SU1736339A3 - Способ получени 4-хлор-3-сульфамоилбензойной кислоты - Google Patents
Способ получени 4-хлор-3-сульфамоилбензойной кислоты Download PDFInfo
- Publication number
- SU1736339A3 SU1736339A3 SU884613207A SU4613207A SU1736339A3 SU 1736339 A3 SU1736339 A3 SU 1736339A3 SU 884613207 A SU884613207 A SU 884613207A SU 4613207 A SU4613207 A SU 4613207A SU 1736339 A3 SU1736339 A3 SU 1736339A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- amino
- water
- calculated
- found
- Prior art date
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- FHQAWINGVCDTTG-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl FHQAWINGVCDTTG-UHFFFAOYSA-N 0.000 title claims abstract 3
- 238000000034 method Methods 0.000 title claims description 68
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 123
- 229910001868 water Inorganic materials 0.000 claims description 122
- -1 -``C ^ -alkyl Chemical compound 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000002474 experimental method Methods 0.000 claims description 8
- 230000036772 blood pressure Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
- 229960003883 furosemide Drugs 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 1
- NSIKFNOYIGGILA-UHFFFAOYSA-N [Na].[Na].[K] Chemical compound [Na].[Na].[K] NSIKFNOYIGGILA-UHFFFAOYSA-N 0.000 claims 1
- 238000001647 drug administration Methods 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 abstract description 3
- 230000000054 salidiuretic effect Effects 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 239000002934 diuretic Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 3
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
- 238000000354 decomposition reaction Methods 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
- 239000000203 mixture Substances 0.000 description 51
- 238000001953 recrystallisation Methods 0.000 description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
- 239000007858 starting material Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 23
- 239000013078 crystal Substances 0.000 description 23
- 238000001816 cooling Methods 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 229940067157 phenylhydrazine Drugs 0.000 description 12
- 150000001556 benzimidazoles Chemical class 0.000 description 11
- 150000002828 nitro derivatives Chemical class 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 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 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 150000004031 phenylhydrazines Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- SCYSJFKWFQZRJW-UHFFFAOYSA-N 4-chloro-3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC(C(Cl)=O)=CC=C1Cl SCYSJFKWFQZRJW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- DXNYHEAPTKJDNG-UHFFFAOYSA-N C1=CC(=C(C=C1C(=O)N2C3=C(C(=C(C=C3)C(=O)O)N)NC2=S)S(=O)(=O)N)Cl Chemical compound C1=CC(=C(C=C1C(=O)N2C3=C(C(=C(C=C3)C(=O)O)N)NC2=S)S(=O)(=O)N)Cl DXNYHEAPTKJDNG-UHFFFAOYSA-N 0.000 description 3
