US 2019/0292165 A1 · BROAD SPECTRUM INHIBITORS OF FILOVIRUSES

Broad spectrum inhibitors of filoviruses

AssigneesMicrobiotix, Inc., Albert Einstein College of Medicine, The Govermnment Of The United States As Represented By The Secretary Of The Army

InventorsTerry L. Bowlin, Donald T. Moir, Kartik Chandran, John M. Dye, John D. Williams, Zachary D. Aron, Jay P. Barbor, Kelly N. Lively, Peter J. Nash, Debra M. Mills, Arnab Basu

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Abstract

The present invention is related to the development of therapeutics and prophylactics for the treatment and/or prevention of filovirus infection in humans and other mammals. A new class of small molecules is disclosed that inhibits the interaction of naturally processed (i.e., proteolytically cleaved) filovirus glycoprotein (GPCL) with its host receptor Niemann-Pick C1 (NPC1) protein and thus block infection of host cells by filoviruses. Also disclosed are methods of using the small molecule inhibitors in the treatment/prevention of filovirus infection.

Claims57

Dependent claims

1-20. (canceled)

A composition for treating or preventing filovirus infection in a mammalian subject, said composition comprising a compound of Formula I:

wherein:
X is hydrogen, C or N;
wherein, if X is other than hydrogen,
X and Y are connected by a double bond to form a 5-membered heteroaromatic ring;
Y is C or N, with the proviso that at least one of X and Y is N;
A is C;
the ring atoms U, V and Z are C or N atoms in one of the following configurations, taken in order UVZ:
CCC, CCN, CNC, CCN, NCN, CNN, or NNN;
R1 is hydrogen, a straight-chain or branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is an aryl ring of 5-7 members wherein said aryl is optionally substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, nitro, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is a heteroaryl, fused aryl ring system or heteroaryl bicyclic ring system of 9-11 members wherein said ring system is optionally substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups, with the proviso that if R1 is an aryl group, it must have at least one substituent;
R2 and R3 are independently selected from straight-chain or branched aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring, wherein the ring has 1-4 carbon substituents and 0-1 substituents on any present ring nitrogen, which are independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, substituted aryl, or substituted or unsubstituted heteroaryl rings, wherein substituted aryl or heteroaryl rings have 1-4 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein, if R1 is other than hydrogen, then R2 and R3 can independently be alkyl;
cycloalkyl;
heterocycloalkyl;
aryl;
heteroaryl;
haloalkyl;
nitro;
halogen;
alkoxy;
alkylthio;
haloalkoxy;
sulfonyl;
sulfinyl;
carboxy;
alkoxycarbonyl;
or aminocarbonyl groups;
R4, R5 and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms, 0-1 oxygen atoms and bearing 0-3 substituents (in addition to the bond between W and the ring carbon in the formula) selected from alkyl, cycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, optionally fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, wherein said 0-3 substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and additionally W can be either a nitrogen or a saturated carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups, which optional substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, which non-hydrogen substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
or,
wherein, if X is hydrogen,
A is C or N;
and where A is C, Y is hydrogen, hydroxyl, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkoxysulfonyl, halogen, nitro, cyano, or NRR′, where R and R′ are independently selected from hydrogen, alkyl, acetyl, sulfonyl, and alkylsulfonyl;
the ring atoms U, V and Z are C or N atoms;
R1 is an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, which R1 aryl or heteroaryl ring or ring system is substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups, with the proviso that if R1 is an aryl group, it must have at least one substituent;
R2 and R3 are independently selected from branched aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring, wherein the ring has 1-4 carbon substituents and 0-1 substituents on any present ring nitrogen, which are independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, substituted aryl, or substituted or unsubstituted heteroaryl rings, wherein substituted aryl or heteroaryl rings have 1-4 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
R4, R5 and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a heterocyclic ring system containing 0-3 degrees of unsaturation and between 5-7 members and containing 1-2 atoms, 0-1 oxygen atoms and bearing 0-3 substituents (in addition to the bond linking W and the ring carbon in the formula) including alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, acetyl, arylcarbonyl, heteroarylcarbonyl, aralkyl, alkoxyalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, optionally fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, wherein said 0-3 substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and additionally W can be either a nitrogen or a saturated carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups, which optional substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, which non-hydrogen substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
or a pharmaceutically acceptable salt thereof.

