# US 2010/0168097 A1 · Non-Nucleoside Reverse Transcriptase Inhibitors

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- Number: US 2010/0168097 A1
- Document ID: US20100168097A1
- Status: Published application
- Kind: A1
- Application number: 11/922,672
- Filed: 2006-06-23
- Published: 2010-07-01
- Earliest claimed: 2005-06-28
- Inventors: Scott E. Wolkenberg; Craig W. Lindsley; Zhijian Zhao; Theresa M. Williams
- Web page: https://patentgrep.com/patent/US20100168097A1

## CPC

- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- A61P 31/18: for HIV
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of Formula I: Formula (I); are HIV reverse transcriptase inhibitors, wherein R1, R2, R3, R4 and R5 are defined herein. The compounds of Formula (I) and their pharmaceutically acceptable salts are useful in the inhibition of HIV reverse transcriptase, the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines.

## Claims

### Claim 1

A compound of Formula I, or a pharmaceutically acceptable salt thereof:
wherein:
R1 is:
(1) halogen,
(2) CN,
(3) NO2,
(4) C(O)RA,
(5) C(O)ORA,
(6) C(O)N(RA)RB,
(7) SRA,
(8) S(O)RA,
(9) S(O)2RA,
(10) S(O)2N(RA)RB,
(11) N(RA)RB,
(12) N(RA)S(O)2RB,
(13) N(RA)C(O)RB,
(14) N(RA)C(O)ORB,
(15) N(RA)S(O)2N(RA)RB,
(16) OC(O)N(RA)RB,
(17) N(RA)C(O)N(RA)RB,
(18) C1-6 alkyl,
(19) C1-6 haloalkyl,
(20) C2-6 alkenyl,
(21) C2-6 alkynyl,
(22) OH,
(23) O—C1-6 alkyl,
(24) O—C1-6 haloalkyl,
(25) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, or N(RA)C(O)N(RA)RB,
(26) CycA,
(27) AryA,
(28) HetA,
(29) HetR,
(30) C1-6 alkyl substituted with CycA, AryA, HetA, or HetR,
(31) J-CycA,
(32) J-AryA,
(33) J-HetA, or
(34) J-HetR;
J is:
(1) O,
(2) S,
(3) S(O),
(4) S(O)2,
(5) O—C1-6 alkylene,
(6) S—C1-6 alkylene,
(7) S(O)—C1-6 alkylene,
(8) S(O)2—C1-6 alkylene,
(9) N(RA),
(10) N(RA)—C1-6 alkylene,
(11) C(O),
(12) C(O)—C1-6 alkylene,
(13) C(O)—C1-6 alkylene-O,
(14) C(O)N(RA),
(15) C(O)N(RA)—C1-6 alkylene,
(16) C(O)N(RA)—C1-6 alkylene-C(O)O, or
(17) C(O)N(RA)S(O)2;
CycA is C3-8 cycloalkyl which is optionally substituted with a total of from 1 to 6 substituents, wherein:
(i) from zero to 6 substituents are each independently:
(1) halogen,
(2) CN
(3) C1-6 alkyl,
(4) OH,
(5) O—C1-6 alkyl,
(6) C1-6 haloalkyl, or
(7) O—C1-6 haloalkyl, and
(ii) from zero to 2 substituents are each independently:
(1) CycE,
(2) AryE,
(3) O-AryE,
(4) HetE,
(5) HetF, or
(6) C1-6 alkyl substituted with CycE, AryE, O-AryE, HetE, O-HetE, or HetF;
AryA is aryl which is optionally substituted with a total of from 1 to 6 substituents, wherein:
(i) from zero to 6 substituents are each independently:
(1) C1-6 alkyl,
(2) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, or N(RA)C(O)C(O)N(RA)RB,
(3) O—C1-6 alkyl,
(4) C1-6 haloalkyl,
(5) O—C1-6 haloalkyl,
(6) OH,
(7) halogen,
(8) CN,
(9) NO2,
(10) N(RA)RB,
(11) C(O)N(RA)RB,
(12) C(O)RA,
(13) C(O)—C1-6 haloalkyl,
(14) C(O)ORA,
(15) OC(O)N(RA)RB,
(16) SRA,
(17) S(O)RA,
(18) S(O)2RA,
(19) S(O)2N(RA)RB,
(20) N(RA)S(O)2RB,
(21) N(RA)S(O)2N(RA)RB,
(22) N(RA)C(O)RB,
(23) N(RA)C(O)N(RA)RB,
(24) N(RA)C(O)—C(O)N(RA)RB, or
(25) N(RA)CO2RB, and
(ii) from zero to 2 substituents are each independently:
(1) CycE,
(2) AryE,
(3) O-AryE,
(4) HetE,
(5) HetF, or
(6) C1-6 alkyl substituted with CycE, AryE, O-AryE, HetE, O-HetE, or HetF;
HetA is heteroaryl which is optionally substituted with a total of from 1 to 6 substituents, wherein:
(i) from zero to 6 substituents are each independently:
(1) C1-6 alkyl,
(2) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, or N(RA)C(O)C(O)N(RA)RB,
(3) C1-6 alkyl substituted with from 2 to 4 OH,
(4) O—C1-6 alkyl,
(5) C1-6 haloalkyl,
(6) O—C1-6 haloalkyl,
(7) OH,
(8) oxo,
(9) halogen,
(10) CN,
(11) NO2,
(12) N(RA)RB,
(13) C(O)N(RA)RB,
(14) C(O)RA,
(15) C(O)—C1-6 haloalkyl,
(16) C(O)ORA,
(17) OC(O)N(RA)RB,
(18) SRA,
(19) S(O)RA,
(20) S(O)2RA,
(21) S(O)2N(RA)RB,
(22) N(RA)S(O)2RB,
(23) N(RA)S(O)2N(RA)RB,
(24) N(RA)C(O)RB,
(25) N(RA)C(O)N(RA)RB,
(26) N(RA)C(O)—C(O)N(RA)RB, or
(27) N(RA)CO2RB, and
(ii) from zero to 2 substituents are each independently:
(1) CycE,
(2) AryE,
(3) O-AryE,
(4) HetE,
(5) HetF, or
(6) C1-6 alkyl substituted with CycE, AryE, O-AryE, HetE, O-HetE, or HetF;
HetR is (i) a 4- to 7-membered, saturated or mono-unsaturated heterocyclic ring containing at least one carbon atom and from 1 to 4 heteroatoms independently selected from N, O and S, where each S is optionally oxidized to S(O) or S(O)2 or (ii) a 6- to 10-membered saturated or mono-unsaturated, bridged or fused heterobicyclic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, where each S is optionally oxidized to S(O) or S(O)2; and wherein the saturated or mono-unsaturated heterocyclic or heterobicyclic ring is optionally substituted with a total of from 1 to 4 substituents, wherein:
(i) from zero to 4 substituents are each independently halogen, CN, C1-6 alkyl, OH, oxo, C(O)RA, CO2RA, S(O)RA, SRA, S(O)2RA, O—C1-6 alkyl, C1-6 haloalkyl, C1-6 alkylene-CN, C1-6 alkylene-OH, or C1-6 alkylene-O—C1-6 alkyl; and
(ii) from zero to 2 substituents are each independently CycE, AryE, HetE, HetF, or C1-6 alkyl substituted with CycE, AryE, HetE, or HetF;
R2 is:
(1) C1-6 alkyl,
(2) C1-6 haloalkyl,
(3) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)SO2RB, N(RA)SO2N(RA)RB, OC(O)N(RA)RB, or N(RA)C(O)N(RA)RB,
(3) CycB,
(4) AryB,
(5) HetB,
(6) HetS,
(7) C1-6 alkyl substituted with CycB, AryB, HetB, or HetS,
(8) N(RA)—C1-6 alkyl,
(9) N(RA)—C1-6 alkyl, wherein the alkyl is substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)SO2RB, N(RA)SO2N(RA)RB, OC(O)N(RA)RB, or N(RA)C(O)N(RA)RB, with the proviso that the OH, O—C1-6 alkyl, or O—C1-6 haloalkyl is not attached to the carbon in C1-6 alkyl that is directly attached to the rest of the molecule,
