JPWO2020035052A5 - - Google Patents
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- Publication number
- JPWO2020035052A5 JPWO2020035052A5 JP2021507992A JP2021507992A JPWO2020035052A5 JP WO2020035052 A5 JPWO2020035052 A5 JP WO2020035052A5 JP 2021507992 A JP2021507992 A JP 2021507992A JP 2021507992 A JP2021507992 A JP 2021507992A JP WO2020035052 A5 JPWO2020035052 A5 JP WO2020035052A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- carboxamide
- pyrazine
- methyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 145
- -1 cyano, amino, carbamoyl Chemical group 0.000 claims 81
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 47
- 229920006395 saturated elastomer Polymers 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 38
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 36
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 34
- 125000004438 haloalkoxy group Chemical group 0.000 claims 32
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical group 0.000 claims 30
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 29
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 23
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 21
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 20
- 239000004202 carbamide Chemical group 0.000 claims 20
- 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 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 18
- 125000005236 alkanoylamino group Chemical group 0.000 claims 17
- 125000004452 carbocyclyl group Chemical group 0.000 claims 17
- 150000003857 carboxamides Chemical class 0.000 claims 15
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 7
- 229910019142 PO4 Inorganic materials 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000006001 difluoroethyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000003566 oxetanyl group Chemical group 0.000 claims 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 6
- 239000010452 phosphate Substances 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 102000009346 Adenosine receptors Human genes 0.000 claims 4
- 108050000203 Adenosine receptors Proteins 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 229940127089 cytotoxic agent Drugs 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000002955 immunomodulating agent Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- KRMSXKRAKMCMKK-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-(oxetan-2-ylmethyl)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)NCC1OCC1 KRMSXKRAKMCMKK-UHFFFAOYSA-N 0.000 claims 2
- OGTBKCORUXUJIZ-CQSZACIVSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2R)-oxolan-2-yl]methyl]-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1N1N=CC=N1)C=1C=CC2=NC=C(N2C=1)C)C(=O)NC[C@H]1CCCO1)N OGTBKCORUXUJIZ-CQSZACIVSA-N 0.000 claims 2
- OGTBKCORUXUJIZ-AWEZNQCLSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2S)-oxolan-2-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]1OCCC1 OGTBKCORUXUJIZ-AWEZNQCLSA-N 0.000 claims 2
- XMCUHVNKPMTPBL-UHFFFAOYSA-N 3-amino-N-(2-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)NCC(C)OC XMCUHVNKPMTPBL-UHFFFAOYSA-N 0.000 claims 2
- MSOLIVLGQNJTQC-UHFFFAOYSA-N 3-amino-N-[[6-(dimethylamino)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC(=O)N(C=1)C)C(=O)NCC1=NC(N(C)C)=CC=C1)N MSOLIVLGQNJTQC-UHFFFAOYSA-N 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- JJMSIYRSBIUVAN-UHFFFAOYSA-N NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC1COCCC1 Chemical class NC=1C(=NC(=C(N=1)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC1COCCC1 JJMSIYRSBIUVAN-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- 229960005305 adenosine Drugs 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 238000002648 combination therapy Methods 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- 208000019465 refractory cytopenia of childhood Diseases 0.000 claims 2
