SE439012B - Forfarande for framstellning av 5-sulfamoyl-ortanilsyror - Google Patents
Forfarande for framstellning av 5-sulfamoyl-ortanilsyrorInfo
- Publication number
- SE439012B SE439012B SE7804956A SE7804956A SE439012B SE 439012 B SE439012 B SE 439012B SE 7804956 A SE7804956 A SE 7804956A SE 7804956 A SE7804956 A SE 7804956A SE 439012 B SE439012 B SE 439012B
- Authority
- SE
- Sweden
- Prior art keywords
- acid
- group
- sulfamoyl
- general formula
- ester
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 title claims description 15
- 150000007513 acids Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 phenyloxy Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000565 sulfonamide group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- LZJVSPPXXGXGQL-UHFFFAOYSA-N 4-aminobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(N)C=C1 LZJVSPPXXGXGQL-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000011734 sodium Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- 238000003756 stirring Methods 0.000 description 16
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 10
- 239000012467 final product Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229940072033 potash Drugs 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MVVSYCZQUGNLNY-UHFFFAOYSA-N 4-chloro-2-fluoro-5-sulfamoylbenzenesulfonic acid;dihydrate Chemical compound O.O.NS(=O)(=O)C1=CC(S(O)(=O)=O)=C(F)C=C1Cl MVVSYCZQUGNLNY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 150000003459 sulfonic acid esters Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- GZOQORPTSADPON-UHFFFAOYSA-N (4-methylphenyl) 2,4-dichloro-5-sulfamoylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1Cl GZOQORPTSADPON-UHFFFAOYSA-N 0.000 description 2
- BJCYSSVOZRURIP-UHFFFAOYSA-N (4-methylphenyl) 2-chloro-4-(4-methylphenoxy)-5-sulfamoylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1OC1=CC(Cl)=C(S(=O)(=O)OC=2C=CC(C)=CC=2)C=C1S(N)(=O)=O BJCYSSVOZRURIP-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 2
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KKOYVNMMRAKNLV-UHFFFAOYSA-N (2-methylphenyl) 2-chloro-4-phenoxy-5-sulfamoylbenzenesulfonate Chemical compound CC1=CC=CC=C1OS(=O)(=O)C(C(=C1)Cl)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 KKOYVNMMRAKNLV-UHFFFAOYSA-N 0.000 description 1
- DUGDVFGFCREDOK-UHFFFAOYSA-N (4-methylphenyl) 2-chloro-4-methyl-5-sulfamoylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC(S(N)(=O)=O)=C(C)C=C1Cl DUGDVFGFCREDOK-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- BMHZXKJGNPWTME-UHFFFAOYSA-N 2-chloro-4-fluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(F)C=C1Cl BMHZXKJGNPWTME-UHFFFAOYSA-N 0.000 description 1
- VPOMSPZBQMDLTM-UHFFFAOYSA-N 3,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1 VPOMSPZBQMDLTM-UHFFFAOYSA-N 0.000 description 1
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- TXBDAHLPHMWZPE-UHFFFAOYSA-N 5-amino-2-chloro-4-fluorobenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=C(Cl)C=C1F TXBDAHLPHMWZPE-UHFFFAOYSA-N 0.000 description 1
- DSFGXPJYDCSWTA-UHFFFAOYSA-N 7-[2-hydroxy-3-[2-hydroxyethyl(methyl)amino]propyl]-1,3-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(O)CN(CCO)C DSFGXPJYDCSWTA-UHFFFAOYSA-N 0.000 description 1
- GWPGDZPXOZATKL-UHFFFAOYSA-N 9h-carbazol-2-ol Chemical compound C1=CC=C2C3=CC=C(O)C=C3NC2=C1 GWPGDZPXOZATKL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
- 238000007192 Meerwein reaction reaction Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- UUDJQZPFEDJRMU-UHFFFAOYSA-N NC=NS(=O)=O Chemical class NC=NS(=O)=O UUDJQZPFEDJRMU-UHFFFAOYSA-N 0.000 description 1