(10) N(RA)-CycB,
(11) N(RA)-AryB,
(12) N(RA)-HetB, or
(13) N(RA)—C1-6 alkyl, wherein the alkyl is substituted with CycB, AryB, HetB, or HetS;
CycB independently has the same definition as CycA;
AryB independently has the same definition as AryA;
HetB independently has the same definition as HetA;
HetS independently has the same definition as HetR;
R3 is HetC, wherein HetC independently has the same definition as HetA;
R4 is H, C1-6 alkyl, C(O)C1-6 alkyl, C(O)-CycD, C(O)-AryD, C(O)-HetD, or C(O)HetU;
CycD independently has the same definition as CycA;
AryD independently has the same definition as AryA;
HetD independently has the same definition as HetA;
HetU independently has the same definition as HetR;
R5 is H or independently has the same definition as R1;
each aryl is independently (i) phenyl, (ii) a 9- or 10-membered bicyclic, fused carbocylic ring system in which at least one ring is aromatic, or (iii) an 11- to 14-membered tricyclic, fused carbocyclic ring system in which at least one ring is aromatic;
each heteroaryl is independently (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, or (ii) a 9- or 10-membered bicyclic, fused ring system containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein either one or both of the rings contain one or more of the heteroatoms, at least one ring is aromatic, each N is optionally in the form of an oxide, and each S in a ring which is not aromatic is optionally S(O) or S(O)2;
each CycE is independently C3-8 cycloalkyl which is optionally substituted with a total of from 1 to 4 substituents, wherein:
(i) from zero to 4 substituents are each independently halogen, C1-6 alkyl, OH, O—C1-6 alkyl, C1-6 haloalkyl, or O—C1-6 haloalkyl, and
(ii) from zero to 2 substituents are each independently CycG, AryG, HetG, HetH, or C1-6 alkyl substituted with CycG, AryG, O-AryG, HetG, or HetH;
each AryE is independently phenyl or naphthyl, wherein the phenyl or naphthyl is optionally substituted with a total of from 1 to 5 substituents, wherein:
(i) from zero to 5 substituents are each independently halogen, CN, NO2, C1-6 alkyl, C1-6 haloalkyl, OH, O—C1-6 alkyl, O—C1-6 haloalkyl, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, or SO2N(RA)C(O)RB, and
(ii) from zero to 2 substituents are each independently CycG, AryG, HetG, HetH, or C1-6 alkyl substituted with CycG, AryG, O-AryG, HetG, or HetH;
each HetE is independently (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, or (ii) a 9- or 10-membered fused heterobicyclic ring selected from 2,3-dihydrobenzo-1,4-dioxinyl and benzo-1,3-dioxolyl; and wherein the heteroaromatic ring or the heterobicyclic ring is optionally substituted with a total of from 1 to 4 substituents wherein:
(i) from zero to 4 substituents are each independently halogen, C1-6 alkyl, C1-6 haloalkyl, O—C1-6 alkyl, O—C1-6 haloalkyl, OH, C(O)RA, CO2RA, SO2RA, N(RA)RB, N(RA)C(O)N(RA)RB, or N(RA)CO2RB, and
(ii) from zero to 2 substituents are each independently CycG, AryG, HetG, HetH, or C1-6 alkyl substituted with CycG, AryG, O-AryG, HetG, or HetH;
each HetF is independently a 4- to 7-membered, saturated or mono-unsaturated heterocyclic ring containing at least one carbon atom and from 1 to 4 heteroatoms independently selected from N, O and S, where each S is optionally oxidized to S(O) or S(O)2, and wherein the saturated or mono-unsaturated heterocyclic ring is optionally substituted with a total of from 1 to 4 substituents, wherein:
(i) from zero to 4 substituents are each independently halogen, CN, C1-6 alkyl, OH, oxo, O—C1-6 alkyl, C1-6 haloalkyl, O—C1-6 haloalkyl, C(O)RA, CO2RA, or SO2RA, and
(ii) from zero to 2 substituents are each independently CycG, AryG, HetG, HetH, or C1-6 alkyl substituted with CycG, AryG, O-AryG, HetG, or HetH;
each CycG is independently C3-8 cycloalkyl which is optionally substituted with from 1 to 4 substituents, each of which is independently halogen, C1-6 alkyl, OH, O—C1-6 alkyl, C1-6 haloalkyl, or O—C1-6 haloalkyl;
each AryG is independently phenyl or naphthyl, wherein the phenyl or naphthyl is optionally substituted with from 1 to 5 substituents each of which is independently halogen, CN, NO2, C1-6 alkyl, C1-6 haloalkyl, OH, O—C1-6 alkyl, O—C1-6 haloalkyl, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, or SO2N(RA)C(O)RB;
each HetG is independently a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is optionally substituted with from 1 to 4 substituents each of which is independently halogen, C1-6 alkyl, C1-6 haloalkyl, O—C1-6 alkyl, O—C1-6 haloalkyl, OH, C(O)RA, CO2RA, SO2RA, N(RA)RB, N(RA)C(O)N(RA)RB, or N(RA)CO2RB;
each HetH is independently a 4- to 7-membered, saturated or mono-unsaturated heterocyclic ring containing at least one carbon atom and from 1 to 4 heteroatoms independently selected from N, O and S, where each S is optionally oxidized to S(O) or S(O)2, and wherein the saturated or mono-unsaturated heterocyclic ring is optionally substituted with from 1 to 4 substituents, each of which is independently halogen, CN, C1-6 alkyl, OH, oxo, O—C1-6 alkyl, C1-6 haloalkyl, O—C1-6 haloalkyl, C(O)RA, CO2RA, or SO2RA;
each RA is independently H or C1-6 alkyl; and
each RB is independently H or C1-6 alkyl;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having to 3 halogen substituents, R4 is H, and R5 is H, then R3 is not (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently amino, C1-4 alkyl, C1-4 alkylamino, halogen, sulfonamido, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents or (ii) 4,5,6,7-hexahydrobenzimidazol-2-yl.