45 more elements

A composition for treating or preventing filovirus infection in a mammalian subject, said composition comprising a compound of Formula II:

wherein:
X is C or N;
Y is C or N;
and at least one of X and Y is N;
R1 is hydrogen, a straight-chain or branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, each ring substituted with 1-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
R2 and R3 can independently be branched-chain aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 carbon substituents and 0-1 nitrogen substituents which may be independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings;
and wherein, if R1 is other than hydrogen, then R2 and R3 can independently be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5 and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms and bearing 0-3 substituents including alkyl, cycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
and additionally W can be either a nitrogen, a saturated carbon, or an olefinic carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
or alternatively, W may be linked with R4 or R5 to produce fused cyclic structures;
or a pharmaceutically acceptable salt thereof.

13 more elements

A composition for treating or preventing filovirus infection in a mammalian subject, said composition comprising a compound of Formula III:

wherein:
X is C or N;
Y is C or N;
and at least one of X and Y is N;
Ar is
where each R3 can independently be hydrogen, alkyl, haloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
R1 is hydrogen, a straight-chain aliphatic group, a branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
R2 can independently be a branched chain aliphatic group, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl group, aryl, or heteroaryl;
or R1 and R2 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl or heteroaryl rings;
and, additionally, if R1 is straight-chain aliphatic group, branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group, then R2 can be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5 and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms, 0-1 oxygen atoms, and bearing 0-3 substituents including alkyl, cycloalkyl, aryl, heteroaryl haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
and additionally, W can be either a nitrogen, a saturated carbon, or an olefinic carbon that is linked via a chain of 1-4 carbons to a basic nitrogen bearing independently hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
or alternatively, W may be linked with R4 or R5 to produce fused cyclic structures;
or W can be a nitrogen that is part of an aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms that may be unsubstituted or substituted and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, and this group can also include connections through either R4 or R5 to produce fused bicyclic structures;
or a pharmaceutically acceptable salt thereof.

15 more elements

A composition for treating or preventing filovirus infection in a mammalian subject, said composition comprising a compound of Formula IV:

wherein:
X can be carbon or nitrogen and Y can be a carbon or nitrogen, and at least one of X and Y is nitrogen, and wherein X and Y can be independently unsubstituted or substituted with a hydrogen, alkyl, halogen, hydroxy, carbonyl, thiol, amino, alkylamino, alkylthio, alkoxy, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
Ar is
where each R3 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or an aminocarbonyl group;
R1 is a hydrogen, straight-chain aliphatic group, branched chain aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
R2 can independently be a branched chain aliphatic group, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl group, aryl, or heteroaryl;
or R1 and R2 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl or heteroaryl rings;
and additionally, if R1 is a straight-chain aliphatic group, branched chain aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group, then R2 can be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5, and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups.
W can be a nitrogen that is part of an aromatic or non-aromatic heterocyclic ring system of between 5-7 members, containing 1-2 nitrogen atoms, 0-1 oxygen atoms, and bearing 0-3 substituents selected from alkyl, cycloalkyl, aryl, heteroaryl haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
or W can be a nitrogen that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing independently hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
wherein the chain of carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, fused aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, or this group can also include connections through either R4 or R5 to produce non-aromatic fused cyclic ring structures;
or a pharmaceutically acceptable salt thereof.

