# US 11,299,501 B2 · Diazaindole compounds

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- Number: US 11,299,501 B2
- Document ID: US11299501B2
- Status: Granted
- Kind: B2
- Application number: 16/955,108
- Filed: 2018-12-18
- Published: 2020-10-01
- Granted: 2022-04-12
- Earliest claimed: 2017-12-20
- Assignees: Bristol-Myers Squibb Company
- Applicants: Bristol-Myers Squibb Company
- Inventors: Alaric J. Dyckman; Dharmpal S. Dodd; Christopher P. Mussari; Brian K. Whiteley; Sreekantha Ratna Kumar; Anupama Kandhi Ramachandra Reddy
- Web page: https://patentgrep.com/patent/US11299501B2

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed are compounds of Formula (I) N-oxides, or salts thereof, wherein G, A, X, Y, Z, R1, and n are defined herein. Also disclosed are methods of using such compounds as inhibitors of signaling through Toll-like receptor 7, or 8, or 9, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating inflammatory and autoimmune diseases.

## Claims

### Claim 1

A compound of Formula (I)
or a salt thereof, wherein:
X is N;
Y is N;
Z is CR5;
G is:
(iv) a 9-membered heterocyclic ring selected from:
or
(v) 10-membered heterocyclic ring selected from:
A is:
(i) —O-L1-R6;
(ii) —NR7R8;
(iii) -L2-C(O)NR9R10;
(iv) —(CRxRx)1-3R11, C1-3 aminoalkyl, —(CRxRx)1-3NRxC(O)R11,
—(CRxRx)1-2NRxC(O)(CH2)1-2(piperidinyl),
(CRxRx)1-2NRxC(O)O(CH2)1-2(piperidinyl), or
—(CRxRx)1-2NRxC(O)(CH2)1-2NRxRx;
(v) —CRxR12R13, wherein R12 and R13 together with the carbon atom to which they are attached form a cyclic group selected from azabicyclo[4.1.1]octanyl, azepanyl, azetidinyl, C3-7 cycloalkyl, diazepanyl, diazaspiro[4.5]decanonyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, and quinuclidinyl, each substituted with zero to 4 R12a;
(vi) —CRx═CRx(piperidinyl); or
(vii) an aromatic group selected from [1,2,4]triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazolyl, indazolyl, isoquinolinyl, oxadiazolyl, oxazolyl, phenyl, pyrazinyl, pyrazolo[3,4-b]pyridinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinonyl, quinolinyl, quinoxalinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyrazinyl, tetrahydroimidazo[1,2-a]pyrazinyl, tetrahydroisoquinolinyl, tetrahydrothiazolo[5,4-c]pyridinyl, tetrahydrothieno[2,3-c]pyridinyl, thiadiazolyl, thiazolyl, thiooxadiazolyl, and triazolyl, each substituted with zero to 2 R14a and zero to 3 R14b;
L1 is bond, —(CRxRx)1-2—, —(CRxRx)1-2CRx(OH)—, —(CRxRx)1-2O—, —CRxRxC(O)—, —CRxRxC(O)NRx(CRxRx)0-4—, —CRxRxNRxC(O)(CRxRx)0-4—, or CRxRxNRxC(O)(CRxRx)0-4—;
L2 is a bond or —(CRxRx)1-3—;
R1 is H, Cl, —CN, C1-4 alkyl, C1-3 fluoroalkyl, C1-3 hydroxyalkyl, C1-3 hydroxy-fluoroalkyl, —CRv═CH2, C3-6 cycloalkyl, —CH2(C3-6 cycloalkyl), —C(O)O(C1-3 alkyl), or tetrahydropyranyl;
each R2 is independently halo, —CN, —OH, —NO2, C1-4 alkyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, C1-3 hydroxyalkyl, C1-3 aminoalkyl, —O(CH2)1-2OH, —(CH2)0-4O(C1-4 alkyl), C1-3 fluoroalkoxy, —(CH2)1-4O(C1-3 alkyl), —O(CH2)1-2OC(O)(C1-3 alkyl), —O(CH2)1-2NRxRx, —C(O)O(C1-3 alkyl), —(CH2)0-2C(O)NRyRy, —C(O)NRx(C1-5 hydroxyalkyl), —C(O)NRx(C2-6 alkoxyalkyl), —C(O)NRx(C3-6 cycloalkyl), —NRyRy, —NRy(C1-3 fluoroalkyl), —NRy(C1-4 hydroxyalkyl), —NRxCH2(phenyl), —NRxS(O)2(C3-6 cycloalkyl), —NRxC(O)(C1-3 alkyl), —NRxCH2(C3-6 cycloalkyl), —(CH2)0-2S(O)2(C1-3 alkyl), —(CH2)0-2(C3-6 cycloalkyl), —(CH2)0-2(phenyl), morpholinyl, dioxothiomorpholinyl, dimethyl pyrazolyl, methylpiperidinyl, methylpiperazinyl, amino-oxadiazolyl, imidazolyl, triazolyl, or —C(O)(thiazolyl);
R2a is C1-6 alkyl, C1-3 fluoroalkyl, C1-6 hydroxyalkyl, C1-3 aminoalkyl, —(CH2)0-4O(C1-3 alkyl), C3-6 cycloalkyl, —(CH2)1-3C(O)NRxRx, —CH2(C3-6 cycloalkyl), —CH2(phenyl), tetrahydrofuranyl, tetrahydropyranyl, or phenyl;
each R2b is independently H, halo, —CN, —NRxRx, C1-6 alkyl, C1-3 fluoroalkyl, C1-3 hydroxyalkyl, C1-3 fluoroalkoxy, —(CH2)0-2O(C1-3 alkyl), —(CH2)0-3C(O)NRxRx, —(CH2)1-3(C3-6 cycloalkyl), —C(O)O(C1-3 alkyl), —C(O)NRx(C1-3 alkyl), —CRx═CRxRx, or —CRx═CH(C3-6 cycloalkyl);
R2c is R2a or R2b;
R2d is R2a or R2b; provided that one of R2c and R2d is R2a, and the other of R2c and R2 is R2b;
R5 is F, Cl, —CN, C1-3 alkyl, C1-2 fluoroalkyl, or —OCH3;
R6 is:
(i) —CRxRxC(O)NRx(CRxRx)1-3OH, —CRxRxC(O)NRx(CRxRx)1-2NRxRx, or —CRxRxC(O)NRx(CRxRx)1-2CHFCRxRxOH; or
(ii) azabicyclo[3.2.1]octanyl, azaspiro[5.5]undecanyl, azetidinyl, C3-6 cycloalkyl, diazabicyclo[2.2.1]heptanyl, diazaspiro[3.5]nonanyl, morpholinyl, tetrahydrofuranyl, tetrahydropyranyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, or quinuclidinyl, each substituted with zero to 3 R6a;