- QJVKUZSFWDCLHP-UHFFFAOYSA-N NNS(N)(=O)=O Chemical compound NNS(N)(=O)=O QJVKUZSFWDCLHP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
- 229960002576 amiloride Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- WGXVWSQHJHMQIZ-UHFFFAOYSA-N bis(4-methylphenyl) 4,6-dichlorobenzene-1,3-disulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC(S(=O)(=O)OC=2C=CC(C)=CC=2)=C(Cl)C=C1Cl WGXVWSQHJHMQIZ-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- RFNQYUYBJJALJS-UHFFFAOYSA-M copper(1+);chloride;dihydrate Chemical compound O.O.[Cl-].[Cu+] RFNQYUYBJJALJS-UHFFFAOYSA-M 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- VQKLRVZQQYVIJW-UHFFFAOYSA-N dihydralazine Chemical compound C1=CC=C2C(NN)=NN=C(NN)C2=C1 VQKLRVZQQYVIJW-UHFFFAOYSA-N 0.000 description 1
- 229960002877 dihydralazine Drugs 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960001614 levamisole Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- HXHWWRAUSKLFDB-UHFFFAOYSA-N n'-(2-chloro-4-fluorophenyl)sulfonyl-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NS(=O)(=O)C1=CC=C(F)C=C1Cl HXHWWRAUSKLFDB-UHFFFAOYSA-N 0.000 description 1
- WHFMFMZQFCRPFE-UHFFFAOYSA-N n'-(5-amino-2-chloro-4-fluorophenyl)sulfonyl-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NS(=O)(=O)C1=CC(N)=C(F)C=C1Cl WHFMFMZQFCRPFE-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PTYGJMLRPJMKFR-UHFFFAOYSA-N phenyl 2-chloro-4-phenoxy-5-sulfamoylbenzenesulfonate Chemical compound NS(=O)(=O)C1=CC(S(=O)(=O)OC=2C=CC=CC=2)=C(Cl)C=C1OC1=CC=CC=C1 PTYGJMLRPJMKFR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000054 salidiuretic effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000002130 sulfonic acid ester group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229940118318 xanthinol Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2718871A DE2718871C3 (de) | 1977-04-28 | 1977-04-28 | N-(2-Furylmethyl)-5-sulfamoylorthanilsäuren und deren physiologisch verträgliche Salze und Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Oedemkrankheiten und Bluthochdruck |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7804956L SE7804956L (sv) | 1978-10-29 |
| SE439012B true SE439012B (sv) | 1985-05-28 |
Family
ID=6007484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7804956A SE439012B (sv) | 1977-04-28 | 1978-04-28 | Forfarande for framstellning av 5-sulfamoyl-ortanilsyror |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4161533A (de) |
| JP (1) | JPS53135966A (de) |
| AT (1) | AT363463B (de) |
| BE (1) | BE866565A (de) |
| CA (1) | CA1109477A (de) |
| CH (1) | CH638798A5 (de) |
| DE (1) | DE2718871C3 (de) |
| DK (1) | DK183678A (de) |
| ES (1) | ES469058A1 (de) |
| FI (1) | FI65996C (de) |
| FR (1) | FR2388809A1 (de) |
| GB (1) | GB1587105A (de) |
| HU (1) | HU177454B (de) |
| IL (1) | IL54585A (de) |
| IT (1) | IT1094565B (de) |
| NL (1) | NL7804558A (de) |
| SE (1) | SE439012B (de) |
| ZA (1) | ZA782421B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3009229A1 (de) * | 1980-03-11 | 1981-10-15 | Hoechst Ag, 6000 Frankfurt | 2,4-diamino-5-sulfamoylbenzolsulfosaeuren und verfahen zu ihrer herstellung |
| DE3034880A1 (de) * | 1980-09-16 | 1982-04-29 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 5- sulfamoyl-orthanilsaeuren |
| FR2614619B1 (fr) * | 1987-04-29 | 1989-09-15 | Sanofi Sa | Procede de preparation de n-((chloro-2)-benzyl) (thienyl-2)-2 ethylamine |
