CN1037336A - 新型4-氯-3-氨磺酰苯甲酰肼-制备方法，含此化合物的药物组分及其医疗用途 - Google Patents
新型4-氯-3-氨磺酰苯甲酰肼-制备方法，含此化合物的药物组分及其医疗用途 Download PDFInfo
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- CN1037336A CN1037336A CN88108996A CN88108996A CN1037336A CN 1037336 A CN1037336 A CN 1037336A CN 88108996 A CN88108996 A CN 88108996A CN 88108996 A CN88108996 A CN 88108996A CN 1037336 A CN1037336 A CN 1037336A
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- amino
- chloro
- benzoyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 81
- 238000002360 preparation method Methods 0.000 title claims abstract description 51
- -1 4-chloro-3-sulfamoylbenzoyl Chemical group 0.000 title claims abstract description 49
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 208000004880 Polyuria Diseases 0.000 claims abstract description 13
- 230000035619 diuresis Effects 0.000 claims abstract description 13
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 68
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 37
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 14
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 9
- 235000019253 formic acid Nutrition 0.000 claims description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 8
- NPRDCBPQJNOEMW-UHFFFAOYSA-N aniline;hydrazine Chemical class NN.NC1=CC=CC=C1 NPRDCBPQJNOEMW-UHFFFAOYSA-N 0.000 claims description 8
- 230000001882 diuretic effect Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- SFMSVSNKGFIDAB-UHFFFAOYSA-N aniline;1h-benzimidazole Chemical class NC1=CC=CC=C1.C1=CC=C2NC=NC2=C1 SFMSVSNKGFIDAB-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- DEDYHNROLBPTDJ-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanyl)-1h-benzimidazole Chemical class C1=CC=C2NC(SC=3NC4=CC=CC=C4N=3)=NC2=C1 DEDYHNROLBPTDJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 230000002349 favourable effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- 229910001868 water Inorganic materials 0.000 description 83
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
- 238000000354 decomposition reaction Methods 0.000 description 56
- 238000000967 suction filtration Methods 0.000 description 55
- 238000005406 washing Methods 0.000 description 52
- 238000001953 recrystallisation Methods 0.000 description 50
- 239000002994 raw material Substances 0.000 description 48
- 238000001035 drying Methods 0.000 description 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- 229940067157 phenylhydrazine Drugs 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 206010013786 Dry skin Diseases 0.000 description 31
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000011259 mixed solution Substances 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 23
- 238000001816 cooling Methods 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 229960004756 ethanol Drugs 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 238000013019 agitation Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 238000009834 vaporization Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 229960000935 dehydrated alcohol Drugs 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 150000002828 nitro derivatives Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 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 description 9
- 229960003883 furosemide Drugs 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 238000011161 development Methods 0.000 description 8
- 230000018109 developmental process Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 241001597008 Nomeidae Species 0.000 description 7
- 239000003513 alkali Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
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- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 4
- GJSYEHWZILYZBH-UHFFFAOYSA-N C(C)(=O)NC1(C(C=CC=C1)O)[As](O)(O)=O Chemical compound C(C)(=O)NC1(C(C=CC=C1)O)[As](O)(O)=O GJSYEHWZILYZBH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
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- 238000005660 chlorination reaction Methods 0.000 description 4
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- 230000008025 crystallization Effects 0.000 description 4
- WHVPFOLJDWVLSZ-UHFFFAOYSA-N methyl 2-amino-3h-benzimidazole-5-carboxylate Chemical class COC(=O)C1=CC=C2N=C(N)NC2=C1 WHVPFOLJDWVLSZ-UHFFFAOYSA-N 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 229910000564 Raney nickel Inorganic materials 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GDLBFKVLRPITMI-UHFFFAOYSA-N diazoxide Chemical compound ClC1=CC=C2NC(C)=NS(=O)(=O)C2=C1 GDLBFKVLRPITMI-UHFFFAOYSA-N 0.000 description 3
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- 238000010253 intravenous injection Methods 0.000 description 3
