DE2528846A1 - 1-sulfonyl-2,5(6)-substituierte-benzimidazole und verfahren zu ihrer herstellung - Google Patents
1-sulfonyl-2,5(6)-substituierte-benzimidazole und verfahren zu ihrer herstellungInfo
- Publication number
- DE2528846A1 DE2528846A1 DE19752528846 DE2528846A DE2528846A1 DE 2528846 A1 DE2528846 A1 DE 2528846A1 DE 19752528846 DE19752528846 DE 19752528846 DE 2528846 A DE2528846 A DE 2528846A DE 2528846 A1 DE2528846 A1 DE 2528846A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- methyl
- benzimidazole
- ethyl
- substituent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 13
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 2-acetamido-4-methylthiazol-5-yl Chemical group 0.000 claims description 168
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 78
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- 241000700605 Viruses Species 0.000 description 19
- 150000003857 carboxamides Chemical class 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- IYUBCLHILARKQB-UHFFFAOYSA-N 2-sulfonylbenzimidazole Chemical class C1=CC=CC2=NC(=S(=O)=O)N=C21 IYUBCLHILARKQB-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
- YZZHJEUCFVOODM-UHFFFAOYSA-N phenyl 3h-benzimidazole-5-carboxylate Chemical compound C=1C=C2N=CNC2=CC=1C(=O)OC1=CC=CC=C1 YZZHJEUCFVOODM-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- LBSYPJZNFFNVKJ-UHFFFAOYSA-N 4-sulfonylbenzimidazole-2-carboxylic acid Chemical class C1=CC(=S(=O)=O)C2=NC(C(=O)O)=NC2=C1 LBSYPJZNFFNVKJ-UHFFFAOYSA-N 0.000 description 9
- 150000001556 benzimidazoles Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 241000709661 Enterovirus Species 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 6
- XMKCHQVJPWPSPQ-UHFFFAOYSA-N 3h-benzimidazole-5-carbohydrazide Chemical compound NNC(=O)C1=CC=C2N=CNC2=C1 XMKCHQVJPWPSPQ-UHFFFAOYSA-N 0.000 description 6
- FNLQDVXHDNFXIY-UHFFFAOYSA-N 3h-benzimidazole-5-carboxamide Chemical compound NC(=O)C1=CC=C2NC=NC2=C1 FNLQDVXHDNFXIY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- 208000000474 Poliomyelitis Diseases 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001466953 Echovirus Species 0.000 description 3
- 241000991587 Enterovirus C Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- XUMASVHOSXXFLH-UHFFFAOYSA-N N1=CNC2=C1C=CC(=C2)C(=O)OCCCCCCC Chemical compound N1=CNC2=C1C=CC(=C2)C(=O)OCCCCCCC XUMASVHOSXXFLH-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000004987 o-phenylenediamines Chemical class 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LIOBPVZSSVYQSS-UHFFFAOYSA-N 2-(3,4-diaminophenyl)acetic acid Chemical compound NC1=CC=C(CC(O)=O)C=C1N LIOBPVZSSVYQSS-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical class C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000709687 Coxsackievirus Species 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000710185 Mengo virus Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 230000000397 acetylating effect Effects 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
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- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- SSCSARRAUZTRNZ-UHFFFAOYSA-N butyl 3h-benzimidazole-5-carboxylate Chemical compound CCCCOC(=O)C1=CC=C2N=CNC2=C1 SSCSARRAUZTRNZ-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
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- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- 230000032050 esterification Effects 0.000 description 2
