Anti-viral compounds
AssigneesAligos Therapeutics, Inc., Katholieke Universiteit Leuven
InventorsDorothée Alice Marie-Eve Bardiot, Sandro Boland, Arnaud Didier Marie Marchand, Koen Vandyck, David McGowan, Leonid Beigelman
Life of this patent
Estimating the term…
Abstract
Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
Claims41
A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:
- wherein:
- RN is hydrogen, deuterium or an unsubstituted or a substituted C1-6 alkyl;
- Ring A1 is an unsubstituted or a substituted
- an unsubstituted or a substituted
- an unsubstituted or a substituted
- an unsubstituted or a substituted
- or an unsubstituted or a substituted
- wherein the N is the nitrogen of Ring A1 shown in Formula (I) and the carbon indicated with an asterisk is the carbon to which R4 is connected;
- Ring A2 and Ring A4 are an unsubstituted or a substituted 3- to 10-membered ring system that optionally includes 1 to 3 heteroatoms selected from the group consisting of O, S and N, and wherein Ring A2 and Ring A4 are optionally substituted with one or more moieties independently selected from the group consisting of ═O, ═CH2, deuterium, halogen, hydroxy, an unsubstituted C1-4 alkyl, an unsubstituted C1-4 haloalkyl, an unsubstituted C2-4 alkenyl and an unsubstituted or a substituted C3-6 monocyclic cycloalkyl;
- Ring A3 and Ring A5 are an unsubstituted or a substituted monocyclic C3-6 cycloalkyl;
- R1 is selected from the group consisting of cyano, an unsubstituted or a substituted C2-5 alkynyl, an unsubstituted or a substituted acyl, an unsubstituted or a substituted ketoamide, —CH(OH)—(S(═O)2—OH), —CH(OH)—(S(═O)2—O—), —CH(OH)((P═O)(OR6)2) and —C(═O)CH2—O—((P═O)(OR7)2);
- each R6 and each R7 are independently hydrogen, an unsubstituted C1-6 alkyl, an unsubstituted C2-6 alkenyl, an unsubstituted C1-6 haloalkyl, an unsubstituted or a substituted aryl or an unsubstituted or a substituted aryl(C1-4 alkyl);
- R2 is hydrogen, deuterium, halogen or an unsubstituted C1-4 alkyl;
- and
- R3 is an unsubstituted or a substituted monocyclic nitrogen-containing heteroaryl, an unsubstituted or a substituted bicyclic nitrogen-containing heteroaryl, an unsubstituted or a substituted bicyclic nitrogen-containing heterocyclyl or an unsubstituted or a substituted naphthyl;
- or
- R2 and R3 are taken together along with the carbon to which they are attached to form an unsubstituted or a substituted bicyclic, nitrogen-containing heterocyclyl;
- R4 is hydrogen, deuterium or halogen;
- R5 is
- or R12;
- Z1 is —C(═O)— or —S(═O)2—;
- R8 and R10 are independently selected from the group consisting of an unsubstituted or a substituted C1-6 alkyl, an unsubstituted or a substituted C2-6 alkenyl, an unsubstituted or a substituted C2-6 alkynyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted or a substituted bicyclic C5-8 cycloalkyl, an unsubstituted or a substituted monocyclic 4- to 6-membered heterocyclyl and an unsubstituted monocyclic C3-6 cycloalkyl(CH2)—,
- wherein when the C1-6 alkyl is substituted, the C1-6 alkyl is substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, cyano, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted C1-4 alkoxy and an unsubstituted C1-4 haloalkoxy, or the C1-6 alkyl is substituted 1 to 13 times with deuterium;
- wherein when the C2-6 alkenyl, the C2-6 alkynyl, the monocyclic C3-6 cycloalkyl, the bicyclic C5-8 cycloalkyl and the monocyclic 4- to 6-membered heterocyclyl are substituted, the C2-6 alkenyl, the C2-6 alkynyl, the monocyclic C3-6 cycloalkyl, the bicyclic C5-8 cycloalkyl and the monocyclic 4- to 6-membered heterocyclyl are substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, an unsubstituted C2-4 alkenyl, an unsubstituted C2-4 alkynyl, an unsubstituted C1-4 haloalkyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl and an unsubstituted C1-4 alkoxy;
- and
