# US 8,772,480 B2 · Inhibitors of PI3 kinase and/or mTOR

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- Number: US 8,772,480 B2
- Document ID: US8772480B2
- Status: Granted
- Kind: B2
- Application number: 13/681,230
- Filed: 2012-11-19
- Published: 2013-03-28
- Granted: 2014-07-08
- Earliest claimed: 2009-04-28
- Assignees: Amgen Inc.
- Applicants: Amgen Inc.
- Inventors: Kristin L. Andrews; Yunxin Y. Bo; Shon Booker; Victor J. Cee; Noel D'Angelo; Bradley J. Herberich; Fang-Tsao Hong; Claire L. M. Jackson; Brian Alan Lanman; Hongyu Liao; Longbin Liu; Nobuko Nishimura; Mark H. Norman; Liping H. Pettus; Anthony B. Reed; Adrian Leonard Smith; Seifu Tadesse; Nuria A. Tamayo; Bin Wu; Ryan Wurz; Kevin C. Yang
- Web page: https://patentgrep.com/patent/US8772480B2

## CPC

- C07D 473/00: Heterocyclic compounds containing purine ring systems
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 401/14: 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

The present invention relates to compounds of Formula I, or a pharmaceutically acceptable salt thereof; methods of treating diseases or conditions, such as cancer, using the compounds; and pharmaceutical compositions containing the compounds, wherein the variables are as defined herein.

## Claims

### Claim 1

A compound of Formula I, or a pharmaceutically acceptable salt thereof,
wherein Ar1 is a 5 to 10 membered monocyclic or bicyclic ring that can contain from zero to four heteroatoms independently selected from O, N or S, and which ring can be unsubstituted or substituted with groups independently selected from C1-4haloalkyl, halo, oxo, —OCHF2, —CN, nitro, —C(═O)NRaRa, —C(═O)Rb, —C(═O)ORb, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —O—C1-6alkylN(Ra)C(═O)ORb, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkyl NRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —C1-6alkyl, —C2-6alkenyl, or —C2-6 alkynyl, wherein —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl are substituted by 0, 1, 2 or 3 substituents independently selected from C1-4haloalkyl, halo, cyano, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —N(Ra)(CRaRa)n—Y, —(CRaRa)nY, or —(CRaRa)nORa;
Y is a saturated, partially saturated or unsaturated 5-, 6- or 7-membered monocyclic ring or 6-, 7-, 8-, 9-, or 10-membered bicyclic ring containing 0, 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, which is substituted with 0, 1, or 2 substitutents independently selected from C1-8alkyl, C2-6alkenyl, C2-6alkynyl, C1-4haloalkyl, halo, —CN, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa or —NRaC2-6alkylORa;
each Ra is independently hydrogen or Rb;
each Rb is independently phenyl, benzyl, C1-6alkyl, C4-8heterocycloalkyl, or C3-8cycloalkyl, wherein the phenyl, benzyl, C1-6alkyl, C4-8heterocycloalkyl or C3-8cycloalkyl is substituted by 0, 1, 2 or 3 substituents independently selected from halo, —OH, —S(═O)2Rb, —OC2-6alkylORa, C1-4alkyl, C1-3haloalkyl, —OC1-4alkyl, —NH2, —CN, or —NRaRa;
each Rc is independently hydrogen, —ORa, —NRaRa, —CF3, C1-6alkyl, or the group CRcRc can form a C3-8cycloalkyl ring;
each n is independently 0, 1, 2, or 3;
one of Z1, Z2, Z3 or Z4 is N and the others are CR;
each R is independently selected from hydrogen, oxo, C1-4haloalkyl, halo, —OCHF2, —CN, nitro, —C(═O)NRaRa, —C(═O)Rb, —C(═O)ORb, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —(CRaRa)nORa, —OC(═O)NRaRa, —O—C1-6alkylN(Ra)C(═O)ORb, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —(CRcRc)nNRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —(CRcRc)nC4-8heterocycloalkyl, —(CRcRc)nC6-8aryl, —(CRcRc)nC5-8heteroaryl, —(CRcRc)nO(CRcRc)nC6-8aryl, —(CRcRc)nC3-8cycloalkyl, —(CRcRc)nC4-8heterocycloalkyl, —(CRcCRc)nO(CRcCRc)nCF3, —(CRcCRc)nN(CRcRc)nORa, —(CRcRc)nN(Ra)(CRcRc)nC6-8aryl, —(CRcRc)nN(Ra)(CRcRc)nC5-8heteroaryl, —(CRcRc)nO(CRcRc)nC5-8heteroaryl, —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl, wherein C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C6-8aryl, C4-8heterocycloalkyl, C3-8cycloalkyl or C5-8heteroaryl are substituted by 0, 1, 2 or 3 substituents independently selected from C1-4haloalkyl, halo, oxo, C1-6alkyl, cyano, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —N(Ra)(CRaRa)n—Y, —(CRaRa)nY, —(CRaRa)nC3-8cycloalkyl, or —(CRaRa)nORa;
Q is
R2 is methyl or ethyl;
Z5 is N;
Z9 is N;
Z10 is CR;
and the group NRaRa, either alone or a part of a larger group, can be a 4 to 6 membered heterocyclic ring wherein the two Ras taken together with the nitrogen atom to which they are attached form a ring that can have from zero to one additional heteroatom selected from N, O or S, and the ring can be substituted or unsubstituted with from 1 to 3 substitutents independently selected from oxo, halo, —CN, nitro, —C(═O)Rc, —C(═O)ORc, —ORc, —OC(═O)Rc, —SRc, —S(═O)Rc, —S(═O)2Rc, —S(═O)2NRcRc, —NRcRc, —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl.

