# US 8,569,283 B2 · Compounds and compositions as c-Kit kinase inhibitors

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,569,283 B2
- Document ID: US8569283B2
- Status: Granted
- Kind: B2
- Application number: 13/598,213
- Filed: 2012-08-29
- Published: 2013-03-07
- Granted: 2013-10-29
- Earliest claimed: 2011-09-01
- Applicants: Valentina Molteni; Hank Michael James Petrassi; Xiaolin Li; Xiaodong Liu; Jon Loren; Juliet Nabakka; Bao Nguyen; Vince Yeh
- Inventors: Valentina Molteni; Hank Michael James Petrassi; Xiaolin Li; Xiaodong Liu; Jon Loren; Juliet Nabakka; Bao Nguyen; Vince Yeh
- Web page: https://patentgrep.com/patent/US8569283B2

## CPC

- C07D 491/107: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/02: Nasal agents, e.g. decongestants
- A61P 11/06: Antiasthmatics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/04: Antipruritics
- 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
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- C07D 491/044: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D 491/048: the oxygen-containing ring being five-membered
- C07D 498/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention provides compounds and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.

## Claims

### Claim 1

A compound of Formula (I) or Formula (II), or pharmaceutically acceptable salt thereof:
wherein:
m is 1 and R20 is selected from H, halo, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, deuterium, deuterated C1-C6alkyl, —CN, —(CR92)nOR4, —C(O)R4, —(CR92)nC(═O)OR4, R10, —(CR92)nR10, —((CR92)nO)tR4, —(CR92)nO(CR92)nR7, —(CR92)nC(═O)R4, —C(═O)N(R4)2, —OR4, and —(CR92)nCN;
or m is 4 and R20 is deuterium;
R1 is selected from C1-C6alkyl and halo;
each R11 is independently selected from H, halo and C1-C6alkyl;
L1 is a bond, —NH— or —C(O)NH—;
L2 is —(CR92)n—, —CHR6—, —(CR92)nO—, —NH—, —(CR92)nC(═O)—, —C(═O)O(CR92)n—, —(CR92)nOC(═O)NR4—, —(CR92)nNR4C(═O)(CR92)n—, —(CR92)nNR4C(═O)—, or —(CR92)nNR4C(═O)O—;
R2 is R3 or L2R3;
R3 is selected from an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a piperidinone, a oxazolidin-2-one, pyrrolidinone, a pyrrolidin-2-one and a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, wherein the substituted 4-6 membered heterocycloalkyl of R3 is substituted with 1-4 substituents independently selected from C1-C6alkyl halo, —CN, C1-C6haloalkyl, —OR4, —C(═O)OR4, —C(═O)R4, —C(═O)R7, —C(═O)OR5, —(CR92)nOR4, —C(CR92)nOR4, —C(═O)O(CR92)nOR4, —N(R4)2, —C(═O)NR42, —NR4C(═O)OR4, —NR4C(═O)(CR92)nOR4, —NR4(CR92)nOR4, —NR4S(═O)2R4, —N(C(═O)OR4)2, R8, —(CR92)nR8, deuterated C1-C6alkoxy, —S(═O)2R4, —S(═O)2R7, —S(═O)2R8, —S(═O)2N(R4)2, —S(═O)2NHC(═O)OR4, —S(═O)2(CR92)nC(═O)OR4, S(═O)2(CR92)nOR4, a spiro attached dioxolane, a spiro attached dioxolane which is substituted with C1-C6alkyl, a spiro attached dioxane, a spiro attached tetrahydrofuranly, a spiro attached oxetane, a spiro attached cyclobutanone, a spiro attached cyclobutanol, a C1 alkyl bridge, an unsubstituted 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S and a 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S substituted with 1-3 substituents independently selected from C1-C6alkyl, halo, C1-C6haloalkyl, C1-C6haloalkoxy, —OR4 and R8;
each R4 is independently selected from H and C1-C6alkyl;
R5 is an unsubstituted C3-C8cycloalkyl, an unsubstituted 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N or O or a C3-C8cycloalkyl substituted with 1-3 substituents independently selected from C1-C6alkyl;
each R6 is independently selected from —NR4C(O)OR4, —OR4 and —(CR92)nOR4;
each R7 is independently selected from C1-C6haloalkyl;
R8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N, O and S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N, O and S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a substituted C3-C8cycloalkyl, a tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl, —(C(R9)2)nOR4, —C(R9)2)nR5, —(C(R9)2)nC(O)OR4, —C(O)OR4 and —S(O)2R4;
