# US 2014/0155379 A1 · Heterocycle amines and uses thereof

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- Number: US 2014/0155379 A1
- Document ID: US20140155379A1
- Status: Published application
- Kind: A1
- Application number: 14/137,318
- Filed: 2013-12-20
- Published: 2014-06-05
- Earliest claimed: 2010-11-19
- Assignees: Ligand Pharmaceuticals Incorporated
- Applicants: Ligand Pharmaceuticals Incorporated
- Inventors: Koc-Kan Ho; David Diller; Jeffrey J. Letourneau; Brian F. McGuinness; Andrew G. Cole; David Rosen; Cornelis A. van Oeveren; Jason C. Pickens; Lin Zhi; Yixing Shen; Bijan Pedram
- Web page: https://patentgrep.com/patent/US20140155379A1

## CPC

- C07D 513/04: Ortho-condensed systems
- A61K 31/407: condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
- A61K 31/4168: having a nitrogen attached in position 2, e.g. clonidine
- A61K 31/4353: ortho- or peri-condensed with heterocyclic ring systems
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/00: Drugs for immunological or allergic disorders
- C07D 235/02: condensed with carbocyclic rings or ring systems
- C07D 269/02: having the hetero atoms in positions 1 and 3
- C07D 277/42: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 277/60: condensed with carbocyclic rings or ring systems
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds and methods in the fields of chemistry and medicine are disclosed. Some of the disclosed embodiments include compounds, compositions and methods of using heterocycle amines. Some of the disclosed embodiments include heterocycle amines useful to treat inflammatory disorders.

## Claims

### Claim 1

A compound of Formula (I):
or a salt, ester, amide, or prodrug thereof,
wherein
is a single or double bond;
W is selected from CH, CH—CH, O, S, NR6, and CO;
Y is N or CR9;
Z is N or C, and Z is N if W is CH and Y is CR9;
R4 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted non-aromatic ring, an optionally substituted carbocycle, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, CO2R6, SO3R6, SO2R6 and SO2NR7R8;
R5 is selected from hydrogen, halogen, OR6, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 haloheteroalkyl, an optionally substituted C1-C6 alkenyl, and an optionally substituted C1-C6 alkynyl;
or R4 and R5 are linked to form an optionally substituted non-aromatic ring;
each R6 is independently selected from an optionally substituted aryl, an optionally substituted heteroaryl, and an optionally substituted non-aromatic ring, each optionally fused with a substituted aryl or a substituted heteroaryl, hydrogen, an optionally substituted C1-C10 alkyl, an optionally substituted C1-C10 haloalkyl, and an optionally substituted C1-C10 heteroalkyl;
each R7 and R8 is independently selected from an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted non-aromatic ring, each optionally fused with a substituted aryl or a substituted heteroaryl, hydrogen, an optionally substituted C1-C10 alkyl, an optionally substituted C1-C10 haloalkyl, an optionally substituted C1-C10 alkenyl, an optionally substituted C1-C10 alkynyl, and an optionally substituted C1-C10 heteroalkyl, or R7 and R8 are linked to form an optionally substituted non-aromatic ring;
R9 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted non-aromatic ring, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, CO2R6, SO3R6, and SO2NR7R8;
A is an optionally substituted aryl or an optionally substituted heteroaryl group;
each optionally substituted group is either unsubstituted or substituted with one or more groups independently selected from alkyl, heteroalkyl, alkenyl, alkynyl, haloalkyl, heterohaloalkyl, aryl, arylalkyl, heteroaryl, non-aromatic ring, hydroxy, alkoxy, aryloxy, mercapto, alkylthio, arylthio, cyano, halo, carbonyl, thiocarbonyl, O-carbamyl, N-carbamyl, O-thiocarbamyl, N-thiocarbamyl, C-amido, N-amido, S-sulfonamido, N-sulfonamido, C-carboxy, O-carboxy, isocyanato, thiocyanato, isothiocyanato, nitro, silyl, trihalomethanesulfonyl, ═O, ═S, amino, and protected derivatives of amino groups.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R4 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted non-aromatic ring, an optionally substituted carbocycle, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, CO2R6, SO3R6, SO2R6 and SO2NR7R8

### Claim 3 (depends on 1)

The compound of claim 1, wherein if R4 is pyrazolyl, the pyrazolyl is not substituted with aryl or heteroaryl groups.

