NZ807753A - 2,4-diaminoquinazoline derivatives and medical uses thereof - Google Patents
2,4-diaminoquinazoline derivatives and medical uses thereofInfo
- Publication number
- NZ807753A NZ807753A NZ807753A NZ80775319A NZ807753A NZ 807753 A NZ807753 A NZ 807753A NZ 807753 A NZ807753 A NZ 807753A NZ 80775319 A NZ80775319 A NZ 80775319A NZ 807753 A NZ807753 A NZ 807753A
- Authority
- NZ
- New Zealand
- Prior art keywords
- fluorine
- methyl
- hydrogen
- deuterium
- cyclopropyl
- Prior art date
Links
- XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical class C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 title 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 12
- 239000011737 fluorine Substances 0.000 claims abstract 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract 8
- 229910052805 deuterium Inorganic materials 0.000 claims abstract 8
- 150000001408 amides Chemical class 0.000 claims abstract 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 150000002825 nitriles Chemical class 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 239000000460 chlorine Substances 0.000 claims abstract 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims abstract 2
- -1 methoxy, cyclopropyl Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 241000700605 Viruses Species 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
Abstract
This application relates to quinazoline derivatives of formula (I), pharmaceutical compositions comprising the compounds of formula (I), and the use of the compounds of formula (I) in the treatment or prevention of a viral infection, of a virus-induced disease, of cancer or of an allergy. In formula (I), R1is a C3-8alkyl, optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, amino, nitrile, ester, amide, C1-3alkyl, or C1-3alkoxy, the carbon of R1bonded to the amine in the 4-position of the quinazoline is in (R)-configuration, R2is 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, R3is hydrogen or deuterium, R4is hydrogen, deuterium, fluorine, methyl, carboxylic ester, carboxylic amide, nitrile, cyclopropyl, C4-7heterocycle, or 5-membered heteroaryl group, wherein each of methyl, cyclopropyl, C4-7heterocycle and 5-membered heteroaryl group is optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, or methyl, R5is hydrogen, deuterium, fluorine, chlorine, methyl, or methoxy, provided that at least one of R2, R3, R4and R5is not hydrogen.
Claims (3)
1. A compound of formula (I) R R2 NH N R4' N NH2 r5 (I) 5 or a pharmaceutically acceptable salt, solvate or polymorph thereof, wherein Ri is a Cs-salkyl, optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, amino, nitrile, ester, amide, Ci-salkyl, or Ci-salkoxy, the carbon of Ri bonded to the amine in the 4-position of the quinazoline is in (R)-configuration, R2 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, Rs is hydrogen or deuterium, R4 is hydrogen, deuterium, fluorine, methyl, carboxylic ester, carboxylic amide, nitrile, cyclopropyl, C4-7heterocycle, or5-membered heteroaryl group, wherein each of methyl, cyclopropyl, C4-7heterocycle and 5-membered heteroaryl group is optionally substituted by one or more substituents independently selected from fluorine, hydroxyl, or methyl, 10 15 20 and - Rs is hydrogen, deuterium, fluorine, chlorine, methyl, or methoxy provided that at least one of R2, Rs, R4 and Rs is not hydrogen. 25
2. The compound of claim 1, wherein Ri is a C4-8 alkyl substituted with a hydroxyl.
3. The compound of claim 1 or 2, wherein Ri is of formula (II): WO
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ807753A true NZ807753A (en) |
Family
ID=
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