each R9 is independently selected from H and C1-C6alkyl;
R10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a substituted C3-C8cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl [Me], —(C(R9)2)nOR4, —(C(R9)2)nR5, —(C(R9)2)nC(O)OR4 and —S(O)2R4;
t is 1, 2 or 3, and
each n is independently selected from 1, 2, 3 and 4.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is a compound of Formula (Ia), Formula (IIa), Formula (Ib) or Formula (IIb):
wherein:
m is 1 and R20 is selected from H, halo, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, deuterium, deuterated C1-C6alkyl, —CN, —(CR92)nOR4, —C(O)R4, —(CR92)nC(═O)OR4, R10, —(CR92)nR10, —((CR92)nO)tR4, —(CR92)nO(CR92)nR7, —(CR92)nC(═O)R4, —C(═O)N(R4)2, —OR4, and —(CR92)nCN;
or m is 4 and R20 is deuterium;
R1 is selected from C1-C6alkyl and halo;
each R11 is independently selected from H, halo and C1-C6alkyl;
L2 is —(CR92)n—, —CHR6—, —(CR92)nO—, —NH—, —(CR92)nC(═O)—, —C(═O)O(CR92)n—, —(CR92)nOC(═O)NR4—, —(CR92)nNR4C(═O)(CR92)n—, —(CR92)nNR4C(═O)—, or —(CR92)nNR4C(═O)O—;
R2 is R3 or L2R3;
R3 is selected from an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a piperidinone, a oxazolidin-2-one, pyrrolidinone, a pyrrolidin-2-one and a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, wherein the substituted 4-6 membered heterocycloalkyl of R3 is substituted with 1-4 substituents independently selected from C1-C6alkyl halo, —CN, C1-C6haloalkyl, —OR4, —C(═O)OR4, —C(═O)R4, —C(═O)R7, —C(═O)OR5, —(CR92)nOR4, —O(CR92)nOR4, —C(═O)O(CR92)nOR4, —N(R4)2, —C(═O)NR42, —NR4C(═O)OR4, —NR4C(═O)(CR92)nOR4, —NR4(CR92)nOR4, —NR4S(═O)2R4, —N(C(═O)OR4)2, R8, —(CR92)nR8, deuterated C1-C6alkoxy, —S(═O)2R4, —S(═O)2R7, —S(═O)2R8, —S(═O)2N(R4)2, —S(═O)2NHC(═O)OR4, —S(═O)2(CR92)nC(═O)OR4, S(═O)2(CR92)nOR4, a Spiro attached dioxolane, a Spiro attached dioxolane which is substituted with C1-C6alkyl, a spiro attached dioxane, a spiro attached tetrahydrofuranly, a spiro attached oxetane, a spiro attached cyclobutanone, a spiro attached cyclobutanol, a C1 alkyl bridge, an unsubstituted 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S and a 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S substituted with 1-3 substituents independently selected from C1-C6alkyl, halo, C1-C6haloalkyl, C1-C6haloalkoxy, —OR4 and R8;
each R4 is independently selected from H and C1-C6alkyl;
R5 is an unsubstituted C3-C8cycloalkyl, an unsubstituted 5-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N or O or a C3-C8cycloalkyl substituted with 1-3 substituents independently selected from C1-C6alkyl;
each R6 is independently selected from —NR4C(O)OR4, —OR4 and —(CR92)nOR4;
each R7 is independently selected from C1-C6haloalkyl;
R8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N, O and S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N, O and S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a substituted C3-C8cycloalkyl, a tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one, wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl, —(C(R9)2)nOR4, —(C(R9)2)nR5, —(C(R9)2)nC(O)OR4, —C(O)OR4 and —S(O)2R4;
each R9 is independently selected from H and C1-C6alkyl;
R10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O and S, a substituted C3-C8cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one,
wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O and S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl [Me], —(C(R9)2)nOR4, —(C(R9)2)nR5, —(C(R9)2)nC(O)OR4 and —S(O)2R4;
t is 1, 2 or 3, and
each n is independently selected from 1, 2, 3 and 4.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is selected from —CH3 and F.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R1 is —CH3.

### Claim 5 (depends on 1)

The compound of claim 1, wherein each R11 is independently selected from H, F and —CH3.

