BE569109A - - Google Patents
Info
- Publication number
- BE569109A BE569109A BE569109DA BE569109A BE 569109 A BE569109 A BE 569109A BE 569109D A BE569109D A BE 569109DA BE 569109 A BE569109 A BE 569109A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- diethoxyethyl
- acid
- formula
- halogen
- Prior art date
Links
- -1 2,4-dichlorobenzyl Chemical group 0.000 claims description 68
- 239000011780 sodium chloride Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 150000003973 alkyl amines Chemical class 0.000 claims description 19
- 238000007792 addition Methods 0.000 claims description 18
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical group ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- WCGGWVOVFQNRRS-UHFFFAOYSA-N Dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- POOMPFUTQZIBHT-UHFFFAOYSA-N Cl.C(C)OC(CNCC1=CC(=C(C=C1)Cl)Cl)OCC Chemical compound Cl.C(C)OC(CNCC1=CC(=C(C=C1)Cl)Cl)OCC POOMPFUTQZIBHT-UHFFFAOYSA-N 0.000 claims description 2
- AZOLBNURUCZYCM-UHFFFAOYSA-N N-[(3,4-dichlorophenyl)methyl]-2,2-diethoxyethanamine Chemical compound CCOC(OCC)CNCC1=CC=C(Cl)C(Cl)=C1 AZOLBNURUCZYCM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 2
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 91
- 239000000047 product Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000012458 free base Substances 0.000 description 10
- OVXJWSYBABKZMD-UHFFFAOYSA-N 2-chloro-1,1-diethoxyethane Chemical compound CCOC(CCl)OCC OVXJWSYBABKZMD-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- PAYRESLDMXOCIY-UHFFFAOYSA-N N-[(2,4-dichlorophenyl)methyl]-2,2-diethoxyethanamine Chemical compound CCOC(OCC)CNCC1=CC=C(Cl)C=C1Cl PAYRESLDMXOCIY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000036850 Cld Effects 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-Dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 3
- YUIKPESWSMJSMP-UHFFFAOYSA-N 2,2-dibromoacetamide Chemical compound NC(=O)C(Br)Br YUIKPESWSMJSMP-UHFFFAOYSA-N 0.000 description 3
- SCQYFFYVHXLAQV-UHFFFAOYSA-N 2,2-dibromoacetyl bromide Chemical compound BrC(Br)C(Br)=O SCQYFFYVHXLAQV-UHFFFAOYSA-N 0.000 description 3
- 241000699800 Cricetinae Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 230000000240 adjuvant Effects 0.000 description 3
- 230000000507 anthelmentic Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 125000005059 halophenyl group Chemical group 0.000 description 3
- 230000003285 pharmacodynamic Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- HCEURPIIGJWLTF-UHFFFAOYSA-N 2,2-diethoxy-N-[(2,4,6-trimethylphenyl)methyl]ethanamine Chemical compound CCOC(OCC)CNCC1=C(C)C=C(C)C=C1C HCEURPIIGJWLTF-UHFFFAOYSA-N 0.000 description 2
- ALCNYHIPSSHWOV-UHFFFAOYSA-N C(C(C)C)OC(CNCC1=CC(=CC=C1)I)OCC(C)C Chemical compound C(C(C)C)OC(CNCC1=CC(=CC=C1)I)OCC(C)C ALCNYHIPSSHWOV-UHFFFAOYSA-N 0.000 description 2
- JRQZGLYIOLWOHM-UHFFFAOYSA-N C(C)OC(CNCC1=CC(=CC=C1)C(C)C)OCC Chemical compound C(C)OC(CNCC1=CC(=CC=C1)C(C)C)OCC JRQZGLYIOLWOHM-UHFFFAOYSA-N 0.000 description 2
- 229960003563 Calcium Carbonate Drugs 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 230000000973 chemotherapeutic Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- AAWZDTNXLSGCEK-WYWMIBKRSA-M (-)-quinate Chemical compound O[C@@H]1C[C@](O)(C([O-])=O)C[C@@H](O)[C@H]1O AAWZDTNXLSGCEK-WYWMIBKRSA-M 0.000 description 1
- IBKDNYJEYFQCER-UHFFFAOYSA-N (2,4,6-trichlorophenyl)methanamine Chemical compound NCC1=C(Cl)C=C(Cl)C=C1Cl IBKDNYJEYFQCER-UHFFFAOYSA-N 0.000 description 1
