JP7540996B2 - ピラジン化合物およびその使用 - Google Patents
ピラジン化合物およびその使用 Download PDFInfo
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- JP7540996B2 JP7540996B2 JP2021507992A JP2021507992A JP7540996B2 JP 7540996 B2 JP7540996 B2 JP 7540996B2 JP 2021507992 A JP2021507992 A JP 2021507992A JP 2021507992 A JP2021507992 A JP 2021507992A JP 7540996 B2 JP7540996 B2 JP 7540996B2
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- JP
- Japan
- Prior art keywords
- amino
- methyl
- pyrazine
- carboxamide
- pyridin
- 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.)
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- 150000003216 pyrazines Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 305
- -1 cyano, amino, carbamoyl Chemical group 0.000 claims description 282
- 150000001875 compounds Chemical class 0.000 claims description 256
- 229920006395 saturated elastomer Polymers 0.000 claims description 91
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 87
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 61
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 61
- 150000002367 halogens Chemical group 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 55
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 51
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 49
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 108050000203 Adenosine receptors Proteins 0.000 claims description 45
- 102000009346 Adenosine receptors Human genes 0.000 claims description 45
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 44
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 42
- 239000004202 carbamide Chemical group 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 35
- 206010028980 Neoplasm Diseases 0.000 claims description 33
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 31
- 201000011510 cancer Diseases 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 25
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002246 antineoplastic agent Substances 0.000 claims description 20
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 15
- 206010006187 Breast cancer Diseases 0.000 claims description 14
- 208000026310 Breast neoplasm Diseases 0.000 claims description 14
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 14
- 125000003566 oxetanyl group Chemical group 0.000 claims description 14
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 14
- 206010060862 Prostate cancer Diseases 0.000 claims description 13
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 13
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 229910019142 PO4 Inorganic materials 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
- 239000010452 phosphate Substances 0.000 claims description 12
- XFOBAVRDEMQIJK-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)CC(C)O)C(=O)NCC1=C(C=CC=C1F)F Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)CC(C)O)C(=O)NCC1=C(C=CC=C1F)F XFOBAVRDEMQIJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- BNUHGMMHKOYFQZ-UHFFFAOYSA-N 3-amino-N-[1-(2,6-difluorophenyl)ethyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C)C(=O)NC(C)C1=C(C=CC=C1F)F BNUHGMMHKOYFQZ-UHFFFAOYSA-N 0.000 claims description 9
- OIQMAQQAOWDFQD-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1F)F Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1F)F OIQMAQQAOWDFQD-UHFFFAOYSA-N 0.000 claims description 9
- 229940127089 cytotoxic agent Drugs 0.000 claims description 9
