NO874454L - Nye derivater av benzimidazoler med anti-ulcusaktivitet og fremgangsmaate for deres fremstilling. - Google Patents

Nye derivater av benzimidazoler med anti-ulcusaktivitet og fremgangsmaate for deres fremstilling.

Info

Publication number: NO874454L
Authority: NO; Norway
Prior art keywords: group; carbon atoms; compound; hydrogen; lower alkyl
Prior art date: 1986-10-27

Application number

NO874454A

Other languages

English (en)

Norwegian (no)

Other versions

NO874454D0 (no

Inventor

Carin Birgitta Briving

Stig Aake Ingemar Carlsson

Per Lennart Lindberg

Annie Hillevi Mattsson

Mats Peter Nordberg

Bjoern Morgan Gabriel Wallmark

Original Assignee

Haessle Ab

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.)

1986-10-27

Filing date

1987-10-26

Publication date

1988-04-28

1987-10-26 Application filed by Haessle Ab filed Critical Haessle Ab

1987-10-26 Publication of NO874454D0 publication Critical patent/NO874454D0/no

1988-04-28 Publication of NO874454L publication Critical patent/NO874454L/no

Links

238000002360 preparation method Methods 0.000 title claims abstract description 21
238000000034 method Methods 0.000 title claims abstract description 12
150000001556 benzimidazoles Chemical class 0.000 title description 4
230000000694 effects Effects 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 87
125000000217 alkyl group Chemical group 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 37
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
150000002431 hydrogen Chemical class 0.000 claims abstract description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
239000004480 active ingredient Substances 0.000 claims abstract description 5
230000027119 gastric acid secretion Effects 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 11
210000001035 gastrointestinal tract Anatomy 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
230000001120 cytoprotective effect Effects 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000004450 alkenylene group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
230000002496 gastric effect Effects 0.000 abstract description 2
230000002401 inhibitory effect Effects 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract 1
230000002757 inflammatory effect Effects 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
239000007903 gelatin capsule Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
PHKXHIBYXGTHFI-UHFFFAOYSA-N 2-methyl-4-phenylmethoxy-1h-benzimidazole Chemical compound C=12NC(C)=NC2=CC=CC=1OCC1=CC=CC=C1 PHKXHIBYXGTHFI-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
PCAXITAPTVOLGL-UHFFFAOYSA-N 2,3-diaminophenol Chemical compound NC1=CC=CC(O)=C1N PCAXITAPTVOLGL-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000002702 enteric coating Substances 0.000 description 3
238000009505 enteric coating Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
230000002265 prevention Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003039 volatile agent Substances 0.000 description 3
QKGICRIKYBKQNP-UHFFFAOYSA-N 1,2-dimethyl-7-phenylmethoxybenzimidazole Chemical compound C=12N(C)C(C)=NC2=CC=CC=1OCC1=CC=CC=C1 QKGICRIKYBKQNP-UHFFFAOYSA-N 0.000 description 2
MCWZEPZHNJEFMF-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-2-methyl-1h-benzimidazole Chemical compound C=12NC(C)=NC2=CC=CC=1OCC1=CC=C(Cl)C=C1 MCWZEPZHNJEFMF-UHFFFAOYSA-N 0.000 description 2
WJEROTWBZUBPBL-UHFFFAOYSA-N 4-[(4-fluorophenyl)methoxy]-2-methyl-1h-benzimidazole Chemical compound C=12NC(C)=NC2=CC=CC=1OCC1=CC=C(F)C=C1 WJEROTWBZUBPBL-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical class 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 2
229920000945 Amylopectin Chemical class 0.000 description 2
229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Chemical class OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Chemical class 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Chemical class 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000001913 cellulose Chemical class 0.000 description 2
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229940081734 cellulose acetate phthalate Drugs 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000010828 elution Methods 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
