BE578408A - - Google Patents
Info
- Publication number
- BE578408A BE578408A BE578408DA BE578408A BE 578408 A BE578408 A BE 578408A BE 578408D A BE578408D A BE 578408DA BE 578408 A BE578408 A BE 578408A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- phenyl
- dichloroacet
- methylamido
- denotes
- Prior art date
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 42
- 238000002360 preparation method Methods 0.000 claims description 37
- -1 nitro, amino Chemical group 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 24
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- YYHDAWBGVZLMAD-UHFFFAOYSA-N phenyl furan-2-carboxylate Chemical compound C=1C=COC=1C(=O)OC1=CC=CC=C1 YYHDAWBGVZLMAD-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Carbodicyclohexylimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000005325 aryloxy aryl group Chemical group 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-Aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 208000004881 Amebiasis Diseases 0.000 claims description 5
- 206010001980 Amoebiasis Diseases 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical group COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- UHILTTPUZKFXCS-UHFFFAOYSA-N O1C=C(C=C1)C(=O)OC1=CC=CC=C1 Chemical compound O1C=C(C=C1)C(=O)OC1=CC=CC=C1 UHILTTPUZKFXCS-UHFFFAOYSA-N 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical group OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical group CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- NBFNGRDFKUJVIN-VAWYXSNFSA-N phenyl (E)-3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OC1=CC=CC=C1 NBFNGRDFKUJVIN-VAWYXSNFSA-N 0.000 claims description 3
- RLVLSYCCQCQIDE-UHFFFAOYSA-N phenyl 4-methylsulfonylbenzoate Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)OC1=CC=CC=C1 RLVLSYCCQCQIDE-UHFFFAOYSA-N 0.000 claims description 3
- LUSSRKMAXZEBEC-UHFFFAOYSA-N phenyl 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)OC1=CC=CC=C1 LUSSRKMAXZEBEC-UHFFFAOYSA-N 0.000 claims description 3
- XRVQTYPOPTUZRF-UHFFFAOYSA-M phenyl sulfite Chemical compound [O-]S(=O)OC1=CC=CC=C1 XRVQTYPOPTUZRF-UHFFFAOYSA-M 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- YIANBFBRKBLOMZ-UHFFFAOYSA-M C1(=CC=C(C=C1)OCC(=O)OC1=CC=CC=C1)OCC(=O)[O-] Chemical compound C1(=CC=C(C=C1)OCC(=O)OC1=CC=CC=C1)OCC(=O)[O-] YIANBFBRKBLOMZ-UHFFFAOYSA-M 0.000 claims description 2
- 229920000084 Gum arabic Polymers 0.000 claims description 2
- FFACSENHYLWWQR-UHFFFAOYSA-N O1C(CCC1)C(=O)OC1=CC=CC=C1 Chemical compound O1C(CCC1)C(=O)OC1=CC=CC=C1 FFACSENHYLWWQR-UHFFFAOYSA-N 0.000 claims description 2
- 229940049964 Oleate Drugs 0.000 claims description 2
- KDVYYBCNLVOHNI-UHFFFAOYSA-M [O-]C(=O)CCCCCCCCC(=O)Oc1ccccc1 Chemical compound [O-]C(=O)CCCCCCCCC(=O)Oc1ccccc1 KDVYYBCNLVOHNI-UHFFFAOYSA-M 0.000 claims description 2
- 239000000205 acacia gum Substances 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- YKWNDAOEJQMLGH-UHFFFAOYSA-N phenyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)OC1=CC=CC=C1 YKWNDAOEJQMLGH-UHFFFAOYSA-N 0.000 claims description 2
- JUUYZCCKKAMCFI-UHFFFAOYSA-N phenyl 2-(2-chlorophenoxy)acetate Chemical compound ClC1=CC=CC=C1OCC(=O)OC1=CC=CC=C1 JUUYZCCKKAMCFI-UHFFFAOYSA-N 0.000 claims description 2
- IJLGQUIBQKAWLW-UHFFFAOYSA-N phenyl 2-(3-chlorophenoxy)acetate Chemical compound ClC1=CC=CC(OCC(=O)OC=2C=CC=CC=2)=C1 IJLGQUIBQKAWLW-UHFFFAOYSA-N 0.000 claims description 2
