TW202328129A - 治療自體免疫疾病之吡唑并［３，４—ｂ］吡啶化合物 - Google Patents

Info

Publication number

TW202328129A

TW202328129A TW111136043A TW111136043A TW202328129A TW 202328129 A TW202328129 A TW 202328129A TW 111136043 A TW111136043 A TW 111136043A TW 111136043 A TW111136043 A TW 111136043A TW 202328129 A TW202328129 A TW 202328129A

Authority

TW

Taiwan

Prior art keywords

methyl

compound

piperidinyl

pyridine

pyridyl

Prior art date

2021-09-24

Links

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• 238000011282 treatment Methods 0.000 title description 14
• 208000023275 Autoimmune disease Diseases 0.000 title description 5
• 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 298
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• 238000000034 method Methods 0.000 claims abstract description 20
• -1 3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazinyl Chemical group 0.000 claims description 164
• 238000002360 preparation method Methods 0.000 claims description 70
• 125000000217 alkyl group Chemical group 0.000 claims description 66
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• 125000003545 alkoxy group Chemical group 0.000 claims description 31
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• 108010060818 Toll-Like Receptor 9 Proteins 0.000 claims description 30
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
• 101000800483 Homo sapiens Toll-like receptor 8 Proteins 0.000 claims description 24
• 102100033110 Toll-like receptor 8 Human genes 0.000 claims description 22
• 238000006243 chemical reaction Methods 0.000 claims description 20
• 125000004193 piperazinyl group Chemical group 0.000 claims description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 18
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
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• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims description 14
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
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• MXFYYFVVIIWKFE-UHFFFAOYSA-N dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane Chemical group CC(C)OC1=CC=CC(OC(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 MXFYYFVVIIWKFE-UHFFFAOYSA-N 0.000 claims description 10
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