JPWO2020052631A5 - - Google Patents
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- Publication number
- JPWO2020052631A5 JPWO2020052631A5 JP2021513827A JP2021513827A JPWO2020052631A5 JP WO2020052631 A5 JPWO2020052631 A5 JP WO2020052631A5 JP 2021513827 A JP2021513827 A JP 2021513827A JP 2021513827 A JP2021513827 A JP 2021513827A JP WO2020052631 A5 JPWO2020052631 A5 JP WO2020052631A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- methyl
- amino
- alkyl
- pyrimidin
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 85
- 229920006395 saturated elastomer Polymers 0.000 claims 43
- -1 cyano, hydroxyl Chemical group 0.000 claims 36
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000004452 carbocyclyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical group 0.000 claims 19
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 18
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims 15
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 12
- 239000004202 carbamide Substances 0.000 claims 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- IDPLEAPGHSRRKF-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 IDPLEAPGHSRRKF-UHFFFAOYSA-N 0.000 claims 4
- 102000009346 Adenosine receptors Human genes 0.000 claims 4
- 108050000203 Adenosine receptors Proteins 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229940127089 cytotoxic agent Drugs 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- MFOVNQPXJSGJPL-UHFFFAOYSA-N 7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylbenzimidazol-5-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=CC=C(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC1=NC=CC=C1F)C=1C=CC2=C(N(C=N2)C)C=1 MFOVNQPXJSGJPL-UHFFFAOYSA-N 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 3
- 239000002955 immunomodulating agent Substances 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- FGERZKWETDOAOC-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(2-methylmorpholin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N1CC(OCC1)C)N FGERZKWETDOAOC-UHFFFAOYSA-N 0.000 claims 2
- BINPGHNNTJJWJW-UHFFFAOYSA-N 7-(4-fluorophenyl)-8-(2-methylpyridin-4-yl)-2-(1,3-thiazol-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=CC=C(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC=1SC=CN=1)C1=CC(=NC=C1)C BINPGHNNTJJWJW-UHFFFAOYSA-N 0.000 claims 2
- YEJJJXQNIXCTJY-UHFFFAOYSA-N 7-(4-fluorophenyl)-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-2-(oxolan-3-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=CC=C(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC1COCC1)C=1C=CC=2N(C=1)C(=CN=2)C YEJJJXQNIXCTJY-UHFFFAOYSA-N 0.000 claims 2
- YXMOEFODDQFQNL-UHFFFAOYSA-N 8-(2,6-dimethylpyridin-4-yl)-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound CC1=NC(=CC(=C1)C=1C=2N(C(=NC=1C1=CC=C(C=C1)F)N)N=C(N=2)CC1=NC=CC=C1F)C YXMOEFODDQFQNL-UHFFFAOYSA-N 0.000 claims 2
- HXUYNIIAUKDHMW-UHFFFAOYSA-N 8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(1,3-oxazol-2-yl)-2-(oxolan-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound CC1=CN=C2N1C=C(C=C2)C=1C=2N(C(=NC=1C=1OC=CN=1)N)N=C(N=2)CC1OCCC1 HXUYNIIAUKDHMW-UHFFFAOYSA-N 0.000 claims 2
- ZKNCPHDOHBCAIF-UHFFFAOYSA-N 8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(1,3-oxazol-2-yl)-2-(oxolan-3-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound CC1=CN=C2N1C=C(C=C2)C=1C=2N(C(=NC=1C=1OC=CN=1)N)N=C(N=2)CC1COCC1 ZKNCPHDOHBCAIF-UHFFFAOYSA-N 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- 208000011623 Obstructive Lung disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 229960005305 adenosine Drugs 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000005494 pyridonyl group Chemical group 0.000 claims 2
