BE503014A - - Google Patents

Info

Publication number

BE503014A

BE503014A BE503014DA BE503014A BE 503014 A BE503014 A BE 503014A BE 503014D A BE503014D A BE 503014DA BE 503014 A BE503014 A BE 503014A

Authority

BE

Belgium

Prior art keywords

phthalaldehyde

thiosemicarbazide

solution

mol

production

Prior art date

Links

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• BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 10
• ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 claims description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
• 239000002904 solvent Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 claims description 3
• 238000001953 recrystallisation Methods 0.000 claims description 3
• 150000003584 thiosemicarbazones Chemical class 0.000 claims description 3
• 238000003756 stirring Methods 0.000 claims description 2
• 239000002253 acid Substances 0.000 claims 1
• 125000003172 aldehyde group Chemical group 0.000 claims 1
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims 1
• 238000009835 boiling Methods 0.000 claims 1
• 238000009827 uniform distribution Methods 0.000 claims 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 150000001875 compounds Chemical class 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 235000011121 sodium hydroxide Nutrition 0.000 description 4
• 239000007795 chemical reaction product Substances 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 239000000047 product Substances 0.000 description 3
• WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 2
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
• 229960000583 acetic acid Drugs 0.000 description 2
• 229960004909 aminosalicylic acid Drugs 0.000 description 2
• IZALUMVGBVKPJD-UHFFFAOYSA-N benzene-1,3-dicarbaldehyde Chemical compound O=CC1=CC=CC(C=O)=C1 IZALUMVGBVKPJD-UHFFFAOYSA-N 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• 239000012535 impurity Substances 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 241001474791 Proboscis Species 0.000 description 1
• ATTFZKKNUFOHRF-UHFFFAOYSA-N [(4-formylphenyl)methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=C(C=O)C=C1 ATTFZKKNUFOHRF-UHFFFAOYSA-N 0.000 description 1
• VTZWNSAFVYMODF-ACFHMISVSA-N [(e)-[4-[(e)-(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)N\N=C\C1=CC=C(\C=N\NC(N)=S)C=C1 VTZWNSAFVYMODF-ACFHMISVSA-N 0.000 description 1
• SYDDDECKVFWDCK-UHFFFAOYSA-N [[2-[(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=CC=C1C=NNC(N)=S SYDDDECKVFWDCK-UHFFFAOYSA-N 0.000 description 1
• BPBGBZSSUXXWPS-UHFFFAOYSA-N [[3-[(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea Chemical compound NC(=S)NN=CC1=CC=CC(C=NNC(N)=S)=C1 BPBGBZSSUXXWPS-UHFFFAOYSA-N 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000007859 condensation product Substances 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 229940054441 o-phthalaldehyde Drugs 0.000 description 1
• 230000037452 priming Effects 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1