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US 2026/0083728 A1Published application
Compounds for treating infections with parasitic protozoa
AssigneesOhio State Innovatiion Foundation, University of Kansas
InventorsKarl WERBOVETZ, Pankaj SHARMA, Chris LA ROSA, Zhuo WANG, Yiru JIN, Mei FENG
Life of this patent
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Abstract
This disclosure describes compounds of Formula I and Formula II, pharmaceutically acceptable salts or derivatives thereof, and pharmaceutical compositions thereof, useful in treating infections caused by parasitic protozoa, in particular protozoa of the genera Leishmania or Trypanosoma.
Claims20
A compound of Formula I
- or a pharmaceutically acceptable salt or derivative thereof;
- wherein:
- R1 is selected from halo, cyano, azido, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-(C0-C3 alkyl)-, (3- to 8-membered monocyclic or bicyclic heterocycle)-(C0-C3 alkyl)-, (6- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, RxO—(C0-C3 alkyl)-, RxS—(C0-C3 alkyl)-, (RxRyN)—(C0-C3 alkyl)-, RxO—C(O)—(C0-C3 alkyl)-, RxS—C(O)—(C0-C3 alkyl)-, (RxRyN) C(O)—(C0-C3 alkyl)-, RxO—S(O)2—(C0-C3 alkyl)-, (RxRyN) S(O)2—(C0-C3 alkyl)-, RzC(O)—O—(C0-C3 alkyl)-, RzC(O)—(RxN)—(C0-C3 alkyl)-, RzS(O)2—O—(C0-C3 alkyl)-, RzS(O)2—(RxN)—(C0-C3 alkyl)-, RzC(O)—(C0-C6 alkyl)-, RzS(O)—(C0-C3 alkyl)-, and RzS(O)2—(C0-C3 alkyl)-;
- m is 0, 1, 2, 3, 4, or 5;
- Rx and Ry are independently selected at each occurrence from hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C0-C3 alkyl)-, (4- to 6-membered heterocycle)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, and (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, each of which may be optionally substituted with one or more Y groups as allowed by valency;
- Rz is independently selected at each occurrence from hydrogen, halo, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C0-C3 alkyl)-, (4- to 6-membered heterocycle)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, —ORx, —SRx, and —NRxRy, each of which may be optionally substituted with one or more Y groups as allowed by valency;
- and
- Y is independently selected at each occurrence from alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aldehyde, amino, carboxylic acid, ester, ether, halo, hydroxy, keto, nitro, cyano, azido, oxo, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, sulfonylamino, or thiol;
- with the proviso that
- cannot be 3,5-dimethylphenyl.
7 more elements
A compound of Formula II
- or a pharmaceutically acceptable salt thereof,
- wherein:
- R1 is selected halo, cyano, azido, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-(C0-C3 alkyl)-, (3- to 8-membered monocyclic or bicyclic heterocycle)-(C0-C3 alkyl)-, (6- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, RxO—(C0-C3 alkyl)-, RxS—(C0-C3 alkyl)-, (RxRyN)—(C0-C3 alkyl)-, RxO—C(O)—(C0-C3 alkyl)-, RxS—C(O)—(C0-C3 alkyl)-, (RxRyN) C(O)—(C0-C3 alkyl)-, RxO—S(O)2—(C0-C3 alkyl)-, (RxRyN)S(O)2—(C0-C3 alkyl)-, RzC(O)—O—(C0-C3 alkyl)-, RzC(O)—(RxN)—(C0-C3 alkyl)-, RzS(O)2—O—(C0-C3 alkyl)-, RzS(O)2—(RxN)—(C0-C3 alkyl)-, RzC(O)—(C0-C6 alkyl)-, RzS(O)—(C0-C3 alkyl)-, and RzS(O)2—(C0-C3 alkyl)-;
- n is 0, 1, or 2;
- p is 1, 2, 3, 4, or 5;
- Ar1 is 6- to 10-membered monocyclic or bicyclic aryl or 5- to 10-membered monocyclic or bicyclic heteroaryl, wherein Ar1 is optionally substituted with one or more Z groups as allowed by valency;
- Z is selected from hydrogen, halo, cyano, azido, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, (C3-C6 cycloalkyl)-(C0-C3 alkyl)-, (3- to 8-membered monocyclic or bicyclic heterocycle)-(C0-C3 alkyl)-, (6- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, RxO—(C0-C3 alkyl)-, RxS—(C0-C3 alkyl)-, (RxRyN)—(C0-C3 alkyl)-, RxO—C(O)—(C0-C3 alkyl)-, RxS—C(O)—(C0-C3 alkyl)-, (RxRyN) C(O)—(C0-C3 alkyl)-, RxO—S(O)2—(C0-C3 alkyl)-, (RxRyN) S(O)2—(C0-C3 alkyl)-, RzC(O)—O—(C0-C3 alkyl)-, RzC(O)—(RxN)—(C0-C3 alkyl)-, RzS(O)2—O—(C0-C3 alkyl)-, RzS(O)2—(RzN)—(C0-C3 alkyl)-, RzC(O)—(C0-C6 alkyl)-, RzS(O)—(C0-C3 alkyl)-, and RzS(O)2—(C0-C3 alkyl)-;
- Rx and Ry are independently selected at each occurrence from hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C0-C3 alkyl)-, (4- to 6-membered heterocycle)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, and (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, each of which may be optionally substituted with one or more Y groups as allowed by valency;
- Rz is independently selected at each occurrence from hydrogen, halo, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C0-C3 alkyl)-, (4- to 6-membered heterocycle)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic aryl)-(C0-C3 alkyl)-, (5- to 10-membered monocyclic or bicyclic heteroaryl)-(C0-C3 alkyl)-, —ORx, —SRx, and —NRxRy, each of which may be optionally substituted with one or more Y groups as allowed by valency;
- and
- Y is independently selected at each occurrence from alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aldehyde, amino, carboxylic acid, ester, ether, halo, hydroxy, keto, nitro, cyano, azido, oxo, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, sulfonylamino, or thiol.
8 more elements
A compound selected from:
- or a pharmaceutically acceptable salt or derivative thereof.
Dependencies are inferred from the claim text.