JP2017533946A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017533946A5 JP2017533946A5 JP2017526527A JP2017526527A JP2017533946A5 JP 2017533946 A5 JP2017533946 A5 JP 2017533946A5 JP 2017526527 A JP2017526527 A JP 2017526527A JP 2017526527 A JP2017526527 A JP 2017526527A JP 2017533946 A5 JP2017533946 A5 JP 2017533946A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- carboxamide
- pyrazine
- oxazol
- 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
Links
- -1 (i) -F Chemical class 0.000 claims 185
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 69
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 150000003857 carboxamides Chemical class 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims 7
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- WBTNLVCNTIPZIJ-UHFFFAOYSA-N 3-amino-N-(4-hydroxycycloheptyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCC(CCC1)O WBTNLVCNTIPZIJ-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 3
- KAMYCIWSTFTVBT-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1C KAMYCIWSTFTVBT-UHFFFAOYSA-N 0.000 claims 3
- UQRHAFHCIMJVSW-UHFFFAOYSA-N 3-amino-6-methyl-N-[1-(3-methylpyridin-2-yl)ethyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC(C)C1=NC=CC=C1C UQRHAFHCIMJVSW-UHFFFAOYSA-N 0.000 claims 3
- RJZDYGSTHCVQNH-UHFFFAOYSA-N 3-amino-N-(6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCC=2C1=NC=CC=2 RJZDYGSTHCVQNH-UHFFFAOYSA-N 0.000 claims 3
- ZTFCDOSGCABCHO-UHFFFAOYSA-N 3-amino-N-[(3-cyclopropylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1C1CC1 ZTFCDOSGCABCHO-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 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
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- HNROJDQOHFHZAD-UHFFFAOYSA-N 3-amino-6-cyano-5-(1,3-oxazol-2-yl)-N-[[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C#N)C(=O)NCC1=NC=CC=C1C(F)(F)F HNROJDQOHFHZAD-UHFFFAOYSA-N 0.000 claims 2
- WQOISRYDKPBTQX-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1,2,3,4-tetrahydronaphthalen-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CC2=CC=CC=C2CC1 WQOISRYDKPBTQX-UHFFFAOYSA-N 0.000 claims 2
- GWIZHDZCHUSZAY-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1-pyridin-2-ylethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC(C)C1=NC=CC=C1 GWIZHDZCHUSZAY-UHFFFAOYSA-N 0.000 claims 2
- QLFFAJPHHFKFDS-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1-pyridin-2-ylpropyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC(CC)C1=NC=CC=C1 QLFFAJPHHFKFDS-UHFFFAOYSA-N 0.000 claims 2
- ZBOUWLHPUGQFGC-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(2-pyridin-2-ylethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCCC1=NC=CC=C1 ZBOUWLHPUGQFGC-UHFFFAOYSA-N 0.000 claims 2
- VLQOTMYHJQRFCB-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(5,6,7,8-tetrahydroisoquinolin-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1C=2C=CN=CC=2CCC1 VLQOTMYHJQRFCB-UHFFFAOYSA-N 0.000 claims 2
- ISVZJEKBYKQANO-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(5,6,7,8-tetrahydroquinolin-8-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCCC=2C=CC=NC1=2 ISVZJEKBYKQANO-UHFFFAOYSA-N 0.000 claims 2
- AXOLHIFOJBDPID-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyrimidin-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=N1 AXOLHIFOJBDPID-UHFFFAOYSA-N 0.000 claims 2
- AAKGUOGJEIAQDA-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1C(F)(F)F AAKGUOGJEIAQDA-UHFFFAOYSA-N 0.000 claims 2
- SHUAGHJFZLIRHB-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-5-yl)-N-[[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)C)C(=O)NCC1=NC=CC=C1C(F)(F)F SHUAGHJFZLIRHB-UHFFFAOYSA-N 0.000 claims 2
- JWQPUADFVQREPH-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyrazin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CN=C1C JWQPUADFVQREPH-UHFFFAOYSA-N 0.000 claims 2
- XQWOKSAMTGTJRH-UHFFFAOYSA-N 3-amino-6-methyl-N-[(4-methylpyridazin-3-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1N=NC=CC=1C XQWOKSAMTGTJRH-UHFFFAOYSA-N 0.000 claims 2
- PLPRGZBIRBJVRV-UHFFFAOYSA-N 3-amino-N-(2,2-difluorocyclopentyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1C(CCC1)(F)F PLPRGZBIRBJVRV-UHFFFAOYSA-N 0.000 claims 2
- AIJLVIBQYGFYDU-UHFFFAOYSA-N 3-amino-N-(5-methoxy-2,3-dihydro-1H-inden-1-yl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCC2=CC(=CC=C12)OC AIJLVIBQYGFYDU-UHFFFAOYSA-N 0.000 claims 2
- PUHWJCWFHHCGHJ-UHFFFAOYSA-N 3-amino-N-(6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)-6-methyl-5-(1,3-oxazol-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)C)C(=O)NC1CCC=2C1=NC=CC=2 PUHWJCWFHHCGHJ-UHFFFAOYSA-N 0.000 claims 2
- MVJJDZBWSKXGSW-UHFFFAOYSA-N 3-amino-N-(isoquinolin-8-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=CC=C2C=CN=CC=12 MVJJDZBWSKXGSW-UHFFFAOYSA-N 0.000 claims 2
