NO872625L - Benzimidazoler og fremgangsmter for deres fremstilling. - Google Patents
Benzimidazoler og fremgangsmter for deres fremstilling.Info
- Publication number
- NO872625L NO872625L NO872625A NO872625A NO872625L NO 872625 L NO872625 L NO 872625L NO 872625 A NO872625 A NO 872625A NO 872625 A NO872625 A NO 872625A NO 872625 L NO872625 L NO 872625L
- Authority
- NO
- Norway
- Prior art keywords
- benzimidazol
- sulfinylmethyl
- methoxy
- dimethylbenzenamine
- thiomethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 11
- 150000001556 benzimidazoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 72
- 150000002431 hydrogen Chemical class 0.000 claims description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- -1 -N<R>13<R>14 Chemical group 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- JBGQTCNAXRURHS-UHFFFAOYSA-N 4-fluoro-n,n-dimethyl-2-[(1-methylbenzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=C(F)C=C1CS(=O)C1=NC2=CC=CC=C2N1C JBGQTCNAXRURHS-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 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 description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- ONGIAJOXDCVPSB-UHFFFAOYSA-N n,n-dimethyl-2-[(1-prop-2-enylbenzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=CC=C2N1CC=C ONGIAJOXDCVPSB-UHFFFAOYSA-N 0.000 claims description 2
- RLJOUVKIYIGHSG-UHFFFAOYSA-N n-cyclohexyl-2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n-methylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=CC=CC=C1N(C)C1CCCCC1 RLJOUVKIYIGHSG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- YTLLTQQUVISZPY-UHFFFAOYSA-N 1-methyl-2-[(2-piperidin-1-ylphenyl)methylsulfinyl]benzimidazole Chemical compound N=1C2=CC=CC=C2N(C)C=1S(=O)CC1=CC=CC=C1N1CCCCC1 YTLLTQQUVISZPY-UHFFFAOYSA-N 0.000 claims 1
- PMEXFRADIMAZQB-UHFFFAOYSA-N 2-[(1-benzyl-5,6-dimethoxybenzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound C1=2C=C(OC)C(OC)=CC=2N=C(S(=O)CC=2C(=CC=CC=2)N(C)C)N1CC1=CC=CC=C1 PMEXFRADIMAZQB-UHFFFAOYSA-N 0.000 claims 1
- XLKRRWTVMMXFPT-UHFFFAOYSA-N 2-[(4,5-dimethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N=1C2=C(OC)C(OC)=CC=C2NC=1SCC1=CC=CC=C1N(C)C XLKRRWTVMMXFPT-UHFFFAOYSA-N 0.000 claims 1
- IZNPKAAVMCXFBM-UHFFFAOYSA-N 2-[(4,5-dimethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C2=C(OC)C(OC)=CC=C2NC=1S(=O)CC1=CC=CC=C1N(C)C IZNPKAAVMCXFBM-UHFFFAOYSA-N 0.000 claims 1
- XOEOZWHUMJMPST-UHFFFAOYSA-N 2-[(4,6-dimethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N1C2=CC(OC)=CC(OC)=C2N=C1S(=O)CC1=CC=CC=C1N(C)C XOEOZWHUMJMPST-UHFFFAOYSA-N 0.000 claims 1
- SLNOGPKSAVINEY-UHFFFAOYSA-N 2-[(4,7-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C(OCC)=CC=C(OCC)C=2NC=1SCC1=CC=CC=C1N(C)C SLNOGPKSAVINEY-UHFFFAOYSA-N 0.000 claims 1
- IJRSXLRAFVIZGA-UHFFFAOYSA-N 2-[(4,7-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C(OCC)=CC=C(OCC)C=2NC=1S(=O)CC1=CC=CC=C1N(C)C IJRSXLRAFVIZGA-UHFFFAOYSA-N 0.000 claims 1
- GOOSOGNTYSCGFD-UHFFFAOYSA-N 2-[(4,7-dimethoxy-1-methylbenzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C(OC)=CC=C(OC)C=2N(C)C=1S(=O)CC1=CC=CC=C1N(C)C GOOSOGNTYSCGFD-UHFFFAOYSA-N 0.000 claims 1