- 208000002491 severe combined immunodeficiency Diseases 0.000 claims 2
- JVBKMPOWMKESEQ-HXUWFJFHSA-N (2R)-N-[[3-amino-5-(3,4-difluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC(=C(C=C1)F)F)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@@H]1N(CCC1)C JVBKMPOWMKESEQ-HXUWFJFHSA-N 0.000 claims 1
- ISAOBZDUJJAYJY-HXUWFJFHSA-N (2R)-N-[[3-amino-5-(3,5-difluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC(=CC(=C1)F)F)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@@H]1N(CCC1)C ISAOBZDUJJAYJY-HXUWFJFHSA-N 0.000 claims 1
- UKEIGNNBXGVFNJ-HXUWFJFHSA-N (2R)-N-[[3-amino-5-(3-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC(=CC=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@@H]1N(CCC1)C UKEIGNNBXGVFNJ-HXUWFJFHSA-N 0.000 claims 1
- XXCHESCEBAKRTR-HXUWFJFHSA-N (2R)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@@H]1N(CCC1)C XXCHESCEBAKRTR-HXUWFJFHSA-N 0.000 claims 1
- PLKFRDMKHVPHAL-LJQANCHMSA-N (2R)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]oxolane-2-carboxamide Chemical compound O1[C@H](CCC1)C(=O)NCC1=NC(=C(N=C1N)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C PLKFRDMKHVPHAL-LJQANCHMSA-N 0.000 claims 1
- DOBQNEZAPIPMCJ-MRXNPFEDSA-N (2R)-N-[[3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(triazol-2-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@@H]1N(CCC1)C DOBQNEZAPIPMCJ-MRXNPFEDSA-N 0.000 claims 1
- XXCHESCEBAKRTR-FQEVSTJZSA-N (2S)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]-1-methylpyrrolidine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)CNC(=O)[C@H]1N(CCC1)C XXCHESCEBAKRTR-FQEVSTJZSA-N 0.000 claims 1
- PLKFRDMKHVPHAL-IBGZPJMESA-N (2S)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]oxolane-2-carboxamide Chemical compound O1[C@@H](CCC1)C(=O)NCC1=NC(=C(N=C1N)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C PLKFRDMKHVPHAL-IBGZPJMESA-N 0.000 claims 1
- VYPFULPDSRDGQB-QGZVFWFLSA-N (3R)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]oxolane-3-carboxamide Chemical compound O1C[C@@H](CC1)C(=O)NCC1=NC(=C(N=C1N)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C VYPFULPDSRDGQB-QGZVFWFLSA-N 0.000 claims 1
- VYPFULPDSRDGQB-KRWDZBQOSA-N (3S)-N-[[3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazin-2-yl]methyl]oxolane-3-carboxamide Chemical compound O1C[C@H](CC1)C(=O)NCC1=NC(=C(N=C1N)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C VYPFULPDSRDGQB-KRWDZBQOSA-N 0.000 claims 1
- YHPQBBMZOPTOCG-QGZVFWFLSA-N 3-amino-5-(3,4-difluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC(=C(C=C1)F)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1N(CCC1)C YHPQBBMZOPTOCG-QGZVFWFLSA-N 0.000 claims 1
- TXUHGXQWAXFCPM-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-(2-methylsulfonylethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCCS(=O)(=O)C TXUHGXQWAXFCPM-UHFFFAOYSA-N 0.000 claims 1
- MFZUGCVPENECRJ-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(1-methyl-2-oxopyrrolidin-3-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1C(N(CC1)C)=O MFZUGCVPENECRJ-UHFFFAOYSA-N 0.000 claims 1
- OFCZNIJHHVHDCZ-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(1-methylpyrrolidin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1N(CCC1)C OFCZNIJHHVHDCZ-UHFFFAOYSA-N 0.000 claims 1
- AZIJKWJHMGKZBE-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[(4-methylmorpholin-2-yl)methyl]pyrazine-2-carboxamide Chemical class NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1CN(CCO1)C AZIJKWJHMGKZBE-UHFFFAOYSA-N 0.000 claims 1
