JP7474709B2 - Ａ２ａ／ａ２ｂ阻害剤としてのイミダゾピリミジン及びトリアゾロピリミジン - Google Patents
Ａ２ａ／ａ２ｂ阻害剤としてのイミダゾピリミジン及びトリアゾロピリミジン Download PDFInfo
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- JP7474709B2 JP7474709B2 JP2020567459A JP2020567459A JP7474709B2 JP 7474709 B2 JP7474709 B2 JP 7474709B2 JP 2020567459 A JP2020567459 A JP 2020567459A JP 2020567459 A JP2020567459 A JP 2020567459A JP 7474709 B2 JP7474709 B2 JP 7474709B2
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- alkyl
- cycloalkyl
- aryl
- membered heterocycloalkyl
- membered heteroaryl
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- 150000005237 imidazopyrimidines Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 1887
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 1067
- 125000001072 heteroaryl group Chemical group 0.000 claims description 888
- 125000003118 aryl group Chemical group 0.000 claims description 505
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 502
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 443
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 443
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 380
- 125000001424 substituent group Chemical group 0.000 claims description 305
- 229910052799 carbon Inorganic materials 0.000 claims description 267
- 229910052739 hydrogen Inorganic materials 0.000 claims description 240
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 156
- 125000003545 alkoxy group Chemical group 0.000 claims description 156
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 130
- -1 hydroxy(phenyl)methyl Chemical group 0.000 claims description 120
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 120
- 125000004429 atom Chemical group 0.000 claims description 102
- 125000005843 halogen group Chemical group 0.000 claims description 73
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 50
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 8
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 201000010536 head and neck cancer Diseases 0.000 claims 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- MNUAACPKOCGMKO-UHFFFAOYSA-N 3-[5-amino-2-(pyridin-2-ylmethyl)-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 MNUAACPKOCGMKO-UHFFFAOYSA-N 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- QPBDSJYCRGOCHW-UHFFFAOYSA-N 1-[[2-[[5-amino-7-(3-cyanophenyl)-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]methyl]-3-fluorophenyl]methyl]piperidine-4-carboxylic acid Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(CN2CCC(CC2)C(=O)O)C=CC=C1F)C1=NC=NC=C1)C1=CC(=CC=C1)C#N QPBDSJYCRGOCHW-UHFFFAOYSA-N 0.000 claims 1
- ZTOHVLOXNPNZJK-UHFFFAOYSA-N 2-[[5-amino-7-(3-cyanophenyl)-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]methoxy]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)COC1=C(C#N)C=CC=C1)C1=NC=NC=C1)C1=CC(=CC=C1)C#N ZTOHVLOXNPNZJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- LUZZXOOFSMMZCH-UHFFFAOYSA-N 3-(5-amino-2-benzoyl-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl)benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(=NN12)C(=O)C1=CC=CC=C1)C1=CC=NC=N1 LUZZXOOFSMMZCH-UHFFFAOYSA-N 0.000 claims 1
- MLCQMJNAMHROBK-UHFFFAOYSA-N 3-[5-amino-2-(1,2-benzoxazol-3-ylmethyl)-8-(2-ethylpyrazol-3-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NOC2=C1C=CC=C2)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 MLCQMJNAMHROBK-UHFFFAOYSA-N 0.000 claims 1
- VYSVEUJDUPGQJZ-UHFFFAOYSA-N 3-[5-amino-2-(cyclohexylmethyl)-8-(2-ethylpyrazol-3-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1CCCCC1)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 VYSVEUJDUPGQJZ-UHFFFAOYSA-N 0.000 claims 1