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229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000000594 mannitol Chemical class 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
QTGWIBNVFTVALF-UHFFFAOYSA-N n-benzyl-2-methyl-1h-benzimidazol-4-amine Chemical compound C=12NC(C)=NC2=CC=CC=1NCC1=CC=CC=C1 QTGWIBNVFTVALF-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
235000019204 saccharin Nutrition 0.000 description 2
229940081974 saccharin Drugs 0.000 description 2
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000600 sorbitol Chemical class 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005720 sucrose Chemical class 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
GUKDYOOFYYGMCB-UHFFFAOYSA-N (4-phenylmethoxy-1h-benzimidazol-2-yl)methanol Chemical compound C=12NC(CO)=NC2=CC=CC=1OCC1=CC=CC=C1 GUKDYOOFYYGMCB-UHFFFAOYSA-N 0.000 description 1
GCIVGINMHDIFQG-UHFFFAOYSA-N 1,2-dimethyl-4-phenylmethoxybenzimidazole Chemical compound C1=CC=C2N(C)C(C)=NC2=C1OCC1=CC=CC=C1 GCIVGINMHDIFQG-UHFFFAOYSA-N 0.000 description 1
YTZCFHCTJSGSCD-UHFFFAOYSA-N 1,2-dinitro-3-phenylmethoxybenzene Chemical compound [O-][N+](=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1[N+]([O-])=O YTZCFHCTJSGSCD-UHFFFAOYSA-N 0.000 description 1
MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QHSXNTMXBGABQI-UHFFFAOYSA-N 2-ethyl-4-phenylmethoxy-1h-benzimidazole Chemical compound C=12NC(CC)=NC2=CC=CC=1OCC1=CC=CC=C1 QHSXNTMXBGABQI-UHFFFAOYSA-N 0.000 description 1
USVXDODAPOBXCF-UHFFFAOYSA-N 2-methyl-1h-benzimidazol-4-amine Chemical compound C1=CC=C2NC(C)=NC2=C1N USVXDODAPOBXCF-UHFFFAOYSA-N 0.000 description 1
HLPAESMITTURFN-UHFFFAOYSA-N 2-methyl-1h-benzimidazol-4-ol Chemical compound C1=CC=C2NC(C)=NC2=C1O HLPAESMITTURFN-UHFFFAOYSA-N 0.000 description 1
QHTRLAWJHCCQPK-UHFFFAOYSA-N 2-methyl-4-(2-phenylethoxy)-1h-benzimidazole Chemical compound C=12NC(C)=NC2=CC=CC=1OCCC1=CC=CC=C1 QHTRLAWJHCCQPK-UHFFFAOYSA-N 0.000 description 1
MHUPUZTUFWWCGG-UHFFFAOYSA-N 2-methyl-6-phenylmethoxy-1h-benzimidazole Chemical compound C1=C2NC(C)=NC2=CC=C1OCC1=CC=CC=C1 MHUPUZTUFWWCGG-UHFFFAOYSA-N 0.000 description 1
NSGSUVJJLZZPPY-UHFFFAOYSA-N 3-phenylmethoxybenzene-1,2-diamine Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1N NSGSUVJJLZZPPY-UHFFFAOYSA-N 0.000 description 1
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 1
SMRNKUZWECPXHV-UHFFFAOYSA-N 4-phenylmethoxy-1h-benzimidazole Chemical compound C=1C=CC=2N=CNC=2C=1OCC1=CC=CC=C1 SMRNKUZWECPXHV-UHFFFAOYSA-N 0.000 description 1
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150000008041 alkali metal carbonates Chemical class 0.000 description 1
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CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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208000000718 duodenal ulcer Diseases 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
201000000052 gastrinoma Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
-1 methanol or ethanol Chemical compound 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
MNZMFKCQTRWMLC-UHFFFAOYSA-N n-(2-acetamido-3-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(O)=C1NC(C)=O MNZMFKCQTRWMLC-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229920001592 potato starch Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Chemical class 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
150000005846 sugar alcohols Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000001993 wax Substances 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen 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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Wire Bonding (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Control Of El Displays (AREA)

NO874454A 1986-10-27 1987-10-26 Nye derivater av benzimidazoler med anti-ulcusaktivitet og fremgangsmaate for deres fremstilling. NO874454L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8604566A SE8604566D0 (sv)	1986-10-27	1986-10-27	Novel compunds

Publications (2)

Publication Number	Publication Date
NO874454D0 NO874454D0 (no)	1987-10-26
NO874454L true NO874454L (no)	1988-04-28

Family

ID=20366077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO874454A NO874454L (no)	1986-10-27	1987-10-26	Nye derivater av benzimidazoler med anti-ulcusaktivitet og fremgangsmaate for deres fremstilling.

