PL115117B1 - Method of manufacture of novel carbonyl substituted 1-sulfonylobenzimidazoles - Google Patents
Method of manufacture of novel carbonyl substituted 1-sulfonylobenzimidazoles Download PDFInfo
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- PL115117B1 PL115117B1 PL1976209626A PL20962676A PL115117B1 PL 115117 B1 PL115117 B1 PL 115117B1 PL 1976209626 A PL1976209626 A PL 1976209626A PL 20962676 A PL20962676 A PL 20962676A PL 115117 B1 PL115117 B1 PL 115117B1
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- 238000000034 method Methods 0.000 title description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 241000700605 Viruses Species 0.000 description 16
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 13
- 231100000331 toxic Toxicity 0.000 description 13
- 230000002588 toxic effect Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000007857 hydrazones Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 208000000474 Poliomyelitis Diseases 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 241000709661 Enterovirus Species 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000003612 virological effect Effects 0.000 description 5
- IYUBCLHILARKQB-UHFFFAOYSA-N 2-sulfonylbenzimidazole Chemical compound C1=CC=CC2=NC(=S(=O)=O)N=C21 IYUBCLHILARKQB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 235000018977 lysine Nutrition 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000005059 halophenyl group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 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
- 229960001413 acetanilide Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 125000005597 hydrazone group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 150000002669 lysines Chemical class 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
- 231100001228 moderately toxic Toxicity 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- ZNCIRTDOBZGUMB-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)propan-1-one Chemical compound C1=CC=C2NC(C(=O)CC)=NC2=C1 ZNCIRTDOBZGUMB-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- FARSPAVQUKTXLF-UHFFFAOYSA-N 1h-benzimidazol-1-ium;chloride Chemical compound Cl.C1=CC=C2NC=NC2=C1 FARSPAVQUKTXLF-UHFFFAOYSA-N 0.000 description 1
- RZMKWQVADPIKCJ-UHFFFAOYSA-N 1h-benzimidazol-2-yl(phenyl)methanone Chemical compound N=1C2=CC=CC=C2NC=1C(=O)C1=CC=CC=C1 RZMKWQVADPIKCJ-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
- APVQNDRXQVWGKX-UHFFFAOYSA-N 2-nitrosoaniline Chemical compound NC1=CC=CC=C1N=O APVQNDRXQVWGKX-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
- 241000283690 Bos taurus Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000709687 Coxsackievirus Species 0.000 description 1
- 241001466953 Echovirus Species 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MVANFYUBACDPQK-UHFFFAOYSA-N NN.ON Chemical compound NN.ON MVANFYUBACDPQK-UHFFFAOYSA-N 0.000 description 1
- CBMMNIZHULUAML-UHFFFAOYSA-N O=CS(C1=NC(C=CC=C2)=C2N1)(=O)=O Chemical class O=CS(C1=NC(C=CC=C2)=C2N1)(=O)=O CBMMNIZHULUAML-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IYVBKVVOHXVKRD-UHFFFAOYSA-N benzimidazol-1-yl(phenyl)methanone Chemical compound C1=NC2=CC=CC=C2N1C(=O)C1=CC=CC=C1 IYVBKVVOHXVKRD-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 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
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical group [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 210000003292 kidney cell Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000009630 liquid culture Methods 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
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229940097496 nasal spray Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 238000006396 nitration reaction Methods 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
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum 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
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 208000011479 upper respiratory tract disease Diseases 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60841575A | 1975-08-28 | 1975-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL115117B1 true PL115117B1 (en) | 1981-03-31 |
Family
ID=24436401
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976209626A PL115117B1 (en) | 1975-08-28 | 1976-08-26 | Method of manufacture of novel carbonyl substituted 1-sulfonylobenzimidazoles |