- NPVDVGVISLPKHI-UHFFFAOYSA-N 3-amino-N-[(3-cyclopropyl-4-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1C1CC1)F NPVDVGVISLPKHI-UHFFFAOYSA-N 0.000 claims 2
- DUASCGLOVSYNRG-UHFFFAOYSA-N 3-amino-N-[(3-cyclopropylpyrazin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CN=C1C1CC1 DUASCGLOVSYNRG-UHFFFAOYSA-N 0.000 claims 2
- OIQDXGUEQNZICX-UHFFFAOYSA-N 3-amino-N-[(3-ethyl-4-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1CC)F OIQDXGUEQNZICX-UHFFFAOYSA-N 0.000 claims 2
- LCZRUVCQJSGCEY-UHFFFAOYSA-N 3-amino-N-[(3-ethylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1CC LCZRUVCQJSGCEY-UHFFFAOYSA-N 0.000 claims 2
- NNQRVVWFSOPCAL-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1F NNQRVVWFSOPCAL-UHFFFAOYSA-N 0.000 claims 2
- SDCMGDMTWUWCQO-UHFFFAOYSA-N 3-amino-N-[(3-methoxypyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1OC SDCMGDMTWUWCQO-UHFFFAOYSA-N 0.000 claims 2
- BIWZUDQWJOXPEP-UHFFFAOYSA-N 3-amino-N-[(6-methoxypyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1)OC BIWZUDQWJOXPEP-UHFFFAOYSA-N 0.000 claims 2
- IPGYPHBTMQOJBN-UHFFFAOYSA-N 3-amino-N-[[3-(fluoromethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1CF IPGYPHBTMQOJBN-UHFFFAOYSA-N 0.000 claims 2
- UOFRGGSNZIUDIL-UHFFFAOYSA-N 3-amino-N-[[3-(hydroxymethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1CO UOFRGGSNZIUDIL-UHFFFAOYSA-N 0.000 claims 2
- XMGTUTJAGVSALL-UHFFFAOYSA-N 3-amino-N-[[6-(dimethylamino)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1)N(C)C XMGTUTJAGVSALL-UHFFFAOYSA-N 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- NMMVYSVOVOXKEY-UHFFFAOYSA-N [3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-(3,4-dihydro-2H-quinolin-1-yl)methanone Chemical compound N1(CCCC2=CC=CC=C12)C(=O)C=1C(=NC(=C(N=1)C)C=1OC=CN=1)N NMMVYSVOVOXKEY-UHFFFAOYSA-N 0.000 claims 2
- OCKMLNCQOQMNIC-UHFFFAOYSA-N [3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-(5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl)methanone Chemical compound N1=CN=CC2=C1CN(C2)C(=O)C=1C(=NC(=C(N=1)C)C=1OC=CN=1)N OCKMLNCQOQMNIC-UHFFFAOYSA-N 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- NOVFIQMJNAJOEO-VXGBXAGGSA-N 1-[(5R,7R)-5-fluoro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]-6-methyl-5-(1,3-oxazol-2-yl)-2H-pyrazin-3-amine Chemical compound NC=1CN(C(=C(N=1)C=1OC=CN=1)C)[C@@H]1C[C@H](C=2C1=NC=CC=2)F NOVFIQMJNAJOEO-VXGBXAGGSA-N 0.000 claims 1
- NOVFIQMJNAJOEO-NEPJUHHUSA-N 1-[(5R,7S)-5-fluoro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]-6-methyl-5-(1,3-oxazol-2-yl)-2H-pyrazin-3-amine Chemical compound NC=1CN(C(=C(N=1)C=1OC=CN=1)C)[C@H]1C[C@H](C=2C1=NC=CC=2)F NOVFIQMJNAJOEO-NEPJUHHUSA-N 0.000 claims 1
- NOVFIQMJNAJOEO-NWDGAFQWSA-N 1-[(5S,7R)-5-fluoro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]-6-methyl-5-(1,3-oxazol-2-yl)-2H-pyrazin-3-amine Chemical compound NC=1CN(C(=C(N=1)C=1OC=CN=1)C)[C@@H]1C[C@@H](C=2C1=NC=CC=2)F NOVFIQMJNAJOEO-NWDGAFQWSA-N 0.000 claims 1
- NOVFIQMJNAJOEO-RYUDHWBXSA-N 1-[(5S,7S)-5-fluoro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]-6-methyl-5-(1,3-oxazol-2-yl)-2H-pyrazin-3-amine Chemical compound NC=1CN(C(=C(N=1)C=1OC=CN=1)C)[C@H]1C[C@@H](C=2C1=NC=CC=2)F NOVFIQMJNAJOEO-RYUDHWBXSA-N 0.000 claims 1
- VQVDEOPXFQFJQG-UHFFFAOYSA-N 1-[3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-3-(4,6-dimethylpyridin-2-yl)propan-1-one Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(CCC1=NC(=CC(=C1)C)C)=O VQVDEOPXFQFJQG-UHFFFAOYSA-N 0.000 claims 1
- 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 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
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- MPZMLHYMDUXBDO-UHFFFAOYSA-N 3-amino-5-(4,5-dimethyl-1,3-oxazol-2-yl)-6-methyl-N-[(3-methylpyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=C(N=1)C)C)C)C(=O)NCC1=NC=CC=C1C MPZMLHYMDUXBDO-UHFFFAOYSA-N 0.000 claims 1
- FNKPAOGWECYNMB-UHFFFAOYSA-N 3-amino-5-[4-(methoxymethyl)-1,3-oxazol-2-yl]-6-methyl-N-[(3-methylpyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=C(N=1)COC)C)C(=O)NCC1=NC=CC=C1C FNKPAOGWECYNMB-UHFFFAOYSA-N 0.000 claims 1
- QJPLSCLKZVKEGN-UHFFFAOYSA-N 3-amino-6-chloro-5-(1,3-oxazol-5-yl)-N-(quinolin-8-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)Cl)C(=O)NCC=1C=CC=C2C=CC=NC=12 QJPLSCLKZVKEGN-UHFFFAOYSA-N 0.000 claims 1
- FDQPHPKMUPYWNL-UHFFFAOYSA-N 3-amino-6-ethenyl-5-(4-methylpyrazol-1-yl)-N-(quinolin-8-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC(=C1)C)C=C)C(=O)NCC=1C=CC=C2C=CC=NC=12 FDQPHPKMUPYWNL-UHFFFAOYSA-N 0.000 claims 1
- TWIKLCXDAZEKHE-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1,3-oxazol-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1OC=CN=1 TWIKLCXDAZEKHE-UHFFFAOYSA-N 0.000 claims 1
- SAHJZJYOXFXKTP-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1,3-oxazol-5-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=CN=CO1 SAHJZJYOXFXKTP-UHFFFAOYSA-N 0.000 claims 1
