BE606659A - - Google Patents
Info
- Publication number
- BE606659A BE606659A BE606659DA BE606659A BE 606659 A BE606659 A BE 606659A BE 606659D A BE606659D A BE 606659DA BE 606659 A BE606659 A BE 606659A
- Authority
- BE
- Belgium
- Prior art keywords
- pyrimidine
- sulfanilamido
- methoxy
- group
- salts
- Prior art date
Links
- 239000011780 sodium chloride Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- -1 benzenesulfonyl halide Chemical class 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- PJSFRIWCGOHTNF-UHFFFAOYSA-N Sulphormetoxin Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1OC PJSFRIWCGOHTNF-UHFFFAOYSA-N 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229960001663 sulfanilamide Drugs 0.000 claims description 7
- AAJZJNHQPBMCFV-UHFFFAOYSA-N 6-chloro-5-methoxypyrimidin-4-amine Chemical compound COC1=C(N)N=CN=C1Cl AAJZJNHQPBMCFV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- IJQIGKLDBGKSNT-UHFFFAOYSA-N 4,6-dichloro-5-methoxypyrimidine Chemical compound COC1=C(Cl)N=CN=C1Cl IJQIGKLDBGKSNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000005466 alkylenyl group Chemical group 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- CGRKCGWEOIQFRD-UHFFFAOYSA-N sodium;(4-aminophenyl)sulfonylazanide Chemical compound [Na+].NC1=CC=C(S([NH-])(=O)=O)C=C1 CGRKCGWEOIQFRD-UHFFFAOYSA-N 0.000 claims description 4
- OBYHDGNNFIOYSU-UHFFFAOYSA-N 5,6-dimethoxypyrimidin-4-amine Chemical compound COC1=NC=NC(N)=C1OC OBYHDGNNFIOYSU-UHFFFAOYSA-N 0.000 claims description 3
- 229940093912 Gynecological Sulfonamides Drugs 0.000 claims description 3
- MGUHHDGODZPXID-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OCC Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OCC MGUHHDGODZPXID-UHFFFAOYSA-N 0.000 claims description 3
- ASLLQUMZZCFFNL-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OCCC Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OCCC ASLLQUMZZCFFNL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000008298 dragée Substances 0.000 claims description 3
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 claims description 3
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 229940026752 topical Sulfonamides Drugs 0.000 claims description 3
- OFVFPQRIJUCEIP-UHFFFAOYSA-N 4-amino-N-(5-ethoxy-4-methoxypyrimidin-2-yl)benzenesulfonamide Chemical compound N1=C(OC)C(OCC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 OFVFPQRIJUCEIP-UHFFFAOYSA-N 0.000 claims description 2
- KSDUVAFYUOIBOL-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OC(C)C Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OC(C)C KSDUVAFYUOIBOL-UHFFFAOYSA-N 0.000 claims description 2
- JLJMZSCXWNYDSH-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OCCC Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)OCCC JLJMZSCXWNYDSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- YIYZHARUXWKUEN-UHFFFAOYSA-N benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 YIYZHARUXWKUEN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000000844 anti-bacterial Effects 0.000 claims 2
- UUNUWFZGULQHLJ-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OC(C)C Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OC(C)C UUNUWFZGULQHLJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001681 protective Effects 0.000 claims 1
- 239000012439 solid excipient Substances 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 53
- 239000000243 solution Substances 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 238000002844 melting Methods 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 238000001953 recrystallisation Methods 0.000 description 19
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000003610 charcoal Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000009835 boiling Methods 0.000 description 14
- 229960000583 Acetic Acid Drugs 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N Allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 5
- ZTQDORFBGHGELC-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)Cl Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)Cl ZTQDORFBGHGELC-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000005712 crystallization Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- JTJKUCFCKOGABM-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)Cl Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OC)Cl JTJKUCFCKOGABM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 3
- IPOXCPQACVTTCV-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)Cl)C=C1 Chemical compound C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)Cl)C=C1 IPOXCPQACVTTCV-UHFFFAOYSA-N 0.000 description 3
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N N-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- MPEUOPDXDIBWED-UHFFFAOYSA-N 4,6-dichloro-5-ethoxypyrimidine Chemical compound CCOC1=C(Cl)N=CN=C1Cl MPEUOPDXDIBWED-UHFFFAOYSA-N 0.000 description 2
- IFLZBDWKZMQQJF-UHFFFAOYSA-N 5-methoxy-6-propan-2-yloxypyrimidin-4-amine Chemical compound COC1=C(N)N=CN=C1OC(C)C IFLZBDWKZMQQJF-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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
- KERKSHQWMCWPBT-UHFFFAOYSA-N N-phenylacetamide;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CC(=O)NC1=CC=CC=C1 KERKSHQWMCWPBT-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 150000005007 4-aminopyrimidines Chemical class 0.000 description 1
