BE595766A - - Google Patents
Info
- Publication number
- BE595766A BE595766A BE595766DA BE595766A BE 595766 A BE595766 A BE 595766A BE 595766D A BE595766D A BE 595766DA BE 595766 A BE595766 A BE 595766A
- Authority
- BE
- Belgium
- Prior art keywords
- quaternary ammonium
- ammonium compound
- formula
- furfurylamine
- methyl
- Prior art date
Links
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000012022 methylating agents Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- VDJHUVSOEDSQMJ-UHFFFAOYSA-N N-(furan-2-ylmethyl)-2-phenoxyethanamine Chemical compound C=1C=COC=1CNCCOC1=CC=CC=C1 VDJHUVSOEDSQMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- -1 phenoxyethyl Chemical class 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- RUHVDRGWCIAFLG-UHFFFAOYSA-N N,N-dimethyl-2-phenoxyethanamine Chemical compound CN(C)CCOC1=CC=CC=C1 RUHVDRGWCIAFLG-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000004429 atoms Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- VFIAOIVGTFADLM-UHFFFAOYSA-N 1-(furan-2-yl)-N,N-dimethylmethanamine Chemical compound CN(C)CC1=CC=CO1 VFIAOIVGTFADLM-UHFFFAOYSA-N 0.000 claims 1
- WALDBAZVJPWWNO-UHFFFAOYSA-N CN(CC1=CC=CO1)CCOC1=CC=CC=C1 Chemical compound CN(CC1=CC=CO1)CCOC1=CC=CC=C1 WALDBAZVJPWWNO-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 12
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- DDRPCXLAQZKBJP-UHFFFAOYSA-N Furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- 206010061217 Infestation Diseases 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 239000008101 lactose Substances 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
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- ZDEJJQHQIOWTPC-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1OCCBr ZDEJJQHQIOWTPC-UHFFFAOYSA-N 0.000 description 1
- NSMQOWMNTQCZPM-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-fluorobenzene Chemical compound FC1=CC=CC=C1OCCBr NSMQOWMNTQCZPM-UHFFFAOYSA-N 0.000 description 1
- ABXRTJHEVCZIAG-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-methylbenzene Chemical compound CC1=CC=CC=C1OCCBr ABXRTJHEVCZIAG-UHFFFAOYSA-N 0.000 description 1
- AHOFWSHLRKOJBS-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OCCBr AHOFWSHLRKOJBS-UHFFFAOYSA-N 0.000 description 1
- DGLIOWSKNOCHEX-UHFFFAOYSA-N 1-(furan-2-yl)-N-methylmethanamine Chemical compound CNCC1=CC=CO1 DGLIOWSKNOCHEX-UHFFFAOYSA-N 0.000 description 1
- LOVVQTBEUIBASP-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)benzene Chemical compound BrCCOC1=CC=CC=C1Br LOVVQTBEUIBASP-UHFFFAOYSA-N 0.000 description 1
- VQUYNUJARXBNPK-UHFFFAOYSA-N 2-chloroethoxybenzene Chemical compound ClCCOC1=CC=CC=C1 VQUYNUJARXBNPK-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 1
- 241001147672 Ancylostoma caninum Species 0.000 description 1
- JHLNERQLKQQLRZ-UHFFFAOYSA-N Calcium silicate Chemical compound [Ca+2].[Ca+2].[O-][Si]([O-])([O-])[O-] JHLNERQLKQQLRZ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 210000004400 Mucous Membrane Anatomy 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical compound OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229960002798 cetrimide Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 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
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZIPQNVVCEHWMBV-UHFFFAOYSA-N furan-2-ylmethanamine;hydrochloride Chemical compound Cl.NCC1=CC=CO1 ZIPQNVVCEHWMBV-UHFFFAOYSA-N 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M laurate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O methylammonium Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000003071 parasitic Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE595766A true BE595766A (ko) |
Family
ID=192242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE595766D BE595766A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE595766A (ko) |
-
0
- BE BE595766D patent/BE595766A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE1013213A6 (fr) | Procede de preparation de citalopram pur. | |
| EP0073161B1 (fr) | Nouveaux dérivés de la pyrazine actifs sur le système nerveux central | |
| EP0377381A1 (fr) | Procédé de préparation du phényl-1 diéthylaminocarbonyl-1 phtalimidométhyl-2 cyclopropane Z | |
| EP0109866A1 (fr) | Nouveaux dérivés de la sulfonylurée, leurs procédés de préparation et les compositions pharmaceutiques les renfermant | |
| FR3084668A1 (fr) | Procede de preparation monotope de composes organo-iodes intermediaires a la synthese du ioversol | |
| EP2331555B1 (fr) | Dérives ferroceniques a activite anticancereuse | |
| CH406195A (fr) | Procédé de préparation de dérivés des acides 4-halo-3-sulfamoyl-benzoïques | |
| EP0037344B1 (fr) | Amino-alcoxy pyrazoles, procédé pour leur préparation, et médicaments les contenant | |
| BE595766A (ko) | ||
| EP0183577B1 (fr) | Dérivés du thiadiazole actifs sur le système nerveux central, procédé d'obtension et compositions pharmaceutiques les contenant | |
| CH363023A (fr) | Procédé de préparation des antipodes d d'amines tertiaires | |
| FR2492821A1 (fr) | Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant | |
| EP0070753A1 (fr) | (Aza-1 bicyclo-(2,2,2) octyl-3) -10 10H phénothiazine-sulfonamide-2 et dérivés | |
| EP0196943A1 (fr) | Nouveaux dérivés 8-thiotétrahydroquinoléines et leurs sels | |
| BE636041A (ko) | ||
| FR2560193A1 (fr) | Derives d'aminodiaryl sulfoxyde, procede pour leur preparation et compositions pharmaceutiques et pesticides les contenant | |
| BE866910A (fr) | Derives de benzimidazole contenant du soufre, leur procede de preparation et intermediaires utilisables dans leur production | |
| BE582972A (ko) | ||
| BE563330A (ko) | ||
| FR2523129A1 (fr) | Derives de 3-azetidinylethyl-1-phenyl-2-imidazolidinone, medicaments les contenant et procede pour leur preparation | |
| BE621597A (ko) | ||
| EP0254611A1 (fr) | Dérivés 8-phénylthiotétrahydroquinoléines substitués et leurs sels, leur préparation à titre de médicaments et les compositions les renfermant | |
| BE587459A (ko) | ||
| BE564356A (ko) | ||
| BE580111A (ko) |