each R6a is independently F, Cl, —OH, —CN, C1-6 alkyl, C1-4 fluoroalkyl, C1-6 hydroxyalkyl, —(CH2)1-2O(C1-3 alkyl), —NRxRx, —(CH2)1-2NRxRx, —(CRxRx)1-2S(O)2(C1-3 alkyl), —(CRxRx)1-2C(O)NRxRx, —C(O)(CRxRx)1-2NRxRx, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, azetidinyl, pyrrolidinyl, piperidinyl, isobutylpiperidinyl, piperazinyl, or —O(piperidinyl);
R7 is:
(i) R7a, —CH2R7a, —C(O)R7a, —C(O)CH(NH2)R7a, —C(O)(CH2)1-3NH2, —C(O)CH(NH2)(C1-4 alkyl), —C(O)CH(NH2)(CH2)1-2C(O)OH, —C(O)CH(NH2)(CH2)2-4NH2, or —C(O)CH(NH2)(CH2)1-3C(O)NH2; or
(ii) C3-6 cycloalkyl substituted with one substituent selected from NRx(CH2)2-3NRyRy, —NRx(methylpiperidinyl), —NRx(CH2)2-3(morpholinyl), dimethylamino piperidinyl, and piperazinyl substituted with a substituent selected from C1-4 alkyl, —C(O)CH3, —(CH2)1-2OCH3, —CH2(methylphenyl), —(CH2)2-3(pyrrolidinyl), C3-6 cycloalkyl, pyridinyl, and methylpiperidinyl;
R7a is azaspiro[3.5]nonanyl, C3-6 cycloalkyl, diazaspiro[3.5]nonanyl, diazaspiro[5.5]undecanyl, diazepanonyl, diazepanyl, morpholinyl, phenyl, piperazinyl, piperidinyl, pyrrolidinonyl, pyrrolidinyl, or pyrrolyl, each substituted with zero to 1 substituent selected from C1-3 alkyl, —NH2, methylpiperidinyl, methylpyrrolidinyl, —OCH2CH2(pyrrolidinyl), and —OCH2CH2NHCH2CH3; and zero to 4 substituents selected from —CH3;
R7b
(i) C1-4 alkyl, C1-3 hydroxyalkyl, —(CH2)2-3C≡CH, —(CH2)1-2O(C1-2 alkyl), —(CH2)1-2S(O)2(C1-2 alkyl), —(CH2)0-3NRxRy, —CH2C(O)NRxRx, —NRx(C1-4 hydroxyalkyl), —NRy(C1-2 cyanoalkyl), —NRx(C1-2 fluoroalkyl), —NRx(C2-4 hydroxyfluoroalkyl), —NRx(CH2)1-2C(O)NRxRx, —NRx(CH2)1-3NRxRx, —NRxCH2CH2NRxRx, —NRxC(O)(CH2)1-2NRxRx, —O(CH2)1-3NRxRx, —C(O)CH2NRxRx, —(CH2)1-2R7d, —NHR7d, —NH(CH2)1-2R7d, or —OR7d; or
(ii) azepanyl, azetidinyl, diazepanyl, dioxothiomorpholinyl, morpholinyl, oxaazaspiro[3.3]heptanyl, oxetanyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrahydroisoquinolinyl, each substituted with zero to 1 R8a and zero to 3 R8b,
each R7c is independently F, —CH3 or —CH2CN;
each R7c is independently F, Cl, —CN, C1-2 alkyl, —CF3, or —CH2CN;
R7d is azaspiro[3.5]nonanyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, morpholinyl, oxetanyl, phenyl, piperidinyl, pyrazolyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each substituted with zero to 1 substituent selected from C1-3 alkyl, —NRxRx, —C(O)CH3, methylpiperidinyl, methylpyrrolidinyl, tetramethylpiperidinyl, —OCH2CH2(pyrrolidinyl), and —OCH2CH2NHCH2CH3; and zero to 4 substituents selected from —CH3;
R8 is H or C1-3 alkyl;
or R7 and R8 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azetidinyl, diazepanonyl, diazepanyl, diazaspiro[3.5]nonanyl, diazaspiro[5.5]undecanyl, imidazolyl, imidazolidinonyl, octahydro-1H-pyrrolo[3,4-b]pyridinyl, piperazinyl, piperidinyl, pyrrolidinonyl, pyrrolidinyl, and pyrrolyl, wherein said heterocyclic ring is substituted with zero to 1 R7b and zero to 2 R7c,
R8a is —OH, C1-6 alkyl, C1-4 fluoroalkyl, C1-4 hydroxyalkyl, —(CH2)1-2O(C1-3 alkyl), —C(O)(C1-3 alkyl), —(CH2)1-2(C3-6 cycloalkyl), —(CH2)1-3(methyl phenyl), —(CH2)1-3(pyrrolidinyl), —(CH2)1-3(methylpyrazolyl), —(CH2)1-3(thiophenyl), —NRxRx, C3-6 cycloalkyl, methylpiperidinyl, pyridinyl, or pyrimidinyl;
each R8b is independently F, Cl, —CN, C1-3 alkyl, or —CF3;
R9 is C1-6 alkyl, hydroxyalkyl, C1-6 hydroxy fluoroalkyl, C1-3 aminoalkyl, —(CH2)1-2O(C1-3 alkyl), —(CH2)1-3NRxRx, —(CH2)1-2 C(O)NRxRx, —(CH2)1-3S(O)2OH, —(CRxRx)1-3NRxS(O)2(C1-2 alkyl), or —(CH2)0-3R9a;
R9a is C3-7 cycloalkyl, furanyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinyl, quinuclidinyl, thiazolyl, or octahydrocyclopenta[c]pyrrolyl, each substituted with zero to 3 substituents independently selected from F, Cl, —OH, C1-4 alkyl, C1-3 hydroxyalkyl, C1-3 hydroxy fluoroalkyl, C1-3 aminoalkyl, —NRyRy, oxetanyl, phenyl, piperazinyl, piperidinyl, and pyrrolidinyl;
R10 is H, C1-4 alkyl, —(CH2)1-3O(C1-2 alkyl), or C3-6 cycloalkyl;
or R9 and R10 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azabicyclo[3.1.1]heptanyl, azaspiro[5.5]undecanyl, diazabicyclo[2.2.1]heptanyl, diazabicyclo[3.1.1]heptanyl, diazabicyclo[3.2.0]heptanyl, diazaspiro[3.5]nonanyl, di azaspiro[4.4]nonanyl, diazaspiro[4.5]decanyl, diazepanyl, indolinyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, piperazinonyl, piperazinyl, piperidinyl, and pyrrolidinyl, each substituted with zero to 3 R10a;
each R10a is independently C1-4 alkyl, C1-4 hydroxyalkyl, —(CH2)1-3O(C1-3 alkyl), —(CH2)1-3NRxRx, —(CH2)1-2C(O)NRxRx, —(CH2)1-2(methyltriazolyl), —CH2CH2(phenyl), —CH2CH2(morpholinyl), —C(O)(C1-2 alkyl), —C(O)NRyRy, —C(O)CH2NRyRy, —NRyRy, —NHC(O)(C1-3 alkyl), —C(O)(furanyl), —O(piperidinyl), —C(O)CH2(diethylcarbamoylpiperidinyl), methylpiperazinyl, piperidinyl, methylpiperidinyl, diethylcarbamoylpiperidinyl, isopropylpiperidinyl, pyridinyl, trifluoromethylpyridinyl, pyrimidinyl, or dihydrobenzo[d]imidazolonyl;