- ZDSHUODJHDXTNI-UHFFFAOYSA-N phenyl 2-(4-methylphenoxy)acetate Chemical compound C1=CC(C)=CC=C1OCC(=O)OC1=CC=CC=C1 ZDSHUODJHDXTNI-UHFFFAOYSA-N 0.000 claims description 2
- QERSPBWYFVWQLY-UHFFFAOYSA-N phenyl 2-benzoylbenzoate Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 QERSPBWYFVWQLY-UHFFFAOYSA-N 0.000 claims description 2
- RBKABBZAJGDBFA-UHFFFAOYSA-N phenyl 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OC1=CC=CC=C1 RBKABBZAJGDBFA-UHFFFAOYSA-N 0.000 claims description 2
- HETDSEQVGCUOJR-UHFFFAOYSA-N phenyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC1=CC=CC=C1 HETDSEQVGCUOJR-UHFFFAOYSA-N 0.000 claims description 2
- WIDYZOXBOLTJJB-UHFFFAOYSA-N phenyl 2-oxo-2-phenylacetate Chemical compound C=1C=CC=CC=1C(=O)C(=O)OC1=CC=CC=C1 WIDYZOXBOLTJJB-UHFFFAOYSA-N 0.000 claims description 2
- PJANUNZPZUHMPM-UHFFFAOYSA-N phenyl 2-phenoxyacetate Chemical compound C=1C=CC=CC=1OC(=O)COC1=CC=CC=C1 PJANUNZPZUHMPM-UHFFFAOYSA-N 0.000 claims description 2
- KDIILCSPFULFPX-UHFFFAOYSA-N phenyl 2-phenoxybenzoate Chemical compound C=1C=CC=C(OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 KDIILCSPFULFPX-UHFFFAOYSA-N 0.000 claims description 2
- DPXSFDIOGXVWPF-UHFFFAOYSA-N phenyl 3-bromobenzoate Chemical compound BrC1=CC=CC(C(=O)OC=2C=CC=CC=2)=C1 DPXSFDIOGXVWPF-UHFFFAOYSA-N 0.000 claims description 2
- ZAUTUSIGKHWTSX-UHFFFAOYSA-N phenyl 3-methoxybenzoate Chemical compound COC1=CC=CC(C(=O)OC=2C=CC=CC=2)=C1 ZAUTUSIGKHWTSX-UHFFFAOYSA-N 0.000 claims description 2
- VIGODTIMSIHKSD-UHFFFAOYSA-N phenyl 3-phenylpropanoate Chemical compound C=1C=CC=CC=1OC(=O)CCC1=CC=CC=C1 VIGODTIMSIHKSD-UHFFFAOYSA-N 0.000 claims description 2
- WOHDXQQIBRMRFA-UHFFFAOYSA-N phenyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC=CC=C1 WOHDXQQIBRMRFA-UHFFFAOYSA-N 0.000 claims description 2
- QEUUMMVGDPCNNF-UHFFFAOYSA-N phenyl 5-nitrofuran-2-carboxylate Chemical compound O1C([N+](=O)[O-])=CC=C1C(=O)OC1=CC=CC=C1 QEUUMMVGDPCNNF-UHFFFAOYSA-N 0.000 claims description 2
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 claims description 2
- NHASTOMELKHZLY-UHFFFAOYSA-N phenyl cyclopentanecarboxylate Chemical compound C1CCCC1C(=O)OC1=CC=CC=C1 NHASTOMELKHZLY-UHFFFAOYSA-N 0.000 claims description 2
- MNTZZDOKIWMNIM-UHFFFAOYSA-N phenyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OC1=CC=CC=C1 MNTZZDOKIWMNIM-UHFFFAOYSA-N 0.000 claims description 2
- ZPORCTAUIXXZAI-UHFFFAOYSA-N phenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=CC=CC=C1 ZPORCTAUIXXZAI-UHFFFAOYSA-N 0.000 claims description 2
- SOOXQKVMQBCEGW-UHFFFAOYSA-N phenyl hexanoate Chemical compound CCCCCC(=O)OC1=CC=CC=C1 SOOXQKVMQBCEGW-UHFFFAOYSA-N 0.000 claims description 2
- NUMNZKICGJJSHN-UHFFFAOYSA-N phenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC=CC=C1 NUMNZKICGJJSHN-UHFFFAOYSA-N 0.000 claims description 2
- ZBZSVGXZAPNCSY-UHFFFAOYSA-N phenyl octanoate Chemical compound CCCCCCCC(=O)OC1=CC=CC=C1 ZBZSVGXZAPNCSY-UHFFFAOYSA-N 0.000 claims description 2
- KELVZEPBVDRQNR-UHFFFAOYSA-N phenyl pyrazine-2-carboxylate Chemical compound C=1N=CC=NC=1C(=O)OC1=CC=CC=C1 KELVZEPBVDRQNR-UHFFFAOYSA-N 0.000 claims description 2
- RGQQGHGIUCRECH-UHFFFAOYSA-N phenyl pyridine-4-carboxylate Chemical compound C=1C=NC=CC=1C(=O)OC1=CC=CC=C1 RGQQGHGIUCRECH-UHFFFAOYSA-N 0.000 claims description 2
- SVPGUDRYMNIGFO-UHFFFAOYSA-N phenyl quinoline-2-carboxylate Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)OC1=CC=CC=C1 SVPGUDRYMNIGFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000001184 potassium carbonate Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000001225 therapeutic Effects 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 3