- ZXJAULMHMZRMLU-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1,3-thiazol-5-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=CN=CS1 ZXJAULMHMZRMLU-UHFFFAOYSA-N 0.000 claims 1
- KNSFIUJRCIXUMY-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C2=C(NN=1)CCC2 KNSFIUJRCIXUMY-UHFFFAOYSA-N 0.000 claims 1
- HTGVDUNTXVRXSZ-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(1-pyrimidin-2-ylpiperidin-4-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCN(CC1)C1=NC=CC=N1 HTGVDUNTXVRXSZ-UHFFFAOYSA-N 0.000 claims 1
- RRMZIHIUYOLPEX-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=2NCCCC=2C=C1 RRMZIHIUYOLPEX-UHFFFAOYSA-N 0.000 claims 1
- GBXMAPUCEYSVDK-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyridin-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1 GBXMAPUCEYSVDK-UHFFFAOYSA-N 0.000 claims 1
- ZEMINRDIWNZSMC-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyridin-3-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=NC=CC=1 ZEMINRDIWNZSMC-UHFFFAOYSA-N 0.000 claims 1
- MKBXENBPOXYOKR-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyridin-4-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=CC=NC=C1 MKBXENBPOXYOKR-UHFFFAOYSA-N 0.000 claims 1
- CYUXKJWZQCCVBO-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyrimidin-4-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=NC=C1 CYUXKJWZQCCVBO-UHFFFAOYSA-N 0.000 claims 1
- DITICXZAIDSISU-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(pyrimidin-5-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=NC=NC=1 DITICXZAIDSISU-UHFFFAOYSA-N 0.000 claims 1
- LQDZBYLHVSTFHY-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(quinolin-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC2=CC=CC=C2C=C1 LQDZBYLHVSTFHY-UHFFFAOYSA-N 0.000 claims 1
- DHBITMPCVVAFOQ-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(quinolin-8-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=CC=C2C=CC=NC=12 DHBITMPCVVAFOQ-UHFFFAOYSA-N 0.000 claims 1
- MTWVVTDHCDZBGD-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-(thiophen-2-ylmethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1SC=CC=1 MTWVVTDHCDZBGD-UHFFFAOYSA-N 0.000 claims 1
- HXPXAMHSPQGGPP-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[1-(2,2,2-trifluoroethyl)piperidin-3-yl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CN(CCC1)CC(F)(F)F HXPXAMHSPQGGPP-UHFFFAOYSA-N 0.000 claims 1
- WEFUUVZHUNCQNU-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[3-(trifluoromethyl)pyrazin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CN=C1C(F)(F)F WEFUUVZHUNCQNU-UHFFFAOYSA-N 0.000 claims 1
- ZJPRCPRCIIEXSN-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[4-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1)C(F)(F)F ZJPRCPRCIIEXSN-UHFFFAOYSA-N 0.000 claims 1
- REFSTQYTXVSTQL-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[4-(trifluoromethyl)pyrimidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=N1)C(F)(F)F REFSTQYTXVSTQL-UHFFFAOYSA-N 0.000 claims 1
- WSCZLGNFNDPTLN-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[5-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1)C(F)(F)F WSCZLGNFNDPTLN-UHFFFAOYSA-N 0.000 claims 1
- GLXQQSHZCZWQFH-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[5-(trifluoromethyl)pyrimidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=N1)C(F)(F)F GLXQQSHZCZWQFH-UHFFFAOYSA-N 0.000 claims 1
- XXPZAQZRRLPCDP-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-[[6-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1)C(F)(F)F XXPZAQZRRLPCDP-UHFFFAOYSA-N 0.000 claims 1
- CCCDASRLBQDGOI-UHFFFAOYSA-N 3-amino-6-methyl-5-(1,3-oxazol-2-yl)-N-piperidin-3-ylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CNCCC1 CCCDASRLBQDGOI-UHFFFAOYSA-N 0.000 claims 1
- LVPHWXVXUUWWLL-UHFFFAOYSA-N 3-amino-6-methyl-5-(4-methyl-1,3-oxazol-2-yl)-N-[(3-methylpyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=C(N=1)C)C)C(=O)NCC1=NC=CC=C1C LVPHWXVXUUWWLL-UHFFFAOYSA-N 0.000 claims 1
- RBUQALSXFMNXMR-UHFFFAOYSA-N 3-amino-6-methyl-5-(5-methyl-1,3-oxazol-2-yl)-N-[(3-methylpyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=CN=1)C)C)C(=O)NCC1=NC=CC=C1C RBUQALSXFMNXMR-UHFFFAOYSA-N 0.000 claims 1
- DZJGMTGCMWEDLN-UHFFFAOYSA-N 3-amino-6-methyl-N-(2-methyl-2-pyridin-4-ylpropyl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC(C)(C1=CC=NC=C1)C DZJGMTGCMWEDLN-UHFFFAOYSA-N 0.000 claims 1
- XTMCHYNTDXHWQQ-UHFFFAOYSA-N 3-amino-6-methyl-N-[(2-methylimidazo[1,2-a]pyridin-3-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=C(N=C2N1C=CC=C2)C XTMCHYNTDXHWQQ-UHFFFAOYSA-N 0.000 claims 1
- BVSDXBVWFSNVJL-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyridin-2-yl)methyl]-5-(1,3-oxazol-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)C)C(=O)NCC1=NC=CC=C1C BVSDXBVWFSNVJL-UHFFFAOYSA-N 0.000 claims 1
