1105 CH3 Cl H 1106 CH3 Br H 1107 CH3 Cl H 1108 CH3 Cl H 1109 CH3 Cl H 1110 CH3 Cl H Jed. R2 R3 R4 R6 R7 1111 CH3 Cl H 1112 CH3 Cl H 1113 CH3 Cl H 1114 CH3 Cl H 1115 CH3 Cl H 1116 CH3 Cl H 1117 CH3 Cl H 1118 CH3 Cl H 1119 CH3 Cl H Jed. R2 R3 R4 R6 R7 1120 CH3 Cl H 1121 CH3 Cl H 1122 CH3 Cl H 1123 CH3 Cl H 1124 CH3 Cl H 1125 CH3 Cl H 1126 CH3 Cl H 1127 CH3 Cl H Jed. R2 R3 R4 R6 R7 1128 CH3 Cl H 1129 CH3 Cl H 1130 CH3 Cl H 1131 CH3 Cl H 1132 CH3 Cl H 1133 CH3 Cl H 1134 CH3 Cl H 1135 CH3 Cl H Jed. R2 R3 R4 R6 R7 1136 CH3 Cl H 1137 CH3 Cl H 1138 CH3 Cl H 1139 CH3 Cl H 1140 CH3 Cl H 1141 CH3 Cl H 1142 CH3 Cl H 1143 CH3 Cl H Jed. R2 R3 R4 R6 R7 1144 CH3 Cl H 1145 CH3 Cl H 1146 CH3 Cl H 1147 CH3 Cl H 1148 CH3 Cl H 1149 CH3 Cl H 1150 CH3 Cl H 1151 CH3 Cl H Jed. R2 R3 R4 R6 R7 1152 CH3 H H 1153 CH3 Cl H 1154 CH3 Cl H 1155 CH3 Cl H 1156 CH3 Cl H 1157 CH3 H H 1158 CH3 H H 1159 CH3 H H Jed. R2 R3 R4 R6 R7 1160 CH3 H H 1161 CH3 H H 1162 CH3 Cl H 1163 CH3 H H 1164 CH3 Br H 1165 CH3 Cl H 1166 CH3 Cl H
11.Jedinjenje prema zahtevu 1, formule u kojoj R1, R3, R4 i R6 su definisani prema sledećoj tabeli: Jed. R1 R3 R4 R6 2001 H Cl 2002 Cl 2003 Cl 2004 H Br 2005 H H 2006 H Br Jed. R1 R3 R4 R6 2007 Cl 2008 Cl 2009 CH3 Cl 2010 Cl 2011 Cl
12.Jedinjenje prema zahtevu 1, formule u kojoj R3, R4 i R6 su definisani prema sledećoj tabeli: Jed R3 R4 R6 3001 Br 3002 Br 3003 Br 3004 Br
13.Farmaceutska kompozicija koja sadrži terapeutsku efikasnu količinu jedinjenja formule (I) prema zahtevu 1, ili njegovu farmaceutski prihvatljivu so ili estar, i jedan ili više farmaceutski prihvatljivih nosača.
14.Farmaceutska kompozicija prema zahtevu 13, dodatno sadrži bar jedan drugi antivirusni agens.
15. Primena jedinjenja formule (I) prema zahtevu 1, ili njegove farmaceutski prihvatljive soli ili estra, za proizvodnju medikamenta za lečenje HIV infekcije kod sisara koji imaju ili kod kojih postoji rizik od infekcije.
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