- 239000012022 methylating agents Substances 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- UFVLRHXFRXZBHS-UHFFFAOYSA-N 3,3,3-trichloro-2-hydroxypropanenitrile Chemical compound N#CC(O)C(Cl)(Cl)Cl UFVLRHXFRXZBHS-UHFFFAOYSA-N 0.000 claims 2
- 241000224489 Amoeba Species 0.000 claims 2
- 101700047819 CHR8 Proteins 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 239000003981 vehicle Substances 0.000 claims 2
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 claims 1
- PGVVKQANLPHXOW-UHFFFAOYSA-M 2-methoxy-2-phenylpropanoate Chemical compound COC(C)(C([O-])=O)C1=CC=CC=C1 PGVVKQANLPHXOW-UHFFFAOYSA-M 0.000 claims 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N Dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- SQRFMGKYXXMZIJ-UHFFFAOYSA-N O(C1=CC=CC=C1)C(C(=O)OC1=CC=CC=C1)CC Chemical compound O(C1=CC=CC=C1)C(C(=O)OC1=CC=CC=C1)CC SQRFMGKYXXMZIJ-UHFFFAOYSA-N 0.000 claims 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N Phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims 1
- 239000002262 Schiff base Substances 0.000 claims 1
- 150000004753 Schiff bases Chemical class 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 238000006640 acetylation reaction Methods 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 229960005215 dichloroacetic acid Drugs 0.000 claims 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- HBAIDBGDHREGFZ-UHFFFAOYSA-N phenyl 2-(4-nitrophenoxy)acetate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCC(=O)OC1=CC=CC=C1 HBAIDBGDHREGFZ-UHFFFAOYSA-N 0.000 claims 1
- ZOSCMQBDSZBUAI-UHFFFAOYSA-N phenyl 2-benzamidoacetate Chemical compound C=1C=CC=CC=1OC(=O)CNC(=O)C1=CC=CC=C1 ZOSCMQBDSZBUAI-UHFFFAOYSA-N 0.000 claims 1
- WBOKEHVGWRVHHZ-UHFFFAOYSA-N phenyl 2-hydroxy-2-phenylpropanoate Chemical compound C=1C=CC=CC=1C(O)(C)C(=O)OC1=CC=CC=C1 WBOKEHVGWRVHHZ-UHFFFAOYSA-N 0.000 claims 1
- MLAICFRYPFNMPA-UHFFFAOYSA-N phenyl 3-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(=O)CCOC1=CC=CC=C1 MLAICFRYPFNMPA-UHFFFAOYSA-N 0.000 claims 1
- HGRXBNZHQKXDPL-UHFFFAOYSA-N phenyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OC1=CC=CC=C1 HGRXBNZHQKXDPL-UHFFFAOYSA-N 0.000 claims 1
- BNZYBNYNPXKWCM-UHFFFAOYSA-N phenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC=C1 BNZYBNYNPXKWCM-UHFFFAOYSA-N 0.000 claims 1
- PDOKPQVRACLJOP-UHFFFAOYSA-N phenyl 5-bromofuran-2-carboxylate Chemical compound O1C(Br)=CC=C1C(=O)OC1=CC=CC=C1 PDOKPQVRACLJOP-UHFFFAOYSA-N 0.000 claims 1
- QSPUUVAPVKVXFB-UHFFFAOYSA-N phenyl cyclobutanecarboxylate Chemical compound C1CCC1C(=O)OC1=CC=CC=C1 QSPUUVAPVKVXFB-UHFFFAOYSA-N 0.000 claims 1
- SIENSFABYFDZCL-UHFFFAOYSA-N phenyl decanoate Chemical compound CCCCCCCCCC(=O)OC1=CC=CC=C1 SIENSFABYFDZCL-UHFFFAOYSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 59
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 235000019441 ethanol Nutrition 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000005712 crystallization Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920000591 gum Polymers 0.000 description 6
- XXXJKBSLNRMHLH-UHFFFAOYSA-N phenyl 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC1=CC=CC=C1 XXXJKBSLNRMHLH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229960000583 Acetic Acid Drugs 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- BUSOTUQRURCMCM-UHFFFAOYSA-N 3-Phenoxypropionic acid Chemical compound OC(=O)CCOC1=CC=CC=C1 BUSOTUQRURCMCM-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 229940099112 cornstarch Drugs 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- FAQJJMHZNSSFSM-UHFFFAOYSA-N Phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 229940091252 Sodium supplements Drugs 0.000 description 3
