# US 9,518,026 B2 · 5-aminopyrazole-4-carboxamide inhibitors of CDPK1 from T. gondii and C. parvum

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- Number: US 9,518,026 B2
- Document ID: US9518026B2
- Status: Granted
- Kind: B2
- Application number: 14/891,237
- Filed: 2014-05-20
- Published: 2016-03-31
- Granted: 2016-12-13
- Earliest claimed: 2013-05-20
- Assignees: University of Washington through its Center for Commercialization
- Applicants: University of Washington Through Its Center for Commercialization
- Inventors: Erkang Fan; Wesley C. Van Voorhis; Zhongsheng Zhang; Wenlin Huang; Kayode K. Ojo
- Web page: https://patentgrep.com/patent/US9518026B2

## CPC

- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61K 31/415: 1,2-Diazoles
- A61K 31/4155: non condensed and containing further heterocyclic rings
- A61K 31/416: condensed with carbocyclic ring systems, e.g. indazole
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 31/454: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 33/02: Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P 33/06: Antimalarials
- C07D 231/14: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D 231/38: Nitrogen atoms (nitro radicals C07D231/16)
- C07D 235/08: Radicals containing only hydrogen and carbon atoms
- C07D 235/12: Radicals substituted by oxygen atoms
- C07D 311/20: hydrogenated in the hetero ring
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

The present disclosure is generally directed to compositions and methods for treating apicomplexan protozoan related disease, such as toxoplasmosis and cryptosporidiosis.

## Claims

### Claim 1

A compound of the formula:
or a pharmaceutically acceptable salt thereof, wherein
R1 is one of the formulas:
wherein
n is 0;
each R7 is independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR10, —SR10, —N(R10)2, —C(O)R10, —C(O)OR10, —C(O)N(R10)2, —S(O)2R10, —OC(O)R10, —OC(O)OR10, —OC(O)N(R10)2, —N(R10)C(O)R10, —N(R10)C(O)OR10, or —N(R10)C(O)N(R10)2, wherein each R10 is independently hydrogen or C1-6 alkyl;
R8 is halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, or -Q-R8′;
Q is —O—, —S—, —NH—, or —N(C1-6 alkyl)-;
R8′ is hydrogen, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C3-8 cycloalkyl, heterocyclyl, aryl, arylC1-6 alkyl, heteroaryl, or heteroarylC1-6 alkyl, wherein the alkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are optionally substituted with one, two, three, or four groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR14, —SR14, —N(R14)2, —C(O)R14, —C(O)OR14, —C(O)N(R14)2, —S(O)2R14, —OC(O)R14, —OC(O)OR14, —OC(O)N(R14)2, —N(R14)C(O)R14, —N(R14)C(O)OR14, or —N(R14)C(O)N(R14)2, wherein each R14 is independently hydrogen or C1-6 alkyl; and
each R9 is independently hydrogen or C1-6 alkyl;
R2 is hydrogen, C1-6 alkyl, C1-6 haloalkyl, —C1-4 alkyl-R12, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, monocyclic heterocyclyl, monocyclic heteroaryl, or phenyl, wherein the alkyl, cycloalkyl, heterocyclyl, heteroaryl, and phenyl groups are each optionally substituted with one or two R13 groups;
each R13 is independently C1-6 alkyl, C1-6 haloalkyl, —OR, —SR, —NR2, —C(O)R, —C(O)OR, —C(O)NR2, —S(O)2NR2, or —S(O)2R; and
where R12 is —OR, —SR, —NR2, —C(O)R, —C(O)OR, —C(O)NR2, —S(O)2R, —OC(O)R, —OC(O)OR, —OC(O)NR2, —N(R)C(O)R, —N(R)C(O)OR, —N(R)C(O)NR2, phenyl, monocyclic heteroaryl, C3-8 cycloalkyl, or monocyclic heterocyclyl, wherein the aryl, heteroaryl, C3-8 cycloalkyl, and heterocyclyl groups are each optionally substituted by one, two, or three groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR, —SR, —NR2, —C(O)R, —C(O)OR, —C(O)NR2, —S(O)2R, —OC(O)R, —OC(O)OR, —OC(O)NR2, —N(R)C(O)R, —N(R)C(O)OR, or —N(R)C(O)NR2;
and each R is independently hydrogen, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C3-8 cycloalkyl, heterocyclyl, aryl, arylC1-6 alkyl, heteroaryl, or heteroarylC1-6 alkyl, wherein the alkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are optionally substituted with one, two, three, or four groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR0, —SR0, —N(R0)2, —C(O)R0, —C(O)OR0, —C(O)N(R0)2, —S(O)2R0, —OC(O)R0, —OC(O)OR0, —OC(O)N(R0)2, —N(R0)C(O)R0, —N(R0)C(O)OR0, or —N(R0)C(O)N(R0)2, wherein each R0 is independently hydrogen or C1-6 alkyl;
or R2 and R3 together with the atoms to which they are attached form 2-oxo-2,3-dihydro-imidazolyl ring;
R3 and R4 are independently hydrogen; and
R5 and R6 are independently hydrogen.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R is one of the formulas:

