FI65996C - Foerfarande foer framstaellning av terapeutiskt anvaendbara n-2-furylmetyl)-5-sulfamoyl-ortanilsyror och deras salter - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara n-2-furylmetyl)-5-sulfamoyl-ortanilsyror och deras salter Download PDFInfo
- Publication number
- FI65996C FI65996C FI781305A FI781305A FI65996C FI 65996 C FI65996 C FI 65996C FI 781305 A FI781305 A FI 781305A FI 781305 A FI781305 A FI 781305A FI 65996 C FI65996 C FI 65996C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- acid
- sulfamoyl
- group
- furylmethyl
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 235000016709 nutrition Nutrition 0.000 title 1
- -1 2-furylmethyl Chemical group 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000565 sulfonamide group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 1
- 229940085942 formulation r Drugs 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000012467 final product Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 238000007127 saponification reaction Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000012043 crude product Substances 0.000 description 4
- 229940072033 potash Drugs 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002989 phenols Chemical class 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
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 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
- 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 238000007192 Meerwein reaction reaction Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 238000009835 boiling Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 125000002130 sulfonic acid ester group Chemical group 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
- VPFATWYQUWGNHG-UHFFFAOYSA-N (4-methylphenyl) 2-chloro-4-(3-methoxyphenoxy)-5-sulfamoylbenzenesulfonate Chemical compound COC1=CC=CC(OC=2C(=CC(=C(Cl)C=2)S(=O)(=O)OC=2C=CC(C)=CC=2)S(N)(=O)=O)=C1 VPFATWYQUWGNHG-UHFFFAOYSA-N 0.000 description 1
- KGDRBQKYIOQYFG-UHFFFAOYSA-N (4-methylphenyl) 2-chloro-4-(4-methoxyphenoxy)-5-sulfamoylbenzenesulfonate Chemical compound C1=CC(OC)=CC=C1OC1=CC(Cl)=C(S(=O)(=O)OC=2C=CC(C)=CC=2)C=C1S(N)(=O)=O KGDRBQKYIOQYFG-UHFFFAOYSA-N 0.000 description 1
- 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 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
- DYLDHQUUQHWKJQ-UHFFFAOYSA-N (4-methylphenyl) 2-chloro-4-phenoxy-5-sulfamoylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C(C(=C1)Cl)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 DYLDHQUUQHWKJQ-UHFFFAOYSA-N 0.000 description 1
- NIAJGDJSTGZLGE-UHFFFAOYSA-N (4-methylphenyl) 3-(furan-2-ylmethylsulfamoyl)-4-(4-methoxyphenoxy)benzenesulfonate Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(S(=O)(=O)OC=2C=CC(C)=CC=2)C=C1S(=O)(=O)NCC1=CC=CO1 NIAJGDJSTGZLGE-UHFFFAOYSA-N 0.000 description 1
- RQYYUHGXOAMYAL-UHFFFAOYSA-N (4-methylphenyl) benzenesulfonate Chemical compound C1=CC(C)=CC=C1OS(=O)(=O)C1=CC=CC=C1 RQYYUHGXOAMYAL-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
- 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 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- FUTPMPLOSINGPM-UHFFFAOYSA-N 2-chloro-4-(4-methoxyphenoxy)-5-sulfamoylbenzenesulfonic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC(Cl)=C(S(O)(=O)=O)C=C1S(N)(=O)=O FUTPMPLOSINGPM-UHFFFAOYSA-N 0.000 description 1
- SSHOJTSOZBIOQR-UHFFFAOYSA-N 2-chloro-4-methyl-5-sulfamoylbenzenesulfonyl chloride Chemical compound CC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1S(N)(=O)=O SSHOJTSOZBIOQR-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
- DNZIWTIEBNEXOF-UHFFFAOYSA-N 4,6-dichlorobenzene-1,3-disulfonyl chloride Chemical compound ClC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O DNZIWTIEBNEXOF-UHFFFAOYSA-N 0.000 description 1
- LZJVSPPXXGXGQL-UHFFFAOYSA-N 4-aminobenzenecarbothioamide Chemical compound NC(=S)C1=CC=C(N)C=C1 LZJVSPPXXGXGQL-UHFFFAOYSA-N 0.000 description 1
- KEMFBYOXSKBPQJ-UHFFFAOYSA-N 4-chloro-2-fluoro-5-sulfamoylbenzenesulfonyl chloride Chemical compound NS(=O)(=O)C1=CC(S(Cl)(=O)=O)=C(F)C=C1Cl KEMFBYOXSKBPQJ-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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- IIJDXHMJDARPNZ-UHFFFAOYSA-N CC1=CC(=CC=C1)OC2=C(C=CC(=C2)Cl)S(=O)(=O)N Chemical compound CC1=CC(=CC=C1)OC2=C(C=CC(=C2)Cl)S(=O)(=O)N IIJDXHMJDARPNZ-UHFFFAOYSA-N 0.000 description 1
- XQDCMDNVAIMTPP-UHFFFAOYSA-N CC1=CC=C(C=C1)OS(=O)(=O)C2=CC=CC=C2S(=O)(=O)N Chemical compound CC1=CC=C(C=C1)OS(=O)(=O)C2=CC=CC=C2S(=O)(=O)N XQDCMDNVAIMTPP-UHFFFAOYSA-N 0.000 description 1
