Antiviral agents and uses thereof
AssigneeGriffith University
InventorsMark Von Itzstein, Ibrahim El-Deeb, Patrice Guillon, Larissa Heilig
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Abstract
The present invention relates to a compound of Formula (I), or a pharmaceutically acceptable salt thereof: and to pharmaceutical compositions comprising the compound. In Formula (I), R3 is selected from the group consisting of: wherein rings W, X, Y and Z may relate to various heterocyclic, heteroaryl, cycloalkyl, cycloalkenyl, and/or aryl rings. The present invention also relates to uses of the compounds in treating a disease, disorder or condition caused by viral infection.
Claims21
A compound of formula (I), or a pharmaceutically acceptable salt thereof:
- wherein
- R1 is selected from the group consisting of COOH, or a salt thereof, C(O)NR9R10, and C(O)OR11 wherein R9, R10 and R11 are independently selected from the group consisting of hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted aryl, optionally substituted heteroaryl and optionally substituted heterocyclyl;
- R3 is selected from the group consisting of:
- wherein ring W, together with the carbon atoms to which it is attached, form an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted fused bicyclic heterocyclic ring or an optionally substituted fused bicyclic heteroaryl ring;
- wherein:
- (i) ring Y, together with the carbon atoms to which it is attached, form an optionally substituted monocyclic heterocyclic ring or an optionally substituted monocyclic heteroaryl ring;
- and
- ring Z, together with two ring atoms of ring Y, form an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted monocyclic cycloalkyl ring, an optionally substituted monocyclic cycloalkenyl ring or an optionally substituted monocyclic aryl ring, or may be absent;
- or
- (ii) ring Y, together with the carbon atoms to which it is attached, form an optionally substituted phenyl ring;
- and
- ring Z, together with two ring atoms of ring Y, form an optionally substituted monocyclic heterocyclic ring or an optionally substituted monocyclic heteroaryl ring, wherein said monocyclic heterocyclic or heteroaryl ring comprises at least one N ring atom;
- and
- wherein ring X, together with the carbon atoms to which it is attached, form:
- (a) an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted fused bicyclic heterocyclic ring or an optionally substituted fused bicyclic heteroaryl ring;
- or
- (b) a phenyl ring substituted by a heterocyclic or heteroaryl ring, wherein said phenyl, heterocyclic and/or heteroaryl ring are optionally substituted;
- R4 is selected from the group consisting of sulfonamide, urea and NHC(O)R17 wherein R17 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkenyl, all of which may be optionally substituted;
- and
- R6, R7 and Rs are independently selected from the group consisting of H, OH, protected OH, R19, O-R19, NR18R18′, —C(O)R18, —C(S)R18, —OC(O)R18, —C(O)OR18, —NH(C═O)R18, —C(═O )NR18′, and S(O)nR18, wherein n=0−2 and each R18 and R18′ are independently selected from hydrogen, R19 and optionally substituted C1-C9 alkanoyl;
- wherein each R19 is independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl, wherein any R19 group is optionally substituted;
- wherein the compound of Formula (I) is not:
A compound of formula (I), or a pharmaceutically acceptable salt thereof:
- wherein
- R1 is selected from the group consisting of COOH, or a salt thereof, C(O)NR9R10, and C(O)OR11 wherein R9,R10 and R11 are independently selected from the group consisting of hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted aryl, optionally substituted heterosryl and optionally substituted heterocyclyl;
- R3 is selected from the group consisting of:
- R4 is selected from the group consisting of sulfonamide, urea, and NHC(O)R17 wherein R17 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkenyl, all of which may be optionally substituted;
- and
- R6, R7 and R8 are independently selected from the group consisting of H, OH, protected OH, R19, O—R19, NR18R18′, —C(O)R18, —C(S)R18, —OC(O)R18, —C(O)OR18, —NH(C═O)R18, —C(═O)NR18R18′, and S(O)nR18, wherein n=0−2 and each R18 and R18′ are independently selected from hydrogen, R19 and optionally substituted C1-C9 alkanoyl;
- wherein each R19 is independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl, wherein any R19 group is optionally substituted;
- wherein the compound of Formula (I) is not:
A compound of formula (I), or a pharmaceutically acceptable salt thereof:
- wherein
- R1 is selected from the group consisting of COOH, or a salt thereof, C(O)NR9R10, and C(O)OR11 wherein R9, R10 and R11 are independently selected from the group consisting of hydrogen, optionally substituted C1-C6 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted aryl, optionally substituted heteroaryl and optionally substituted heterocyclyl;
- R3 is selected from the group consisting of:
- wherein ring W, together with the carbon atoms to which it is attached, form an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted fused bicyclic heterocyclic ring or an optionally substituted fused bicyclic heteroaryl ring;
- wherein:
- (i) ring Y, together with the carbon atoms to which it is attached, form an optionally substituted monocyclic heterocyclic ring or an optionally substituted monocyclic heteroaryl ring;
- and
- ring Z, together with two ring atoms of ring Y, form an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted monocyclic cycloalkyl ring, an optionally substituted monocyclic cycloalkenyl ring or an optionally substituted monocyclic aryl ring, or may be absent;
- or
- (ii) ring Y, together with the carbon atoms to which it is attached, form an optionally substituted phenyl ring;
- and
- ring Z, together with two ring atoms of ring Y, form an optionally substituted monocyclic heterocyclic ring or an optionally substituted monocyclic heteroaryl ring, wherein said monocyclic heterocyclic or heteroaryl ring comprises at least one N ring atom;
- and
- wherein ring X, together with the carbon atoms to which it is attached, form:
- (a) an optionally substituted monocyclic heterocyclic ring, an optionally substituted monocyclic heteroaryl ring, an optionally substituted fused bicyclic heterocyclic ring or an optionally substituted fused bicyclic heteroaryl ring;
- or
- (b) a phenyl ring substituted by a heterocyclic or heteroaryl ring, wherein said phenyl, heterocyclic and/or heteroaryl ring are optionally substituted;
- R4 is selected from the group consisting of sulfonamide, urea and NHC(O)R17 wherein R17 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 cycloalkenyl, all of which may be optionally substituted;
- and
- R6, R7 and R8 are independently selected from the group consisting of H, OH, protected OH, R19, O—R19, NR18R18′, —C(O)R18, —C(S)R18, —OC(O)R18, —C(O)OR18, —NH(C═O)R18, —C(═O)NR18R18′, and S(O)nR18, wherein n=0−2 and each R18 and R18′ are independently selected from hydrogen, R19 and optionally substituted C1-C9 alkanoyl;
- wherein each R19 is independently selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl, wherein any R19 group is optionally substituted.
Dependencies are inferred from the claim text.