TWI831738B - 用於抑制ＲＯＲγ及其他用途的嘧啶三環烯酮衍生物 - Google Patents

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Publication number

TWI831738B

TWI831738B TW106144248A TW106144248A TWI831738B TW I831738 B TWI831738 B TW I831738B TW 106144248 A TW106144248 A TW 106144248A TW 106144248 A TW106144248 A TW 106144248A TW I831738 B TWI831738 B TW I831738B

Authority

TW

Taiwan

Prior art keywords

substituted

group

compound

room temperature

alkyl

Prior art date

2016-12-16

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• 108091008773 RAR-related orphan receptors γ Proteins 0.000 title abstract description 3
• 230000005764 inhibitory process Effects 0.000 title description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 204
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 210
• 125000003118 aryl group Chemical group 0.000 claims description 186
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 143
• 229910052739 hydrogen Inorganic materials 0.000 claims description 137
• 239000001257 hydrogen Substances 0.000 claims description 123
• -1 4-(2-cyclopropyl)-pyridyl Chemical group 0.000 claims description 108
• 125000003545 alkoxy group Chemical group 0.000 claims description 73
• 229910052799 carbon Inorganic materials 0.000 claims description 70
• 125000004432 carbon atom Chemical group C* 0.000 claims description 53
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
• 201000010099 disease Diseases 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 42
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 41
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 39
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 37
• 229910052760 oxygen Inorganic materials 0.000 claims description 34
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 29
• 125000003107 substituted aryl group Chemical group 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000003277 amino group Chemical group 0.000 claims description 20
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
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• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
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• 150000002390 heteroarenes Chemical class 0.000 claims description 3
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• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
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• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
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• 206010028417 myasthenia gravis Diseases 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 208000020016 psychiatric disease Diseases 0.000 claims description 2
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
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• 238000000034 method Methods 0.000 abstract description 128
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 594
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• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 252
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 194
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• 125000000217 alkyl group Chemical group 0.000 description 187
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