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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| IL311645B2 (en) * | 2016-07-12 | 2025-11-01 | Revolution Medicines Inc | 2,5- disubstituted 3-methyl pyrazines and 2,5,6-trisubstituted 3-methyl pyrazines asallosteric shp2 inhibitors |
| CA3051054A1 (en) | 2017-01-23 | 2018-07-26 | Revolution Medicines, Inc. | Pyridine compounds as allosteric shp2 inhibitors |
| CN110446709B (zh) | 2017-01-23 | 2023-09-12 | 锐新医药公司 | 作为变构shp2抑制剂的二环化合物 |
| CN108570054B (zh) * | 2017-03-07 | 2021-07-16 | 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 |
| CA3070073A1 (en) | 2017-07-18 | 2019-01-24 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| JP2020527588A (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． | アデノシンアンタゴニストとしてのヘテロ環式化合物 |
| JP2020532541A (ja) | 2017-08-31 | 2020-11-12 | コーバス・ファーマシューティカルズ・インコーポレイテッド | アデノシンａ２ｂ受容体およびアデノシンａ２ａ受容体を調節するための化合物および方法 |
| BR112020007058A2 (pt) | 2017-10-12 | 2020-10-06 | Revolution Medicines, Inc. | compostos de piridina, pirazina, e triazina como inibidores de shp2 alostéricos |
| US11498923B2 (en) | 2017-12-13 | 2022-11-15 | Merck Sharp & Dohme Llc | Substituted imidazo[1,2-c]quinazolines as A2A antagonists |
| BR112020009757A2 (pt) | 2017-12-15 | 2020-11-03 | Revolution Medicines, Inc. | compostos policíclicos como inibidores alostéricos de shp2 |
| SG11202101486RA (en) | 2018-08-16 | 2021-03-30 | Innate Tumor Immunity Inc | Substitued 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 |
| JP2022507734A (ja) | 2018-11-20 | 2022-01-18 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換アミノトリアゾロピリミジン及びアミノトリアゾロピラジンアデノシン受容体アンタゴニスト、医薬組成物及びそれらの使用 |
| US12414952B2 (en) | 2018-11-20 | 2025-09-16 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| JP2022511778A (ja) | 2018-11-30 | 2022-02-01 | メルク・シャープ・アンド・ドーム・コーポレーション | アデノシン受容体拮抗薬としての７－、８－及び１０－置換されたアミノトリアゾロキナゾリン誘導体、医薬組成物及びそれらの使用 |
| AR117164A1 (es) | 2018-11-30 | 2021-07-14 | Merck Sharp & Dohme | Derivados de amino-triazoloquinazolina 9-sustituidos como antagonistas del receptor de adenosina, composiciones farmacéuticas y su uso para el tratamiento de diversos tipos de cáncer |
| WO2020146795A1 (en) | 2019-01-11 | 2020-07-16 | Omeros Corporation | Methods and compositions for treating cancer |
| WO2020150674A1 (en) | 2019-01-18 | 2020-07-23 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| US11254670B2 (en) | 2019-01-18 | 2022-02-22 | Nuvation Bio Inc. | 1,8-naphthyridinone compounds and uses thereof |
| 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 |
| CN117157278A (zh) * | 2021-03-23 | 2023-12-01 | 柏奥艾奇实验室公司 | Nlrp3炎性体的抑制剂 |
| EP4469460A1 (en) | 2022-01-28 | 2024-12-04 | Bioage Labs, Inc. | N-oxide inhibitors of nlrp3 inflammasome |
| AU2023252914A1 (en) | 2022-04-13 | 2024-10-17 | Arcus Biosciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| 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 |
| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | 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 |
| US5565460A (en) | 1993-07-27 | 1996-10-15 | Kyowa Hakko Koygo Co., Ltd. | Therapeutic purine agents 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 |
| PT1283839E (pt) | 2000-05-26 | 2005-08-31 | Schering Corp | Antagonistas do receptor a2a da adenosina |
| 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. |
| CA2543644A1 (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
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2020
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