10 more elements

A composition for treating or preventing filovirus infection in a mammalian subject, said composition comprising a compound of Formula V:

wherein:
A is C or N;
and where A is C, Y is hydrogen, hydroxyl, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkoxysulfonyl, halogen, nitro, cyano, or NRR′, where R and R′ are independently selected from hydrogen, alkyl, acetyl, sulfonyl, and alkylsulfonyl;
Ar is, independently, an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, each ring optionally substituted with 0-3 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
W is a ring nitrogen in a non-aromatic heterocyclic ring of from 5-7 members having 0-1 additional heteroatom selected from N or O or a fused non-aromatic bicyclic ring system of from 6 to 10 members having 0-1 additional heteroatom selected from N or O;
where said heterocyclic ring or said bicyclic ring has 0-3 substituents independently selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, acetyl, arylcarbonyl, heteroarylcarbonyl, aralkyl, alkoxyalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and where a cycloalkyl, heterocycloalkyl, aryl, or heteroaryl substituent may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
or
W is NRR′, where R is hydrogen or alkyl, and R′ is alkyl, alkenyl, aminoalkyl, or aminoalkenyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, which R′ group may optionally be further substituted with up to three substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R1 and R2 are, independently, hydrogen, straight-chain or branched alkyl, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein R2 can independently be Ar as defined above;
R4, R5, and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, cyano, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or a pharmaceutically acceptable salt thereof.

9 more elements

A method of inhibiting filovirus infection in a mammal comprising administering to a mammal in need thereof an effective amount of a composition comprising a compound of Formula I:

wherein:
X is hydrogen, C or N;
wherein, if X is other than hydrogen,
X and Y are connected by a double bond to form a 5-membered heteroaromatic ring;
Y is C or N, with the proviso that at least one of X and Y is N;
A is C;
the ring atoms U, V and Z are C or N atoms in one of the following configurations, taken in order UVZ:
CCC, CCN, CNC, CCN, NCN, CNN, or NNN;
R1 is hydrogen, a straight-chain or branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is an aryl ring of 5-7 members wherein said aryl is optionally substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, nitro, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is a heteroaryl, fused aryl ring system or heteroaryl bicyclic ring system of 9-11 members wherein said ring system is optionally substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups, with the proviso that if R1 is an aryl group, it must have at least one substituent;
R2 and R3 are independently selected from straight-chain or branched aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring, wherein the ring has 1-4 carbon substituents and 0-1 substituents on any present ring nitrogen, which are independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, substituted aryl, or substituted or unsubstituted heteroaryl rings, wherein substituted aryl or heteroaryl rings have 1-4 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein, if R1 is other than hydrogen, then R2 and R3 can independently be alkyl;
cycloalkyl;
heterocycloalkyl;
aryl;
heteroaryl;
haloalkyl;
nitro;
halogen;
alkoxy;
alkylthio;
haloalkoxy;
sulfonyl;
sulfinyl;
carboxy;
alkoxycarbonyl;
or aminocarbonyl groups;
R4, R5 and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms, 0-1 oxygen atoms and bearing 0-3 substituents (in addition to the bond between W and the ring carbon in the formula) selected from alkyl, cycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, optionally fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, wherein said 0-3 substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and additionally W can be either a nitrogen or a saturated carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups, which optional substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, which non-hydrogen substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
or,
wherein, if X is hydrogen,
A is C or N;
and where A is C, Y is hydrogen, hydroxyl, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkoxysulfonyl, halogen, nitro, cyano, or NRR′, where R and R′ are independently selected from hydrogen, alkyl, acetyl, sulfonyl, and alkylsulfonyl;
the ring atoms U, V and Z are C or N atoms;
R1 is an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, which R1 aryl or heteroaryl ring or ring system is substituted with 0-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups, with the proviso that if R1 is an aryl group, it must have at least one substituent;
R2 and R3 are independently selected from branched aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring, wherein the ring has 1-4 carbon substituents and 0-1 substituents on any present ring nitrogen, which are independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, substituted aryl, or substituted or unsubstituted heteroaryl rings, wherein substituted aryl or heteroaryl rings have 1-4 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
R4, R5 and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a heterocyclic ring system containing 0-3 degrees of unsaturation and between 5-7 members and containing 1-2 nitrogen atoms, 0-1 oxygen atoms and bearing 0-3 substituents (in addition to the bond linking W and the ring carbon in the formula) including alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, acetyl, arylcarbonyl, heteroarylcarbonyl, aralkyl, alkoxyalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, optionally fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, wherein said 0-3 substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and additionally W can be either a nitrogen or a saturated carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups, which optional substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, which non-hydrogen substituents may, together with either R4 or R5, form a fused substituted or unsubstituted non-aromatic ring bearing 0-2 substituents selected from alkyl, cycloalkyl, hydroxyl, amino, alkylamino, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl;
or a pharmaceutically acceptable salt thereof.