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- 208000019465 refractory cytopenia of childhood Diseases 0.000 claims 2
- 208000002491 severe combined immunodeficiency Diseases 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- KJEPUKDZBLUKNF-UHFFFAOYSA-N 2-(2-methoxyethyl)-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical class COCCC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C=1OC=CN=1)N KJEPUKDZBLUKNF-UHFFFAOYSA-N 0.000 claims 1
- RPNNVPNPQYTQTJ-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-7-(3-methoxyazetidin-1-yl)-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C=2C=CC=3N(C=2)C(=CN=3)C)N2CC(C2)OC)N)C(=CC=C1)F RPNNVPNPQYTQTJ-UHFFFAOYSA-N 0.000 claims 1
- JUJONFDGLHEEMD-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-7-(4-fluorophenyl)-8-(2-methoxypyridin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C2=CC(=NC=C2)OC)C2=CC=C(C=C2)F)N)C(=CC=C1)F JUJONFDGLHEEMD-UHFFFAOYSA-N 0.000 claims 1
- OWWRGDZFTAVINL-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-7-(4-fluorophenyl)-8-[2-(trifluoromethyl)pyridin-4-yl]-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(C(=CC=C1)F)CC1=NN2C(=NC(=C(C2=N1)C1=CC(=NC=C1)C(F)(F)F)C1=CC=C(C=C1)F)N OWWRGDZFTAVINL-UHFFFAOYSA-N 0.000 claims 1
- XAAGIWOKJGFAQZ-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-7-(4-fluorophenyl)-8-pyridazin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C2=CN=NC=C2)C2=CC=C(C=C2)F)N)C(=CC=C1)F XAAGIWOKJGFAQZ-UHFFFAOYSA-N 0.000 claims 1
- IQQHTQIEBYJKIK-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(2,3-dimethylpyridin-4-yl)-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C2=C(C(=NC=C2)C)C)C2=CC=C(C=C2)F)N)C(=CC=C1)F IQQHTQIEBYJKIK-UHFFFAOYSA-N 0.000 claims 1
- NXJBJLTZXKFWSZ-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(2,5-dimethylpyridin-4-yl)-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(C(=CC=C1)F)CC1=NN2C(=NC(=C(C2=N1)C1=CC(=NC=C1C)C)C1=CC=C(C=C1)F)N NXJBJLTZXKFWSZ-UHFFFAOYSA-N 0.000 claims 1
- SPQSEZHCCXDHFX-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(2,6-dimethylpyridin-4-yl)-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(C(=CC=C1)F)CC1=NN2C(=NC(=C(C2=N1)C1=CC(=NC(=C1)C)C)C=1OC=CN=1)N SPQSEZHCCXDHFX-UHFFFAOYSA-N 0.000 claims 1
- AMRZGYQWVDQOFS-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(2,6-dimethylpyridin-4-yl)-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C2=CC(=NC(=C2)C)C)C2=CC=C(C=C2)F)N)C(=CC=C1)F AMRZGYQWVDQOFS-UHFFFAOYSA-N 0.000 claims 1
- UABYOPZHIAEXOX-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(3-methylbenzimidazol-5-yl)-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C=2C=CC3=C(N(C=N3)C)C=2)C=2OC=CN=2)N)C(=CC=C1)F UABYOPZHIAEXOX-UHFFFAOYSA-N 0.000 claims 1
- QGBOMSOQOOQQJI-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C=2C=CC=3N(C=2)C(=CN=3)C)N2CCN(CC2)C)N)C(=CC=C1)F QGBOMSOQOOQQJI-UHFFFAOYSA-N 0.000 claims 1
- QOCNPKMKLAIZQX-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-morpholin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C=2C=CC=3N(C=2)C(=CN=3)C)N2CCOCC2)N)C(=CC=C1)F QOCNPKMKLAIZQX-UHFFFAOYSA-N 0.000 claims 1
- SYFZVDQFZLHXTD-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C=2C=CC=3N(C=2)C(=CN=3)C)N2CCCC2)N)C(=CC=C1)F SYFZVDQFZLHXTD-UHFFFAOYSA-N 0.000 claims 1
- PFAXMIALVXBXEB-UHFFFAOYSA-N 2-[(2,6-difluorophenyl)methyl]-8-[2-(dimethylamino)pyridin-4-yl]-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(CC2=NN3C(=NC(=C(C3=N2)C2=CC(=NC=C2)N(C)C)C2=CC=C(C=C2)F)N)C(=CC=C1)F PFAXMIALVXBXEB-UHFFFAOYSA-N 0.000 claims 1