### Claim 4 (depends on 1)

The compound of claim 1, wherein if R4 is oxazolyl, isoxazolyl, or imidazoyl, the oxazolyl, isoxazolyl, or imidazoyl radical is not substituted with aryl or heteroaryl groups.

### Claim 5 (depends on 1)

The compound of claim 1, represented by Formula (I-A):
or a salt, ester, amide, or prodrug thereof,
wherein
X is N or CR5′, wherein R5′ is selected from hydrogen, halogen, OR6, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 haloheteroalkyl, an optionally substituted C1-C6 alkenyl, and an optionally substituted C1-C6 alkynyl;
R1 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, CH2NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, an optionally substituted C1-C6 heteroalkyl, CO2R6, CONR7R8, SO3R6, and SO2NR7R8;
R2 and R3 are independently selected from hydrogen, halogen, OR6, NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, and an optionally substituted C1-C6 heteroalkyl.

### Claim 6 (depends on 1)

The compound of claim 1, represented by Formula (II):
or a salt, ester, amide, or prodrug thereof.

### Claim 7 (depends on 1)

The compound of claim 1, represented by Formula (III):
or a salt, ester, amide, or prodrug thereof,
wherein
X is N or CR5′, wherein R5′ is selected from hydrogen, halogen, OR6, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 haloheteroalkyl, an optionally substituted C1-C6 alkenyl, and an optionally substituted C1-C6 alkynyl;
R1 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, CH2NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, an optionally substituted C1-C6 heteroalkyl, CO2R6, CONR7R8, SO3R6, and SO2NR7R8;
R2 and R3 are independently selected from hydrogen, halogen, OR6, NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, and an optionally substituted C1-C6 heteroalkyl.

### Claim 8 (depends on 1, 2, 3, 4, 5, 6, 7)

The compound of any of claims 1-7, wherein W is S.

### Claim 9 (depends on 7, 8)

The compound of claim 7 or 8, wherein X is N.

### Claim 10 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein Y is CR9.

### Claim 11 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10)

The compound of any one of claims 1-10, wherein R4 is selected from the group consisting of pyridyl, pyrazolyl, cyano, triazolyl, and oxazolyl.

### Claim 12 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9)

The compound of any one of claims 1-9, wherein Y is N.

### Claim 13 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 12)

The compound of any one of claims 1-9 and 12, wherein R4 is selected from the group consisting of pyridyl, pyrazolyl, pyrimidinyl, pyridazinyl, and C1-C6 alkyl.

