JPWO2019156987A5 - - Google Patents
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- Publication number
- JPWO2019156987A5 JPWO2019156987A5 JP2020564046A JP2020564046A JPWO2019156987A5 JP WO2019156987 A5 JPWO2019156987 A5 JP WO2019156987A5 JP 2020564046 A JP2020564046 A JP 2020564046A JP 2020564046 A JP2020564046 A JP 2020564046A JP WO2019156987 A5 JPWO2019156987 A5 JP WO2019156987A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- trifluoromethyl
- quinazoline
- pyrazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 dehydrogen Chemical class 0.000 claims 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 229910052805 deuterium Inorganic materials 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- PFRVYMDGPIPJAM-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1CO PFRVYMDGPIPJAM-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- OYBNNAHIBWBZDW-UHFFFAOYSA-N 1-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4H-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CN1N=CC2=C1C(N(C2)C1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)C)=O OYBNNAHIBWBZDW-UHFFFAOYSA-N 0.000 claims 1
- PUTWQCNJUYXTIW-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CN1N=CC2=C1C(=O)N(CC2)C1=C(C)C=C(C=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F PUTWQCNJUYXTIW-UHFFFAOYSA-N 0.000 claims 1
- FKTPQGMKXGVOHC-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CN1N=CC2=C1C(=O)N(CC2)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F FKTPQGMKXGVOHC-UHFFFAOYSA-N 0.000 claims 1
- JXZKCKUHQQQSPM-UHFFFAOYSA-N 2-(1-hydroxyethyl)-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC(O)C1=NN2CCN(C(=O)C2=C1C)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F JXZKCKUHQQQSPM-UHFFFAOYSA-N 0.000 claims 1
- VELZXAUJLOSHTJ-UHFFFAOYSA-N 2-(1-hydroxyethyl)-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC(O)C1=NN2CCN(C(=O)C2=C1)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F VELZXAUJLOSHTJ-UHFFFAOYSA-N 0.000 claims 1
- SBCGNUJMEPGUOQ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1OCCO SBCGNUJMEPGUOQ-UHFFFAOYSA-N 0.000 claims 1
- DOMYQQXKKVPHEE-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1CO DOMYQQXKKVPHEE-UHFFFAOYSA-N 0.000 claims 1
- OCTOHEWSNWPWBG-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CN(C)CC1=NN2C(C(N(CC2)C2=C(C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)C)=O)=C1C OCTOHEWSNWPWBG-UHFFFAOYSA-N 0.000 claims 1
- XHFOQWQDYDSNPE-UHFFFAOYSA-N 2-[3-methyl-4-(3-methyl-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazin-5-yl)phenyl]-6-(trifluoromethyl)-3H-quinazolin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C(O)=N2)C(F)(F)F)N=C1 XHFOQWQDYDSNPE-UHFFFAOYSA-N 0.000 claims 1
- AGDKQIPDOYTWSH-UHFFFAOYSA-N 2-[3-methyl-4-(3-methyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-5-yl)phenyl]-6-(trifluoromethyl)quinazoline Chemical compound CC1=C2CN(CCN2N=C1)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F AGDKQIPDOYTWSH-UHFFFAOYSA-N 0.000 claims 1
- VDXULRSTOWLGIW-UHFFFAOYSA-N 2-amino-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound C1N(C2=C(C=C(C3=NC4=C(C=C(C(F)(F)F)C=C4)C=N3)C=C2)C)C(=O)C=2N(C1)N=C(C=2C)N VDXULRSTOWLGIW-UHFFFAOYSA-N 0.000 claims 1
- NBJDSMIOWPVWRW-UHFFFAOYSA-N 2h-oxazepin-5-one Chemical compound O=C1C=CNOC=C1 NBJDSMIOWPVWRW-UHFFFAOYSA-N 0.000 claims 1
- MCAWQFLEZNDIFH-UHFFFAOYSA-N 3-(hydroxymethyl)-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(CO)=C2C1=O MCAWQFLEZNDIFH-UHFFFAOYSA-N 0.000 claims 1
- QOVUJPHZXVFRBD-HNNXBMFYSA-N 3-[[(2S)-1-hydroxypropan-2-yl]amino]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound OC[C@H](C)NC=1C=NN2C=1C(N(CC2)C1=C(C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)C)=O QOVUJPHZXVFRBD-HNNXBMFYSA-N 0.000 claims 1
- JILITWPKEMFBKQ-UHFFFAOYSA-N 3-bromo-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(Br)=C2C1=O JILITWPKEMFBKQ-UHFFFAOYSA-N 0.000 claims 1
- ZDIAZQIDIJNOEG-UHFFFAOYSA-N 3-methyl-2-[(2-methylmorpholin-4-yl)methyl]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1CN(CC2=NN3CCN(C(=O)C3=C2C)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)CCO1 ZDIAZQIDIJNOEG-UHFFFAOYSA-N 0.000 claims 1
- NNLFSAPLQFXJGJ-UHFFFAOYSA-N 3-methyl-2-[(4-methyl-3-oxopiperazin-1-yl)methyl]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CN1CCN(CC2=NN3CCN(C(=O)C3=C2C)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)CC1=O NNLFSAPLQFXJGJ-UHFFFAOYSA-N 0.000 claims 1
- FXIYOTIFIPOEBD-UHFFFAOYSA-N 3-methyl-2-[(4-methylpiperazin-1-yl)methyl]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CN1CCN(CC2=NN3CCN(C(=O)C3=C2C)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)CC1 FXIYOTIFIPOEBD-UHFFFAOYSA-N 0.000 claims 1