- OFCZNIJHHVHDCZ-LJQANCHMSA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@@H]1N(CCC1)C OFCZNIJHHVHDCZ-LJQANCHMSA-N 0.000 claims 1
- OFCZNIJHHVHDCZ-IBGZPJMESA-N 3-amino-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[(2S)-1-methylpyrrolidin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NC[C@H]1N(CCC1)C OFCZNIJHHVHDCZ-IBGZPJMESA-N 0.000 claims 1
- HVCKZFCNCJDADL-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-N-[(2-methoxyphenyl)methyl]-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 HVCKZFCNCJDADL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GMGHQEQUMOGLIH-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-N-[[3-(2-hydroxyethylamino)pyridin-2-yl]methyl]-6-(3-methylbenzimidazol-5-yl)pyrazine-2-carboxamide Chemical compound C(CO)NC1=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 GMGHQEQUMOGLIH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MTXDGSJBXJSKSA-UHFFFAOYSA-N 3-amino-5-(4-fluorophenyl)-N-[[3-[2-(methylamino)ethoxy]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)C1=CC2=C(N=CN2C)C=C1)C(=O)NCC1=NC=CC=C1OCCNC MTXDGSJBXJSKSA-UHFFFAOYSA-N 0.000 claims 1
- AMAUQHZTYZQDHE-UHFFFAOYSA-N 3-amino-6-(1,5-dimethyl-6-oxopyridin-3-yl)-5-(4-fluorophenyl)-N-[(2-methoxyphenyl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C(=C1)C)=O)C)C(=O)NCC1=C(C=CC=C1)OC AMAUQHZTYZQDHE-UHFFFAOYSA-N 0.000 claims 1
- RCVUUQWXZAMGJR-UHFFFAOYSA-N 3-amino-6-(1-ethyl-6-oxopyridin-3-yl)-5-(4-fluorophenyl)-N-[(2-methoxyphenyl)methyl]pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)CC)C(=O)NCC1=C(C=CC=C1)OC RCVUUQWXZAMGJR-UHFFFAOYSA-N 0.000 claims 1
- OQNNWINZKWOANA-UHFFFAOYSA-N 3-amino-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)-N-[(6-pyrrolidin-1-ylpyridin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound C(=O)(C1=C(N)N=C(C=2OC=CN=2)C(=N1)C=1C=CC(=O)N(C=1)C)NCC1=NC(=CC=C1)N1CCCC1 OQNNWINZKWOANA-UHFFFAOYSA-N 0.000 claims 1
- NLRNJLUEEQKFMF-UHFFFAOYSA-N 3-amino-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)-N-[[3-(trifluoromethoxy)pyridin-2-yl]methyl]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=C1OC(F)(F)F NLRNJLUEEQKFMF-UHFFFAOYSA-N 0.000 claims 1
- QCORNPGCYRKECH-UHFFFAOYSA-N 3-amino-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)-N-[[3-(trifluoromethyl)pyridin-2-yl]methyl]pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC(=O)N(C=1)C)C(=O)NCC1=NC=CC=C1C(F)(F)F)N QCORNPGCYRKECH-UHFFFAOYSA-N 0.000 claims 1
- ROVNSTSDJGUBCO-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)-N-[(2-methoxypyridin-3-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)NCC=1C(=NC=CC=1)OC ROVNSTSDJGUBCO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SZNKXJBJVFBSNP-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)-N-[(3-methoxypyridin-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=C1OC SZNKXJBJVFBSNP-UHFFFAOYSA-N 0.000 claims 1
- MVBUSACJHSHWPE-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-5-(4-fluorophenyl)-N-[[2-(trifluoromethoxy)phenyl]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=C(C=CC=C1)OC(F)(F)F MVBUSACJHSHWPE-UHFFFAOYSA-N 0.000 claims 1
- BJQRPWQCDUCEJU-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-N-[(2-methoxyphenyl)methyl]-5-(5-methylfuran-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC(=CC=1)C)C1=CC(=NC(=C1)C)C)C(=O)NCC1=C(C=CC=C1)OC BJQRPWQCDUCEJU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AKBDLOJYXXSSQM-UHFFFAOYSA-N 3-amino-6-(2,6-dimethylpyridin-4-yl)-N-[(3-fluoro-2-methoxyphenyl)methyl]-5-(4-fluorophenyl)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=C(C(=CC=C1)F)OC AKBDLOJYXXSSQM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FVJJRIWIGUAJDB-MRXNPFEDSA-N 3-amino-6-(3-ethylpyrazolo[1,5-a]pyridin-5-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CC=2N(C=C1)N=CC=2CC)C(=O)NC[C@@H]1N(CCC1)C FVJJRIWIGUAJDB-MRXNPFEDSA-N 0.000 claims 1
