DE2813523A1 - 5-eckige klammer auf 4-(diarylmethyl)-1-piperazinylalkyl eckige klammer zu -benzimidazol-derivate - Google Patents
5-eckige klammer auf 4-(diarylmethyl)-1-piperazinylalkyl eckige klammer zu -benzimidazol-derivateInfo
- Publication number
- DE2813523A1 DE2813523A1 DE19782813523 DE2813523A DE2813523A1 DE 2813523 A1 DE2813523 A1 DE 2813523A1 DE 19782813523 DE19782813523 DE 19782813523 DE 2813523 A DE2813523 A DE 2813523A DE 2813523 A1 DE2813523 A1 DE 2813523A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkyl
- general formula
- diphenylmethyl
- piperazinylmethyl
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- -1 alkoxyphenyl radical Chemical class 0.000 claims description 71
- 239000002253 acid Substances 0.000 claims description 37
- 150000003254 radicals Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 23
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000005840 aryl radicals Chemical class 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 229960001340 histamine Drugs 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical compound CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005333 aroyloxy group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- HJSUAIIUCAMPJQ-UHFFFAOYSA-N 1-propylcyclohexa-3,5-diene-1,2-diamine Chemical compound CCCC1(N)C=CC=CC1N HJSUAIIUCAMPJQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- XKBQWBOFFVJBHI-UHFFFAOYSA-N 1-ethylcyclohexa-3,5-diene-1,2-diamine Chemical compound CCC1(N)C=CC=CC1N XKBQWBOFFVJBHI-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
- 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 description 2
- 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 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
- 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 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 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
- 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
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- 239000000047 product Substances 0.000 description 48
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 41
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- 239000000243 solution Substances 0.000 description 24
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 150000001912 cyanamides Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
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- 208000035475 disorder Diseases 0.000 description 1
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- WYRRCHSAVYXEJB-UHFFFAOYSA-N ethyl 2-hydroxyethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CO WYRRCHSAVYXEJB-UHFFFAOYSA-N 0.000 description 1
- YGBFFMMKLWVKGU-UHFFFAOYSA-N ethyl butanimidate;hydrochloride Chemical compound [Cl-].CCCC(=[NH2+])OCC YGBFFMMKLWVKGU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ATZIPACKTBIFAX-UHFFFAOYSA-N ethyl propanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CC ATZIPACKTBIFAX-UHFFFAOYSA-N 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229940079826 hydrogen sulfite Drugs 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- UTSWOJZNDWBSRH-UHFFFAOYSA-N n-[5-[(4-benzhydrylpiperazin-1-yl)methyl]-1-ethylbenzimidazol-2-yl]acetamide Chemical compound C=1C=C2N(CC)C(NC(C)=O)=NC2=CC=1CN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UTSWOJZNDWBSRH-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000036316 preload Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 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
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 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
- 239000012429 reaction media Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000002227 vasoactive effect Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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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
- 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
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- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- 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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- 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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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C07D235/26—Oxygen atoms
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- 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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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
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- 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
- C07D295/06—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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- C07D295/04—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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- C07D295/04—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
