# US 2014/0155367 A1 · Compounds and compositions for the treatment of parasitic diseases

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- Number: US 2014/0155367 A1
- Document ID: US20140155367A1
- Status: Published application
- Kind: A1
- Application number: 14/083,203
- Filed: 2013-11-18
- Published: 2014-06-05
- Earliest claimed: 2012-11-19
- Assignees: Novartis AG; Irm LLC
- Inventors: Arnab Kumar Chatterjee; Advait Suresh Nagle; Prasuna Paraselli; Ravinder Reddy Kondreddi; Seh Yong Leong; Pranab Kumar Mishra; Robert Joseph Moreau; Jason Thomas Roland; Wei Lin Sandra Sim; Oliver Simon; Liying Jocelyn Tan; Bryan KS Yeung; Bin Zou; Venkatataiah Bollu
- Web page: https://patentgrep.com/patent/US20140155367A1

## CPC

- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/538: ortho- or peri-condensed with carbocyclic ring systems
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- C07D 471/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

The present invention provides compounds of formula I: or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a Plasmodium parasite, such as malaria.

## Claims

### Claim 1

A compound of Formula I,
or a pharmaceutical acceptable salt, tautomer or stereoisomer thereof, wherein
n is 0, 1, 2 or 3;
p is 0, 1, 2 or 3;
L is selected from the group consisting of *—(CHR3)1-3—, *—CHR3N(R2)—, *—CHR3O—, *—CHR3S—, *—CHR3S(O)—, *—CHR3N(R2)CHR3—, *—C(O)—, *—C(O)N(R2)—, *—C(O)N(R2)CHR3—, *—N(R2)—, *—N(R2)CHR3—, *—N(R2)C(O)—, *—N(R2)C(O)N(R2)—, *—N(R2)S(O)2—, wherein
* represents the point of attachment of L to the pyrazolo[1,5-a]pyridine fused ring depicted in Formula I;
each R2 is independently selected from the group consisting of hydrogen, C1-6alkyl, haloC1-6alkyl, R—C0-4alkylene, and R—C0-4alkylene-C(O)—, wherein R is selected from the group consisting of hydroxyl, C1-4alkoxy, amino, C1-4alkylamino, C3-6cycloalkyl, C4-6heterocycloalkyl, and C5-6heteroaryl, wherein the C3-6cycloalkyl, C4-6heterocycloalkyl, and C5-6heteroaryl of R are each unsubstituted or substituted with 1-2 substituents independently selected from the group consisting of halo, amino, hydroxyl, C1-4alkyl, C1-4alkoxy, oxo, and C5-6heteroaryl; and
each R3 is independently selected from the group consisting of hydrogen and C1-4alkyl;
Ring A is selected from the group consisting of C6-10aryl and C3-10heteroaryl;
Ring C is selected from the group consisting of C6-10aryl, C5-10heteroaryl, C5-7cycloalkyl, C5-7heterocycloalkyl, and fused bicyclyl comprising a C5-6heterocycloalkyl fused to a phenyl;
each R1 is independently selected from the group consisting of halo, cyano, amino, C1-4alkyl, C1-4alkoxyl, halo-C1-4alkyl, —C(O)NR7R8, —NHC(O)R11, phenyl, and C5-6heteroaryl; wherein
the phenyl and C5-6heteroaryl of R1 are each unsubstituted or substituted with 1-2 substituents independently selected from the group consisting of C1-4alkyl, amino, halo, and C1-4alkylamino;