- PXJZDCOIELZHSD-UHFFFAOYSA-N CN(C)C=NS(=O)(=O)C1=CC([N+]([O-])=O)=C(F)C=C1Cl Chemical compound CN(C)C=NS(=O)(=O)C1=CC([N+]([O-])=O)=C(F)C=C1Cl PXJZDCOIELZHSD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 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
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-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
- 241001494479 Pecora Species 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
- 241000277284 Salvelinus fontinalis Species 0.000 description 1
- ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- XBAZKKKXWIIRGN-UHFFFAOYSA-N aminomethanesulfonimidic acid Chemical compound NCS(N)(=O)=O XBAZKKKXWIIRGN-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QFWSIJKSJPEHCF-BTVCFUMJSA-N azane;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical class N.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O QFWSIJKSJPEHCF-BTVCFUMJSA-N 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
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229950011260 betanaphthol Drugs 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
- 210000004556 brain Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 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
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229960001614 levamisole Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 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
- RGUOJYYIMVSCNC-UHFFFAOYSA-N n,n-dimethylformamide;2-methylpropanoic acid Chemical compound CN(C)C=O.CC(C)C(O)=O RGUOJYYIMVSCNC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- 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
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 230000000580 secretagogue 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
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (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 (2)
| 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 |
| DE2718871 | 1977-04-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI781305A7 FI781305A7 (fi) | 1978-10-29 |
| FI65996B FI65996B (fi) | 1984-04-30 |
| FI65996C true FI65996C (fi) | 1984-08-10 |
Family
ID=6007484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI781305A FI65996C (fi) | 1977-04-28 | 1978-04-26 | Foerfarande foer framstaellning av terapeutiskt anvaendbara n-2-furylmetyl)-5-sulfamoyl-ortanilsyror och deras salter |
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 |
| MXPA06008612A (es) * | 2004-02-20 | 2007-01-25 | Aventis Pharma Inc | Derivados de furosemida como modulares de hm74 y su uso para el tratamiento de la inflamacion. |
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 FI FI781305A patent/FI65996C/fi not_active IP Right Cessation
- 1978-04-26 IL IL54585A patent/IL54585A/xx unknown
- 1978-04-26 IT IT22729/78A patent/IT1094565B/it active
- 1978-04-26 US US05/900,135 patent/US4161533A/en not_active Expired - Lifetime
- 1978-04-27 AT AT0305278A patent/AT363463B/de not_active IP Right Cessation
- 1978-04-27 CA CA302,170A patent/CA1109477A/en not_active Expired
- 1978-04-27 GB GB16754/78A patent/GB1587105A/en not_active Expired
- 1978-04-27 NL NL7804558A patent/NL7804558A/xx not_active Application Discontinuation
- 1978-04-27 HU HU78HO2068A patent/HU177454B/hu unknown
- 1978-04-27 DK DK183678A patent/DK183678A/da not_active Application Discontinuation
- 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 BE BE187273A patent/BE866565A/xx 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
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53135966A (en) | 1978-11-28 |
| AU3548678A (en) | 1979-11-01 |
| IT7822729A0 (it) | 1978-04-26 |
| IL54585A0 (en) | 1978-07-31 |
| US4161533A (en) | 1979-07-17 |
| FI781305A7 (fi) | 1978-10-29 |
| DE2718871C3 (de) | 1980-07-17 |
| BE866565A (fr) | 1978-10-30 |
| GB1587105A (en) | 1981-04-01 |
| FR2388809B1 (de) | 1980-10-31 |
| IT1094565B (it) | 1985-08-02 |
| DE2718871A1 (de) | 1978-11-09 |
| CA1109477A (en) | 1981-09-22 |
| DK183678A (da) | 1978-10-29 |
| NL7804558A (nl) | 1978-10-31 |
| SE7804956L (sv) | 1978-10-29 |
| AT363463B (de) | 1981-08-10 |
| CH638798A5 (de) | 1983-10-14 |
| IL54585A (en) | 1982-05-31 |
| SE439012B (sv) | 1985-05-28 |
| ATA305278A (de) | 1981-01-15 |
| FI65996B (fi) | 1984-04-30 |
| FR2388809A1 (fr) | 1978-11-24 |
| DE2718871B2 (de) | 1979-10-31 |
| ES469058A1 (es) | 1978-11-16 |
| HU177454B (en) | 1981-10-28 |
| ZA782421B (en) | 1979-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: HOECHST AKTIENGESELLSCHAFT |