R11 is azetidinyl, azaspiro[3.5]nonanyl, dioxidothiomorpholinyl, hexahydropyrrolo[3,4-c]pyrrolyl, morpholinyl, piperazinyl, piperidinyl, pyridinyl, or pyrrolidinyl, each substituted with zero to 3 substituents independently selected from halo, —CN, C1-4 alkyl, C1-3 aminoalkyl, —(CH2)1-2(phenyl), —C(O)CH2NRxRx, C1-5 hydroxyalkyl, —(CH2)1-2C(O)NRxRx, —(CH2)1-2S(O)2(C1-3 alkyl), —(CH2)1-2S(O)(C1-3 alkyl), oxetanyl, tetrahydrofuranyl, and tetrahydropyranyl;
each R12a is independently F, Cl, —OH, C1-6 alkyl, C1-4 fluoroalkyl, C1-4 cyanoalkyl, C1-6 hydroxyalkyl, —(CH2)1-2O(C1-3 alkyl), —(CH2)1-2C(O)NRxRx, —(CH2)1-2S(O)2(C1-2 alkyl), —(CH2)1-2NRxHS(O)2(C1-2 alkyl), —(CH2)1-2NRxRx, C1-3 alkoxy, —NRyRy, —NRx(C1-4 fluoroalkyl), —NRx(C1-2 cyanoalkyl), —NRxCH2NRxRx, —NRx(C1-4 hydroxyalkyl), —NRx(CRxRxCRxRx)O(C1-3 alkyl), —NRx(CH2C(O)NRxRx), —NRx(C1-3 alkoxy), —NRxCH2CH2S(O)2(C1-2 alkyl), —NRxC(O)CH3, —NRxC(O)(C1-2 fluoroalkyl), —NRxC(O)CRxRxNRxRx, —NRxC(O)CH2NRyRy, —NRxC(O)CH2NRx(C1-4 hydroxyalkyl), —NRx(CH2)1-2C(O)NRxRx, —NRxS(O)2(C1-2 alkyl), —C(O)(C1-5 alkyl), —C(O)(CH2)1-3O(C1-2 alkyl), —C(O)CRxRxNRyRy, R12b, —CRxRxR12b, —C(O)R12b, —C(O)CRxRxNRxR12b, —C(O)NRxR12b, —NRx(O)CRxRxR12b, —NRxR12b, —NRxCRxRxR12b, —N(CH2CN)R12b, —NRxC(O)CRxRxNRxR12b, —NRxC(O)CRxRxNRxCH2R12b, —NRxCRxRxC(O)NRxR12b, or —OR12b; or two R12a and the carbon atom to which they are attached form C═O;
R12b is azetidinyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, diazabicyclo[2.2.1]heptanyl, dioxolanyl, dioxidotetrahydrothiopyranyl, dioxidothiomorpholinyl, imidazolyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, octahydropyrrolo[3,4-c]pyrrolyl, oxaazaspiro[3.3]heptanyl, oxetanyl, phenyl, piperazinyl, piperazinonyl, piperidinyl, pyridinyl, pyrrolidinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydropyranyl, or triazolyl, each substituted with zero to 4 substituents independently selected from F, Cl, —OH, C1-4 alkyl, C1-3 fluoroalkyl, C1-3 hydroxyalkyl, C1-3 aminoalkyl, C1-4 alkoxy, —(CH2)1-2O(C1-3 alkyl), —NRxRx, —C(O)NRxRx, and —CRxRxS(O)2(C1-3 alkyl);
each R14a is independently is:
(i) H, halo, —OH, C1-6 alkyl, C1-23 fluoroalkyl, C1-4 hydroxyalkyl, —(CH2)0-2O(C1-3 alkyl), —CRxRxNRyRy, —CRxRxNRx(C1-3 cyanoalkyl), —CRxRxNRx((CH2)1-2O(C1-2 alkyl)), —CRxRxN((CH2)1-2OCH3)2, —CRxRxNRx(CH2C≡CRx), —CRxRxNRx(CH2)1-3NRxRx, —(CRxRx)1-3 CRxRxNRxRx, —CRx(NH2)(CH2)1-4NRxRx, —CRxRxNRx(CH2)1-2O(C1-3 alkyl), —CRxRxNRx(CH2)1-2O(CH2)1-2OH, —CRxRxNRx(CH2)1-3 S(O)2OH, —CRxRxC(O)NRxRx, —NRxRy, —NRx(CH2)1-3NRxRx, —NRxC(O)(C1-3 alkyl), —NRxC(O)(C1-3 fluoroalkyl), —NRC(O)O(C1-3 alkyl), —NRxC(O)(CH2)1-3NRxRx, —NRxCH2C(O)CH2NRxRx, —C(O)(C1-3 alkyl), —C(O)(CRxRx)1-30H, —C(O)CRxRxNRxRx, —C(O)NRxRx, —C(O)NRx(C1-2 cyanoalkyl), —C(O)NRx(CRxRx)1-3NRxRx, —C(O)N(CH2CH3)(CRxRx)1-3NRxRx, —C(O)NRx(CRxRx)1-2C(O)NRxRx, —C(O)NRx(CRxRx)1-3NRxC(O)(C1-2 alkyl), —O(CRxRx)1-3NRxRx, —S(O)2NRxRx, or —C(O)(CRxRx)1-2S(O)2(C1-2 alkyl);
(ii) 8-azabicyclo[3.2.1]octanyl, azaspiro[3.5]nonanyl, azetidinyl, benzo[c][1,2,5]oxadiazolyl, cyclopentyl, cyclohexyl, diazepanyl, morpholinyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinonyl, quinolinyl, quinuclidinyl, tetrahydroisoquinolinyl, tetrahydropyridinyl, or thiazolidinyl, each substituted with zero to 2 substituents independently selected from C1-4 alkyl, C1-2 fluoroalkyl, C1-4 hydroxyalkyl, —NRxRx, —(CH2) 1-2NRxRx, —C(O)(C1-2 alkyl), —C(O)CH2NRxRx, —C(O)O(C1-3 alkyl), —CH2C(O)NRxRx, C3-6 cycloalkyl, —CH2(phenyl), —CH2(pyrrolyl), —CH2(morpholinyl), —CH2(methylpiperazinyl), —CH2(thiophenyl), methylpiperidinyl, isobutylpiperidinyl, and pyridinyl; or
(iii) -L3-R14c;
each R14b is F, Cl, —OH, —CH3, or —OCH3;
R14c is adamantanyl, azepanyl, azetidinyl, C3-7 cycloalkyl, diazepanyl, imidazolyl, indolyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, phenyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, pyrrolyl, triazolyl, or tetrazolyl, each substituted with zero to 1 substituent selected from F, —OH, C1-4 alkyl, C1-3 hydroxyalkyl, —NRxRy, —NRC(O)CH3, —C(O)(C1-2 alkyl), —C(O)NRxRx, —C(O)N(CH2CH3)2, —C(O)(tetrahydrofuranyl), —C(O)O(C1-2 alkyl), —CH2C(O)NRxRy, morpholinyl, methylpiperidinyl, pyrazinyl, pyridinyl, and pyrrolidinyl;
L3 is —(CRxRx)1-3—, —CH(NH2)—, —CRxRxNRx—, —C(O)—, —C(O)NRx(CH2)0-4—, —NRxC(O)—, —NRxCH2—, —NRxCH2C(O)—, or —O(CH2)0-2—;
Rv is H, C1-2 alkyl, or C1-2 fluoroalkyl;
each Rx is independently H or —CH3;
each Ry is independently H or C1-6 alkyl; and
p is zero, 1, 2, 3, or 4.