45 more elements

A method of inhibiting filovirus infection in a mammal comprising administering to a mammal in need thereof an effective amount of a composition comprising a compound according to Formula II:

wherein:
X is C or N;
Y is C or N;
and at least one of X and Y is N;
R1 is hydrogen, a straight-chain or branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or R1 is an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, each ring substituted with 1-5 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
R2 and R3 can independently be branched-chain aliphatic groups, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl groups, aryl, or heteroaryl;
or R2 and R3 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 carbon substituents and 0-1 nitrogen substituents which may be independently selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl rings;
and wherein, if R1 is other than hydrogen, then R2 and R3 can independently be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5 and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms and bearing 0-3 substituents including alkyl, cycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
and additionally W can be either a nitrogen, a saturated carbon, or an olefinic carbon that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing, independently, hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with groups selected from haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
or alternatively, W may be linked with R4 or R5 to produce fused cyclic structures;
or a pharmaceutically acceptable salt thereof.

13 more elements

A method of inhibiting filovirus infection in a mammal comprising administering to a mammal in need thereof an effective amount of a composition comprising a compound according to Formula III:

wherein:
X is C or N;
Y is C or N;
and at least one of X and Y is N;
Ar is
where each R3 can independently be hydrogen, alkyl, haloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
R1 is hydrogen, a straight-chain aliphatic group, a branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
R2 can independently be a branched chain aliphatic group, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl group, aryl, or heteroaryl;
or R1 and R2 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl or heteroaryl rings;
and, additionally, if R1 is straight-chain aliphatic group, branched aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group, then R2 can be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5 and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and
W can be either a nitrogen or a carbon that is part of a non-aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms, 0-1 oxygen atoms, and bearing 0-3 substituents including alkyl, cycloalkyl, aryl, heteroaryl haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
and additionally, W can be either a nitrogen, a saturated carbon, or an olefinic carbon that is linked via a chain of 1-4 carbons to a basic nitrogen bearing independently hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein the chain of 1-4 carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl;
or alternatively, W may be linked with R4 or R5 to produce fused cyclic structures;
or W can be a nitrogen that is part of an aromatic heterocyclic ring system of between 5-7 members and containing 1-2 nitrogen atoms that may be unsubstituted or substituted and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings, and this group can also include connections through either R4 or R5 to produce fused bicyclic structures;
or a pharmaceutically acceptable salt thereof.

15 more elements

A method of inhibiting filovirus infection in a mammal comprising administering to a mammal in need thereof an effective amount of a composition comprising a compound according to Formula IV:

wherein:
X can be carbon or nitrogen and Y can be a carbon or nitrogen, and at least one of X and Y is nitrogen, and wherein X and Y can be independently unsubstituted or substituted with a hydrogen, alkyl, halogen, hydroxy, carbonyl, thiol, amino, alkylamino, alkylthio, alkoxy, aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
Ar is
where each R3 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or an aminocarbonyl group;
R1 is a hydrogen, straight-chain aliphatic group, branched chain aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group;
R2 can independently be a branched chain aliphatic group, cycloalkyl, heterocycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, aminocarbonyl group, aryl, or heteroaryl;
or R1 and R2 can be linked together to form a substituted aliphatic or heterocyclic ring bearing 1-4 substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups and/or additional fused cycloalkyl, heterocycloalkyl, aryl or heteroaryl rings;
and additionally, if R1 is a straight-chain aliphatic group, branched chain aliphatic group, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl group, then R2 can be alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R4, R5, and R6 can independently be hydrogen, alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups.
W can be a nitrogen that is part of an aromatic or non-aromatic heterocyclic ring system of between 5-7 members, containing 1-2 nitrogen atoms, 0-1 oxygen atoms, and bearing 0-3 substituents selected from alkyl, cycloalkyl, aryl, heteroaryl haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
or W can be a nitrogen that is linked via a chain of 1-4 carbon atoms to a basic nitrogen bearing independently hydrogen or aliphatic groups of less than nine carbon atoms that can be optionally substituted with haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
wherein the chain of carbon atoms is a saturated hydrocarbon chain or can be substituted with up to 4 non-hydrogen substituents selected from alkyl, fused cycloalkyl, aryl, fused aryl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl, or this group can also include connections through either R4 or R5 to produce non-aromatic fused cyclic ring structures;
or a pharmaceutically acceptable salt thereof.