### Claim 6 (depends on 5)

The compound of claim 5, wherein each R11 is H.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R3 is selected from an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N and O, a piperidinone, a oxazolidin-2-one, pyrrolidinone, a pyrrolidin-2-one and a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N and O,
wherein the substituted 4-6 membered heterocycloalkyl of R3 is substituted with 1-4 substituents independently selected from C1-C6alkyl, halo, —CN, C1-C6haloalkyl, —OR4, —C(═O)OR4, —C(═O)R4, —C(═O)R7, —C(═O)OR5, —(CR92)nOR4, —C(═O)O(CR92)nOR4, —C(═O)NR42, —NR4C(═O)OR4, —NR4C(═O)(CR92)nOR4, —R8, —(CR92)nR8, —S(═O)2R4, —S(═O)2R7, —S(═O)2R8, —S(═O)2N(R4)2, —S(═O)2NHC(═O)OR4, —S(═O)2(CR92)nOR4, —S(═O)2(CR92)nC(═O)OR4 and a C1 alkyl bridge.

### Claim 8 (depends on 7)

The compound of claim 7, wherein each R4 is independently selected from H, methyl, ethyl, propyl, butyl, i-propyl and t-butyl.

### Claim 9 (depends on 7)

The compound of claim 7, wherein each R5 is cyclopropyl, cyclopropyl substituted with a methyl or morpholinyl.

### Claim 10 (depends on 7)

The compound of claim 7, wherein each R7 is independently selected from CH2F, —CHF2, —CH2CHF2, —CH2CF3 and —CF3.

### Claim 11 (depends on 7)

The compound of claim 7, wherein each R9 is independently selected from H, methyl and ethyl.

### Claim 12 (depends on 7)

The compound of claim 7, wherein R8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N and O, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N and O, a substituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N and O, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N and O, and a tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one, wherein the substituted 5-6 membered heteroaryl with 1-3 heteroatoms independently selected from N and O, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl and —C(═O)OR4.

### Claim 13 (depends on 12)

The compound of claim 12, wherein R8 is selected from pyridinyl, pyrazolyl tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, pyrimidinyl and oxadiazolyl, each of which is unsubstituted or substituted with 1-2 substituents independently selected from —CH3 and —C(═O)OC(CH3)3.

### Claim 14 (depends on 7)

The compound of claim 7, wherein R3 is selected from azetidinyl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, pyrrolidinyl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, piperidinyl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydropyranyl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrofuranyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, oxetanyl, oxetan-2-yl, oxetan-3-yl, morpholinyl, morpholin-2-yl, morpholin-3-yl and morpholin-4-yl, each of which is unsubstituted or each of which is substituted with 1-4 substituents independently selected from —CH3, —CH2CH3, F, —CF3, —CN, —OH, —C(═O)CF3, —OCH3, —C(═O)OCH3, —C(═O)CH3, —C(═O)OCH2CH2OCH3, —C═(O)OCH2CH3, —C(═O)OC(CH3)3, —CH2OH, —CH2OCH3, —CH2CH2CH2OCH3, —NHC(═O)OC(CH3)3, —NHC(═O)OCH3, —C(═O)N(CH3)2, —S(═O)2CH3, —S(═O)2CH2CH3, —S(═O)2CH2CH2CH3, —S(═O)2CH2CH2CH2CH3, —S(═O)2CH(CH3)2, —S(═O)2CH2CH2C(═O)OCH3, —S(═O)2CH2CH2OCH3, —S(═O)2CHF2, —S(═O)2NH2, —S(═O)2NHC(═O)OC(CH3)3, a C1alkyl bridge, —C(═O)OR5, —S(═O)2R8, —(CR92)nR8 and R8.

### Claim 15 (depends on 14)

The compound of claim 14, wherein:
R3 is azetidinyl substituted with —C(═O)OCH3.

### Claim 16 (depends on 14)

The compound of claim 14, wherein m is 1 and R20 is selected from H, halo, C1-C6alkyl, C1-C6haloalkyl, deuterium, deuterated C1-C6alkyl, —CN, —(CR92)nOR4, —C(O)R4, —(CR92)nC(═O)OR4, R10, —(CR92)nR10, —(CR92)nO(CR92)nR7, —(CR92)nC(═O)R4, —OR4, and —(CR92)nCN.

### Claim 17 (depends on 16)

The compound of claim 16, wherein m is 1 R20 is selected from H, -D, —F, —CH3, —CF3, —CN, —CH2CH2CH2CN, —CH2CH2CN, —OCH3, —CH2CH2C(═O)OC(CH3)3, —C(═O)CH3, —CH2CH2C(═O)CH3, —CD3, —CH2OH, —CH2CH2C(CH3)2OH, —CH2C(CH3)2OH, —C(CH3)2OH, —CH2OCH3, —CH2OCH2CF3, —CH2OCH2CHF2, and —CH2OCH2CH2F.