- NSSAUZSHAJHJED-UHFFFAOYSA-N 3-amino-N-[[6-[3-(dimethylamino)azetidin-1-yl]pyridin-2-yl]methyl]-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1=NC(=CC=C1)N1CC(C1)N(C)C NSSAUZSHAJHJED-UHFFFAOYSA-N 0.000 claims description 8
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 8
- VAWDHPQFXGMSON-UHFFFAOYSA-N N-[[3-amino-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)pyrazin-2-yl]methyl]pyridine-2-carboxamide Chemical compound N1=C(C=CC=C1)C(=O)NCC1=NC(=C(N=C1N)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C VAWDHPQFXGMSON-UHFFFAOYSA-N 0.000 claims description 8
- KBGVDFHXSWNESA-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)N1N=CC=C1)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=C1)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC KBGVDFHXSWNESA-UHFFFAOYSA-N 0.000 claims description 8
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- FZFPWFXPMOWVTG-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-N-[[3-(2-hydroxyethoxy)pyridin-2-yl]methyl]-6-(3-methylbenzimidazol-5-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC2=C(N(C=N2)C)C=1)C(=O)NCC1=NC=CC=C1OCCO FZFPWFXPMOWVTG-UHFFFAOYSA-N 0.000 claims description 7
- HUXHJCDGQAHSQH-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-N-[[3-(2-methoxyethoxy)pyridin-2-yl]methyl]-6-(3-methylbenzimidazol-5-yl)pyrazine-2-carboxamide Chemical compound C(COC)OC1=C(CNC(=O)C2=C(N=C(C3=CC=C(F)C=C3)C(=N2)C2=CC=C3N=CN(C3=C2)C)N)N=CC=C1 HUXHJCDGQAHSQH-UHFFFAOYSA-N 0.000 claims description 7
- DBDWXJXIFRFRHO-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)-N-[(3-fluoropyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C)C(=O)NCC1=NC=CC=C1F DBDWXJXIFRFRHO-UHFFFAOYSA-N 0.000 claims description 7
- FDQKCQSOISWQCX-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-N-[(2-methoxyphenyl)methyl]-5-phenylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=CC=C1)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC FDQKCQSOISWQCX-UHFFFAOYSA-N 0.000 claims description 7
- XPMYHLLHPNMYCG-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-N-[(4-fluoro-2-methoxyphenyl)methyl]-5-(4-fluorophenyl)pyrazine-2-carboxamide Chemical compound FC1=CC=C(C2=C(C3=CC(C)=NC(=C3)C)N=C(C(=N2)N)C(=O)NCC2=CC=C(F)C=C2OC)C=C1 XPMYHLLHPNMYCG-UHFFFAOYSA-N 0.000 claims description 7
- STPBWTWFHSYCQD-UHFFFAOYSA-N 3-amino-6-imidazo[1,2-a]pyridin-6-yl-N-[(5-methyl-1,3-thiazol-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=1C=CC=2N(C=1)C=CN=2)C(=O)NCC=1N=CSC=1C STPBWTWFHSYCQD-UHFFFAOYSA-N 0.000 claims description 7
- ONJOCLUBNIHGFR-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-6-[1-(2-methoxyethyl)-6-oxopyridin-3-yl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)CCOC)C(=O)NCC1=C(C=CC=C1F)F ONJOCLUBNIHGFR-UHFFFAOYSA-N 0.000 claims description 7
- RDQGDQIQBDJGKQ-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-2-yl)methyl]-6-imidazo[1,2-a]pyridin-6-yl-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C=CN=2)C(=O)NCC1=NC=CC=C1F RDQGDQIQBDJGKQ-UHFFFAOYSA-N 0.000 claims description 7
- MDYJYOZAXGCVQJ-UHFFFAOYSA-N 3-amino-N-[(4-aminopyrimidin-2-yl)methyl]-6-imidazo[1,2-a]pyridin-6-yl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC2=NC=CN2C=1)C(=O)NCC1=NC(=CC=N1)N)N MDYJYOZAXGCVQJ-UHFFFAOYSA-N 0.000 claims description 7
- XOHOLZCXFDPBFD-UHFFFAOYSA-N 3-amino-N-[[2-(difluoromethoxy)phenyl]methyl]-5-(4-fluorophenyl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1)OC(F)F XOHOLZCXFDPBFD-UHFFFAOYSA-N 0.000 claims description 7