- FEWMEHGDBSYSEN-UHFFFAOYSA-N 2-[(3-chlorophenyl)methyl]-7-(4-fluorophenyl)-8-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound ClC=1C=C(C=CC=1)CC1=NN2C(=NC(=C(C2=N1)C1=CC(=NC=C1)C)C1=CC=C(C=C1)F)N FEWMEHGDBSYSEN-UHFFFAOYSA-N 0.000 claims 1
- OOAGAXDDBFJMBM-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-7-N,7-N-dimethyl-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-[1,2,4]triazolo[1,5-c]pyrimidine-5,7-diamine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N(C)C)N OOAGAXDDBFJMBM-UHFFFAOYSA-N 0.000 claims 1
- JCJYAMJSBBLNPG-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylbenzimidazol-5-yl)-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC2=C(N(C=N2)C)C=1)C=1OC=CN=1)N JCJYAMJSBBLNPG-UHFFFAOYSA-N 0.000 claims 1
- JQAJTSUCPJHEDV-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C=1OC=CN=1)N JQAJTSUCPJHEDV-UHFFFAOYSA-N 0.000 claims 1
- KLNPLIKINOXCQC-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(2-oxa-7-azaspiro[3.4]octan-7-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N1CC2(COC2)CC1)N KLNPLIKINOXCQC-UHFFFAOYSA-N 0.000 claims 1
- NRNSBKUJVRRFFX-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-(3-methylmorpholin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N1C(COCC1)C)N NRNSBKUJVRRFFX-UHFFFAOYSA-N 0.000 claims 1
- NRNSBKUJVRRFFX-OAHLLOKOSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-[(3R)-3-methylmorpholin-4-yl]-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound C[C@@H]1COCCN1C1=C(C2=NC(CC3=C(F)C=CC=N3)=NN2C(N)=N1)C1=CN2C(C)=CN=C2C=C1 NRNSBKUJVRRFFX-OAHLLOKOSA-N 0.000 claims 1
- GTHPJWYCEYRKPS-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-morpholin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N1CCOCC1)N GTHPJWYCEYRKPS-UHFFFAOYSA-N 0.000 claims 1
- KQRSRIOFGHZSRZ-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-7-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)N1CCCC1)N KQRSRIOFGHZSRZ-UHFFFAOYSA-N 0.000 claims 1
- PMRKZAQQXFIXNH-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-imidazo[1,2-a]pyridin-6-yl-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C=CN=2)C=1OC=CN=1)N PMRKZAQQXFIXNH-UHFFFAOYSA-N 0.000 claims 1
- WOCPGZPOHBUZHI-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-imidazo[1,2-a]pyridin-6-yl-7-(triazol-1-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C=CN=2)N1N=NC=C1)N WOCPGZPOHBUZHI-UHFFFAOYSA-N 0.000 claims 1
- ZXQUGYFCFUBOSW-UHFFFAOYSA-N 2-[(3-fluoropyridin-2-yl)methyl]-8-imidazo[1,2-a]pyridin-6-yl-7-(triazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC=1C(=NC=CC=1)CC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C=CN=2)N1N=CC=N1)N ZXQUGYFCFUBOSW-UHFFFAOYSA-N 0.000 claims 1
- OGILCXDJHLQZTN-UHFFFAOYSA-N 2-[(6-aminopyridin-2-yl)methyl]-7-(4-fluorophenyl)-8-imidazo[1,2-a]pyridin-6-yl-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=CC=CC(=N1)N)C=1C=CC=2N(C=1)C=CN=2)C1=CC=C(C=C1)F OGILCXDJHLQZTN-UHFFFAOYSA-N 0.000 claims 1
- DSBOCGKTYCTNOO-UHFFFAOYSA-N 2-[(6-chloropyridin-2-yl)methyl]-7-(4-fluorophenyl)-8-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound ClC1=CC=CC(=N1)CC1=NN2C(=NC(=C(C2=N1)C1=CC(=NC=C1)C)C1=CC=C(C=C1)F)N DSBOCGKTYCTNOO-UHFFFAOYSA-N 0.000 claims 1
- WHKSSDHOAZGHRB-UHFFFAOYSA-N 2-[1-(2,6-difluorophenyl)ethyl]-7-(4-fluorophenyl)-8-(2-methylpyridin-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=C(C(=CC=C1)F)C(C)C1=NN2C(=NC(=C(C2=N1)C1=CC(=NC=C1)C)C1=CC=C(C=C1)F)N WHKSSDHOAZGHRB-UHFFFAOYSA-N 0.000 claims 1