- YREJOIHRPRLIRU-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyridin-2-yl)methyl]-5-[4-(trifluoromethyl)-1,3-oxazol-2-yl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=C(N=1)C(F)(F)F)C)C(=O)NCC1=NC=CC=C1C YREJOIHRPRLIRU-UHFFFAOYSA-N 0.000 claims 1
- WDNHWVDNEIQLRZ-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyridin-2-yl)methyl]-5-[5-(trifluoromethyl)-1,3-oxazol-2-yl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=CN=1)C(F)(F)F)C)C(=O)NCC1=NC=CC=C1C WDNHWVDNEIQLRZ-UHFFFAOYSA-N 0.000 claims 1
- JUHWVKQYWYOSDJ-UHFFFAOYSA-N 3-amino-6-methyl-N-[(3-methylpyridin-4-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=C(C=NC=C1)C JUHWVKQYWYOSDJ-UHFFFAOYSA-N 0.000 claims 1
- ZUJVIXBLZULWOW-UHFFFAOYSA-N 3-amino-6-methyl-N-[(5-methylpyridazin-3-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1N=NC=C(C=1)C ZUJVIXBLZULWOW-UHFFFAOYSA-N 0.000 claims 1
- WYWBMRCXTKZFJC-UHFFFAOYSA-N 3-amino-6-methyl-N-[(5-methylpyrimidin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=N1)C WYWBMRCXTKZFJC-UHFFFAOYSA-N 0.000 claims 1
- QKHDXTPWHFXOBR-UHFFFAOYSA-N 3-amino-6-methyl-N-[(5-methylpyrimidin-4-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=NC=C1C QKHDXTPWHFXOBR-UHFFFAOYSA-N 0.000 claims 1
- UORQARWBMJVOOK-UHFFFAOYSA-N 3-amino-6-methyl-N-[(6-methylimidazo[1,2-a]pyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1N=C2N(C=C(C=C2)C)C=1 UORQARWBMJVOOK-UHFFFAOYSA-N 0.000 claims 1
- FBYSUQFSSWLBLO-UHFFFAOYSA-N 3-amino-6-methyl-N-[(6-methylpyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1)C FBYSUQFSSWLBLO-UHFFFAOYSA-N 0.000 claims 1
- CKUYUXMNZQBVGN-UHFFFAOYSA-N 3-amino-6-methyl-N-[(6-methylpyridin-2-yl)methyl]-5-(1,3-oxazol-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)C)C(=O)NCC1=NC(=CC=C1)C CKUYUXMNZQBVGN-UHFFFAOYSA-N 0.000 claims 1
- HOBNWVBKFHQLFX-UHFFFAOYSA-N 3-amino-6-methyl-N-[(7-methylimidazo[1,2-a]pyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1N=C2N(C=CC(=C2)C)C=1 HOBNWVBKFHQLFX-UHFFFAOYSA-N 0.000 claims 1
- UBWVARXNKLCMHK-UHFFFAOYSA-N 3-amino-6-methyl-N-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1C)OCC(F)(F)F UBWVARXNKLCMHK-UHFFFAOYSA-N 0.000 claims 1
- ZVUCOXZVWGHNTR-UHFFFAOYSA-N 3-amino-6-methyl-N-[[3-methyl-5-(trifluoromethyl)pyridin-2-yl]methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1C)C(F)(F)F ZVUCOXZVWGHNTR-UHFFFAOYSA-N 0.000 claims 1
- WKXMZKGITWGWEG-UHFFFAOYSA-N 3-amino-N-(1,3-benzothiazol-2-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1SC2=C(N=1)C=CC=C2 WKXMZKGITWGWEG-UHFFFAOYSA-N 0.000 claims 1
- XGTKWNDXLAYYLQ-UHFFFAOYSA-N 3-amino-N-(1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazol-3-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C2=C(NN=1)CCCCC2 XGTKWNDXLAYYLQ-UHFFFAOYSA-N 0.000 claims 1
- YSMKXQYRQSHOSF-UHFFFAOYSA-N 3-amino-N-(1H-benzimidazol-2-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC2=C(N1)C=CC=C2 YSMKXQYRQSHOSF-UHFFFAOYSA-N 0.000 claims 1
- GTYKWMBRTYUIQO-UHFFFAOYSA-N 3-amino-N-(1H-imidazol-2-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1NC=CN=1 GTYKWMBRTYUIQO-UHFFFAOYSA-N 0.000 claims 1
- OPIMLKKIMXXTSQ-UHFFFAOYSA-N 3-amino-N-(1H-indol-7-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=CC=C2C=CNC=12 OPIMLKKIMXXTSQ-UHFFFAOYSA-N 0.000 claims 1
- DBRLOTLQSZBDBT-UHFFFAOYSA-N 3-amino-N-(2,2-difluoropropyl)-6-methyl-5-(1,3-oxazol-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CN=CO1)C)C(=O)NCC(C)(F)F DBRLOTLQSZBDBT-UHFFFAOYSA-N 0.000 claims 1
- ZINWXLFICUWTCK-UHFFFAOYSA-N 3-amino-N-(2,3-dihydro-1H-inden-2-yl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CC2=CC=CC=C2C1 ZINWXLFICUWTCK-UHFFFAOYSA-N 0.000 claims 1
- GQERYTFHFICEAJ-UHFFFAOYSA-N 3-amino-N-(2-fluorocyclopentyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1C(CCC1)F GQERYTFHFICEAJ-UHFFFAOYSA-N 0.000 claims 1
- NTTSAWSOLQXCEP-UHFFFAOYSA-N 3-amino-N-(2-methoxyethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCCOC NTTSAWSOLQXCEP-UHFFFAOYSA-N 0.000 claims 1
- NZXASGJITNTIHK-UHFFFAOYSA-N 3-amino-N-(3,3-difluorocyclopentyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CC(CC1)(F)F NZXASGJITNTIHK-UHFFFAOYSA-N 0.000 claims 1
- DVOHWWJUNILYRI-UHFFFAOYSA-N 3-amino-N-(4,4-difluorocyclohexyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1CCC(CC1)(F)F DVOHWWJUNILYRI-UHFFFAOYSA-N 0.000 claims 1
- BDQDGYHUZIAQBX-UHFFFAOYSA-N 3-amino-N-(6-fluoro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1C(CC=2C1=NC=CC=2)F BDQDGYHUZIAQBX-UHFFFAOYSA-N 0.000 claims 1
- NXTMTPGFLMRHFB-UHFFFAOYSA-N 3-amino-N-(6-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NC1C(CC=2C1=NC=CC=2)O NXTMTPGFLMRHFB-UHFFFAOYSA-N 0.000 claims 1
- UFTOXRPRXSQNBS-UHFFFAOYSA-N 3-amino-N-(cyclopropylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1CC1 UFTOXRPRXSQNBS-UHFFFAOYSA-N 0.000 claims 1