### Claim 14 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of:
N-(4-(hydroxymethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(1H-pyrazol-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(piperazin-1-ylmethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
1-(4-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
1-(4-methylpiperazin-1-yl)-2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)ethanone,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
5-(1H-pyrazol-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-morpholinopyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-morpholinopyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methanol,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((dimethylamino)methyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(isopropoxymethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2-methoxy-1-(4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2-methoxy-1-(4-((2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
2-methoxy-1-(4-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(isopropoxymethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(isopropoxymethyl)-pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(isopropoxymethyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(1H-pyrazol-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(isopropylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(isopropylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2-methoxy-1-(4-(2-((5-(pyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-amine,
2-((6-methyl-4-(pyrrolidin-3-ylamino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-6-(4H-1,2,4-triazol-4-yl)benzo[d]thiazol-2-amine,
2-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((tetrahydro-2H-pyran-4-yl)oxy)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridazin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
1-(4-(2-((5-ethylthiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-methoxyethanone,
1-((2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-2-one,
1-((2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-2-one,
2-methoxy-1-(4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperidin-1-yl)ethanone,
N2-(benzo[d]thiazol-2-yl)-N4-(bicyclo[2.2.1]heptan-2-yl)-N6—((R)-pyrrolidin-3-yl)-1,3,5-triazine-2,4,6-triamine,
N2-(bicyclo[2.2.1]heptan-2-yl)-N4-(6-methoxybenzo[d]thiazol-2-yl)-N6-(pyrrolidin-3-yl)-1,3,5-triazine-2,4,6-triamine,
N2-(bicyclo[2.2.1]heptan-2-yl)-N4-(6-chloro benzo[d]thiazol-2-yl)-N6-(pyrrolidin-3-yl)-1,3,5-triazine-2,4,6-triamine,
2-((4-(bicyclo[2.2.1]heptan-2-ylamino)-6-(pyrrolidin-3-ylamino)-1,3,5-triazin-2-yl)amino)benzo[d]thiazole-6-carboxylic acid,
N2-(benzo[d]thiazol-2-yl)-N4-((1R,4S)-bicyclo[2.2.1]heptan-2-yl)-N6—((R)-pyrrolidin-3-yl)pyrimidine-2,4,6-triamine,
2-((6-methoxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-chlorobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2((2-((4-(methylamino)-6-(pyrrolidin-3-ylamino)-1,3,5-triazin-2-yl)amino)benzo[d]thiazol-6-yl)oxy)ethanol,
(S)-2-((6-methoxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-chlorobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2-((6-chlorobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
N-(2-aminoethyl)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)isonicotinamide,
N-(4-aminobutyl)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)isonicotinamide,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-ylmethyl)isonicotinamide,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(piperidin-3-isonicotinamide,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-2-ylmethyl)isonicotinamide,
2-((4-(3-aminopiperidine-1-carbonyl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
N2-(6-methoxybenzo[d]thiazol-2-yl)-N4-(pyrrolidin-3-yl)pyridine-2,4-diamine,
N2-(6-chlorobenzo[d]thiazol-2-yl)-N4-(pyrrolidin-3-yl)pyridine-2,4-diamine,
(S)-2-((6-bromobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)-N-methyl-N-(pyrrolidin-3-yl)isonicotinamide,
2((4-(pyrrolidin-3-ylamino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
(S)-2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-(pyridin-3-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-(1-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((7-methoxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
6-bromo-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
(S)-2-((6-cyanobenzo[d]thiazol-2-yl)amino)-6-methyl-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((7-cyanobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((4-(cyclo pentylamino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
1-(4-((2-((6-bromobenzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
1-(4-((2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
N-(4-(piperidin-1-ylmethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
2-((5-methyl-4-(pyrrolidin-3-ylamino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
6-(pyridin-3-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
1-((2-((6-bromobenzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperidin-4-ol,
2-(((2-((6-bromobenzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)(methyl)amino)ethanol,
6-bromo-N-(4-((dimethylamino)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)picolinamide,
6-(1H-pyrazol-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
2-((4-((2-aminopropyl)amino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-((1-aminopropan-2-yl)amino)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
N-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)methanesulfonamide,
N-(4-(piperidin-1-ylmethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-((dimethylamino)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
4-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)picolinamide,
6-(6-methoxypyridin-3-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(pyrimidin-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(2-methylpyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)acetic acid,
1,1-dimethyl-3-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)urea,
6-(3-methoxypyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(2-methoxypyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(2-chloropyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(3-methylpyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
2-(2((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)-N-(2-(pyrrolidin-1-yl)ethyl)acetamide,
N-(4-((methylamino)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
3-(2-((4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)amino)benzo[d]thiazol-6-yl)benzonitrile,
N-(4-morpholinopyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(2-methoxypyrimidin-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