- DKDYAEYZJZWBSN-UHFFFAOYSA-N 3-amino-N-[[6-(dimethylamino)pyridin-2-yl]methyl]-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(C1=C1C=CC(F)=C[CH]1)=C1C=C(C)N=C(C)[CH]1)C(=O)NCC1=NC(N(C)C)=CC=C1)N DKDYAEYZJZWBSN-UHFFFAOYSA-N 0.000 claims description 7
- 229940045513 CTLA4 antagonist Drugs 0.000 claims description 7
- OXGKLOIFOGXJFF-UHFFFAOYSA-N N-[[3-amino-5-(4-fluorophenyl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazin-2-yl]methyl]-2-fluoro-6-(trifluoromethyl)benzamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C)CNC(C1=C(C=CC=C1C(F)(F)F)F)=O OXGKLOIFOGXJFF-UHFFFAOYSA-N 0.000 claims description 7
- SEPAGMWYACTNRV-UHFFFAOYSA-N N-[[3-amino-5-(5-methylfuran-2-yl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazin-2-yl]methyl]-2,6-difluorobenzamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=CC=1)C)C1=CN(C(C=C1)=O)C)CNC(C1=C(C=CC=C1F)F)=O SEPAGMWYACTNRV-UHFFFAOYSA-N 0.000 claims description 7
- OMGHKDXZUABNKJ-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)F Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)F OMGHKDXZUABNKJ-UHFFFAOYSA-N 0.000 claims description 7
- LTERGMQXYSNJNP-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC LTERGMQXYSNJNP-UHFFFAOYSA-N 0.000 claims description 7
- NCEPVSSUMDJDOB-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)N1CC(OC(C1)C)C)C(=O)NCC1=C(C=CC=C1F)F Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)N1CC(OC(C1)C)C)C(=O)NCC1=C(C=CC=C1F)F NCEPVSSUMDJDOB-UHFFFAOYSA-N 0.000 claims description 7
- AHFPNXMNUGCLBN-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C=1OC(=CC=1)C)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1F)F Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=CC=1)C)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1F)F AHFPNXMNUGCLBN-UHFFFAOYSA-N 0.000 claims description 7
- AARGAQMIZGRRAW-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)N1N=C(C=C1)C)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC Chemical compound NC=1C(=NC(=C(N=1)N1N=C(C=C1)C)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC AARGAQMIZGRRAW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000002955 immunomodulating agent Substances 0.000 claims description 7
- NELVYYIXUVGYJO-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-6-[1-(3-hydroxypropyl)-6-oxopyridin-3-yl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound C1(=C(N=C(C(C=2OC=CN=2)=N1)C=1C=CC(=O)N(C=1)CCCO)C(=O)NCC1=C(F)C=CC=C1F)N NELVYYIXUVGYJO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- XYHMSQIYQHPLCB-UHFFFAOYSA-N 3-amino-N-[(2-dimethylphosphoryl-6-fluorophenyl)methyl]-6-imidazo[1,2-a]pyridin-6-yl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound P(=O)(C1=C(CNC(=O)C2=C(N)N=C(C=3OC=CN=3)C(=N2)C=2C=CC3=NC=CN3C=2)C(F)=CC=C1)(C)C XYHMSQIYQHPLCB-UHFFFAOYSA-N 0.000 claims description 5
- GYSSUJQTLZXOER-UHFFFAOYSA-N 3-amino-N-[[3-(dimethylamino)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C)C(=O)NCC1=NC=CC=C1N(C)C GYSSUJQTLZXOER-UHFFFAOYSA-N 0.000 claims description 5
- HWDGUISORQAXSB-UHFFFAOYSA-N 3-amino-N-[[6-(dimethylamino)pyridin-2-yl]methyl]-5-(4-fluorophenyl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C)C(=O)NCC1=NC(=CC=C1)N(C)C HWDGUISORQAXSB-UHFFFAOYSA-N 0.000 claims description 5
- 201000006474 Brain Ischemia Diseases 0.000 claims description 5
- 206010007558 Cardiac failure chronic Diseases 0.000 claims description 5
