US2023278964A1PendingUtilityA1
2,4-diaminoquinazoline derivatives and medical uses thereof
Assignee: JANSSEN SCIENCES IRELAND UNLIMITED COPriority: Mar 1, 2018Filed: Jan 24, 2023Published: Sep 7, 2023
Est. expiryMar 1, 2038(~11.6 yrs left)· nominal 20-yr term from priority
Inventors:David Craig Mc GowanWerner Constant Johan EmbrechtsJérôme Emile Georges GuillemontLudwig Paul CooymansTim Hugo Maria JonckersPierre Jean-Marie Bernard Raboisson
C07D 239/95A61K 31/517A61P 1/16A61P 31/12A61P 35/00A61P 37/06C07D 413/04
71
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Claims
Abstract
This application relates to quinazoline derivatives, processes for their preparation, pharmaceutical compositions, and medical uses thereof.
Claims
exact text as granted — not AI-modified1 - 15 . (canceled)
16 . A method of agonizing TLR-8 receptors in a subject suffering from a viral infection, comprising administering an effective amount of compound of formula (I) to the subject in need thereof, wherein formula (I) is represented by:
or a pharmaceutically acceptable salt or solvate thereof, wherein
R 1 is of formula (II):
wherein n is 0, 1, or 2;
or of formula (III):
wherein n is 0, 1, or 2,
the carbon of R 1 bonded to the amine in the 4-position of the quinazoline is in (R)-configuration,
R 2 is hydrogen, deuterium, fluorine, chlorine, methyl, methoxy, cyclopropyl, trifluoromethyl, or carboxylic amide, wherein each of methyl, methoxy and cyclopropyl is optionally substituted by one or more substituents independently selected from fluorine and nitrile,
R 3 is hydrogen or deuterium,
R 4 is hydrogen, deuterium, fluorine, methyl, carboxylic ester, carboxylic amide, nitrile, cyclopropyl, C 4-7 heterocycle, or 5-membered heteroaryl group, wherein each of methyl, cyclopropyl, C 4-7 heterocycle and 5-membered heteroaryl group is optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, or methyl,
and
R 5 is hydrogen, deuterium, fluorine, chlorine, methyl, or methoxy,
provided that at least one of R 2 , R 3 , R 4 and R 5 is not hydrogen.
17 . The method of claim 16 , wherein R 1 is formula (II):
wherein n is 0, 1, or 2.
18 . The method of claim 17 , wherein n is 1.
19 . The method of claim 17 , wherein R 2 is fluorine, chlorine or methyl, and wherein methyl is optionally substituted by one or more substituents independently selected from fluorine and nitrile.
20 . The method of claim 17 , wherein R 2 is fluorine or chlorine.
21 . The method of claim 17 , wherein R 4 is fluorine or methyl, and wherein methyl is optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, or methyl.
22 . The method of claim 17 , wherein R 4 is fluorine.
23 . The method of claim 17 , wherein R 4 is hydrogen.
24 . The method of claim 17 , wherein R 3 and R 5 are hydrogen
25 . The method of claim 16 , wherein the compound of formula (I) is chosen from among compounds 1-34:
Compound
number
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
or a pharmaceutically acceptable salt or solvate thereof.
26 . The method of claim 25 , which is chosen from among compounds 1, 2, 3, 4, 5, 7, 9, 11, 12, 13, 14, 15, 16, 18, 19, 20, 21, 22, 23, 24 and 26 or a pharmaceutically acceptable salt or solvate thereof.
27 . The method of claim 25 , which is chosen from among compounds 2, 13, 14, 15, 16, 21 and 23 or a pharmaceutically acceptable salt or solvate thereof.
28 . The method of claim 25 , wherein the compound is 2, or a pharmaceutically acceptable salt or solvate thereof.
29 . The method of claim 25 , wherein the compound is 13, or a pharmaceutically acceptable salt or solvate thereof.
30 . The method of claim 25 , wherein the compound is 14, or a pharmaceutically acceptable salt or solvate thereof.
31 . The method of claim 25 , wherein the compound is 15, or a pharmaceutically acceptable salt or solvate thereof.
32 . The method of claim 25 , wherein the compound is 16, or a pharmaceutically acceptable salt or solvate thereof.
33 . The method of claim 25 , wherein the compound is 21, or a pharmaceutically acceptable salt or solvate thereof.
34 . The method of claim 25 , wherein the compound is 23, or a pharmaceutically acceptable salt or solvate thereof.
35 . The method of claim 16 , wherein the effective amount is an amount that is sufficient to stimulate or activate at least one of activity of TLR8 receptor and activate cytokine production (or secretion).Cited by (0)
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