| AU2005216879B2 (en) * | 2004-02-20 | 2009-12-10 | Aventis Pharmaceuticals Inc | Furosemide derivatives as modulators of HM74 and their use for the treatment of inflammation |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1802208U (de) | 1959-10-01 | 1959-12-17 | Hugo Guddar | Verschluss fuer pelze aller art. |
| DE1122541B (de) | 1959-12-28 | 1962-01-25 | Hoechst Ag | Verfahren zur Herstellung von Sulfamyl-anthranilsaeuren |
| CH383403A (de) | 1960-12-23 | 1964-10-31 | Sandoz Ag | Verfahren zur Herstellung von neuen Sulfonamiden |
| DE1278443C2 (de) | 1963-11-30 | 1975-07-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,4-disulfonamid-1-chlorbenzolen |
| DE1543602C3 (de) | 1966-06-16 | 1974-09-26 | Bayer Ag, 5090 Leverkusen | Substituierte Disulfonamide sowie deren Salze mit nichttoxischen Basen und Verfahren zu ihrer Herstellung |
| US3454562A (en) * | 1966-10-07 | 1969-07-08 | Smithkline Corp | 5 - carbamoylsulfamoyl - n - substitutedanthranilic acids and esters thereof |
| DE1802208A1 (de) * | 1968-10-10 | 1970-05-14 | Hoechst Ag | Verfahren zur Herstellung salidiuretisch wirksamer Sulfamylanthranilsaeuren |
| US3875150A (en) | 1969-04-29 | 1975-04-01 | Leo Pharm Prod Ltd | New sulfamyl-anthranilic acids |
| DE2247828A1 (de) | 1972-09-29 | 1974-04-04 | Hoechst Ag | Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung |
-
1977
- 1977-04-28 DE DE2718871A patent/DE2718871C3/de not_active Expired
-
1978
- 1978-04-22 ES ES469058A patent/ES469058A1/es not_active Expired
- 1978-04-25 CH CH446378A patent/CH638798A5/de not_active IP Right Cessation
- 1978-04-26 IT IT22729/78A patent/IT1094565B/it active
- 1978-04-26 FI FI781305A patent/FI65996C/fi not_active IP Right Cessation
- 1978-04-26 US US05/900,135 patent/US4161533A/en not_active Expired - Lifetime
- 1978-04-26 IL IL54585A patent/IL54585A/xx unknown
- 1978-04-27 DK DK183678A patent/DK183678A/da not_active Application Discontinuation
- 1978-04-27 NL NL7804558A patent/NL7804558A/xx not_active Application Discontinuation
- 1978-04-27 CA CA302,170A patent/CA1109477A/en not_active Expired
- 1978-04-27 HU HU78HO2068A patent/HU177454B/hu unknown
- 1978-04-27 GB GB16754/78A patent/GB1587105A/en not_active Expired
- 1978-04-27 AT AT0305278A patent/AT363463B/de not_active IP Right Cessation
- 1978-04-27 ZA ZA00782421A patent/ZA782421B/xx unknown
- 1978-04-28 SE SE7804956A patent/SE439012B/sv not_active IP Right Cessation
- 1978-04-28 FR FR7812769A patent/FR2388809A1/fr active Granted
- 1978-04-28 JP JP5220378A patent/JPS53135966A/ja active Pending
- 1978-04-28 BE BE187273A patent/BE866565A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL54585A0 (en) | 1978-07-31 |
| FR2388809B1 (de) | 1980-10-31 |
| FI65996B (fi) | 1984-04-30 |
| IL54585A (en) | 1982-05-31 |
| DE2718871B2 (de) | 1979-10-31 |
| DE2718871A1 (de) | 1978-11-09 |
| ES469058A1 (es) | 1978-11-16 |
| JPS53135966A (en) | 1978-11-28 |
| BE866565A (fr) | 1978-10-30 |
| FR2388809A1 (fr) | 1978-11-24 |
| DK183678A (da) | 1978-10-29 |
| DE2718871C3 (de) | 1980-07-17 |
| GB1587105A (en) | 1981-04-01 |
| ZA782421B (en) | 1979-04-25 |
| CH638798A5 (de) | 1983-10-14 |
| IT7822729A0 (it) | 1978-04-26 |
| HU177454B (en) | 1981-10-28 |
| ATA305278A (de) | 1981-01-15 |
| US4161533A (en) | 1979-07-17 |
| FI65996C (fi) | 1984-08-10 |
| IT1094565B (it) | 1985-08-02 |
| SE7804956L (sv) | 1978-10-29 |
| AT363463B (de) | 1981-08-10 |
| AU3548678A (en) | 1979-11-01 |
| NL7804558A (nl) | 1978-10-31 |
| FI781305A7 (fi) | 1978-10-29 |
| CA1109477A (en) | 1981-09-22 |
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