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- PDFSASJYYXKZAG-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C(=CC=C1)N(C)C)F Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C(=CC=C1)N(C)C)F PDFSASJYYXKZAG-UHFFFAOYSA-N 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 206010008118 cerebral infarction Diseases 0.000 claims description 5
- 230000007278 cognition impairment Effects 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 5
- 229960001756 oxaliplatin Drugs 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- AILIQICGWSPSSV-UHFFFAOYSA-N 3-amino-6-(1-cyclopropyl-6-oxopyridin-3-yl)-N-[(2,6-difluorophenyl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C1CC1)C(=O)NCC1=C(C=CC=C1F)F AILIQICGWSPSSV-UHFFFAOYSA-N 0.000 claims description 4
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- XEQNKKLQRUCWAY-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[1-(oxolan-2-yl)ethyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC(C)C1OCCC1 XEQNKKLQRUCWAY-UHFFFAOYSA-N 0.000 claims 1
- BJBVHWLXPNDPFC-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[2-(2-oxopyridin-1-yl)ethyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCN1C(C=CC=C1)=O BJBVHWLXPNDPFC-UHFFFAOYSA-N 0.000 claims 1
- VRIBPMPJARAECC-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[2-(2-oxopyrrolidin-1-yl)ethyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCN1C(CCC1)=O VRIBPMPJARAECC-UHFFFAOYSA-N 0.000 claims 1
- NYFKVFSOFNXRIG-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[2-(trifluoromethoxy)ethyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCOC(F)(F)F NYFKVFSOFNXRIG-UHFFFAOYSA-N 0.000 claims 1
- ZMNJVFVXFGTUGF-CQSZACIVSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(2R)-oxolan-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1OCCC1 ZMNJVFVXFGTUGF-CQSZACIVSA-N 0.000 claims 1
- XOIIWYZETSWYDO-CQSZACIVSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(2R)-pyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1NCCC1 XOIIWYZETSWYDO-CQSZACIVSA-N 0.000 claims 1
- ZMNJVFVXFGTUGF-AWEZNQCLSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(2S)-oxolan-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@H]1OCCC1 ZMNJVFVXFGTUGF-AWEZNQCLSA-N 0.000 claims 1
- XOIIWYZETSWYDO-AWEZNQCLSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(2S)-pyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound O=C(C1=C(N)N=C(C=2OC=CN=2)C(=N1)C=1C=CC2=NC=C(N2C=1)C)NC[C@H]1NCCC1 XOIIWYZETSWYDO-AWEZNQCLSA-N 0.000 claims 1
- QFRUAJNAMIIGGK-CYBMUJFWSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(3R)-oxolan-3-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1COCC1 QFRUAJNAMIIGGK-CYBMUJFWSA-N 0.000 claims 1
- QFRUAJNAMIIGGK-ZDUSSCGKSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[[(3S)-oxolan-3-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@H]1COCC1 QFRUAJNAMIIGGK-ZDUSSCGKSA-N 0.000 claims 1
- KEDAZDLPZPMWQK-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-propan-2-ylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC(C)C KEDAZDLPZPMWQK-UHFFFAOYSA-N 0.000 claims 1
- CSPGVTLXRQCNBP-QGZVFWFLSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(3-methylpyrazol-1-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=C(C=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1N(CCC1)C CSPGVTLXRQCNBP-QGZVFWFLSA-N 0.000 claims 1
- CSPGVTLXRQCNBP-KRWDZBQOSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(3-methylpyrazol-1-yl)-N-[[(2S)-1-methylpyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=C(C=C1)C)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@H]1N(CCC1)C CSPGVTLXRQCNBP-KRWDZBQOSA-N 0.000 claims 1
