CH665417A5 - Derives du benzimidazole, procede pour leur preparation et agents anti-ulceres contenant ces derives. - Google Patents

Derives du benzimidazole, procede pour leur preparation et agents anti-ulceres contenant ces derives. Download PDF

Info

Publication number: CH665417A5
Authority: CH; Switzerland
Prior art keywords: compound; benzimidazole; nmr; hydrogen atom; formula
Prior art date: 1984-08-31

Application number

CH3709/85A

Other languages

English (en)

French (fr)

Inventor

Susumu Okabe

Masaru Satoh

Tomio Yamakawa

Yutaka Nomura

Masatoshi Hayashi

Original Assignee

Nippon Chemiphar Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-08-31

Filing date

1985-08-29

Publication date

1988-05-13

1984-08-31 Priority claimed from JP59182400A external-priority patent/JPS6160660A/ja

1985-03-26 Priority claimed from JP60061194A external-priority patent/JPH068283B2/ja

1985-03-26 Priority claimed from JP60061195A external-priority patent/JPH0764826B2/ja

1985-08-29 Application filed by Nippon Chemiphar Co filed Critical Nippon Chemiphar Co

1988-05-13 Publication of CH665417A5 publication Critical patent/CH665417A5/fr

Links

150000001556 benzimidazoles Chemical class 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 12
239000003699 antiulcer agent Substances 0.000 title claims description 6
229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
238000005481 NMR spectroscopy Methods 0.000 description 40
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000013078 crystal Substances 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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230000002829 reductive effect Effects 0.000 description 21
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235000019441 ethanol Nutrition 0.000 description 19
239000002904 solvent Substances 0.000 description 19
239000007832 Na2SO4 Substances 0.000 description 17
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229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
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108091006112 ATPases Proteins 0.000 description 8
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CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 8
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
IJINDUSMSVDESS-UHFFFAOYSA-N 2-benzylsulfanyl-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=C1 IJINDUSMSVDESS-UHFFFAOYSA-N 0.000 description 3
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MCVNBNZGDZWNML-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 MCVNBNZGDZWNML-UHFFFAOYSA-N 0.000 description 2
VSLKTMFOYIAAKO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n-methylaniline Chemical compound CNC1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 VSLKTMFOYIAAKO-UHFFFAOYSA-N 0.000 description 2
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DVCQNMAKXHNXAH-UHFFFAOYSA-N n,n-dimethyl-2-[(4-methyl-1h-benzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=C(C)C=CC=C2N1 DVCQNMAKXHNXAH-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
FARSPAVQUKTXLF-UHFFFAOYSA-N 1h-benzimidazol-1-ium;chloride Chemical compound Cl.C1=CC=C2NC=NC2=C1 FARSPAVQUKTXLF-UHFFFAOYSA-N 0.000 description 1
KYHVRYDRJGJTLD-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfanylmethyl)aniline hydrochloride Chemical compound Cl.NC1=C(CSC=2NC3=C(N2)C=CC=C3)C=CC=C1 KYHVRYDRJGJTLD-UHFFFAOYSA-N 0.000 description 1
YXJVOOMBCUXMAO-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1CS(=O)C1=NC2=CC=CC=C2N1 YXJVOOMBCUXMAO-UHFFFAOYSA-N 0.000 description 1
PSXUBLNOGFVJRX-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 PSXUBLNOGFVJRX-UHFFFAOYSA-N 0.000 description 1
DSKOIZNBFDCVAN-UHFFFAOYSA-N 2-(chloromethyl)-N,N,3-trimethylaniline hydrochloride Chemical compound Cl.CN(C1=C(CCl)C(=CC=C1)C)C DSKOIZNBFDCVAN-UHFFFAOYSA-N 0.000 description 1
WZRAHSJIMVVFIE-UHFFFAOYSA-N 2-(chloromethyl)-n,n-diethylaniline;hydrochloride Chemical compound Cl.CCN(CC)C1=CC=CC=C1CCl WZRAHSJIMVVFIE-UHFFFAOYSA-N 0.000 description 1
JFJQMUQRTCGSFC-UHFFFAOYSA-N 2-(chloromethyl)aniline Chemical compound NC1=CC=CC=C1CCl JFJQMUQRTCGSFC-UHFFFAOYSA-N 0.000 description 1
CBPUCSYOOOKPCR-UHFFFAOYSA-N 2-[(2-methylphenyl)methylsulfanyl]-1h-benzimidazole Chemical compound CC1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 CBPUCSYOOOKPCR-UHFFFAOYSA-N 0.000 description 1
ICJZQAGBAOZSTB-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC1=CC=CC=C1N(C)C ICJZQAGBAOZSTB-UHFFFAOYSA-N 0.000 description 1
XEACPNJGCWYTPJ-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=CC=CC=C1N(C)C XEACPNJGCWYTPJ-UHFFFAOYSA-N 0.000 description 1
UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
108010074725 Alpha,alpha-trehalose phosphorylase Proteins 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ODHNXQJZUIGFMP-UHFFFAOYSA-N Cl.CNC1=C(CSC=2NC3=C(N2)C=CC=C3)C=CC=C1 Chemical compound Cl.CNC1=C(CSC=2NC3=C(N2)C=CC=C3)C=CC=C1 ODHNXQJZUIGFMP-UHFFFAOYSA-N 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
229920001917 Ficoll Polymers 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
241001433070 Xiphoides Species 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
ZULJYVVAYGFYKU-UHFFFAOYSA-N acetonitrile;chloroform Chemical compound CC#N.ClC(Cl)Cl ZULJYVVAYGFYKU-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 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
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
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
229940080428 lactose 200 mg Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
108091028838 miR-2 stem-loop Proteins 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 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
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004448 titration Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
210000002417 xiphoid bone Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- 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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH3709/85A 1984-08-31 1985-08-29 Derives du benzimidazole, procede pour leur preparation et agents anti-ulceres contenant ces derives. CH665417A5 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP59182400A JPS6160660A (ja)	1984-08-31	1984-08-31	ベンズイミダゾ−ル誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JP60061194A JPH068283B2 (ja)	1985-03-26	1985-03-26	ベンズイミダゾ−ル誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JP60061195A JPH0764826B2 (ja)	1985-03-26	1985-03-26	ベンズイミダゾール誘導体

