JP2017533946A5 - - Google Patents
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- 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
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- -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
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- 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
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| CN116478131A (zh) * | 2016-07-12 | 2023-07-25 | 锐新医药公司 | 作为变构shp2抑制剂的2,5-双取代型及2,5,6-三取代型3-甲基吡嗪 |
| CN110431134A (zh) | 2017-01-23 | 2019-11-08 | 锐新医药公司 | 作为变构shp2抑制剂的吡啶化合物 |
| AU2018210770B2 (en) | 2017-01-23 | 2022-03-24 | Revolution Medicines, Inc. | Bicyclic compounds as allosteric SHP2 inhibitors |
| JP7071389B2 (ja) * | 2017-03-07 | 2022-05-18 | グアンジョウ マキシノベル ファーマシューティカルズ カンパニー リミテッド | アミノピリミジン縮合５員複素環化合物、その中間体、製造方法、薬物組成物および使用 |
| EP3654982A4 (en) | 2017-07-18 | 2021-04-14 | Nuvation Bio Inc. | 1,8-NAPHTHYRIDINONE COMPOUNDS AND THEIR USES |
| EP3654978A4 (en) | 2017-07-18 | 2021-03-31 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS USED AS ADENOSINE ANTAGONISTS |
| AU2018325451A1 (en) | 2017-08-31 | 2020-03-05 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating adenosine A2B receptor and adenosine A2A receptor |
| KR20200070295A (ko) | 2017-10-12 | 2020-06-17 | 레볼루션 메디슨즈, 인크. | 알로스테릭 shp2 억제제로서의 피리딘, 피라진 및 트리아진 화합물 |
| 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 |
| CN111433205B (zh) | 2017-12-15 | 2024-01-19 | 锐新医药公司 | 作为变构shp2抑制剂的多环化合物 |
| US11572360B2 (en) | 2018-08-16 | 2023-02-07 | Innate Tumor Immunity, Inc. | Substituted 4-amino-1H-imidazo[4,5-c]quinoline compounds and improved methods for their preparation |
| US20200079793A1 (en) * | 2018-08-31 | 2020-03-12 | Corvus Pharmaceuticals, Inc. | Compounds and methods for modulating adenosine a2b receptor and adenosine a2a receptor |
| WO2020106558A1 (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 |
| MX2021006012A (es) | 2018-11-30 | 2021-07-06 | Merck Sharp & Dohme | Derivados de amino triazolo quinazolina 7-, 8-, y 10-sustituidos como antagonistas de receptor de adenosina, composiciones farmaceuticas y su uso. |
| JOP20210117A1 (ar) | 2018-11-30 | 2023-01-30 | Merck Sharp & Dohme | مشتقات أمينو ترايازولو كوينازولين بها استبدال في الموضع-9 كمضادات مستقبل أدينوزين، تركيبات صيدلانية واستخدامها |
| SG11202106963YA (en) | 2019-01-11 | 2021-07-29 | Omeros Corp | Methods and compositions for treating cancer |
| US11254670B2 (en) | 2019-01-18 | 2022-02-22 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| 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 |
| AU2022241754A1 (en) | 2021-03-23 | 2023-10-19 | BioAge Labs, Inc. | Inhibitors of nlrp3 inflammasome |
| WO2023147468A1 (en) | 2022-01-28 | 2023-08-03 | 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 |
| US12516018B2 (en) * | 2023-03-30 | 2026-01-06 | Brandeis University | Solid-solid phase change aromatic azo compounds, method of manufacture, and use for thermal energy storage and release |
| WO2025137640A1 (en) | 2023-12-22 | 2025-06-26 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025207644A1 (en) | 2024-03-26 | 2025-10-02 | BioAge Labs, Inc. | Inhibitors of nlrp3 inflammasome |
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| 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 |
| EP0666079B1 (en) | 1993-07-27 | 2001-11-07 | Kyowa Hakko Kogyo Co., Ltd. | Remedy for parkinson's disease |
| 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 |
| SK287748B6 (sk) | 2000-05-26 | 2011-08-04 | Schering Corporation | Substituované 5-amino-pyrazolo[4,3-e]-1,2,4-triazolo[1,5- c]pyrimidíny, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie |
| SE0203754D0 (sv) | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| EP1641779A1 (en) | 2003-06-18 | 2006-04-05 | AstraZeneca AB | 2-substitued 5, 6-diaryl-pyrazine derivatives as cb1 modulator. |
| WO2005040151A1 (en) * | 2003-10-27 | 2005-05-06 | Astellas Pharma Inc. | Pyrazine derivatives and pharmaceutical use thereof |
| 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. |
| WO2010141275A1 (en) * | 2009-06-01 | 2010-12-09 | Merck Sharp & Dohme Corp. | Pyrazine carboxamide orexin receptor antagonists |
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- 2015-11-13 WO PCT/US2015/060509 patent/WO2016081290A1/en not_active Ceased
- 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 BR BR112017010261-7A patent/BR112017010261A2/pt not_active IP Right Cessation
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2020
- 2020-08-19 JP JP2020138418A patent/JP2020193211A/ja not_active Withdrawn
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