- IFEBTCXUFUPZLX-UHFFFAOYSA-N ClC1=C(C=C(C(=O)N2C(NC3=C2C=CC(=C3N)C(=O)OC)=S)C=C1)S(N)(=O)=O Chemical compound ClC1=C(C=C(C(=O)N2C(NC3=C2C=CC(=C3N)C(=O)OC)=S)C=C1)S(N)(=O)=O IFEBTCXUFUPZLX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CYGSXHFROXXUIY-UHFFFAOYSA-N methyl 1-amino-2-sulfanylidene-3h-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(N)C(=S)NC2=C1 CYGSXHFROXXUIY-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- YBYCCBHZWDLWSJ-UHFFFAOYSA-N (4-hydrazinyl-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(NN)=CC=C1C(=O)C1=CC=CC=C1 YBYCCBHZWDLWSJ-UHFFFAOYSA-N 0.000 description 2
- AFGPNTWNMKRUJB-UHFFFAOYSA-N 1-[2-amino-3-hydrazinyl-6-(trifluoromethyl)phenyl]ethanone Chemical compound NC1=C(C=CC(=C1C(C)=O)C(F)(F)F)NN AFGPNTWNMKRUJB-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- SCJABUYOESOHGF-UHFFFAOYSA-N 5-[4-amino-2-sulfanylidene-5-(trifluoromethyl)-3H-benzimidazole-1-carbonyl]-2-chlorobenzenesulfonamide Chemical compound ClC1=C(C=C(C(=O)N2C(NC3=C2C=CC(=C3N)C(F)(F)F)=S)C=C1)S(N)(=O)=O SCJABUYOESOHGF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NYJCCGQUMMBDDN-UHFFFAOYSA-N C(=O)=C1C=CC=C2N=C(N=C21)C Chemical compound C(=O)=C1C=CC=C2N=C(N=C21)C NYJCCGQUMMBDDN-UHFFFAOYSA-N 0.000 description 2
- JWDSQJDHDSIISZ-UHFFFAOYSA-N C(C1=CC=CC=C1)SC1=NC2=C(N1C(C1=CC(=C(C=C1)Cl)S(N)(=O)=O)=O)C=CC(=C2N)C(=O)OC Chemical compound C(C1=CC=CC=C1)SC1=NC2=C(N1C(C1=CC(=C(C=C1)Cl)S(N)(=O)=O)=O)C=CC(=C2N)C(=O)OC JWDSQJDHDSIISZ-UHFFFAOYSA-N 0.000 description 2
- DUUJVKDRBZQVTQ-UHFFFAOYSA-N CN(C)C=NS(=O)(=O)C1=CC=CC=C1C(=O)Cl Chemical compound CN(C)C=NS(=O)(=O)C1=CC=CC=C1C(=O)Cl DUUJVKDRBZQVTQ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WJBJSMUUWDXKBR-UHFFFAOYSA-N [2-nitro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O WJBJSMUUWDXKBR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- LGSSUJWAMJGVSV-UHFFFAOYSA-N methyl 1-amino-2-methylbenzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(N)C(C)=NC2=C1 LGSSUJWAMJGVSV-UHFFFAOYSA-N 0.000 description 2
- JLYGQAODBFZSQN-UHFFFAOYSA-N methyl 1-aminobenzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(N)C=NC2=C1 JLYGQAODBFZSQN-UHFFFAOYSA-N 0.000 description 2
- WVJZXSXWSKBYBT-UHFFFAOYSA-N methyl 3-amino-4-[amino-(4-chloro-3-sulfamoylbenzoyl)amino]benzoate Chemical compound NC1=CC(C(=O)OC)=CC=C1N(N)C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 WVJZXSXWSKBYBT-UHFFFAOYSA-N 0.000 description 2
- NWIYFWDJWIGDBG-UHFFFAOYSA-N methyl 4-hydrazinyl-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(NN)C([N+]([O-])=O)=C1 NWIYFWDJWIGDBG-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HQSUQARLCMKGJZ-UHFFFAOYSA-N 1-acetamido-2-methylbenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N(NC(=O)C)C(C)=NC2=C1 HQSUQARLCMKGJZ-UHFFFAOYSA-N 0.000 description 1
- SHSRILYTUGUETN-UHFFFAOYSA-N 1-amino-2-methylbenzimidazole-5-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C2N(N)C(C)=NC2=C1 SHSRILYTUGUETN-UHFFFAOYSA-N 0.000 description 1
- HAVMDTCWDDVLCM-UHFFFAOYSA-N 1-aminobenzimidazole-5-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=C2N(N)C=NC2=C1 HAVMDTCWDDVLCM-UHFFFAOYSA-N 0.000 description 1