3-(piperidin-1-yl)-N-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)propanamide,
6-(benzo[c][1,2,5]oxadiazol-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
1-methyl-4-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)piperazin-2-one,
2-(4-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanol,
N-methyl-4-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazine-1-carboxamide,
methyl 2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)acetate,
2-(methyl(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)amino)ethanol,
1-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-3-ol,
N-(4-((4-methylpiperazin-1-yl)methyl)pyridin-2-yl)-6-(pyrimidin-5-yl)benzo[d]thiazol-2-amine,
2-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)amino)ethanol,
7-methyl-6-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
5-methyl-6-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(2-aminopyrimidin-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
2-(2((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)-1-(pyrrolidin-1-yl)ethanone,
N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)pyridin-4-yl)benzo[d]thiazol-2-amine,
1-methyl-N-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)pyrrolidine-2-carboxamide,
5-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(pyrimidin-5-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(aminomethyl)pyridin-2-yl)-6-(pyrimidin-5-yl)benzo[d]thiazol-2-amine,
N-methyl-2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)acetamide,
N-(2-hydroxyethyl)-2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)acetamide,
N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-6-(1H-1,2,4-triazol-1-yl)benzo[d]thiazol-2-amine,
1-(3-hydroxypyrrolidin-1-yl)-2-(2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)ethanone,
N-((2-((6-(pyrimidin-5-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)methanesulfonamide,
N-(4-morpholinopyridin-2-yl)-6-(4H-1,2,4-triazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)-6-(4H-1,2,4-triazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(piperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(piperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
6-(1H-imidazol-1-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-morpholino pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(pyrrolidin-3-ylamino)pyridin-2-yl)-6-cyanobenzo[d]thiazol-2-amine,
N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-morpholinopyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(piperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(pyridazin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-((methylamino)methyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((dimethylamino)methyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(pyrazin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(azetidin-1-ylmethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-benzylpiperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(2-((4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)amino)thiazolo[5,4-b]pyridin-5-yl)pyrimidine-2-carbonitrile,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-(dimethylamino)ethanone,
2-hydroxy-N-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)acetamide,
2-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanol,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-methoxyethanone,
5-(2-((4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)amino)benzo[d]thiaz ol-6-yl)pyrimidine-2-carbonitrile,
(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methanol,
N2-(6-(pyridin-4-yl)benzo[d]thiazol-2-yl)pyridine-2,6-diamine,
6-(1H-pyrrol-3-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-hydroxyethanone,
N-(4-((methylamino)methyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(aminomethyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
1-(2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)ethanol,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2-(2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-ylpropan-2-ol,
N-(4-(methoxymethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-3-(dimethylamino)propan-1-one,
(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)-3-fluoropyridin-4-yl)methanol,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-3-(pyrrolidin-1-yl)propan-1-one,
N-(4-((dimethylamino)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-((methylamino)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(aminomethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(piperidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(morpholinomethyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-((dimethylamino)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(piperidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(isoindolin-2-ylmethyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(morpholino methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(aminomethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((methylamino)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(azepan-1-ylmethyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(((1S,4R)-bicyclo[2.2.1]heptan-2-ylamino)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((3-phenylpyrrolidin-1-yl)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(azepan-1-ylmethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(isoindolin-2-ylmethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
1-((2-((6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-3-ol,
N-(4-(azetidin-1-ylmethyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
1-((2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-3-ol,
N-(4-(azetidin-1-ylmethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-((3-phenylpyrrolidin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)methyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(aminomethyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((1S,4R)-2-azabicyclo[2.2.1]heptan-2-ylmethyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
2-methoxy-1-(4-(2-((6-(5-methyl-1H-pyrazol-4-yl) thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-((1S,4R)-2-azabicyclo[2.2.1]heptan-2-ylmethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(((1S,4R)-bicyclo[2.2.1]heptan-2-ylamino)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((3,3-dimethylpyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-((3,3-dimethylpyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
2-methoxy-1-(4-((2-((6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
6-(1H-pyrazol-4-yl)-N-(4-((pyridin-3-yloxy)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2-methoxy-1-(4-(2-((6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
2-methoxy-1-(4-((2-((6-(pyridin-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
