SE500669C2 - Bensimidazolderivat - Google Patents

Bensimidazolderivat

Info

Publication number: SE500669C2
Authority: SE; Sweden
Prior art keywords: benzimidazole; dimethylamino; compound; dimethylaminobenzylsulfinyl; solution
Prior art date: 1984-08-31

Application number

SE8504048A

Other languages

English (en)

Swedish (sv)

Other versions

SE8504048L (sv

SE8504048D0 (sv

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

1985-08-30

Publication date

1994-08-08

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

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

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

1985-08-30 Application filed by Nippon Chemiphar Co filed Critical Nippon Chemiphar Co

1985-08-30 Publication of SE8504048D0 publication Critical patent/SE8504048D0/xx

1986-03-01 Publication of SE8504048L publication Critical patent/SE8504048L/xx

1994-08-08 Publication of SE500669C2 publication Critical patent/SE500669C2/sv

Links

150000001556 benzimidazoles Chemical class 0.000 title claims description 11
-1 2-amino benzyl Chemical group 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 4
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 claims description 3
DKAJHHLUKNOBFB-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n-methylaniline Chemical compound CNC1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 DKAJHHLUKNOBFB-UHFFFAOYSA-N 0.000 claims description 3
INGIXPMMNAFVHF-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)aniline Chemical compound NC1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 INGIXPMMNAFVHF-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
MEFSZCZOGKYDNK-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfinylmethyl)-5-chloro-N,N-dimethylaniline Chemical compound CN(C1=C(CS(=O)C=2NC3=C(N=2)C=CC=C3)C=CC(=C1)Cl)C MEFSZCZOGKYDNK-UHFFFAOYSA-N 0.000 claims 1
XFXQCYXMKIICBF-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfinylmethyl)-N-benzylaniline Chemical compound C1(=CC=CC=C1)CNC1=C(CS(=O)C=2NC3=C(N=2)C=CC=C3)C=CC=C1 XFXQCYXMKIICBF-UHFFFAOYSA-N 0.000 claims 1
AWEHASWEAGKBRX-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfinylmethyl)-N-cyclohexylaniline Chemical compound C1(CCCCC1)NC1=C(CS(=O)C=2NC3=C(N=2)C=CC=C3)C=CC=C1 AWEHASWEAGKBRX-UHFFFAOYSA-N 0.000 claims 1
AKRBSYBDTZIKJN-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfinylmethyl)-N-phenylaniline Chemical compound C1(=CC=CC=C1)NC1=C(CS(=O)C=2NC3=C(N=2)C=CC=C3)C=CC=C1 AKRBSYBDTZIKJN-UHFFFAOYSA-N 0.000 claims 1
JAONZDYCQQDNSR-UHFFFAOYSA-N methyl 2-[[2-(dimethylamino)phenyl]methylsulfinyl]-3h-benzimidazole-5-carboxylate Chemical compound N1C2=CC(C(=O)OC)=CC=C2N=C1S(=O)CC1=CC=CC=C1N(C)C JAONZDYCQQDNSR-UHFFFAOYSA-N 0.000 claims 1
NEGXXYIOWVTFAE-UHFFFAOYSA-N n,n-dimethyl-2-[(6-methyl-1h-benzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=C(C)C=C2N1 NEGXXYIOWVTFAE-UHFFFAOYSA-N 0.000 claims 1
OQVZBTLMQOMEJM-UHFFFAOYSA-N n,n-dimethyl-2-[[6-(trifluoromethyl)-1h-benzimidazol-2-yl]sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N1 OQVZBTLMQOMEJM-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 65
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 abstract description 11
238000000034 method Methods 0.000 abstract description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
239000012442 inert solvent Substances 0.000 abstract description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract description 4
FVABKKHWAAELQW-UHFFFAOYSA-N 2-benzylsulfinyl-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=C1 FVABKKHWAAELQW-UHFFFAOYSA-N 0.000 abstract description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract description 3
239000005708 Sodium hypochlorite Substances 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
150000004967 organic peroxy acids Chemical class 0.000 abstract description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 2
229910052736 halogen Inorganic materials 0.000 abstract 2
150000002367 halogens Chemical class 0.000 abstract 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
239000003513 alkali Substances 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
239000000243 solution Substances 0.000 description 46
150000001875 compounds Chemical class 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
239000013078 crystal Substances 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000203 mixture Substances 0.000 description 21
230000002829 reductive effect Effects 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
238000001914 filtration Methods 0.000 description 14
239000012046 mixed solvent Substances 0.000 description 14
241000700159 Rattus Species 0.000 description 13
239000000843 powder Substances 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
210000002784 stomach Anatomy 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
230000003628 erosive effect Effects 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
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
238000002360 preparation method Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000004615 ingredient Substances 0.000 description 7
229940126214 compound 3 Drugs 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