- JGCWMXYSVPQHQV-UHFFFAOYSA-N 3-amino-N-(imidazo[1,2-a]pyridin-3-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=CN=C2N1C=CC=C2 JGCWMXYSVPQHQV-UHFFFAOYSA-N 0.000 claims 1
- PCUZGAUOXDSYHQ-UHFFFAOYSA-N 3-amino-N-(isoquinolin-1-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC2=CC=CC=C12 PCUZGAUOXDSYHQ-UHFFFAOYSA-N 0.000 claims 1
- YZWUJKQHCDKFNQ-UHFFFAOYSA-N 3-amino-N-(isoquinolin-3-ylmethyl)-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1N=CC2=CC=CC=C2C=1 YZWUJKQHCDKFNQ-UHFFFAOYSA-N 0.000 claims 1
- ZSLZWKMLRRINQL-UHFFFAOYSA-N 3-amino-N-[(1-cyanocyclobutyl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1(CCC1)C#N ZSLZWKMLRRINQL-UHFFFAOYSA-N 0.000 claims 1
- MEJIKLZYHSXVNZ-GHMZBOCLSA-N 3-amino-N-[(1R,2R)-2-(dimethylamino)cyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@@H](CCC1)N(C)C MEJIKLZYHSXVNZ-GHMZBOCLSA-N 0.000 claims 1
- WRYXZZMQCVIXGS-TZMCWYRMSA-N 3-amino-N-[(1R,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@@H](CC2=CC=CC=C12)O WRYXZZMQCVIXGS-TZMCWYRMSA-N 0.000 claims 1
- FKQMZNXRCNLZNG-RKDXNWHRSA-N 3-amino-N-[(1R,2R)-2-hydroxycyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@@H](CCC1)O FKQMZNXRCNLZNG-RKDXNWHRSA-N 0.000 claims 1
- HZHNQRFZWZJIBP-NXEZZACHSA-N 3-amino-N-[(1R,2R)-2-hydroxycyclopentyl]-N,6-dimethyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N(C)[C@H]1[C@@H](CCC1)O HZHNQRFZWZJIBP-NXEZZACHSA-N 0.000 claims 1
- SVMIAXJIILANBL-GHMZBOCLSA-N 3-amino-N-[(1R,2S)-2-(methoxymethyl)cyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@H](CCC1)COC SVMIAXJIILANBL-GHMZBOCLSA-N 0.000 claims 1
- WRYXZZMQCVIXGS-GXTWGEPZSA-N 3-amino-N-[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@H](CC2=CC=CC=C12)O WRYXZZMQCVIXGS-GXTWGEPZSA-N 0.000 claims 1
- FKQMZNXRCNLZNG-BDAKNGLRSA-N 3-amino-N-[(1R,2S)-2-hydroxycyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1[C@H](CCC1)O FKQMZNXRCNLZNG-BDAKNGLRSA-N 0.000 claims 1
- SYLKQJNVCCOHPJ-ZDUSSCGKSA-N 3-amino-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1CCC2=CC=CC=C12 SYLKQJNVCCOHPJ-ZDUSSCGKSA-N 0.000 claims 1
- LRNQTTXWLSXPMO-QWRGUYRKSA-N 3-amino-N-[(1S,2R)-2-ethynylcyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1[C@H](CCC1)C#C LRNQTTXWLSXPMO-QWRGUYRKSA-N 0.000 claims 1
- GQERYTFHFICEAJ-BDAKNGLRSA-N 3-amino-N-[(1S,2R)-2-fluorocyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1[C@@H](CCC1)F GQERYTFHFICEAJ-BDAKNGLRSA-N 0.000 claims 1
- FPBNEPHOMPZBOE-QNSHHTMESA-N 3-amino-N-[(1S,2R,5R)-2-hydroxy-5-methylcyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1[C@@H](CC[C@H]1C)O FPBNEPHOMPZBOE-QNSHHTMESA-N 0.000 claims 1
- WRYXZZMQCVIXGS-JSGCOSHPSA-N 3-amino-N-[(1S,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1[C@H](CC2=CC=CC=C12)O WRYXZZMQCVIXGS-JSGCOSHPSA-N 0.000 claims 1
- FKQMZNXRCNLZNG-IUCAKERBSA-N 3-amino-N-[(1S,2S)-2-hydroxycyclopentyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1[C@H](CCC1)O FKQMZNXRCNLZNG-IUCAKERBSA-N 0.000 claims 1
- ZORHVZZREDUIEX-UHFFFAOYSA-N 3-amino-N-[(2,4-dimethyl-1,3-thiazol-5-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=C(N=C(S1)C)C ZORHVZZREDUIEX-UHFFFAOYSA-N 0.000 claims 1
- APHQIFLEGYOZGZ-UHFFFAOYSA-N 3-amino-N-[(2,6-dimethylpyridin-3-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C(=NC(=CC=1)C)C APHQIFLEGYOZGZ-UHFFFAOYSA-N 0.000 claims 1
- HZVIGKWCNYJDRC-UHFFFAOYSA-N 3-amino-N-[(2-chloropyridin-3-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C(=NC=CC=1)Cl HZVIGKWCNYJDRC-UHFFFAOYSA-N 0.000 claims 1
- CLDJEBRXQYDAMM-UHFFFAOYSA-N 3-amino-N-[(2-methoxypyridin-3-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C(=NC=CC=1)OC CLDJEBRXQYDAMM-UHFFFAOYSA-N 0.000 claims 1
- LCPUVNKELYTGJW-UHFFFAOYSA-N 3-amino-N-[(3,5-difluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1F)F LCPUVNKELYTGJW-UHFFFAOYSA-N 0.000 claims 1
- LJGCWMISUMSNLN-UHFFFAOYSA-N 3-amino-N-[(3,6-dimethylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1C)C LJGCWMISUMSNLN-UHFFFAOYSA-N 0.000 claims 1
- URJXWBHATSGCMA-UHFFFAOYSA-N 3-amino-N-[(3-chloro-5-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1Cl)F URJXWBHATSGCMA-UHFFFAOYSA-N 0.000 claims 1
- LRAXYOXNMXJNGJ-UHFFFAOYSA-N 3-amino-N-[(3-chloropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1Cl LRAXYOXNMXJNGJ-UHFFFAOYSA-N 0.000 claims 1
- MONVHXFEFUXUAA-UHFFFAOYSA-N 3-amino-N-[(3-chloropyridin-4-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=C(C=NC=C1)Cl MONVHXFEFUXUAA-UHFFFAOYSA-N 0.000 claims 1
- YJJUHYLNGQTMCV-UHFFFAOYSA-N 3-amino-N-[(3-cyclopropyl-5-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1C1CC1)F YJJUHYLNGQTMCV-UHFFFAOYSA-N 0.000 claims 1
- TXQSLQABCGQKED-UHFFFAOYSA-N 3-amino-N-[(3-ethoxypyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC=C1OCC TXQSLQABCGQKED-UHFFFAOYSA-N 0.000 claims 1
- NGIKEZGTLIKTIA-UHFFFAOYSA-N 3-amino-N-[(3-ethylpyrazin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CN=C1CC NGIKEZGTLIKTIA-UHFFFAOYSA-N 0.000 claims 1