- QLYFEHSAPPWDAW-UHFFFAOYSA-N 2-[(4-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C(OC)=CC=CC=2NC=1SCC1=CC=CC=C1N(C)C QLYFEHSAPPWDAW-UHFFFAOYSA-N 0.000 claims 1
- INKNXNZRPIVYOG-UHFFFAOYSA-N 2-[(4-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C(OC)=CC=CC=2NC=1S(=O)CC1=CC=CC=C1N(C)C INKNXNZRPIVYOG-UHFFFAOYSA-N 0.000 claims 1
- GDUPFYKJDNDRCX-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n,3,6-tetramethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1SCC1=C(C)C=CC(C)=C1N(C)C GDUPFYKJDNDRCX-UHFFFAOYSA-N 0.000 claims 1
- ITLPXFVXZWIZDQ-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n,4-trimethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1SCC1=CC(C)=CC=C1N(C)C ITLPXFVXZWIZDQ-UHFFFAOYSA-N 0.000 claims 1
- ZHLZFLPQEAAEME-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-diethyl-3-methylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1SCC1=C(C)C=CC=C1N(CC)CC ZHLZFLPQEAAEME-UHFFFAOYSA-N 0.000 claims 1
- REKDZAOEALBUPX-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-diethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1SCC1=CC=CC=C1N(CC)CC REKDZAOEALBUPX-UHFFFAOYSA-N 0.000 claims 1
- HFSMEXZBPTXOQV-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1SCC1=CC=CC=C1N(C)C HFSMEXZBPTXOQV-UHFFFAOYSA-N 0.000 claims 1
- YIMLJLZPNKMVST-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-4-methoxy-n,n,3,5-tetramethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=C(C)C(OC)=C(C)C=C1N(C)C YIMLJLZPNKMVST-UHFFFAOYSA-N 0.000 claims 1
- WHBJIWJNUKFXRW-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n,3-trimethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=C(C)C=CC=C1N(C)C WHBJIWJNUKFXRW-UHFFFAOYSA-N 0.000 claims 1
- PDWCTAIBEPIQNG-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n,4-trimethylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=CC(C)=CC=C1N(C)C PDWCTAIBEPIQNG-UHFFFAOYSA-N 0.000 claims 1
- XNVBYZPUHSMERM-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-diethyl-3-methylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=C(C)C=CC=C1N(CC)CC XNVBYZPUHSMERM-UHFFFAOYSA-N 0.000 claims 1
- JPFGGJNYZCWDFL-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-diethyl-5-methylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=CC=C(C)C=C1N(CC)CC JPFGGJNYZCWDFL-UHFFFAOYSA-N 0.000 claims 1
- VAAUPMRWHSVORN-UHFFFAOYSA-N 2-[(5,6-diethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n-ethyl-n-methylaniline Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1S(=O)CC1=CC=CC=C1N(C)CC VAAUPMRWHSVORN-UHFFFAOYSA-N 0.000 claims 1
- VZQLZBODHKDNLQ-UHFFFAOYSA-N 2-[(5,6-dimethoxy-1-methylbenzimidazol-2-yl)sulfinylmethyl]-N,N-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CS(=O)C1=NC2=CC(OC)=C(OC)C=C2N1C VZQLZBODHKDNLQ-UHFFFAOYSA-N 0.000 claims 1
- GNXRJRRHHCYVSN-UHFFFAOYSA-N 2-[(5,6-dimethoxy-1-propylbenzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C2=CC(OC)=C(OC)C=C2N(CCC)C=1S(=O)CC1=CC=CC=C1N(C)C GNXRJRRHHCYVSN-UHFFFAOYSA-N 0.000 claims 1
- DZFOBPWSUZQXAO-UHFFFAOYSA-N 2-[(5,6-dimethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n,3-trimethylaniline Chemical compound N1C=2C=C(OC)C(OC)=CC=2N=C1SCC1=C(C)C=CC=C1N(C)C DZFOBPWSUZQXAO-UHFFFAOYSA-N 0.000 claims 1