- 101150072531 10 gene Proteins 0.000 description 1
- NZJKEQFPRPAEPO-UHFFFAOYSA-N 1h-benzimidazol-4-amine Chemical compound NC1=CC=CC2=C1N=CN2 NZJKEQFPRPAEPO-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- AKHLPGWHBVYDDY-UHFFFAOYSA-N 2-methyl-5-(trifluoromethyl)benzimidazol-1-amine Chemical compound FC(F)(F)C1=CC=C2N(N)C(C)=NC2=C1 AKHLPGWHBVYDDY-UHFFFAOYSA-N 0.000 description 1
- LUEUYMSSSQJYBN-UHFFFAOYSA-N 2-methylbenzimidazol-1-amine Chemical compound C1=CC=C2N(N)C(C)=NC2=C1 LUEUYMSSSQJYBN-UHFFFAOYSA-N 0.000 description 1
- DFBPBBDIJMXVDM-UHFFFAOYSA-N 2-methylsulfanyl-5-(trifluoromethyl)benzimidazol-1-amine Chemical compound FC(F)(F)C1=CC=C2N(N)C(SC)=NC2=C1 DFBPBBDIJMXVDM-UHFFFAOYSA-N 0.000 description 1
- ZSKNGCRQEDFRNJ-UHFFFAOYSA-N 2-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC=CC=C1C(Cl)=O ZSKNGCRQEDFRNJ-UHFFFAOYSA-N 0.000 description 1
- SETOICGVWKYMHQ-UHFFFAOYSA-N 4-(fluoromethyl)benzimidazole-2-thione Chemical compound FCC1=CC=CC2=NC(N=C21)=S SETOICGVWKYMHQ-UHFFFAOYSA-N 0.000 description 1
- IMDASRAMRQJIAA-UHFFFAOYSA-N 4-[acetyl(amino)amino]-3-nitrobenzoic acid Chemical compound CC(=O)N(N)C1=CC=C(C(O)=O)C=C1[N+]([O-])=O IMDASRAMRQJIAA-UHFFFAOYSA-N 0.000 description 1
- SPZGXONNVLTQDE-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 SPZGXONNVLTQDE-UHFFFAOYSA-N 0.000 description 1
- YXTIEPFZXOVXHS-UHFFFAOYSA-N 4-hydrazinyl-3-nitrobenzenesulfonamide Chemical compound NNC1=CC=C(S(N)(=O)=O)C=C1[N+]([O-])=O YXTIEPFZXOVXHS-UHFFFAOYSA-N 0.000 description 1
- SGRPQDRZWGJVTA-UHFFFAOYSA-N 4-hydrazinyl-3-nitrobenzonitrile Chemical compound NNC1=CC=C(C#N)C=C1[N+]([O-])=O SGRPQDRZWGJVTA-UHFFFAOYSA-N 0.000 description 1
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- ZOKIJEBQDZFGMW-PSXMRANNSA-N [(2R)-2-[12-(4-azido-2-nitroanilino)dodecanoyloxy]-3-tetradecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCNc1ccc(cc1[N+]([O-])=O)N=[N+]=[N-] ZOKIJEBQDZFGMW-PSXMRANNSA-N 0.000 description 1
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- VXDSLUMUNWTSDB-UHFFFAOYSA-N acetic acid;chloroform;methanol Chemical compound OC.CC(O)=O.ClC(Cl)Cl VXDSLUMUNWTSDB-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
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- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- HXYXDTAROKJMBO-UHFFFAOYSA-N benzimidazol-1-amine Chemical compound C1=CC=C2N(N)C=NC2=C1 HXYXDTAROKJMBO-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
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- 238000003780 insertion Methods 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RPUAPXNUIBBFOL-UHFFFAOYSA-N methyl 1-acetamidobenzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(NC(C)=O)C=NC2=C1 RPUAPXNUIBBFOL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- INVMSZZCJHMDBL-UHFFFAOYSA-N n-[2-methyl-5-(trifluoromethyl)benzimidazol-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=C2N(NC(=O)C)C(C)=NC2=C1 INVMSZZCJHMDBL-UHFFFAOYSA-N 0.000 description 1