BLKLDWQFHUIMPR-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 BLKLDWQFHUIMPR-UHFFFAOYSA-N 0.000 description 5
JVIHSTYYPRUSFG-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfinylmethyl)-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1 JVIHSTYYPRUSFG-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000010410 layer Substances 0.000 description 5
108091006112 ATPases Proteins 0.000 description 4
102000057290 Adenosine Triphosphatases Human genes 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
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 4
241001465754 Metazoa Species 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
229940125904 compound 1 Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
229960000905 indomethacin Drugs 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000008101 lactose 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
238000005406 washing Methods 0.000 description 4
VOBSIAVREZZSNT-UHFFFAOYSA-N 2-(1H-benzimidazol-2-ylsulfanylmethyl)-N,N,3-trimethylaniline Chemical compound CN(C1=C(CSC=2NC3=C(N2)C=CC=C3)C(=CC=C1)C)C VOBSIAVREZZSNT-UHFFFAOYSA-N 0.000 description 3
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 3
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 3
DVMJQEIKYMPLRN-UHFFFAOYSA-N 2-[(2-piperidin-1-ylphenyl)methylsulfanyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1SCC1=CC=CC=C1N1CCCCC1 DVMJQEIKYMPLRN-UHFFFAOYSA-N 0.000 description 3
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 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
230000000762 glandular Effects 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000007654 immersion Methods 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
210000001187 pylorus Anatomy 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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 2
VIDRTFCKVZQFTK-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylsulfanylmethyl)aniline Chemical compound NC1=CC=CC=C1CSC1=NC2=CC=CC=C2N1 VIDRTFCKVZQFTK-UHFFFAOYSA-N 0.000 description 2
FNCFJTCLEAAISA-UHFFFAOYSA-N 2-[(2-piperidin-1-ylphenyl)methylsulfinyl]-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=C1N1CCCCC1 FNCFJTCLEAAISA-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
UZNORZYEAOXIAO-UHFFFAOYSA-N N,N-dimethyl-2-[(4-methyl-1H-benzimidazol-2-yl)sulfanylmethyl]aniline Chemical compound CN(C1=C(CSC=2NC3=C(N2)C=CC=C3C)C=CC=C1)C UZNORZYEAOXIAO-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
NDGRHDGMNRMJOP-UHFFFAOYSA-N [2-(chloromethyl)phenyl]-dimethylazanium;chloride Chemical compound Cl.CN(C)C1=CC=CC=C1CCl NDGRHDGMNRMJOP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
229960001380 cimetidine Drugs 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000007884 disintegrant Substances 0.000 description 2
210000004211 gastric acid Anatomy 0.000 description 2
230000027119 gastric acid secretion Effects 0.000 description 2
208000014674 injury Diseases 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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
229920000036 polyvinylpyrrolidone Polymers 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
238000005303 weighing Methods 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
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 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
AYTATRSVDRFXIW-UHFFFAOYSA-N 2-(chloromethyl)-n-methylaniline;hydrochloride Chemical compound Cl.CNC1=CC=CC=C1CCl AYTATRSVDRFXIW-UHFFFAOYSA-N 0.000 description 1
GNQNKEIEADCBFT-UHFFFAOYSA-N 2-(chloromethyl)aniline;hydrochloride Chemical compound Cl.NC1=CC=CC=C1CCl GNQNKEIEADCBFT-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
KOFBRZWVWJCLGM-UHFFFAOYSA-N 5-methoxy-1,3-dihydrobenzimidazole-2-thione Chemical compound COC1=CC=C2NC(S)=NC2=C1 KOFBRZWVWJCLGM-UHFFFAOYSA-N 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
241000428352 Amma Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
SYMUPNRZZYSUOL-UHFFFAOYSA-N Cl.N1(CCCCC1)C1=C(CCl)C=CC=C1 Chemical compound Cl.N1(CCCCC1)C1=C(CCl)C=CC=C1 SYMUPNRZZYSUOL-UHFFFAOYSA-N 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
208000005156 Dehydration Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
101150048818 Faim gene Proteins 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
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229910019093 NaOCl Inorganic materials 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
210000001015 abdomen Anatomy 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
238000011047 acute toxicity test Methods 0.000 description 1
230000000767 anti-ulcer Effects 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 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
238000004587 chromatography analysis Methods 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125782 compound 2 Drugs 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
239000003085 diluting agent Substances 0.000 description 1
239000003480 eluent Substances 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 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
239000002504 physiological saline solution Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 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
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)