- GMXGCLKOZIZXTB-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-(oxan-4-ylmethyl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1CCOCC1 GMXGCLKOZIZXTB-UHFFFAOYSA-N 0.000 claims 1
- OGTBKCORUXUJIZ-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-(oxolan-2-ylmethyl)-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1OCCC1 OGTBKCORUXUJIZ-UHFFFAOYSA-N 0.000 claims 1
- IWKMGKXOEGWCGN-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-(oxolan-3-ylmethyl)-5-pyridin-2-ylpyrazine-2-carboxamide Chemical compound C1(=C(N)N=C(C2=NC=CC=C2)C(=N1)C=1C=CC2=NC=C(N2C=1)C)C(=O)NCC1COCC1 IWKMGKXOEGWCGN-UHFFFAOYSA-N 0.000 claims 1
- KLPCGAZZPBKQFK-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(1-methyl-2-oxopiperidin-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=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1C(N(CCC1)C)=O KLPCGAZZPBKQFK-UHFFFAOYSA-N 0.000 claims 1
- NZINMIJFUZJCFM-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(3-methyloxolan-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=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1(COCC1)C NZINMIJFUZJCFM-UHFFFAOYSA-N 0.000 claims 1
- SCHXGVNXSKUUPT-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(6-morpholin-4-ylpyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound C1(=C(N=C(C(C=2OC=CN=2)=N1)C=1C=CC2=NC=C(N2C=1)C)C(=O)NCC1=NC(N2CCOCC2)=CC=C1)N SCHXGVNXSKUUPT-UHFFFAOYSA-N 0.000 claims 1
- OZKCIZVTQUKURF-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[2-[methyl(pyridin-2-yl)amino]ethyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCN(C1=NC=CC=C1)C OZKCIZVTQUKURF-UHFFFAOYSA-N 0.000 claims 1
- UIAHFQVANMNIST-LJQANCHMSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-5-phenylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=CC=C1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1N(CCC1)C UIAHFQVANMNIST-LJQANCHMSA-N 0.000 claims 1
- JXHMNRFYJVXUCF-CYBMUJFWSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(3R)-oxolan-3-yl]methyl]-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1COCC1 JXHMNRFYJVXUCF-CYBMUJFWSA-N 0.000 claims 1
- RCYBPJLFLQYBBK-UHFFFAOYSA-N 3-amino-6-[3-(aminomethyl)imidazo[1,2-a]pyridin-6-yl]-N-[(3-fluoropyridin-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=1C=CC=2N(C=1)C(=CN=2)CN)C(=O)NCC1=NC=CC=C1F RCYBPJLFLQYBBK-UHFFFAOYSA-N 0.000 claims 1
- XVMZHBKBLNKXOK-UHFFFAOYSA-N 3-amino-6-imidazo[1,2-a]pyridin-6-yl-N-[(2-methyl-1,3-thiazol-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=1C=CC=2N(C=1)C=CN=2)C(=O)NCC=1N=C(SC=1)C XVMZHBKBLNKXOK-UHFFFAOYSA-N 0.000 claims 1
- PWTLVPKJUUTVFY-UHFFFAOYSA-N 3-amino-6-imidazo[1,2-a]pyridin-6-yl-N-[[6-(methylamino)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=1C=CC=2N(C=1)C=CN=2)C(=O)NCC1=NC(=CC=C1)NC PWTLVPKJUUTVFY-UHFFFAOYSA-N 0.000 claims 1
- QNMVJSJIKXTZKO-UHFFFAOYSA-N 3-amino-N-(1,4-dioxan-2-ylmethyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound O1C(COCC1)CNC(=O)C1=NC(=C(N=C1N)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C QNMVJSJIKXTZKO-UHFFFAOYSA-N 0.000 claims 1
- RBQLYYUZQQMZJT-UHFFFAOYSA-N 3-amino-N-(1-bicyclo[1.1.1]pentanyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC12CC(C1)C2 RBQLYYUZQQMZJT-UHFFFAOYSA-N 0.000 claims 1
- JXDCOYUAQRJKFV-UHFFFAOYSA-N 3-amino-N-(2-cyanoethyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCC#N JXDCOYUAQRJKFV-UHFFFAOYSA-N 0.000 claims 1
- IAFLBSRGRKIYEQ-UHFFFAOYSA-N 3-amino-N-(2-methoxyethyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCOC IAFLBSRGRKIYEQ-UHFFFAOYSA-N 0.000 claims 1
