IP Library Granted Patent US 12,006,316
Granted Patent B2
US 12,006,316 · App. 17/700,075 · Granted Jun 11, 2024

9H-pyrrolo-dipyridine derivatives

Inventors: Joel Mercier (Brussels, BE); Laurent Provins (Brussels, BE); Celine Vermeiren (Brussels, BE); Yogesh Anil Sabnis (Brussels, BE)
Assignee: UCB BIOPHARMA SRL
C07D471/14A61K51/0455A61K51/0459A61K51/0463C07B59/002C07B2200/05
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Quick Facts
Patent No.
US 12,006,316
App. No.
17/700,075
Granted
Jun 11, 2024
Kind
B2
Abstract

The invention relates to 9H-pyrrolo-dipyridine derivatives of formula I, processes for preparing them, pharmaceutical compositions containing them and their use as radiopharmaceuticals in particular as imaging agents for the detection of Tau aggregates.

Claims (17)

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,

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, 2 H or 3 H;

any carbon of formula I-A is C, 14 C or 11 C; and

any fluorine of formula I-A is F or 18 F;

provided that the compound of formula I is not a compound of general formula Ro I

wherein

R is hydrogen or tritium;

F is fluoro or 18 fluoro;

or a pharmaceutically acceptable acid addition salt thereof.

2. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable excipient.

3. A method of diagnosing or monitoring tau aggregates in the brain of a subject, the method comprising administering a radiolabeled compound containing an isotope according to claim 1 to the subject.

4. A method of treating a subject with a neurodegenerative disease in which tau aggregates in the brain are implicated, the method comprising administering to the subject an effective amount of compound according to claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 17, 2024
From: MERCIER, JOEL; PROVINS, LAURENT; VERMEIREN, CELINE; SABNIS, YOGESH ANIL
To: UCB BIOPHARMA SPRL
Reel/Frame 066149/0442 →
CHANGE OF NAME Recorded Jan 17, 2024
From: UCB BIOPHARMA SPRL
To: UCB BIOPHARMA SRL
Reel/Frame 066340/0876 →
Priority Claims (1)
EP 15153448 · Feb 2, 2015 · regional
Continuity (3)
Continuation 16749537 · Jan 22, 2020
Continuation 15547980
Related Publication 20220213103A1 · Jul 7, 2022