1-(4-((2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)-2-methoxyethanone,
2-methoxy-1-(4-((2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
1-(4-((2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)-2-methoxyethanone,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
1-(4-((2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-methoxyethanone,
4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)-1-methylpiperazin-2-one,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4((4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
1-((2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)pyridin-4-yl)methyl)pyrrolidin-3-ol,
(R)-6-(5-methyl-1H-pyrazol-4-yl)-N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
(R)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
(R)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
(S)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(isopropoxymethyl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)-6-(5-methyl-1H-pyrazol-4-yl)-N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)benzo[d]thiaz ol-2-amine,
(R) —N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
(S)—N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
(R)—N-(4-((3-methoxypyrrolidin-1-yl)methyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
N-(4-((cyclopentyloxy)methyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
6-(1H-pyrazol-4-yl)-N-(4-(((tetrahydro-2H-pyran-4-yl)oxy)methyl)pyridin-2-yl)benzo[d]thiazol-2-amine,
(S)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-((2-methylpyrrolidin-1-yl)methyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(isopropoxymethyl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(pyridin-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(1-methoxypropan-2-yl)piperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
(S)—N-(4-(3-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(isopropylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
2,2-dimethyl-1-(4-(2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)propan-1-one,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine,
6-(pyridin-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
(S)-2-methoxy-1-(2-methyl-4-(2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(S)-2-methoxy-1-(2-methyl-4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(S)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(3-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-(4-(2-methoxyethyl)-3-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
6-(1H-pyrazol-4-yl)-N-(4-(4-(3,3,3-trifluoropropyl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
N-(4-(4-(2-isopropoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-(5-methyl-1H-pyrazol-4-yl)benzo[d]thiazol-2-amine,
(R)-2-methoxy-1-(3-methyl-4-(2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(R)—N-(4-(2-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-(4-(2-methoxyethyl)-3-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-(4-(2-methoxyethyl)-3-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-(4-(2-methoxy ethyl)-3-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
1-(4-(2-((5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-isopropoxyethanone,
2-isopropoxy-1-(4-(2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
2-isopropoxy-1-(4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(R)-2-methoxy-1-(3-methyl-4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(R)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(2-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)-2-methoxy-1-(2-methyl-4-(2-((5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(R)-2-methoxy-1-(2-methyl-4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
2-methoxy-1-(4-(2-((5-(2-methylpyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
(R)—N-(4-(3-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(3-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(2-methylpyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(2-methylpyridin-4-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
2-methoxy-1-(4-(2-((5-(pyridazin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridazin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-(4-(2-methoxyethyl)-2-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-(4-(2-methoxyethyl)-2-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(R)—N-(4-(4-(2-methoxyethyl)-2-methylpiperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperidin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperidin-1-yl)pyridin-2-yl)-5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N4-(2-methoxyethyl)-N4-methyl-N2-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)pyridine-2,4-diamine,
N-(4-((1S,4S)-5-(2-methoxyethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-5-(pyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperidin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N4-(2-methoxyethyl)-N4-methyl-N2-(5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)pyridine-2,4-diamine,
N2-(5-(1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)-N4-(2-methoxyethyl)-N4-methylpyridine-2,4-diamine,
(R)—N-(4-(4-(2-methoxyethyl)-2-methylpiperazin-1-yl)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)—N-(4-(2-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
(S)-5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(2-methyl-4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
2-((4-morpholinopyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-(pyrrolidine-1-carbonyl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
(2-((5-bromothiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)(pyrrolidin-1-yl)methanone,
N-(4-(cyclopentyloxy)pyridin-2-yl)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(cyclopentyloxy)pyridin-2-yl)-5-(5-methyl-1H-pyrazol-4-yl)thiazolo[5,4-b]pyridin-2-amine,
5-ethynyl-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-6-methylbenzo[d]thiazol-2-amine,
2-((4,6-dimethylpyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-(4-oxo piperidin-1-yl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]thiazol-6-amine,
6-isopropyl-N-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-yl)benzo[d]thiazol-2-amine,
2-((4-(4-hydroxypiperidin-1-yl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-(2-methoxyethoxy)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
2-((4-isobutoxypyridine-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)-5-vinylthiazolo[5,4-b]pyridin-2-amine,
5-ethyl-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
5-(pyridin-4-yl)-N-(4-((tetrahydro-2H-pyran-4-yl)oxy)pyridin-2-yl)thiazolo[5,4-[b]pyridin-2-amine,
N-(4-ethylpyridin-2-yl)-6-(1H-imidazol-4-yl)benzo[d]thiazol-2-amine,
1-(4-(2-((5-ethynylthiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)-2-methoxyethanone,