Publications (1)

Publication Number	Publication Date
CH665417A5 true CH665417A5 (fr)	1988-05-13

Family

ID=27297422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3709/85A CH665417A5 (fr)	1984-08-31	1985-08-29	Derives du benzimidazole, procede pour leur preparation et agents anti-ulceres contenant ces derives.

Country Status (14)

Country	Link
KR (1)	KR920004936B1 (it)
AR (1)	AR242195A1 (it)
AU (3)	AU4640985A (it)
BE (1)	BE903128A (it)
BR (1)	BR8504252A (it)
CH (1)	CH665417A5 (it)
DE (1)	DE3531487C2 (it)
ES (1)	ES8703142A1 (it)
FR (1)	FR2569691B1 (it)
GB (1)	GB2163747B (it)
IT (1)	IT1189601B (it)
MX (1)	MX159807A (it)
NL (1)	NL8502384A (it)
SE (1)	SE500669C2 (it)

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EP0251536A1 (en) *	1986-06-24	1988-01-07	FISONS plc	Benzimidazoles, their production, formulation and use as gastric acid secretion inhibitors
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DE3639926A1 (de) *	1986-11-22	1988-06-01	Hoechst Ag	Substituierte thienoimidazoltoluidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer
IT1222412B (it) *	1987-07-31	1990-09-05	Chiesi Farma Spa	Tiometil e sulfinil metil derivati ad azione antisecretiva acida gastrica,loro procedimento di preparazione e composizioni farmaceutiche che li contengono
JP2614756B2 (ja) *	1988-08-10	1997-05-28	日本ケミファ株式会社	イミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
JPH06298611A (ja) *	1993-04-16	1994-10-25	Nippon Chemiphar Co Ltd	抗菌剤
SE9301489D0 (sv)	1993-04-30	1993-04-30	Ab Astra	Veterinary composition
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HRP960232A2 (en) *	1995-07-03	1998-02-28	Astra Ab	A process for the optical purification of compounds
CN1093855C (zh) *	1995-09-21	2002-11-06	帕斯医药股份有限公司	新的含有对酸不稳定的奥美拉唑的组合物及其制备方法
SE9600070D0 (sv)	1996-01-08	1996-01-08	Astra Ab	New oral pharmaceutical dosage forms
US6380222B2 (en)	1996-10-11	2002-04-30	Astrazeneca Ab	Use of an H+, K+-atpase inhibitor in the treatment of nasal polyps
US6303644B1 (en)	1997-07-25	2001-10-16	Byk Gulden Lomberg Chemische Fabrik Gmbh	Proton pump inhibitor in therapeutic combination with antibacterial substances
SE9704870D0 (sv)	1997-12-22	1997-12-22	Astra Ab	New pharmaceutical formulation I
SE9704869D0 (sv) *	1997-12-22	1997-12-22	Astra Ab	New pharmaceutical formulaton II
WO2000009092A1 (en)	1998-08-12	2000-02-24	Byk Gulden Lomberg Chemische Fabrik Gmbh	Oral administration form for pyridin-2-ylmethylsulfinyl-1h-benzimidazoles