10 more elements

A method of inhibiting filovirus infection in a mammal comprising administering to a mammal in need thereof an effective amount of a composition comprising a compound according to Formula V:

wherein:
A is C or N;
and where A is C, Y is hydrogen, hydroxyl, alkyl, alkoxy, haloalkyl, haloalkoxy, haloalkoxysulfonyl, halogen, nitro, cyano, or NRR′, where R and R′ are independently selected from hydrogen, alkyl, acetyl, sulfonyl, and alkylsulfonyl;
Ar is, independently, an aryl or heteroaryl ring of 5-7 members, or a fused aryl or heteroaryl bicyclic ring system of 9-11 members, each ring optionally substituted with 0-3 substituents independently selected from alkyl, alkoxy, hydroxyl, carbonyl, carboxy, halogen, haloalkyl, haloalkoxy, alkylthio, sulfonyl, sulfinyl, alkoxyalkyl, alkoxycarbonyl, or aminocarbonyl groups;
W is a ring nitrogen in a non-aromatic heterocyclic ring of from 5-7 members having 0-1 additional heteroatom selected from N or O or a fused non-aromatic bicyclic ring system of from 6 to 10 members having 0-1 additional heteroatom selected from N or O;
where said heterocyclic ring or said bicyclic ring has 0-3 substituents independently selected from alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, haloalkyl, acetyl, arylcarbonyl, heteroarylcarbonyl, aralkyl, alkoxyalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, or sulfinyl, and where a cycloalkyl, heterocycloalkyl, aryl, or heteroaryl substituent may optionally be fused with one or more aromatic, heteroaromatic, cycloalkyl, or heterocycloalkyl rings;
or
W is NRR′, where R is hydrogen or alkyl, and R′ is alkyl, alkenyl, aminoalkyl, or aminoalkenyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, which R′ group may optionally be further substituted with up to three substituents selected from alkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
R1 and R2 are, independently, hydrogen, straight-chain or branched alkyl, cycloalkyl, haloalkyl, nitro, halogen, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
and wherein R2 can independently be Ar as defined above;
R4, R5, and R6 are independently selected from hydrogen, alkyl, haloalkyl, nitro, halogen, cyano, alkoxy, alkylthio, haloalkoxy, sulfonyl, sulfinyl, carboxy, alkoxycarbonyl, or aminocarbonyl groups;
or a pharmaceutically acceptable salt thereof.

9 more elements

A filovirus inhibitor compound selected from the group consisting of:

