CH494229A - Verfahren zur Herstellung neuer substituierter Benzimidazole - Google Patents
Verfahren zur Herstellung neuer substituierter BenzimidazoleInfo
- Publication number
- CH494229A CH494229A CH869265A CH869265A CH494229A CH 494229 A CH494229 A CH 494229A CH 869265 A CH869265 A CH 869265A CH 869265 A CH869265 A CH 869265A CH 494229 A CH494229 A CH 494229A
- Authority
- CH
- Switzerland
- Prior art keywords
- chlorobenzyl
- formula
- melting point
- methylbenzimidazole
- piperazinyl
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 238000002844 melting Methods 0.000 claims description 67
- 230000008018 melting Effects 0.000 claims description 67
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
- -1 2-acetoxybenzyl Chemical group 0.000 claims description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 59
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 claims description 51
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 238000001816 cooling Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 229940126062 Compound A Drugs 0.000 claims description 13
- 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 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000001556 benzimidazoles Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 239000003610 charcoal Substances 0.000 claims description 11
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 9
- 239000005457 ice water Substances 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 230000007717 exclusion Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 7
- NEXXSABNSYGLLU-UHFFFAOYSA-N 2-n-[(4-chlorophenyl)methyl]benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCC1=CC=C(Cl)C=C1 NEXXSABNSYGLLU-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- WKFYYUYQBPMMAF-UHFFFAOYSA-N 2-methyl-1h-benzimidazol-3-ium;chloride Chemical compound Cl.C1=CC=C2NC(C)=NC2=C1 WKFYYUYQBPMMAF-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 239000003245 coal Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- OSDZHDOKXGSWOD-UHFFFAOYSA-N nitroxyl;hydrochloride Chemical compound Cl.O=N OSDZHDOKXGSWOD-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- VUZVSFJBGRTRQC-UHFFFAOYSA-N [1-[(4-chlorophenyl)methyl]benzimidazol-2-yl]methanol Chemical compound OCC1=NC2=CC=CC=C2N1CC1=CC=C(Cl)C=C1 VUZVSFJBGRTRQC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229960004275 glycolic acid Drugs 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000001103 potassium chloride Substances 0.000 claims description 4
- 235000011164 potassium chloride Nutrition 0.000 claims description 4
- 238000001665 trituration Methods 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NXGBDZWJDMEMDS-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-4-methyl-2-(4-methylpiperazin-1-yl)benzimidazole Chemical compound ClC1=CC=C(CN2C(=NC3=C2C=CC=C3C)N3CCN(CC3)C)C=C1 NXGBDZWJDMEMDS-UHFFFAOYSA-N 0.000 claims description 2
- AIEZSIAPQGBFRC-UHFFFAOYSA-N 1-benzyl-2-(chloromethyl)benzimidazole Chemical compound ClCC1=NC2=CC=CC=C2N1CC1=CC=CC=C1 AIEZSIAPQGBFRC-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 150000001450 anions Chemical class 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
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012259 ether extract Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- BVJOXYJFOYNQRB-UHFFFAOYSA-N morpholine;hydrobromide Chemical compound Br.C1COCCN1 BVJOXYJFOYNQRB-UHFFFAOYSA-N 0.000 claims description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 239000013585 weight reducing agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 230000003266 anti-allergic effect Effects 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 8
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical group O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 4
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- 229940106681 chloroacetic acid Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 3
