BE480199A - - Google Patents
Info
- Publication number
- BE480199A BE480199A BE480199DA BE480199A BE 480199 A BE480199 A BE 480199A BE 480199D A BE480199D A BE 480199DA BE 480199 A BE480199 A BE 480199A
- Authority
- BE
- Belgium
- Prior art keywords
- sulfanilamide
- grams
- solution
- sep
- quinoxalyl
- Prior art date
Links
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 33
- 229960001663 sulfanilamide Drugs 0.000 claims description 33
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 12
- OSZFJGLXXUAMEJ-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonyl chloride Chemical compound CC(=O)C1=CC(N)=CC=C1S(Cl)(=O)=O OSZFJGLXXUAMEJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- PXDLUYLWPJMGJA-UHFFFAOYSA-N 2-chloro-3-methylquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(C)=NC2=C1 PXDLUYLWPJMGJA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical group C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 33
- 238000002844 melting Methods 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- -1 amine derivatives of quinoxaline Chemical class 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000001187 sodium carbonate Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000005712 crystallization Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- HADMFXUIQRIRMV-UHFFFAOYSA-N 1,2-dihydroxyethane-1,2-disulfonic acid Chemical compound OS(=O)(=O)C(O)C(O)S(O)(=O)=O HADMFXUIQRIRMV-UHFFFAOYSA-N 0.000 description 3
- WGHZDFAULZNZJE-UHFFFAOYSA-N 3-methylquinoxalin-2-amine Chemical compound C1=CC=C2N=C(N)C(C)=NC2=C1 WGHZDFAULZNZJE-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- GYSCSMIVGRTCQY-UHFFFAOYSA-N 2-chloro-5-methylquinoxaline Chemical compound ClC1=CN=C2C(C)=CC=CC2=N1 GYSCSMIVGRTCQY-UHFFFAOYSA-N 0.000 description 2
- YKFVEQQFGNMNCH-UHFFFAOYSA-N 2-methylquinoxalin-6-amine Chemical compound C1=C(N)C=CC2=NC(C)=CN=C21 YKFVEQQFGNMNCH-UHFFFAOYSA-N 0.000 description 2
- LSAZSONOFASSJF-UHFFFAOYSA-N 5-methyl-1H-quinoxalin-2-one Chemical compound N1C(=O)C=NC2=C1C=CC=C2C LSAZSONOFASSJF-UHFFFAOYSA-N 0.000 description 2
- RZHDPRJKURHDFX-UHFFFAOYSA-N 8-methylquinoxalin-6-amine Chemical compound C1=CN=C2C(C)=CC(N)=CC2=N1 RZHDPRJKURHDFX-UHFFFAOYSA-N 0.000 description 2
- 210000004369 Blood Anatomy 0.000 description 2
- 241000588832 Bordetella pertussis Species 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 230000002458 infectious Effects 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N pyruvic aldehyde Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RKMFFOLUBJFMBQ-UHFFFAOYSA-N (4-amino-2-azaniumylphenyl)azanium;dichloride Chemical compound Cl.Cl.NC1=CC=C(N)C(N)=C1 RKMFFOLUBJFMBQ-UHFFFAOYSA-N 0.000 description 1
- AHCZCBQPNQSTIG-UHFFFAOYSA-N 1-oxoethanesulfonamide Chemical compound CC(=O)S(N)(=O)=O AHCZCBQPNQSTIG-UHFFFAOYSA-N 0.000 description 1
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
- ZILYFNINVGYJEV-UHFFFAOYSA-N 2-aminobenzenesulfonamide;quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21.NC1=CC=CC=C1S(N)(=O)=O ZILYFNINVGYJEV-UHFFFAOYSA-N 0.000 description 1
- FCMRHMPITHLLLA-UHFFFAOYSA-N 2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N FCMRHMPITHLLLA-UHFFFAOYSA-N 0.000 description 1
- XZLZKVFCZDXISH-UHFFFAOYSA-N 4-methyl-6-nitrobenzene-1,3-diamine Chemical compound CC1=CC([N+]([O-])=O)=C(N)C=C1N XZLZKVFCZDXISH-UHFFFAOYSA-N 0.000 description 1
- CQLOYHZZZCWHSG-UHFFFAOYSA-N 5-Methylquinoxaline Chemical compound C1=CN=C2C(C)=CC=CC2=N1 CQLOYHZZZCWHSG-UHFFFAOYSA-N 0.000 description 1
- GUJOFWGIBDKFJS-UHFFFAOYSA-N 5-methylbenzene-1,2,3-triamine Chemical compound CC1=CC(N)=C(N)C(N)=C1 GUJOFWGIBDKFJS-UHFFFAOYSA-N 0.000 description 1
- AKARWUFKICDPGJ-UHFFFAOYSA-N 5-methylquinoxalin-2-amine Chemical compound NC1=CN=C2C(C)=CC=CC2=N1 AKARWUFKICDPGJ-UHFFFAOYSA-N 0.000 description 1
- 239000001640 5-methylquinoxaline Substances 0.000 description 1
- HHHCVAWXYCRRBP-UHFFFAOYSA-N 7-methylquinoxalin-5-amine Chemical compound N1=CC=NC2=CC(C)=CC(N)=C21 HHHCVAWXYCRRBP-UHFFFAOYSA-N 0.000 description 1
- SCHXCJAURQWQNM-UHFFFAOYSA-N 7-methylquinoxalin-6-amine Chemical compound C1=CN=C2C=C(N)C(C)=CC2=N1 SCHXCJAURQWQNM-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N Bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N Glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 1
- 229940015043 Glyoxal Drugs 0.000 description 1
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 1
- QYBQEJWLQUSQIT-UHFFFAOYSA-N OC1=NC2=CC=CC(=C2N=C1C(=O)O)C Chemical compound OC1=NC2=CC=CC(=C2N=C1C(=O)O)C QYBQEJWLQUSQIT-UHFFFAOYSA-N 0.000 description 1
- PSNWURBBURGFTB-UHFFFAOYSA-N OC1=NC2=CC=CC(=C2N=C1C(=O)OCC)C Chemical compound OC1=NC2=CC=CC(=C2N=C1C(=O)OCC)C PSNWURBBURGFTB-UHFFFAOYSA-N 0.000 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N Quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
- 241000365640 Serinus flaviventris Species 0.000 description 1
- NHZLNPMOSADWGC-UHFFFAOYSA-N Sulfaquinoxaline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 description 1
- 208000001877 Whooping Cough Diseases 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000844 anti-bacterial Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 201000005702 pertussis Diseases 0.000 description 1
- 230000003389 potentiating Effects 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MSGRFBKVMUKEGZ-UHFFFAOYSA-N quinoxalin-6-amine Chemical compound N1=CC=NC2=CC(N)=CC=C21 MSGRFBKVMUKEGZ-UHFFFAOYSA-N 0.000 description 1
- CGJMVNVWQHPASW-UHFFFAOYSA-N quinoxaline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CN=C21 CGJMVNVWQHPASW-UHFFFAOYSA-N 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229940026752 topical Sulfonamides Drugs 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE480199A true BE480199A (pt) |
Family
ID=127490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE480199D BE480199A (pt) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE480199A (pt) |
-
0
- BE BE480199D patent/BE480199A/fr unknown
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