### Claim 2 (depends on 1)

The compound according to claim 1, or a salt thereof, wherein:
A is:
(i) —O-L1-R6;
(ii) —NR7R8;
(iii) -L2-C(O)NR9R10;
(iv) —(CRxRx)1-2R11, C1-2 aminoalkyl, —(CRxRx)1-2NRxC(O)R11, —CH2NRxC(O)(CH2)1-2(piperidinyl), —CH2NRxC(O)OCH2(piperidinyl), or —CH2NRxC(O)(CH2)1-2NRxRx;
(v) —CRxR12R13, wherein R12 and R13 together with the carbon atom to which they are attached form a cyclic group selected from azabicyclo[4.1.1]octanyl, azepanyl, azetidinyl, C3-7 cycloalkyl, diazepanyl, diazaspiro[4.5]decanonyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, and quinuclidinyl, each substituted with zero to 3 R3a;
(vi) —CRx═CRx(piperidinyl); or
(vii) an aromatic group selected from [1,2,4]triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazolyl, indazolyl, isoquinolinyl, oxadiazolyl, oxazolyl, phenyl, pyrazinyl, pyrazolo[3,4-b]pyridinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinonyl, quinolinyl, quinoxalinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyrazinyl, tetrahydroimidazo[1,2-a]pyrazinyl, tetrahydroisoquinolinyl, tetrahydrothiazolo[5,4-c]pyridinyl, tetrahydrothieno[2,3-c]pyridinyl, thiadiazolyl, thiazolyl, thiooxadiazolyl, and triazolyl, each substituted with zero to 2 R14a and zero to 3 R14b;
L1 is bond, —(CRxRx)1-2—, —CH2C(O)—, —CH2C(O)NRx(CRxRx)0-2—, —CH2NRxC(O)—, or —CH2NRxC(O)CH2—;
L2 is a bond or —(CRxRx)1-2—;
R1 is H, Cl, —CN, C1-4 alkyl, C1-2 fluoroalkyl, C1-2 hydroxyalkyl, or —C(O)O(C1-2 alkyl);
each R2 is independently F, Cl, —CN, —OH, C1-3 alkyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 aminoalkyl, —(CH2)0-2O(C1-3 alkyl), C3-6 cycloalkyl, —NRxRx, —(CH2)0-2C(O)NRxRx, —(CH2)0-2S(O)2(C1-3 alkyl), —CH2(C3-6 cycloalkyl), —CH2(phenyl), or phenyl;
R2a is C1-4 alkyl, C1-2 fluoroalkyl, C1-4 hydroxyalkyl, —(CH2)1-3OCH3, C3-6 cycloalkyl, —CH2C(O)NRxRx, —CH2(C3-6 cycloalkyl), —CH2(phenyl), tetrahydrofuranyl, or phenyl;
each R2b is independently H, F, Cl, —CN, —NRxRx, C1-6 alkyl, C1-2 fluoroalkyl, C1-3 hydroxyalkyl, —(CH2)0-2O(C1-2 alkyl), —(CH2)0-2C(O)NRxRx, —(CH2)1-3(cyclopropyl), —C(O)O(C1-2 alkyl), —C(O)NRx(C1-3 alkyl), —CRx═CH2, or —CH═CH(C3-6 cycloalkyl);
R5 is F, Cl, —CN, C1-2 alkyl, or —OCH3;
R6 is:
(i) —CH2C(O)NHCH2CRxRxOH, —CH2C(O)NHCH2CH2CRxRxOH, —CH2C(O)NHCH2CH2NRxRx, or —CH2C(O)NHCH2CHFCRxRxOH; or
(ii) azabicyclo[3.2.1]octanyl, azaspiro[5.5]undecanyl, azetidinyl, C3-6 cycloalkyl, diazabicyclo[2.2.1]heptanyl, diazaspiro[3.5]nonanyl, morpholinyl, tetrahydropyranyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, or quinuclidinyl, each substituted with zero to 3 R6a;
each R6a is independently F, —OH, C1-4 alkyl, C1-4 fluoroalkyl, C1-4 hydroxyalkyl, —(CH2)1-2OCH3, —NRxRx, —(CH2)1-2NRxRx, —(CH2)1-2S(O)2(C1-2 alkyl), —(CH2)1-2C(O)NRxRx, —C(O)CH2NRxRx, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, piperidinyl, isobutylpiperidinyl, piperazinyl, or —O(piperidinyl);
R7 is:
(i) R7a, —CH2R7a, —C(O)R7a, —C(O)CH(NH2)R7a, —C(O)(CH2)1-3NH2, —C(O)CH(NH2)(C1-4 alkyl), —C(O)CH(NH2)(CH2)1-2C(O)OH, —C(O)CH(NH2)(CH2)2-4NH2, or —C(O)CH(NH2)(CH2)1-3C(O)NH2; or
(ii) C3-6 cycloalkyl substituted with one substituent selected from —NRx(CH2)2-3NRxRx, —NH(CH2)2-3NHCH3, —NH(methylpiperidinyl), —NH(CH2)2-3(morpholinyl), dimethylamino piperidinyl, and piperazinyl substituted with a substituent selected from C1-4 alkyl, —C(O)CH3, —(CH2)1-2OCH3, —CH2(methylphenyl), —(CH2)2-3(pyrrolidinyl), C3-6 cycloalkyl, pyridinyl, and methylpiperidinyl;
R7b is:
(i) C1-4 alkyl, C1-3 hydroxyalkyl, —(CH2)2-3C≡CH, —(CH2)1-2O(C1-2 alkyl), —(CH2)1-2S(O)2(C1-2 alkyl), —(CH2)0-3NRxRy, —CH2C(O)NRxRx, —NRx(C1-4 hydroxyalkyl), —NRy(C1-2 cyanoalkyl), —NRx(C1-2 fluoroalkyl), —NRx(C2-4 hydroxyfluoroalkyl), —NRx(CH2)1-2C(O)NRxRx, —NRx(CH2)1-3NRxRx, —NRxCH2CH2NRxRx, —NRxC(O)(CH2)1-2NRxRx, —O(CH2)1-3NRxRx, —C(O)CH2NRxRx, —(CH2)1-2R7d, —NHR7d, —NH(CH2)1-2R7d, or —OR7d; or
(ii) azepanyl, azetidinyl, diazepanyl, dioxothiomorpholinyl, morpholinyl, oxaazaspiro[3.3]heptanyl, oxetanyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrahydroisoquinolinyl, each substituted with zero to 1 R8a and zero to 3 R8b;
each R1c is independently F, —CH3 or —CH2CN;
R7d is azaspiro[3.5]nonanyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, morpholinyl, oxetanyl, phenyl, piperidinyl, pyrazolyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each substituted with zero to 1 substituent selected from C1-3 alkyl, —NH2, —C(O)CH3, methylpiperidinyl, methylpyrrolidinyl, tetramethylpiperidinyl, —OCH2CH2(pyrrolidinyl), and —OCH2CH2NHCH2CH3; and zero to 4 substituents selected from —CH3;
R8 is H or C1-2 alkyl;
or R7 and R8 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azetidinyl, diazepanonyl, diazepanyl, diazaspiro[3.5]nonanyl, diazaspiro[5.5]undecanyl, imidazolyl, imidazolidinonyl, octahydro-1H-pyrrolo[3,4-b]pyridinyl, piperazinyl, piperidinyl, pyrrolidinonyl, pyrrolidinyl, and pyrrolyl, wherein said heterocyclic ring is substituted with zero to 1 R7b and zero to 2 R7c;
R8a is —OH, C1-4 alkyl, C1-3 fluoroalkyl, —(CH2)1-2O(C1-2 alkyl), —C(O)(C1-2 alkyl), —CH2(C3-6 cycloalkyl), —(CH2)1-2(methyl phenyl), —(CH2)1-3(pyrrolidinyl), —(CH2)1-2(methylpyrazolyl), —(CH2)1-2(thiophenyl), —NRxRx, C3-6 cycloalkyl, methylpiperidinyl, or pyridinyl;
each R8b is independently F or —CH3;
R9 is C1-3 alkyl, C1-5 hydroxyalkyl, C2-5 hydroxy fluoroalkyl, C1-2 aminoalkyl, —(CH2)1-2O(C1-2 alkyl), —(CH2)1-3N(CH3)2, —(CH2)1-2C(O)NH2, —(CH2)1-2S(O)2OH,
(CH2)1-2CRxRxNHS(O)2CH3, or —(CH2)0-3R9a;