- 229960000212 aminophenazone Drugs 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- JWHGQMGWJDFIFU-UHFFFAOYSA-N 2-(chloromethyl)-1-[2-(4-chlorophenyl)ethyl]benzimidazole Chemical compound ClCC1=NC2=CC=CC=C2N1CCC1=CC=C(Cl)C=C1 JWHGQMGWJDFIFU-UHFFFAOYSA-N 0.000 description 2
- YHVDYXUMXWNWBE-UHFFFAOYSA-N 2-[(4-fluorophenyl)methylideneamino]aniline Chemical compound NC1=CC=CC=C1N=CC1=CC=C(F)C=C1 YHVDYXUMXWNWBE-UHFFFAOYSA-N 0.000 description 2
- HJNZFVJICNNNSG-UHFFFAOYSA-N 2-[4-[1-[(4-fluorophenyl)methyl]-4-methylbenzimidazol-2-yl]piperazin-1-yl]ethanol Chemical compound FC1=CC=C(CN2C(=NC3=C2C=CC=C3C)N3CCN(CC3)CCO)C=C1 HJNZFVJICNNNSG-UHFFFAOYSA-N 0.000 description 2
- BNJVETMIOJOROO-UHFFFAOYSA-N 2-n-[(4-fluorophenyl)methyl]benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCC1=CC=C(F)C=C1 BNJVETMIOJOROO-UHFFFAOYSA-N 0.000 description 2
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- NICFDLORAOTXMD-UHFFFAOYSA-N 6-chloro-2-methyl-1h-benzimidazole Chemical compound C1=C(Cl)C=C2NC(C)=NC2=C1 NICFDLORAOTXMD-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- SGJIDKKOCUDTSZ-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-4-methyl-2-(4-methylpiperazin-1-yl)benzimidazole Chemical compound FC1=CC=C(CN2C(=NC3=C2C=CC=C3C)N3CCN(CC3)C)C=C1 SGJIDKKOCUDTSZ-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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 description 1
- BBFFVVDXQAASBK-UHFFFAOYSA-N 2-(chloromethyl)-1-(4-chlorophenyl)benzimidazole Chemical compound ClCC1=NC2=CC=CC=C2N1C1=CC=C(Cl)C=C1 BBFFVVDXQAASBK-UHFFFAOYSA-N 0.000 description 1
- SCXAJOSDWPOPKU-UHFFFAOYSA-N 2-(chloromethyl)-1-[(4-chlorophenyl)methyl]-5-methoxybenzimidazole Chemical compound ClCC1=NC2=CC(OC)=CC=C2N1CC1=CC=C(Cl)C=C1 SCXAJOSDWPOPKU-UHFFFAOYSA-N 0.000 description 1
- CBEHYOCPXGJPLR-UHFFFAOYSA-N 2-(chloromethyl)-1-[(4-fluorophenyl)methyl]benzimidazole Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2N=C1CCl CBEHYOCPXGJPLR-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
- DSEJDYDGUHYJFE-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethyl]aniline Chemical compound NC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 DSEJDYDGUHYJFE-UHFFFAOYSA-N 0.000 description 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- KQEDIXGDOGLVQY-UHFFFAOYSA-N 4-chloro-1-n-[(4-chlorophenyl)methyl]benzene-1,2-diamine Chemical compound NC1=CC(Cl)=CC=C1NCC1=CC=C(Cl)C=C1 KQEDIXGDOGLVQY-UHFFFAOYSA-N 0.000 description 1
- VINKMOYXKNXFNI-UHFFFAOYSA-N 4-chloro-n-[(4-chlorophenyl)methyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NCC1=CC=C(Cl)C=C1 VINKMOYXKNXFNI-UHFFFAOYSA-N 0.000 description 1
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- XEMQSMCMCYMURZ-UHFFFAOYSA-N 5-chloro-2-(chloromethyl)-1-[(4-chlorophenyl)methyl]benzimidazole Chemical compound ClCC1=NC2=CC(Cl)=CC=C2N1CC1=CC=C(Cl)C=C1 XEMQSMCMCYMURZ-UHFFFAOYSA-N 0.000 description 1
- KNQUHMCADKEUNP-UHFFFAOYSA-N 6-methoxy-2-methyl-1h-benzimidazole Chemical compound COC1=CC=C2N=C(C)NC2=C1 KNQUHMCADKEUNP-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OMJPIUBLWYHSLU-UHFFFAOYSA-N CC(C(CC(C=C1)=CC=C1Cl)NCC1=NC(C=CC=C2)=C2N1)N1CCOCC1 Chemical compound CC(C(CC(C=C1)=CC=C1Cl)NCC1=NC(C=CC=C2)=C2N1)N1CCOCC1 OMJPIUBLWYHSLU-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PVGIRFOCCMHTCS-UHFFFAOYSA-N ClC1=CC=C(CN2C(=NC3=C2C=CC=C3)CN3CCNCC3)C=C1 Chemical compound ClC1=CC=C(CN2C(=NC3=C2C=CC=C3)CN3CCNCC3)C=C1 PVGIRFOCCMHTCS-UHFFFAOYSA-N 0.000 description 1
- HKTSIBOYEARAKQ-UHFFFAOYSA-N ClO.N=O Chemical compound ClO.N=O HKTSIBOYEARAKQ-UHFFFAOYSA-N 0.000 description 1
- DNFMJYXRIMLMBZ-UHFFFAOYSA-N Clemizole hydrochloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2N=C1C[NH+]1CCCC1 DNFMJYXRIMLMBZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000002397 Kinins Human genes 0.000 description 1
