PT2300455T - Sais de 2-fluoro-n-metil-4-[7-(quinolin-6-il-metil)-imidazo[1,2-b][1,2,4]triazin-2-il] benzamida e processos relacionados com a sua preparação - Google Patents

Info

Publication number

PT2300455T

PT2300455T PT97514392T PT09751439T PT2300455T PT 2300455 T PT2300455 T PT 2300455T PT 97514392 T PT97514392 T PT 97514392T PT 09751439 T PT09751439 T PT 09751439T PT 2300455 T PT2300455 T PT 2300455T

Authority

PT

Portugal

Prior art keywords

compound

formula

salt

cancer

reaction

Prior art date

2008-05-21

Links

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• 238000000034 method Methods 0.000 title claims description 102
• 230000008569 process Effects 0.000 title claims description 62
• LIOLIMKSCNQPLV-UHFFFAOYSA-N 2-fluoro-n-methyl-4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide Chemical class C1=C(F)C(C(=O)NC)=CC=C1C1=NN2C(CC=3C=C4C=CC=NC4=CC=3)=CN=C2N=C1 LIOLIMKSCNQPLV-UHFFFAOYSA-N 0.000 title claims description 23
• 150000001875 compounds Chemical class 0.000 claims description 163
• 239000000203 mixture Substances 0.000 claims description 100
• 238000006243 chemical reaction Methods 0.000 claims description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 66
• 239000002253 acid Substances 0.000 claims description 52
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 51
• 239000002904 solvent Substances 0.000 claims description 41
• 238000002360 preparation method Methods 0.000 claims description 40
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 36
• -1 quinolin-6-ylmethyl Chemical group 0.000 claims description 36
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• 239000002585 base Substances 0.000 claims description 29
• FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo(3.3.1)nonane Chemical compound C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 claims description 24
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
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• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
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• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 10
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• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
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• 125000002346 iodo group Chemical group I* 0.000 claims description 9
• MJIWQHRXSLOUJN-UHFFFAOYSA-N 1,2,4-triazin-3-amine Chemical compound NC1=NC=CN=N1 MJIWQHRXSLOUJN-UHFFFAOYSA-N 0.000 claims description 8
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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