4-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)morpholin-3-one,
2-((4-ethylpyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
1,1-dimethyl-3-(2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)urea,
5-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
methyl (2-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)amino)pyridin-4-yl)carbamate,
2-((4-(hydroxymethyl)pyridin-2-yl)amino)benzo[d]thiazole-6-carbonitrile,
5-cyclopropyl-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)thiazolo[5,4-b]pyridin-2-amine,
N-(4-ethylpyridin-2-yl)-6-(oxazol-5-yl)benzo[d]thiazol-2-amine.
3-((5-trifluoromethylbenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)benzamide,
3-((6-nitrobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)benzamide,
2-(3-(pyrrolidin-1-ylmethyl)phenylamino)-6-cyanobenzo[d]thiazole,
(R)-2-(benzo[d]thiazol-2-ylamino)-4-(3-hydroxypropylamino)-6-(pyrrolidin-3-ylamino)-1,3,5-triazine,
(R)-2-(benzo[d]thiazol-2-ylamino)-4-(2-hydroxyethylamino)-6-(pyrrolidin-3-ylamino)-1,3,5-triazine,
(R)-2-(benzo[d]thiazol-2-ylamino)-4-methylamino-6-(pyrrolidin-3-ylamino)-1,3,5-triazine,
2-((6-fluorobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-hydroxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-trifluoromethylbenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-trifluoromethoxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-methoxybenzo[d]thiazol-2-yl)amino)-6-methyl-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-hydroxymethylbenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2-((6-methoxybenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-phenylbenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-methylsulfonylbenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((quinolin-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(S)-2-((6-cyanoquinoline-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2-((6-N-methyl-N-(2-methoxyethyl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
(R)-2((6-morpholinobenzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)-4-pyrimidinecarboxamide,
5-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)nicotinamide,
2-((6-bromobenzo[d]thiazol-2-yl)amino)-4-(N-methyl-N-(2-methoxyethyl)aminomethyl)pyridine,
2-((6-bromobenzo[d]thiazol-2-yl)amino)-4-(morpholinomethyl)pyridine,
2-((6-bromobenzo[d]thiazol-2-yl)amino)-4-(4-methylpiperazinomethyl)pyridine,
2-((6-(3,5-dimethylisoxazol-4-yl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(3-chloropyridin-4-yl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(3-methoxyphenyl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(3,5-dimethylpyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(2,2,2-trifluoroethyl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(2,2,2-trifluoro ethyl)benzo[d]thiazol-2-yl)amino)-4-(4-methoxyacetylpiperazin-1-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-cyano acetylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-cyanomethylpiperidin-4-yl)pyridine,
2-((6-(imidazol-1-yl)benzo[d]thiazol-2-yl)amino)-4-hydr oxy methylpyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-(4-methoxyphenyl)acetylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-(3-cyclopentyl-1-oxopropyl)piperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-(1-oxopropyl)piperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-cyclopropylcarbonylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-trifluoro acetylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-ethylsulfonylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-methoxyacetylpiperidin-4-yl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(piperidin-4-yl)pyridine,
2-((6-(pyrazol-1-yl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(3-fluoropyridin-4-yl)benzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-(pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-4-hydroxymethyl-3-fluoropyridine,
2-((6-bromobenzo[d]thiazol-2-yl)amino)-4-hydroxymethylpyridine,
2-((6-bromobenzo[d]thiazol-2-yl)amino)-4-ethylpyridine,
5-((6-cyanobenzo[d]thiazol-2-yl)amino)-3-methylisoxazole,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-5-methyl-4-phenylthiazole,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-5-(4-methoxyphenyl)-1,3,4-thiadiazol,
2-((6-(oxazol-5-yl)benzo[d]thiazol-2-yl)amino)-4-(4-(2-methoxyethyl)piperazin-1-yl)pyridine,
2-((6-(2-methyl-1,3,4-oxadiazol-5-yl)benzo[d]thiazol-2-yl)amino)-4-ethylpyridine,
2-(3-hydroxymethylphenyl)amino-6-cyanobenzo[d]thiazole,
2-((6-(1,3,4-oxadiazol-2-yl)benzo[d]thiazol-2-yl)amino)-4-ethylpyridine,
2-((6-(1,3,4-thiadiazol-2-yl)benzo[d]thiazol-2-yl)amino)-4-ethylpyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylmethyl)pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(pyrrolidin-1-ylthiocarbonyl)pyridine,
2-(3,5-dimethoxymethylphenyl)amino-6-cyanobenzo[d]thiazole,
4-((6-(1H-pyrazol-4-yl)benzo[d]thiazol-2-yl)amino)-N-(pyrrolidin-3-yl)-6-pyrimidinecarboxamide,
5-(5-methyl-1H-pyrazol-4-yl)-2-(4-hydroxymethylpyridin-2-ylamino)thiazolo[5,4-b]pyridine,
5-(pyridin-4-yl)-2-(5-isopropyloxymethylisoxazol-3-ylamino)thiazolo[5,4-b]pyridine,
5-(1H-pyrazol-4-yl)-2-(3-(4-methoxyacetylpiperazin-1-ylphenyl)amino)thiazolo[5,4-b]pyridine,
5-ethyl-2-(3-(4-methoxyacetylpiperazin-1-ylphenyl)amino)thiazolo[5,4-b]pyridine,
5-ethyl-2-(4-(1-methoxyacetylpiperidin-4-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-ethyl-2-(4-(pyrrolidon-1-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(pyridine-4-yl)-2-(4-(3-dimethylamino-3-oxopropyl)pyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(1-methylimidazol-5-yl)-2-(4-(4-methoxyacetylpiperazin-1-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(pyrimidin-4-yl)-2-(4-(4-methoxyacetylpiperazin-1-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(thiazol-5-yl)-2-(4-(4-methoxyacetylpiperazin-1-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-propyl-2-(4-(4-methoxyacetylpiperazin-1-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(1H-pyrazol-4-yl)-2-(2-pyrrolidon-1-ylmethylpyridin-4-yl)amino)thiazolo[5,4-b]pyridine,
5-(pyridin-4-yl)-2-(4-(1-methyl-2-oxopiperidin-4-ylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(1-methylimidazol-5-yl)-2-(4-(2-dimethylaminocarbonylethyl)pyridin-2-yl)amino)thiazolo[5,4-b]pyridine,
5-(pyridine-4-yl)-2-(4-(4-methoxyacetylpiperazin-1-ylpyridin-2-yl)amino)oxazolo[5,4-b]pyridine,
2-((6-cyanobenzo[d]thiazol-2-yl)amino)-4-(1-phenylcarbonylpiperidin-4-yl)pyridine,
6-cyano-2-(4-(4-methoxyacetyl-piperazin-1-yl)pyridin-2-ylamino)imidazo[1,2-a]pyridine,
6-cyano-2-(4-(4-(2-methoxyethyl)piperazin-1-yl)pyridin-2-ylamino)imidazo[1,2-a]pyridine,
6-(1H-pyrazol-4-yl)-2-(4-morpholinopyridin-2-ylamino)imidazo[1,2-a]pyridine, and
5-(pyridin-3-yl)-2-(4-(piperazin-1-ylmethylpyridin-2-yl)amino)thiazolo[5,4-b]pyridine.