### Claim 18 (depends on 17)

The compound of claim 17, wherein m is 1 and R20 is —CH3.

### Claim 19 (depends on 17)

The compound of claim 17, wherein m is 1 and R20 is H.

### Claim 20 (depends on 16)

The compound of claim 16, wherein:
R10 is selected from morpholinyl, piperidinyl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazinyl, piperazin-1-yl, pyrazolyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, triazolyl, 1H-1,2,3-triazol-4-yl, 4H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, thiazolyl, thiazol-4-yl, thiazol-5-yl, imidazolyl, imidazol-1-yl, imidazol-2-yl, each of which is unsubstituted or each of which is substituted with 1-3 substituents independently selected from C1-C6alkyl, —(CR92)nOR4, —(C(R9)2)nC(O)OR4, —(C(R9)2)nR5 and —S(═O)2R4,
or R10 is selected from a oxazolidin-2-one and a pyrrolidin-2-one.

### Claim 21 (depends on 20)

The compound of claim 20, wherein:
R10 is selected from morpholinyl, piperidinyl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazinyl, piperazin-1-yl, pyrazolyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, triazolyl, 1H-1,2,3-triazol-4-yl, 4H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, thiazolyl, thiazol-4-yl, thiazol-5-yl, imidazolyl, imidazol-1-yl, imidazol-2-yl, each of which is unsubstituted or each of which is substituted with 1-3 substituents independently selected from —CH3, —CH2CH2OH, —CH2C(O)OH, —CH2CH2OH, —CH2C(CH3)2OH, —S(O)2CH3 and —CH2CH2—R5.

### Claim 22 (depends on 15)

The compound of claim 15, wherein m is 4 and R20 is deuterium.