| PL1976209627A PL110145B1 (en) | 1975-08-28 | 1976-08-26 | Method of producing new derivatives of 1-sulfonylobenzimidazole |
| PL1976192018A PL106947B1 (pl) | 1975-08-28 | 1976-08-26 | Sposob wytwarzania nowych karbonylopodstawionych 1-sulfonylobenzimidazoli |
| PL1976218028A PL112910B1 (en) | 1975-08-28 | 1976-08-26 | Process for preparing novel derivatives of 1-sulfonylobenzimidazole |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976209627A PL110145B1 (en) | 1975-08-28 | 1976-08-26 | Method of producing new derivatives of 1-sulfonylobenzimidazole |
| PL1976192018A PL106947B1 (pl) | 1975-08-28 | 1976-08-26 | Sposob wytwarzania nowych karbonylopodstawionych 1-sulfonylobenzimidazoli |
| PL1976218028A PL112910B1 (en) | 1975-08-28 | 1976-08-26 | Process for preparing novel derivatives of 1-sulfonylobenzimidazole |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4118742A (forum.php) |
| JP (4) | JPS5633392B2 (forum.php) |
| AR (4) | AR219284A1 (forum.php) |
| AT (1) | AT360005B (forum.php) |
| AU (1) | AU502756B2 (forum.php) |
| BE (1) | BE845641A (forum.php) |
| BG (1) | BG27548A3 (forum.php) |
| CA (1) | CA1064501A (forum.php) |
| CH (8) | CH626612A5 (forum.php) |
| DD (1) | DD126518A5 (forum.php) |
| DE (1) | DE2638551A1 (forum.php) |
| DK (1) | DK154764C (forum.php) |
| ES (5) | ES451018A1 (forum.php) |
| FR (1) | FR2321883A1 (forum.php) |
| GB (1) | GB1562812A (forum.php) |
| GR (1) | GR61627B (forum.php) |
| HU (1) | HU173988B (forum.php) |
| IE (1) | IE43531B1 (forum.php) |
| IL (1) | IL50292A (forum.php) |
| MX (1) | MX3654E (forum.php) |
| NL (1) | NL7609414A (forum.php) |
| NZ (1) | NZ181789A (forum.php) |
| PL (4) | PL115117B1 (forum.php) |
| PT (1) | PT65486B (forum.php) |
| RO (5) | RO78122A (forum.php) |
| SU (9) | SU691089A3 (forum.php) |
| YU (2) | YU203476A (forum.php) |
| ZA (1) | ZA765142B (forum.php) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| ZA815698B (en) * | 1980-08-28 | 1983-04-27 | Lilly Co Eli | Intranasal formulation |
| FR2521141A1 (fr) * | 1982-02-09 | 1983-08-12 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| US4463181A (en) * | 1982-04-08 | 1984-07-31 | Eli Lilly And Company | Process for removing sulfonyl groups from benzimidazole isomers |
| IL68297A (en) * | 1982-04-08 | 1986-09-30 | Lilly Co Eli | Process for removing 1-sulfonyl groups from 2-amino-5(6)-substituted benzimidazoles |
| US4434288A (en) | 1982-04-08 | 1984-02-28 | Eli Lilly And Company | Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles |
| US4420479A (en) * | 1982-04-08 | 1983-12-13 | Eli Lilly And Company | Olefinic benzimidazoles, formulations, and antiviral methods |
| US4483986A (en) * | 1982-05-03 | 1984-11-20 | Eli Lilly And Company | 4-Nitrobenzophenone compounds |
| US4629811A (en) * | 1982-05-03 | 1986-12-16 | Eli Lilly And Company | 3-sulfonylamino-4-aminobenzophenone derivatives |
| US4645861A (en) * | 1982-05-03 | 1987-02-24 | Eli Lilly And Company | 3-sulfonylamino-4-amino phenyl acyl derivatives |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| US4501921A (en) * | 1982-11-18 | 1985-02-26 | Eli Lilly And Company | Synthesis of alkylidene intermediates |
| US4435418A (en) * | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| JPS62196293U (forum.php) * | 1986-06-03 | 1987-12-14 | ||
| CA1339133C (en) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| JPS6410894A (en) * | 1987-06-30 | 1989-01-13 | Nitto Koji Kk | Burying propulsion correcting method and device for propulsive pipe for burying hume pipe |
| US5545653A (en) * | 1995-06-07 | 1996-08-13 | Eli Lilly And Company | Anti-viral compounds |
| WO1998055120A1 (en) * | 1997-06-04 | 1998-12-10 | Eli Lilly And Company | Anti-viral compounds |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| US7470723B2 (en) * | 2003-03-05 | 2008-12-30 | Celgene Corporation | Diphenylethylene compounds and uses thereof |
| US8287843B2 (en) * | 2003-06-23 | 2012-10-16 | Colgate-Palmolive Company | Antiplaque oral care compositions |
| SG144809A1 (en) | 2007-01-11 | 2008-08-28 | Millipore U K Ltd | Benzimidazole compounds and their use as chromatographic ligands |
| MY200452A (en) | 2018-08-21 | 2023-12-27 | Kyorin Seiyaku Kk | Bicyclic heteroaromatic ring derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170737A (en) * | 1964-05-27 | 1969-11-12 | Fisons Pest Control Ltd | Substituted Benzimadazoles and their use as Acaricides |
| US3682952A (en) * | 1964-08-04 | 1972-08-08 | Smith Kline French Lab | 5(6)-n-butyl-2-carbomethoxy-benzimidazole |