SE8504048A 1984-08-31 1985-08-30 Bensimidazolderivat SE500669C2 (sv)

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
JP60061195A JPH0764826B2 (ja)	1985-03-26	1985-03-26	ベンズイミダゾール誘導体
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

Publications (3)

Publication Number	Publication Date
SE8504048D0 SE8504048D0 (sv)	1985-08-30
SE8504048L SE8504048L (sv)	1986-03-01
SE500669C2 true SE500669C2 (sv)	1994-08-08

Family

ID=27297422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8504048A SE500669C2 (sv)	1984-08-31	1985-08-30	Bensimidazolderivat

Country Status (14)

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

Families Citing this family (67)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8417194D0 (en) *	1984-07-05	1984-08-08	Boots Co Plc	Therapeutic agents
DE3585252D1 (de)	1984-07-06	1992-03-05	Fisons Plc	Benzimidazole, und verfahren zu deren herstellung, deren formulierung und verwendung als magensaeuresekretionshemmende verbindungen.
GB2161160B (en) *	1984-07-06	1989-05-24	Fisons Plc	Heterocyclic sulphinyl compounds
EP0204215B1 (fr) *	1985-05-24	1993-08-11	G.D. Searle & Co.	[(1H-benzimidazol-yl-2-sulfonyl)méthyl]-2-benzèneamines
US5869513A (en) *	1985-05-24	1999-02-09	G. D. Searle & Co.	2- (1H-benzimidazol-2-ylsulfinyl)methyl!benzenamines
US4824856A (en) *	1985-08-14	1989-04-25	Nippon Chemiphar Co., Ltd.	Method of protecting gastrointestinal tract
EP0232399A1 (fr) *	1985-08-21	1987-08-19	Byk Gulden Lomberg Chemische Fabrik GmbH	Nouvelles amines, leur procede de fabrication, leur utilisation, et medicaments les contenant
AR243167A1 (es)	1985-08-24	1993-07-30	Hoechst Ag	Procedimiento para la preparacion de toluidinas sustituidas.
AU619444B2 (en) *	1986-06-02	1992-01-30	Nippon Chemiphar Co. Ltd.	2-(2-aminobenzylsulfinyl)- benzimidazole derivatives
EP0251536A1 (fr) *	1986-06-24	1988-01-07	FISONS plc	Benzimidazoles, leur préparation, formulation et utilisation comme inhibiteurs de sécrétion d'acide gastrique
US4687775A (en) *	1986-07-17	1987-08-18	G. D. Searle & Co.	2-[(Imidazo[1,2-a]pyridinylmethyl)sulfinyl]-1H-benzimidazoles
US4772619A (en) *	1986-07-17	1988-09-20	G. D. Searle & Co.	[(1H-benzimidazol-2-ylsulfinyl)methyl]-2-pyridinamines
US4721718A (en) *	1986-08-18	1988-01-26	G. D. Searle & Co.	2-[(imidazo[1,2-a]pyridin-3-ylmethyl)sulfinyl]-1H-benzimidazoles useful in the treatment and prevention of ulcers
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
SE9402431D0 (sv) *	1994-07-08	1994-07-08	Astra Ab	New tablet formulation
SE9500422D0 (sv) *	1995-02-06	1995-02-06	Astra Ab	New oral pharmaceutical dosage forms
