ES2946632T7 - Moduladores de AhR - Google Patents

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Publication number

ES2946632T7

ES2946632T7 ES19706135T ES19706135T ES2946632T7 ES 2946632 T7 ES2946632 T7 ES 2946632T7 ES 19706135 T ES19706135 T ES 19706135T ES 19706135 T ES19706135 T ES 19706135T ES 2946632 T7 ES2946632 T7 ES 2946632T7

Authority

ES

Spain

Prior art keywords

methyl

trifluoromethyl

phenyl

quinazolin

pyrazin

Prior art date

2018-02-06

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.)

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• 150000001875 compounds Chemical class 0.000 claims description 413
• -1 -Rc Chemical compound 0.000 claims description 255
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 125000000217 alkyl group Chemical group 0.000 claims description 62
• 229910052736 halogen Inorganic materials 0.000 claims description 55
• 150000002367 halogens Chemical class 0.000 claims description 55
• 125000001800 methanetriyl group Chemical group C(*)(*)* 0.000 claims description 55
• 125000001188 haloalkyl group Chemical group 0.000 claims description 48
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 42
• 229910052805 deuterium Inorganic materials 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 41
• 206010028980 Neoplasm Diseases 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 238000000034 method Methods 0.000 claims description 27
• 125000005345 deuteroalkyl group Chemical group 0.000 claims description 25
• 150000002431 hydrogen Chemical group 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 17
• 229910003827 NRaRb Inorganic materials 0.000 claims description 16
• 201000011510 cancer Diseases 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 238000005304 joining Methods 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• SLOIOJSQOAGCTD-UHFFFAOYSA-N 7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-5,6-dihydro-1H-pyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCOC2=C(NN=C2)C1=O SLOIOJSQOAGCTD-UHFFFAOYSA-N 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• 229910052702 rhenium Inorganic materials 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 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 description 3
• MTVLDGFPDCLNDG-UHFFFAOYSA-N 2-(2-hydroxyethyl)-7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCOC2=CN(CCO)N=C2C1=O MTVLDGFPDCLNDG-UHFFFAOYSA-N 0.000 claims description 3
• FZGPQYYATGQSSF-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-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=CC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1 FZGPQYYATGQSSF-UHFFFAOYSA-N 0.000 claims description 3
• BIPARQSAIHCUAT-UHFFFAOYSA-N 3-methyl-5-[2-methyl-4-[6-(trifluoromethyl)quinolin-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=C2)C(F)(F)F)N=C1 BIPARQSAIHCUAT-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• HOUKNWJYGSYPCL-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-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=CC=C3N=C(C=CC3=N2)C(F)(F)F)N=C1 HOUKNWJYGSYPCL-UHFFFAOYSA-N 0.000 claims description 3
• OOSNLRQCZFXYIY-UHFFFAOYSA-N 6-methyl-7-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydro-1H-pyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CC1COC2=C(NN=C2)C(=O)N1C1=C(C)C=C(C=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F OOSNLRQCZFXYIY-UHFFFAOYSA-N 0.000 claims description 3
• NFKJSNDCXKGULS-UHFFFAOYSA-N 7-[2,5-dimethyl-4-[8-methyl-6-(trifluoromethyl)-1,5-naphthyridin-2-yl]phenyl]-1-methyl-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=C(C)C=C(C(C)=C1)C1=CC=C2N=C(C=C(C)C2=N1)C(F)(F)F NFKJSNDCXKGULS-UHFFFAOYSA-N 0.000 claims description 3
• NFVGZVKNWHNHRV-UHFFFAOYSA-N 7-[2-fluoro-5-methyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-2-yl]phenyl]-1-methyl-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=C(F)C=C(C(C)=C1)C1=CC=C2N=C(C=CC2=N1)C(F)(F)F NFVGZVKNWHNHRV-UHFFFAOYSA-N 0.000 claims description 3
• QEZCIGPHOAOYDY-UHFFFAOYSA-N 7-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydro-1H-pyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CC1=C(C=CC(=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F)N1CCOC2=C(NN=C2)C1=O QEZCIGPHOAOYDY-UHFFFAOYSA-N 0.000 claims description 3
• SYQMIXBCMCBVMU-UHFFFAOYSA-N 7-[4-(6-fluoro-1,5-naphthyridin-2-yl)-2-methylphenyl]-1-methyl-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound FC1=CC=C2C(=N1)C=CC(C1=CC=C(N3CCOC4=C(C3=O)N(N=C4)C)C(C)=C1)=N2 SYQMIXBCMCBVMU-UHFFFAOYSA-N 0.000 claims description 3