- GWQXPLSMYSDEKR-UHFFFAOYSA-N 2-[(5,6-dimethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethyl-5-nitroaniline Chemical compound N1C=2C=C(OC)C(OC)=CC=2N=C1SCC1=CC=C([N+]([O-])=O)C=C1N(C)C GWQXPLSMYSDEKR-UHFFFAOYSA-N 0.000 claims 1
- JFJNSXXRXDLLBV-UHFFFAOYSA-N 2-[(5,6-dimethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethyl-5-nitroaniline Chemical compound N1C=2C=C(OC)C(OC)=CC=2N=C1S(=O)CC1=CC=C([N+]([O-])=O)C=C1N(C)C JFJNSXXRXDLLBV-UHFFFAOYSA-N 0.000 claims 1
- TYDIPNPYUSJBTR-UHFFFAOYSA-N 2-[(5-butoxy-6-ethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N1C=2C=C(OCC)C(OCCCC)=CC=2N=C1S(=O)CC1=CC=CC=C1N(C)C TYDIPNPYUSJBTR-UHFFFAOYSA-N 0.000 claims 1
- UJBOBUSKMUHQIK-UHFFFAOYSA-N 2-[(5-methoxy-1-methylbenzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C2=CC(OC)=CC=C2N(C)C=1S(=O)CC1=CC=CC=C1N(C)C UJBOBUSKMUHQIK-UHFFFAOYSA-N 0.000 claims 1
- QBCRRLYEKWFPBP-UHFFFAOYSA-N 2-[(5-methoxy-6-propoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C=C(OC)C(OCCC)=CC=2NC=1SCC1=CC=CC=C1N(C)C QBCRRLYEKWFPBP-UHFFFAOYSA-N 0.000 claims 1
- LVVMGGRWQIKMKQ-UHFFFAOYSA-N 2-[(5-methoxy-6-propoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N=1C=2C=C(OC)C(OCCC)=CC=2NC=1S(=O)CC1=CC=CC=C1N(C)C LVVMGGRWQIKMKQ-UHFFFAOYSA-N 0.000 claims 1
- GXLXGWCTYJHGTO-UHFFFAOYSA-N 2-[(6-chloro-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1CSC1=NC2=CC=C(Cl)C=C2N1 GXLXGWCTYJHGTO-UHFFFAOYSA-N 0.000 claims 1
- NFTLFMOJYAAGOP-UHFFFAOYSA-N 2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n,3-trimethylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1SCC1=C(C)C=CC=C1N(C)C NFTLFMOJYAAGOP-UHFFFAOYSA-N 0.000 claims 1
- GVTCMDLEVZVGMI-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methylsulfanyl]-1h-benzimidazole-5,6-diol Chemical compound CN(C)C1=CC=CC=C1CSC1=NC2=CC(O)=C(O)C=C2N1 GVTCMDLEVZVGMI-UHFFFAOYSA-N 0.000 claims 1
- IUZJSGLBBGIZFL-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methylsulfanyl]-3h-benzimidazol-5-ol Chemical compound CN(C)C1=CC=CC=C1CSC1=NC2=CC=C(O)C=C2N1 IUZJSGLBBGIZFL-UHFFFAOYSA-N 0.000 claims 1
- JRSGSBZMTCUUNX-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methylsulfinyl]-1h-benzimidazole-5,6-diol Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC(O)=C(O)C=C2N1 JRSGSBZMTCUUNX-UHFFFAOYSA-N 0.000 claims 1
- KHTKCGFXTILPII-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methylsulfinyl]-3h-benzimidazol-5-ol Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC(O)=CC=C2N1 KHTKCGFXTILPII-UHFFFAOYSA-N 0.000 claims 1
- FAKXKNSRLXSKDK-UHFFFAOYSA-N 2-[[2-(dimethylamino)phenyl]methylsulfinyl]-6-methoxy-3h-benzimidazol-5-ol Chemical compound N1C=2C=C(O)C(OC)=CC=2N=C1S(=O)CC1=CC=CC=C1N(C)C FAKXKNSRLXSKDK-UHFFFAOYSA-N 0.000 claims 1
- WRCLXKMAYLMRNC-UHFFFAOYSA-N 4-tert-butyl-2-[(5,6-dimethoxy-1H-benzimidazol-2-yl)sulfinylmethyl]-N,N-dimethylaniline Chemical compound N1C=2C=C(OC)C(OC)=CC=2N=C1S(=O)CC1=CC(C(C)(C)C)=CC=C1N(C)C WRCLXKMAYLMRNC-UHFFFAOYSA-N 0.000 claims 1
- PWYRSMIGOOSNJF-UHFFFAOYSA-N 4-tert-butyl-2-[(5,6-dimethoxy-1h-benzimidazol-2-yl)sulfanylmethyl]-n,n-dimethylaniline Chemical compound N1C=2C=C(OC)C(OC)=CC=2N=C1SCC1=CC(C(C)(C)C)=CC=C1N(C)C PWYRSMIGOOSNJF-UHFFFAOYSA-N 0.000 claims 1
