CN106573931A - 抑制BET蛋白的具有间位取代的芳族氨基或醚基的3，4‑二氢吡啶并[2，3‑b]吡嗪酮 - Google Patents

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Publication number

CN106573931A

CN106573931A CN201580044412.8A CN201580044412A CN106573931A CN 106573931 A CN106573931 A CN 106573931A CN 201580044412 A CN201580044412 A CN 201580044412A CN 106573931 A CN106573931 A CN 106573931A

Authority

CN

China

Prior art keywords

alkyl

phenyl

methyl

unsubstituted

pyrazine

Prior art date

2014-06-18

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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• 230000002401 inhibitory effect Effects 0.000 title abstract description 5
• HIGOCZJARKJCGG-UHFFFAOYSA-N 3,4-dihydro-1h-pyrido[2,3-b]pyrazin-2-one Chemical class C1=CC=C2NC(=O)CNC2=N1 HIGOCZJARKJCGG-UHFFFAOYSA-N 0.000 title abstract 2
• 125000001033 ether group Chemical group 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 336
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• 201000010099 disease Diseases 0.000 claims abstract description 52
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• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 6
• -1 phenyl- Chemical group 0.000 claims description 456
• BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 122
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
• 125000001424 substituent group Chemical group 0.000 claims description 104
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 100
• 229910052739 hydrogen Inorganic materials 0.000 claims description 98
• 239000001257 hydrogen Substances 0.000 claims description 98
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 97
• 125000000623 heterocyclic group Chemical group 0.000 claims description 95
• 239000011737 fluorine Substances 0.000 claims description 88
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• 239000000460 chlorine Chemical group 0.000 claims description 79
• 229910052801 chlorine Inorganic materials 0.000 claims description 78
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 77
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 51
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 38
• 239000003814 drug Substances 0.000 claims description 36
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 33
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical group 0.000 claims description 31
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
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• 150000001721 carbon Chemical group 0.000 claims description 23
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 22
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 15
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• DCBOUXKSNFDXER-UHFFFAOYSA-N 1h-pyrido[2,3-b]pyrazin-2-one Chemical compound C1=CC=C2NC(=O)C=NC2=N1 DCBOUXKSNFDXER-UHFFFAOYSA-N 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 3
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• 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims description 2
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• YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
• 150000003673 urethanes Chemical class 0.000 claims description 2
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