### Claim 2 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is:
(1) halogen,
(2) CN,
(3) NO2,
(4) N(RA)RB,
(5) N(RA)S(O)2RB,
(6) N(RA)C(O)RB,
(7) C1-6 alkyl,
(8) C1-6 haloalkyl,
(9) C2-6 alkenyl,
(10) OH,
(11) O—C1-6 alkyl,
(12) O—C1-6 haloalkyl,
(13) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, S(O)2RA, S(O)2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)S(O)2RB, N(RA)S(O)2N(RA)RB, OC(O)N(RA)RB, or N(RA)C(O)N(RA)RB,
(14) CycA,
(15) AryA,
(16) HetA, or
(17) C1-6 alkyl substituted with CycA, AryA, or HetA; and
R5 is H;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, R4 is H, and R5 is H, then R3 is not (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently amino, C1-4 alkyl, C1-4 alkylamino, halogen, sulfonamido, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents or (ii) 4,5,6,7-hexahydrobenzimidazol-2-yl.

### Claim 3 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is AryB or HetS; and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, R4 is H, and R5 is H, then R3 is not (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently amino, C1-4 alkyl, C1-4 alkylamino, halogen, sulfonamido, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents or (ii) 4,5,6,7-hexahydrobenzimidazol-2-yl.