### Claim 3 (depends on 2)

A compound according to claim 2, wherein R8 is -Q-R8′; wherein
Q is —O—, —S—, —NH—, or —N(C1-6 alkyl)-;
R8′ is hydrogen, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C3-8 cycloalkyl, heterocyclyl, aryl, arylC1-6 alkyl, heteroaryl, or heteroarylC1-6 alkyl wherein the alkyl, aryl, arylalkyl, heteroaryl, and heteroarylalkyl are optionally substituted with one, two, three, or four groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR14, —SR14, —N(R14)2, —C(O)R14, —C(O) OR14, —C(O)N(R14)2, —S(O)2R14—OC(O)OR14, —OC(O)N(R14)2, —N(R14)C(O)R14, —N(R14)C(O)OR14, or —N(R14)C(O)N(R14)2, wherein each R14 is independently hydrogen or C1-6 alkyl.

### Claim 4 (depends on 2)

A compound according to claim 2, wherein R8 is halogen, C1-6 alkyl, or C1-6 haloalkyl.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R1 is one of the formulas:

### Claim 6 (depends on 1)

A compound according to claim 1, wherein each R7 is independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR10, —SR10, —N(R10)2, —C(O)R10, —C(O)OR10, or —C(O)N(R10)2, wherein each R10 is independently hydrogen or C1-6 alkyl.

### Claim 7 (depends on 6)

A compound according to claim 6, wherein each R7 is independently halogen, cyano, nitro, C1-6 alkyl, or C1-6 haloalkyl.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R1 is one of the formulas:

### Claim 9 (depends on 1)

A compound according to claim 1, wherein each R9 is independently hydrogen or C1-4 alkyl.

### Claim 10 (depends on 9)

A compound according to claim 9, wherein each R9 is independently hydrogen or methyl.

### Claim 11 (depends on 1)

A compound according to claim 1, wherein R2 is C1-6 alkyl, C1-6 haloalkyl, —C1-4 alkyl-R12, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, monocyclic heterocyclyl, monocyclic heteroaryl, or phenyl, wherein the alkyl, cycloalkyl, heterocyclyl, heteroaryl, and phenyl groups are each optionally substituted with one or two R13 groups.

### Claim 12 (depends on 11)

A compound according to claim 11, where R12 is —OR, —NR2, —C(O)R, —C(O)OR, —C(O)NR2, —S(O)2R, phenyl, monocyclic heteroaryl, C3-8 cycloalkyl, or monocyclic heterocyclyl, wherein the aryl, heteroaryl, C3-8 cycloalkyl, and heterocyclyl groups are each optionally substituted by one, two, or three groups that are each independently halogen, cyano, nitro, C1-6 alkyl, C1-6 haloalkyl, —OR, —SR, —NR2, —C(O)R, —C(O)OR, —C(O)NR2, —S(O)2R, —OC(O)R, —OC(O)OR, —OC(O)NR2, —N(R)C(O)R, —N(R)C(O)OR, or —N(R)C(O)NR2.

### Claim 13 (depends on 12)

A compound according to claim 12, where R12 is —OR.

### Claim 14 (depends on 1)

A compound according to claim 1, wherein R2 is C3-8 cycloalkyl or monocyclic heterocyclyl, each optionally substituted with one or two R13 groups.