- 230000001684 chronic Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 241000220479 Acacia Species 0.000 description 2
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- 239000000375 suspending agent Substances 0.000 description 2
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- YSMYHWBQQONPRD-UHFFFAOYSA-N 2-chlorofuran Chemical compound ClC1=CC=CO1 YSMYHWBQQONPRD-UHFFFAOYSA-N 0.000 description 1
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- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 1
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- IODMEDPPCXSFLD-UHFFFAOYSA-N 5-nitrofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)O1 IODMEDPPCXSFLD-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N Benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
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- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N Isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 1
- SMKWFGIIDULNSB-UHFFFAOYSA-N O1C(=CC=C1)C(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O Chemical compound O1C(=CC=C1)C(=O)OC1=CC=C(C=C1)NC(C(Cl)Cl)=O SMKWFGIIDULNSB-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N Phenylpropanoic acid Chemical group OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 229940056729 SODIUM SULFATE ANHYDROUS Drugs 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N Tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000008061 acetanilides Chemical class 0.000 description 1
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- 239000011149 active material Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000059 antiamebic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-M caprate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZIFBQDDDTRMSDJ-UHFFFAOYSA-N furan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CO1 ZIFBQDDDTRMSDJ-UHFFFAOYSA-N 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
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- UJJLJRQIPMGXEZ-UHFFFAOYSA-M oxolane-2-carboxylate Chemical compound [O-]C(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-M 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- JDCDHJSQZSHBJT-UHFFFAOYSA-N phenyl pyridine-2-carboxylate Chemical compound C=1C=CC=NC=1C(=O)OC1=CC=CC=C1 JDCDHJSQZSHBJT-UHFFFAOYSA-N 0.000 description 1
- BUCUTHKQTIKRHI-UHFFFAOYSA-N phenyl thiophene-2-carboxylate Chemical compound C=1C=CSC=1C(=O)OC1=CC=CC=C1 BUCUTHKQTIKRHI-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- TXJKATOSKLUITR-UHFFFAOYSA-N pyrazine-2-carbonyl chloride Chemical compound ClC(=O)C1=CN=CC=N1 TXJKATOSKLUITR-UHFFFAOYSA-N 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-M pyridine-4-carboxylate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
- 230000000630 rising Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 210000003812 trophozoites Anatomy 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE578408A true BE578408A (ko) |
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ID=190985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE578408D BE578408A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE578408A (ko) |
-
0
- BE BE578408D patent/BE578408A/fr unknown
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