SE9500478D0 (sv) *	1995-02-09	1995-02-09	Astra Ab	New pharmaceutical formulation and process
US5708017A (en) *	1995-04-04	1998-01-13	Merck & Co., Inc.	Stable, ready-to-use pharmaceutical paste composition containing proton pump inhibitors
HRP960232A2 (en) *	1995-07-03	1998-02-28	Astra Ab	A process for the optical purification of compounds
ATE286394T1 (de) *	1995-09-21	2005-01-15	Pharma Pass Ii Llc	Ein säurelabile omeprazol enthaltende arzneizusammensetzung und verfahren zu deren herstellung
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
WO1999004816A1 (fr)	1997-07-25	1999-02-04	Byk Gulden Lomberg Chemische Fabrik Gmbh	Inhibiteur de la pompe a protons en combinaison therapeutique avec des substances antibacteriennes
SE9704869D0 (sv) *	1997-12-22	1997-12-22	Astra Ab	New pharmaceutical formulaton II
SE9704870D0 (sv)	1997-12-22	1997-12-22	Astra Ab	New pharmaceutical formulation I
ATE321538T1 (de)	1998-08-12	2006-04-15	Altana Pharma Ag	Orale darreichungsform für pyridin-2- ylmethylsulfinyl-1h-benzimidazole
AU1054899A (en) *	1998-11-06	2000-05-29	Dong-A Pharmaceutical Co., Ltd.	Method of preparing sulfide derivatives
TWI243672B (en)	1999-06-01	2005-11-21	Astrazeneca Ab	New use of compounds as antibacterial agents
ES2246238T3 (es)	1999-06-07	2006-02-16	Altana Pharma Ag	Nueva preparacion y forma de administracion que comprende un inhibidor de las bombas de protones labil en medio acido.
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
EP1492511B3 (fr)	2002-04-09	2012-05-02	Flamel Technologies	Formulation pharmaceutique orale sous forme de suspension aqueuse de microcapsules permettant la liberation modifiee de principe(s) actif(s)
JP4698950B2 (ja)	2002-04-09	2011-06-08	フラメル・テクノロジー	アモキシシリンの改変された放出のための、マイクロカプセルの水性懸濁液形態での経口医薬品製剤
SE0203065D0 (sv)	2002-10-16	2002-10-16	Diabact Ab	Gastric acid secretion inhibiting composition
US8802139B2 (en)	2003-06-26	2014-08-12	Intellipharmaceutics Corp.	Proton pump-inhibitor-containing capsules which comprise subunits differently structured for a delayed release of the active ingredient
CA2540308C (fr)	2003-09-26	2013-08-06	Alza Corporation	Enrobage de medicaments a charge medicamenteuse elevee et procedes de fabrication
US8394409B2 (en)	2004-07-01	2013-03-12	Intellipharmaceutics Corp.	Controlled extended drug release technology
US20060024362A1 (en)	2004-07-29	2006-02-02	Pawan Seth	Composition comprising a benzimidazole and process for its manufacture
US10624858B2 (en)	2004-08-23	2020-04-21	Intellipharmaceutics Corp	Controlled release composition using transition coating, and method of preparing same
