BE509974A - - Google Patents

Info

Publication number

BE509974A

BE509974A BE509974DA BE509974A BE 509974 A BE509974 A BE 509974A BE 509974D A BE509974D A BE 509974DA BE 509974 A BE509974 A BE 509974A

Authority

BE

Belgium

Prior art keywords

parts

oxo

weight

thiosemicarbazone

volume

Prior art date

Links

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• SRVJKTDHMYAMHA-WUXMJOGZSA-N Thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 claims description 12
• 229940042396 direct acting antivirals Thiosemicarbazones Drugs 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 150000003584 thiosemicarbazones Chemical class 0.000 claims description 5
• PRNSUJCXOCSNAQ-UHFFFAOYSA-N (3,4-dihydro-2H-naphthalen-1-ylideneamino)thiourea Chemical compound C1=CC=C2C(=NNC(=S)N)CCCC2=C1 PRNSUJCXOCSNAQ-UHFFFAOYSA-N 0.000 claims 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• BRWIZMBXBAOCCF-UHFFFAOYSA-N aminothiourea Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 239000000155 melt Substances 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 125000002723 alicyclic group Chemical group 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 150000001875 compounds Chemical class 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000000203 mixture Substances 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 150000003583 thiosemicarbazides Chemical class 0.000 description 5
• 229960000583 Acetic Acid Drugs 0.000 description 4
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• PVTHIYCCXJJALA-UHFFFAOYSA-M [S-]C#N.NN Chemical compound [S-]C#N.NN PVTHIYCCXJJALA-UHFFFAOYSA-M 0.000 description 3
• 238000002360 preparation method Methods 0.000 description 3
• -1 thiosemicarbazide Chemical class 0.000 description 3
• OTYBMLCTZGSZBG-UHFFFAOYSA-L Potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• 235000019439 ethyl acetate Nutrition 0.000 description 2
• 239000012362 glacial acetic acid Substances 0.000 description 2
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• WFHFUKVEUQNVSI-UHFFFAOYSA-N (2,3-dihydroinden-1-ylideneamino)thiourea Chemical compound C1=CC=C2C(=NNC(=S)N)CCC2=C1 WFHFUKVEUQNVSI-UHFFFAOYSA-N 0.000 description 1
• XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-Tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
• SIUOTMYWHGODQX-UHFFFAOYSA-N 3-phenyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)CC1C1=CC=CC=C1 SIUOTMYWHGODQX-UHFFFAOYSA-N 0.000 description 1
• UOYIXKRJHGAFHE-UHFFFAOYSA-N NC(=S)NN=C1CC(C2=CC=CC=C12)C1=CC=CC=C1 Chemical compound NC(=S)NN=C1CC(C2=CC=CC=C12)C1=CC=CC=C1 UOYIXKRJHGAFHE-UHFFFAOYSA-N 0.000 description 1
• 210000003635 Pituitary Gland Anatomy 0.000 description 1
• ZNNZYHKDIALBAK-UHFFFAOYSA-M Potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 125000005466 alkylenyl group Chemical group 0.000 description 1
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 230000000875 corresponding Effects 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 230000002124 endocrine Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 150000002429 hydrazines Chemical class 0.000 description 1
• 150000002576 ketones Chemical group 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• 229910052939 potassium sulfate Inorganic materials 0.000 description 1
• 235000011151 potassium sulphates Nutrition 0.000 description 1
• 229940116357 potassium thiocyanate Drugs 0.000 description 1
• 150000007659 semicarbazones Chemical class 0.000 description 1
• HLFCZZKCHVSOAP-DAMYXMBDSA-M sodium;(5Z)-5-(carbamoylhydrazinylidene)-1-methyl-6-oxo-2,3-dihydroindole-2-sulfonate Chemical compound [Na+].NC(=O)N/N=C/1C(=O)C=C2N(C)C(S([O-])(=O)=O)CC2=C\1 HLFCZZKCHVSOAP-DAMYXMBDSA-M 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 230000001225 therapeutic Effects 0.000 description 1