- FVJJRIWIGUAJDB-INIZCTEOSA-N 3-amino-6-(3-ethylpyrazolo[1,5-a]pyridin-5-yl)-N-[[(2S)-1-methylpyrrolidin-2-yl]methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C=1OC=CN=1)C1=CC=2N(C=C1)N=CC=2CC)C(=O)NC[C@H]1N(CCC1)C FVJJRIWIGUAJDB-INIZCTEOSA-N 0.000 claims 1
- JKXFHDCTZCCMDP-UHFFFAOYSA-N 3-amino-6-(3-methylbenzimidazol-5-yl)-N-[(1-methylpyrrolidin-2-yl)methyl]-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C1=CC2=C(N=CN2C)C=C1)C(=O)NCC1N(CCC1)C JKXFHDCTZCCMDP-UHFFFAOYSA-N 0.000 claims 1
- JKXFHDCTZCCMDP-CQSZACIVSA-N 3-amino-6-(3-methylbenzimidazol-5-yl)-N-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC2=C(N(C=N2)C)C=1)C(=O)NC[C@@H]1N(CCC1)C JKXFHDCTZCCMDP-CQSZACIVSA-N 0.000 claims 1
- JKXFHDCTZCCMDP-AWEZNQCLSA-N 3-amino-6-(3-methylbenzimidazol-5-yl)-N-[[(2S)-1-methylpyrrolidin-2-yl]methyl]-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C=1C=CC2=C(N(C=N2)C)C=1)C(=O)NC[C@H]1N(CCC1)C JKXFHDCTZCCMDP-AWEZNQCLSA-N 0.000 claims 1
- AOKBFUQQHLNDQG-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[(1,4,4-trimethylpyrrolidin-2-yl)methyl]pyrazine-2-carboxamide Chemical compound C1(N)=NC(C=2OC=CN=2)=C(N=C1C(=O)NCC1N(CC(C)(C)C1)C)C=1C=CC2=NC=C(N2C=1)C AOKBFUQQHLNDQG-UHFFFAOYSA-N 0.000 claims 1
- SHLOOCOOTGHYSD-LBPRGKRZSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[(2S)-1-(triazol-2-yl)propan-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](CN1N=CC=N1)C SHLOOCOOTGHYSD-LBPRGKRZSA-N 0.000 claims 1
- LTAUMGCPIWCWDZ-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-5-(1,3-oxazol-2-yl)-N-[1-(1,2,4-triazol-1-yl)propan-2-yl]pyrazine-2-carboxamide Chemical compound N1(N=CN=C1)CC(C)NC(=O)C1=NC(=C(N=C1N)C=1OC=CN=1)C=1C=CC=2N(C=1)C(=CN=2)C LTAUMGCPIWCWDZ-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- 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
- 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
- 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
- XJBCWCOZPROJGF-UHFFFAOYSA-N 3-amino-6-(3-methylimidazo[1,2-a]pyridin-6-yl)-N-[[6-(4-methylpiperazin-1-yl)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)C(=O)NCC1=NC(=CC=C1)N1CCN(CC1)C XJBCWCOZPROJGF-UHFFFAOYSA-N 0.000 claims 1
- GYCBAWUOCFEMQV-UHFFFAOYSA-N 3-amino-6-(3H-benzimidazol-5-yl)-N-[(3-fluoropyridin-2-yl)methyl]-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C1=CC=C2NC=NC2=C1)C(=O)NCC1=C(C=CC=N1)F)N GYCBAWUOCFEMQV-UHFFFAOYSA-N 0.000 claims 1
- MWOVDYRYZUZQTD-UHFFFAOYSA-N 3-amino-6-[1-(difluoromethyl)-6-oxopyridin-3-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)C1=CN(C(C=C1)=O)C(F)F)C(=O)NCC1=NC=CC=C1F MWOVDYRYZUZQTD-UHFFFAOYSA-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
- DVHUVOWCVIABLZ-UHFFFAOYSA-N 3-amino-6-imidazo[1,2-a]pyridin-6-yl-5-(1,3-oxazol-2-yl)-N-(1,3-thiazol-4-ylmethyl)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=1 DVHUVOWCVIABLZ-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
- 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
- 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
- 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
- WMTYEJRWAPGQDY-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)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=C1F)F WMTYEJRWAPGQDY-UHFFFAOYSA-N 0.000 claims 1
- UYISQIQFMVKYFR-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(triazol-2-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=CC=N1)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1F)F UYISQIQFMVKYFR-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