- LPZZIMTTZAFAEJ-UHFFFAOYSA-N 4-tert-butyl-2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]-n,n-dimethylaniline Chemical compound N1C2=CC(OC)=CC=C2N=C1S(=O)CC1=CC(C(C)(C)C)=CC=C1N(C)C LPZZIMTTZAFAEJ-UHFFFAOYSA-N 0.000 claims 1
- JBSADWJWGQGJEK-UHFFFAOYSA-N N-ethyl-2-[(1-methylbenzimidazol-2-yl)sulfinylmethyl]-N-propylaniline Chemical compound CN1C(=NC2=C1C=CC=C2)S(=O)CC1=C(C=CC=C1)N(CCC)CC JBSADWJWGQGJEK-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- IMABGRLEBHHICO-UHFFFAOYSA-N [2-[[2-(dimethylamino)phenyl]methylsulfanyl]-3h-benzimidazol-5-yl]methanol Chemical compound CN(C)C1=CC=CC=C1CSC1=NC2=CC=C(CO)C=C2N1 IMABGRLEBHHICO-UHFFFAOYSA-N 0.000 claims 1
- JMCRQONLVXRKEL-UHFFFAOYSA-N [2-[[2-(dimethylamino)phenyl]methylsulfinyl]-3h-benzimidazol-5-yl]methanol Chemical compound CN(C)C1=CC=CC=C1CS(=O)C1=NC2=CC=C(CO)C=C2N1 JMCRQONLVXRKEL-UHFFFAOYSA-N 0.000 claims 1
- PYGLKCIJJBGAGH-UHFFFAOYSA-N [2-[[2-(dimethylamino)phenyl]methylsulfinyl]-6-methoxy-3h-benzimidazol-5-yl]methanol Chemical compound N1C=2C=C(CO)C(OC)=CC=2N=C1S(=O)CC1=CC=CC=C1N(C)C PYGLKCIJJBGAGH-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- MBGWQJCHUAHIHN-UHFFFAOYSA-N methyl 2-[[2-(dimethylamino)phenyl]methylsulfanyl]-6-methoxy-3h-benzimidazole-5-carboxylate Chemical compound N=1C=2C=C(OC)C(C(=O)OC)=CC=2NC=1SCC1=CC=CC=C1N(C)C MBGWQJCHUAHIHN-UHFFFAOYSA-N 0.000 claims 1
- YOEVFAHGLYKKIM-UHFFFAOYSA-N n,n-diethyl-2-[(6-methoxy-1h-benzimidazol-2-yl)sulfanylmethyl]aniline Chemical compound CCN(CC)C1=CC=CC=C1CSC1=NC2=CC=C(OC)C=C2N1 YOEVFAHGLYKKIM-UHFFFAOYSA-N 0.000 claims 1
- DWVLKYCWQKGOOE-UHFFFAOYSA-N n,n-diethyl-2-[(6-methoxy-1h-benzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound CCN(CC)C1=CC=CC=C1CS(=O)C1=NC2=CC=C(OC)C=C2N1 DWVLKYCWQKGOOE-UHFFFAOYSA-N 0.000 claims 1
- XMFISOKANFYMLK-UHFFFAOYSA-N n,n-dimethyl-2-[(4,5,6-trimethoxy-1h-benzimidazol-2-yl)sulfinylmethyl]aniline Chemical compound N=1C=2C(OC)=C(OC)C(OC)=CC=2NC=1S(=O)CC1=CC=CC=C1N(C)C XMFISOKANFYMLK-UHFFFAOYSA-N 0.000 claims 1
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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
- C07D235/28—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868615417A GB8615417D0 (en) | 1986-06-24 | 1986-06-24 | Heterocyclic compounds |
| GB868615419A GB8615419D0 (en) | 1986-06-24 | 1986-06-24 | Heterocyclic compounds |
| GB868615416A GB8615416D0 (en) | 1986-06-24 | 1986-06-24 | Heterocyclic compounds |
| GB868615418A GB8615418D0 (en) | 1986-06-24 | 1986-06-24 | Heterocyclic compounds |
| GB878702685A GB8702685D0 (en) | 1987-02-06 | 1987-02-06 | Heterocyclic compounds |
| GB878702683A GB8702683D0 (en) | 1987-02-06 | 1987-02-06 | Heterocyclic compounds |
| GB878702686A GB8702686D0 (en) | 1987-02-06 | 1987-02-06 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO872625D0 NO872625D0 (no) | 1987-06-23 |
| NO872625L true NO872625L (no) | 1987-12-28 |
Family
ID=27562753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO872625A NO872625L (no) | 1986-06-24 | 1987-06-23 | Benzimidazoler og fremgangsmter for deres fremstilling. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0251536A1 (fi) |
| KR (1) | KR880000406A (fi) |
| AU (1) | AU7465487A (fi) |
