TWI627173B - 作為ＮＩＫ抑制劑的新穎３－（１Ｈ－吡唑－４－基）－１Ｈ－吡咯并［２，３－ｃ］吡啶衍生物 - Google Patents

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Publication number

TWI627173B

TWI627173B TW103132895A TW103132895A TWI627173B TW I627173 B TWI627173 B TW I627173B TW 103132895 A TW103132895 A TW 103132895A TW 103132895 A TW103132895 A TW 103132895A TW I627173 B TWI627173 B TW I627173B

Authority

TW

Taiwan

Prior art keywords

alkyl

group

substituted

hydrogen

het

Prior art date

2013-09-26

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• 239000003112 inhibitor Substances 0.000 title abstract description 12
• BMZWBEHLBROZOP-UHFFFAOYSA-N c1n[nH]cc1-c1c[nH]c2cnccc12 Chemical class c1n[nH]cc1-c1c[nH]c2cnccc12 BMZWBEHLBROZOP-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 232
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• 125000000217 alkyl group Chemical group 0.000 claims description 619
• 239000001257 hydrogen Substances 0.000 claims description 275
• 229910052739 hydrogen Inorganic materials 0.000 claims description 275
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 246
• 125000001153 fluoro group Chemical group F* 0.000 claims description 152
• 125000001424 substituent group Chemical group 0.000 claims description 129
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 121
• 150000003839 salts Chemical class 0.000 claims description 111
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 65
• -1 iso Oxazolyl Chemical group 0.000 claims description 64
• 238000002360 preparation method Methods 0.000 claims description 62
• 229910052799 carbon Inorganic materials 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 60
• 125000003386 piperidinyl group Chemical group 0.000 claims description 53
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 229910052731 fluorine Inorganic materials 0.000 claims description 44
• 239000011737 fluorine Substances 0.000 claims description 44
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 42
• 125000002393 azetidinyl group Chemical group 0.000 claims description 39
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 39
• 125000003566 oxetanyl group Chemical group 0.000 claims description 36
• 125000000335 thiazolyl group Chemical group 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 26
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
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• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000002883 imidazolyl group Chemical group 0.000 claims description 16
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• 125000005843 halogen group Chemical group 0.000 claims description 14
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• 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
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• 125000001544 thienyl group Chemical group 0.000 claims description 13
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 230000002062 proliferating effect Effects 0.000 claims description 3
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• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
• 150000002431 hydrogen Chemical class 0.000 claims 3
• JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical group C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
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• 239000011734 sodium Substances 0.000 description 36
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 32
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 31
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• 239000012267 brine Substances 0.000 description 26
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• 238000006243 chemical reaction Methods 0.000 description 25
• 239000002585 base Substances 0.000 description 24
• 239000007858 starting material Substances 0.000 description 22
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 20
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
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