- ZOQZGBIHGZGDEI-UHFFFAOYSA-N 3-amino-N-[(2,6-difluorophenyl)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=C(C=CC=C1F)F ZOQZGBIHGZGDEI-UHFFFAOYSA-N 0.000 claims 1
- ZRQWEBZDUXQEGN-UHFFFAOYSA-N 3-amino-N-[(2-fluoro-6-morpholin-4-ylphenyl)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=C1N1CCOCC1)F ZRQWEBZDUXQEGN-UHFFFAOYSA-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
- DCKGSAAFEJDERC-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-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=C1F DCKGSAAFEJDERC-UHFFFAOYSA-N 0.000 claims 1
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- BEYZUKZRZOPCPC-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-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=C1F BEYZUKZRZOPCPC-UHFFFAOYSA-N 0.000 claims 1
- SKOGBDVYSCHLTE-UHFFFAOYSA-N 3-amino-N-[(3-fluoropyridin-2-yl)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=NC=CC=C1F SKOGBDVYSCHLTE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CBXYJZBCLYHQEG-UHFFFAOYSA-N 3-amino-N-[(6-amino-3-fluoropyridin-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=C1F)N CBXYJZBCLYHQEG-UHFFFAOYSA-N 0.000 claims 1
- XBKMJZVUSIRMKX-UHFFFAOYSA-N 3-amino-N-[(6-aminopyridin-2-yl)methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC(=O)N(C=1)C)C(=O)NCC1=NC(N)=CC=C1)N XBKMJZVUSIRMKX-UHFFFAOYSA-N 0.000 claims 1
- XZPSXDLKFYWCCO-UHFFFAOYSA-N 3-amino-N-[2-(difluoromethoxy)phenyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(3-methylpyrazol-1-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)N1N=C(C=C1)C)C1=CN(C(C=C1)=O)C)C(=O)NC1=C(C=CC=C1)OC(F)F XZPSXDLKFYWCCO-UHFFFAOYSA-N 0.000 claims 1
- VWSDUVNQRRRDHR-UHFFFAOYSA-N 3-amino-N-[2-(dimethylamino)ethyl]-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)NCCN(C)C VWSDUVNQRRRDHR-UHFFFAOYSA-N 0.000 claims 1
- GKPLSULXQVCGMO-UHFFFAOYSA-N 3-amino-N-[3-(dimethylamino)-2,2-dimethyl-3-oxopropyl]-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)NCC(C(=O)N(C)C)(C)C GKPLSULXQVCGMO-UHFFFAOYSA-N 0.000 claims 1
- FXZCFXBQCNZPBS-UHFFFAOYSA-N 3-amino-N-[[1-(dimethylamino)cyclopropyl]methyl]-5-(4-fluorophenyl)-6-(3-methylimidazo[1,2-a]pyridin-6-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C=1C=CC=2N(C=1)C(=CN=2)C)C(=O)NCC1(CC1)N(C)C FXZCFXBQCNZPBS-UHFFFAOYSA-N 0.000 claims 1
- XOHOLZCXFDPBFD-UHFFFAOYSA-N 3-amino-N-[[2-(difluoromethoxy)phenyl]methyl]-5-(4-fluorophenyl)-6-(1-methyl-6-oxopyridin-3-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CN(C(C=C1)=O)C)C(=O)NCC1=C(C=CC=C1)OC(F)F XOHOLZCXFDPBFD-UHFFFAOYSA-N 0.000 claims 1
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- BIGLAQCSBXBYBW-UHFFFAOYSA-N 3-amino-N-[[3-(2-hydroxyethoxy)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=C1OCCO BIGLAQCSBXBYBW-UHFFFAOYSA-N 0.000 claims 1
- HCTTUDFYPMZNPO-UHFFFAOYSA-N 3-amino-N-[[3-(difluoromethoxy)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=C1OC(F)F HCTTUDFYPMZNPO-UHFFFAOYSA-N 0.000 claims 1
- LDXKAFQHUIODAY-UHFFFAOYSA-N 3-amino-N-[[3-(difluoromethoxy)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound FC(OC1=C(CNC(=O)C2=C(N=C(C=3OC=CN=3)C(=N2)C=2C=CC(=O)N(C=2)C)N)N=CC=C1)F LDXKAFQHUIODAY-UHFFFAOYSA-N 0.000 claims 1
- CBZBLTQMVWBHON-UHFFFAOYSA-N 3-amino-N-[[3-(hydroxymethyl)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=C1CO CBZBLTQMVWBHON-UHFFFAOYSA-N 0.000 claims 1
- KUFTWLGWGQOREU-UHFFFAOYSA-N 3-amino-N-[[3-(methylamino)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N(C)C1=C(CNC(=O)C2=C(N=C(C=3OC=CN=3)C(=N2)C=2C=CC(=O)N(C=2)C)N)N=CC=C1 KUFTWLGWGQOREU-UHFFFAOYSA-N 0.000 claims 1
- QSYZHDBEZHGBCZ-UHFFFAOYSA-N 3-amino-N-[[3-[2-(dimethylamino)ethoxy]pyridin-2-yl]methyl]-5-(4-fluorophenyl)-6-(3-methylbenzimidazol-5-yl)pyrazine-2-carboxamide Chemical compound N(C)(CCOC1=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)C QSYZHDBEZHGBCZ-UHFFFAOYSA-N 0.000 claims 1