Country Status (22)

Country	Link
US (1)	US5106862A (de)
EP (1)	EP0266326B1 (de)
JP (1)	JP2738932B2 (de)
KR (1)	KR880005092A (de)
CN (1)	CN87107175A (de)
AT (1)	ATE86616T1 (de)
AU (1)	AU7949887A (de)
DD (1)	DD264433A5 (de)
DE (1)	DE3784624T2 (de)
DK (1)	DK555387A (de)
ES (1)	ES2053587T3 (de)
FI (1)	FI874702A7 (de)
HU (1)	HU196971B (de)
IE (1)	IE872768L (de)
IL (1)	IL84193A0 (de)
NO (1)	NO874454L (de)
NZ (1)	NZ222104A (de)
PL (1)	PL268455A1 (de)
PT (1)	PT86008B (de)
SE (1)	SE8604566D0 (de)
SU (1)	SU1597100A3 (de)
ZA (1)	ZA877400B (de)

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GB8307865D0 (en) *	1983-03-22	1983-04-27	Fujisawa Pharmaceutical Co	Benzimidazole derivatives
JPS59188868A (ja) *	1983-04-08	1984-10-26	Matsushita Electric Ind Co Ltd	テ−プ引出し装置
JPS60226810A (ja) *	1984-04-25	1985-11-12	Ikeda Mohandou:Kk	抗潰瘍剤
GB8417194D0 (en) *	1984-07-05	1984-08-08	Boots Co Plc	Therapeutic agents
EP0174717B1 (de) *	1984-07-06	1992-01-22	FISONS plc	Benzimidazole, und Verfahren zu deren Herstellung, deren Formulierung und Verwendung als magensäuresekretionshemmende Verbindungen
EP0178413A1 (de) *	1984-08-17	1986-04-23	Beecham Group Plc	Benzimidazole

1986
- 1986-10-27 SE SE8604566A patent/SE8604566D0/xx unknown
1987
- 1987-10-01 ZA ZA877400A patent/ZA877400B/xx unknown
- 1987-10-09 NZ NZ222104A patent/NZ222104A/xx unknown
- 1987-10-09 AU AU79498/87A patent/AU7949887A/en not_active Abandoned
- 1987-10-14 IE IE872768A patent/IE872768L/xx unknown
- 1987-10-18 IL IL84193A patent/IL84193A0/xx unknown
- 1987-10-19 AT AT87850313T patent/ATE86616T1/de not_active IP Right Cessation
- 1987-10-19 EP EP87850313A patent/EP0266326B1/de not_active Expired - Lifetime
- 1987-10-19 ES ES87850313T patent/ES2053587T3/es not_active Expired - Lifetime
- 1987-10-19 DE DE8787850313T patent/DE3784624T2/de not_active Expired - Fee Related
- 1987-10-23 DK DK555387A patent/DK555387A/da not_active Application Discontinuation
- 1987-10-26 SU SU874203542A patent/SU1597100A3/ru active
- 1987-10-26 HU HU874769A patent/HU196971B/hu not_active IP Right Cessation
- 1987-10-26 KR KR870011881A patent/KR880005092A/ko not_active Withdrawn
- 1987-10-26 DD DD87308279A patent/DD264433A5/de not_active IP Right Cessation
- 1987-10-26 NO NO874454A patent/NO874454L/no unknown
- 1987-10-26 JP JP62268376A patent/JP2738932B2/ja not_active Expired - Fee Related
- 1987-10-26 FI FI874702A patent/FI874702A7/fi not_active IP Right Cessation
- 1987-10-27 PL PL1987268455A patent/PL268455A1/xx unknown
- 1987-10-27 CN CN198787107175A patent/CN87107175A/zh active Pending
- 1987-10-27 PT PT86008A patent/PT86008B/pt not_active IP Right Cessation
1990
- 1990-12-12 US US07/631,221 patent/US5106862A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
SE8604566D0 (sv)	1986-10-27
NO874454D0 (no)	1987-10-26
ES2053587T3 (es)	1994-08-01
DK555387A (da)	1988-04-28
AU7949887A (en)	1988-04-28
KR880005092A (ko)	1988-06-28
FI874702L (fi)	1988-04-28
ATE86616T1 (de)	1993-03-15
FI874702A0 (fi)	1987-10-26
PL268455A1 (en)	1988-09-01
FI874702A7 (fi)	1988-04-28
IE872768L (en)	1988-04-27
DD264433A5 (de)	1989-02-01
ZA877400B (en)	1988-04-27
PT86008B (pt)	1990-08-31
US5106862A (en)	1992-04-21
JP2738932B2 (ja)	1998-04-08
HU196971B (en)	1989-02-28
PT86008A (en)	1987-11-01
EP0266326B1 (de)	1993-03-10
DE3784624D1 (de)	1993-04-15
DK555387D0 (da)	1987-10-23
NZ222104A (en)	1990-07-26
JPS63122675A (ja)	1988-05-26
SU1597100A3 (ru)	1990-09-30
DE3784624T2 (de)	1993-06-17
IL84193A0 (en)	1988-03-31
EP0266326A1 (de)	1988-05-04
CN87107175A (zh)	1988-05-11
HUT45236A (en)	1988-06-28

