US 12,006,316 B2
9H-pyrrolo-dipyridine derivatives
Joel Mercier, Brussels (BE); Laurent Provins, Brussels (BE); Celine Vermeiren, Brussels (BE); and Yogesh Anil Sabnis, Brussels (BE)
Assigned to UCB BIOPHARMA SRL, Brussels (BE)
Filed by UCB Biopharma SPRL, Brussels (BE)
Filed on Mar. 21, 2022, as Appl. No. 17/700,075.
Application 17/700,075 is a continuation of application No. 16/749,537, filed on Jan. 22, 2020, granted, now 11,312,716.
Application 16/749,537 is a continuation of application No. 15/547,980, abandoned, previously published as PCT/EP2016/051993, filed on Jan. 29, 2016.
Claims priority of application No. 15153448 (EP), filed on Feb. 2, 2015.
Prior Publication US 2022/0213103 A1, Jul. 7, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 471/14 (2006.01); A61K 31/437 (2006.01); A61K 51/04 (2006.01); C07B 59/00 (2006.01)
CPC C07D 471/14 (2013.01) [A61K 51/0455 (2013.01); A61K 51/0459 (2013.01); A61K 51/0463 (2013.01); C07B 59/002 (2013.01); C07B 2200/05 (2013.01)] 4 Claims
 
1. A compound of general formula I-A, or a pharmaceutically acceptable acid addition salt, a racemic mixture or its corresponding enantiomer and/or optical isomers thereof,

OG Complex Work Unit Chemistry
wherein
R1 is pyrazole, thiazole, pyridine, or pyrimidine each of which is optionally substituted by one or two substituents independently selected from (1) fluorine; (2) methyl, ethyl or propyl, each of which is optionally substituted by fluorine or methoxy; (3) cyano; (4) amino optionally substituted by methyl or fluoro-ethyl; (5) —C(O)NHR1A where R1A is methyl, ethyl, or propyl, each of which is optionally substituted by fluorine or methoxy; (6) methoxy, ethoxy or propoxy, each of which is optionally substituted by fluorine or methoxy; or (7) morpholine, piperazine or piperidine, each of which is optionally substituted by fluorine or fluoromethyl;
M is C—R3, and Q is CH; or M is CH, and Q is CR3;
R3 is (1) H; (2) fluorine; (3) methyl, ethyl or propyl, each of which is optionally substituted by fluorine, hydroxy or methoxy; (4) methoxy, ethoxy or propoxy, each of which is optionally substituted by fluorine, hydroxyl or methoxy; (4) di-methyl-amino; or (5) —NHR3A where R3A is methyl, ethyl or propyl, each of which is optionally substituted by fluorine, hydroxy or methoxy; and
wherein
any hydrogen of formula I-A is H, 2H or 3H;
any carbon of formula I-A is C, 14C or 11C; and
any fluorine of formula I-A is F or 18F;
provided that the compound of formula I is not a compound of general formula Ro I

OG Complex Work Unit Chemistry
wherein
R is hydrogen or tritium;
F is fluoro or 18fluoro;
or a pharmaceutically acceptable acid addition salt thereof.