- RJODVEWAMLKSIX-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-7-(4-fluorophenyl)-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound CN(CCC1=NN2C(=NC(=C(C2=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C1=CC=C(C=C1)F)N)C RJODVEWAMLKSIX-UHFFFAOYSA-N 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- XOHOLZCXFDPBFD-UHFFFAOYSA-N 3-amino-N-[[2-(difluoromethoxy)phenyl]methyl]-5-(4-fluorophenyl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1)OC(F)F XOHOLZCXFDPBFD-UHFFFAOYSA-N 0.000 claims 1
- LWYDAAASGGAOQH-UHFFFAOYSA-N 4-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-6-methylpyridine-2-carbonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C1=CC(=NC(=C1)C)C#N)C=1OC=CN=1 LWYDAAASGGAOQH-UHFFFAOYSA-N 0.000 claims 1
- UFJDURNDZGLRES-UHFFFAOYSA-N 4-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-8-(1-methyl-6-oxopyridin-3-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=CN(C(C=C1)=O)C)C1=CC=C(C#N)C=C1 UFJDURNDZGLRES-UHFFFAOYSA-N 0.000 claims 1
- NIGKXRTZEVGHAE-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-propan-2-ylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C(C)C)=O)C=1OC=CN=1 NIGKXRTZEVGHAE-UHFFFAOYSA-N 0.000 claims 1
- VLEJDOHBWVIJDB-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(1,3-thiazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1SC=CN=1 VLEJDOHBWVIJDB-UHFFFAOYSA-N 0.000 claims 1
- KVTHXAIJSHWNRJ-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F KVTHXAIJSHWNRJ-UHFFFAOYSA-N 0.000 claims 1
- FRARONYZNDGNDS-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(4-methyl-1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1OC=C(N=1)C FRARONYZNDGNDS-UHFFFAOYSA-N 0.000 claims 1
- JCQFWDWHRGLROT-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(5-methyl-1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1OC(=CN=1)C JCQFWDWHRGLROT-UHFFFAOYSA-N 0.000 claims 1
- FYGUOAMXRGGXGR-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(6-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1C=NC(=CC=1)C FYGUOAMXRGGXGR-UHFFFAOYSA-N 0.000 claims 1
- NOYVLVDEKLNKFK-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-(triazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)N1N=CC=N1 NOYVLVDEKLNKFK-UHFFFAOYSA-N 0.000 claims 1
- BJCXOFQLGPZNJF-UHFFFAOYSA-N 5-[5-amino-2-[(2,6-difluorophenyl)methyl]-7-pyridin-2-yl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C1=NC=CC=C1 BJCXOFQLGPZNJF-UHFFFAOYSA-N 0.000 claims 1
- ANVNFQJDCKBOSL-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 ANVNFQJDCKBOSL-UHFFFAOYSA-N 0.000 claims 1
- PBEPDXNNUJNEBV-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-propan-2-ylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C(C)C)=O)C=1OC=CN=1 PBEPDXNNUJNEBV-UHFFFAOYSA-N 0.000 claims 1
- GSTPWHKSOLFYKX-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(1-methylindol-5-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C=1C=C2C=CN(C2=CC=1)C GSTPWHKSOLFYKX-UHFFFAOYSA-N 0.000 claims 1
- SASATIXQULDOOF-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C=1C=NN(C=1)C SASATIXQULDOOF-UHFFFAOYSA-N 0.000 claims 1
- GBQZESSPWOQRTG-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(2-methoxyphenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=C(C=CC=C1)OC GBQZESSPWOQRTG-UHFFFAOYSA-N 0.000 claims 1
- HIGKOUOMTIZHNQ-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(3-methoxyphenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=CC=C1)OC HIGKOUOMTIZHNQ-UHFFFAOYSA-N 0.000 claims 1
- PHWLGGRFNGIWGN-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)OC PHWLGGRFNGIWGN-UHFFFAOYSA-N 0.000 claims 1
- RZNADYWAPSONEM-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)C(F)(F)F RZNADYWAPSONEM-UHFFFAOYSA-N 0.000 claims 1