- MTEHSURJMREZTC-UHFFFAOYSA-N 3-[5-amino-2-(oxolan-3-yl)-8-pyridin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)C1COCC1)C1=CC=NC=C1)C=1C=C(C#N)C=CC=1 MTEHSURJMREZTC-UHFFFAOYSA-N 0.000 claims 1
- GGWRZXHESDQKEI-UHFFFAOYSA-N 3-[5-amino-2-(pyridin-2-ylmethyl)-8-quinolin-5-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=C2C=CC=NC2=CC=C1)C=1C=C(C#N)C=CC=1 GGWRZXHESDQKEI-UHFFFAOYSA-N 0.000 claims 1
- BUYBHIBILZRJJN-UHFFFAOYSA-N 3-[5-amino-2-[(1-methylpyrazol-3-yl)methyl]-8-(1,3-oxazol-5-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NN(C=C1)C)C1=CN=CO1)C=1C=C(C#N)C=CC=1 BUYBHIBILZRJJN-UHFFFAOYSA-N 0.000 claims 1
- USUJGMZEOPRMRJ-UHFFFAOYSA-N 3-[5-amino-2-[(2,6-difluorophenyl)-hydroxymethyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(=NN12)C(O)C1=C(F)C=CC=C1F)C1=CC=NC=N1 USUJGMZEOPRMRJ-UHFFFAOYSA-N 0.000 claims 1
- OKHNTKUQJHABCR-UHFFFAOYSA-N 3-[5-amino-2-[(2-fluorophenyl)-hydroxymethyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)C(O)C1=C(C=CC=C1)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 OKHNTKUQJHABCR-UHFFFAOYSA-N 0.000 claims 1
- RGXRSKKZHQSUBL-UHFFFAOYSA-N 3-[5-amino-2-[(2-fluorophenyl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 RGXRSKKZHQSUBL-UHFFFAOYSA-N 0.000 claims 1
- CEVHFJJWEKEUID-UHFFFAOYSA-N 3-[5-amino-2-[(2-hydroxyethylamino)-phenylmethyl]-8-pyridin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)C(C1=CC=CC=C1)NCCO)C1=CC=NC=C1)C=1C=C(C#N)C=CC=1 CEVHFJJWEKEUID-UHFFFAOYSA-N 0.000 claims 1
- WCQUAZLLKUQRRS-UHFFFAOYSA-N 3-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-8-[4-(hydroxymethyl)-2-methyl-1,3-oxazol-5-yl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C1=C(N=C(O1)C)CO)C=1C=C(C#N)C=CC=1 WCQUAZLLKUQRRS-UHFFFAOYSA-N 0.000 claims 1
- YHIYYOFHIDJOPL-UHFFFAOYSA-N 3-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(CC3=NC=CC=C3F)=NN12)C1=CC=NC=N1 YHIYYOFHIDJOPL-UHFFFAOYSA-N 0.000 claims 1
- QJLCTFZMTFDCKB-UHFFFAOYSA-N 3-[5-amino-2-[(3-hydroxyazetidin-1-yl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(CN3CC(O)C3)=NN12)C1=CC=NC=N1 QJLCTFZMTFDCKB-UHFFFAOYSA-N 0.000 claims 1
- HBVMWHDCCSNRSP-UHFFFAOYSA-N 3-[5-amino-2-[(3-methylpyridin-2-yl)methylamino]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound CC1=CC=CN=C1CNC1=NN2C(=N1)C(C1=CC=NC=N1)=C(N=C2N)C1=CC=CC(=C1)C#N HBVMWHDCCSNRSP-UHFFFAOYSA-N 0.000 claims 1
- ZCKITDLHOGMUTN-UHFFFAOYSA-N 3-[5-amino-2-[(6-methylpyridin-2-yl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound CC1=CC=CC(CC2=NN3C(=N2)C(C2=CC=NC=N2)=C(N=C3N)C2=CC=CC(=C2)C#N)=N1 ZCKITDLHOGMUTN-UHFFFAOYSA-N 0.000 claims 1
- DZCQMKYLRMQQQH-HXUWFJFHSA-N 3-[5-amino-2-[(R)-hydroxy(phenyl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)[C@@H](C1=CC=CC=C1)O)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 DZCQMKYLRMQQQH-HXUWFJFHSA-N 0.000 claims 1
- DZCQMKYLRMQQQH-FQEVSTJZSA-N 3-[5-amino-2-[(S)-hydroxy(phenyl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)[C@H](C1=CC=CC=C1)O)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 DZCQMKYLRMQQQH-FQEVSTJZSA-N 0.000 claims 1
- UMUFXMZUESIYBU-UHFFFAOYSA-N 3-[5-amino-2-[[2-(1-methylpyrazol-4-yl)phenyl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1)C=1C=NN(C=1)C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 UMUFXMZUESIYBU-UHFFFAOYSA-N 0.000 claims 1
- FHKNVNFPMRQSCZ-UHFFFAOYSA-N 3-[5-amino-2-[[2-[(1,1-dioxo-1,2-thiazolidin-2-yl)methyl]-6-fluorophenyl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)CN1S(CCC1)(=O)=O)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 FHKNVNFPMRQSCZ-UHFFFAOYSA-N 0.000 claims 1