### Claim 4 (depends on 3)

The compound according to claim 3, or a pharmaceutically acceptable salt thereof, wherein:
AryB is phenyl, wherein the phenyl is optionally substituted with a total of from 1 to 5 substituents, each of which is independently:
(1) C1-4 alkyl,
(2) O—C1-4 alkyl,
(3) C1-4 haloalkyl,
(4) O—C1-4 haloalkyl,
(5) OH,
(6) halogen,
(7) CN,
(8) NO2,
(9) NH2,
(10) N(H)—C1-4 alkyl,
(11) N(C1-4 alkyl)2,
(12) C(O)NH2,
(13) C(O)N(H)—C1-4 alkyl,
(14) C(O)N(C1-4 alkyl)2,
(15) C(O)—C1-4 alkyl,
(16) CO2—C1-4 alkyl,
(17) S—C1-4 alkyl,
(18) S(O)—C1-4 alkyl,
(19) SO2—C1-4 alkyl,
(20) SO2NH2,
(21) SO2N(H)—C1-4 alkyl,
(22) SO2N(C1-4 alkyl)2,
(23) SO2N(H)C(O)—C1-4 alkyl,
(24) SO2N(C1-4 alkyl)C(O)—C1-4 alkyl,
(25) N(H)C(O)—C1-4 alkyl, or
(26) N(C1-4 alkyl)C(O)—C1-4 alkyl; and
HetS is a 4- to 7-membered, saturated or mono-unsaturated heterocyclic ring or a 6- to 10-membered saturated or mono-unsaturated, bridged or fused heterobicyclic ring, wherein the heterocyclic or heterobicyclic ring contains a nitrogen atom which is directly attached to the rest of the molecule and optionally contains an additional heteroatom selected from N, O, and S, where the S is optionally oxidized to S(O) or S(O)2; and wherein the heterocyclic or heterobicyclic ring is optionally substituted with a total of from 1 to 4 substituents, wherein:
(i) from zero to 4 substituents are each independently Cl, Br, F, C1-4 alkyl, OH, oxo, S(O)2—C1-4 alkyl, O—C1-4 alkyl, O—C1-4 haloalkyl, or C1-4 haloalkyl; and
(ii) from zero to 1 substituent is AryE, HetE, CH2-AryE, or CH2-HetE;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, R4 is H, and R5 is H, then R3 is not (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently amino, C1-4 alkyl, C1-4 alkylamino, halogen, sulfonamido, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents or (ii) 4,5,6,7-hexahydrobenzimidazol-2-yl.

### Claim 5 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R3 is HetC; and HetC is:
a 5-membered heteroaromatic ring containing from 1 to 3 heteroatoms independently selected from 1 to 3N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon, and the heteroaromatic ring is optionally substituted with from 1 to 2 substituents each of which is independently
(1) C1-4 alkyl,
(2) C1-4 alkyl substituted with OH or O—C1-4 alkyl,
(3) C1-4 alkyl substituted with from 2 to 4 OH,
(4) O—C1-4 alkyl,
(5) C1-4 haloalkyl,
(6) O—C1-4 haloalkyl,
(7) OH,
(8) Cl, Br, or F,
(9) CN,
(10) C(O)N(H)—C1-4 alkyl,
(11) C(O)N(C1-4 alkyl)2,
(12) S(O)2—C1-4 alkyl,
(13) S(O)2NH2,
(14) S(O)2N(H)—C1-4 alkyl,
(15) S(O)2N(C1-4 alkyl)2,
(16) CycE, AryE, or HetE, or
(17) CH2-CycE, CH2-AryE, CH2—O-AryE, or CH2-HetE, or
(ii) 5-membered heteroaromatic ring containing from 1 to 2 heteroatoms independently selected from 1 to 2 N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon and has fused thereto a benzene ring wherein the benzene ring is optionally substituted with from 1 to 3 substituents each of which is independently
(1) C1-4 alkyl,
(2) O—C1-4 alkyl,
(3) C1-4 haloalkyl,
(4) O—C1-4 haloalkyl,
(5) OH,
(6) Cl, Br, or F,
(7) CN,
(8) C(O)N(H)—C1-4 alkyl,
(9) C(O)N(C1-4 alkyl)2,
(10) S(O)2—C1-4 alkyl,
(11) S(O)2NH2,
(12) S(O)2N(H)—C1-4 alkyl, or
(13) S(O)2N(C1-4 alkyl)2;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, R4 is H, and R5 is H, then R3 is not a 5-membered heteroaromatic ring containing from 1 to 3 heteroatoms independently selected from 1 to 3N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently C1-4 alkyl, Cl, Br, F, S(O)2NH2, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents.