- 108010093008 Kinins Proteins 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- JCMWSVNNSPUNER-UHFFFAOYSA-N N,O-dimethyltyramine Chemical compound CNCCC1=CC=C(OC)C=C1 JCMWSVNNSPUNER-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229920002055 compound 48/80 Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000058 esterolytic effect Effects 0.000 description 1
- 229960003699 evans blue Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- AIADJAOLOVAOAW-UHFFFAOYSA-N n-(4-methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(C)C=C1 AIADJAOLOVAOAW-UHFFFAOYSA-N 0.000 description 1
- YDKXEQCEEFVZPO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-n-(4-methoxy-2-nitrophenyl)-4-methylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1N(S(=O)(=O)C=1C=CC(C)=CC=1)CC1=CC=C(Cl)C=C1 YDKXEQCEEFVZPO-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESC035513 | 1964-07-23 | ||
| DESC037200 | 1965-06-10 | ||
| DESC037199 | 1965-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH494229A true CH494229A (de) | 1970-07-31 |
Family
ID=27212324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH869265A CH494229A (de) | 1964-07-23 | 1965-06-22 | Verfahren zur Herstellung neuer substituierter Benzimidazole |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3423413A (en:Method) |
| BE (1) | BE667333A (en:Method) |
| BR (1) | BR6571550D0 (en:Method) |
| CH (1) | CH494229A (en:Method) |
| DE (2) | DE1620449C3 (en:Method) |
| DK (1) | DK121376B (en:Method) |
| ES (1) | ES315729A1 (en:Method) |
| GB (1) | GB1115390A (en:Method) |
| IL (1) | IL24007A (en:Method) |
| NL (1) | NL143569B (en:Method) |
| NO (1) | NO122124B (en:Method) |
| SE (1) | SE339228B (en:Method) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3531485A (en) * | 1967-08-14 | 1970-09-29 | American Home Prod | Aryl-substituted diazabicycloalkanes |
| DE2436883C2 (de) * | 1974-07-29 | 1985-08-22 | Schering AG, 1000 Berlin und 4709 Bergkamen | Benzimidazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US4404382A (en) * | 1980-09-17 | 1983-09-13 | The Upjohn Company | Piperazinyl-substituted imidazoles |
| DE3132916A1 (de) * | 1981-08-20 | 1983-03-03 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 1-phenylindazol-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JPS5879983A (ja) | 1981-11-06 | 1983-05-13 | Kanebo Ltd | 新規なベンズイミダゾ−ル誘導体、その製造法およびその医薬組成物 |
| JPS59199679A (ja) * | 1983-04-27 | 1984-11-12 | Kanebo Ltd | 新規なベンズイミダゾ−ル誘導体、その製造法およびその医薬組成物 |
| GB8716313D0 (en) * | 1987-07-10 | 1987-08-19 | Janssen Pharmaceutica Nv | 2-(heterocyclylalkyl)imidazopyridines |
| WO2002036695A1 (de) * | 2000-10-31 | 2002-05-10 | Basf Drucksysteme Gmbh | Verwendung von hyperverzweigten polyurethanen zur herstellung von druckfarben |
| JP2005532991A (ja) | 2002-01-10 | 2005-11-04 | ニューロジェン・コーポレーション | メラニン凝集ホルモン受容体リガンド：置換２−（４−ベンジル−ピペラジン−１−イルメチル）−及び２−（４−ベンジル−ジアゼパン−１−イルメチル）−１ｈ−ベンゾイミダゾールアナログ |
| CA2472470A1 (en) | 2002-01-10 | 2003-07-24 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
| AR066165A1 (es) * | 2007-09-18 | 2009-07-29 | Univ Stanford | Metodos de tratamiento de una infeccion viral de la familia flaviviridae, composiciones para el tratamiento de una infeccion viral de la familia flaviviridae y ensayos de control para identificar composiciones para el tratamiento de una infeccion viral de la familia flaviviridae |
| US9101628B2 (en) * | 2007-09-18 | 2015-08-11 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and composition of treating a flaviviridae family viral infection |
| US8940730B2 (en) | 2007-09-18 | 2015-01-27 | The Board Of Trustees Of The Leland Stanford Junior University | Methods and compositions of treating a Flaviviridae family viral infection |
| CN102448458B (zh) * | 2009-03-18 | 2015-07-22 | 小利兰·斯坦福大学理事会 | 治疗黄病毒科病毒感染的方法和组合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL302847A (en:Method) * | 1963-01-10 |
-
1965
- 1965-06-10 DE DE1620449A patent/DE1620449C3/de not_active Expired
- 1965-06-10 DE DE1620450A patent/DE1620450C3/de not_active Expired
