BE517234A - - Google Patents
Info
- Publication number
- BE517234A BE517234A BE517234DA BE517234A BE 517234 A BE517234 A BE 517234A BE 517234D A BE517234D A BE 517234DA BE 517234 A BE517234 A BE 517234A
- Authority
- BE
- Belgium
- Prior art keywords
- phenyl
- para
- carbon atoms
- group
- substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- 230000001034 aminogenic Effects 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003585 thioureas Chemical class 0.000 claims description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- MWKFDFSVYXECSU-UHFFFAOYSA-N (4-butoxyphenyl)thiourea Chemical compound CCCCOC1=CC=C(NC(N)=S)C=C1 MWKFDFSVYXECSU-UHFFFAOYSA-N 0.000 claims 1
- JYCBKPOKWDDOOV-UHFFFAOYSA-N 1-(4-butoxyphenyl)-3-[4-(dimethylamino)phenyl]thiourea Chemical compound C1=CC(OCCCC)=CC=C1NC(=S)NC1=CC=C(N(C)C)C=C1 JYCBKPOKWDDOOV-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 238000009835 boiling Methods 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- -1 1,3-bis-substituted thiourea Chemical class 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- ZWZVWGITAAIFPS-UHFFFAOYSA-N Thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 5
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N [N-]=C=S Chemical compound [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QKFJKGMPGYROCL-UHFFFAOYSA-N Phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGLYTNIXHPCRCF-UHFFFAOYSA-N (4-ethoxyphenyl)thiourea Chemical compound CCOC1=CC=C(NC(N)=S)C=C1 QGLYTNIXHPCRCF-UHFFFAOYSA-N 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N 1-[(1S,2R,3R,4S,5R,6R)-3-carbamimidamido-6-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,4,5-trihydroxycyclohexyl]guanidine Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical group CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- UUZDAMLMGSTKHI-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3-(4-piperidin-1-ylphenyl)thiourea Chemical compound C1=CC(OCC)=CC=C1NC(=S)NC1=CC=C(N2CCCCC2)C=C1 UUZDAMLMGSTKHI-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-Aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N Butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- HIUXRFFANDWDFA-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NC(=S)NC1=CC=C(C=C1)OCCC)C Chemical compound CN(C1=CC=C(C=C1)NC(=S)NC1=CC=C(C=C1)OCCC)C HIUXRFFANDWDFA-UHFFFAOYSA-N 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N Ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 231100000601 Intoxication Toxicity 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 229940010383 Mycobacterium tuberculosis Drugs 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N N-Propyl iodide Chemical group CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N Phenylisocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 229960005322 Streptomycin Drugs 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940121383 antituberculosis agents Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940042396 direct acting antivirals Thiosemicarbazones Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- SUSXWKRWORPGPG-UHFFFAOYSA-N phenylcarbamodithioic acid Chemical compound SC(=S)NC1=CC=CC=C1 SUSXWKRWORPGPG-UHFFFAOYSA-N 0.000 description 1
- BMBJSXKEXRFGAV-UHFFFAOYSA-N phenylcarbamothioic S-acid Chemical compound SC(=O)NC1=CC=CC=C1 BMBJSXKEXRFGAV-UHFFFAOYSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE517234A true BE517234A (es) |
Family
ID=154195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE517234D BE517234A (es) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE517234A (es) |
-
0
- BE BE517234D patent/BE517234A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH375017A (fr) | Procédé de préparation de nouveaux dérivés de l'imidazole | |
| EP0376850B1 (fr) | Dérivés du benzène, leur préparation et compositions pharmaceutiques les contenant | |
| EP0348257A2 (fr) | Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique | |
| CA1053679A (fr) | N-(trifluoromethyl-3-phenyl)-1-propyl-2 glycinate de aminoalkyle | |
| CH407088A (fr) | Procédé de préparation de dérivés des acides 4-halo-3-sulfamoyl-benzoïques | |
| BE517234A (es) | ||
| CA1211105A (fr) | Procede pour la preparation de derives de p-acylaminophenol et derives obtenus par ce procede | |
| CA1253153A (fr) | Derives d'(arylpiperazinylethylaminoethoxy)-4 phenol, leur methode de preparation et leur application therapeutique | |
| BE884977A (fr) | Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes | |
| CA1161444A (fr) | Procede de preparation de derives du cycloheptindolol et de leurs sels avec les acides | |
| BE667262A (es) | ||
| CH641764A5 (fr) | Sels d'imidoesters et procede de synthese de 2-naphtalene-ethanimidamide n,n'-disubstitues a partir desdits sels. | |
| BE517290A (es) | ||
| BE623104A (es) | ||
| FR2584722A1 (fr) | Nouveaux amides substitues, leur preparation et les medicaments qui les contiennent | |
| BE721781A (es) | ||
| BE519639A (es) | ||
| BE466711A (es) | ||
| CH346221A (fr) | Procédé de préparation de dérivés de la pipérazine | |
| BE533436A (es) | ||
| CH383972A (fr) | Procédé de préparation de phényloxyméthyl-2-oxazolidinones | |
| CH420107A (fr) | Procédé de préparation de nouveaux dérivés d'aralcoylaminoalcoylcyclohexanes substitués | |
| BE485826A (es) | ||
| BE664212A (es) | ||
| CH356134A (fr) | Procédé de préparation de composés thérapeutiques |