### Claim 6 (depends on 5)

The compound according to claim 5, or a pharmaceutically acceptable salt thereof, wherein:
R3 is
X1 is:
(1) H,
(2) C1-4 alkyl,
(3) C1-4 alkyl substituted with OH or O—C1-4 alkyl,
(4) C1-4 alkyl substituted with from 2 to 4 OH,
(5) C3-6 cycloalkyl which is optionally substituted with C1-4 alkyl or phenyl,
(6) phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently C1-4 alkyl, O—C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 fluoroalkyl OH, Cl, Br, F, CN, NO2, C(O)N(H)—C1-4 alkyl, C(O)N(C1-4 alkyl)2, CO2—C1-4 alkyl, S(O)2—C1-4 alkyl, S(O)2NH2, S(O)2N(H)—C1-4 alkyl, or S(O)2N(C1-4 alkyl)2,
(7) phenyl substituted with a heterocyclic ring selected from the groun consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
(8) CH2-phenyl,
(9) CH2—O-phenyl,
(10) heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, furanyl, thienyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, and pyrazinyl, wherein the heteroaryl is optionally substituted with from 1 to 3 substituents each of which is independently Cl, Br, F, C1-4 alkyl, CF3, OH, O—C1-4 alkyl, or OCF3, or
(11) heteroaryl selected from the group consisting of 2,3-dihydrobenzo-1,4-dioxinyl and benzo-1,3-dioxolyl;
Y1 independently has the same definition as X1; and
Y2 independently has the same definition as X1;
or alternatively, Y1 and Y2 together with the carbon atoms to which each is attached form a benzo ring;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, R4 is H, and R5 is H, then (i) Xl in the definition of R3 is not H, C1-4 alkyl, or C3-5 cycloalkyl and (ii) one of Y1 and Y2 in the definition of R3 is not H, C1-4 alkyl, or C3-5 cycloalkyl when the other of Y1 and Y2 is H, C1-4 alkyl, or C3-5 cycloalkyl.

### Claim 7 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R4 is H;
and with the proviso that:
(A) when R1 is halogen, R2 is AryB and AryB is unsubstituted phenyl or phenyl substituted with from 1 to 5 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, C1-4 alkylamino, sulfonamido, or C1-4 haloalkyl having from 1 to 3 halogen substituents, and R5 is H, then R3 is not (i) a 5- or 6-membered heteroaromatic ring containing from 1 to 4 heteroatoms independently selected from N, O and S, wherein each N is optionally in the form of an oxide, and wherein the heteroaromatic ring is unsubstituted or substituted with one or more substituents each of which is independently amino, C1-4 alkyl, alkylamino, halogen, sulfonamido, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents or (ii) 4,5,6,7-hexahydrobenzimidazol-2-yl.

### Claim 8 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein:
R1 is halogen;
R2 is:
(i) phenyl, wherein the phenyl is optionally substituted with a total of from 1 to 3 substituents, each of which is independently:
(1) C1-4 alkyl,
(2) O—C1-4 alkyl,
(3) C1-4 haloalkyl,
(4) O—C1-4 haloalkyl,
(5) OH,
(6) halogen,
(7) CN,
(8) NO2,
(9) NH2,
(10) N(H)—C1-4 alkyl,
(11) N(C1-4 alkyl)2,
(12) C(O)NH2,
(13) C(O)N(H)—C1-4 alkyl,
(14) C(O)N(C1-4 alkyl)2,
(15) C(O)—C1-4 alkyl,
(16) CO2—C1-4 alkyl,
(17) S—C1-4 alkyl,
(18) S(O)—C1-4 alkyl,
(19) SO2—C1-4 alkyl,
(20) SO2NH2,
(21) SO2N(H)—C1-4 alkyl,
(22) SO2N(C1-4 alkyl)2,
(23) SO2N(H)C(O)—C1-4 alkyl,
(24) SO2N(C1-4 alkyl)C(O)—C1-4 alkyl,
(25) N(H)C(O)—C1-4 alkyl, or
(26) N(C1-4 alkyl)C(O)—C1-4 alkyl, or
(ii) HetS, wherein HetS is a 5- or 6-membered, saturated or mono-unsaturated heterocyclic ring containing a nitrogen atom that is directly attached to the rest of the molecule and optionally containing an additional heteroatom selected from N, O, and S, where the S is optionally oxidized to S(O) or S(O)2; and wherein the heterocyclic ring is optionally substituted with a total of from 1 to 3 substituents, each of which is independently Cl, Br, F, C1-4 alkyl, OH, oxo, S(O)2—C1-4 alkyl, O—C1-4 alkyl, O—C1-4 haloalkyl, or C1-4 haloalkyl;
R3 is:
(i) a 5-membered heteroaromatic ring containing from 1 to 3 heteroatoms independently selected from 1 to 3 N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon, and the heteroaromatic ring is optionally substituted with from 1 to 2 substituents each of which is independently:
(1) C1-4 alkyl,
(2) C1-4 alkyl substituted with OH or O—C1-4 alkyl,
(3) C1-4 alkyl substituted with from 2 to 4 OH,
(4) O—C1-4 alkyl,
(5) C1-4 haloalkyl,
(6) O—C1-4 haloalkyl,
(7) OH,
(8) Cl, Br, or F,
(9) CN,
(10) C(O)N(H)—C1-4 alkyl,
(11) C(O)N(C1-4 alkyl)2,
(12) S(O)2—C1-4 alkyl,
(13) S(O)2NH2,
(14) S(O)2N(H)—C1-4 alkyl,
(15) S(O)2N(C1-4 alkyl)2,
(16) CycE, AryE, or HetE, or
(17) CH2-CycE, CH2-AryE, CH2—O-AryE, or CH2-HetE, or
(ii) 5-membered heteroaromatic ring containing from 1 to 2 heteroatoms independently selected from 1 to 2N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon and has fused thereto a benzene ring wherein the benzene ring is optionally substituted with from 1 to 3 substituents each of which is independently
(1) C1-4 alkyl,
(2) O—C1-4 alkyl,
(3) C1-4 haloalkyl,
(4) O—C1-4 haloalkyl,
(5) OH,
(6) Cl, Br, or F,
(7) CN,
(8) C(O)N(H)—C1-4 alkyl,
(9) C(O)N(C1-4 alkyl)2;
(10) S(O)2—C1-4 alkyl,
(11) S(O)2NH2;
(12) S(O)2N(H)—C1-4 alkyl, or
(13) S(O)2N(C1-4 alkyl)2;
each CycE is independently C3-6 cycloalkyl which is optionally substituted with a total of from 1 to 3 substituents, wherein:
(i) from zero to 3 substituents are each independently C1-4 alkyl, OH, or O—C1-4 alkyl, and
(ii) from zero to 1 substituent is phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently C1-4 alkyl, O—C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 fluoroalkyl, OH, Cl, Br, F, CN, C(O)N(H)—C1-4 alkyl, C(O)N(C1-4 alkyl)2, CO2—C1-4 alkyl, S(O)2—C1-4 alkyl, S(O)2NH2, S(O)2N(H)—C1-4 alkyl, or S(O)2N(C1-4 alkyl)2;
each AryE is independently phenyl, which is optionally substituted with a total of from 1 to 3 substituents, wherein:
(i) from zero to 3 substituents are each independently C1-4 alkyl, O—C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 fluoroalkyl, OH, Cl, Br, F, CN, NO2, C(O)N(H)—C1-4 alkyl, C(O)N(C1-4 alkyl)2, CO2—C1-4 alkyl, S(O)2—C1-4 alkyl, S(O)2NH2, S(O)2N(H)—C1-4 alkyl, or S(O)2N(C1-4 alkyl)2, and
(ii) from zero to 1 substituent is a 4- to 7-membered saturated or mono-unsaturated heterocyclic ring containing from 1 to 2 heteroatoms selected from 1 to 2N atoms, zero to 1 O atom, and zero to 1 S atom, where the S is optionally oxidized to S(O) or S(O)2, and wherein the saturated or mono-unsaturated heterocyclic ring is optionally substituted with from 1 to 3 substituents, each of which is independently C1-4 alkyl, OH, oxo, O—C1-4 alkyl, C(O)—C1-4 alkyl, C(O)O—C1-4 alkyl, or SO2—C1-4 alkyl;
each HetE is independently (i) a 5- or 6-membered heteroaromatic ring selected from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furanyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl, and pyrazinyl or (ii) a 9- or 10-membered fused heterobicyclic ring selected from 2,3-dihydrobenzo-1,4-dioxinyl and benzo-1,3-dioxolyl; and wherein the heteroaromatic ring or the heterobicyclic ring is optionally substituted with a total of from 1 to 3 substituents each of which is independently halogen, C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 alkyl, O—C1-4 fluoroalkyl, or OH;
R4 is H; and
R5 is H;
and with the proviso that:
(A) when R2 is unsubstituted phenyl or phenyl substituted with from 1 to 3 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, SO2NH2, or C1-4 haloalkyl having from 1 to 3 halogen substituents, then R3 is not a 5-membered heteroaromatic ring containing from 1 to 3 heteroatoms selected from 1 to 3 N atoms, from zero to 1 O atom, and from zero to 1 S atom, wherein the heteroaromatic ring is connected to the rest of the molecule via a ring carbon, and the heteroaromatic ring is unsubstituted or substituted with from 1 to 2 substituents each of which is independently C1-4 alkyl, Cl, Br, F, SO2NH2, CN, C3-5 cycloalkyl, or C1-4 haloalkyl having from 1 to 3 halogen substituents.