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TWI243672B (en)	1999-06-01	2005-11-21	Astrazeneca Ab	New use of compounds as antibacterial agents
JP4980527B2 (ja)	1999-06-07	2012-07-18	ニコメッドゲゼルシャフトミットベシュレンクテルハフツング	酸に不安定な活性化合物を含有する新規の製剤および投与形
SE9903831D0 (sv)	1999-10-22	1999-10-22	Astra Ab	Formulation of substituted benzimidazoles
SE0000774D0 (sv)	2000-03-08	2000-03-08	Astrazeneca Ab	New formulation
US6544556B1 (en)	2000-09-11	2003-04-08	Andrx Corporation	Pharmaceutical formulations containing a non-steroidal antiinflammatory drug and a proton pump inhibitor
SE0101379D0 (sv)	2001-04-18	2001-04-18	Diabact Ab	Komposition som hämmar utsöndring av magsyra
US8206741B2 (en)	2001-06-01	2012-06-26	Pozen Inc.	Pharmaceutical compositions for the coordinated delivery of NSAIDs
SE0102993D0 (sv)	2001-09-07	2001-09-07	Astrazeneca Ab	New self emulsifying drug delivery system
US8101209B2 (en)	2001-10-09	2012-01-24	Flamel Technologies	Microparticulate oral galenical form for the delayed and controlled release of pharmaceutical active principles
MXPA04009968A (es)	2002-04-09	2004-12-13	Flamel Tech Sa	Formulacion farmaceutica oral bajo forma de suspension acuosa de microcapsulas que permiten la liberacion modificada de principio (s) activo (s).
DE60323474D1 (de)	2002-04-09	2008-10-23	Flamel Tech Sa	Orale pharmazeutische formulierung in form einer wässrigen suspension von mikrokapseln zur modifizierten freisetzung von amoxicillin
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1985
- 1985-08-19 AU AU46409/85A patent/AU4640985A/en not_active Abandoned
- 1985-08-27 ES ES546445A patent/ES8703142A1/es not_active Expired
- 1985-08-27 BE BE0/215506A patent/BE903128A/fr not_active IP Right Cessation
- 1985-08-29 CH CH3709/85A patent/CH665417A5/fr not_active IP Right Cessation
- 1985-08-29 GB GB08521493A patent/GB2163747B/en not_active Expired
- 1985-08-30 NL NL8502384A patent/NL8502384A/nl not_active Application Discontinuation
- 1985-08-30 IT IT67743/85A patent/IT1189601B/it active
- 1985-08-30 MX MX206462A patent/MX159807A/es unknown
- 1985-08-30 BR BR8504252A patent/BR8504252A/pt unknown
- 1985-08-30 KR KR1019850006307A patent/KR920004936B1/ko not_active Expired
- 1985-08-30 FR FR858512961A patent/FR2569691B1/fr not_active Expired
- 1985-08-30 AR AR85301474A patent/AR242195A1/es active
- 1985-08-30 SE SE8504048A patent/SE500669C2/sv unknown
- 1985-08-30 DE DE3531487A patent/DE3531487C2/de not_active Expired - Fee Related
1989
- 1989-09-11 AU AU41271/89A patent/AU4127189A/en not_active Abandoned
1992
- 1992-11-27 AU AU29750/92A patent/AU647978B2/en not_active Ceased