| DE2034643A1 (de) * | 1970-03-06 | 1971-09-16 | Deutsche Akademie der Wissenschaften zu Berlin, χ 1199 Berlin | Verfahren zur Herstellung von virustatisch wirksamen p-N-Methylnitrosaminophenyl-Verbindungen |
| BE795099A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouvelles 1-acyl-3-aminosulfonyl-2-imino-benzimidazolines, leur procede de preparation et leur application comme fongicides |
| BE795098A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouveaux 1-aminosulfonyl-2-amino-benzimidazoles, leur procede de preparation et leur application comme fongicides |
-
1976
- 1976-08-17 NZ NZ181789A patent/NZ181789A/xx unknown
- 1976-08-17 PT PT65486A patent/PT65486B/pt unknown
- 1976-08-17 MX MX763667U patent/MX3654E/es unknown
- 1976-08-17 GR GR51488A patent/GR61627B/el unknown
- 1976-08-18 HU HU76EI694A patent/HU173988B/hu unknown
- 1976-08-18 IL IL50292A patent/IL50292A/xx unknown
- 1976-08-19 YU YU02034/76A patent/YU203476A/xx unknown
- 1976-08-19 AR AR264377A patent/AR219284A1/es active
- 1976-08-19 AU AU16982/76A patent/AU502756B2/en not_active Expired
- 1976-08-19 CA CA259,487A patent/CA1064501A/en not_active Expired
- 1976-08-24 IE IE1884/76A patent/IE43531B1/en not_active IP Right Cessation
- 1976-08-24 GB GB35153/76A patent/GB1562812A/en not_active Expired
- 1976-08-24 NL NL7609414A patent/NL7609414A/xx not_active Application Discontinuation
- 1976-08-25 RO RO7698734A patent/RO78122A/ro unknown
- 1976-08-25 RO RO7698737A patent/RO78125A/ro unknown
- 1976-08-25 RO RO7687359A patent/RO72313A/ro unknown
- 1976-08-25 RO RO7698736A patent/RO78124A/ro unknown
- 1976-08-25 JP JP10219076A patent/JPS5633392B2/ja not_active Expired
- 1976-08-25 RO RO7698735A patent/RO78123A/ro unknown
- 1976-08-26 SU SU762390305A patent/SU691089A3/ru active
- 1976-08-26 PL PL1976209626A patent/PL115117B1/pl unknown
- 1976-08-26 BG BG034083A patent/BG27548A3/xx unknown
- 1976-08-26 PL PL1976209627A patent/PL110145B1/pl unknown
- 1976-08-26 PL PL1976192018A patent/PL106947B1/pl unknown
- 1976-08-26 PL PL1976218028A patent/PL112910B1/pl unknown
- 1976-08-26 ES ES451018A patent/ES451018A1/es not_active Expired
- 1976-08-26 DK DK386076A patent/DK154764C/da not_active IP Right Cessation
- 1976-08-26 DE DE19762638551 patent/DE2638551A1/de active Granted
- 1976-08-26 AT AT636376A patent/AT360005B/de not_active IP Right Cessation
- 1976-08-26 CH CH1085476A patent/CH626612A5/de not_active IP Right Cessation
- 1976-08-27 FR FR7626026A patent/FR2321883A1/fr active Granted
- 1976-08-27 BE BE1007586A patent/BE845641A/xx not_active IP Right Cessation
- 1976-08-27 DD DD194505A patent/DD126518A5/xx unknown
- 1976-08-27 ZA ZA00765142A patent/ZA765142B/xx unknown
- 1976-12-15 US US05/750,991 patent/US4118742A/en not_active Expired - Lifetime
-
1977
- 1977-02-14 YU YU00390/77A patent/YU39077A/xx unknown
- 1977-08-16 ES ES461644A patent/ES461644A1/es not_active Expired
- 1977-08-16 ES ES461641A patent/ES461641A1/es not_active Expired
- 1977-08-16 ES ES461643A patent/ES461643A1/es not_active Expired
- 1977-08-16 AR AR268810A patent/AR221037A1/es active
- 1977-08-16 ES ES461642A patent/ES461642A1/es not_active Expired
- 1977-09-27 SU SU772524545A patent/SU730300A3/ru active
- 1977-09-28 SU SU772525453A patent/SU685151A3/ru active
- 1977-09-29 SU SU772526201A patent/SU884570A3/ru active
- 1977-09-29 SU SU772527447A patent/SU679140A3/ru active
-
1978
- 1978-06-15 AR AR272626A patent/AR220344A1/es active
- 1978-06-15 AR AR272625A patent/AR221701A1/es active
- 1978-08-16 SU SU782647712A patent/SU730301A3/ru active
- 1978-08-31 SU SU782654600A patent/SU727142A3/ru active
- 1978-10-23 SU SU782676704A patent/SU919593A3/ru active
- 1978-10-24 SU SU782676705A patent/SU784767A3/ru active
-
1980
- 1980-06-30 CH CH503080A patent/CH627753A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502880A patent/CH627455A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502780A patent/CH627748A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502980A patent/CH628035A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513781A patent/CH630917A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513681A patent/CH630376A5/de not_active IP Right Cessation
- 1980-11-26 JP JP55167905A patent/JPS57112389A/ja active Pending
- 1980-11-26 JP JP55167907A patent/JPS591712B2/ja not_active Expired
- 1980-11-26 JP JP55167906A patent/JPS5823876B2/ja not_active Expired
-
1981
- 1981-08-10 CH CH513881A patent/CH631447A5/de not_active IP Right Cessation
Also Published As
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