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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