R7 and R8 are each independently selected from hydrogen, C1-4alkyl and haloC1-4alkyl;
R11 is C1-6alkyl, unsubstituted or substituted with 1-2 substituents independently selected from the group consisting of amino, C3-6cycloalkyl and C4-6heterocycloalkyl;
R17 is selected from the group consisting of cyano, halo, C1-4alkyl, halo-C1-4alkyl, oxo, C3-6cycloalkyl, and —SO2—C1-4alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein L is selected from the group consisting of *—C(O)N(R2)—, and *—N(R2)C(O)—, wherein each R2 is independently selected from hydrogen, C1-4alkyl, and R—C0-4alkylene, and wherein R is selected from the group consisting of C4-6heterocycloalkyl and C5-6heteroaryl, each of which is unsubstituted or substituted with 1-2 substituents independently selected from the group consisting of halo, amino, hydroxyl, C1-4alkyl, C1-4alkoxy, oxo, and C5-6heteroaryl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein L is selected from the group consisting of *—CH(CH3)—, *—CH2CH2—, *—CH2N(CH3)—, *—CH2N(C(O)(CH2)1-2NH(CH3))—, *—CH2N(C(O)—(CH2)1-2NH2)—, *—CH2N((C(O)—(CH2)1-2N(CH3)2)—, *—CH2N(C(O)(CH2)1-2OH)—, *—CH(CH3)N(CH3)—, *—CH2O—, *—CH2S—, *—CH2S(O)—, *—C(O)—, *—C(O)N(CH3)—, *—C(O)N(CH2CH3)—, *—C(O)N(CH(CH3)2)—, *—C(O)N(C(CH3)3)—, *—C(O)N(CH2CH(CH3)2)—, *—C(O)N(CH(CH3)CH2CH3)—, *—C(O)N(CH2CH2OCH3)—, *—C(O)N(CH2CH2N(CH3)2)—, *—C(O)N(CH3)CH2—, *—NHCH2—, *—N(CH3)CH2—, *—N(CH2-tetrahydropyran-4-yl)-C(O)—,*—N(CH3)C(O)—, *—N(CH3)C(O)NH—, *—N(CH3)S(O)2—, *—C(O)N((CH2)0-1-cyclopropyl)-, *—C(O)N((CH2)0-1-cyclobutyl)-, *—C(O)N((CH2)0-1-cyclopentyl)-, *—C(O)N((CH2)0-1-cyclohexyl)-, *—C(O)N(CH2-tetrahydropyran-4-yl)-, *—C(O)N((CH2)2-(1,1-dioxidothiomorpholino-4-yl))-, *—C(O)N(CH2-1,1-dioxidothiomorpholino-4-yl)-, *—C(O)N((CH2)2-tetrahydropyran-4-yl)), *—C(O)N((CH2)1-2-morpholin-4-yl)-, *—C(O)N(oxetan-3-yl)-, *—C(O)N(CH2-oxetan-3-yl)-, *—C(O)N(CH(CH3)—CH2-1-H-pyrazoly-1-yl)-, *—CH2N(C(O)—(CH2)1-2-morpholinyl))-, *—CH2N(C(O)—(CH2)1-2-4-methylpiperizin-1-yl)), *—CH2N(C(O)—(CH2)1-2-tetrahydropyran-4-yl)-, and *—CH2N(C(O)(CH2)1-2-oxetan-3-yl)-.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein Ring A is selected from the group consisting of phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, pyrrolopyridinyl, and indazolyl, each of which is unsubstituted or substituted by (R1)n.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein Ring C is selected from the group consisting of
each of which is unsubstituted or substituted by (R17)p.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein Ring C is selected from the group consisting of phenyl and pyridinyl, each of which is unsubstituted or substituted by (R17)p.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein each R1 is independently selected from the group consisting of trifluoromethyl, cyano, —NH2—, —C(O)NH2, —C(O)NHCH3, —C(O)N(CH3)2, and —NHC(O)CH(NH2)(CH3).