- CHJWBESUIRADRT-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyrazin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CN=C1F CHJWBESUIRADRT-UHFFFAOYSA-N 0.000 claims 1
- XSUUESJJIMSZPQ-NSHDSACASA-N 3-amino-N-[(3R)-2,3-dihydro-1-benzofuran-3-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1COC2=C1C=CC=C2 XSUUESJJIMSZPQ-NSHDSACASA-N 0.000 claims 1
- XSUUESJJIMSZPQ-LLVKDONJSA-N 3-amino-N-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1COC2=C1C=CC=C2 XSUUESJJIMSZPQ-LLVKDONJSA-N 0.000 claims 1
- QERFQRBFPIABFX-UHFFFAOYSA-N 3-amino-N-[(4,6-dimethylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC(=C1)C)C QERFQRBFPIABFX-UHFFFAOYSA-N 0.000 claims 1
- ZVKULNHQDCIPBF-UHFFFAOYSA-N 3-amino-N-[(4,6-dimethylpyrimidin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC(=N1)C)C ZVKULNHQDCIPBF-UHFFFAOYSA-N 0.000 claims 1
- PCKMNWDCTCILPE-UHFFFAOYSA-N 3-amino-N-[(4-chloropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1)Cl PCKMNWDCTCILPE-UHFFFAOYSA-N 0.000 claims 1
- OMCZPQLZNYXDFP-UHFFFAOYSA-N 3-amino-N-[(4-fluoro-3-methylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1C)F OMCZPQLZNYXDFP-UHFFFAOYSA-N 0.000 claims 1
- BEHSCTTUOVVUTP-UHFFFAOYSA-N 3-amino-N-[(4-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=C1)F BEHSCTTUOVVUTP-UHFFFAOYSA-N 0.000 claims 1
- XDIGNIHDKZXDHD-UHFFFAOYSA-N 3-amino-N-[(4-methoxypyrimidin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=CC(=N1)OC XDIGNIHDKZXDHD-UHFFFAOYSA-N 0.000 claims 1
- AFAFIWIOSKBIPF-GFCCVEGCSA-N 3-amino-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@@H]1CCOC2=CC=CC=C12 AFAFIWIOSKBIPF-GFCCVEGCSA-N 0.000 claims 1
- AFAFIWIOSKBIPF-LBPRGKRZSA-N 3-amino-N-[(4S)-3,4-dihydro-2H-chromen-4-yl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)N[C@H]1CCOC2=CC=CC=C12 AFAFIWIOSKBIPF-LBPRGKRZSA-N 0.000 claims 1
- YBKHRDHIVLMDSZ-UHFFFAOYSA-N 3-amino-N-[(5-chloro-3-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1F)Cl YBKHRDHIVLMDSZ-UHFFFAOYSA-N 0.000 claims 1
- AFDAFZSBRDNYGO-UHFFFAOYSA-N 3-amino-N-[(5-chloropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1)Cl AFDAFZSBRDNYGO-UHFFFAOYSA-N 0.000 claims 1
- MYLODQWRSYKOAJ-UHFFFAOYSA-N 3-amino-N-[(5-cyclopropylpyrimidin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=N1)C1CC1 MYLODQWRSYKOAJ-UHFFFAOYSA-N 0.000 claims 1
- XYOFFBMLQJTSEN-UHFFFAOYSA-N 3-amino-N-[(5-ethylpyrimidin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=N1)CC XYOFFBMLQJTSEN-UHFFFAOYSA-N 0.000 claims 1
- XBCDYLYSXDVIHN-UHFFFAOYSA-N 3-amino-N-[(5-fluoro-3-methylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1C)F XBCDYLYSXDVIHN-UHFFFAOYSA-N 0.000 claims 1
- MAVPBMUOYYTDHB-UHFFFAOYSA-N 3-amino-N-[(5-fluoropyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1)F MAVPBMUOYYTDHB-UHFFFAOYSA-N 0.000 claims 1
- PFHWHBRUGJZKMJ-UHFFFAOYSA-N 3-amino-N-[(5-fluoropyrimidin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=N1)F PFHWHBRUGJZKMJ-UHFFFAOYSA-N 0.000 claims 1
- ZHIZKPSKBWALIR-UHFFFAOYSA-N 3-amino-N-[(6-fluoropyridin-3-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC=1C=NC(=CC=1)F ZHIZKPSKBWALIR-UHFFFAOYSA-N 0.000 claims 1
- HVWZNEVXTUCRHU-UHFFFAOYSA-N 3-amino-N-[(6-methoxy-3-methylpyridin-2-yl)methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1C)OC HVWZNEVXTUCRHU-UHFFFAOYSA-N 0.000 claims 1
- XHSDPYIDPOKTNT-UHFFFAOYSA-N 3-amino-N-[2-(4-fluorophenyl)-2-oxoethyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC(=O)C1=CC=C(C=C1)F XHSDPYIDPOKTNT-UHFFFAOYSA-N 0.000 claims 1
- PYKSAAIFKYCRII-UHFFFAOYSA-N 3-amino-N-[3-(3,3-difluoropyrrolidin-1-yl)propyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCCCN1CC(CC1)(F)F PYKSAAIFKYCRII-UHFFFAOYSA-N 0.000 claims 1
- MMMMMGJOJAWXHX-UHFFFAOYSA-N 3-amino-N-[[2,6-bis(difluoromethyl)pyridin-4-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=CC(=NC(=C1)C(F)F)C(F)F MMMMMGJOJAWXHX-UHFFFAOYSA-N 0.000 claims 1
- GPTFDJGPRANQEE-UHFFFAOYSA-N 3-amino-N-[[3-ethyl-5-(trifluoromethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC=C(C=C1CC)C(F)(F)F GPTFDJGPRANQEE-UHFFFAOYSA-N 0.000 claims 1
- BOMDZVLNAIGLEO-UHFFFAOYSA-N 3-amino-N-[[4,6-bis(difluoromethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC(=C1)C(F)F)C(F)F BOMDZVLNAIGLEO-UHFFFAOYSA-N 0.000 claims 1
- JKPZFBMPEQRPDM-UHFFFAOYSA-N 3-amino-N-[[5-methoxy-6-(trifluoromethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=C(C=C1)OC)C(F)(F)F JKPZFBMPEQRPDM-UHFFFAOYSA-N 0.000 claims 1
- DWVKGZAQIRTKJJ-UHFFFAOYSA-N 3-amino-N-[[6-(methoxymethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC=C1)COC DWVKGZAQIRTKJJ-UHFFFAOYSA-N 0.000 claims 1