### Claim 2

A compound of Formula I, or a pharmaceutically acceptable salt thereof,
wherein Ar1 is a 5 to 10 membered monocyclic or bicyclic ring that can contain from zero to four heteroatoms independently selected from O, N or S, and which ring can be unsubstituted or substituted with groups independently selected from C1-4haloalkyl, halo, —CN, nitro, —C(═O)NRaRa, —C(═O)Rb, —C(═O)ORb, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa,
—O—C1-6alkylN(Ra)C(═O)ORb, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl, wherein C1-6alkyl, C2-6alkenyl, or C2-6alkynyl are substituted by 0, 1, 2 or 3 substituents independently selected from C1-4haloalkyl, halo, cyano, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —N(Ra)(CRaRa)n—Y, —(CRaRa)nY, or —(CRaRa)nORa;
Y is a saturated, partially saturated or unsaturated 5-, 6- or 7-membered monocyclic ring or 6-, 7-, 8-, 9-, or 10-membered bicyclic ring containing 0, 1, 2, 3 or 4 heteroatoms independently selected from N, O and S, which is substituted with 0, 1, or 2 substitutents independently selected from C1-8alkyl, C2-6alkenyl, C2-6alkynyl, C1-4haloalkyl, halo, —CN, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa or —NRaC2-6alkylORa;
each Ra is independently hydrogen or Rb;
each Rb is independently phenyl, benzyl, C1-6alkyl or C3-8cycloalkyl, wherein the phenyl, benzyl, C1-6alkyl or C3-8cycloalkyl is substituted by 0, 1, 2 or 3 substituents independently selected from halo, C1-4alkyl, C1-3haloalkyl, —OC1-4alkyl, —NH2, —CN, or —NRaRa;
each Rc is independently hydrogen or C1-6alkyl;
each n is independently 0, 1, 2, or 3;
one of Z1, Z2, Z3 or Z4 is N and the others are CR;
each R is independently selected from hydrogen C1-4haloalkyl, halo, —CN, nitro, —C(═O)NRaRa, —C(═O)Rb, —C(═O)ORb, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —O—C1-6alkylN(Ra)C(═O)ORb, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —(CRcRc)nNRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —(CRcRc)nC3-8heterocycloalkyl, —(CRcRc)nC6-8aryl, —(CRcRc)nC5-8heteroaryl, —(CRcRc)nO(CRcRc)nC5-8heteroaryl, —C1-6alkyl —C2-6alkynyl, or —C2-6alkynyl, wherein —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl, —C3-8heterocycloalkyl, C6-8aryl or C5-8heteroaryl are substituted by 0, 1, 2 or 3 substituents independently selected from C1-4haloalkyl, halo, cyano, nitro, —C(═O)Rb, —C(═O)ORb, —C(═O)NRaRa, —C(═NRa)NRaRa, —ORa, —OC(═O)Rb, —OC(═O)NRaRa, —OC(═O)N(Ra)S(═O)2Rb, —OC2-6alkylNRaRa, —OC2-6alkylORa, —SRa, —S(═O)Rb, —S(═O)2Rb, —S(═O)2NRaRa, —S(═O)2N(Ra)C(═O)Rb, —S(═O)2N(Ra)C(═O)ORb, —S(═O)2N(Ra)C(═O)NRaRa, —NRaRa, —N(Ra)C(═O)Rb, —N(Ra)C(═O)ORb, —N(Ra)C(═O)NRaRa, —N(Ra)C(═NRa)NRaRa, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)2NRaRa, —NRaC2-6alkylNRaRa, —NRaC2-6alkylORa, —N(Ra)(CRaRa)n—Y, —(CRaRa)nY, or —(CRaRa)nORa;
Q is
R2 is methyl or ethyl;
Z5 is N;
Z9 is N;
Z10 is CR;
and the group NRaRa either alone or a part of a larger group, can be a 4 to 6 membered heterocyclic ring wherein the two Ras taken together with the nitrogen atom to which they are attached form a ring that can have from zero to one additional heteroatom selected from N, O or S, and the ring can be substituted or unsubstituted with from 1 to 3 substitutents independently selected from oxo, halo, —CN nitro, —C(═O)Rc, —C(═O)ORc, —ORc, —OC(O)Rc, —SRc, —S(═O)Rc, —S(═O)2Rc, —S(═O)2NRcRc, —NRcRc, —C1-6alkyl, —C2-6alkenyl, or —C2-6alkynyl.