- WWGWJTQBATTYLS-UHFFFAOYSA-N 5-[5-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyrazol-1-yl-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)N1N=CC=C1 WWGWJTQBATTYLS-UHFFFAOYSA-N 0.000 claims 1
- DRWXKQJJYFKKOA-UHFFFAOYSA-N 5-[5-amino-2-[(6-aminopyridin-2-yl)methyl]-7-(4-fluorophenyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC(=CC=C1)N)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F DRWXKQJJYFKKOA-UHFFFAOYSA-N 0.000 claims 1
- HNQYRYXKHXZOGM-UHFFFAOYSA-N 5-[5-amino-2-[[3-(difluoromethoxy)pyridin-2-yl]methyl]-7-(1,3-oxazol-2-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC(F)F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 HNQYRYXKHXZOGM-UHFFFAOYSA-N 0.000 claims 1
- YRZPSLADKZXWDF-UHFFFAOYSA-N 5-[5-amino-7-(2,4-difluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=C(C=C(C=C1)F)F YRZPSLADKZXWDF-UHFFFAOYSA-N 0.000 claims 1
- DBUPUCKVPMUXEX-UHFFFAOYSA-N 5-[5-amino-7-(2-chlorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=C(C=CC=C1)Cl DBUPUCKVPMUXEX-UHFFFAOYSA-N 0.000 claims 1
- CUZJHUAIWPKQIM-UHFFFAOYSA-N 5-[5-amino-7-(3,4-difluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=C(C=C1)F)F CUZJHUAIWPKQIM-UHFFFAOYSA-N 0.000 claims 1
- BDMJIWAVRLIUOP-UHFFFAOYSA-N 5-[5-amino-7-(3,5-difluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=CC(=C1)F)F BDMJIWAVRLIUOP-UHFFFAOYSA-N 0.000 claims 1
- FYYYTBJDBREAOI-UHFFFAOYSA-N 5-[5-amino-7-(3-chlorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=CC=C1)Cl FYYYTBJDBREAOI-UHFFFAOYSA-N 0.000 claims 1
- GWYRYXJKVPHICH-UHFFFAOYSA-N 5-[5-amino-7-(3-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=CC=C1)F GWYRYXJKVPHICH-UHFFFAOYSA-N 0.000 claims 1
- FKPGIFAGBDNMQP-UHFFFAOYSA-N 5-[5-amino-7-(4-chlorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)Cl FKPGIFAGBDNMQP-UHFFFAOYSA-N 0.000 claims 1
- DFXFMJLXQWVGCL-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-(1,3-thiazol-2-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC=1SC=CN=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F DFXFMJLXQWVGCL-UHFFFAOYSA-N 0.000 claims 1
- FAFWPWMKYLQUHT-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-(1,3-thiazol-4-ylmethyl)-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC=1N=CSC=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F FAFWPWMKYLQUHT-UHFFFAOYSA-N 0.000 claims 1
- WNXQQSLXEOLCRS-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1,3-dimethylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=C(C(N(C=1)C)=O)C)C1=CC=C(C=C1)F WNXQQSLXEOLCRS-UHFFFAOYSA-N 0.000 claims 1
- MJGBQQVCOJFOSA-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-(2-hydroxyethyl)pyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)CCO)=O)C1=CC=C(C=C1)F MJGBQQVCOJFOSA-UHFFFAOYSA-N 0.000 claims 1
- MGVORKOWNJZJCZ-SFHVURJKSA-N 5-[5-amino-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-[(3S)-oxolan-3-yl]pyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)[C@@H]1COCC1)=O)C1=CC=C(C=C1)F MGVORKOWNJZJCZ-SFHVURJKSA-N 0.000 claims 1
- BFFFIJSOBYMNPI-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-ethylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)CC)=O)C1=CC=C(C=C1)F BFFFIJSOBYMNPI-UHFFFAOYSA-N 0.000 claims 1
- YIDWZRRYJRXRPX-UHFFFAOYSA-N 5-[5-amino-7-(4-fluorophenyl)-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-propan-2-ylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C(C)C)=O)C1=CC=C(C=C1)F YIDWZRRYJRXRPX-UHFFFAOYSA-N 0.000 claims 1
- LVPAJTBABSCKNK-UHFFFAOYSA-N 5-[5-amino-7-[4-(difluoromethyl)phenyl]-2-[(3-fluoropyridin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)C(F)F LVPAJTBABSCKNK-UHFFFAOYSA-N 0.000 claims 1