### Claim 15 (depends on 1)

The compound of claim 1, represented by Formula (IV):
or a salt, ester, amide, or prodrug thereof,
wherein:
X is N or CR5′, wherein R5′ is selected from hydrogen, halogen, OR6, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 heteroalkyl, an optionally substituted C1-C6 haloheteroalkyl, an optionally substituted C1-C6 alkenyl, and an optionally substituted C1-C6 alkynyl;
R1 is selected from hydrogen, halogen, OR6, CN, NR7R8, CH2OR6, CH2NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, an optionally substituted C1-C6 heteroalkyl, CO2R6, CONR7R8, SO3R6, and SO2NR7R8; and
R2 and R3 are independently selected from hydrogen, halogen, OR6, NR7R8, an optionally substituted C1-C6 alkyl, an optionally substituted C1-C6 haloalkyl, an optionally substituted C1-C6 alkenyl, an optionally substituted C1-C6 alkynyl, and an optionally substituted C1-C6 heteroalkyl.

### Claim 16 (depends on 1, 15)

The compound of claim 15 or 1, wherein X is N.

### Claim 17 (depends on 15)

The compound of claim 15, wherein the compound is selected from the group consisting of:
6-(1H-pyrazol-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)imidazo[1,2-a]pyridin-2-amine,
2-((4-(hydroxymethyl)pyridin-2-yl)amino)imidazo[1,2-a]pyridine-6-carbonitrile,
(S)-tert-butyl 3-(2-((6-cyanoimidazo[1,2-a]pyridin-2-yl)amino)isonicotinamido)pyrrolidine-1-carboxylate,
(S)-2-((6-cyanoimidazo[1,2-a]pyridin-2-yl)amino)-N-(pyrrolidin-3-yl)isonicotinamide,
2((4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)amino)imidazo[1,2-a]pyridine-6-carbonitrile,
6-(pyridin-3-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)imidazo[1,2-a]pyridin-2-amine,
1-(4-((2-((6-(pyridin-4-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
1-(4-((2-((6-(pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
(2-((6-(pyridin-4-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methanol,
N-(4-(piperazin-1-ylmethyl)pyridin-2-yl)-6-(pyridin-4-yl)imidazo[1,2-a]pyridin-2-amine,
1-(4-((2-((6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methyl)piperazin-1-yl)ethanone,
N-(4-(piperazin-1-ylmethyl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine,
(2-((6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methanol,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-6-(pyridin-4-yl)imidazo[1,2-a]pyridin-2-amine,
2-methoxy-1-(4-(2-((6-(pyridin-4-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)piperazin-1-yl)ethanone,
N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine,
6-(5-methyl-1H-pyrazol-4-yl)-N-(4-(4-(methylsulfonyl)piperazin-1-yl)pyridin-2-yl)imidazo[1,2-a]pyridin-2-amine, and
(2-((6-(pyridin-3-yl)imidazo[1,2-a]pyridin-2-yl)amino)pyridin-4-yl)methanol.

### Claim 18 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)

A pharmaceutical composition comprising the compound of any one of claims 1-17 and a pharmaceutically acceptable carrier.

