TWI601727B - 三環雜環化合物及ｊａｋ（傑納斯激酶）抑制劑 - Google Patents
三環雜環化合物及ｊａｋ（傑納斯激酶）抑制劑 Download PDFInfo
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- TWI601727B TWI601727B TW101129126A TW101129126A TWI601727B TW I601727 B TWI601727 B TW I601727B TW 101129126 A TW101129126 A TW 101129126A TW 101129126 A TW101129126 A TW 101129126A TW I601727 B TWI601727 B TW I601727B
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- Prior art keywords
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- aromatic heterocyclic
- alkyl
- substituted
- membered
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- 108091000080 Phosphotransferase Proteins 0.000 title description 3
- 102000020233 phosphotransferase Human genes 0.000 title description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims description 852
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 633
- 125000005843 halogen group Chemical group 0.000 claims description 341
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 340
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 339
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 339
- 150000001875 compounds Chemical class 0.000 claims description 336
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 249
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 231
- 125000003118 aryl group Chemical group 0.000 claims description 228
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 219
- -1 C 1-6 halosulfonyl Chemical group 0.000 claims description 209
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 202
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- 150000003839 salts Chemical class 0.000 claims description 182
- 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims description 178
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 167
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 149
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 146
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 130
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 118
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 107
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 105
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 97
- 125000003277 amino group Chemical group 0.000 claims description 90
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 86
- 125000004122 cyclic group Chemical group 0.000 claims description 84
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 82
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 77
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 62
- 125000002723 alicyclic group Chemical group 0.000 claims description 58
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 56
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 53
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 51
- 229910052801 chlorine Inorganic materials 0.000 claims description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims description 51
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 50
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 229910052717 sulfur Inorganic materials 0.000 claims description 50
- 125000004434 sulfur atom Chemical group 0.000 claims description 50
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 47
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 46
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 44
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004429 atom Chemical group 0.000 claims description 37
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
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- CJYXNHVHUDVIKK-UHFFFAOYSA-N PCOS(=O)(=O)O Chemical compound PCOS(=O)(=O)O CJYXNHVHUDVIKK-UHFFFAOYSA-N 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
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- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005256 alkoxyacyl group Chemical group 0.000 claims 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 36
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 30
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- 239000002585 base Substances 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 14
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Classifications
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| JP2011177289 | 2011-08-12 | ||
| JP2011177270 | 2011-08-12 | ||
| JP2012097073 | 2012-04-20 | ||
| JP2012103516 | 2012-04-27 | ||
| JP2012103517 | 2012-04-27 |
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| TWI601727B true TWI601727B (zh) | 2017-10-11 |
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|---|---|---|---|---|
| US7960139B2 (en) | 2007-03-23 | 2011-06-14 | Academia Sinica | Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells |
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