1-benzhydryl-6-(4-benzylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-benzylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-but-2-enylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-butylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-butylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-cyclobutylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-cyclohexylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-cyclopentylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-cyclopropylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-decylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-fluoroethylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-fluoroethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-furan-2-ylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-furan-3-ylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-hexylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-hydroxyethylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-hydroxyethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-isopropylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-isopropylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-methoxyethylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-methoxyethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-methylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-ethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-octylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-pentyllpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-phenethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-propylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-pyridine-2-ylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-pyridine-3-ylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-pyridine-4-ylmethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-t-butylhomopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-t-butylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(4-trifluoromethylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(2,3-dihydro-1H-inden-2-yl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(2-cyanoethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(2-fluoroethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(2-methanesulfonylethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(2-methoxyethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(3-hydroxypropyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(3-methanesulfonylaminopropyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(3-methoxypropyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(3-morpholinocarbonylpropyl)piperazin-1-yl]-H-benzo[d]imidazole;
1-benzhydryl-6-[4-(dimethylaminocarbonylmethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(ethoxycarbonylmethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-[4-(pyrrolodinocarbonylmethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-benzhydryl-6-{4-[2-(2-oxoimidazolidin-1-yl)ethyl]piperazin-1-yl}-1H-benzo[d]imidazole;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(piperazin-1-yl)benzene;
1-benzhydryl-6-(piperazin-1-yl)-1H-benzo[d]imidazole;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(homopiperazin-1-yl) benzene;
1-benzhydryl-6-(homopiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-6-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1H-benzo[d]imidazole;
2-(1-benzhydryl-1H-benzo[d]imidazol-6-yl)octahydro-1H-pyrido[1,2-a]pyrazine;
1-benzhydryl-6-(3,4-dimethylpiperazin-1-yl)-1H-benzo[d]imidazole;
3-benzhydryl-5-(piperazin-1-yl)-3H-imidazo[4,5-c]pyridine;
6-(4-methylpiperazin-1-yl)-1-(2-phenylpropan-2-yl)-1H-benzo[d]imidazole 1-(cyclohexyl(phenyl)methyl)-6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-(2,2-dimethyl-1-phenylpropyl)-6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-(2-cyclopropyl-1-phenethyl)-6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole;
1-benzhydryl-5-methyl-6-(4-methylpiperazin-1-yl)-1H-benzo[d]imidazole;
3-((2-nitro-5-(piperazin-1-yl)phenyl)amino)-3-phenylpropanoic acid;
3-((2-nitro-5-(4-methylpiperazin-1-yl)phenyl)amino)-3-phenylpropanoic acid;
ethyl 2-((5-(4-methylpiperazin-1-yl)-2-nitrophenyl)amino)-2-phenylacetate;
ethyl 2-((5-(piperazin-1-yl)-2-nitrophenyl)amino)-2-phenylacetate;
1-benzhydryl-6-[4-(thiophen-2-ylmethyl)piperazin-1-yl]-1H-benzo[d]imidazole;
1-(1-benzhydryl-1H-benzo[d]imidazol-6-yl)-N,N-dimethylpiperidin-4-amine;
1-benzhydryl-7-fluoro-6-[4-methylpiperazin-1-yl]-1H-benzo[d]imidazole;
6-([1,4′-bipiperidin]-1′-yl)-1-benzhydryl-1H-benzo[d]imidazole;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-fluoroethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)benzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-propylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-butylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-but-2-enylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-cyclopropylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-3-cyano-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-cyclobutylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-pentyllpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-cyclopentylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-hexylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-cyclohexylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-octylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-decylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-benzylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-phenethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-pyridine-2-ylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-pyridine-3-ylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-pyridine-4-ylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(2,3-dihydro-1H-inden-2-yl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(ethoxycarbonylmethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(dimethylaminocarbonylmethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(pyrrolodinocarbonylmethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(2-methyoxyethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(2-cyanoethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(2-fluoroethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(2-methanesulfonylethyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-{4-[2-(2-oxoimidazolidin-1-yl)ethyl]piperazin-1-yl}-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(3-hydroxypropyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(3-methoxypropyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(3-morpholinocarbonylpropyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-[4-(3-methanesulfonylaminopropyl)piperazin-1-yl]-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-methylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-isopropylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-butylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-benzylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-methoxyethylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-fluoroethylhomopiperazin-1-yl)-2-nitrobenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-fluoroethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-trifluoromethylbenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-fluoroethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-fluorobenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-fluoroethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-cyanobenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-trifluoromethoxybenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-methanesulfonylbenzene;
1-(benzhydrylamino)-5-(4-methylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-isopropylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-t-butylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-hydroxyethylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-methoxyethylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-trifluoromethylethylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-furan-2-ylmethylpiperazin-1-yl)-2-aminosulfonylbenzene;
1-(benzhydrylamino)-5-(4-furan-3-ylmethylpiperazin-1-yl)-2-aminosulfonylbenzene;
and
1-(benzhydrylamino)-5-(4-t-butylhomopiperazin-1-yl)-2-aminosulfonylbenzene;
and pharmaceutically acceptable salts thereof.

191 more elements

Dependencies are inferred from the claim text.