### Claim 19 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)

A method of treating a disorder responsive to inhibition of Interleukin-1 Receptor-Associated Kinase-mediated signal transduction comprising administering to a subject in need thereof an effective amount of the compound of any one of claims 1-17.

### Claim 20 (depends on 19)

The method of claim 19, wherein the disorder is an inflammatory disorder.

### Claim 21 (depends on 20)

The method of claim 20, wherein the inflammatory disorder is selected from the group consisting of osteoarthritis, rheumatoid arthritis, multiple sclerosis, corneal ulcers, uveitis, and inflammatory bowel disease.

### Claim 22 (depends on 19)

The method of claim 19, wherein the disorder is a skin disorder.

### Claim 23 (depends on 22)

The method of claim 22, wherein the skin disorder is selected from the group consisting of dermatitis, cutaneous eosinophilias, Lichen planus, urticaria, psoriasis, pruritus, angiodermas, chronic skin ulcers, conjunctivitis, vasculitides, and erythemas.

### Claim 24 (depends on 19)

The method of claim 19, wherein the disorder is a respiratory disorder.

### Claim 25 (depends on 24)

The method of claim 24, wherein the respiratory disorder is selected from the group consisting of asthma, rhinitis, chronic obstructive pulmonary disease, bronchitis, nasal polyposis, nasal congestion, farmer's lung, fibroid lung and cough.

### Claim 26 (depends on 19)

The method of claim 19, wherein the disorder is selected from the group consisting of diabetes, obesity, allergic disease, cancer, and sepsis.

### Claim 27 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)

Use of the compound of any one of claims 1-18 in the preparation of a medicament for treating a disorder responsive to inhibition of Interleukin-1 Receptor-Associated Kinase-mediated signal transduction.

### Claim 28 (depends on 27)

The use of claim 27, wherein the disorder is an inflammatory disorder.

### Claim 29 (depends on 28)

The use of claim 28, wherein the inflammatory disorder is selected from the group consisting of osteoarthritis, rheumatoid arthritis, multiple sclerosis, corneal ulcers, uveitis, and inflammatory bowel disease.

### Claim 30 (depends on 27)

The use of claim 27, wherein the disorder is a skin disorder.

### Claim 31 (depends on 30)

The use of claim 30, wherein the skin disorder is selected from the group consisting of dermatitis, cutaneous eosinophilias, Lichen planus, urticaria, psoriasis, pruritus, angiodermas, chronic skin ulcers, conjunctivitis, vasculitides, and erythemas.

### Claim 32 (depends on 27)

The use of claim 27, wherein the disorder is a respiratory disorder.

### Claim 33 (depends on 32)

The use of claim 32, wherein the respiratory disorder is selected from the group consisting of asthma, rhinitis, chronic obstructive pulmonary disease, bronchitis, nasal polyposis, nasal congestion, farmer's lung, fibroid lung and cough.

### Claim 34 (depends on 27)

The use of claim 27, wherein the disorder is selected from the group consisting of diabetes, obesity, allergic disease, cancer, and sepsis.

### Claim 35 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)

A compound of any one of claims 1-17 for treating a disorder responsive to inhibition of Interleukin-1 Receptor-Associated Kinase-mediated signal transduction.

### Claim 36 (depends on 35)

The compound of claim 35, wherein the disorder is an inflammatory disorder.

### Claim 37 (depends on 36)

The compound of claim 36, wherein the inflammatory disorder is selected from the group consisting of osteoarthritis, rheumatoid arthritis, multiple sclerosis, corneal ulcers, uveitis, and inflammatory bowel disease.

### Claim 38 (depends on 35)

The compound of claim 35, wherein the disorder is a skin disorder.

### Claim 39 (depends on 38)

The compound of claim 38, wherein the skin disorder is selected from the group consisting of dermatitis, cutaneous eosinophilias, Lichen planus, urticaria, psoriasis, pruritus, angiodermas, chronic skin ulcers, conjunctivitis, vasculitides, and erythemas.

### Claim 40 (depends on 35)

The compound of claim 35, wherein the disorder is a respiratory disorder.

### Claim 41 (depends on 40)

The compound of claim 40, wherein the respiratory disorder is selected from the group consisting of asthma, rhinitis, chronic obstructive pulmonary disease, bronchitis, nasal polyposis, nasal congestion, farmer's lung, fibroid lung and cough.

### Claim 42 (depends on 35)

The compound of claim 35, wherein the disorder is selected from the group consisting of diabetes, obesity, allergic disease, cancer, and sepsis.