### Claim 8 (depends on 1)

The compound according to claim 1, wherein each R17 is independently selected from the group consisting of cyano, halo, C1-4alkyl, haloC1-4alkyl, —SO2—C1-4alkyl, and C3-6cycloalkyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein the compound is of Formula Ia:
or a pharmaceutical acceptable salt, tautomer or stereoisomer thereof, wherein
n is 1 or 2;
p is 1 or 2;
Ring A is phenyl, pyridinyl, or pyrimidinyl;
Ring C is phenyl or pyridinyl;
L is *—C(O)NR2— or *—NR2C(O)—, wherein R2 is selected from hydrogen, C1-4alkyl, C3-6cycloalkyl-(C0-4)alkylene, C4-6heterocycloalkyl-(C0-4)alkylene, wherein the C4-6heterocycloalkyl is selected from the group consisting of piperazinyl, morpholinyl, thiomorpholinyl, tetrahydropyranyl, and oxetanyl, and wherein the C3-6cycloalkyl is selected from cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
each R1 is independently *—C(O)NR7R8 or —NH2—, wherein R7 and R8 are each independently hydrogen or C1-4alkyl; and
R17 is selected from the group consisting of cyano, halo, —NH2—, —C(O)NH2, —C(O)NH(CH3), and —C(O)N(CH3)2.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound, or a pharmaceutical acceptable salt, tautomer or stereoisomer thereof, is selected from the group consisting of:
N-(4-cyanophenyl)-N-methyl-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
4-fluoro-N-methyl-N-((3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)methyl)aniline;
N-(4-chlorophenyl)-N-methyl-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-fluorophenyl)-N-methyl-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-methyl-N-(5-methylpyridin-2-yl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
4-chloro-N-methyl-N-((3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)methyl)aniline;
N,5-dimethyl-N-((3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)methyl)yridine-2-amine;
5-((4-fluorophenoxy)methyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine;
N-(4-cyanophenyl)-N-(2-methoxyethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-cyanophenyl)-N-(2-(dimethylamino)ethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-cyanophenyl)-N-((tetrahydro-2H-pyran-4-ylmethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-(methylsulfonyl)phenyl)-N-((tetrahydro-2H-pyran-4-ylmethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(5-cyanopyridin-2-yl)-N-methyl-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-methyl-N-(5-methylpyridin-3-yl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
5-(((5-methylpyridin-2-yl)oxy)methyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine;
5-(4-fluorophenethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine;
N-(4-cyanophenyl)-N-methyl-3-(1-methyl-1H-indazol-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-acetamidopyridin-3-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-carbamoylphenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-carbamoylphenyl)-N-(4-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
5-(((4-fluorophenyl)thio)methyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine;
5-(((4-fluorophenyl)sulfinylmethyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine;
3-(4-(1H-pyrazol-5-yl)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-cyanophenyl)-N-methyl-3-(5-(trifluoromethyl)pyridine-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(5-cyanopyridin-2-yl)-N-methyl-3-(5-(trifluoromethyl)pyridine-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
(S)-3-(4-(2-aminopropanamido)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(5-carbamoylpyridin-2-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
4-cyano-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)benzamide;
4-fluoro-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)benzamide;
4-cyano-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-yl)benzenesulfonamide;
4-fluoro-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-yl)benzenesulfonamide;
3-(4-carbamoylphenyl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide; N-methyl-3-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)yridine-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-methyl-N-(5-(methylsulfonyl)pyridine-2-yl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-fluorobenzyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-amine
N-(4-fluorobenzyl)-3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-amine;
N-methyl-6-(trifluoromethyl)-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)nicotinamide;
N-methyl-5-(trifluoromethyl)-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]yridine-5-yl)picolinamide;
4-cyano-N-((tetrahydro-2H-pyran-4-ylmethyl)-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)benzamide;
N-(4-cyanophenyl)-N-methyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-aminopyridin-3-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-aminophenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-(2-aminoacetamido)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
(R)-3-(4-(2-aminopropanamido)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
(S)-3-(4-(2-amino-3-methylbutanamido)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
(S)-3-(4-(2-amino-2-cyclohexylacetamido)phenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-fluorophenyl)-1-methyl-1-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)urea;
6-(1,1-difluoroethyl)-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)nicotinamide;
6-cyclopropyl-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)nicotinamide;
4-cyclopropyl-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)benzamide;
5-fluoro-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)picolinamide;
N-methyl-4-(methylsulfonyl)-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)benzamide;
N-(5-cyanopyridin-2-yl)-N-methyl-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-aminopyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
4-chloro-N-methyl-N-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)benzamide;
N-(3-(4-carbamoylphenyl)pyrazolo[1,5-a]pyridin-5-yl)-4-fluoro-N-methylbenzamide
4-fluoro-N-methyl-N-(3-(4-(5-(methylamino)-1,3,4-thiadiazol-2-yl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)benzamide;
N-methyl-N-(5-(methylsulfonyl)pyridin-2-yl)-3-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(5-cyanopyridin-2-yl)-N-methyl-3-(5-methylpyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(5-cyanopyridin-2-yl)-3-(5-methoxypyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(5-carbamoylpyridin-2-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-carbamoylphenyl)-N-methyl-N-(5-(trifluoromethyl)pyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-carbamoylphenyl)-N-methyl-N-(5-methylpyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-fluorophenyl)-N-methyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
4-(5-(1-(methyl(5-methylpyridin-2-yl)amino)ethyl)pyrazolo[1,5-a]pyridin-3-yl)benzamide;
4-(5-(1-(7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethyl)pyrazolo[1,5-a]pyridin-3-yl)benzamide;
N-(4-cyanophenyl)-N-methyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(4-(5-(1-(methyl(5-methylpyridin-2-yl)amino)ethyl)pyrazolo[1,5-a]pyridin-3-yl)phenyl)acetamide;
3-(4-acetamidophenyl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
4-(5-(7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl)benzamide;
4-(5-(7-fluoro-3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl)benzamide;
4-(5-(7-fluoro-3,4-dihydro-2H-benzo[b][1,4]oxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl)-N-methylbenzamide;
4-(5-(7-fluoro-3-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-4-carbonyl)pyrazolo[1,5-a]pyridin-3-yl)-N-methylbenzamide;
N-(5-cyanopyridin-2-yl)-N-methyl-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(5-cyanopyridin-2-yl)-3-(4-(methylcarbamoyl)phenyl)-N-(oxetan-3-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
N-(1-(1H-pyrazol-1-yl)propan-2-yl)-3-(4-carbamoylphenyl)-N-(5-cyanopyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-fluoropyridin-3-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-amino-3,5-dimethylphenyl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-methylpyridin-3-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(4-carbamoylphenyl)-N-(4-cyanocyclohexyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(2-aminopyrimidin-5-yl)-N-(4-cyanophenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-cyanopyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-chloropyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-(dimethylcarbamoyl)pyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide;
3-(6-amino-5-methoxypyridin-3-yl)-N-(5-cyanopyridin-2-yl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide; and
3-(4-carbamoylphenyl)-N-(4-chloro-2-formylphenyl)-N-methylpyrazolo[1,5-a]pyridine-5-carboxamide.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising at least one compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.

