NO317704B1 - Nye neuraminsyrederivater, anvendelse av disse til fremstilling av medikamenter for behandling eller forhindring av infeksjon i et pattedyt forarsaket av et sialidasebaerende virus og farmasoytiske preparater omfattende disse neuraminsyrederivatene. - Google Patents

Info

Publication number

NO317704B1

NO317704B1 NO19973363A NO973363A NO317704B1 NO 317704 B1 NO317704 B1 NO 317704B1 NO 19973363 A NO19973363 A NO 19973363A NO 973363 A NO973363 A NO 973363A NO 317704 B1 NO317704 B1 NO 317704B1

Authority

NO

Norway

Prior art keywords

denotes

group

reaction

acid

acetamido

Prior art date

1996-07-22

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• 241000700605 Viruses Species 0.000 title claims abstract description 23
• 102000005348 Neuraminidase Human genes 0.000 title claims abstract description 19
• 108010006232 Neuraminidase Proteins 0.000 title claims abstract description 19
• 239000002253 acid Substances 0.000 title claims description 84
• 208000015181 infectious disease Diseases 0.000 title claims description 12
• 241000124008 Mammalia Species 0.000 title claims description 5
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• 239000003814 drug Substances 0.000 title claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 355
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 17
• 238000011282 treatment Methods 0.000 claims abstract description 10
• 230000002265 prevention Effects 0.000 claims abstract description 9
• -1 decanoyl- Chemical group 0.000 claims description 406
• 125000004432 carbon atom Chemical group C* 0.000 claims description 86
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
• 150000002148 esters Chemical class 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 31
• 125000001931 aliphatic group Chemical group 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 16
• 125000001589 carboacyl group Chemical group 0.000 claims description 16
• 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 6
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 11
• 239000001257 hydrogen Substances 0.000 abstract description 11
• 229910052739 hydrogen Inorganic materials 0.000 abstract description 11
• 206010022000 influenza Diseases 0.000 abstract description 8
• 201000010099 disease Diseases 0.000 abstract description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
• 230000010076 replication Effects 0.000 abstract description 3
• 230000003612 virological effect Effects 0.000 abstract description 3
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
• 229910052736 halogen Inorganic materials 0.000 abstract description 2
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• 239000002911 sialidase inhibitor Substances 0.000 abstract description 2
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• 239000001301 oxygen Substances 0.000 abstract 1
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• 230000002829 reductive effect Effects 0.000 description 117
• 238000004821 distillation Methods 0.000 description 106
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
• 239000007864 aqueous solution Substances 0.000 description 100
• 238000000034 method Methods 0.000 description 97
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
• 235000017557 sodium bicarbonate Nutrition 0.000 description 41
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• 238000004809 thin layer chromatography Methods 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
• 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
• 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 239000012588 trypsin Substances 0.000 description 1
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229910052727 yttrium Inorganic materials 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1