R9a is C5-7 cycloalkyl, furanyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinyl, quinuclidinyl, thiazolyl, or octahydrocyclopenta[c]pyrrolyl, each substituted with zero to 2 substituents independently selected from —OH, C1-3 alkyl, —NRxRx, oxetanyl, phenyl, piperazinyl, piperidinyl, and pyrrolidinyl; —R10 is H, C1-3 alkyl, —(CH2)1-2O(C1-2 alkyl), or C3-6 cycloalkyl;
or R9 and R10 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azabicyclo[3.1.1]heptanyl, azaspiro[5.5]undecanyl, diazabicyclo[2.2.1]heptanyl, diazabicyclo[3.1.1]heptanyl, diazabicyclo[3.2.0]heptanyl, diazaspiro[3.5]nonanyl, diazaspiro[4.4]nonanyl, diazaspiro[4.5]decanyl, diazepanyl, indolinyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, piperazinonyl, piperazinyl, piperidinyl, and pyrrolidinyl, each substituted with zero to 3 R10a;
each R10a is independently C1-3 alkyl, C1-3 hydroxyalkyl, —(CH2)1-2O(C1-2 alkyl), —(CH2)1-2NRxRx, —CH2C(O)NRxRx, —CH2(methyltriazolyl), —CH2CH2(phenyl), —CH2CH2(morpholinyl), —C(O)(C1-2 alkyl), —C(O)NH2, —C(O)N(C1-2 alkyl)2, —C(O)CH2NRxRx, —NRxRx, —NHC(O)(C1-2 alkyl), —C(O)(furanyl), —O(piperidinyl), —C(O)CH2(diethylcarbamoylpiperidinyl), methylpiperazinyl, piperidinyl, methylpiperidinyl, diethylcarbamoylpiperidinyl, isopropylpiperidinyl, pyridinyl, trifluoromethylpyridinyl, pyrimidinyl, or dihydrobenzo[d]imidazolonyl;
R11 is azetidinyl, azaspiro[3.5]nonanyl, dioxidothiomorpholinyl, hexahydropyrrolo[3,4-c]pyrrolyl, morpholinyl, piperazinyl, piperidinyl, pyridinyl, or pyrrolidinyl, each substituted with zero to 3 substituents independently selected from F, Cl, —CN, C1-3 alkyl, C1-2 aminoalkyl, —CH2(phenyl), —C(O)CH2NRxRx, —CH2CRxRxOH, —CH2C(O)NRxRx, —CH2CH2S(O)2(C1-3 alkyl), —CH2CH2S(O)(C1-3 alkyl), oxetanyl, tetrahydrofuranyl, and tetrahydropyranyl;
each R12a is independently —OH, C1-4 alkyl, C1-3 fluoroalkyl, C1-2 cyanoalkyl, C1-4 hydroxyalkyl, —(CH2)1-2O(C1-2 alkyl), —CH2C(O)NRxRx, —(CH2)1-2 S(O)2(C1-2 alkyl), —(CH2)1-2NHS(O)2(C1-2 alkyl), —(CH2)1-2NRxRx, C1-2 alkoxy, —NRyRy, —NRx(C fluoroalkyl), —NRx(CH2CRxRx)OCH3), —NRx(C1-2 cyanoalkyl), —NRxCH2NRxRx, —NRx(C1-4 hydroxyalkyl), —NRx(CH2C(O)NH2), —NRx(OCH3), —NRxCH2CH2S(O)2(C1-2 alkyl), —NRx(CH2CRxRx)OCH3), —NRxC(O)CH3, —NRxC(O)(C1-3 fluoroalkyl), —NRxC(O)CRxRxNRxRx, —NRxC(O)CH2NRyRy, —NRxC(O)CH2NRx(C hydroxyalkyl), —NRxCH2C(O)NRxRx, —NRxS(O)2CH3, —C(O)(C1-5 alkyl), —C(O)CH2O(C1-2 alkyl), —C(O)CH2CH2O(C1-2 alkyl), —C(O)CH2NRxRx, —C(O)CHRxNRyRy, R12b, —CRxRxR12b, —C(O)R12b, —C(O)CH2NRxR12b, —C(O)NRxR12b, —NRxC(O)CRxRxR12b, —NRxR12b, —NRxCRxRxR12b, —N(CH2CN)R12b, —NRxC(O)CH2NRxR12b, —NRxC(O)CH2NRxCH2R12b, —NRxCH2C(O)NRxR12b, or —OR12b; or two R12a and the carbon atom to which they are attached form C═O;
R12b is azetidinyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, diazabicyclo[2.2.1]heptanyl, dioxolanyl, dioxidotetrahydrothiopyranyl, dioxidothiomorpholinyl, imidazolyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, octahydropyrrolo[3,4-c]pyrrolyl, oxaazaspiro[3.3]heptanyl, oxetanyl, phenyl, piperazinyl, piperazinonyl, piperidinyl, pyridinyl, pyrrolidinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydropyranyl, or triazolyl, each substituted with zero to 4 substituents independently selected from F, Cl, —OH, C1-3 alkyl, C1-2 hydroxyalkyl, C1-2 alkoxy, —(CH2)1-2O(C1-2 alkyl), —C(O)NRxRx, and —CH2S(O)2(C1-2 alkyl);
each R14a is independently:
(i) H, F, Cl, —OH, C1-5 alkyl, C1-2 fluoroalkyl, C1-2 hydroxyalkyl, —(CH2)0-2OCH3, —CHRxNRx(C1-5 alkyl), —CHRxNRx(C1-2 cyanoalkyl), —CHRxNRx((CH2)1-2OCH3), —CHRxN((CH2)1-2OCH3)2, —CH2NRx(CH2C≡CRx), —CH2NRxCH2CH2NRxRx, —(CH2)1-3CRxRxNRxRx, —CH(NH2)(CH2)3-4NRxRx, —CH2NRx(CH2)1-2O(C1-3 alkyl), —CH2NRx(CH2)1-2O(CH2)1-2OH, —CH2NH(CH2)1-2S(O)2OH, —CH2C(O)NRxRx, —NRxRy, —NRx(CH2)2-3NRxRx, —NRxC(O)(C1-2 alkyl), —NRxC(O)(C1-2 fluoroalkyl), —NRxC(O)O(C1-3 alkyl), —NRxC(O)(CH2)1-2NRxRx, —NRxCH2C(O)CH2NRxRx, —C(O)(C1-2 alkyl), —C(O)CH2CRxRxOH, —C(O)CH2NRxRx, —C(O)NRxRx, —C(O)NRx(CH2CN), —C(O)NRx(CRxRx)2-3NRxRx, —C(O)N(CH2CH3)(CRxRx)2-3NRxRx, —C(O)NRxC H2C(O)NRxRx, —C(O)NRxCH2CH2NRxC(O)CH3, —O(CRxRx)2-3NRxRx, —S(O)2NRxRx, or —C(O)CH2S(O)2(C1-2 alkyl);
(ii) 8-azabicyclo[3.2.1]octanyl, azaspiro[3.5]nonanyl, azetidinyl, benzo[c][1,2,5]oxadiazolyl, cyclopentyl, cyclohexyl, diazepanyl, morpholinyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinonyl, quinolinyl, quinuclidinyl, tetrahydroisoquinolinyl, tetrahydropyridinyl, or thiazolidinyl, each substituted with zero to 2 substituents independently selected from C1-4 alkyl, C1-2 fluoroalkyl, C1-4 hydroxyalkyl, —NRxRx, —(CH2)1-2NRxRx, —C(O)(C1-2 alkyl), —C(O)CH2NRxRx, —C(O)O(C1-3 alkyl), —CH2C(O)NRxRx, C3-6 cycloalkyl, —CH2(phenyl), —CH2(pyrrolyl), —CH2(morpholinyl), —CH2(methylpiperazinyl), —CH2(thiophenyl), methylpiperidinyl, isobutylpiperidinyl, and pyridinyl; or
(iii) -L3-R14c;
each R14b is F, —CH3, or —OCH3;
L3 is —(CRxRx)1-3—, —CH(NH2)—, —CRxRxNH—, —C(O)—, —C(O)NRx(CH2)0-4—, —NRx—, —NRxC(O)—, —NRxCH2—, —NRxCH2C(O)—, —O—, or —O(CH2)1-2—; and
R14c is adamantanyl, azetidinyl, C3-6 cycloalkyl, diazepanyl, imidazolyl, indolyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, phenyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrazolyl, each substituted with zero to 1 substituent selected from F, —OH, C1-4 alkyl, C1-3 hydroxyalkyl, —NRxRy, —NRxC(O)CH3, —C(O)(C1-2 alkyl), —C(O)NRxRx, —C(O)N(CH2CH3)2, —C(O)(tetrahydrofuranyl), —C(O)O(C1-2 alkyl), —CH2C(O)NRxRy, morpholinyl, methylpiperidinyl, pyrazinyl, pyridinyl, and pyrrolidinyl.

