TW201024313A - Derivatives of 1-amino-2-cyclobutylethylboronic acid - Google Patents

Info

Publication number

TW201024313A

TW201024313A TW098133005A TW98133005A TW201024313A TW 201024313 A TW201024313 A TW 201024313A TW 098133005 A TW098133005 A TW 098133005A TW 98133005 A TW98133005 A TW 98133005A TW 201024313 A TW201024313 A TW 201024313A

Authority

TW

Taiwan

Prior art keywords

group

substituted

unsubstituted

alkyl

independently

Prior art date

2008-09-29

Links

• Espacenet
• Global Dossier
• Discuss

• BCNMPHGGRXUKHU-UHFFFAOYSA-N (1-amino-2-cyclobutylethyl)boronic acid Chemical class OB(O)C(N)CC1CCC1 BCNMPHGGRXUKHU-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 238000011282 treatment Methods 0.000 claims abstract description 8
• 125000003118 aryl group Chemical group 0.000 claims description 82
• -1 benzo-salt Chemical group 0.000 claims description 78
• 239000002253 acid Substances 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 64
• 125000001931 aliphatic group Chemical group 0.000 claims description 63
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 31
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 125000002950 monocyclic group Chemical group 0.000 claims description 17
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
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• 125000006162 fluoroaliphatic group Chemical group 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 150000008064 anhydrides Chemical class 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
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• DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 2
• IYLGZMTXKJYONK-ACLXAEORSA-N (12s,15r)-15-hydroxy-11,16-dioxo-15,20-dihydrosenecionan-12-yl acetate Chemical compound O1C(=O)[C@](CC)(O)C[C@@H](C)[C@](C)(OC(C)=O)C(=O)OCC2=CCN3[C@H]2[C@H]1CC3 IYLGZMTXKJYONK-ACLXAEORSA-N 0.000 claims 1
• BGDOLELXXPTPFX-UHFFFAOYSA-N 3,4-dihydro-2h-1,2-benzoxazine Chemical compound C1=CC=C2ONCCC2=C1 BGDOLELXXPTPFX-UHFFFAOYSA-N 0.000 claims 1
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
• 241000605059 Bacteroidetes Species 0.000 claims 1
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• XIYZMOFCMDIBKI-UHFFFAOYSA-N Isolin Natural products CCC1C(OC(=O)C)C(C)C(C)(O)C(=O)OCC2=CCN3CCC(OC1=O)C23 XIYZMOFCMDIBKI-UHFFFAOYSA-N 0.000 claims 1
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 66
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
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