### Claim 9 (depends on 8)

The compound according to claim 8, or a pharmaceutically acceptable salt thereof, wherein:
R3 is
X1 is:
(1) H,
(2) C1-4 alkyl,
(3) C1-4 alkyl substituted with OH or O—C1-4 alkyl,
(4) C1-4 alkyl substituted with from 2 to 4 OH,
(5) C3-6 cycloalkyl which is optionally substituted with C1-4 alkyl or phenyl,
(6) phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently C1-4 alkyl, O—C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 fluoroalkyl, OH, Cl, Br, F, CN, NO2, C(O)N(H)—C1-4 alkyl, C(O)N(C1-4 alkyl)2, CO2—C1-4 alkyl, S(O)2—C1-4 alkyl, S(O)2NH2, S(O)2N(H)—C1-4 alkyl, or S(O)2N(C1-4 alkyl)2,
(7) phenyl substituted with a heterocyclic ring selected from the grout) consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
(8) CH2-phenyl,
(9) CH2—O-phenyl,
(10) heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, furanyl, thienyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, and pyrazinyl, wherein the heteroaryl is optionally substituted with from 1 to 3 substituents each of which is independently Cl, Br, F, C1-4 alkyl, CF3, OH, O—C1-4 alkyl, or OCF3, or
(11) heteroaryl selected from the group consisting of 2,3-dihydrobenzo-1,4-dioxinyl and benzo-1,3-dioxolyl;
Y1 independently has the same definition as X1; and
Y2 independently has the same definition as X1;
or alternatively, Y1 and Y2 together with the carbon atoms to which each is attached form a benzo ring;
and with the proviso that:
(A) when R2 is unsubstituted phenyl or phenyl substituted with from 1 to 3 substituents each of which is independently halogen, NO2, CN, C1-4 alkyl, O—C1-4 alkyl, SO2NH2, or C1-4 haloalkyl having from 1 to 3 halogen substituents, then X1 in the definition of R3 is not H, C1-4 alkyl, or C3-5 cycloalkyl, and one of Y1 and Y2 in the definition of R3 is not H, C1-4 alkyl, or C3-5 cycloalkyl when the other of Y1 and Y2 is H, C1-4 alkyl, or C3-5 cycloalkyl.