### Claim 3 (depends on 1)

The compound according to claim 1, or a salt thereof, wherein:
A is:
(i) —O-L1-R6;
(ii) —NR7R8;
(iii) -L2-C(O)NR9R10;
(iv) —CHRxR11, —CH2CH2R11, —CH2NH2, —CH2NHC(O)R11, —CH2NHC(O)CH2CH2(piperidinyl), —CH2NHC(O)OCH2(piperidinyl), or —CH2NHC(O)CH2CH2N(CH3)2;
(v) —CHR12R13, wherein R12 and R13 together with the carbon atom to which they are attached form a cyclic group selected from azabicyclo[4.1.1]octanyl, azepanyl, azetidinyl, C3-6 cycloalkyl, diazaspiro[4.5]decanonyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperidinyl, pyrrolidinyl, and quinuclidinyl, each substituted with zero to 3 R12a;
(vi) —CH═CH(piperidinyl); or
(vii) an aromatic group selected from [1,2,4]triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazolyl, indazolyl, isoquinolinyl, oxadiazolyl, oxazolyl, phenyl, pyrazinyl, pyrazolo[3,4-b]pyridinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinonyl, quinolinyl, quinoxalinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyrazinyl, tetrahydroimidazo[1,2-a]pyrazinyl, tetrahydroisoquinolinyl, tetrahydrothiazolo[5,4-c]pyridinyl, tetrahydrothieno[2,3-c]pyridinyl, thiadiazolyl, thiazolyl, thiooxadiazolyl, and triazolyl, each substituted with zero to 2 R14a and zero to 3 R14b;
L1 is bond, —CH2—, —CH2CH2—, —CH2C(O)—, —CH2C(O)NH—, —CH2C(O)N(CH3)—, —CH2C(O)NHCH2—, or —CH2C(O)NHCH2CH2—;
L2 is a bond, —CH(CH3)—, —C(CH3)2—, or —CH2CH2—;
R6 is:
(i) —CH2C(O)NHCH2C(CH3)2OH, —CH2C(O)NHCH2CH2C(CH3)2OH, —CH2C(O)NHCH2CH2NH2, or —CH2C(O)NHCH2CHFC(CH3)2OH; or
(ii) azabicyclo[3.2.1]octanyl, azaspiro[5.5]undecanyl, azetidinyl, cyclohexyl, diazabicyclo[2.2.1]heptanyl, diazaspiro[3.5]nonanyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, or quinuclidinyl, each substituted with zero to 2 R6a;
each R6a is independently F, —OH, —CH3, —CH2CH2CH3, —C(CH3)2, —CH2CH(CH3)2, —CH2CH2CH2CF3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CH(CH3)OH, —CH2C(CH3)2OH, —CH2CH2OCH3, —NH2, —N(CH3)2, —CH2NH2, —CH2CH2NH2, —CH2CH2S(O)2CH3, —CH2C(O)N(CH3)2, —C(O)CH2N(CH3)2, oxetanyl, tetrahydropyranyl, piperidinyl, isobutylpiperidinyl, or —O(piperidinyl);
R7 is:
(i) —CH2(isopropyl azaspiro[3.5]nonanyl), —CH2(methylpyrrolidinyl), —C(O)(CH2)1-3NH2, —C(O)CH(NH2)CH2CH2CH3, —C(O)CH(NH2)CH2CH(CH3)2, —C(O)CH(NH2)CH(CH3)CH2CH3, —C(O)CH(NH2)CH2CH2C(O)OH, —C(O)CH(NH2)(CH2)3-4NH2, —C(O)CH(NH2)(CH2)1-2C(O)NH2, —C(O)CH(NH2)(cyclohexyl), —C(O)CH(NH2)(phenyl), —C(O)(aminocyclohexyl), —C(O)(morpholinyl), —C(O)(pyrrolidinyl), pentamethylpiperidinyl, methylpiperidinyl-piperidinyl, methylpyrrolidinyl-pyrrolidinyl, or phenyl substituted with —OCH2CH2(pyrrolidinyl) or —OCH2CH2NHCH2CH3; or
(ii) cyclohexyl substituted with —NRx(CH2)2-3N(CH3)2, —NHCH2CH2NHCH3, —NH(methylpiperidinyl), —NH(CH2)2-3(morpholinyl), dimethylamino piperidinyl, or piperazinyl substituted with —CH3, —CH2CH3, —C(CH3)3, —CH2CH(CH3)2, —C(O)CH3, —CH2CH2OCH3, —CH2(methylphenyl), —(CH2)2-3(pyrrolidinyl), cyclopentyl, pyridinyl, or methylpiperidinyl;
R7b is:
(i) —CH3, —CH(CH3)2, —C(CH3)2OH, —CH2CH2CH2C≡CH, —CH2CH2OCH3, —CH2CH2S(O)2CH3, —(CH2)1-2NRxRx, —CH2C(O)NRxRx, —NRxRy, —NRx(C1-4 hydroxyalkyl), —NRy(C1-2 cyanoalkyl), —NRx(C1-2 fluoroalkyl), —NRx(C2-4 hydroxyfluoroalkyl), —NRx(CH2)1-2C(O)NRxRx, —NRx(CH2)1-3NRxRx, —NRxCH2CH2N(CH3)2, —NRxC(O)(CH2)1-2NRxRx, —OCH2CH2N(CH3)2, —C(O)CH2NRxRx, —(CH2)1-2R7d, —NHR7d, —NH(CH2)1-2R7a, or —OR7d; or
(ii) azepanyl, azetidinyl, diazepanyl, dioxothiomorpholinyl, morpholinyl, oxaazaspiro[3.3]heptanyl, oxetanyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrahydroisoquinolinyl, each substituted with zero to 1% a and zero to 3 R8b;
each R7c is independently —CH3 or —CH2CN;
R7d is azaspiro[3.5]nonanyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, morpholinyl, oxetanyl, phenyl, piperidinyl, pyrazolyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each substituted with zero to 1 substituent selected from C1-3 alkyl, —NH2, —C(O)CH3, methylpiperidinyl, methylpyrrolidinyl, tetramethylpiperidinyl, —OCH2CH2(pyrrolidinyl), and —OCH2CH2NHCH2CH3; and zero to 4 substituents selected from —CH3;
R8 is H, —CH3 or —CH2CH3;
or R7 and R8 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azetidinyl, diazepanonyl, diazepanyl, diazaspiro[3.5]nonanyl, diazaspiro[5.5]undecanyl, imidazolidinonyl, octahydro-1H-pyrrolo[3,4-b]pyridinyl, piperazinyl, piperidinyl, pyrrolidinonyl, and pyrrolidinyl, wherein said heterocyclic ring is substituted with zero to 1 R7b and zero to 2 R7c;
R8a is —OH, —CH3, —CH2CH3, —CH(CH3)2, —C(CH3)3, —CH2CH(CH3)2, —CH2CH2OCH3, —CH2CH2CF3, —C(O)CH3, —CH2(cyclopropyl), —CH2(methyl phenyl), —(CH2)2-3(pyrrolidinyl), —CH2(methylpyrazolyl), —CH2(thiophenyl), —NRxRx, cyclopentyl, methylpiperidinyl, or pyridinyl;
each R8b is —CH3;
R9 is —CH3, —CH2CH2OH, —CH2C(CH3)2OH, —CH2C(CH3)2CH2OH, —CH2CHFC(CH3)2OH, —CH2CH2C(CH3)2OH, —CH(CH2OH)2, —CH2CH2OCH3, —CH2CH2NH2, —CH2CH2N(CH3)2, —CH2CH2CH2N(CH3)2, —CH2CH2C(O)NH2, —CH2S(O)2OH, —CH2CH2C(CH3)2NHS(O)2CH3, or —(CH2)0-3R9a;
R9a is cyclohexyl, cycloheptyl, furanyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinyl, quinuclidinyl, thiazolyl, or octahydrocyclopenta[c]pyrrolyl, each substituted with zero to 2 substituents independently selected from —OH, C1-3 alkyl, —NH2, —N(CH3)2, oxetanyl, phenyl, piperazinyl, piperidinyl, and pyrrolidinyl;
R10 is H, —CH3, —CH2CH3, —CH2CH2OCH3, or cyclopropyl;
