TWI585088B - 作爲激酶抑制劑之咪唑并［１，２－ｂ］嗒衍生物 - Google Patents

Info

Publication number

TWI585088B

TWI585088B TW102119261A TW102119261A TWI585088B TW I585088 B TWI585088 B TW I585088B TW 102119261 A TW102119261 A TW 102119261A TW 102119261 A TW102119261 A TW 102119261A TW I585088 B TWI585088 B TW I585088B

Authority

TW

Taiwan

Prior art keywords

group

compound

cancer

phenyl

imidazo

Prior art date

2012-06-04

Links

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• 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
• 150000002475 indoles Chemical class 0.000 title 1
• 229940043355 kinase inhibitor Drugs 0.000 title 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 437
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 238
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 138
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 119
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 119
• 150000003839 salts Chemical class 0.000 claims description 78
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 65
• 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 claims description 63
• 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 claims description 63
• 108090000623 proteins and genes Proteins 0.000 claims description 56
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 51
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
• 230000002401 inhibitory effect Effects 0.000 claims description 32
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 31
• 125000003277 amino group Chemical group 0.000 claims description 31
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 230000004927 fusion Effects 0.000 claims description 30
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
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• 239000004480 active ingredient Substances 0.000 claims description 24
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
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• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 18
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• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
• 208000007766 Kaposi sarcoma Diseases 0.000 claims description 5
• 208000021780 appendiceal neoplasm Diseases 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 208000029742 colonic neoplasm Diseases 0.000 claims description 5
• 230000001747 exhibiting effect Effects 0.000 claims description 5
• 201000007270 liver cancer Diseases 0.000 claims description 5
• 208000014018 liver neoplasm Diseases 0.000 claims description 5
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
• 206010014733 Endometrial cancer Diseases 0.000 claims description 4
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
• 206010052399 Neuroendocrine tumour Diseases 0.000 claims description 4
• 208000016065 neuroendocrine neoplasm Diseases 0.000 claims description 4
• 201000011519 neuroendocrine tumor Diseases 0.000 claims description 4
• LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims description 3
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
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• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 1
• 125000003545 alkoxy group Chemical group 0.000 claims 1
• 230000029087 digestion Effects 0.000 claims 1
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 1
• 230000002440 hepatic effect Effects 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 256
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