- LBVUWJRSCXSAAN-UHFFFAOYSA-N 3-amino-N-[[6-chloro-4-(trifluoromethyl)pyridin-2-yl]methyl]-6-methyl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C)C(=O)NCC1=NC(=CC(=C1)C(F)(F)F)Cl LBVUWJRSCXSAAN-UHFFFAOYSA-N 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- NBXIOQTYZWAAEB-UHFFFAOYSA-N 6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidine Chemical compound C1=NC=C2CNCC2=N1 NBXIOQTYZWAAEB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- GNLXQLGPEBRQMB-UHFFFAOYSA-N N-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C=NC=C1)C(=O)NC=1OC=CN=1 GNLXQLGPEBRQMB-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- PQZIFBAUNRGTGG-UHFFFAOYSA-N NC=1CN(C(=C(N1)C=1OC=CN1)C)CC=1N=CN(C1C)C(C)C Chemical compound NC=1CN(C(=C(N1)C=1OC=CN1)C)CC=1N=CN(C1C)C(C)C PQZIFBAUNRGTGG-UHFFFAOYSA-N 0.000 claims 1
- KKBMSZAOSGZUBM-UHFFFAOYSA-N [3-amino-6-chloro-5-(triazol-2-yl)pyrazin-2-yl]-(8-bromo-3,4-dihydro-1H-isoquinolin-2-yl)methanone Chemical class BrC=1C=CC=C2CCN(CC=12)C(=O)C=1C(=NC(=C(N=1)Cl)N1N=CC=N1)N KKBMSZAOSGZUBM-UHFFFAOYSA-N 0.000 claims 1
- QIGRTIJLGUCHFD-UHFFFAOYSA-N [3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-(2-phenylazetidin-1-yl)methanone Chemical compound CC=1N=C(C(=NC=1C=1OC=CN=1)N)C(=O)N1C(CC1)C1=CC=CC=C1 QIGRTIJLGUCHFD-UHFFFAOYSA-N 0.000 claims 1
- XUULFPCWLYGDFF-UHFFFAOYSA-N [3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-(3,3-difluoropiperidin-1-yl)methanone Chemical compound FC1(CN(CCC1)C(=O)C=1C(=NC(=C(N=1)C)C=1OC=CN=1)N)F XUULFPCWLYGDFF-UHFFFAOYSA-N 0.000 claims 1
- MQYUXCATZHKXHB-UHFFFAOYSA-N [3-amino-6-methyl-5-(1,3-oxazol-2-yl)pyrazin-2-yl]-(6,8-dihydro-5H-1,7-naphthyridin-7-yl)methanone Chemical compound Cc1nc(C(=O)N2CCc3cccnc3C2)c(N)nc1-c1ncco1 MQYUXCATZHKXHB-UHFFFAOYSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 0 C*1*=C(*)C(C)=*1 Chemical compound C*1*=C(*)C(C)=*1 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462081262P | 2014-11-18 | 2014-11-18 | |
| US62/081,262 | 2014-11-18 | ||
| PCT/US2015/060509 WO2016081290A1 (en) | 2014-11-18 | 2015-11-13 | Aminopyrazine compounds with a2a antagonist properties |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020138418A Division JP2020193211A (ja) | 2014-11-18 | 2020-08-19 | Ａ２ａ拮抗薬特性を有するアミノピラジン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017533946A JP2017533946A (ja) | 2017-11-16 |
| JP2017533946A5 true JP2017533946A5 (OSRAM) | 2018-12-20 |
| JP6779204B2 JP6779204B2 (ja) | 2020-11-04 |
Family
ID=56014406
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017526527A Expired - Fee Related JP6779204B2 (ja) | 2014-11-18 | 2015-11-13 | Ａ２ａ拮抗薬特性を有するアミノピラジン化合物 |
| JP2020138418A Withdrawn JP2020193211A (ja) | 2014-11-18 | 2020-08-19 | Ａ２ａ拮抗薬特性を有するアミノピラジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020138418A Withdrawn JP2020193211A (ja) | 2014-11-18 | 2020-08-19 | Ａ２ａ拮抗薬特性を有するアミノピラジン化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10472347B2 (OSRAM) |
| EP (1) | EP3220910B1 (OSRAM) |
| JP (2) | JP6779204B2 (OSRAM) |
| KR (1) | KR20170083136A (OSRAM) |
| CN (1) | CN107106558A (OSRAM) |
| AU (1) | AU2015350315B2 (OSRAM) |
| BR (1) | BR112017010261A2 (OSRAM) |
| CA (1) | CA2967944C (OSRAM) |
| MX (1) | MX381180B (OSRAM) |
| RU (1) | RU2727805C2 (OSRAM) |
| WO (1) | WO2016081290A1 (OSRAM) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY199046A (en) * | 2016-07-12 | 2023-10-11 | Revolution Medicines Inc | 2,5-disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines as allosteric shp2 inhibitors |
| SG11201906209SA (en) | 2017-01-23 | 2019-08-27 | Revolution Medicines Inc | Bicyclic compounds as allosteric shp2 inhibitors |
| AU2018210196B2 (en) | 2017-01-23 | 2022-06-02 | Revolution Medicines, Inc. | Pyridine compounds as allosteric SHP2 inhibitors |
| WO2018161910A1 (zh) * | 2017-03-07 | 2018-09-13 | 广州再极医药科技有限公司 | 氨基嘧啶并五元杂环化合物、其中间体、制备方法、药物组合物及应用 |
| JP2020527593A (ja) | 2017-07-18 | 2020-09-10 | ニューベイション・バイオ・インコーポレイテッドＮｕｖａｔｉｏｎ Ｂｉｏ Ｉｎｃ． | １，８−ナフチリジノン化合物およびその使用 |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| CA3073915A1 (en) | 2017-08-31 | 2019-03-07 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating adenosine a2b receptor and adenosine a2a receptor |
| CN111212834B (zh) | 2017-10-12 | 2024-01-19 | 锐新医药公司 | 作为变构shp2抑制剂的吡啶、吡嗪和三嗪化合物 |
| EP3723754A4 (en) | 2017-12-13 | 2021-05-19 | Merck Sharp & Dohme Corp. | IMIDAZO [1,2-C] QUINAZOLINE-5-AMINE COMPOUNDS WITH PROPERTIES OF A2A ANTAGONIST |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| BR112021002642A2 (pt) | 2018-08-16 | 2021-05-04 | Innate Tumor Immunity, Inc. | compostos de 4-amino-1h-imidazo[4,5-c]quinolina substituídos e métodos aprimorados para a preparação dos mesmos |
| EP3616753A1 (en) * | 2018-08-31 | 2020-03-04 | Corvus Pharmaceuticals, Inc. | Compounds for modulating adenosine a2b receptor and adenosine a2a receptor |