- 1965-06-22 CH CH869265A patent/CH494229A/de not_active IP Right Cessation
- 1965-07-16 GB GB30339/65A patent/GB1115390A/en not_active Expired
- 1965-07-19 DK DK370065AA patent/DK121376B/da unknown
- 1965-07-20 US US473512A patent/US3423413A/en not_active Expired - Lifetime
- 1965-07-22 NO NO159059A patent/NO122124B/no unknown
- 1965-07-22 SE SE09691/65A patent/SE339228B/xx unknown
- 1965-07-22 IL IL24007A patent/IL24007A/en unknown
- 1965-07-23 NL NL656509573A patent/NL143569B/xx unknown
- 1965-07-23 ES ES0315729A patent/ES315729A1/es not_active Expired
- 1965-07-23 BE BE667333A patent/BE667333A/xx unknown
- 1965-07-23 BR BR171550/65A patent/BR6571550D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO122124B (en:Method) | 1971-05-24 |
| US3423413A (en) | 1969-01-21 |
| BE667333A (en:Method) | 1966-01-24 |
| DE1620449B2 (de) | 1973-07-26 |
| NL143569B (nl) | 1974-10-15 |
| DE1470319B2 (de) | 1975-09-18 |
| DE1620450A1 (de) | 1970-02-19 |
| DE1620450B2 (de) | 1975-05-22 |
| DE1620449C3 (de) | 1974-02-21 |
| DE1620449A1 (de) | 1970-04-30 |
| DE1470319A1 (de) | 1969-10-02 |
| SE339228B (en:Method) | 1971-10-04 |
| IL24007A (en) | 1969-06-25 |
| NL6509573A (en:Method) | 1966-01-24 |
| GB1115390A (en) | 1968-05-29 |
| ES315729A1 (es) | 1966-02-16 |
| BR6571550D0 (pt) | 1973-08-14 |
| DK121376B (da) | 1971-10-11 |
| DE1620450C3 (de) | 1976-01-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE897405C (de) | Verfahren zur Herstellung substituierter Piperazine | |
| DE1249281B (en:Method) | ||
| DE1445425A1 (de) | Verfahren zur Herstellung von Piperazinderivaten | |
| CH494229A (de) | Verfahren zur Herstellung neuer substituierter Benzimidazole | |
| DD206991A5 (de) | Verfahren zur herstellung neuer piperazinone | |
| DE2712023A1 (de) | Sulfonamidoaminobenzoesaeurederivate, solche enthaltende arzneimittel sowie verfahren zur herstellung derselben | |
| DE1595920A1 (de) | 4-(omega-Piperazinoalkyl)-pyrazole,ihre Salze und Verfahren zu ihrer Herstellung | |
| DE3442860A1 (de) | 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3- on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE842203C (de) | Verfahren zur Herstellung von neuen Piperazinderivaten | |
| DE2258036A1 (de) | Verfahren zur herstellung von benzo eckige klammer auf b eckige klammer zu thiophen-derivaten | |
| DE3027106A1 (de) | 1-(4-aminobenzyl)-2,3-dioxopiperazin- derivate, saeureadditionssalze derselben und verfahren zur herstellung derselben | |
| DD202563A5 (de) | Verfahren zur herstellung von 1,5-diphenylpyrazolin-3-on-verbindungen | |
| DE3642497A1 (de) | Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte | |
| DE1111208B (de) | Verfahren zur Herstellung von hustenreizstillend wirkenden, basisch substituierten Diphenylcarbinolestern | |
| DD141157A1 (de) | Verfahren zur herstellung von neuen arylaminoimidazolinderivaten | |
| DE1078132B (de) | Verfahren zur Herstellung substituierter Benzimidazole | |
| DE3200258A1 (de) | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| DE1470319C3 (de) | Benzimidazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| EP1220845B1 (de) | Arylsulfonamid-substituierte benzimidazolderivate ihre verwendung als tryptase-inhibitoren | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| DE2024350C3 (de) | 1-(Benzamidoäthyl)-4-(2-pyridyl)piperazine | |
| DE3121137A1 (de) | Neue pyridazino(4,5-b)indole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und deren herstellung" | |
| AT238159B (de) | Verfahren zur Herstellung von neuen Dihalogen-amino-benzylaminen und deren Säureadditionssalzen mit anorganischen oder organischen Säuren | |
| AT236941B (de) | Verfahren zur Herstellung von neuen substituierten Benzimidazolen und deren Säureadditionssalzen | |
| DE2119012A1 (de) | Pyridyl-2-methoxyamin und Pyridyl-3--methoxyamin und ihre Salze sowie ihre Verwendung und Verfahren zur Herstellung derselben |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |