KR101962495B1 - C-kit 키나제 억제제로서의 화합물 및 조성물 - Google Patents
C-kit 키나제 억제제로서의 화합물 및 조성물 Download PDFInfo
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- KR101962495B1 KR101962495B1 KR1020147008107A KR20147008107A KR101962495B1 KR 101962495 B1 KR101962495 B1 KR 101962495B1 KR 1020147008107 A KR1020147008107 A KR 1020147008107A KR 20147008107 A KR20147008107 A KR 20147008107A KR 101962495 B1 KR101962495 B1 KR 101962495B1
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- KR
- South Korea
- Prior art keywords
- pyridine
- imidazo
- oxadiazol
- methylphenyl
- carboxamide
- Prior art date
- 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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- 150000001875 compounds Chemical class 0.000 title claims abstract description 330
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- 238000000034 method Methods 0.000 claims abstract description 59
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 443
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 262
- 125000005842 heteroatom Chemical group 0.000 claims description 231
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- 239000011570 nicotinamide Substances 0.000 claims description 222
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 199
- 229910052760 oxygen Inorganic materials 0.000 claims description 139
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 130
- 229910052717 sulfur Inorganic materials 0.000 claims description 130
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 128
- 150000003839 salts Chemical class 0.000 claims description 111
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- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 82
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 81
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- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 51
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- ZMBYQTGAXZOMOO-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carboxamide Chemical compound C1=CC=CN2C(C(=O)N)=CN=C21 ZMBYQTGAXZOMOO-UHFFFAOYSA-N 0.000 claims description 40
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 15
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- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims description 7
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- YTKRQWIFWWXEFE-UHFFFAOYSA-N 2-[5-[5-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]-1,2,4-oxadiazol-3-yl]-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide Chemical compound OC1(CN(C1)C1=NC(=NO1)C=1C=CC(=C(C1)C=1N=C2N(C=C(C=C2)C)C1C(=O)N)C)C(F)(F)F YTKRQWIFWWXEFE-UHFFFAOYSA-N 0.000 claims description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 4
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- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
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- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 4
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- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
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Landscapes
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| US201161530038P | 2011-09-01 | 2011-09-01 | |
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| PCT/US2012/052802 WO2013033167A1 (en) | 2011-09-01 | 2012-08-29 | Compounds and compositions as c-kit kinase inhibitors |
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| KR20140075692A KR20140075692A (ko) | 2014-06-19 |
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| KR1020147008107A Active KR101962495B1 (ko) | 2011-09-01 | 2012-08-29 | C-kit 키나제 억제제로서의 화합물 및 조성물 |
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