- DGSRAILDFBJNQI-UHFFFAOYSA-N (2,4,6-trimethylphenyl)methanamine Chemical compound CC1=CC(C)=C(CN)C(C)=C1 DGSRAILDFBJNQI-UHFFFAOYSA-N 0.000 description 1
- LDVMPLPFCNJLQZ-UHFFFAOYSA-N (2,4-dibromophenyl)methanamine Chemical compound NCC1=CC=C(Br)C=C1Br LDVMPLPFCNJLQZ-UHFFFAOYSA-N 0.000 description 1
- SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 description 1
- IOSPRWNZCSXFRO-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine;hydrochloride Chemical compound [Cl-].[NH3+]CC1=CC=C(Cl)C=C1Cl IOSPRWNZCSXFRO-UHFFFAOYSA-N 0.000 description 1
- IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
- LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 1
- UMGGFLATENTNHY-UHFFFAOYSA-N (3-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=CC(CN)=C1 UMGGFLATENTNHY-UHFFFAOYSA-N 0.000 description 1
- AUAURTOWAVNOPQ-UHFFFAOYSA-N (4-butoxyphenyl)methanamine Chemical compound CCCCOC1=CC=C(CN)C=C1 AUAURTOWAVNOPQ-UHFFFAOYSA-N 0.000 description 1
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 1
- ACNSGHYWIIECBM-UHFFFAOYSA-N (4-hexoxyphenyl)methanamine Chemical compound CCCCCCOC1=CC=C(CN)C=C1 ACNSGHYWIIECBM-UHFFFAOYSA-N 0.000 description 1
- OJKANOMRJNKQRV-UHFFFAOYSA-N (4-hexylphenyl)methanamine Chemical compound CCCCCCC1=CC=C(CN)C=C1 OJKANOMRJNKQRV-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- RPBLJRRVGJPMEZ-UHFFFAOYSA-N 1-(2-chloro-1-propoxyethoxy)propane Chemical compound CCCOC(CCl)OCCC RPBLJRRVGJPMEZ-UHFFFAOYSA-N 0.000 description 1
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 1
- PNAXKTCJNDCZLV-UHFFFAOYSA-N 2,2-diethoxy-N-[(4-fluorophenyl)methyl]ethanamine Chemical compound CCOC(OCC)CNCC1=CC=C(F)C=C1 PNAXKTCJNDCZLV-UHFFFAOYSA-N 0.000 description 1
- VGKFZQHMQQVIGB-UHFFFAOYSA-N 2,2-diethoxy-N-[(4-propan-2-ylphenyl)methyl]ethanamine Chemical compound CCOC(OCC)CNCC1=CC=C(C(C)C)C=C1 VGKFZQHMQQVIGB-UHFFFAOYSA-N 0.000 description 1
- MDHNXBJDQCMHGH-UHFFFAOYSA-N 2-(3-methoxy-4-propan-2-ylphenyl)ethanamine Chemical compound COC1=CC(CCN)=CC=C1C(C)C MDHNXBJDQCMHGH-UHFFFAOYSA-N 0.000 description 1
- GKRKWDWETUTQOT-UHFFFAOYSA-N 2-bromo-2-chloroacetamide Chemical compound NC(=O)C(Cl)Br GKRKWDWETUTQOT-UHFFFAOYSA-N 0.000 description 1
- YVUFDPUKVYAZNX-UHFFFAOYSA-N 2-bromo-2-chloroacetyl chloride Chemical compound ClC(Br)C(Cl)=O YVUFDPUKVYAZNX-UHFFFAOYSA-N 0.000 description 1
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940095564 Anhydrous Calcium Sulfate Drugs 0.000 description 1
- FJTBFBLXQKTPIH-UHFFFAOYSA-N C(C(C)C)OC(CCl)OCC(C)C Chemical compound C(C(C)C)OC(CCl)OCC(C)C FJTBFBLXQKTPIH-UHFFFAOYSA-N 0.000 description 1
- YWEUUHQVZBQUBG-UHFFFAOYSA-N C(C)OC(CNCC1=C(C=C(C=C1)Cl)OCCC)OCC Chemical compound C(C)OC(CNCC1=C(C=C(C=C1)Cl)OCCC)OCC YWEUUHQVZBQUBG-UHFFFAOYSA-N 0.000 description 1
- MBWKOSZUJVLNCE-UHFFFAOYSA-N C(C)OC(CNCC1=C(C=C(C=C1Cl)Cl)Cl)OCC Chemical compound C(C)OC(CNCC1=C(C=C(C=C1Cl)Cl)Cl)OCC MBWKOSZUJVLNCE-UHFFFAOYSA-N 0.000 description 1
- KHVQVUUIFVCZIK-UHFFFAOYSA-N C(C)OC(CNCC1=CC=C(C=C1)CCCCCC)OCC Chemical compound C(C)OC(CNCC1=CC=C(C=C1)CCCCCC)OCC KHVQVUUIFVCZIK-UHFFFAOYSA-N 0.000 description 1
- WBCMPXCRPPCZSO-UHFFFAOYSA-N C(C)OC(CNCC1=CC=C(C=C1)OCCCCCC)OCC Chemical compound C(C)OC(CNCC1=CC=C(C=C1)OCCCCCC)OCC WBCMPXCRPPCZSO-UHFFFAOYSA-N 0.000 description 1
- NUJROLXICXKCJM-UHFFFAOYSA-N C(CCCCC)OC(CNCCC1=CC(=C(C(=C1)OC)OC)OC)OCCCCCC Chemical compound C(CCCCC)OC(CNCCC1=CC(=C(C(=C1)OC)OC)OC)OCCCCCC NUJROLXICXKCJM-UHFFFAOYSA-N 0.000 description 1