- YZBAXKURIQDESW-UHFFFAOYSA-N 3-amino-N-(2-methoxyethyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCOC YZBAXKURIQDESW-UHFFFAOYSA-N 0.000 claims 1
- RRBCLOPZSBAVSY-UHFFFAOYSA-N 3-amino-N-(3-methoxypropyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCCOC RRBCLOPZSBAVSY-UHFFFAOYSA-N 0.000 claims 1
- ZKUUVQJXALMKKI-UHFFFAOYSA-N 3-amino-N-(3-methoxypropyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCCOC ZKUUVQJXALMKKI-UHFFFAOYSA-N 0.000 claims 1
- WNKPXZYITJFTTJ-UHFFFAOYSA-N 3-amino-N-(4-methoxycyclohexyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC1CCC(CC1)OC WNKPXZYITJFTTJ-UHFFFAOYSA-N 0.000 claims 1
- KMJQYHHNZZRHGL-UHFFFAOYSA-N 3-amino-N-(cyclopropylmethyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1CC1 KMJQYHHNZZRHGL-UHFFFAOYSA-N 0.000 claims 1
- PEBQXJRBPDHWPV-UHFFFAOYSA-N 3-amino-N-[(1-methylpyrrolidin-2-yl)methyl]-5-(1,3-oxazol-2-yl)-6-[3-(trifluoromethyl)imidazo[1,2-a]pyridin-6-yl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C(F)(F)F)C(=O)NCC1N(CCC1)C PEBQXJRBPDHWPV-UHFFFAOYSA-N 0.000 claims 1
- QTGNUFYPMKDXSV-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-5-(1,3-oxazol-2-yl)-6-(6-oxo-1H-pyridin-3-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CNC(C=C1)=O)C(=O)NCC1=C(C=CC=C1F)F QTGNUFYPMKDXSV-UHFFFAOYSA-N 0.000 claims 1
- BEFFDNOKNRRUKO-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-5-(1,3-oxazol-2-yl)-6-([1,2,4]triazolo[4,3-a]pyridin-6-yl)pyrazine-2-carboxamide Chemical compound N=1N=CN2C=1C=CC(=C2)C1=C(N=C(C(=N1)C(=O)NCC1=C(C=CC=C1F)F)N)C=1OC=CN=1 BEFFDNOKNRRUKO-UHFFFAOYSA-N 0.000 claims 1
- FCCDPOFDYGHKNW-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-5-(4-fluorophenyl)-6-[1-(oxetan-3-yl)-6-oxopyridin-3-yl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C1COC1)C(=O)NCC1=C(C=CC=C1F)F FCCDPOFDYGHKNW-UHFFFAOYSA-N 0.000 claims 1
- RBMAZAAFROWNEL-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-morpholin-4-ylpyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1CCOCC1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1=C(C=CC=C1F)F RBMAZAAFROWNEL-UHFFFAOYSA-N 0.000 claims 1
- HHSKAMLYLMLZDG-UHFFFAOYSA-N 3-amino-N-[(2-dimethylphosphoryl-6-fluorophenyl)methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1F)P(=O)(C)C HHSKAMLYLMLZDG-UHFFFAOYSA-N 0.000 claims 1
- IPLKTNLGNGVUGJ-LLVKDONJSA-N 3-amino-N-[(2R)-1-methoxypropan-2-yl]-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)N[C@@H](COC)C IPLKTNLGNGVUGJ-LLVKDONJSA-N 0.000 claims 1
- RYAPSWUNGQZYBS-GFCCVEGCSA-N 3-amino-N-[(2R)-4-(dimethylamino)-4-oxobutan-2-yl]-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)N[C@@H](CC(=O)N(C)C)C RYAPSWUNGQZYBS-GFCCVEGCSA-N 0.000 claims 1
- RYAPSWUNGQZYBS-LBPRGKRZSA-N 3-amino-N-[(2S)-4-(dimethylamino)-4-oxobutan-2-yl]-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)N[C@H](CC(=O)N(C)C)C RYAPSWUNGQZYBS-LBPRGKRZSA-N 0.000 claims 1
- MBDPUTNEWLDTNV-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-2-yl)methyl]-6-(3-methylbenzimidazol-5-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CC2=C(N=CN2C)C=C1)C(=O)NCC1=NC=CC=C1F MBDPUTNEWLDTNV-UHFFFAOYSA-N 0.000 claims 1
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- YTOKUPSVMWWKDE-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-2-yl)methyl]-6-imidazo[1,2-a]pyridin-6-yl-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C=CN=2)C(=O)NCC1=NC=CC=C1F YTOKUPSVMWWKDE-UHFFFAOYSA-N 0.000 claims 1