### Claim 23 (depends on 1)

The compound of claim 1 selected from:
N-{5-[3-(azetidin-1-yl)-1,2,4-oxadiazol-5-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[3-(3,3-difluoroazetidin-1-yl)-1,2,4-oxadiazol-5-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{3-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1,2,4-oxadiazol-5-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[3-(4,4-difluoropiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[3-(4-fluoropiperidin-1-yl)-1,2,4-oxadiazol-5-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-6-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(oxolan-3-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(oxan-2-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate;
N-{5-[5-(5,5-difluorooxan-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2S)-5,5-difluorooxan-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2R)-5,5-difluorooxan-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl 3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-{5-[5-(1-methanesulfonylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-(2-methyl-5-{5-[1-(propane-1-sulfonyl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(oxan-4-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(oxolan-2-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[1-(ethanesulfonyl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[3-(morpholin-4-yl)propyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(3,3-difluoroazetidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(morpholin-4-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(1-sulfamoylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
tert-butyl (2S)-2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-(5-{5-[(2S)-1-methanesulfonylazetidin-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl N-{3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl}oxetan-3-yl]carbamate;
tert-butyl 3-[3-(4-fluoro-3-{imidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-(5-{5-[1-(ethanesulfonyl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl}-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(3,3-difluoropyrrolidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(4,4-difluoropiperidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[1-(butane-1-sulfonyl)azetidin-3-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2S)-4,4-difluoro-1-methanesulfonylpyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl 4-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxylate;
N-{5-[5-(1-methanesulfonylpiperidin-4-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(4-methanesulfonylmorpholin-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2S)-1-methanesulfonylpyrrolidin-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(2R)-4-methanesulfonylmorpholin-2-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[5-(5-{[(3S)-1-methanesulfonylpyrrolidin-3-yl]methyl}-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(3R)-1-methanesulfonylpiperidin-3-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl (2S)-2-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}pyrrolidine-1-carboxylate;
N-[5-(5-{[(2S)-1-methanesulfonylpyrrolidin-2-yl]methyl]-1,2,4-oxadiazol-3-yl)-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[(3,3,4,4-tetrafluoropyrrolidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[1-(difluoromethane)sulfonylazetidin-3-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-{2-methyl-5-[5-(oxan-2-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-[5-[(3,3-difluoropyrrolidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl]-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-[5-[(4,4-difluoropiperidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl]-2-fluorophenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{5-[(2S)-1-(propane-2-sulfonyl)azetidin-2-yl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-[3-(4-methyl-3-{pyrazolo[1,5-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-{2-methyl-5-[5-(oxan-3-ylmethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(1S)-1-(3,3-difluoroazetidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(5-{5-[(1S)-1-(3,3-difluoropyrrolidin-1-yl)ethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-(3-{4-methyl-3-[6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
ethyl 3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(3-{7-fluoroimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(3-{6-fluoroimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-(3-{4-methyl-3-[7-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-(3-{4-methyl-3-[7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
N-{5-[5-(1-methanesulfonyl-3-methylazetidin-3-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-(3-{3-[6-(3-cyanopropyl)imidazo[1,2-a]pyridine-3-amido]-4-methylphenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-[3-(3-{6-methoxyimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(4-methyl-3-{6-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-{3-[4-methyl-3-(7-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}imidazo[1,2-a]pyridine-3-amido)phenyl]-1,2,4-oxadiazol-5-yl}azetidine-1-carboxylate;
methyl 3-(3-{3-[6-(2-cyanoethyl)imidazo[1,2-a]pyridine-3-amido]-4-methylphenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-(3-{4-methyl-3-[6-(3-oxobutyl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-[3-(4-methyl-3-{6-[2-(morpholin-4-yl)ethyl]imidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-(3-{3-[6-(3-hydroxy-3-methylbutyl)imidazo[1,2-a]pyridine-3-amido]-4-methylphenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-(3-{4-methyl-3-[7-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
N-(2-methyl-5-{[5-(oxan-4-yl)-1,2,4-oxadiazol-3-yl]amino}-phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{[5-(oxan-2-yl)-1,2,4-oxadiazol-3-yl]amino}-phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-({5-[(2R)-oxolan-2-yl]-1,2,4-oxadiazol-3-yl}amino)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
N-[2-methyl-5-({5-[(2S)-oxolan-2-yl]-1,2,4-oxadiazol-3-yl}amino)phenyl]imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-(3-{4-methyl-3-[7-(3-oxobutyl)imidazo[1,2-a]pyridine-3-amido]phenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-(3-{3-[7-(3-hydroxy-3-methylbutyl)imidazo[1,2-a]pyridine-3-amido]-4-methylphenyl}-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
N-{2-methyl-5-[3-(morpholin-4-yl)-1,2,4-oxadiazol-5-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-[3-(4-methyl-3-{5,6,7,8-tetradeuteroimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-{5-[5-(azetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3,3-difluoroazetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-[3-(5-{imidazo[1,2-a]pyridine-3-amido}-2,4-dimethylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}-phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
7-fluoro-N-{2-methyl-5-[5-(oxan-4-ylamino)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
6-methyl-N-{2-methyl-5-[5-(oxan-4-ylamino)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-(3-[4-methyl-3-[6-(morpholin-4-yl)imidazo[1,2-a]pyridine-3-amido]phenyl]-1,2,4-oxadiazol-5-yl)azetidine-1-carboxylate;
methyl 3-[3-(4-methyl-3-{6-[(2,2,2-trifluoroethoxy)methyl]imidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
N-(5-{5-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-6-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3,3-difluoroazetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3,3-difluoroazetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-fluoroimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-[3-hydroxy-3-methylazetidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(4,4-difluoropiperidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(4-fluoropiperidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-{2-methyl-5-[5-(morpholin-4-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide;
N-{5-[5-(3,3-difluoropyrrolidin-1-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide;
7-methyl-N-(2-methyl-5-{5-[3-(trifluoromethyl)piperidin-1-yl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
N-(2-methyl-5-{3-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-1,2,4-oxadiazol-5-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide;
methyl 3-[3-(3-{6-[(2,2-difluoroethoxy)methyl]imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(3-{6-[(2-fluoroethoxy)methyl]imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(3-{7-hydrogenioimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate;
methyl 3-[3-(3-{6-hydrogenioimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate, and
N-(5-{5-[(3-cyanoazetidin-1-yl)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-6-(2,4-dimethyl-1,3-thiazol-5-yl)imidazo[1,2-a]pyridine-3-c arboxamide.

### Claim 24 (depends on 1)

The compound of claim 1 selected from methyl 3-[3-(4-methyl-3-{5,6,7,8-tetradeuteroimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate.

### Claim 25 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount a compound of claim 1 and a pharmaceutically acceptable carrier.

### Claim 26 (depends on 1)

A method for treating a disease or disorder where modulation of a kinase is implicated, wherein the method comprises administering to a system or subject in need of such treatment an effective amount of a compound of claim 1, wherein the kinase is selected from c-kit, PDGFRα and PDGFFRβ and wherein the disease is selected from irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), pulmonary arterial hypertension (PAH), primary pulmonary hypertension (PPH), pulmonary fibrosis, hepatic fibrosis, cardiac fibrosis, scleroderma, uticaria, dermatosis, type I diabetes or type II diabetes.