- HYQGKAMPRYIBSF-UHFFFAOYSA-N COC(CNCCC1=CC(=C(C=C1)C(C)C)OC)OC Chemical compound COC(CNCCC1=CC(=C(C=C1)C(C)C)OC)OC HYQGKAMPRYIBSF-UHFFFAOYSA-N 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L Calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N Chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 229960003677 Chloroquine Drugs 0.000 description 1
- 240000004524 Derris elliptica Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- WFJIVOKAWHGMBH-UHFFFAOYSA-N Hexylresorcinol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 1
- 241001464384 Hymenolepis nana Species 0.000 description 1
- VTINVTXINAIUKD-UHFFFAOYSA-N IC(C(=O)I)I Chemical compound IC(C(=O)I)I VTINVTXINAIUKD-UHFFFAOYSA-N 0.000 description 1
- RHCSKNNOAZULRK-UHFFFAOYSA-N Mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 1
- SEMYTOOACKPWDM-UHFFFAOYSA-N N,N-dibromo-1-phenylmethanamine Chemical compound BrN(Br)CC1=CC=CC=C1 SEMYTOOACKPWDM-UHFFFAOYSA-N 0.000 description 1
- JTAHMMVOHGZJLE-UHFFFAOYSA-N N-[(2,4-dichlorophenyl)methyl]-2,2-dimethoxyethanamine Chemical compound COC(OC)CNCC1=CC=C(Cl)C=C1Cl JTAHMMVOHGZJLE-UHFFFAOYSA-N 0.000 description 1
- YFHFZWDVEIQTDF-UHFFFAOYSA-N N-[(4-butoxyphenyl)methyl]-2,2-diethoxyethanamine Chemical compound CCCCOC1=CC=C(CNCC(OCC)OCC)C=C1 YFHFZWDVEIQTDF-UHFFFAOYSA-N 0.000 description 1
- IZELWSRWUAZIGZ-UHFFFAOYSA-N N-butoxy-1-phenylmethanamine Chemical compound CCCCONCC1=CC=CC=C1 IZELWSRWUAZIGZ-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-WYWMIBKRSA-N Quinic acid Chemical compound O[C@@H]1C[C@](O)(C(O)=O)C[C@@H](O)[C@H]1O AAWZDTNXLSGCEK-WYWMIBKRSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003569 amebicidal Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000059 antiamebic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000052616 bacterial pathogens Species 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 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
- 230000003292 diminished Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 231100000486 side effect Toxicity 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE569109A true BE569109A (xx) |
Family
ID=188193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE569109D BE569109A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE569109A (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163607A2 (de) * | 1984-05-28 | 1985-12-04 | Ciba-Geigy Ag | Mittel zum Schützen von Kulturpflanzen vor der phytotoxischen Wirkung von herbizid wirksamen Chloracetaniliden |
| US4897109A (en) * | 1984-05-28 | 1990-01-30 | Ciba-Geigy Corporation | Compositions for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides |
-
0
- BE BE569109D patent/BE569109A/fr unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163607A2 (de) * | 1984-05-28 | 1985-12-04 | Ciba-Geigy Ag | Mittel zum Schützen von Kulturpflanzen vor der phytotoxischen Wirkung von herbizid wirksamen Chloracetaniliden |
| EP0163607A3 (en) * | 1984-05-28 | 1986-11-26 | Ciba-Geigy Ag | Means for the protection of culture plants against the phytotoxic action of chloracetanilide herbicides |
| US4897109A (en) * | 1984-05-28 | 1990-01-30 | Ciba-Geigy Corporation | Compositions for protecting culture plants from the phytotoxic action of herbicidally active chloracetanilides |
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