### Claim 15

A compound, which is:
5-amino-1-tert-butyl-3-(6-ethoxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
1-tert-butyl-3-(6-ethoxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(naphthalen-2-yl)-1-(piperidin-4-ylmethyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(6-ethoxynaphthalen-2-yl)-1-((1-methylpiperidin-4-yl)methyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(6-methoxynaphthalen-2-yl)-1-((1-methylpiperidin-4-yl)methyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(6-methoxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-ethyl-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-isopropyl-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-isobutyl-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(cyclopropylmethyl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(cyclohexylmethyl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cyclohexyl-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(naphthalen-2-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(naphthalen-2-yl)-1-neopentyl-1H-pyrazole-4-carboxamide;
5-amino-1-(1-methylpiperidin-4-yl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-((1-methylpiperidin-4-yl)methyl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(2-hydroxyethyl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(2-morpholinoethyl)-3-(naphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(6-hydroxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(6-methoxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(6-propoxynaphthalen-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(2-methylbenzofuran-3-yl)-1H-pyrazole-4-carboxamide;
3-(3-amino-1H-indazol-6-yl)-1-(tert-butyl)-1H-pyrazole-4-carboxamide;
3-(3-amino-1-methyl-1H-indazol-6-yl)-1-(tert-butyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(1-methyl-1H-indazol-5-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(1-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(1,2-dimethyl-1H-benzo[d]imidazol-5-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-amino-1-methyl-1H-benzo[d]imidazol-5-yl)-1-(tert-butyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(2-oxo-2H-chromen-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(quinolin-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(6-ethoxyquinolin-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(quinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-isopropyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-isobutyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-neopentyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(cyclopropylmethyl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
1-isobutyl-3-(2-(2,2,2-trifluoroethoxy)quinolin-6-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine;
5-amino-1-cyclopentyl-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cyclohexyl-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cycloheptyl-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(cyclohexylmethyl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(1-hydroxypropan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(2-hydroxy-2-methylpropyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(4-hydroxybutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(3-hydroxy-2,2-dimethylpropyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(2-ethoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(cyclopropylmethyl)-3-(2-ethoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cyclohexyl-3-(2-ethoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cycloheptyl-3-(2-ethoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-ethoxyquinolin-6-yl)-1-(3-hydroxy-2,2-dimethylpropyl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-fluoroquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-chloroquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-(trifluoromethyl)quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-methylquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-ethylquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-methoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-(trifluoromethoxy)quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-isopropoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-tert-butyl-3-(7-propoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-(cyclopropylmethoxy)quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-cyclopropoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(2-cyclopropoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-cyclobutoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(2-cyclobutoxyquinolin-6-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-cyclobutoxyquinolin-3-yl)-1-cyclobutyl-1H-pyrazole-4-carboxamide;
5-amino-3-(2-cyclobutoxyquinolin-6-yl)-1-cyclobutyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-cyclobutoxyquinolin-3-yl)-1-cyclopentyl-1H-pyrazole-4-carboxamide;
5-amino-3-(2-cyclobutoxyquinolin-6-yl)-1-cyclopentyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-cyclobutoxyquinolin-3-yl)-1-cyclohexyl-1H-pyrazole-4-carboxamide;
5-amino-3-(2-cyclobutoxyquinolin-6-yl)-1-cyclohexyl-1H-pyrazole-4-carboxamide;
5-amino-3-(7-cyclobutoxyquinolin-3-yl)-1-(3-hydroxy-2,2-dimethylpropyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-cyclobutoxyquinolin-6-yl)-1-(3-hydroxy-2,2-dimethylpropyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-(2-methoxyethoxy)quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(2-hydroxyethyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-(neopentyloxy)quinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(7-isobutoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(2-methoxyethyl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-N, 1-bis(2-methoxyethyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(2,4-dimethylpentan-3-yl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
6-(7-ethoxyquinolin-3-yl)-2-oxo-2,3-dihydro-1H-imidazo[1,2-b]pyrazole-7-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(3-hydroxybutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(3-hydroxy-3-methylbutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(3-methylbutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(1,3-dihydroxypropan-2-yl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-(1-cyclopropylethyl)-3-(7-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-ethoxyquinolin-6-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-ethoxyquinolin-6-yl)-1-(3-hydroxy-3-methylbutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(4-hydroxy-3,3-dimethylbutan-2-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(7-ethoxyquinolin-3-yl)-1-(1-methylcyclohexyl)-1H-pyrazole-4-carboxamide;
5-amino-1-(tert-butyl)-3-(6-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-1-cyclohexyl-3-(6-ethoxyquinolin-3-yl)-1H-pyrazole-4-carboxamide;
5-amino-3-(2-ethoxyquinolin-6-yl)-isopropyl-1H-pyrazole-4-carboxamide;
or pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 1)

A pharmaceutical composition comprising one or more of compounds according to claim 1.