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- ZCHQDHMYPQXPQL-UHFFFAOYSA-N ethyl 2-amino-3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)NC2=C1 ZCHQDHMYPQXPQL-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- UQNIYPIQYFMZHQ-UHFFFAOYSA-N heptan-2-yl 3H-benzimidazole-5-carboxylate Chemical compound CC(CCCCC)OC(=O)C=1C=CC2=C(N=CN2)C=1 UQNIYPIQYFMZHQ-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- BECUBVOEPSAYDH-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)acetamide Chemical compound C1=CC=C2NC(NC(=O)C)=NC2=C1 BECUBVOEPSAYDH-UHFFFAOYSA-N 0.000 description 2
- WQCUYPGWPOLMKF-UHFFFAOYSA-N n-(1h-benzimidazol-2-ylsulfonyl)acetamide Chemical compound C1=CC=C2NC(S(=O)(=O)NC(=O)C)=NC2=C1 WQCUYPGWPOLMKF-UHFFFAOYSA-N 0.000 description 2
- ALBBQFWHUCTZFM-UHFFFAOYSA-N n-methyl-1h-benzimidazol-2-amine Chemical class C1=CC=C2NC(NC)=NC2=C1 ALBBQFWHUCTZFM-UHFFFAOYSA-N 0.000 description 2
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- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UZOZFWMQIZLEEP-UHFFFAOYSA-N ethyl 1-(dimethylsulfamoyl)benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(C=NC2=C1)S(=O)(=O)N(C)C UZOZFWMQIZLEEP-UHFFFAOYSA-N 0.000 description 1
- MSOQAJPCWVCQNP-UHFFFAOYSA-N ethyl 2-[2-acetamido-1-(dimethylsulfamoyl)benzimidazol-5-yl]acetate Chemical compound C(C)OC(CC1=CC2=C(N(C(=N2)NC(C)=O)S(=O)(=O)N(C)C)C=C1)=O MSOQAJPCWVCQNP-UHFFFAOYSA-N 0.000 description 1
- VEHDNTZHJNLCKD-UHFFFAOYSA-N ethyl 2-amino-1-propan-2-ylsulfonylbenzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N(S(=O)(=O)C(C)C)C(N)=NC2=C1 VEHDNTZHJNLCKD-UHFFFAOYSA-N 0.000 description 1
- VIAONDSLDLNKQJ-UHFFFAOYSA-N ethyl 2-amino-3-(dimethylsulfamoyl)benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)N(S(=O)(=O)N(C)C)C2=C1 VIAONDSLDLNKQJ-UHFFFAOYSA-N 0.000 description 1
- PKZCCPWJLSEIFR-UHFFFAOYSA-N ethyl 2-amino-3-propan-2-ylsulfonylbenzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)N(S(=O)(=O)C(C)C)C2=C1 PKZCCPWJLSEIFR-UHFFFAOYSA-N 0.000 description 1
- HVEHULVPFMWQAB-UHFFFAOYSA-N ethyl 2-methyl-3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(C)NC2=C1 HVEHULVPFMWQAB-UHFFFAOYSA-N 0.000 description 1
- AEEPWPZOSRBWSK-UHFFFAOYSA-N ethyl 3-(dimethylsulfamoyl)-2-methylbenzimidazole-5-carboxylate Chemical compound CN(S(=O)(=O)N1C(=NC2=C1C=C(C=C2)C(=O)OCC)C)C AEEPWPZOSRBWSK-UHFFFAOYSA-N 0.000 description 1
- HUOIDCCHUGUZQS-UHFFFAOYSA-N ethyl 3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CNC2=C1 HUOIDCCHUGUZQS-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- HCEWKFAGNGVVBE-UHFFFAOYSA-N n-(4-cyano-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1[N+]([O-])=O HCEWKFAGNGVVBE-UHFFFAOYSA-N 0.000 description 1
- UFKRTEWFEYWIHD-UHFFFAOYSA-N n-(4-cyanophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C#N)C=C1 UFKRTEWFEYWIHD-UHFFFAOYSA-N 0.000 description 1
- XHJXYBIIUUFVLB-UHFFFAOYSA-N n-[4-(cyanomethyl)-2-nitrophenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CC#N)C=C1[N+]([O-])=O XHJXYBIIUUFVLB-UHFFFAOYSA-N 0.000 description 1
- SPAOQNOLRMENDZ-UHFFFAOYSA-N n-[4-(cyanomethyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(CC#N)C=C1 SPAOQNOLRMENDZ-UHFFFAOYSA-N 0.000 description 1
- ZSWXMTQLPYVTLZ-UHFFFAOYSA-N n-ethyl-n-methylsulfamoyl chloride Chemical compound CCN(C)S(Cl)(=O)=O ZSWXMTQLPYVTLZ-UHFFFAOYSA-N 0.000 description 1
- AXEVAAYUGSXTBP-UHFFFAOYSA-N n-morpholin-4-ylsulfamoyl chloride Chemical compound ClS(=O)(=O)NN1CCOCC1 AXEVAAYUGSXTBP-UHFFFAOYSA-N 0.000 description 1
