TW202227431A - 可做為tlr9抑制劑之經取代雜芳基化合物 - Google Patents

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Publication number

TW202227431A

TW202227431A TW110130426A TW110130426A TW202227431A TW 202227431 A TW202227431 A TW 202227431A TW 110130426 A TW110130426 A TW 110130426A TW 110130426 A TW110130426 A TW 110130426A TW 202227431 A TW202227431 A TW 202227431A

Authority

TW

Taiwan

Prior art keywords

phenyl

methyl

pyrrolo

pyridine

alkyl

Prior art date

2020-08-19

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• 239000003112 inhibitor Substances 0.000 title abstract description 28
• 125000001072 heteroaryl group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 261
• 150000003839 salts Chemical class 0.000 claims abstract description 79
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
• -1 6-azabicyclo[3.2.1]octyl Chemical group 0.000 claims description 159
• 239000012453 solvate Substances 0.000 claims description 83
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 80
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 50
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 48
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 39
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 36
• 239000003814 drug Substances 0.000 claims description 36
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 29
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• 125000003386 piperidinyl group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 239000003937 drug carrier Substances 0.000 claims description 17
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• 125000001424 substituent group Chemical group 0.000 claims description 15
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• 230000004761 fibrosis Effects 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 12
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
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• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 11
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 6
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• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
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• 229910052794 bromium Inorganic materials 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 4
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• ALQSTULDKGFVCG-ZVBBVAIHSA-N 1-methyl-6-[1-[(1S,5R)-8-(2-methylpropyl)-8-azabicyclo[3.2.1]octan-3-yl]piperidin-4-yl]-2-(4-methylsulfonylphenyl)pyrrolo[3,2-b]pyridine Chemical compound CC(C)CN([C@H](CC1)C2)[C@@H]1CC2N(CC1)CCC1C1=CN=C(C=C(C(C=C2)=CC=C2S(C)(=O)=O)N2C)C2=C1 ALQSTULDKGFVCG-ZVBBVAIHSA-N 0.000 claims 2
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