### Claim 10 (depends on 9)

The compound according to claim 9, or a pharmaceutically acceptable salt thereof, wherein:
R1 is Cl or Br;
R2 is:
(i) phenyl, which is optionally substituted with a total of from 1 to 3 substituents, each of which is independently CH3, OCH3, CF3, OCF3, OH, Cl, Br, F, CN, C(O)N(CH3)2, C(O)CH3, CO2CH3, or SO2CH3, or
(ii) a cathrated heterocyclic ring selected from the groun consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
R3 is
X1 is:
(1) H,
(2) C1-3 alkyl,
(3) C1-3 alkyl substituted with OH or OCH3,
(4) C1-4 alkyl substituted with from 2 to 4 OH,
(5) C3-6 cycloalkyl which is optionally substituted with C1-4 alkyl or phenyl,
(6) phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently CH3, OCH3, CF3, OCF3, OH, Cl, Br, F, CN, NO2, C(O)N(H)CH3, C(O)N(CH3)2, CO2CH3, or S(O)2CH3,
(7) phenyl substituted with a saturated heterocyclic ring selected from the group consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
(8) CH2-phenyl,
(9) CH2—O-phenyl,
(10) thienyl or pyridinyl, or
(11) benzo-1,3-dioxolyl;
one of Y1 and Y2 independently has the same definition as X 1 , and the other of Y1 and Y2 is H;
or alternatively, Y1 and Y2 together with the carbon atoms to which each is attached form a benzo ring;
and with the proviso that:
(A) when R2 is unsubstituted phenyl or phenyl substituted with from 1 to 3 substituents each of which is independently CH3, OCH3, CF3, , Cl, Br, F, or CN, then (i) X1 in the definition of R3 is not H, C1-3 alkyl, or C3-5 cycloalkyl and (ii) one of Y1 and Y2 in the definition of R3 is not H, C1-4 alkyl, or C3-5 cycloalkyl when the other of Y1 and Y2 is H.

### Claim 11 (depends on 10)

The compound according to claim 10, or a pharmaceutically acceptable salt thereof, wherein:
R2 is phenyl and R3 is
R2 is
and R3 is
and with the proviso that:
(A) when R2 is unsubstituted phenyl, then X1 in the definition of R3 is not H, C1-3 alkyl, or C3-5 cycloalkyl, and one of Y1 and Y2 in the definition of R3 is (i) not H, C1-3 alkyl, or C3-5 cycloalkyl when the other of Y1 and Y2 is H.

### Claim 12 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein:
R1 is halogen;
R2 is:
(1) C1-6 alkyl,
(2) C3-6 cycloalkyl, or
(3) C1-6 alkyl substituted with C3-6 cycloalkyl;
R3 is
X1 is:
(1) H,
(2) C1-4 alkyl,
(3) C1-4 alkyl substituted with OH or O—C1-4 alkyl,
(4) C1-4 alkyl substituted with from 2 to 4 OH,
(5) C3-6 cycloalkyl which is optionally substituted with C1-4 alkyl or phenyl,
(6) phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently C1-4 alkyl, O—C1-4 alkyl, C1-4 fluoroalkyl, O—C1-4 fluoroalkyl, OH, Cl, Br, F, CN, NO2, C(O)N(H)—C1-4 alkyl, C(O)N(C1-4 alkyl)2, CO2—C1-4 alkyl, S(O)2—C1-4 alkyl, S(O)2NH2, S(O)2N(H)—C1-4 alkyl, or S(O)2N(C1-4 alkyl)2,
(7) phenyl substituted with a heterocyclic ring selected from the group consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
(8) CH2-phenyl,
(9) CH2—O-phenyl,
(10) heteroaryl selected from the group consisting of pyrrolyl, imidazolyl, furanyl, thienyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, and pyrazinyl, wherein the heteroaryl is optionally substituted with from 1 to 3 substituents each of which is independently Cl, Br, F, C1-4 alkyl, CF3, OH, O—C1-4 alkyl, or OCF3, or
(11) heteroaryl selected from the group consisting of 2,3-dihydrobenzo-1,4-dioxinyl and benzo-1,3-dioxolyl;
Y1 independently has the same definition as X1; and
Y2 independently has the same definition as X1;
or alternatively, Y1 and Y2 together with the carbon atoms to which each is attached form a benzo ring;
R4 is H; and
R5 is H.

