NO781078L - 5-(4-(diarylmetyl)-1-piperazinylalkyl)benzimidazolderivater - Google Patents
5-(4-(diarylmetyl)-1-piperazinylalkyl)benzimidazolderivaterInfo
- Publication number
- NO781078L NO781078L NO781078A NO781078A NO781078L NO 781078 L NO781078 L NO 781078L NO 781078 A NO781078 A NO 781078A NO 781078 A NO781078 A NO 781078A NO 781078 L NO781078 L NO 781078L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- formula
- piperazinylmethyl
- diphenylmethyl
- compound
- Prior art date
Links
- 150000001556 benzimidazoles Chemical class 0.000 title claims description 7
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 107
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 43
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 39
- -1 alkali metal cyanocyanate Chemical class 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 238000007363 ring formation reaction Methods 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 230000001387 anti-histamine Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 7
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical class NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000000739 antihistaminic agent Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 229910052751 metal Chemical class 0.000 claims description 5
- 239000002184 metal Chemical class 0.000 claims description 5
- OAQDLZSNKCWMDY-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-methylbenzimidazol-2-amine Chemical compound C=1C=C2N(C)C(N)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 OAQDLZSNKCWMDY-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 230000003266 anti-allergic effect Effects 0.000 claims description 4
- 239000000924 antiasthmatic agent Substances 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 230000001088 anti-asthma Effects 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 239000002609 medium Substances 0.000 claims description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 3
- KKMSCNTZDCYNSC-UHFFFAOYSA-N 1-[(4-fluorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 KKMSCNTZDCYNSC-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- ZBKAXLRWIUXFRC-UHFFFAOYSA-N 4-[(4-benzhydrylpiperazin-1-yl)methyl]-1-n-methylbenzene-1,2-diamine Chemical compound C1=C(N)C(NC)=CC=C1CN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 ZBKAXLRWIUXFRC-UHFFFAOYSA-N 0.000 claims description 2
- FBSMOKMUUDYZDO-UHFFFAOYSA-N 4-[(4-benzhydrylpiperazin-1-yl)methyl]-1-n-propylbenzene-1,2-diamine Chemical compound C1=C(N)C(NCCC)=CC=C1CN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 FBSMOKMUUDYZDO-UHFFFAOYSA-N 0.000 claims description 2
- XSWNFQROSUDYLR-UHFFFAOYSA-N 5-(chloromethyl)-2-methyl-1-propylbenzimidazole Chemical compound ClCC1=CC=C2N(CCC)C(C)=NC2=C1 XSWNFQROSUDYLR-UHFFFAOYSA-N 0.000 claims description 2
- JLRQZGHJSRVMEE-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1,2-dimethylbenzimidazole Chemical compound C=1C=C2N(C)C(C)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JLRQZGHJSRVMEE-UHFFFAOYSA-N 0.000 claims description 2
- CVBJSXJXUYWGOM-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-propylbenzimidazole Chemical compound C=1C=C2N(CCC)C=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CVBJSXJXUYWGOM-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- 230000006179 O-acylation Effects 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 238000006114 decarboxylation reaction Methods 0.000 claims description 2
- 238000005695 dehalogenation reaction Methods 0.000 claims description 2
- YGBFFMMKLWVKGU-UHFFFAOYSA-N ethyl butanimidate;hydrochloride Chemical compound [Cl-].CCCC(=[NH2+])OCC YGBFFMMKLWVKGU-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- HWXYYUZBQKVFMV-UHFFFAOYSA-N n-[5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-methylbenzimidazol-2-yl]acetamide Chemical compound C=1C=C2N(C)C(NC(=O)C)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HWXYYUZBQKVFMV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 claims 2
- 238000009795 derivation Methods 0.000 claims 2
- VQLPOIFVOSNNKO-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-ethyl-2-methylbenzimidazole Chemical compound C=1C=C2N(CC)C(C)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 VQLPOIFVOSNNKO-UHFFFAOYSA-N 0.000 claims 1
- PLIIYELREAPEPA-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-ethyl-2-phenylbenzimidazole Chemical compound C=1C=C2N(CC)C(C=3C=CC=CC=3)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 PLIIYELREAPEPA-UHFFFAOYSA-N 0.000 claims 1
- GVGLZMMKVQGJOC-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-methyl-2-phenylbenzimidazole Chemical compound C=1C=C2N(C)C(C=3C=CC=CC=3)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GVGLZMMKVQGJOC-UHFFFAOYSA-N 0.000 claims 1