- KYFIBCNAKCLTSS-UHFFFAOYSA-N n-[2-methylsulfanyl-5-(trifluoromethyl)benzimidazol-1-yl]acetamide Chemical compound FC(F)(F)C1=CC=C2N(NC(C)=O)C(SC)=NC2=C1 KYFIBCNAKCLTSS-UHFFFAOYSA-N 0.000 description 1
- ZEMYEQLZOXNOBJ-UHFFFAOYSA-N n-[2-sulfanylidene-5-(trifluoromethyl)-3h-benzimidazol-1-yl]acetamide Chemical compound C1=C(C(F)(F)F)C=C2NC(=S)N(NC(=O)C)C2=C1 ZEMYEQLZOXNOBJ-UHFFFAOYSA-N 0.000 description 1
- IAOLETATTRREPO-UHFFFAOYSA-N n-[5-(trifluoromethyl)benzimidazol-1-yl]formamide Chemical compound FC(F)(F)C1=CC=C2N(NC=O)C=NC2=C1 IAOLETATTRREPO-UHFFFAOYSA-N 0.000 description 1
- YPEBLQOHYWTITR-UHFFFAOYSA-N n-amino-n-[2-amino-4-(trifluoromethyl)phenyl]formamide Chemical compound O=CN(N)C1=CC=C(C(F)(F)F)C=C1N YPEBLQOHYWTITR-UHFFFAOYSA-N 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- SDVHRXOTTYYKRY-UHFFFAOYSA-J tetrasodium;dioxido-oxo-phosphonato-$l^{5}-phosphane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)P([O-])([O-])=O SDVHRXOTTYYKRY-UHFFFAOYSA-J 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/28—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU876131A HU207051B (en) | 1987-12-30 | 1987-12-30 | Process for producing 4-chloro-3-sulfamoylbenzoic acid hydrazides and pharmaceutical compositions comprising such compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1736339A3 true SU1736339A3 (ru) | 1992-05-23 |
Family
ID=10971250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU884613207A SU1736339A3 (ru) | 1987-12-30 | 1988-12-30 | Способ получени 4-хлор-3-сульфамоилбензойной кислоты |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4916149A (enExample) |
| EP (1) | EP0324988B1 (enExample) |
| JP (1) | JPH01213269A (enExample) |
| CN (1) | CN1037336A (enExample) |
| AT (1) | ATE75467T1 (enExample) |
| AU (1) | AU609682B2 (enExample) |
| CA (1) | CA1332739C (enExample) |
| CS (1) | CS277585B6 (enExample) |
| DD (1) | DD283383A5 (enExample) |
| DE (1) | DE3870601D1 (enExample) |
| DK (1) | DK727488A (enExample) |
| ES (1) | ES2034149T3 (enExample) |
| FI (1) | FI886045A7 (enExample) |
| GR (1) | GR3004471T3 (enExample) |
| HU (1) | HU207051B (enExample) |
| IE (1) | IE63246B1 (enExample) |
| IL (1) | IL88735A (enExample) |
| NO (1) | NO172285C (enExample) |
| NZ (1) | NZ227481A (enExample) |
| PH (1) | PH25739A (enExample) |
| PL (2) | PL157971B1 (enExample) |
| PT (1) | PT89368B (enExample) |
| RU (2) | RU1838303C (enExample) |
| SU (1) | SU1736339A3 (enExample) |
| UA (1) | UA19123A (enExample) |
| YU (1) | YU47125B (enExample) |
| ZA (1) | ZA889729B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69220050T2 (de) * | 1991-04-01 | 1998-01-22 | Univ Duke | Verfahren zur inhibierung der fibrose |
| FR2708608B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés de N-sulfonylbenzimidazolone, leur préparation, les compositions pharmaceutiques en contenant. |
| DE10132896A1 (de) * | 2001-07-06 | 2003-01-16 | Bayer Cropscience Ag | Heterocyclische Amidderivate |