### Claim 3 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is

### Claim 4 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is

### Claim 5 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z1 is N; and Z2, Z3 and Z4 are CR.

### Claim 6 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z1 is N; and Z2, Z3 and Z4 are CH.

### Claim 7 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z1, Z2 and Z4 are CR; and Z3 is N.

### Claim 8 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z1 is N; Z2 and Z4 are CH; and Z3 is CR.

### Claim 9 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Z1 is N; Z2 and Z4 are CH; Z3 is CR; and R is selected from hydrogen, C1-6alkyl, C1-6substituted alkyl, halo, C1-4haloalkyl, —(CRcRc)nC4-8heterocycloalkyl, —(CRcRc)nO(CRcRc)nC6-8aryl, —(CRcRc)nN(Ra)(CRcRc)nC6-8aryl, —(CRcRc)nN(Ra)(CRcRc)nC5-8heteroaryl, —(CRcRc)nsubstituted C4-8heterocycloalkyl, —(CRcRc)nO(CRcRc)nsubstitutedC6-8arcyl, —(CRcRc)nN(Ra)(CRcRc)nsubstitutedC6-8aryl, —(CRcRc)nN(Ra)(CRcRc)nsubstitutedC5-8heteroaryl, C2-6alkenyl, or —(CRcRc)nNRaRa.

### Claim 10 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Art is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl or indazolyl, which can be unsubstituted or substituted.

### Claim 11 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl or indazolyl, which can be unsubstituted or substituted with groups selected from —ORa, halo, —NRaRa, C1-4haloalkyl, —N(Ra)C(═O)Rb, or —N(Ra)C(═O)NRaRa.

### Claim 12 (depends on 1, 2)

A compound of in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CR; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl or indazolyl, which can be unsubstituted or substituted.

### Claim 13 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CH; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl or indazolyl, which can be unsubstituted or substituted.

