US 11,939,319 B2
Pyridinyl and pyrazinyl-(asa)indolsulfonamides
Cecile Pegurier, Uccle (BE); Laurent Provins, Soignies (BE); Alvaro Cardenas, Tervuren (BE); Marie Ledecq, Eghezee (BE); Christa E. Mueller, Bonn (DE); Joerg Hockemeyer, Bonn (DE); Ali El-Tayeb, Bonn (DE); Nader Boshta, Bonn (DE); and Mahmoud Rashed, Bonn (DE)
Assigned to UCB PHARMA GMBH, Monheim (DE)
Appl. No. 17/058,845
Filed by UCB Pharma GmbH, Monheim (DE)
PCT Filed Jun. 18, 2019, PCT No. PCT/EP2019/065967
§ 371(c)(1), (2) Date Nov. 25, 2020,
PCT Pub. No. WO2019/243303, PCT Pub. Date Dec. 26, 2019.
Claims priority of application No. 18178429 (EP), filed on Jun. 19, 2018; and application No. 19157936 (EP), filed on Feb. 19, 2019.
Prior Publication US 2021/0206749 A1, Jul. 8, 2021
Int. Cl. C07D 403/12 (2006.01); C07D 401/12 (2006.01); C07D 471/04 (2006.01)
CPC C07D 403/12 (2013.01) [C07D 401/12 (2013.01); C07D 471/04 (2013.01)] 34 Claims
 
1. A compound of Formula I

OG Complex Work Unit Chemistry
wherein
X1 is N or C(R7),
R2 and R4 are independently selected from hydrogen or fluoro,
R5 is hydrogen or halogen,
R6 is selected from halogen, cyano, C3-5 cycloalkyl, C3-5 cycloalkylmethoxy, phenyloxy, benzyloxy, benzylmethoxy, pyridinylmethoxy, C1-3 alkoxy and C1-3 alkyl, wherein each cycloalkyl, benzyl, pyridinyl, alkyl and alkoxy can be substituted with one or more substituent selected from halogen, cyano, C1-2alkoxy and fluoroC1-2alkoxy, or
R6 together with R7 and the C-atoms to which they are attached form a five or six-membered aromatic or non-aromatic ring which may comprise one or two ring forming heteroatoms, wherein said ring is unsubstituted or substituted with one to three residues R13,
R7, if present, is selected from hydrogen, halogen, cyclopropyl, cyclopropyloxy, C1-3 alkoxy, and C1-3 alkyl, wherein each alkyl and alkoxy can be substituted with one or more substituent selected from halogen, C1-2 alkoxy, fluoro(C1-2)alkoxy and cyano, or R7 forms a ring together with R6 as described above,
R8 is selected from hydrogen, halogen, methoxy, ethoxy, fluoromethoxy and fluoroethoxy,
R10 is selected from hydrogen, cyano, halogen, C3-5 cycloalkyl, C3-5 cycloalkyloxy, C3-5 cycloalkylmethoxy, C1-4 alkoxy, and C1-4 alkyl, wherein each cycloalkyl, cycloalkyloxy, alkyl and alkoxy can be substituted with one or more substituent selected from halogen, C1-3 alkoxy, fluoro(C1-3)alkoxy and cyano,
R11 is selected from hydrogen, fluoro and methoxy,
X2 is N or C(R12),
R12 is selected from hydrogen, methoxy and halogen,
R13, in each occurrence, is independently selected from halogen, hydroxy, cyano, methyl, methoxy, fluoromethyl and fluoromethoxy,
or a pharmaceutically acceptable salt, solvate, isotope or co-crystal thereof.