Publication	Publication Date	Title
NO874454L (no)	1988-04-28	Nye derivater av benzimidazoler med anti-ulcusaktivitet og fremgangsmaate for deres fremstilling.
US5039806A (en)	1991-08-13	Novel pharmacologically active compound pyridyl methylsulfinyl benzimidazole
EP0535081A1 (de)	1993-04-07	Substituierte benzimidazole, verfahren zur herstellung und pharmazeutische verwendung
SG187400A1 (en)	2013-02-28	(aza)indole derivative substituted in position 5,pharmaceutical composition comprising it, intermediate compounds and preparation process therefor
HU198060B (en)	1989-07-28	Process for producing new thienopyridinones and pharmaceutical compositions comprising same
US4420479A (en)	1983-12-13	Olefinic benzimidazoles, formulations, and antiviral methods
HU209293B (en)	1994-04-28	Process for producing cyclic substituted (quinolin-2-yl-methoxy)-phenyl acetic acid derivatives and pharmaceutical compositions containing them
JP2964029B2 (ja)	1999-10-18	カルボスチリル誘導体
CA1208643A (en)	1986-07-29	1,5-diphenyl-pyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing them
NO164899B (no)	1990-08-20	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolylindolforbindelser.
EP0319170B1 (de)	1993-03-17	Acyl-Derivate von Hydroxy-Pyrimidinen
SK86593A3 (en)	1994-06-08	Substituted quinol-2-yl-methoxy-phenylacetic acid derivatives
JPS58188868A (ja)	1983-11-04	オレフイン系ベンズイミダゾ−ル類
CA2011952A1 (en)	1990-09-14	Leukotriene-inhibiting substituted (quinolin-2-yl-methoxy) phenyl-n,n'-sulphonylureas
ZA200507258B (en)	2006-06-28	4, 6-, or 7-hydroxyindoles having n-oxide groups and the use thereof as therapeutic agents
JP3269658B2 (ja)	2002-03-25	フェノール誘導体
EP0412529A1 (de)	1991-02-13	Imidazolderivate, Verfahren zu deren Herstellung und diese enthaltende Antiulkusmittel
US5338746A (en)	1994-08-16	Thiosemicarbazonic acid esters
US5049674A (en)	1991-09-17	Therapeutically active fluoro substituted benzimidazoles
KR870000287B1 (ko)	1987-02-25	피페라진 유도체의 제조방법
HU204796B (en)	1992-02-28	Process for producing benzimidazole derivatives
JPH0425268B2 (de)	1992-04-30
JPH10330262A (ja)	1998-12-15	医薬組成物
CA1210763A (en)	1986-09-02	1,5-diphenyl-pyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing them
JPH04257581A (ja)	1992-09-11	ピペリジノメチルピリジン誘導体