### Claim 12 (depends on 11)

The pharmaceutical composition according to claim 11, further comprising a second agent, wherein the second agent is an antimalarial drug selected from artemisinin, artemether, artesunate, arteflene, dihydroartemisinin, chlorproguanil, trimethoprim, chloroquine, quinine, mefloquine, amodiaquine, atovaquone, proguanil, lumefantrine, piperaquine, pyronaridine, halofantrine, pyrimethamine-sulfadoxine, quinacrine, pyrimethamine-dapsone, quinidine, amopyroquine, sulphonamides, primaquine, ferroquine, tafenoquine, arterolane, and pyronaridine.

### Claim 13 (depends on 1, 11)

A method for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a Plasmodium parasite, comprising administering to a subject a therapeutically effective amount of a compound according to claim 1 or a composition according to claim 11, wherein the administering may be in combination with a second agent.

### Claim 14 (depends on 13)

The method according to claim 13, wherein the disease is malaria.

### Claim 15 (depends on 13)

The method according to claim 13, wherein the Plasmodium parasite is at the blood stages.

### Claim 16 (depends on 13)

The method according to claim 13, wherein the Plasmodium parasite is at the hepatic stages.

### Claim 17 (depends on 14)

The method of claim 14, wherein the Plasmodium parasite is selected from group consisting of Plasmodium falciparum, Plasmodium vivax, Plasmodium ovale, and Plasmodium malaria.

### Claim 18 (depends on 13)

The method according to claim 13, wherein the second agent is selected from a kinase inhibitor, an anti-malarial drug and an anti-inflammatory agent.

### Claim 19 (depends on 18)

The method according to claim 18, wherein the anti-malarial drug is selected from artemisinin, artemether, artesunate, arteflene, dihydroartemisinin, chlorproguanil, trimethoprim, chloroquine, quinine, mefloquine, amodiaquine, atovaquone, proguanil, lumefantrine, piperaquine, pyronaridine, halofantrine, pyrimethamine-sulfadoxine, quinacrine, pyrimethamine-dapsone, quinidine, amopyroquine, sulphonamides, primaquine, ferroquine, tafenoquine, arterolane, and pyronaridine.

### Claim 20 (depends on 18)

The method according to claim 18, wherein the compound is administered prior to, simultaneously with, or after the second agent.