| CA3119774A1 (en) | 2018-11-20 | 2020-05-28 | Merck Sharp & Dohme Corp. | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| EP3883576B1 (en) | 2018-11-20 | 2025-12-17 | Merck Sharp & Dohme LLC | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019385905B2 (en) | 2018-11-30 | 2023-01-12 | Merck Sharp & Dohme Llc | 9-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| KR20210097152A (ko) | 2018-11-30 | 2021-08-06 | 머크 샤프 앤드 돔 코포레이션 | 아데노신 수용체 길항제로서의 7-, 8- 및 10-치환된 아미노 트리아졸로 퀴나졸린 유도체, 제약 조성물 및 그의 용도 |
| AU2020205753B2 (en) | 2019-01-11 | 2025-05-29 | Omeros Corporation | Methods and compositions for treating cancer |
| CN113939291A (zh) | 2019-01-18 | 2022-01-14 | 诺维逊生物股份有限公司 | 1,8-萘啶酮化合物及其用途 |
| MX2021008650A (es) | 2019-01-18 | 2021-11-03 | Nuvation Bio Inc | Compuestos heterociclicos como antagonistas de adenosina. |
| TW202128650A (zh) * | 2019-10-11 | 2021-08-01 | 德商拜耳動物保健有限公司 | 作為殺蟲劑之新穎的雜芳基取代之吡𠯤衍生物 |
| CN111285798A (zh) * | 2020-04-09 | 2020-06-16 | 阿里生物新材料（常州）有限公司 | 一种（3-环丙基吡啶-2-基）甲胺盐酸盐的合成方法 |
| CN111423364A (zh) * | 2020-05-19 | 2020-07-17 | 阿里生物新材料（常州）有限公司 | 一种（3-环丙基吡啶-2-基）甲胺的合成方法 |
| EP3929189A1 (en) * | 2020-06-25 | 2021-12-29 | Bayer Animal Health GmbH | Novel heteroaryl-substituted pyrazine derivatives as pesticides |
| MX2023011269A (es) | 2021-03-23 | 2024-01-17 | Bioage Labs Inc | Inhibidores del inflamasoma nlrp3. |
| US11787805B2 (en) | 2022-01-28 | 2023-10-17 | BioAge Labs, Inc. | N-oxide inhibitors of NLRP3 inflammasome |
| KR20250004779A (ko) | 2022-04-13 | 2025-01-08 | 길리애드 사이언시즈, 인코포레이티드 | Trop-2 발현 암을 치료하기 위한 병용 요법 |
| US20250074870A1 (en) * | 2023-03-30 | 2025-03-06 | Brandeis University | Solid-solid phase change aromatic azo compounds, method of manufacture, and use for thermal energy storage and release |
| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| DE69428977T2 (de) | 1993-07-27 | 2002-07-11 | Kyowa Hakko Kogyo Co., Ltd. | Arzneimittel gegen Parkinsonsche Krankheit |
| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| TWI288137B (en) | 2000-05-26 | 2007-10-11 | Schering Corp | Adenosine A2a receptor antagonists |
| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| US20060135523A1 (en) * | 2003-06-18 | 2006-06-22 | Astrazeneca Ab | 2-substituted 5,6-diaryl-pyrazine derivatives as cb1 modulator |
| KR20060123208A (ko) * | 2003-10-27 | 2006-12-01 | 아스테라스 세이야쿠 가부시키가이샤 | 피라진 유도체 및 이의 약학적 용도 |
| US20060199828A1 (en) * | 2005-03-04 | 2006-09-07 | Georg Jaeschke | Pyrazine-2-carboxyamide derivatives |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| US20120065205A1 (en) | 2009-06-01 | 2012-03-15 | Mercer Swati P | Pyrazine carboxamide orexin receptor antagonists |
-
2015
- 2015-11-13 JP JP2017526527A patent/JP6779204B2/ja not_active Expired - Fee Related
- 2015-11-13 BR BR112017010261-7A patent/BR112017010261A2/pt not_active IP Right Cessation
- 2015-11-13 MX MX2017006483A patent/MX381180B/es unknown
- 2015-11-13 US US15/525,788 patent/US10472347B2/en active Active
- 2015-11-13 CA CA2967944A patent/CA2967944C/en not_active Expired - Fee Related
- 2015-11-13 CN CN201580073488.3A patent/CN107106558A/zh active Pending
- 2015-11-13 KR KR1020177016281A patent/KR20170083136A/ko not_active Withdrawn
- 2015-11-13 RU RU2017120853A patent/RU2727805C2/ru active
- 2015-11-13 WO PCT/US2015/060509 patent/WO2016081290A1/en not_active Ceased
- 2015-11-13 EP EP15861650.8A patent/EP3220910B1/en active Active
- 2015-11-13 AU AU2015350315A patent/AU2015350315B2/en not_active Ceased
-
2020
- 2020-08-19 JP JP2020138418A patent/JP2020193211A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017533946A5 (OSRAM) | ||
| RU2017120853A (ru) | Аминопиразиновые соединения со свойствами антагониста a2a | |
| JP4672820B2 (ja) | ＧＡＢＡα５リガンドとしての置換１，２，４−トリアゾロ［３，４−ａ］フタラジン誘導体 | |
| KR101819433B1 (ko) | 인돌린-2-온 또는 피롤로-피리딘-2-온 유도체 | |
| US9321756B2 (en) | Azole compounds as PIM inhibitors | |
| MX2011012345A (es) | Inhibidores de pi3k/mtor basados en benzoxazepinas contra enfermedades proliferativas. | |
| JP2016500073A5 (OSRAM) | ||
| CN111556871B (zh) | 作为PDE1抑制剂的1H-吡唑并[4,3-b]吡啶 | |
| JP2014528446A5 (OSRAM) | ||
| JP2013527173A5 (OSRAM) | ||
| JP2013508404A5 (OSRAM) | ||
| JP2017530960A5 (OSRAM) | ||
| RU2007101544A (ru) | Антагонисты рецепторов высвобождающего гонадотропин гормона | |
| JP2013508403A5 (OSRAM) | ||
| ME02437B (me) | Disupstituirani oktahidropirolo[3,4-c]piroli kao modulatori oreksin receptora | |
| WO2010126895A1 (en) | Inhibitors of pi3 kinase and / or mtor | |
| ME02802B (me) | P2x7 modulatori | |
| JP2013508405A5 (OSRAM) | ||
| RU2015114936A (ru) | Ингибиторы серин/треонинкиназы | |
| CN120826403A (zh) | Shp2抑制剂化合物及其应用 | |
| KR101898364B1 (ko) | 인돌린-2-온 및 1,3-다이하이드로-피롤로[3,2-c]피리딘-2-온 유도체 | |
| CN114502537A (zh) | 突变型idh2抑制剂及其应用 | |
| KR20150047609A (ko) | 피리딘 유도체 및 의약 | |
| RU2015125306A (ru) | Новые соединения ингибиторы фосфодиэстеразы типа 10а | |
| RU2020134947A (ru) | Производные конденсированной циклической мочевины в антагонист crhr2 |