### Claim 14 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein R2 is methyl.

### Claim 15 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CR; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl or indazolyl, which can be unsubstituted or substituted.

### Claim 16 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N;
Z2 and Z4 are CH;
Ar1 is substituted pyridyl; and
Z3 is CR.

### Claim 17 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl, indazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, or benzothiadiazolyl, which can be unsubstituted or substituted.

### Claim 18 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl, indazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, or benzothiadiazolyl, which can be unsubstituted or substituted with groups selected from —ORa, halo, —NRaRa, C1-4haloalkyl, —N(Ra)C(═O)Rb, —N(Ra)S(═O)2Rb, —N(Ra)S(═O)NRaRa or —N(Ra)C(═O)NRaRa.

### Claim 19 (depends on 1, 2)

A compound of in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CR; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl, indazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, or benzothiadiazolyl.

### Claim 20 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CH; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl, indazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, or benzothiadiazolyl.

### Claim 21 (depends on 1, 2)

A compound in accordance with claim 1 or 2, or a pharmaceutically acceptable salt thereof, wherein Q is
Z1 is N; and Z2, Z3 and Z4 are CR; and
Ar1 is selected from pyrazolyl, indolyl, phenyl, pyridyl, pyrimidinyl, benzoxazolyl, indazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, or benzothiadiazolyl, which can be unsubstituted or substituted.

### Claim 22

A compound, or a pharmaceutically acceptable salt thereof, selected from:
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-1H-indol-4-amine;
3-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)phenol;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)-1H-indazol-4-amine;
4-(2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
3-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-ylamino)phenol;
4-(2-(6-methoxypyridin-3-ylamino)-5-methylpyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
methyl-6-(5-methyl-2-(pyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine;
4-(5-methoxy-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(6-methoxypyridin-3-yl)-3-(4-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-amine;
4-(2-(6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-1H-indazol-4-amine;
4-methyl-6-(5-((4-(methylsulfonyl)piperazin-1-yl)methyl)-2-(6-(trifluoromethyl)pyridin-3-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine;
4-methyl-6-(5-((4-(methylsulfonyl)piperazin-1-yl)methyl)-2-(pyrimidin-5-ylamino)pyridin-3-yl)-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)benzo[d]oxazol-6-amine;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-methoxypyridin-3-ylamino)-5-(piperazin-1-ylmethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-methoxypyridin-3-ylamino)-5-(morpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methylpyridin-2-yl)-1H-indol-4-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methylpyridine-2-yl)-1H-indazol-4-amine;
4-(5-bromo-2-(4-methoxyphenylamino)pyridine-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-ethoxypyridin-3-ylamino)pyridine-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-yl)pyridine-2,5-diamine;
4-(2-(6-chloropyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine.