- WQVBJPKPOPHWAM-UHFFFAOYSA-N 5-methoxy-6-propoxypyrimidin-4-amine Chemical compound CCCOC1=NC=NC(N)=C1OC WQVBJPKPOPHWAM-UHFFFAOYSA-N 0.000 description 1
- PGFLCIHMBZGVGZ-UHFFFAOYSA-N 6-ethoxy-5-methoxypyrimidin-4-amine Chemical compound CCOC1=NC=NC(N)=C1OC PGFLCIHMBZGVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000287523 Ara Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ODIRUWRDBIXYAQ-UHFFFAOYSA-N C(C)(=O)N(S(=O)(C1=CC=C(C=C1)N)=O)C1=NC=NC(=C1OC)OCC Chemical compound C(C)(=O)N(S(=O)(C1=CC=C(C=C1)N)=O)C1=NC=NC(=C1OC)OCC ODIRUWRDBIXYAQ-UHFFFAOYSA-N 0.000 description 1
- YIHGAORHWDJHNS-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)OCC)C=C1 Chemical compound C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)OCC)C=C1 YIHGAORHWDJHNS-UHFFFAOYSA-N 0.000 description 1
- SQXNGSDSNMWRPZ-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)OCCC)C=C1 Chemical compound C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=NC(=C2OC)OCCC)C=C1 SQXNGSDSNMWRPZ-UHFFFAOYSA-N 0.000 description 1
- 241000873224 Capparaceae Species 0.000 description 1
- 235000017336 Capparis spinosa Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PBSUUNCQTRDFCM-UHFFFAOYSA-N N-[4-[(5,6-dimethoxypyrimidin-4-yl)sulfamoyl]phenyl]acetamide Chemical compound COC1=NC=NC(NS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=C1OC PBSUUNCQTRDFCM-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229940066842 Petrolatum Drugs 0.000 description 1
- KASPSXYHVLUBSQ-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OCC Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)NC1=NC(=C(C=N1)OCC)OCC KASPSXYHVLUBSQ-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010039447 Salmonellosis Diseases 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- NMVVJCLUYUWBSZ-UHFFFAOYSA-N aminomethylideneazanium;chloride Chemical compound Cl.NC=N NMVVJCLUYUWBSZ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ORXJMBXYSGGCHG-UHFFFAOYSA-N dimethyl 2-methoxypropanedioate Chemical compound COC(=O)C(OC)C(=O)OC ORXJMBXYSGGCHG-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-M ethoxyethane;acetate Chemical compound CC([O-])=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-M 0.000 description 1
- JUXBTCACUIWLRX-UHFFFAOYSA-N ethyl N-(4-sulfamoylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 JUXBTCACUIWLRX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- HFNQLYDPNAZRCH-UHFFFAOYSA-K hydrogen carbonate;carbonate Chemical compound OC([O-])=O.[O-]C([O-])=O HFNQLYDPNAZRCH-UHFFFAOYSA-K 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011630 iodine Substances 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001717 pathogenic Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE606659A true BE606659A (sr) |
Family
ID=192881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE606659D BE606659A (sr) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE606659A (sr) |
-
0
- BE BE606659D patent/BE606659A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1212380A (fr) | Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole | |
| CH639369A5 (fr) | Benzamides heterocycliques substitues et leurs procedes de preparation. | |
| FR2669029A1 (fr) | Nouveaux derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. | |
| EP0022705B1 (fr) | Nouveaux dérivés du tétrahydropyridinyl-indole et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| BE606659A (sr) | ||
| BE779775A (fr) | Derives de l'uree, procede pour les preparer et leurs applications | |
| CA1298301C (fr) | Benzamides, leur procede d'obtention et leurs applications therapeutiques | |
| CA1209142A (fr) | Procede d'obtention de nouvelles cyanoguanidines et des compositions pharmaceutiques en renfermant | |
| WO2000063170A1 (fr) | Derives de cyclobutene-3,4-dione en tant qu'inhibiteurs de la phosphodiesterase 5 | |
| EP0009487B1 (fr) | Nouveaux derives de la benzamide | |
| BE858864A (fr) | Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation | |
| CH620429A5 (sr) | ||
| EP0254611B1 (fr) | Dérivés 8-phénylthiotétrahydroquinoléines substitués et leurs sels, leur préparation à titre de médicaments et les compositions les renfermant | |
| WO2000051973A1 (fr) | Derives de cyclobutene-3,4-dione leur preparation et leur application en therapeutique | |
| CH373038A (fr) | Procédé de préparation de nouveaux éthers de pipéridyl-2 aryl méthanols | |
| JP2001302611A (ja) | ５−トリフルオロメチルジヒドロウラシルの製造法 | |
| JPH0229672B2 (ja) | 11chikann55merukaputootetorazoorunoseizoho | |
| JP2003504365A (ja) | 新規方法 | |
| FR2712290A1 (fr) | Oxazino-acridines substituées, leur préparation et leur application en thérapeutique. | |
| FR2483419A1 (fr) | Procede de preparation de la n-(2-(2-thenoyl)-thiopropionyl)-glicine | |
| BE641253A (sr) | ||
| HUT59674A (en) | Process for producing new 5-/ph+noxy-alkanoyl-amino/-uracyl derivatives and pharmaceutical compositions contaiing them | |
| CH408953A (fr) | Procédé de préparation de nouveaux carbazates substitués | |
| FR2575470A1 (fr) | Derives amines de n-imidazolylmethyl-diphenylazomethines, leur preparation et leur application en therapeutique | |
| HUT64736A (en) | Method for producing thyramine derivatives |