Granted Patent B2

US 12,709,605 · App. 18/785,279 · Granted Aug 18, 2026

Inventors: Luca Gobbi (Basel, CH); Uwe Grether (Basel, CH); Julian Kretz (Basel, CH); Simon M. Ametamey (Zurich, CH)

Assignees: HOFFMANN-LA ROCHE INC.; ETH ZUERICH

C07D401/04

Abstract

Claims (20)

1 . A process for the preparation of a compound comprising one of the following steps:

(a) the reaction of a compound of formula (A)

in the presence of R 1 —H, a palladium catalyst and a base;

(b) the reaction of a compound of formula (B)

in the presence of NH 2 —C(R 2 R 3 )-A 2 -O—(CH 2 ) n —(CD 2 ) m -X, a coupling agent and a base, wherein:

R 1 is alkoxyazetidinyl, dihaloazetidinyl or pyrrolidinyl;

R 2 and R 3 are independently selected from hydrogen and alkyl;

A 1 is —CH— or nitrogen;

A 2 is —CH 2 — or carbonyl;

X is halogen;

Y is halogen;

n is 0 to 3; and

m is 0 or 1;

provided that m and n are not both 0 at the same time.

2 . The process of claim 1 , wherein R 1 is methoxyazetidinyl, difluoroazetidinyl or pyrrolidinyl.

3 . The process of claim 1 , wherein R 2 and R 3 are independently selected from hydrogen, ethyl or butyl.

4 . The process of claim 3 , wherein R 2 and R 3 are both ethyl at the same time, or one of R 2 and R 3 is hydrogen and the other one is butyl.

5 . The process of claim 1 , wherein A 1 is —CH—.

6 . The process of claim 1 , wherein X is fluorine.

7 . The process of claim 1 , wherein n is 1, 2 or 3.

Priority Claims (1)

Continuity (3)

References Cited (64)