US 11,926,614 B2
1,2,4-triazole derivatives as tankyrase inhibitors
Stefan Krauss, Eidsvoll Verk (NO); Marc Nazare, Berlin (DE); Lari Lehtio, Oulu (FI); Jo Waaler, Oslo (NO); Anita Wegert, Aldenhoven (DE); and Ruben Gerardus George Leenders, Nijmegen (NL)
Assigned to OSLO UNIVERSITETSSYKEHUS HF, Oslo (NO); FORSCHUNGSVERBUND BERLIN E.V., Berlin (DE); and UNIVERSITY OF OULU, Oulu (FI)
Appl. No. 17/253,668
Filed by OSLO UNIVERSITETSSYKEHUS HF, Oslo (NO); FORSCHUNGSVERBUND BERLIN E.V., Berlin (DE); and UNIVERSITY OF OULU, Oulu (FI)
PCT Filed Jun. 19, 2019, PCT No. PCT/GB2019/051728
§ 371(c)(1), (2) Date Dec. 18, 2020,
PCT Pub. No. WO2019/243822, PCT Pub. Date Dec. 26, 2019.
Claims priority of application No. 1810071 (GB), filed on Jun. 19, 2018.
Prior Publication US 2021/0269419 A1, Sep. 2, 2021
Int. Cl. C07D 401/14 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 417/04 (2006.01); C07D 417/14 (2006.01); C07D 471/04 (2006.01); C07D 487/04 (2006.01); C07D 491/048 (2006.01); C07D 495/04 (2006.01)
CPC C07D 401/14 (2013.01) [C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 417/04 (2013.01); C07D 417/14 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01); C07D 491/048 (2013.01); C07D 495/04 (2013.01); C07B 2200/07 (2013.01)] 23 Claims
 
1. A compound of general formula (I), or a tautomer, stereoisomer, pharmaceutically acceptable salt or pro-drug thereof:

OG Complex Work Unit Chemistry
wherein:
a dashed line indicates an optional bond;
X represents:
a 5- or 6-membered, unsaturated heterocyclic group optionally substituted by one or more substituents independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, —CN, —NO2, —N(R)2, and —SO2R (where each R is independently H or C1-6 alkyl;
a C3-5 cycloalkyl group optionally substituted by one or more substituents independently selected from C1-6 alkyl, C1-6 haloalkyl, and C1-6 alkoxy; or
an aryl group optionally substituted by one or more substituents independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, and C1-6 alkoxy;
Y represents:
an aryl or heteroaryl group optionally substituted by one or more substituents independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, and C1-6 alkoxy;
a 5- or 6-membered, saturated heterocyclic group optionally substituted by one or more substituents independently selected from C1-6 alkyl, C1-6 haloalkyl, and C1-6 alkoxy; or
a C3-6 cycloalkyl group optionally substituted by one or more substituents independently selected from C1-6 alkyl, C1-6 haloalkyl, and C1-6 alkoxy; and
Z represents:
an aryl group optionally substituted by one or more substituents independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, CN, —NO2,
—N2, and —SO2R (where each R is independently H or C1-6 alkyl; or
an unsaturated, 5- to 10-membered mono- or bicyclic heterocyclic group optionally substituted by one or more substituents independently selected from halogen, C1-6 alkyl, C1-6 haloalkyl, C1-6 alkoxy, —CN, —NO2, —N(R)2, and
—SO2R (where each R is independently H or C1-6 alkyl.