KR102457840B1 - 보론산 유도체 - Google Patents

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Publication number

KR102457840B1

KR102457840B1 KR1020177011562A KR20177011562A KR102457840B1 KR 102457840 B1 KR102457840 B1 KR 102457840B1 KR 1020177011562 A KR1020177011562 A KR 1020177011562A KR 20177011562 A KR20177011562 A KR 20177011562A KR 102457840 B1 KR102457840 B1 KR 102457840B1

Authority

KR

South Korea

Prior art keywords

amino

ethyl

boronic acid

acetyl

prop

Prior art date

2014-10-01

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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• 150000001642 boronic acid derivatives Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 419
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 101001136986 Homo sapiens Proteasome subunit beta type-8 Proteins 0.000 claims abstract description 14
• 102100035760 Proteasome subunit beta type-8 Human genes 0.000 claims abstract description 14
• 201000005787 hematologic cancer Diseases 0.000 claims abstract description 8
• -1 monocyclic hydrocarbon Chemical class 0.000 claims description 412
• 150000003839 salts Chemical class 0.000 claims description 99
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
• 239000004480 active ingredient Substances 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 39
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 238000006467 substitution reaction Methods 0.000 claims description 29
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 26
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 25
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 23
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 21
• 125000004434 sulfur atom Chemical group 0.000 claims description 21
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 20
• 125000004122 cyclic group Chemical group 0.000 claims description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
• 229930195733 hydrocarbon Natural products 0.000 claims description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 17
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 17
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• 239000004215 Carbon black (E152) Substances 0.000 claims description 16
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
• 150000001408 amides Chemical class 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 10
• 230000002519 immonomodulatory effect Effects 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 239000004305 biphenyl Substances 0.000 claims description 9
• 235000010290 biphenyl Nutrition 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 229940124530 sulfonamide Drugs 0.000 claims description 9
• 150000003456 sulfonamides Chemical class 0.000 claims description 9
• 125000005620 boronic acid group Chemical group 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 150000002430 hydrocarbons Chemical class 0.000 claims description 6
• 125000002950 monocyclic group Chemical group 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 208000010159 IgA glomerulonephritis Diseases 0.000 claims description 5
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 235000012054 meals Nutrition 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
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