BE502127A - - Google Patents
Info
- Publication number
- BE502127A BE502127A BE502127DA BE502127A BE 502127 A BE502127 A BE 502127A BE 502127D A BE502127D A BE 502127DA BE 502127 A BE502127 A BE 502127A
- Authority
- BE
- Belgium
- Prior art keywords
- thiosemicarbazone
- solution
- water
- benzalacetone
- melting
- Prior art date
Links
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 claims description 7
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 7
- 150000003584 thiosemicarbazones Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical class CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 aldehyde thiosemicarbazones Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- AIVYBZNYDAYFOK-UHFFFAOYSA-N (4-phenylbut-3-en-2-ylideneamino)thiourea Chemical compound NC(=S)NN=C(C)C=CC1=CC=CC=C1 AIVYBZNYDAYFOK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- GBQNOTBHFNICRZ-UHFFFAOYSA-N [4-[3-(carbamothioylhydrazinylidene)but-1-enyl]phenyl] acetate Chemical compound C(C)(=O)OC1=CC=C(C=CC(C)=NNC(=S)N)C=C1 GBQNOTBHFNICRZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- RTEPFWZHFCWRAG-UHFFFAOYSA-N 4-(4-aminophenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(N)C=C1 RTEPFWZHFCWRAG-UHFFFAOYSA-N 0.000 description 1
- IAMOQOMGCKCSEJ-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]but-3-en-2-one Chemical compound CN(C)C1=CC=C(C=CC(C)=O)C=C1 IAMOQOMGCKCSEJ-UHFFFAOYSA-N 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- OSVLCQWOKSQZFT-UHFFFAOYSA-N N(C(=O)C)C1=CC=C(C=CC(C)=NNC(=S)N)C=C1 Chemical compound N(C(=O)C)C1=CC=C(C=CC(C)=NNC(=S)N)C=C1 OSVLCQWOKSQZFT-UHFFFAOYSA-N 0.000 description 1
- BEBRJELOLRLITI-UHFFFAOYSA-N NC1=CC=C(C=CC(C)=NNC(=S)N)C=C1 Chemical compound NC1=CC=C(C=CC(C)=NNC(=S)N)C=C1 BEBRJELOLRLITI-UHFFFAOYSA-N 0.000 description 1
- COWAKOZXZREIGT-UHFFFAOYSA-N [4-(4-chlorophenyl)but-3-en-2-ylideneamino]thiourea Chemical compound NC(=S)NN=C(C)C=CC1=CC=C(Cl)C=C1 COWAKOZXZREIGT-UHFFFAOYSA-N 0.000 description 1
- YHKFYJFYVGMSOK-UHFFFAOYSA-N [4-(4-nitrophenyl)but-3-en-2-ylideneamino]thiourea Chemical compound [N+](=O)([O-])C1=CC=C(C=CC(C)=NNC(=S)N)C=C1 YHKFYJFYVGMSOK-UHFFFAOYSA-N 0.000 description 1
- NWKAPIHJDZDGMQ-UHFFFAOYSA-N [4-[4-(dimethylamino)phenyl]but-3-en-2-ylideneamino]thiourea Chemical compound CN(C)C1=CC=C(C=CC(C)=NNC(N)=S)C=C1 NWKAPIHJDZDGMQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AMXOFEWEPYFRPN-UHFFFAOYSA-N n-[4-(3-oxobut-1-enyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C=CC(C)=O)C=C1 AMXOFEWEPYFRPN-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE502127A true BE502127A (enrdf_load_stackoverflow) |
Family
ID=143734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE502127D BE502127A (enrdf_load_stackoverflow) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE502127A (enrdf_load_stackoverflow) |
-
0
- BE BE502127D patent/BE502127A/fr unknown
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