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- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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| PCT/CN2019/100996 WO2020035052A1 (en) | 2018-08-17 | 2019-08-16 | Pyrazine compounds and uses thereof |
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| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| AU2019323035B2 (en) * | 2018-08-17 | 2024-11-07 | Dizal (Jiangsu) Pharmaceutical Co., Ltd. | Pyrazine compounds and uses thereof |
| JP2022517418A (ja) * | 2019-01-18 | 2022-03-08 | ニューベイション・バイオ・インコーポレイテッド | アデノシンアンタゴニストとしてのヘテロ環式化合物 |
| EP3911323A4 (en) * | 2019-01-18 | 2022-11-16 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| EP3911324A4 (en) | 2019-01-18 | 2022-08-17 | Nuvation Bio Inc. | 1,8-NAPHTHYRIDINONE COMPOUNDS AND THEIR USES |
| WO2021146629A1 (en) * | 2020-01-17 | 2021-07-22 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| WO2021146631A1 (en) * | 2020-01-17 | 2021-07-22 | Nuvation Bio Inc. | Heterocyclic compounds as adenosine antagonists |
| CA3182410A1 (en) | 2020-05-04 | 2021-11-11 | Volastra Therapeutics, Inc. | Imino sulfanone inhibitors of enpp1 |
| US12091412B2 (en) | 2020-06-16 | 2024-09-17 | Volastra Therapeutics, Inc. | Heterocyclic inhibitors of ENPP1 |
| KR102621694B1 (ko) * | 2022-09-15 | 2024-01-08 | 주식회사 스탠다임 | 아데노신 a2a 수용체 길항제 및 이의 용도 |
| US11987581B1 (en) | 2023-12-19 | 2024-05-21 | King Faisal University | Imidazo[1,2-c]pyrido[3,4-e]pyrimidine-2-carboxylic acids as CK2 inhibitors |
| US11964974B1 (en) | 2024-01-08 | 2024-04-23 | King Faisal University | Imidazo[1,2-c]pyrido[3,4-e]pyrimidine-3-carboxylic acids as CK2 inhibitors |
| WO2025191185A1 (en) * | 2024-03-15 | 2025-09-18 | Domain Therapeutics | Azine-based compounds as par-2 inhibitors and therapeutic uses thereof |
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| JP2007510620A (ja) | 2003-10-27 | 2007-04-26 | アステラス製薬株式会社 | ピラジン誘導体およびその医薬的使用 |
| JP2007530434A (ja) | 2004-04-01 | 2007-11-01 | アステラス製薬株式会社 | ピラジン誘導体およびその医薬的使用 |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
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| CN1871231A (zh) * | 2003-10-27 | 2006-11-29 | 安斯泰来制药有限公司 | 吡嗪衍生物及其医药用途 |
| AU2019323035B2 (en) * | 2018-08-17 | 2024-11-07 | Dizal (Jiangsu) Pharmaceutical Co., Ltd. | Pyrazine compounds and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007510620A (ja) | 2003-10-27 | 2007-04-26 | アステラス製薬株式会社 | ピラジン誘導体およびその医薬的使用 |
| JP2007530434A (ja) | 2004-04-01 | 2007-11-01 | アステラス製薬株式会社 | ピラジン誘導体およびその医薬的使用 |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
Non-Patent Citations (1)
| Title |
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| Arzneimittel-Forschung,1996年,Vol.46, No.6,pp.643-648 |
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| US11571420B2 (en) | 2023-02-07 |
| WO2020035052A1 (en) | 2020-02-20 |
| KR20210046714A (ko) | 2021-04-28 |
| US10898481B2 (en) | 2021-01-26 |
| US20210251989A1 (en) | 2021-08-19 |
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| MX2024003385A (es) | 2024-04-05 |
| AR115985A1 (es) | 2021-03-17 |
| US20200330458A1 (en) | 2020-10-22 |
| US20230135068A1 (en) | 2023-05-04 |
| CN112055709A (zh) | 2020-12-08 |
| KR102816365B1 (ko) | 2025-06-02 |
| TW202023559A (zh) | 2020-07-01 |
| EP3837250A1 (en) | 2021-06-23 |
| BR112021002895A2 (pt) | 2021-05-11 |
| CA3107365A1 (en) | 2020-02-20 |
| MX2021001884A (es) | 2021-04-19 |
| EP3837250A4 (en) | 2022-06-29 |
| JP2021533179A (ja) | 2021-12-02 |
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