### Claim 13 (depends on 12)

The compound according to claim 12, or a pharmaceutically acceptable salt thereof, wherein:
R1 is Cl or Br;
R2 is:
(1) C1-5 alkyl,
(2) C3-6 cycloalkyl, or
(3) (CH2)1-2—C3-6 cycloalkyl;
R3 is
one of Y1 and Y2 is H, and the other of Y1 and Y2 is:
(1) H,
(2) C1-3 alkyl,
(3) C1-3 alkyl substituted with OH or OCH3,
(4) C1-4 alkyl substituted with from 2 to 4 OH,
(5) C3-6 cycloalkyl which is optionally substituted with C1-4 alkyl or phenyl,
(6) phenyl which is optionally substituted with from 1 to 3 substituents each of which is independently CH3, OCH3, CF3, OCF3, OH, Cl, Br, F, CN, NO2, C(O)N(H)CH3, C(O)N(CH3)2, CO2CH3, or S(O)2CH3,
(7) phenyl substituted with a saturated heterocyclic ring selected from the group consisting of:
wherein the asterisk denotes the point of attachment to the rest of the molecule,
(8) CH2-phenyl,
(9) CH2—O-phenyl,
(10) thienyl or pyridinyl, or
(11) benzo-1,3-dioxolyl;
R4 is H; and
R5 is H.

### Claim 14

A compound, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:
5-chloro-3-(phenylsulfonyl)-2-(4-pyridin-2-yl-1,3-thiazol-2-yl)-1H-indole;
5-chloro-3-(phenylsulfonyl)-2-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1H-indole;
5-chloro-3-(phenylsulfonyl)-2-(4-pyridin-4-yl-1,3-thiazol-2-yl)-1H-indole;
5-chloro-2-[5-(2-chlorophenyl)-1,2,4-oxadiazol-3-yl]-3-(phenylsulfonyl)-1H-indole;
5-chloro-3-(phenylsulfonyl)-2-(5-propyl-1,2,4-oxadiazol-3-yl)-1H-indole;
5-chloro-2-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-{5-[(1R,2R)-2-phenylcyclopropyl]-1,2,4-oxadiazol-3-yl}-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-[5-(phenoxymethyl)-1,2,4-oxadiazol-3-yl]-3-(phenylsulfonyl)-1H-indole;
5-chloro-3-(phenylsulfonyl)-2-(5-pyridin-4-yl-1,2,4-oxadiazol-3-yl)-1H-indole;
5-chloro-2-[5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-(5-methyl-1,2,4-oxadiazol-3-yl)-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-(5-cyclobutyl-1,2,4-oxadiazol-3-yl)-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-[5-(methoxyrnethyl)-1,2,4-oxadiazol-3-yl]-3-(phenylsulfonyl)-1H-indole;
2-(5-benzyl-1,2,4-oxadiazol-3-yl)-5-chloro-3-(phenylsulfonyl)-1H-indole;
5-chloro-2-(5-ethyl-1,2,4-oxadiazol-3-yl)-3-(phenylsulfonyl)-1H-indole;
5-bromo-2-(4-methyl-1H-imidazol-2-yl)-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-benzimidazole;
(1S,2R,3S)-1-{2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-imidazol-4-yl}butane-1,2,3,4-tetrol;
5-bromo-2-[4-(4-morpholin-4-ylphenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
1-{2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-imidazol-4-yl}propan-1-ol;
5-bromo-2-[4-(1-methoxypropyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-2-[4-(2,4-difluorophenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-2-(4-phenyl-1H-imidazol-2-yl)-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-2-[4-(4-chlorophenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-2-[4-(4-fluorophenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-2-[4-(3,4-difluorophenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
4-{2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-imidazol-4-yl}phenol;
5-bromo-2-[4-(4-methoxyphenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
5-bromo-3-(pyrrolidin-1-ylsulfonyl)-2-[4-(2-thienyl)-1H-imidazol-2-yl]-1H-indole;
2-[4-(1,3-benzodioxol-5-yl)-1H-imidazol-2-yl]-5-bromo-3-(pyrrolin-1-ylsulfonyl)-1H-indole;
methyl 5-{2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-imidazol-4-yl}-2-hydroxybenzoate;
5-bromo-2-[4-(4-nitrophenyl)-1H-imidazol-2-yl]-3-(pyrrolidin-1-ylsulfonyl)-1H-indole;
4-{2-[5-bromo-3-(pyrrolidin-1-ylsulfonyl)-1H-indol-2-yl]-1H-imidazol-4-yl}benzonitrile;
5-chloro-3-[(cyclobutylmethyl)sulfonyl]-2-(5-methyl-1H-imidazol-2-yl)-1H-indole;
5-chloro-3-[(cyclopentyl)sulfonyl]-2-(5-methyl-1H-imidazol-2-yl)-1H-indole;
5-chloro-3-[(2-methylbutyl)sulfonyl]-2-(5-methyl-1H-imidazol-2-yl)-1H-indole; and
5-chloro-3-[(pent-3-yl)sulfonyl]-2-(5-methyl-1H-imidazol-2-yl)-1H-indole.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising an effective amount of a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 1)

A pharmaceutical combination which is (i) a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and (ii) an HIV antiviral agent selected from the group consisting of HIV protease inhibitors, nucleoside HIV reverse transcriptase inhibitors, and HIV integrase inhibitors; wherein the compound of (i) or its pharmaceutically acceptable salt and the HIV antiviral agent of (ii) are each employed in an amount that renders the combination effective for the treatment of HIV infection or the treatment of AIDS.

### Claim 17 (depends on 1)

A method for the treatment HIV infection, or the treatment of AIDS, wherein the method comprises administering to a subject in need thereof an effective amount of a compound of Formula I, or a pharmaceutically acceptable salt thereof, as defined in claim 1.

### Claim 18

(canceled)

### Claim 19

(canceled)