Also Published As

Publication number	Publication date
AU2975092A (en)	1993-01-28
BE903128A (fr)	1985-12-16
GB2163747A (en)	1986-03-05
FR2569691A1 (fr)	1986-03-07
GB8521493D0 (en)	1985-10-02
BR8504252A (pt)	1986-06-17
AU4640985A (en)	1986-03-06
GB2163747B (en)	1989-02-08
AU4127189A (en)	1989-12-21
DE3531487C2 (de)	1995-08-17
SE8504048L (sv)	1986-03-01
KR860001793A (ko)	1986-03-22
ES546445A0 (es)	1986-11-16
AR242195A1 (es)	1993-03-31
KR920004936B1 (ko)	1992-06-22
IT8567743A0 (it)	1985-08-30
FR2569691B1 (fr)	1989-08-04
NL8502384A (nl)	1986-03-17
AU647978B2 (en)	1994-03-31
SE8504048D0 (sv)	1985-08-30
SE500669C2 (sv)	1994-08-08
MX159807A (es)	1989-08-31
ES8703142A1 (es)	1986-11-16
IT1189601B (it)	1988-02-04
DE3531487A1 (de)	1986-03-13

Legal Events

Date	Code	Title	Description
2001-04-12	PL	Patent ceased

Publication	Publication Date	Title
FR2569691A1 (fr)	1986-03-07	Derives de benzimidazole, procede pour les preparer et agents anti-ulcereux les contenant
EP0557171B1 (fr)	1995-07-19	Azaindoles, procédés de préparation et médicaments les contenant
EP0506532B1 (fr)	1994-09-07	Nouveaux dérivés de l'indole, procédé de préparation et médicaments les contenant
FR2643903A1 (fr)	1990-09-07	Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux
BE851310A (fr)	1977-08-10	Nouveaux derives de la tetrahydro-equinocandine b
FR2555584A1 (fr)	1985-05-31	Derives de l'acide fluoro-6-dihydro-1,4-oxo-4-piperazinyl substitue-7-quinoline-carboxylique-3 et procede pour leur preparation et compositions pharmaceutiques a action anti-bacteriennes a base desdits derives
EP0611766A1 (fr)	1994-08-24	Dérivés de 2-amido-thiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament
FR2705095A1 (fr)	1994-11-18	Nouveaux indoles substitués, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
EP0109866B1 (fr)	1987-08-19	Nouveaux dérivés de la sulfonylurée, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP0117771B1 (fr)	1987-11-11	Imino-2 pyrrolidines, leur procédé de préparation et leurs applications en thérapeutique
EP0533827B1 (fr)	1994-08-24	Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2691461A1 (fr)	1993-11-26	Dérivés de cycloheptimidazole, procédé pour les préparer et composition pharmaceutique et agents thérapeutiques les contenant.
HU194244B (en)	1988-01-28	Process for production of derivatives of new tieno /2,3-d/ imidasole and medical compounds containing thereof
EP0084993A2 (fr)	1983-08-03	Nouveaux dérivés de benzodioxine, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
EP0638568B1 (fr)	1996-10-09	Pipérazines substituées, leur procédé de préparation et les compositions pharmaceutiques les contenant
FR2491064A1 (fr)	1982-04-02	Quinolones, leurs procedes de preparation et composition therapeutique les contenant
RU2069212C1 (ru)	1996-11-20	Производные имидазола
CA2010529A1 (fr)	1990-08-22	Derives de la 1-arylsulfonyl 2-piperidinone, leur procede et les intermediaires de preparation, leur application comme medicaments et les compositions les renfermant
LU85780A1 (fr)	1985-12-11	Nouveaux esters enoliques precurseurs de medicaments et composition pharmaceutique les contenant
MC1347A1 (fr)	1981-06-22	Derives de pyridazopyridazine
EP0613470B1 (fr)	1996-01-10	Nouveaux derives de cinnolinones-4, leur preparation et leur application en therapeutique
EP0002401B1 (fr)	1980-12-10	Dérivés de naphtalène, leur préparation et leur application en thérapeutique
JP2816974B2 (ja)	1998-10-27	ベンズイミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤
EP0705261A1 (fr)	1996-04-10	Naphtyridines antiproliferatives
EP0412014A1 (fr)	1991-02-06	Dérivés benzothiaziniques, leur préparation et leurs applications comme médicaments ou comme intermédiaires de synthèse de médicaments