| DK (1) | DK319387A (fi) |
| FI (1) | FI872774A (fi) |
| IL (1) | IL82965A0 (fi) |
| NO (1) | NO872625L (fi) |
| NZ (1) | NZ220770A (fi) |
| PT (1) | PT85153B (fi) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195220B (en) * | 1983-05-03 | 1988-04-28 | Byk Gulden Lomberg Chem Fqb | Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them |
| DK0412529T3 (da) * | 1989-08-10 | 1994-04-05 | Nippon Chemiphar Co | Hidtil ukendte imidazolderivater, fremgangsmåde til fremstilling deraf og midler mod mavesår indeholdende disse |
| WO1997000875A1 (en) * | 1995-06-21 | 1997-01-09 | Korea Research Institute Of Chemical Technology | Benzimidazole derivatives containing fused pyridine |
| WO2000003997A1 (fr) | 1998-07-15 | 2000-01-27 | Teijin Limited | Derives de thiobenzimidazole |
| SE9904044D0 (sv) * | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| US6903126B2 (en) | 2001-07-09 | 2005-06-07 | Schering Ag | 1-Aryl-2-N-, S- or O-substituted benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
| DE10135050A1 (de) * | 2001-07-09 | 2003-02-06 | Schering Ag | 1-Ary1-2-N-, S- oder O-substituierte Benzimidazolderivate, deren Verwendung zur Herstellung von Arzneimitteln sowie diese Derivate enthaltende pharmazeutische Präparate |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0174717B1 (en) * | 1984-07-06 | 1992-01-22 | FISONS plc | Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors |
| AU4640985A (en) * | 1984-08-31 | 1986-03-06 | Nippon Chemiphar Co. Ltd. | Benzimidazole derivatives |
| AU5768886A (en) * | 1985-05-24 | 1986-11-27 | G.D. Searle & Co. | 2-((1-h-benzimidazol-2-ylsulfinyl)methyl)benzenamines |
| US4824856A (en) * | 1985-08-14 | 1989-04-25 | Nippon Chemiphar Co., Ltd. | Method of protecting gastrointestinal tract |
| WO1987001114A2 (en) * | 1985-08-21 | 1987-02-26 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New amines, process for their manufacture, their use and medicines containing them |
| AR243167A1 (es) * | 1985-08-24 | 1993-07-30 | Hoechst Ag | Procedimiento para la preparacion de toluidinas sustituidas. |
-
1987
- 1987-06-12 EP EP87305207A patent/EP0251536A1/en not_active Withdrawn
- 1987-06-19 NZ NZ220770A patent/NZ220770A/xx unknown
- 1987-06-23 DK DK319387A patent/DK319387A/da not_active Application Discontinuation
- 1987-06-23 NO NO872625A patent/NO872625L/no unknown
- 1987-06-23 KR KR1019870006368A patent/KR880000406A/ko not_active Application Discontinuation
- 1987-06-23 FI FI872774A patent/FI872774A/fi not_active IP Right Cessation
- 1987-06-23 IL IL82965A patent/IL82965A0/xx unknown
- 1987-06-24 AU AU74654/87A patent/AU7465487A/en not_active Abandoned
- 1987-06-24 PT PT85153A patent/PT85153B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK319387A (da) | 1987-12-25 |
| NO872625D0 (no) | 1987-06-23 |
| PT85153A (en) | 1987-07-01 |
| IL82965A0 (en) | 1987-12-20 |
| NZ220770A (en) | 1990-02-26 |
| AU7465487A (en) | 1988-01-07 |
| EP0251536A1 (en) | 1988-01-07 |
| PT85153B (pt) | 1990-03-30 |
| FI872774A (fi) | 1987-12-25 |
| DK319387D0 (da) | 1987-06-23 |
| KR880000406A (ko) | 1988-03-25 |
| FI872774A0 (fi) | 1987-06-23 |
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