- YKZZVZBDJFSHCH-UHFFFAOYSA-N n-propan-2-yl-1h-benzimidazole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)NC(C)C)=NC2=C1 YKZZVZBDJFSHCH-UHFFFAOYSA-N 0.000 description 1
- CLRRIVRWTAYDKB-UHFFFAOYSA-N n-sulfonyl-1h-benzimidazole-2-carboxamide Chemical class C1=CC=C2NC(C(N=S(=O)=O)=O)=NC2=C1 CLRRIVRWTAYDKB-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 1
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
- HLYVNXRHROOICH-UHFFFAOYSA-N o-propan-2-ylhydroxylamine Chemical compound CC(C)ON HLYVNXRHROOICH-UHFFFAOYSA-N 0.000 description 1
- PRAARDGLAWZXML-UHFFFAOYSA-N o-propylhydroxylamine Chemical compound CCCON PRAARDGLAWZXML-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- NIQBEHHIVMUCAP-UHFFFAOYSA-N octan-2-yl 3H-benzimidazole-5-carboxylate Chemical compound CC(CCCCCC)OC(=O)C=1C=CC2=C(N=CN2)C=1 NIQBEHHIVMUCAP-UHFFFAOYSA-N 0.000 description 1
- HPBUKYDVWBGMMI-UHFFFAOYSA-N octyl 3H-benzimidazole-5-carboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C2NC=NC2=C1 HPBUKYDVWBGMMI-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- XKWKNIAFDXSEIF-UHFFFAOYSA-M potassium;2-amino-1-(diethylsulfamoyl)benzimidazole-5-carboxylate Chemical compound [K+].[O-]C(=O)C1=CC=C2N(S(=O)(=O)N(CC)CC)C(N)=NC2=C1 XKWKNIAFDXSEIF-UHFFFAOYSA-M 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XHKHMYOOUONOMF-UHFFFAOYSA-N propan-2-yl 2-[2-amino-1-(benzenesulfonyl)benzimidazol-5-yl]propanoate Chemical compound C(C)(C)OC(C(C)C1=CC2=C(N(C(=N2)N)S(=O)(=O)C2=CC=CC=C2)C=C1)=O XHKHMYOOUONOMF-UHFFFAOYSA-N 0.000 description 1
- FLZKKDQVPIYZKN-UHFFFAOYSA-N propan-2-yl 3h-benzimidazole-5-carboxylate Chemical compound CC(C)OC(=O)C1=CC=C2N=CNC2=C1 FLZKKDQVPIYZKN-UHFFFAOYSA-N 0.000 description 1
- MVNLXMJYSQIPEP-UHFFFAOYSA-N propyl 3h-benzimidazole-5-carboxylate Chemical compound CCCOC(=O)C1=CC=C2N=CNC2=C1 MVNLXMJYSQIPEP-UHFFFAOYSA-N 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical class NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- FGGLFMYNQAIUFS-UHFFFAOYSA-N tert-butyl 2-(2-amino-1-morpholin-4-ylsulfonylbenzimidazol-5-yl)acetate Chemical compound C(C)(C)(C)OC(CC1=CC2=C(N(C(=N2)N)S(=O)(=O)N2CCOCC2)C=C1)=O FGGLFMYNQAIUFS-UHFFFAOYSA-N 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
- YSPWSQNKRBSICH-UHFFFAOYSA-N thiophene-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C=1C=CSC=1 YSPWSQNKRBSICH-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48484174A | 1974-07-01 | 1974-07-01 | |
| US57420275A | 1975-05-08 | 1975-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2528846A1 true DE2528846A1 (de) | 1976-01-22 |
Family
ID=27048159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528846 Withdrawn DE2528846A1 (de) | 1974-07-01 | 1975-06-27 | 1-sulfonyl-2,5(6)-substituierte-benzimidazole und verfahren zu ihrer herstellung |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS51125078A (en, 2012) |
| AR (1) | AR212431A1 (en, 2012) |
| AT (1) | AT344158B (en, 2012) |
| BG (1) | BG27083A3 (en, 2012) |
| CA (1) | CA1026335A (en, 2012) |
| CH (1) | CH617428A5 (en, 2012) |
| DD (1) | DD121109A5 (en, 2012) |
| DE (1) | DE2528846A1 (en, 2012) |
| DK (1) | DK140313B (en, 2012) |
| ES (1) | ES439049A1 (en, 2012) |
| FR (1) | FR2276821A1 (en, 2012) |
| GB (1) | GB1511724A (en, 2012) |
| HU (1) | HU172941B (en, 2012) |
| IE (1) | IE41394B1 (en, 2012) |
| IL (1) | IL47587A (en, 2012) |
| NL (1) | NL7507840A (en, 2012) |
| PH (1) | PH14623A (en, 2012) |
| PL (1) | PL97785B1 (en, 2012) |
| RO (1) | RO68748A (en, 2012) |
| SE (1) | SE415254B (en, 2012) |
| SU (1) | SU786892A3 (en, 2012) |