- 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 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 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
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- QNBMELTXPLGIMF-UHFFFAOYSA-N 2-amino-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(N)=NC2=C1 QNBMELTXPLGIMF-UHFFFAOYSA-N 0.000 description 2
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- JLYGQAODBFZSQN-UHFFFAOYSA-N methyl 1-aminobenzimidazole-5-carboxylate Chemical class COC(=O)C1=CC=C2N(N)C=NC2=C1 JLYGQAODBFZSQN-UHFFFAOYSA-N 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
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- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- YBDBYPQFIMSFJW-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)-phenylmethanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 YBDBYPQFIMSFJW-UHFFFAOYSA-N 0.000 description 1
- ITGMYWCBISPNSC-UHFFFAOYSA-N (4-methylsulfonyl-2-nitrophenyl)hydrazine Chemical compound CS(=O)(=O)C1=CC=C(NN)C([N+]([O-])=O)=C1 ITGMYWCBISPNSC-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- JAANTSGNTKWLFA-UHFFFAOYSA-N 1-chloro-4-methylsulfonyl-2-nitrobenzene Chemical compound CS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 JAANTSGNTKWLFA-UHFFFAOYSA-N 0.000 description 1
- RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- JCCBZCMSYUSCFM-UHFFFAOYSA-N 2-chlorobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1Cl JCCBZCMSYUSCFM-UHFFFAOYSA-N 0.000 description 1
- MXJRRPABGUWERH-UHFFFAOYSA-N 2-methyl-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1=C(C(F)(F)F)C=C2NC(C)=NC2=C1 MXJRRPABGUWERH-UHFFFAOYSA-N 0.000 description 1
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 1
- NLTIAFOPZHZEPC-UHFFFAOYSA-N 4-[(5-chloropyridin-2-yl)amino]-2-phenyl-4-(trifluoromethyl)-1h-imidazol-5-one Chemical compound N1=C(C=2C=CC=CC=2)NC(=O)C1(C(F)(F)F)NC1=CC=C(Cl)C=N1 NLTIAFOPZHZEPC-UHFFFAOYSA-N 0.000 description 1
- PROWOAXUHUCPJB-UHFFFAOYSA-N 4-[amino-(4-chloro-3-sulfamoylbenzoyl)amino]-3-nitrobenzoic acid Chemical compound C=1C=C(C(O)=O)C=C([N+]([O-])=O)C=1N(N)C(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 PROWOAXUHUCPJB-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
- 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 1
- LBXHRAWDUMTPSE-AOOOYVTPSA-N 4-chloro-N-[(2S,6R)-2,6-dimethyl-1-piperidinyl]-3-sulfamoylbenzamide Chemical compound C[C@H]1CCC[C@@H](C)N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 LBXHRAWDUMTPSE-AOOOYVTPSA-N 0.000 description 1
- REQFWARMBJWJAQ-UHFFFAOYSA-N 4-chloro-n-methyl-3-(methylsulfamoyl)benzamide Chemical compound CNC(=O)C1=CC=C(Cl)C(S(=O)(=O)NC)=C1 REQFWARMBJWJAQ-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
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AEVOOIYFJVOWGS-UHFFFAOYSA-N CC=1NC2=C(N1)C=CC(=C2N)C(=O)O Chemical compound CC=1NC2=C(N1)C=CC(=C2N)C(=O)O AEVOOIYFJVOWGS-UHFFFAOYSA-N 0.000 description 1
- PDYAHTOUKNYQKU-UHFFFAOYSA-N COC(=O)C1=C(C2=NC(=O)N=C2C=C1)N Chemical compound COC(=O)C1=C(C2=NC(=O)N=C2C=C1)N PDYAHTOUKNYQKU-UHFFFAOYSA-N 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- UUDJQZPFEDJRMU-UHFFFAOYSA-N NC=NS(=O)=O Chemical compound NC=NS(=O)=O UUDJQZPFEDJRMU-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- NSIKFNOYIGGILA-UHFFFAOYSA-N [Na].[Na].[K] Chemical compound [Na].[Na].[K] NSIKFNOYIGGILA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000010241 blood sampling Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960004070 clopamide Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- MMBDAJMDNVQFDV-UHFFFAOYSA-N methyl n-[amino(methylsulfanyl)methylidene]carbamate Chemical compound COC(=O)N=C(N)SC MMBDAJMDNVQFDV-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QMYNOAIGZPUBAQ-UHFFFAOYSA-N n-[(5-chloropyridin-2-yl)carbamothioyl]-2-methyl-3-nitrobenzamide Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1C(=O)NC(=S)NC1=CC=C(Cl)C=N1 QMYNOAIGZPUBAQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 210000002640 perineum Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Images
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 (2)
| 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 |
| HU6131/87 | 1987-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1037336A true CN1037336A (zh) | 1989-11-22 |
Family
ID=10971250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88108996A Pending CN1037336A (zh) | 1987-12-30 | 1988-12-30 | 新型4-氯-3-氨磺酰苯甲酰肼-制备方法，含此化合物的药物组分及其医疗用途 |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100374424C (zh) * | 2001-07-06 | 2008-03-12 | 拜尔农作物科学股份公司 | 杂环酰胺衍生物和其用途 |
Families Citing this family (3)
| 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. |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100374424C (zh) * | 2001-07-06 | 2008-03-12 | 拜尔农作物科学股份公司 | 杂环酰胺衍生物和其用途 |
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