- R9 is selected from the group consisting of an unsubstituted or a substituted C1-6 alkyl, an unsubstituted or a substituted C1-6 haloalkyl, an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, an unsubstituted or a substituted bicyclic C5-6 cycloalkyl, an unsubstituted or a substituted monocyclic heteroaryl, an unsubstituted or a substituted monocyclic heterocyclyl, an unsubstituted or a substituted alkoxy and —NR17R18, wherein the substituted C1-6 alkyl is substituted 1 or 2 times with an unsubstituted C1-4 alkoxy, wherein the substituted monocyclic C3-6 cycloalkyl is substituted 1, 2, 3 or 4 times with a substituent independently selected from the group consisting of halogen, an unsubstituted C1-4 alkyl, an unsubstituted C2-4 alkenyl, an unsubstituted C1-4 alkoxy, an unsubstituted C1-4 haloalkyl and an unsubstituted monocyclic C3-6 cycloalkyl, and wherein the substituted C1-6 haloalkyl is substituted 1 or 2 times with an unsubstituted C1-4 alkoxy;
- R11 is an unsubstituted or a substituted monocyclic 4- to 6-membered heterocyclyl, —(NH)m-(an unsubstituted or a substituted 5- to 6-membered monocyclic heteroaryl), —O-(an unsubstituted or a substituted C1-6 alkyl), —O-(an unsubstituted or a substituted C3-8 cycloalkyl) or —O—(C1-4 alkyl)-(an unsubstituted or a substituted C3-8 cycloalkyl), wherein m is 0 or 1;
- R12 is an unsubstituted or a substituted C1-8 alkyl, an unsubstituted or a substituted C2-8 alkenyl, an unsubstituted or a substituted C2-8 alkynyl, an unsubstituted or a substituted C3-8 cycloalkyl, an unsubstituted or a substituted aryl, an unsubstituted or a substituted heteroaryl, an unsubstituted or a substituted 3- to 8-membered monocyclic heterocyclyl, an unsubstituted or a substituted aryl(alkyl), an unsubstituted or a substituted heteroaryl(alkyl), an unsubstituted or a substituted heterocyclyl(alkyl), an unsubstituted or a substituted C-carboxy, —OR13, —NR14R15 or —C(═O)—NR16AR16B;
- R13 is an unsubstituted or a substituted C1-8 alkyl, an unsubstituted or a substituted C2-8 alkenyl, an unsubstituted or a substituted C2-8 alkynyl, an unsubstituted or a substituted C3-8 cycloalkyl, an unsubstituted or a substituted aryl, an unsubstituted or a substituted heteroaryl, an unsubstituted or a substituted 3- to 8-membered monocyclic heterocyclyl, an unsubstituted or a substituted aryl(alkyl) or an unsubstituted or a substituted heteroaryl(alkyl);
- R14 and R15 are independently selected from the group consisting of hydrogen, an unsubstituted or a substituted C1-8 alkyl, an unsubstituted or a substituted C2-8 alkenyl, an unsubstituted or a substituted C2-8 alkynyl, an unsubstituted or a substituted C3-8 cycloalkyl, an unsubstituted or a substituted aryl, an unsubstituted or a substituted heteroaryl, an unsubstituted or a substituted 3- to 8-membered monocyclic heterocyclyl, an unsubstituted or a substituted aryl(alkyl) or an unsubstituted or a substituted heteroaryl(alkyl);
- or
- R14 and R15 are taken together with the nitrogen to which R14 and R15 are attached to form an optionally substituted 3- to 8-membered heterocyclyl;
- R16A is hydrogen or an unsubstituted C1-3 alkyl;
- R16B is an unsubstituted or a substituted aryl, an unsubstituted or a substituted heteroaryl or an unsubstituted or a substituted 3- to 8-membered monocyclic heterocyclyl;
- and
- R17 and R18 are independently selected from the group consisting of hydrogen, an unsubstituted or a substituted C1-8 alkyl, an unsubstituted or a substituted C2-8 alkenyl, an unsubstituted or a substituted C2-8 alkynyl, an unsubstituted or a substituted C3-8 cycloalkyl, an unsubstituted or a substituted 3-8 membered heterocyclyl, an unsubstituted or a substituted aryl, an unsubstituted or a substituted heteroaryl, an unsubstituted or a substituted aryl(alkyl) and an unsubstituted or a substituted heteroaryl(alkyl);
- or
- R17 and R18 are taken together along with the nitrogen to which they are connected to form an unsubstituted or a substituted 3-8 membered heterocyclyl;
- and
- provided that when R12 is
- then R2 and R3 cannot be taken together along with the carbon to which they are attached to form an unsubstituted
- and
- provided that Ring A1 cannot be an unsubstituted or a substituted
-5. (canceled)
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Dependencies are inferred from the claim text.