### Claim 23

A compound, or a pharmaceutically acceptable salt thereof selected from:
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-1,3-benzoxazol-5-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(4-morpholinylmethyl)-2-pyridinyl)-1,3-benzothiazol-5-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylmethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-(methylsulfonyl)benzyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(4-(methylsulfonyl)benzyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-(4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((1S)-1-(4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((1R)-1-(4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-(4-(methylsulfonyl)phenyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(1-(4-(methylsulfonyl)phenyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-morpholinylcarbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)carbonyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(2-methoxyethyl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinecarboxamide;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-morpholinone;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((1-(methylsulfonyl)-4-piperidinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-benzyl-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((4-methyl-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(((2R)-2-methyl-4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-N,N-dimethyl-1-piperazinecarboxamide;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-hydroxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-N,N-dimethyl-1-piperazinecarboxamide;
5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)amino)-3-fluoro-2-pyridinol;
4-(2-((5-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-N,6-dimethyl-1,3,5-triazin-2-amine;
4-(2-((3-(difluoromethoxy)phenyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)-2-methyl-1,3-benzoxazol-5-amine;
4-(2-((3-fluoro-4-methoxyphenyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((4-fluoro-3-methoxyphenyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((2,2-difluoro-1,3-benzodioxol-5-yl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6′-methoxy-N-(6-methoxy-3-pyridinyl)-3,3′-bipyridin-6-amine;
4-(2-((3,4-dimethoxyphenyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)-2-methyl-6-quinolinamine;
5′-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxy-3-pyridinyl)-2,3′-bipyridin-6′-amine;
4-(2-((5-chloro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-methyl-6-(2-((5-methyl-3-pyridinyl)amino)-3-pyridinyl)-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(5-fluoro-6-methoxy-3-pyridinyl)-2,4′-bipyridin-6-amine;
1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)carbonyl)-4-piperidinol;
6-(2-((6-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-2-methyl-4-pyrimidinamine;
(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methanol;
3-(6-amino-2-methyl-4-pyrimidinyl)-N-1H-indazol-4-yl-2-quinoxalinamine;
N-(2-chloro-4-((3-(2-methyl-9H-purin-6-yl)-2-pyridinyl)amino)phenyl)acetamide;
N-(4-((3-(2-methyl-9H-purin-6-yl)-2-pyridinyl)amino)phenyl)cyclopropanecarboxamide;
N-(5-methoxy-3-pyridinyl)-3-(2-methyl-9H-purin-6-yl)-2-pyridinamine;
4-(5-chloro-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-fluoro-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-fluoro-2-((5-fluoro-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinecarbaldehyde;
4-(5-chloro-2-(tetrahydro-2H-pyran-4-ylamino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-chloro-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-N-(2-methoxyethyl)-6-methyl-1,3,5-triazin-2-amine;
1-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-2-pyridinyl)-3-phenylurea;
1-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-2-pyridinyl)-3-(3-fluorophenyl)urea;
1-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-2-pyridinyl)-3-(1-methylethyl)urea;
N-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-pyridinyl)acetamide;
methyl (5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-pyridinyl)carbamate;
1-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-pyridinyl)-3-(4-(2-methoxyethoxy)phenyl)urea;
N-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)amino)-2-pyridinyl)acetamide;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-6-methyl-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-6-(4-morpholinylmethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-6-((2,2,2-trifluoroethoxy)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-3-pyridinyl)amino)-6-methyl-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-thiomorpholinylmethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((1-oxido-4-thiomorpholinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-amine;
((3S)-1-(6-((6-methoxy-3-pyridinyl)amino)-5-(2-methyl-9H-purin-6-yl)-3-pyridinyl)-3-pyrrolidinyl)methanol;
(3S)-1-(6-((6-methoxy-3-pyridinyl)amino)-5-(2-methyl-9H-purin-6-yl)-3-pyridinyl)-3-pyrrolidinol;
(3R)-1-(6-((6-methoxy-3-pyridinyl)amino)-5-(2-methyl-9H-purin-6-yl)-3-pyridinyl)-3-pyrrolidinol;
4-(2-((2-methoxy-5-pyrimidinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-N,N-dimethyl-1-piperazinesulfonamide;
1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-4-piperidinol;