- ZDIAZQIDIJNOEG-GOSISDBHSA-N 3-methyl-2-[[(2R)-2-methylmorpholin-4-yl]methyl]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound C[C@@H]1CN(CC2=NN3CCN(C(=O)C3=C2C)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)CCO1 ZDIAZQIDIJNOEG-GOSISDBHSA-N 0.000 claims 1
- ZDIAZQIDIJNOEG-SFHVURJKSA-N 3-methyl-2-[[(2S)-2-methylmorpholin-4-yl]methyl]-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound C[C@H]1CN(CC2=NN3CCN(C(=O)C3=C2C)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)CCO1 ZDIAZQIDIJNOEG-SFHVURJKSA-N 0.000 claims 1
- NOOHRCKSZFAAPH-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1 NOOHRCKSZFAAPH-UHFFFAOYSA-N 0.000 claims 1
- SDGLFZIVGXZTNL-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-2-(1-morpholin-4-ylethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC(N1CCOCC1)C1=NN2CCN(C(=O)C2=C1C)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F SDGLFZIVGXZTNL-UHFFFAOYSA-N 0.000 claims 1
- CIRBYCUHXHTEPS-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-2-carboxylic acid Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1C(O)=O CIRBYCUHXHTEPS-UHFFFAOYSA-N 0.000 claims 1
- BIYNCLTYHBVOOO-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1 BIYNCLTYHBVOOO-UHFFFAOYSA-N 0.000 claims 1
- FYUKTXJTSANEMT-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-7-(phenylmethoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(N=C1)C(COCC1=CC=CC=C1)CN(C2=O)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F FYUKTXJTSANEMT-UHFFFAOYSA-N 0.000 claims 1
- IWSHVALGOJPFGJ-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[8-methyl-6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C=C2)C2=NC3=C(C)C=C(C=C3C=N2)C(F)(F)F)N=C1 IWSHVALGOJPFGJ-UHFFFAOYSA-N 0.000 claims 1
- STUSSRBRICYOEP-UHFFFAOYSA-N 4-[5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazin-3-yl]morpholin-3-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1C(C=2N(CC1)N=CC=2N1C(COCC1)=O)=O STUSSRBRICYOEP-UHFFFAOYSA-N 0.000 claims 1
- QFCPBXRZWVOQBU-UHFFFAOYSA-N 5-[2,5-dimethyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(C)C=C(C(C)=C2)C2=NC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1 QFCPBXRZWVOQBU-UHFFFAOYSA-N 0.000 claims 1
- SEAGLYUMAAXXHP-UHFFFAOYSA-N 5-[2-fluoro-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(F)C=C(C=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1 SEAGLYUMAAXXHP-UHFFFAOYSA-N 0.000 claims 1
- NXFIWWNKAYJDKY-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(F)C=C(C(C)=C2)C2=NC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1 NXFIWWNKAYJDKY-UHFFFAOYSA-N 0.000 claims 1
- UIYMHHXRICCKGM-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(F)C=C(C(C)=C2)C2=NC3=CC=C(C=C3C=N2)C(F)(F)F)N=C1 UIYMHHXRICCKGM-UHFFFAOYSA-N 0.000 claims 1
- PJCADMKSGYVJDS-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-[6-(trifluoromethyl)quinolin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(CCN(C2=O)C2=C(F)C=C(C(C)=C2)C2=NC3=CC=C(C=C3C=C2)C(F)(F)F)N=C1 PJCADMKSGYVJDS-UHFFFAOYSA-N 0.000 claims 1
- IIHBGQGDMFJDBL-UHFFFAOYSA-N 5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-3-(morpholin-4-ylmethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(CN3CCOCC3)=C2C1=O IIHBGQGDMFJDBL-UHFFFAOYSA-N 0.000 claims 1
- HGXVALSDTDULEV-UHFFFAOYSA-N 5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-3-morpholin-4-yl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(N3CCOCC3)=C2C1=O HGXVALSDTDULEV-UHFFFAOYSA-N 0.000 claims 1
- FKRCSVGTHXVTET-UHFFFAOYSA-N 5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-3-carbonitrile Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1C(C=2N(CC1)N=CC=2C#N)=O FKRCSVGTHXVTET-UHFFFAOYSA-N 0.000 claims 1
- IBRYQLLSBUXSCT-UHFFFAOYSA-N 5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-3-carboxamide Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1C(C=2N(CC1)N=CC=2C(=O)N)=O IBRYQLLSBUXSCT-UHFFFAOYSA-N 0.000 claims 1
- CLFUSSMZYHJWLB-UHFFFAOYSA-N 5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-3-carboxylic acid Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(C(O)=O)=C2C1=O CLFUSSMZYHJWLB-UHFFFAOYSA-N 0.000 claims 1
- HWOQQRPVZFWTHL-UHFFFAOYSA-N 5-[5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazin-3-yl]imidazolidine-2,4-dione Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCN2N=CC(C3NC(=O)NC3=O)=C2C1=O HWOQQRPVZFWTHL-UHFFFAOYSA-N 0.000 claims 1
- AJLJHIBXWBQRTR-UHFFFAOYSA-N 7-(hydroxymethyl)-3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound CC1=C2N(N=C1)C(CO)CN(C2=O)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F AJLJHIBXWBQRTR-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
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2019
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2020
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