or R9 and R10 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azabicyclo[3.1.1]heptanyl, azaspiro[5.5]undecanyl, diazabicyclo[2.2.1]heptanyl, diazabicyclo[3.1.1]heptanyl, diazabicyclo[3.2.0]heptanyl, diazaspiro[3.5]nonanyl, diazaspiro[4.4]nonanyl, diazaspiro[4.5]decanyl, diazepanyl, indolinyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, piperazinonyl, piperazinyl, piperidinyl, and pyrrolidinyl, each substituted with zero to 2 R10a;
each R10a is independently —CH3, —CH2CH3, —CH(CH3)2, —CH2OH, —CH2CH2OH, —CH2OCH3, —CH2CH2OCH3, —CH2NH2, —CH2CH2NH2, —CH2CH2NH(CH3), —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2(methyltriazolyl), —CH2CH2(phenyl), —CH2CH2(morpholinyl), —C(O)CH3, —C(O)NH2, —C(O)N(CH2CH3)2, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —NH2, —N(CH3)2, —NHC(O)CH3, —C(O)(furanyl), —O(piperidinyl), —C(O)CH2(diethylcarbamoylpiperidinyl), methylpiperazinyl, piperidinyl, methylpiperidinyl, diethylcarbamoylpiperidinyl, isopropylpiperidinyl, pyridinyl, trifluoromethylpyridinyl, pyrimidinyl, or dihydrobenzo[d]imidazolonyl;
R11 is azetidinyl, azaspiro[3.5]nonanyl, dioxidothiomorpholinyl, hexahydropyrrolo[3,4-c]pyrrolyl, morpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl, each substituted with zero to 2 substituents independently selected from F, —CH3, —CH(CH3)2, —CH2CN, —CH2(phenyl), —C(O)CH2N(CH3)2, —CH2C(CH3)2OH, —CH2C(O)N(CH3)2, —CH2CH2S(O)2CH3, —CH2CH2S(O)CH3, oxetanyl, and tetrahydropyranyl;
each R12a is independently —OH, —CH3, —CH2CH2CH3, —CH(CH3)2, —CH2CH(CH3)2, —CF3, —CH2CF3, —CH2CH2CH2CF3, —CH2CN, —CH2C(CH3)2OH, —CH2CH2OCH3, —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2C(O)NH2, —CH2CH2S(O)2CH3, —CH2CH2NHS(O)2CH3, —CH2NRxRx, —CH2CH2NH(CH3), —OCH3, —NRxRy, —NRx(C2-4 fluoroalkyl), —NRx(CH2CRxRxH2OCH3), —NH(CH2CN), —N(CH3)CH2N(CH3)2, —NH(CH2C(CH3)2OH), —NRx(CH2C(O)NH2), —N(CH3)(OCH3), —NRxCH2CH2S(O)2CH3, —NHC(O)CH3, —NHC(O)CH2CF3, —NHC(O)CHRxNH(CH3), —NRxC(O)CH2N(CH3)2, —NHC(O)CH2N(CH3)(CH2CH3), —NHC(O)CH2N(CH2CH3)2, —NHC(O)CH2NH(CH2C(CH3)2OH), —NHCH2C(O)NRx(CH3), —NHS(O)2CH3, —C(O)C(CH3)3, —C(O)CH(CH2CH3)2, —C(O)CH2OCH3, —C(O)CH2CH2OCH3, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —C(O)CH(CH3)NH(CH3), —C(O)CH2N(CH3)(CH2CH3), —C(O)CH2N(CH2CH3)2, R12b, —CH2R12b, —C(O)R12b, —C(O)CH2R12b, —C(O)CH2NHR12b, —C(O)NRxR12b, —NRxC(O)CH2R12b, —NRxR12b, —NRxCH2R12b, —N(CH2CMR12b, —NHC(O)CH2NRxR12b, —NHC(O)CH2NRxCH2R12b, —NHCH2C(O)NHR12b, or —OR12b; or two R12a and the carbon atom to which they are attached form C═O;
R12b is azetidinyl, bicyclo[1.1.1]pentanyl, cyclopropyl, diazabicyclo[2.2.1]heptanyl, dioxolanyl, dioxidotetrahydrothiopyranyl, dioxidothiomorpholinyl, imidazolyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, octahydropyrrolo[3,4-c]pyrrolyl, oxaazaspiro[3.3]heptanyl, oxetanyl, phenyl, piperazinyl, piperazinonyl, piperidinyl, pyridinyl, pyrrolidinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydropyranyl, or triazolyl, each substituted with zero to 4 substituents independently selected from F, —OH, —CH3, —CH(CH3)2, —CH2OH, —OCH3, —CH2CH2OCH3, —NRxRx, —C(O)NH2, and —CH2S(O)2CH3;
each R14a is independently:
(i) H, F, Cl, —OH, —CH3, —CH(CH3)2, —CH(CH3)(CH2CH3), —CH2CH2CH2C(CH3)2, —CF3, —CH2CF3, —CH2OH, —OCH3, —CH2CH2OCH3, —CHRxNRx(CH3), —CH2N(CH3)(CH(CH3)2), —CH2NH(CH2C(CH3)3), —CH2NH(CH2CN), —CH2N(CH3)(CH2CH2OCH3), —CH2N(CH2CH2OCH3)2, —CH2NRx(CH2C≡CH), —CH2NHCH2CH2N(CH3)2, —CH2CH2NRx(CH3), —CH2CRx(CH3)NH2, —CH2CH2CH2N(CH3)2, —CH2CH2CH2CH2NH2, —CH(NH2)(CH2)3-4NH2, —CH2NHCH2CH2O(C1-3 alkyl), —CH2NHCH2CH2OCH2CH2OH, —CH2NHCH2CH2S(O)2OH, —CH2C(O)NRx(CH3), —NRxRx, —NH(CH(CH3)2), —NHCH2CH2NH(CH3), —NHCH2CH2CH2N(CH3)2, —NHC(O)CH3, —NHC(O)CF3, —NHC(O)OC(CH3)3, —NHC(O)CH2N(CH3)2, —NHC(O)CH2CH2N(CH3)2, —NHCH2C(O)CH2NH(CH3), —C(O)CH3, —C(O)CH2CH(CH3)OH, —C(O)CH2NRx(CH3), —C(O)NRxRx, —C(O)NH(CH2CN), —C(O)NHCH2CH2CH2NRxRx, —C(O)NHCH2CH(CH3)CH2NH2, —C(O)NHCH2C(O)NH2, —C(O)N(CH3)CH2CH2CH2N(CH3)2, —C(O)N(CH2CH3)CH2CH2N(CH3)2, —OCH2CH2CH2N(CH3)2, —C(O)NHCH2CH2NHC(O)CH3, —S(O)2NH2, or —C(O)CH2S(O)2CH3;
(ii) 8-azabicyclo[3.2.1]octanyl, azaspiro[3.5]nonanyl, azetidinyl, benzo[c][1,2,5]oxadiazolyl, cyclopentyl, cyclohexyl, diazepanyl, morpholinyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinonyl, quinolinyl, quinuclidinyl, tetrahydroisoquinolinyl, tetrahydropyridinyl, or thiazolidinyl, each substituted with zero to 2 substituents independently selected from —CH3, —CH(CH3)2, —CH2CH(CH3)2, —CF3, —CH2CH2CF3, —CH2CH2OH, —CH2CH2CH(CH3)OH, —NH2, —CH2N(CH3)2, —CH2CH2NH(CH3), —C(O)CH3, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —C(O)O(C(CH3)3), —CH2C(O)NRx(CH3), cyclobutyl, cyclopentyl, —CH2(phenyl), —CH2(pyrrolyl), —CH2(morpholinyl), —CH2(methylpiperazinyl), —CH2(thiophenyl), methylpiperidinyl, isobutylpiperidinyl, and pyridinyl; or
(iii) -L3-R14c;
each R14b is —CH3;
L3 is —(CH2)1-3—, —CH(CH3)—, —CH(NH2)—, —CH2NH—, —C(O)—, —C(O)NH(CH2)0-4—, —C(O)N(CH3)CH2CH2—, —NH—, —NHC(O)—, —NHCH2—, —NHCH2C(O)—, —O—, or —OCH2CH2—;
R14c is adamantanyl, azetidinyl, cyclopropyl, cyclohexyl, diazepanyl, imidazolyl, indolyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, phenyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrazolyl, each substituted with zero to 1 substituent selected from —OH, —CH3, —CH(CH3)2, —CH2CH(CH3)2, —C(CH3)2OH, —NH2, —N(CH3)2, —NH(C(CH3)2, —NHC(O)CH3, —C(O)CH3, —C(O)NH2, —C(O)N(CH2CH3)2, —C(O)(tetrahydrofuranyl), —C(O)OCH2CH3, —CH2C(O)NH(CH(CH3)2, morpholinyl, methylpiperidinyl, pyrazinyl, pyridinyl, and pyrrolidinyl; and
p is zero, 1, 2, or 3.