- AFIGUTZWZNFEMU-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-pentylbenzimidazole Chemical compound C=1C=C2N(CCCCC)C=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AFIGUTZWZNFEMU-UHFFFAOYSA-N 0.000 claims 1
- CZTSLYOHYLWWIP-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-2-(4-fluorophenyl)-1-methylbenzimidazole Chemical compound C=1C=C2N(C)C(C=3C=CC(F)=CC=3)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 CZTSLYOHYLWWIP-UHFFFAOYSA-N 0.000 claims 1
- AKZRGDYUJJORND-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-2-butyl-1-methylbenzimidazole Chemical compound C=1C=C2N(C)C(CCCC)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AKZRGDYUJJORND-UHFFFAOYSA-N 0.000 claims 1
- HZPIHLNXDMOXSD-UHFFFAOYSA-N 5-[(4-benzhydrylpiperazin-1-yl)methyl]-2-methyl-1-propylbenzimidazole Chemical compound C=1C=C2N(CCC)C(C)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HZPIHLNXDMOXSD-UHFFFAOYSA-N 0.000 claims 1
- AAKSUAHVSGLJOW-UHFFFAOYSA-N 5-[[4-[(4-fluorophenyl)-phenylmethyl]piperazin-1-yl]methyl]-2-methyl-1-propylbenzimidazole Chemical compound C=1C=C2N(CCC)C(C)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 AAKSUAHVSGLJOW-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- ARUJJNVNLJPSDO-UHFFFAOYSA-N butanamide;hydrochloride Chemical compound Cl.CCCC(N)=O ARUJJNVNLJPSDO-UHFFFAOYSA-N 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
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- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 75
- 230000008018 melting Effects 0.000 description 75
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- 239000000047 product Substances 0.000 description 52
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- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
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- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- 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
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- C07D235/12—Radicals substituted by oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/30—Nitrogen atoms not forming part of a nitro radical
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- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
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- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
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- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US78265177A | 1977-03-30 | 1977-03-30 | |
US05/866,882 US4179505A (en) | 1977-03-30 | 1978-01-04 | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
NO781078L true NO781078L (no) | 1978-10-03 |
Family
ID=27120026
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO781078A NO781078L (no) | 1977-03-30 | 1978-03-29 | 5-(4-(diarylmetyl)-1-piperazinylalkyl)benzimidazolderivater |
Country Status (25)
Country | Link |
---|---|
US (1) | US4179505A (de) |
JP (1) | JPS53141287A (de) |
AT (1) | AT368136B (de) |
AU (1) | AU517661B2 (de) |
CA (1) | CA1119597A (de) |
DE (1) | DE2813523A1 (de) |
DK (1) | DK135878A (de) |
ES (1) | ES468077A1 (de) |
FI (1) | FI780954A (de) |
FR (1) | FR2385713A1 (de) |
GB (1) | GB1598278A (de) |
GR (1) | GR66124B (de) |
HU (1) | HU180477B (de) |
IE (1) | IE46507B1 (de) |
IL (1) | IL54373A (de) |
IT (1) | IT1103464B (de) |
LU (1) | LU79326A1 (de) |
NL (1) | NL7803312A (de) |
NO (1) | NO781078L (de) |
NZ (1) | NZ186836A (de) |
PH (1) | PH16204A (de) |
PL (1) | PL118310B1 (de) |
PT (1) | PT67855B (de) |
SE (1) | SE7803057L (de) |
SU (1) | SU986297A3 (de) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4243806A (en) * | 1979-06-13 | 1981-01-06 | Janssen Pharmaceutica N.V. | 5-[4-(Diarylmethyl)-1-piperazinylalkyl]benzimidazole derivatives |
EP0034116A3 (de) * | 1980-02-11 | 1981-09-02 | Berlex Laboratories, Inc. | N-(3-Phenoxy-2-hydroxypropyl)benzimidazol-1-alkanamine |
CH653021A5 (fr) * | 1981-04-24 | 1985-12-13 | Delalande Sa | Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant. |
JPS59118765A (ja) * | 1982-12-24 | 1984-07-09 | Fujisawa Pharmaceut Co Ltd | ピペラジン誘導体 |
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 |
EP0189473B1 (de) * | 1984-08-15 | 1992-05-27 | Schering Aktiengesellschaft | Neue dopamin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
US4554287A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | Antihypertensive 7-[2-(dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
US4772705A (en) * | 1985-07-25 | 1988-09-20 | Pennwalt Corporation | Processes for the preparation of trans 1,3,4,6,7,11b-hexahydro-7-aryl-2H-pyrazinol[2,1-a]isoquinolines |