US8541026B2 (en)	2004-09-24	2013-09-24	Abbvie Inc.	Sustained release formulations of opioid and nonopioid analgesics
US7981908B2 (en)	2005-05-11	2011-07-19	Vecta, Ltd.	Compositions and methods for inhibiting gastric acid secretion
US7803817B2 (en)	2005-05-11	2010-09-28	Vecta, Ltd.	Composition and methods for inhibiting gastric acid secretion
US10064828B1 (en)	2005-12-23	2018-09-04	Intellipharmaceutics Corp.	Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems
JP5457830B2 (ja)	2006-04-03	2014-04-02	オディディ，イサ	オルガノゾル被膜を含む制御放出送達デバイス
US10960077B2 (en)	2006-05-12	2021-03-30	Intellipharmaceutics Corp.	Abuse and alcohol resistant drug composition
PL2046334T3 (pl)	2006-07-25	2015-02-27	Vecta Ltd	Kompozycje i sposoby hamowania wydzielania kwasów żołądkowych z wykorzystaniem pochodnych małych kwasów dikarboksylowych w połączeniu z PPI
EP2124884B1 (fr)	2006-12-22	2019-07-10	Ironwood Pharmaceuticals, Inc.	Compositions contenant des chelateurs d'acide biliaire pour le traitement des troubles oesphagiens
US9220698B2 (en)	2008-09-09	2015-12-29	Pozen Inc.	Method for delivering a pharmaceutical composition to patient in need thereof
KR20120030106A (ko)	2009-06-25	2012-03-27	아스트라제네카 아베	Ｎｓａｉｄ-연관된 궤양의 발생 위험이 있는 환자의 치료 방법
WO2011080500A2 (fr)	2009-12-29	2011-07-07	Orexo Ab	Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique
WO2011080502A2 (fr)	2009-12-29	2011-07-07	Orexo Ab	Nouvelle forme pharmaceutique destinée au traitement de troubles liés à l'acide gastrique
US20120294937A1 (en)	2009-12-29	2012-11-22	Novartis Ag	New pharmaceutical dosage form for the treatment of gastric acid-related disorders
WO2012027331A1 (fr)	2010-08-27	2012-03-01	Ironwood Pharmaceuticals, Inc.	Compositions et procédés pour traiter ou prévenir un syndrome métabolique et des maladies et troubles associés
EP2601947A1 (fr)	2011-12-05	2013-06-12	Abo Bakr Mohammed Ali Al-Mehdar	Combinaison à dose fixe pour le traitement de maladies associées à Hélicobacter pylori
EP2797600A4 (fr)	2011-12-28	2015-09-16	Pozen Inc	Compositions et procédés d'administration d'oméprazole plus acide acétylsalicylique améliorés
CA2898362C (fr)	2013-01-15	2020-09-01	Ironwood Pharmaceuticals, Inc.	Forme posologique orale a liberation prolongee a retention gastrique d'un agent sequestrant d'acide biliaire
EP2801565B1 (fr) *	2013-05-06	2015-07-22	King Saud University	Composés destinés à être utilisés en tant qu'agent antiulcéreux et/ou agent anti-helicobacter pylori et leurs compositions pharmaceutiques
US20180015118A1 (en)	2015-02-03	2018-01-18	Ironwood Pharmaceuticals, Inc.	Methods of treating upper gastrointestinal disorders in ppi refractory gerd