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• HVJATGPYGZTSDN-UHFFFAOYSA-N 1-(2-hydroxyethyl)-7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCOC2=C(N(CCO)N=C2)C1=O HVJATGPYGZTSDN-UHFFFAOYSA-N 0.000 claims description 2
• TUCPAWRTLASBHJ-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-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=CC=C2N=C(C=CC2=N1)C(F)(F)F TUCPAWRTLASBHJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• RPPGDRAWWBQDFM-UHFFFAOYSA-N 1-methyl-6-[2-methyl-4-[8-methyl-6-(trifluoromethyl)-1,5-naphthyridin-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=CC=C2N=C(C=C(C)C2=N1)C(F)(F)F RPPGDRAWWBQDFM-UHFFFAOYSA-N 0.000 claims description 2
• NOIVWFQNDZCSBZ-UHFFFAOYSA-N 1-methyl-7-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=C(C)C=C(C=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F NOIVWFQNDZCSBZ-UHFFFAOYSA-N 0.000 claims description 2
• SYNPEQNJNFKRSG-UHFFFAOYSA-N 1-methyl-7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=C(C)C=C(C=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F SYNPEQNJNFKRSG-UHFFFAOYSA-N 0.000 claims description 2
• XPTNWXDHOLURQB-UHFFFAOYSA-N 1-methyl-7-[2-methyl-4-[8-methyl-6-(trifluoromethyl)-1,5-naphthyridin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=C(C)C=C(C=C1)C1=CC=C2N=C(C=C(C)C2=N1)C(F)(F)F XPTNWXDHOLURQB-UHFFFAOYSA-N 0.000 claims description 2
• NWHCZXIIEISZGK-UHFFFAOYSA-N 1-methyl-7-[4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1N=CC2=C1C(=O)N(CCO2)C1=CC=C(C=C1)C1=NC=C2N=C(C=CC2=N1)C(F)(F)F NWHCZXIIEISZGK-UHFFFAOYSA-N 0.000 claims description 2
• ZBPTZYJEIDIBAV-UHFFFAOYSA-N 2-[7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-8-oxo-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-1-yl]acetonitrile Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCOC2=C(C1=O)N(N=C2)CC#N ZBPTZYJEIDIBAV-UHFFFAOYSA-N 0.000 claims description 2
• AGVXPENMAWXGAD-UHFFFAOYSA-N 2-[7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-8-oxo-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-2-yl]acetonitrile Chemical compound CC1=C(C=CC(=C1)C1=NC2=CC=C(C=C2C=N1)C(F)(F)F)N1CCOC2=CN(CC#N)N=C2C1=O AGVXPENMAWXGAD-UHFFFAOYSA-N 0.000 claims description 2
• NKGRJKOBAHXMJZ-UHFFFAOYSA-N 2-methyl-7-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydropyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound CN1C=C2OCCN(C3=C(C)C=C(C=C3)C3=NC=C4N=C(C=CC4=N3)C(F)(F)F)C(=O)C2=N1 NKGRJKOBAHXMJZ-UHFFFAOYSA-N 0.000 claims description 2
• CNFOSZBUFXORFX-UHFFFAOYSA-N 2-methyl-7-[2-methyl-4-[6-(trifluoromethyl)pyrido[3,2-d]pyrimidin-2-yl]phenyl]-5,6-dihydrotriazolo[4,5-f][1,4]oxazepin-8-one Chemical compound C(F)(F)(F)C1=NC2=C(C=C1)N=C(N=C2)C1=CC(=C(N2CCOC=3C(C2=O)=NN(N=3)C)C=C1)C CNFOSZBUFXORFX-UHFFFAOYSA-N 0.000 claims description 2
• UACNTBPAYGUSNB-UHFFFAOYSA-N 2-methyl-7-[2-methyl-4-[6-(trifluoromethyl)quinazolin-2-yl]phenyl]-5,6-dihydrotriazolo[4,5-f][1,4]oxazepin-8-one Chemical compound C(F)(F)(F)C1=CC2=CN=C(N=C2C=C1)C1=CC(=C(C=C1)N1CCOC=2C(C1=O)=NN(N=2)C)C UACNTBPAYGUSNB-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• IGVVBHZVOAIMEE-UHFFFAOYSA-N 5-[2,5-dimethyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-2-yl]phenyl]-3-methyl-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one Chemical compound C1N(C2=C(C=C(C3=NC4=C(N=C(C=C4)C(F)(F)F)C=C3)C(C)=C2)C)C(=O)C=2N(C1)N=CC=2C IGVVBHZVOAIMEE-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• ZTYGPQWWYUYYLH-UHFFFAOYSA-N 5-[2,5-dimethyl-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(C)C=C(C(C)=C2)C2=NC3=CC=C(C=C3C=C2)C(F)(F)F)N=C1 ZTYGPQWWYUYYLH-UHFFFAOYSA-N 0.000 claims description 2
• KXNUDQCFPVJLRM-UHFFFAOYSA-N 5-[2,5-dimethyl-4-[8-methyl-6-(trifluoromethyl)-1,5-naphthyridin-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=CC=C3N=C(C=C(C)C3=N2)C(F)(F)F)N=C1 KXNUDQCFPVJLRM-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• PZTZFKGXBPRMDR-UHFFFAOYSA-N 5-[2-fluoro-5-methyl-4-[8-methyl-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=C(C)C=C(C=C3C=N2)C(F)(F)F)N=C1 PZTZFKGXBPRMDR-UHFFFAOYSA-N 0.000 claims description 2
• CIVRRIJUBWNZRD-UHFFFAOYSA-N 6-methyl-7-[2-methyl-4-[6-(trifluoromethyl)-1,5-naphthyridin-2-yl]phenyl]-5,6-dihydro-1H-pyrazolo[3,4-f][1,4]oxazepin-8-one Chemical compound C1=C(C(=CC=C1C1=NC2=C(C=C1)N=C(C=C2)C(F)(F)F)N1C(COC2=C(C1=O)NN=C2)C)C CIVRRIJUBWNZRD-UHFFFAOYSA-N 0.000 claims description 2
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• 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
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