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US 10,479,792 B2Granted
Compounds
AssigneesGiaxoSmithKline Intellectual Property Development Limited, University of Dundee
InventorsStephen Brand, Peter George Dodd, Eun Jung Ko, Maria Marco Martin, Timothy James Miles, Lars Henrik Sandberg, Michael George Thomas, Stephen Thompson
Life of this patent
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Abstract
A compound of Formula (I), or a salt thereof, compositions comprising the compound, processes for its preparation and its use in therapy, for example in the treatment of parasitic diseases such as Chagas disease, Human African Trypanosomiasis (HAT), Animal African trypanosomiasis (AAT) and leishmaniasis, particularly visceral leishmaniasis (VL).
Claims24
A compound of Formula (I), or a salt thereof,
- wherein
- A1 is CH;
- A2 is selected from CR13 and N;
- R1 is selected from C1-C6alkyl, C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl, C5-C6heteroaryl, C1-C6alkoxy, —OC3-C7cycloalkyl and NR10aR10b;
- wherein C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl, C5-C6heteroaryl and —OC3-C7cycloalkyl are optionally substituted with one to three groups independently selected from hydroxy, methoxy, C1-C3alkyl and halo;
- L1 is a linker group selected from —C(O)— and —S(O)n—, wherein n represents 1 to 2;
- R3 is selected from hydrogen, halo, methyl, methoxy and cyano;
- R4 is selected from hydrogen, halo, methyl, methoxy and cyano;
- R2 is selected from hydrogen, halo, Ar, Cy, X, NR5aR5b and —C(O)—R15;
- Ar is selected from phenyl and C5-C6heteroaryl, each of which is optionally substituted with one to three groups independently selected from halo and -L2-R7;
- L2 is a linker group selected from a bond, —(CH2)m—, —O(CH2)m—, —C2-C4alkenyl-, —OC2-C4alkenyl-, —(CH2)p—NH—(CH2)q—, and —(CH2)pC(O)—(CH2)q—;
- wherein m represents 1 to 4 and p and q independently represent 0 to 4;
- R7 is selected from hydrogen;
- hydroxy;
- NR8aR8b;
- C4-C7heterocycloalkyl optionally substituted with one or two C1-C3alkyl groups;
- C3-C7cycloalkyl;
- C1-C6alkoxy optionally substituted with one NR14aR14b group;
- and phenyl optionally substituted with one to three groups independently selected from halo, methoxy and methyl;
- Cy is selected from C3-C7cycloalkyl, C4-C7heterocycloalkyl, C5-C7cycloalkenyl and C5-C7heterocycloalkenyl, each of which is optionally substituted with one to three groups independently selected from C1-C3alkyl, C1-C3alkoxy, C4-C7heterocycloalkyl, NR11aR11b, ═O, —C(O)—R15 and —C(O)O—R15;
- X is selected from C1-C6alkyl, C2-C6alkenyl and C1-C6alkoxy, each of which is optionally substituted with one to three groups independently selected from hydroxy, methoxy, halo, NR13aR13b and C4-C7heterocycloalkyl, wherein C4-C7heterocycloalkyl is optionally substituted with one to three C1-C3alkyl groups;
- R5a is selected from hydrogen;
- C1-C6alkyl optionally substituted with one group selected from Ar and Cy;
- —C(O)—R9;
- —C(O)—OR9;
- and —SO2—R9;
- R5b is selected from hydrogen and C1-C3alkyl;
- R8a and R8b are independently selected from hydrogen and C1-C3alkyl;
- R9 is selected from C1-C6alkyl, C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl and C5-C6heteroaryl;
- R10a and R10b are independently selected from hydrogen and C1-C3alkyl;
- R11a and R11b are independently selected from hydrogen and C1-C3alkyl;
- R12 is selected from hydrogen, halo and methyl;
- R13 is selected from hydrogen, C1-C3alkyl, —C(O)—C4-C7heterocycloalkyl, —C(O)—C1-C3alkyl and —C(O)—C3-C7cycloalkyl;
- R13a and R13b are independently selected from hydrogen and C1-C3alkyl;
- R14a and R14b are independently selected from hydrogen and C1-C3alkyl;
- and
- R15 is selected from C1-C6alkyl, Ar, C3-C7cycloalkyl and C4-C7heterocycloalkyl.
34 more elements
A compound of Formula (IA), or a salt thereof,
- wherein
- A1 is CH;
- A2 is selected from CR13 and N;
- R1 is selected from C1-C6alkyl, C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl, C5-C6heteroaryl, C1-C6alkoxy, —OC3-C7cycloalkyl and NR10aR10b;
- wherein C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl, C5-C6heteroaryl and —OC3-C7cycloalkyl are optionally substituted with one to three groups selected from hydroxy, methoxy, C1-C3alkyl and halo;
- L1 is a linker group selected from —C(O)— and —S(O)n—;
- wherein n represents 1 to 2;
- R3 is selected from hydrogen, halo, methyl, methoxy and cyano;
- R4 is selected from hydrogen, halo, methyl, methoxy and cyano;
- R2 is selected from hydrogen, halo, Ar, Cy, X and NR5aR5b;
- Ar is selected from phenyl and C5-C6heteroaryl, each of which is optionally substituted with one to three groups independently selected from NR6aR6b and -L2-R7;
- L2 is a linker group selected from a bond, —(CH2)m—, —O(CH2)m—, —C2-C4alkenyl- and —OC2-C4alkenyl-;
- wherein m represents 1 to 4;
- R7 is selected from hydrogen, C4-C7heterocycloalkyl, C3-C7cycloalkyl, C1-C6alkoxy, hydroxy and NR8aR8b;
- Cy is selected from C3-C7cycloalkyl, C4-C7heterocycloalkyl, C5-C7cycloalkenyl and C5-C7heterocycloalkenyl, each of which is optionally substituted with one to three groups independently selected from C1-C3alkyl, C4-C7heterocycloalkyl and NR11aR11b;
- X is selected from C1-C6alkyl, C2-C6alkenyl and C1-C6alkoxy, each of which is optionally substituted with one to three groups independently selected from hydroxy, methoxy, halo and C4-C7heterocycloalkyl, wherein C4-C7heterocycloalkyl is optionally substituted with one to three C1-C3alkyl groups;
- R5a is selected from hydrogen, C1-C6alkyl, —C(O)—R9, —C(O)—OR9 and —SO2—R9;
- R5b is selected from hydrogen and C1-C3alkyl;
- R6a and R6b are independently selected from hydrogen and C1-C3alkyl;
- R8a and R8b are independently selected from hydrogen and C1-C6alkyl;
- R9 is selected from C1-C6alkyl, C3-C7cycloalkyl, C4-C7heterocycloalkyl, phenyl and C5-C6heteroaryl;
- R10a and R10b are independently selected from hydrogen and C1-C3alkyl;
- R11a and R11b are independently selected from hydrogen and C1-C3alkyl;
- R12 is selected from hydrogen, halo and methyl;
- and
- R13 is selected from hydrogen and C1-C3alkyl.
23 more elements
Dependencies are inferred from the claim text.