((3R)-1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-pyrrolidinyl)methanol;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(((3S)-3-methyl-4-morpholinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-(1-azetidinylmethyl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-pyrrolidinylmethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-piperidinylmethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((3-(methylsulfonyl)-1-azetidinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperidinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
2-(((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)amino)ethanol;
(2R)-2-(((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)amino)-1-propanol;
4-(5-(((2-methoxyethyl)amino)methyl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(((3R, S)-3-(methylsulfonyl)-1-pyrrolidinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-azetidinol;
2-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-2,5,7-triazaspiro[3.4]octane-6,8-dione;
4-(5-((3-amino-1-azetidinyl)methyl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
N-(1-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-3-azetidinyl)methanesulfonamide;
4-(5-(5,6-dihydro[1,2,4]triazolo[1,5-a]pyrazin-7(8H)-ylmethyl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
2-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)(hydroxy)methyl)-4-bromo-N,N-dimethylbenzenesulfonamide;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide;
4-(amino(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)methyl)-N,N-dimethylbenzenesulfonamide;
3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxy-3-pyridinyl)-2-quinolinamine;
4-(2-((6-methoxy-3-pyridinyl)amino)phenyl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-1,3-benzothiazol-5-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-1,3-benzothiazol-6-amine;
4-(2-((5-fluoro-3-pyridinyl)amino)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-methyl-6-(5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-(1H-pyrazol-4-ylamino)-3-pyridinyl)-1,3,5-triazin-2-amine;
4-methyl-6-(5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-(1H-pyrazol-3-ylamino)-3-pyridinyl)-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-6-fluoro-1H-indazol-4-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-methyl-1H-pyrazol-4-yl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((3,4-difluorophenyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxy-3-pyridinyl)-1′,2′,3′,6′-tetrahydro-3,4′-bipyridin-6-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1H-pyrazol-4-yl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxy-3-pyridinyl)-6′-methyl-3,3′-bipyridin-6-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(4-pyridazinyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5′-fluoro-N-(6-methoxy-3-pyridinyl)-3,3′-bipyridin-6-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(6-methoxy-3-pyridinyl)-2,3′-bipyridin-6-amine;
5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-N-(5-fluoro-6-methoxy-3-pyridinyl)-2,3′-bipyridin-6-amine;
4-(5-(3,6-dihydro-2H-pyran-4-yl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-chloro-2-((5-fluoro-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-3-pyridinyl)amino)-5-(1-methyl-1H-pyrazol-4-yl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-6-(2-methoxyethoxy)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)-1H-benzimidazol-5-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-piperazinylmethyl)-2-pyridinyl)-1H-benzimidazol-5-amine;
4-(5-(difluoromethoxy)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-2(H)-pyridinone;
N-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-4-fluorobenzenesulfonamide;
N5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-2-pyridinyl)-2-chloro-3,5-pyridinediamine;
N-(4-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-fluorophenyl)acetamide;
N-(4-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)amino)-2-fluorophenyl)acetamide;
N-(4-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)-1-piperazinyl)methyl)-2-pyridinyl)amino)phenyl)acetamide;
(1R,S)-1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-2,2,2-trifluoroethanol;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(((2S)-2-methyl-4-(methylsulfonyl)-1-piperazinyl)methyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((1R)-1-((2S)-2-methyl-4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((1S)-1-((2S)-2-methyl-4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-2-propanol;
6-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((1S)-1-(4-morpholinyl)ethyl)-3-pyridinyl)-2-methyl-4-pyrimidinamine;
6-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-((1R)-1-(4-morpholinyl)ethyl)-3-pyridinyl)-2-methyl-4-pyrimidinamine;
4-(5-(1-amino-1-methylethyl)-2-((6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-(1-amino-1-methylethyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-methyl-1-(4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(1-methyl-1-(4-(methylsulfonyl)-1-piperazinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-5-(1-methyl-1-(4-morpholinyl)ethyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-((6-methoxy-3-pyridinyl)amino)-5-(1-(4-(methylsulfonyl)-1-piperazinyl)cyclopropyl)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine.