### Claim 4 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein:
X is N;
Y is N; and
Z is CR5.

### Claim 5 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein:
G is:

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically-acceptable salt thereof; and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

A method of treating an autoimmune disease or a chronic inflammatory disease, comprising administering to a mammalian patent a compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein said autoimmune disease or chronic inflammatory disease is selected from systemic lupus erythematosus (SLE), rheumatoid arthritis, multiple sclerosis (MS), and Sjögren's syndrome.

### Claim 8 (depends on 1)

The compound according to claim 1 or a salt thereof, wherein said compound is selected from:
6-(3,4-dimethoxyphenyl)-2-(1′-isobutyl-[1,4′-bipiperidin]-4-yl)-7-methyl-5H-pyrrolo[3,2-d]pyrimidine (6);
5-(7-isopropyl-2-(piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (7);
5-(7-isopropyl-2-(1-(oxetan-3-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (8);
2-(4-(6-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N-methylacetamide (9);
2-(4-(6-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (10);
2-(dimethylamino)-1-(4-(7-isopropyl-6-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)ethan-1-one (11);
5-(7-isopropyl-2-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (12);
6-(7-isopropyl-2-(1-(tetrahydro-2H-pyran-4-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine (13);
6-(7-isopropyl-2-(1-(oxetan-3-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine (14);
1-(4-(7-isopropyl-6-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl) piperidin-1-yl)-2-methylpropan-2-ol (15);
7-ethyl-2-(1′-isopropyl-[1,4′-bipiperidin]-4-yl)-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (16);
6-(3,4-dimethoxyphenyl)-7-isopropyl-2-(piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (17);
1-(4-(6-(3,4-dimethoxyphenyl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl) piperidin-1-yl)-2-(dimethylamino)ethan-1-one (18);
6-(7-isopropyl-2-(1-(oxetan-3-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine (19);
1-(4-(7-isopropyl-6-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl) piperidin-1-yl)-2-methylpropan-2-ol (20);
5-(7-isopropyl-2-(1-(tetrahydro-2H-pyran-4-yl) piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (21);
6-(3,4-dimethoxyphenyl)-7-isopropyl-2-(1′-isopropyl-[1,4′-bipiperidin]-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (22);
7-ethyl-2-(1′-isopropyl-[1,4′-bipiperidin]-4-yl)-6-(2-methylpyridin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (23);
6-(7-isopropyl-2-(1-(oxetan-3-yl)piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-8-methyl-[1,2,4]triazolo[1,5-a]pyridine (24);
4-(7-ethyl-2-(1′-isopropyl-[1,4′-bipiperidin]-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1H-pyrazolo[3,4-b]pyridine (25);
6-(3,4-dimethoxyphenyl)-7-ethyl-2-(1′-isopropyl-[1,4′-bipiperidin]-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (26);
1-(4-(6-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-2-methylpropan-2-ol (27);
1-(4-(6-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-2-(dimethylamino)ethan-1-one (28);
2-(4-(7-isopropyl-6-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (29);
2-(4-(7-isopropyl-6-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N-methylacetamide (30);
2-(4-(7-isopropyl-6-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (31);
2-(4-(6-(1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (32);
5-(2-(1-(dimethylglycyl)piperidin-4-yl)-7-isopropyl-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (33);
5-(7-isopropyl-2-(1-methylpiperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)-1,3-dimethylpyridin-2(1H)-one (34);
2-(4-(7-isopropyl-6-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N-methylacetamide (35);
(R)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(piperidin-2-ylmethyl)-1,3,4-oxadiazole (36);
3-(5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-yl)-N,N-dimethylpropan-1-amine (37);
2-(5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-yl)-N-methylethan-1-amine (38);
2-(5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-yl)propan-2-amine (39);
(S)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(piperidin-3-yl)-1,3,4-oxadiazole (40);
(R)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(pyrrolidin-3-yl)-1,3,4-oxadiazole (41);
1-(5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-yl)-N-methylmethanamine (42);
(R)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(piperidin-3-yl)-1,3,4-oxadiazole (43);
(S)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(pyrrolidin-3-yl)-1,3,4-oxadiazole (44);
(S)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(pyrrolidin-2-ylmethyl)-1,3,4-oxadiazole (45);
(S)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(piperidin-2-ylmethyl)-1,3,4-oxadiazole (46);
(R)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(pyrrolidin-2-ylmethyl)-1,3,4-oxadiazole (47);
2-(5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-yl)-N,N-dimethylethan-1-amine (48);
methyl 6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidine-2-carboxylate (49);
2-(4-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (50);
2-(1-((1H-imidazol-4-yl)methyl)piperidin-4-yl)-6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidine (51);
6-(3,4-dimethoxyphenyl)-7-ethyl-2-(1-((4-methyl-1H-imidazol-2-yl)methyl) piperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine (52);
5-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-1,3,4-oxadiazol-2-amine (53);
(R)-2-(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl)-5-(piperidin-3-yl)-1,3,4-oxadiazole (54);
(6-(3,4-dimethoxyphenyl)-7-ethyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl) (hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (55);
6-(3,4-dimethoxyphenyl)-7-ethyl-N-(1-isopropylpiperidin-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-2-carboxamide (56); or
2-(4-(7-isopropyl-6-(8-methoxy-[1,2,4]thazolo[1,5-a]pyridin-6-yl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)piperidin-1-yl)-N,N-dimethylacetamide (57).