- ZTWUJHVMOHOEEK-UHFFFAOYSA-N 3-amino-N-[[3-[2-(methylamino)ethoxy]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=C1OCCNC ZTWUJHVMOHOEEK-UHFFFAOYSA-N 0.000 claims 1
- CCTFAARPXFZYAE-UHFFFAOYSA-N 3-amino-N-[[3-fluoro-6-(methylamino)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=C1F)NC CCTFAARPXFZYAE-UHFFFAOYSA-N 0.000 claims 1
- ILTFWXSKIIUDPC-UHFFFAOYSA-N 3-amino-N-[[4-(dimethylamino)pyrimidin-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(=N1)N(C)C ILTFWXSKIIUDPC-UHFFFAOYSA-N 0.000 claims 1
- QTIKZJCSSDLEDJ-UHFFFAOYSA-N 3-amino-N-[[6-(6-methyl-2,6-diazaspiro[3.3]heptan-2-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 N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC2=NC=C(N2C=1)C)C(=O)NCC1=NC(=CC=C1)N1CC2(CN(C2)C)C1)N QTIKZJCSSDLEDJ-UHFFFAOYSA-N 0.000 claims 1
- QHQNZDGPZZIMIH-UHFFFAOYSA-N 3-amino-N-[[6-(azetidin-1-yl)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound C1(=NC(C=2OC=CN=2)=C(N=C1C(=O)NCC1=NC(=CC=C1)N1CCC1)C=1C=CC(=O)N(C=1)C)N QHQNZDGPZZIMIH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GCZQCTXNLBCQCT-UHFFFAOYSA-N 3-amino-N-[[6-(dimethylamino)pyridin-2-yl]methyl]-5-(4-fluorophenyl)-6-(2-methylpyridin-4-yl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=C(N=1)C1=CC=C(C=C1)F)C1=CC(=NC=C1)C)C(=O)NCC1=NC(=CC=C1)N(C)C GCZQCTXNLBCQCT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PKBQAGFSMGQXRV-UHFFFAOYSA-N 3-amino-N-[[6-(methylamino)pyridin-2-yl]methyl]-6-(1-methyl-6-oxopyridin-3-yl)-5-(1,3-oxazol-2-yl)pyrazine-2-carboxamide Chemical compound N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC(=O)N(C=1)C)C(=O)NCC1=NC(=CC=C1)NC)N PKBQAGFSMGQXRV-UHFFFAOYSA-N 0.000 claims 1
- XHPYUWAINPXSSC-GOSISDBHSA-N 3-amino-N-[[6-[(3R)-3,4-dimethylpiperazin-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)N1C[C@H](N(CC1)C)C XHPYUWAINPXSSC-GOSISDBHSA-N 0.000 claims 1
- XHPYUWAINPXSSC-SFHVURJKSA-N 3-amino-N-[[6-[(3S)-3,4-dimethylpiperazin-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)N1C[C@@H](N(CC1)C)C XHPYUWAINPXSSC-SFHVURJKSA-N 0.000 claims 1
- 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 1
- MQVWUSOLTKTGGC-UHFFFAOYSA-N 3-amino-N-[[6-[3-(dimethylamino)pyrrolidin-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 N1=C(C(=NC(=C1C=1OC=CN=1)C=1C=CC2=NC=C(N2C=1)C)C(=O)NCC1=NC(N2CCC(N(C)C)C2)=CC=C1)N MQVWUSOLTKTGGC-UHFFFAOYSA-N 0.000 claims 1
- MHSORTVANMDQLE-UHFFFAOYSA-N 3-amino-N-[[6-[3-(methylamino)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)NC MHSORTVANMDQLE-UHFFFAOYSA-N 0.000 claims 1
- XQHUZMRFSAIXDB-UHFFFAOYSA-N 3-amino-N-[[6-[3-[(dimethylamino)methyl]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 C(=O)(C1=C(N)N=C(C=2OC=CN=2)C(=N1)C=1C=CC2=NC=C(N2C=1)C)NCC1=NC(=CC=C1)N1CC(CN(C)C)C1 XQHUZMRFSAIXDB-UHFFFAOYSA-N 0.000 claims 1
- ZSNIRQZLDALICH-UHFFFAOYSA-N 3-amino-N-cyclobutyl-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)NC1CCC1 ZSNIRQZLDALICH-UHFFFAOYSA-N 0.000 claims 1
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- 229960005420 etoposide Drugs 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
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- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
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| 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 |
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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 |
| CN1938296A (zh) * | 2004-04-01 | 2007-03-28 | 安斯泰来制药有限公司 | 作为腺苷拮抗剂的吡嗪衍生物及其制药用途 |
| WO2019018584A1 (en) * | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
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