| YU (1) | YU164075A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2706227A1 (de) * | 1976-12-15 | 1978-06-22 | Lilly Co Eli | Neue 1-sulfonyl-5(6)-subst.-benzimidazole und verfahren zu ihrer herstellung |
| US7820682B2 (en) | 2002-10-03 | 2010-10-26 | Ono Pharmaceutical Co., Ltd. | LPA receptor antagonist |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8504818D0 (en) * | 1985-02-25 | 1985-03-27 | Imperial Chemical Industries Plc | Extraction of metal values |
| JPS625966A (ja) * | 1985-07-03 | 1987-01-12 | Nippon Shinyaku Co Ltd | ベンズイミダゾ−ル誘導体 |
-
1975
- 1975-06-25 JP JP50079313A patent/JPS51125078A/ja active Pending
- 1975-06-26 YU YU01640/75A patent/YU164075A/xx unknown
- 1975-06-27 DK DK292175AA patent/DK140313B/da unknown
- 1975-06-27 RO RO7582673A patent/RO68748A/ro unknown
- 1975-06-27 DE DE19752528846 patent/DE2528846A1/de not_active Withdrawn
- 1975-06-27 IL IL47587A patent/IL47587A/xx unknown
- 1975-06-27 GB GB27406/75A patent/GB1511724A/en not_active Expired
- 1975-06-27 CA CA230,418A patent/CA1026335A/en not_active Expired
- 1975-06-30 SE SE7507482A patent/SE415254B/xx unknown
- 1975-06-30 HU HU75EI00000632A patent/HU172941B/hu unknown
- 1975-06-30 CH CH849875A patent/CH617428A5/de not_active IP Right Cessation
- 1975-06-30 IE IE1442/75A patent/IE41394B1/xx unknown
- 1975-06-30 AT AT499475A patent/AT344158B/de not_active IP Right Cessation
- 1975-06-30 PL PL1975181664A patent/PL97785B1/pl unknown
- 1975-07-01 SU SU752149409A patent/SU786892A3/ru active
- 1975-07-01 ES ES439049A patent/ES439049A1/es not_active Expired
- 1975-07-01 BG BG030436A patent/BG27083A3/xx unknown
- 1975-07-01 FR FR7520653A patent/FR2276821A1/fr active Granted
- 1975-07-01 NL NL7507840A patent/NL7507840A/xx not_active Application Discontinuation
- 1975-07-01 DD DD186999A patent/DD121109A5/xx unknown
- 1975-07-01 AR AR259433A patent/AR212431A1/es active
-
1977
- 1977-11-11 PH PH20425A patent/PH14623A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2706227A1 (de) * | 1976-12-15 | 1978-06-22 | Lilly Co Eli | Neue 1-sulfonyl-5(6)-subst.-benzimidazole und verfahren zu ihrer herstellung |
| US7820682B2 (en) | 2002-10-03 | 2010-10-26 | Ono Pharmaceutical Co., Ltd. | LPA receptor antagonist |
| US8124645B2 (en) * | 2002-10-03 | 2012-02-28 | Ono Pharmaceutical Co., Ltd. | LPA receptor antagonist |
| US20120088782A1 (en) * | 2002-10-03 | 2012-04-12 | Ono Pharmaceutical Co., Ltd. | Lpa receptor antagonist |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA499475A (de) | 1977-11-15 |
| NL7507840A (nl) | 1976-01-05 |
| CA1026335A (en) | 1978-02-14 |
| GB1511724A (en) | 1978-05-24 |
| DK140313B (da) | 1979-07-30 |
| FR2276821B1 (en, 2012) | 1982-03-05 |
| SE415254B (sv) | 1980-09-22 |
| AU8253675A (en) | 1977-01-06 |
| FR2276821A1 (fr) | 1976-01-30 |
| PL97785B1 (pl) | 1978-03-30 |
| SU786892A3 (ru) | 1980-12-07 |
| HU172941B (hu) | 1979-01-28 |
| CH617428A5 (en) | 1980-05-30 |
| RO68748A (ro) | 1980-06-15 |
| IE41394B1 (en) | 1979-12-19 |
| PH14623A (en) | 1981-10-12 |
| ES439049A1 (es) | 1977-05-16 |
| BG27083A3 (bg) | 1979-08-15 |
| DK292175A (en, 2012) | 1976-01-02 |
| AR212431A1 (es) | 1978-07-14 |
| AT344158B (de) | 1978-07-10 |
| DD121109A5 (en, 2012) | 1976-07-12 |
| SE7507482L (sv) | 1976-01-02 |
| IL47587A0 (en) | 1975-08-31 |
| JPS51125078A (en) | 1976-11-01 |
| DK140313C (en, 2012) | 1979-12-17 |
| IE41394L (en) | 1976-01-01 |
| YU164075A (en) | 1982-02-28 |
| IL47587A (en) | 1978-08-31 |
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