MX173362B (es) * | 1987-03-02 | 1994-02-23 | Pfizer | Compuestos de piperazinil heterociclicos y procedimiento para su preparacion |
US4883795A (en) * | 1988-01-22 | 1989-11-28 | Pfizer Inc. | Piperazinyl-heterocyclic compounds |
FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
US5681954A (en) * | 1993-05-14 | 1997-10-28 | Daiichi Pharmaceutical Co., Ltd. | Piperazine derivatives |
DK0882718T3 (da) * | 1995-12-28 | 2005-12-12 | Astellas Pharma Inc | Benzimidazolderivater |
USH2007H1 (en) * | 1996-01-19 | 2001-12-04 | Fmc Corporation | Insecticidal N-heterocyclylalkyl-or N-[(polycyclyl)alkyl]-N′substituted piperazines |
TW453999B (en) | 1997-06-27 | 2001-09-11 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
NZ508790A (en) * | 1998-05-22 | 2003-10-31 | Scios Inc | Heterocyclic compounds and methods to treat cardiac failure and other disorders |
US6448281B1 (en) * | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
US20090036466A1 (en) * | 2003-12-18 | 2009-02-05 | Jean-Francois Bonfanti | Amino-benzimidazoles derivatives as inhibitors of respiratory syncytial virus replication |
ATE435222T1 (de) * | 2003-12-18 | 2009-07-15 | Tibotec Pharm Ltd | Aminobenzimidazole und benzimidazole als inhibitoren der replikation von respiratory syncytial virus |
US7557108B2 (en) * | 2007-02-07 | 2009-07-07 | Hoffmann-La Roche Inc. | (Indol-4-yl) or (indol-5-yl)-piperazinylmethanones |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2709169A (en) * | 1955-05-24 | X c chs | ||
FR1410958A (fr) * | 1960-05-18 | 1965-09-17 | May & Baker Ltd | Nouvelles nu-phényl pipérazines et leur procédé de préparation |
GB971043A (en) * | 1960-05-18 | 1964-09-30 | May & Baker Ltd | New phenylpiperazine compounds |
US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
US3491098A (en) * | 1967-05-29 | 1970-01-20 | Sterling Drug Inc | 1-((imidazolyl)-lower-alkyl)-4-substituted-piperazines |
-
1978
- 1978-01-04 US US05/866,882 patent/US4179505A/en not_active Expired - Lifetime
- 1978-02-23 PH PH20813A patent/PH16204A/en unknown
- 1978-03-08 CA CA000298497A patent/CA1119597A/en not_active Expired
- 1978-03-16 FR FR7807675A patent/FR2385713A1/fr active Granted
- 1978-03-16 SE SE7803057A patent/SE7803057L/xx unknown
- 1978-03-20 AU AU34313/78A patent/AU517661B2/en not_active Expired
- 1978-03-20 ES ES468077A patent/ES468077A1/es not_active Expired
- 1978-03-22 GB GB11524/78A patent/GB1598278A/en not_active Expired
- 1978-03-28 DK DK135878A patent/DK135878A/da unknown
- 1978-03-28 LU LU79326A patent/LU79326A1/xx unknown
- 1978-03-28 GR GR55810A patent/GR66124B/el unknown
- 1978-03-28 IL IL7854373A patent/IL54373A/xx unknown
- 1978-03-28 IT IT48628/78A patent/IT1103464B/it active
- 1978-03-29 NL NL7803312A patent/NL7803312A/xx not_active Application Discontinuation
- 1978-03-29 NO NO781078A patent/NO781078L/no unknown
- 1978-03-29 JP JP3536678A patent/JPS53141287A/ja active Granted
- 1978-03-29 AT AT0220978A patent/AT368136B/de not_active IP Right Cessation
- 1978-03-29 DE DE19782813523 patent/DE2813523A1/de not_active Ceased
- 1978-03-29 FI FI780954A patent/FI780954A/fi not_active Application Discontinuation
- 1978-03-29 SU SU782595004A patent/SU986297A3/ru active
- 1978-03-29 IE IE608/78A patent/IE46507B1/en unknown
- 1978-03-29 PL PL1978205650A patent/PL118310B1/pl unknown
- 1978-03-30 PT PT67855A patent/PT67855B/pt unknown
- 1978-03-30 HU HU78JA815A patent/HU180477B/hu unknown
- 1978-03-30 NZ NZ186836A patent/NZ186836A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CA1119597A (en) | 1982-03-09 |
GB1598278A (en) | 1981-09-16 |
ES468077A1 (es) | 1979-09-01 |
GR66124B (de) | 1981-01-16 |
PL205650A1 (pl) | 1979-04-09 |
FR2385713A1 (fr) | 1978-10-27 |
SE7803057L (sv) | 1978-10-01 |
AU517661B2 (en) | 1981-08-20 |
NZ186836A (en) | 1981-03-16 |
IT1103464B (it) | 1985-10-14 |
PT67855B (en) | 1980-03-04 |
ATA220978A (de) | 1982-01-15 |
US4179505A (en) | 1979-12-18 |
HU180477B (en) | 1983-03-28 |
SU986297A3 (ru) | 1982-12-30 |
AU3431378A (en) | 1979-09-27 |
AT368136B (de) | 1982-09-10 |
IL54373A (en) | 1982-03-31 |
NL7803312A (nl) | 1978-10-03 |
IE780608L (en) | 1978-09-30 |
JPS53141287A (en) | 1978-12-08 |
FI780954A (fi) | 1978-10-01 |
PT67855A (en) | 1978-04-01 |
IE46507B1 (en) | 1983-06-29 |
LU79326A1 (fr) | 1978-06-29 |
JPS6339591B2 (de) | 1988-08-05 |
DE2813523A1 (de) | 1978-10-05 |
PL118310B1 (en) | 1981-09-30 |
IT7848628A0 (it) | 1978-03-28 |
PH16204A (en) | 1983-08-02 |
DK135878A (da) | 1978-10-01 |
IL54373A0 (en) | 1978-06-15 |
FR2385713B1 (de) | 1983-12-23 |
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