### Claim 24

A compound, or a pharmaceutically acceptable salt thereof, selected from:
(R)—N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-2-yl)-5-fluoroquinolin-7-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-yl)benzo[d]thiazol-5-amine;
4-(1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(benzo[d]thiazol-5-ylamino)pyridin-3-yl)ethyl)-N,N-dimethylpiperazine-1-carboxamide;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-2-yl)benzo[d]thiazol-5-amine;
(R)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-morpholinoethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(S)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-morpholinoethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((R)-1-((S)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-2-yl)benzo[d]thiazol-5-amine;
4-(1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethyl)-N,N-dimethylpiperazine-1-carboxamide;
1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)cyclopropanol;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(1-(isopropylamino)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-(1-aminocyclopropyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-(3-aminopentan-3-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)-4-(2-(5-isopropyl-6-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(5-(ethylsulfonyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-methoxypyridin-3-ylamino)-5-(1-(3-(methylsulfonyl)azetidin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)-4-(2-(6-chloropyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)—N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-2-yl)quinolin-7-amine 2,2,2-trifluoroacetate;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-methylpropan-1-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)propan-1-ol;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((4-(methylsulfonyl)-2-(trifluoromethyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanolexample;
(S)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((3-methylmorpholino)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(S)-4-(2-(6-chloro-5-methoxypyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(S)-4-(2-(6-chloropyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(S)-4-(2-(2-methoxypyrimidin-5-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-1,1,1-trifluoropropan-2-ol;
4-(2-(6-methoxypyridin-3-ylamino)-5-(2,2,2-trifluoro-1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)-1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanol;
(S)-1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethanol;
4-(5-(1-amino-2,2,2-trifluoroethyl)-2-(6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(2,2,2-trifluoro-1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)isoquinolin-7-amine;
4-(5-(1-aminoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(tetrahydro-2H-pyran-4-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)-2-methoxypyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
N′-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxy-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
N′-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(4-morpholinylmethyl)-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-ylamino)-2-chloropyridin-3-yl)morpholine-4-sulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-methoxypyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-ylamino)-2-methoxypyridin-3-yl)methanesulfonamide;
N′-(2-chloro-5-((3-(2-methyl-9H-purin-6-yl)-5-(1-(4-morpholinyl)ethyl)-2-pyridinyl)amino)-3-pyridinyl)-n,n-dimethylsulfamide;
(R)-4-(2-(6-chloro-5-methoxypyridin-3-ylamino)-5-(1-(4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-chloro-5-methoxypyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
4-(5-(3,6-dihydro-2H-pyran-4-yl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-(tetrahydro-2H-pyran-4-yl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
2-(5-(6-amino-2-methylpyrimidin-4-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-methylpropanoic acid;
1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-methylpropane-1,2-diol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxy-5-(trifluoromethyl)pyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5,6-dimethoxypyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
1-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2-hydroxy-2-methylpropyl 3-chlorobenzoate;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoropyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-methoxypyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxy-5-methylpyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-(methylsulfonyl)pyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
2-(5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-(phenylsulfonyl)pyridin-3-ylamino)pyridin-3-yl)propan-2-ol;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-N-isopropyl-N-methylpiperazine-1-carboxamide;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-N-methyl-N-(2,2,2-trifluoroethyl)piperazine-1-carboxamide;
4-((5-(4-amino-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3-yl)methyl)-N-cyclopropyl-N-methylpiperazine-1-carboxamide;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((R)-1-((R)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((S)-1-((R)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(2-methoxypyrimidin-5-ylamino)-5-((R)-1-((S)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
4-(2-(6-chloropyridin-3-ylamino)-5-((R)-1-((S)-2-methyl-4-(methylsulfonyl)piperazin-1-yl)ethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
(R)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((3-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)cyclopropanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)morpholine-4-sulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-N-isopropyl-N-methylaminosulfamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-methoxypyridin-2-yl)-2-chloropyridine-3,5-diamine;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-N,N-dimethylaminosulfamide;
(R)—N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
(S)—N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide;
(R)—N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-N,N-dimethylaminosulfamide;
(S)—N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(1-morpholinoethyl)pyridin-2-ylamino)-2-chloropyridin-3-yl)-N,N-dimethylaminosulfamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-methylpyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)pyridin-2-ylamino)-2-methylpyridin-3-yl)methanesulfonamide;
N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)-2-methylpyridin-3-yl)methanesulfonamide;
4-(5-((1,1-dioxidohexahydro-5h-isothiazolo[2,3-a]pyrazin-5-yl)methyl)-2-((5-fluoro-6-methoxy-3-pyridinyl)amino)-3-pyridinyl)-6-methyl-1,3,5-triazin-2-amine; or
N′-(5-((3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-chloro-2-pyridinyl)amino)-2-chloro-3-pyridinyl)-N,N-dimethylsulfamide.

### Claim 25 (depends on 1, 2, 22, 23, 24)

A pharmaceutical composition comprising: a compound in accordance with any one of claims 1, 2, 22, 23 or 24, or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable excipient.