DK2748171T3 - PYRANO [3,2-D] [1,3] THIAZOL AS GLYCOSIDASE INHIBITORS - Google Patents

Info

Publication number

DK2748171T3

DK2748171T3 DK12753341.2T DK12753341T DK2748171T3 DK 2748171 T3 DK2748171 T3 DK 2748171T3 DK 12753341 T DK12753341 T DK 12753341T DK 2748171 T3 DK2748171 T3 DK 2748171T3

Authority

DK

Denmark

Prior art keywords

compound

atoms

pyrano

tetrahydro

hal

Prior art date

2011-08-25

Links

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• 239000003316 glycosidase inhibitor Substances 0.000 title description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 296
• 150000003839 salts Chemical class 0.000 claims description 61
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• 239000004480 active ingredient Substances 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
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• 108010031186 Glycoside Hydrolases Proteins 0.000 claims description 26
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• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
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• 239000003814 drug Substances 0.000 claims description 16
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• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 230000004770 neurodegeneration Effects 0.000 claims description 13
• 230000001225 therapeutic effect Effects 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
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• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
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• 238000003818 flash chromatography Methods 0.000 description 15
• PPAIMZHKIXDJRN-FMDGEEDCSA-N (3ar,5r,6s,7r,7ar)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]2O PPAIMZHKIXDJRN-FMDGEEDCSA-N 0.000 description 14
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 210000004556 brain Anatomy 0.000 description 11
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• FWTQXVHJQOUABA-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-2-(ethylamino)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-5-carboxylic acid Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@@H]2O FWTQXVHJQOUABA-KYGLGHNPSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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• PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 8
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