- UKHMVYJJWMEXNW-UHFFFAOYSA-N 3-[5-amino-2-[[2-[(2,5-dioxoimidazolidin-1-yl)methyl]-6-fluorophenyl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)CN1C(NCC1=O)=O)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 UKHMVYJJWMEXNW-UHFFFAOYSA-N 0.000 claims 1
- KCMHPIYXDPAKBC-UHFFFAOYSA-N 3-[5-amino-2-[[2-fluoro-6-[(3-methyl-2,5-dioxoimidazolidin-1-yl)methyl]phenyl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1CN1C(N(CC1=O)C)=O)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 KCMHPIYXDPAKBC-UHFFFAOYSA-N 0.000 claims 1
- CUNFOADGMKYQNJ-FYYLOGMGSA-N 3-[5-amino-2-[[2-fluoro-6-[[(3R,4R)-3-fluoro-4-hydroxypyrrolidin-1-yl]methyl]phenyl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1CN1C[C@H]([C@@H](C1)O)F)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 CUNFOADGMKYQNJ-FYYLOGMGSA-N 0.000 claims 1
- XOHBNQCHUBIJNG-UHFFFAOYSA-N 3-[5-amino-2-[[3-(hydroxymethyl)pyridin-2-yl]methyl]-8-(4-methyl-1,3-oxazol-5-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1CO)C1=C(N=CO1)C)C=1C=C(C#N)C=CC=1 XOHBNQCHUBIJNG-UHFFFAOYSA-N 0.000 claims 1
- RONNEODEIRRODO-UHFFFAOYSA-N 3-[5-amino-2-[[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CN1N=C(C=C1C)C(F)(F)F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 RONNEODEIRRODO-UHFFFAOYSA-N 0.000 claims 1
- VYMAQPYIBOACPX-UHFFFAOYSA-N 3-[5-amino-2-[[cyano(phenyl)methyl]amino]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(NC(C#N)C3=CC=CC=C3)=NN12)C1=CC=NC=N1 VYMAQPYIBOACPX-UHFFFAOYSA-N 0.000 claims 1
- HLXMJCAEUZXPPO-UHFFFAOYSA-N 3-[5-amino-2-[phenyl(pyridin-2-yloxy)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)C(OC1=NC=CC=C1)C1=CC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 HLXMJCAEUZXPPO-UHFFFAOYSA-N 0.000 claims 1
- QCKBCYINTBGLPS-UHFFFAOYSA-N 3-[5-amino-8-(2-ethylpyrazol-3-yl)-2-(1-phenylcyclopropyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound CCN1N=CC=C1C1=C(N=C(N)N2N=C(N=C12)C1(CC1)C1=CC=CC=C1)C1=CC=CC(=C1)C#N QCKBCYINTBGLPS-UHFFFAOYSA-N 0.000 claims 1
- XUXCHAYNSGXUMM-UHFFFAOYSA-N 3-[5-amino-8-(2-ethylpyrazol-3-yl)-2-(pyridin-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 XUXCHAYNSGXUMM-UHFFFAOYSA-N 0.000 claims 1
- ZHKNDNJHSIMBEH-UHFFFAOYSA-N 3-[5-amino-8-(2-ethylpyrazol-3-yl)-2-[(1-methylindazol-3-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NN(C2=CC=CC=C12)C)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 ZHKNDNJHSIMBEH-UHFFFAOYSA-N 0.000 claims 1
- ZMJYOEKAEHHXKD-UHFFFAOYSA-N 3-[5-amino-8-(2-ethylpyrazol-3-yl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 ZMJYOEKAEHHXKD-UHFFFAOYSA-N 0.000 claims 1
- UWZRABCLSLBABK-UHFFFAOYSA-N 3-[5-amino-8-(2-ethylpyrazol-3-yl)-2-[(3-methoxypyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC)C1=CC=NN1CC)C=1C=C(C#N)C=CC=1 UWZRABCLSLBABK-UHFFFAOYSA-N 0.000 claims 1
- KOTRBKQRHIWPEW-UHFFFAOYSA-N 3-[5-amino-8-(2-methoxy-6-methylpyridin-4-yl)-2-(pyridin-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound COC1=NC(C)=CC(=C1)C1=C(N=C(N)N2N=C(CC3=NC=CC=C3)N=C12)C1=CC=CC(=C1)C#N KOTRBKQRHIWPEW-UHFFFAOYSA-N 0.000 claims 1
- FUKSKVKMUXZADL-UHFFFAOYSA-N 3-[5-amino-8-(2-propylpyrazol-3-yl)-2-(pyridin-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=CC=NN1CCC)C=1C=C(C#N)C=CC=1 FUKSKVKMUXZADL-UHFFFAOYSA-N 0.000 claims 1
- RCHBTIFFQLLZFC-UHFFFAOYSA-N 3-[5-amino-8-(3-ethyltriazol-4-yl)-2-(pyridin-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=CN=NN1CC)C=1C=C(C#N)C=CC=1 RCHBTIFFQLLZFC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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| JP2022545923A (ja) * | 2019-08-26 | 2022-11-01 | インサイト・コーポレイション | Ａ２ａ／ａ２ｂ阻害剤としてのトリアゾロピリミジン |
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