| DE102005002130A1 (de) * | 2005-01-17 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte N-Aminomethylensulfonamide, ihre Herstellung und Verwendung als Arzneimittel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1122541B (de) * | 1959-12-28 | 1962-01-25 | Hoechst Ag | Verfahren zur Herstellung von Sulfamyl-anthranilsaeuren |
| DE1158927B (de) * | 1961-09-15 | 1963-12-12 | Werner Rahms | Grubenstempel |
| DE2144908C2 (de) * | 1971-09-08 | 1982-12-09 | Hoechst Ag, 6000 Frankfurt | 5-(3- oder 4-Aminobenzolsulfonylamino)-benzimidazolone-(2) und Verfahren zu ihrer Herstellung |
| BE793718A (fr) * | 1972-01-07 | 1973-07-05 | Merck & Co Inc | Aminobenzimidazoles |
| DE2247828A1 (de) * | 1972-09-29 | 1974-04-04 | Hoechst Ag | Sulfamoyl-anthranilsaeuren und verfahren zu ihrer herstellung |
| US4420487A (en) * | 1978-04-10 | 1983-12-13 | The Purdue Frederick Company | Diuretic and antihypertensive benzimidazoles |
-
1987
- 1987-12-30 HU HU876131A patent/HU207051B/hu not_active IP Right Cessation
-
1988
- 1988-12-20 IL IL88735A patent/IL88735A/xx not_active IP Right Cessation
- 1988-12-22 NZ NZ227481A patent/NZ227481A/en unknown
- 1988-12-23 DD DD88323775A patent/DD283383A5/de not_active IP Right Cessation
- 1988-12-28 PH PH37991A patent/PH25739A/en unknown
- 1988-12-29 US US07/295,925 patent/US4916149A/en not_active Expired - Fee Related
- 1988-12-29 CA CA000587184A patent/CA1332739C/en not_active Expired - Fee Related
- 1988-12-29 DK DK727488A patent/DK727488A/da not_active Application Discontinuation
- 1988-12-29 JP JP63335692A patent/JPH01213269A/ja active Pending
- 1988-12-29 ZA ZA889729A patent/ZA889729B/xx unknown
- 1988-12-30 FI FI886045A patent/FI886045A7/fi not_active Application Discontinuation
- 1988-12-30 UA UA4613207A patent/UA19123A/uk unknown
- 1988-12-30 ES ES198888121901T patent/ES2034149T3/es not_active Expired - Lifetime
- 1988-12-30 AT AT88121901T patent/ATE75467T1/de not_active IP Right Cessation
- 1988-12-30 YU YU240188A patent/YU47125B/sh unknown
- 1988-12-30 EP EP88121901A patent/EP0324988B1/de not_active Expired - Lifetime
- 1988-12-30 PL PL1988276889A patent/PL157971B1/pl unknown
- 1988-12-30 CS CS889108A patent/CS277585B6/cs unknown
- 1988-12-30 CN CN88108996A patent/CN1037336A/zh active Pending
- 1988-12-30 AU AU27631/88A patent/AU609682B2/en not_active Ceased
- 1988-12-30 NO NO885830A patent/NO172285C/no unknown
- 1988-12-30 PL PL1988282492A patent/PL158049B1/pl unknown
- 1988-12-30 PT PT89368A patent/PT89368B/pt not_active IP Right Cessation
- 1988-12-30 DE DE8888121901T patent/DE3870601D1/de not_active Expired - Lifetime
- 1988-12-30 SU SU884613207A patent/SU1736339A3/ru active
- 1988-12-30 IE IE389288A patent/IE63246B1/en not_active IP Right Cessation
-
1989
- 1989-05-10 RU SU894613991A patent/RU1838303C/ru active
- 1989-10-20 RU SU894742151A patent/RU1830064C/ru active
-
1992
- 1992-04-30 GR GR920400738T patent/GR3004471T3/el unknown
Non-Patent Citations (1)
| Title |
|---|
| Бюллер К., Пирсон А. Органические синтезы, - М,: Мир, 1973, ч.1, с. 504. * |
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