- XGANDSJRULUAJD-UHFFFAOYSA-N 5-[5-amino-7-chloro-2-[(2,6-difluorophenyl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-8-yl]-1-methylpyridin-2-one Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)Cl XGANDSJRULUAJD-UHFFFAOYSA-N 0.000 claims 1
- ARIKWXSYFKNBJV-UHFFFAOYSA-N 7-(3-fluoropyrazol-1-yl)-2-[(3-fluoropyridin-2-yl)methyl]-8-(3-methylimidazo[1,2-a]pyridin-6-yl)-[1,2,4]triazolo[1,5-c]pyrimidin-5-amine Chemical compound FC1=NN(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC1=NC=CC=C1F)C=1C=CC=2N(C=1)C(=CN=2)C ARIKWXSYFKNBJV-UHFFFAOYSA-N 0.000 claims 1
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| US11066410B2 (en) * | 2017-03-24 | 2021-07-20 | 3100 Central Expressway Llc | Fused triazolo-pyrimidine compounds having useful pharmaceutical application |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| BR122023024273A2 (pt) | 2018-02-27 | 2024-02-20 | Incyte Corporation | Compostos imidazopirimidinas e triazolopirimidinas, seus usos, método para inibir uma atividade de um receptor de adenosina e composição farmacêutica dos mesmos |
| US11220510B2 (en) | 2018-04-09 | 2022-01-11 | Incyte Corporation | Pyrrole tricyclic compounds as A2A / A2B inhibitors |
| WO2019222677A1 (en) | 2018-05-18 | 2019-11-21 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| GEP20237548B (en) | 2018-07-05 | 2023-10-10 | Incyte Corp | Fused pyrazine derivatives as a2a /a2b inhibitors |
| AR116315A1 (es) * | 2018-09-12 | 2021-04-21 | Dizal Jiangsu Pharmaceutical Co Ltd | Compuestos de triazolo-pirimidina y usos de los mismos |
| EP3911324A4 (en) | 2019-01-18 | 2022-08-17 | Nuvation Bio Inc. | 1,8-NAPHTHYRIDINONE COMPOUNDS AND THEIR USES |
| EP3911323A4 (en) | 2019-01-18 | 2022-11-16 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| US20210061809A1 (en) * | 2019-08-26 | 2021-03-04 | Incyte Corporation | Triazolopyrimidines as a2a / a2b inhibitors |
| WO2021156439A1 (en) | 2020-02-06 | 2021-08-12 | Astrazeneca Ab | Triazole compounds as adenosine receptor antagonists |
| CN120022278A (zh) * | 2023-11-22 | 2025-05-23 | 英诺湖医药(杭州)有限公司 | 用于治疗癌症的化合物 |
| CN117865963B (zh) * | 2023-12-15 | 2026-02-24 | 上海凌凯科技股份有限公司 | 一种嘧啶酮衍生物的合成方法及嘧啶酮衍生物 |
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| JP4195729B2 (ja) * | 1997-03-24 | 2008-12-10 | 協和醗酵工業株式会社 | ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| JPWO2002079204A1 (ja) | 2001-03-28 | 2004-07-22 | 協和醗酵工業株式会社 | ８−チアゾリル［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 |
| PE20030739A1 (es) | 2001-11-30 | 2003-08-28 | Schering Corp | Antagonistas del receptor de adenosina a2a |
| EP1544200A1 (en) | 2002-09-24 | 2005-06-22 | Kyowa Hakko Kogyo Co., Ltd. | 1,2,4 -TRIAZOLO 1,5-c PYRIMIDINE DERIVATIVE |
| CN110214012B (zh) * | 2017-01-20 | 2023-05-09 | 艾库斯生物科学有限公司 | 用于治疗癌症相关疾病的唑嘧啶 |
| CN109963854B (zh) * | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| PL3611174T3 (pl) * | 2017-04-07 | 2022-08-08 | Medshine Discovery Inc. | Pochodne [1,2,4]triazolo[1,5-c]pirymidyny jako inhibitor receptora a2a |
| CN109535161B (zh) * | 2017-09-22 | 2021-09-03 | 江苏恒瑞医药股份有限公司 | 三唑并嘧啶类衍生物、其制备方法及其在医药上的应用 |
| BR122023024273A2 (pt) * | 2018-02-27 | 2024-02-20 | Incyte Corporation | Compostos imidazopirimidinas e triazolopirimidinas, seus usos, método para inibir uma atividade de um receptor de adenosina e composição farmacêutica dos mesmos |
| CN112105617B (zh) * | 2018-04-28 | 2022-04-05 | 南京明德新药研发有限公司 | 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法 |
| AR116315A1 (es) * | 2018-09-12 | 2021-04-21 | Dizal Jiangsu Pharmaceutical Co Ltd | Compuestos de triazolo-pirimidina y usos de los mismos |
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