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4359465A (en) *	1980-07-28	1982-11-16	The Upjohn Company	Methods for treating gastrointestinal inflammation
DE3585252D1 (de) *	1984-07-06	1992-03-05	Fisons Plc	Benzimidazole, und verfahren zu deren herstellung, deren formulierung und verwendung als magensaeuresekretionshemmende verbindungen.

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 AR AR85301474A patent/AR242195A1/es active
- 1985-08-30 BR BR8504252A patent/BR8504252A/pt unknown
- 1985-08-30 MX MX206462A patent/MX159807A/es unknown
- 1985-08-30 SE SE8504048A patent/SE500669C2/sv 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 IT IT67743/85A patent/IT1189601B/it active
- 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
KR860001793A (ko)	1986-03-22
CH665417A5 (fr)	1988-05-13
AU4127189A (en)	1989-12-21
SE8504048L (sv)	1986-03-01
NL8502384A (nl)	1986-03-17
BR8504252A (pt)	1986-06-17
IT8567743A0 (it)	1985-08-30
AR242195A1 (es)	1993-03-31
ES8703142A1 (es)	1986-11-16
FR2569691B1 (fr)	1989-08-04
KR920004936B1 (ko)	1992-06-22
DE3531487A1 (de)	1986-03-13
FR2569691A1 (fr)	1986-03-07
IT1189601B (it)	1988-02-04
BE903128A (fr)	1985-12-16
GB2163747A (en)	1986-03-05
AU2975092A (en)	1993-01-28
MX159807A (es)	1989-08-31
AU647978B2 (en)	1994-03-31
GB8521493D0 (en)	1985-10-02
AU4640985A (en)	1986-03-06
SE8504048D0 (sv)	1985-08-30
GB2163747B (en)	1989-02-08
ES546445A0 (es)	1986-11-16
DE3531487C2 (de)	1995-08-17

Publication	Publication Date	Title
SE500669C2 (sv)	1994-08-08	Bensimidazolderivat
WO2001014371A1 (fr)	2001-03-01	Derives n-heterocycliques sous forme d'inhibiteurs oxyde nitrique synthase
JPH08506576A (ja)	1996-07-16	低脂血症化合物
CA2067298A1 (fr)	1992-11-02	Phenyl pyrazolidinones en tant que bronchodilatateurs et agents anti-inflammatoires
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
EP0266558A2 (fr)	1988-05-11	5-Alkylbenzimidazoles, leur procédé de préparation et médicaments les contenant
US4654358A (en)	1987-03-31	1,4,5-triphenylimidazol-2-yl mercapto alkanoic acids, useful against inflammation and diseases responding to lipid lowering
FR2566404A1 (fr)	1985-12-27	Nouveaux derives de la 1,4-dihydropyridine, leurs sels, procede pour les preparer, et compositions pharmaceutiques les contenant
US4933458A (en)	1990-06-12	Certain gastric acid secretion inhibiting sulfoxides
MC1970A1 (fr)	1989-09-29	Derives acyles
DE69224507T2 (de)	1998-08-20	Beta-Oxo-Beta-Benzenepropanthioamidderivate
EP1242389A2 (fr)	2002-09-25	Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2,4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant
EP0354788B1 (fr)	1995-09-13	Dérivés d'imidazole
HU198059B (en)	1989-07-28	Process for producing new 4,5-dihydrooxazole derivatives
MC1844A1 (fr)	1988-09-30	Derives de pyrimidine
EP0638568B1 (fr)	1996-10-09	Pipérazines substituées, leur procédé de préparation et les compositions pharmaceutiques les contenant
KR890002291B1 (ko)	1989-06-28	2-알킬벤즈이미다졸 유도체의 제조방법
EP1486503B1 (fr)	2006-11-02	Dérivés de benzothiazine et benzothiadiazine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
EP0683776B1 (fr)	1999-04-07	Heteroarylalkylthiopyridines substituees pour la lutte contre les bacteries helicobacter
FR2511681A1 (fr)	1983-02-25	Procede pour la preparation de derives de 3-exo-methylenecephame
DE69007203T2 (de)	1994-07-28	Imidazolderivate, Verfahren zu deren Herstellung und diese enthaltende Antiulkusmittel.
FR2576900A1 (fr)	1986-08-08	Derives de cyclohepto-imidazole 2-substitue, agents anti-ulcereux et procede pour leur preparation
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
JPS5910351B2 (ja)	1984-03-08	３−オキシ−１，２，４−トリアゾ−ル誘導体の製造方法
FR2508904A2 (fr)	1983-01-07	Nouveaux composes heterocycliques azotes anti-inflammatoires et immunoregulateurs et composition pharmaceutique les contenant