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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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- 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
-
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- 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 |
|---|---|
| DE2813523A1 true DE2813523A1 (de) | 1978-10-05 |
Family
ID=27120026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782813523 Ceased DE2813523A1 (de) | 1977-03-30 | 1978-03-29 | 5-eckige klammer auf 4-(diarylmethyl)-1-piperazinylalkyl eckige klammer zu -benzimidazol-derivate |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4179505A (https=) |
| JP (1) | JPS53141287A (https=) |
| AT (1) | AT368136B (https=) |
| AU (1) | AU517661B2 (https=) |
| CA (1) | CA1119597A (https=) |
| DE (1) | DE2813523A1 (https=) |
| DK (1) | DK135878A (https=) |
| ES (1) | ES468077A1 (https=) |
| FI (1) | FI780954A7 (https=) |
| FR (1) | FR2385713A1 (https=) |
| GB (1) | GB1598278A (https=) |
| GR (1) | GR66124B (https=) |
| HU (1) | HU180477B (https=) |
| IE (1) | IE46507B1 (https=) |
| IL (1) | IL54373A (https=) |
| IT (1) | IT1103464B (https=) |
| LU (1) | LU79326A1 (https=) |
| NL (1) | NL7803312A (https=) |
| NO (1) | NO781078L (https=) |
| NZ (1) | NZ186836A (https=) |
| PH (1) | PH16204A (https=) |
| PL (1) | PL118310B1 (https=) |
| PT (1) | PT67855B (https=) |
| SE (1) | SE7803057L (https=) |
| SU (1) | SU986297A3 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986001204A1 (en) * | 1984-08-15 | 1986-02-27 | Schering Aktiengesellschaft | New dopamine derivatives, process for their production, and their use as medicinal products |
| EP0175525A1 (en) * | 1984-09-12 | 1986-03-26 | Smithkline Beecham Corporation | 7-[2-(Dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
| WO2005058869A1 (en) * | 2003-12-18 | 2005-06-30 | Tibotec Pharmaceuticals Ltd. | Aminobenzimidazoles and benzimidazoles as inhibitors of respiratory syncytial virus replication |
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 |
| IE810250L (en) * | 1980-02-11 | 1981-08-11 | Berlex Lab | N-(3-phenoxy-2-hydroxypropyl) benzimidazole -1-¹alkanamines. |
| US4434174A (en) | 1980-02-11 | 1984-02-28 | Berlex Laboratories, Inc. | Treating cardiovascular diseases with N-(3-phenoxy-2-hydroxypropyl)benzimidazole-1-alkanamines |
| 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 |
| 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 |
| WO1997024334A1 (en) * | 1995-12-28 | 1997-07-10 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| 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 |
| KR100605140B1 (ko) * | 1998-05-22 | 2006-07-28 | 싸이오스 인크 | 심장병 및 다른 질병을 치료하기 위한 헤테로 고리 화합물및 그 치료 방법 |
| US6448281B1 (en) * | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
| RU2381224C2 (ru) * | 2003-12-18 | 2010-02-10 | Тиботек Фармасьютикалз Лтд. | Пиперидинаминобензимидазольные производные как ингибиторы репликации респираторного синцитиального вируса |
| DE602004021135D1 (de) * | 2003-12-18 | 2009-06-25 | Tibotec Pharm Ltd | Aminobenzimidazolderivate als inhibitoren der replikation des respiratory syncytial virus |
| MX2007011292A (es) * | 2005-03-17 | 2007-11-07 | Tibotec Pharm Ltd | 1,3-dihidro-bencimidazol-2-ilidenaminas como inhibidores de replicacion de virus respiratorios sinciciales. |
| US7557108B2 (en) * | 2007-02-07 | 2009-07-07 | Hoffmann-La Roche Inc. | (Indol-4-yl) or (indol-5-yl)-piperazinylmethanones |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2709169A (en) * | 1955-05-24 | X c chs | ||
| US3133069A (en) * | 1960-05-18 | 1964-05-12 | May & Baker Ltd | N-phenylpiperazinyl derivatives of benzimidazole |
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1410958A (fr) * | 1960-05-18 | 1965-09-17 | May & Baker Ltd | Nouvelles nu-phényl pipérazines et leur procédé de préparation |
| 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 SE SE7803057A patent/SE7803057L/xx unknown
- 1978-03-16 FR FR7807675A patent/FR2385713A1/fr active Granted
- 1978-03-20 ES ES468077A patent/ES468077A1/es not_active Expired
- 1978-03-20 AU AU34313/78A patent/AU517661B2/en not_active Expired
- 1978-03-22 GB GB11524/78A patent/GB1598278A/en not_active Expired
- 1978-03-28 IL IL7854373A patent/IL54373A/xx unknown
- 1978-03-28 LU LU79326A patent/LU79326A1/xx unknown
- 1978-03-28 DK DK135878A patent/DK135878A/da unknown
- 1978-03-28 GR GR55810A patent/GR66124B/el unknown
- 1978-03-28 IT IT48628/78A patent/IT1103464B/it active
- 1978-03-29 PL PL1978205650A patent/PL118310B1/pl unknown
- 1978-03-29 NO NO781078A patent/NO781078L/no unknown
- 1978-03-29 SU SU782595004A patent/SU986297A3/ru active
- 1978-03-29 AT AT0220978A patent/AT368136B/de not_active IP Right Cessation
- 1978-03-29 FI FI780954A patent/FI780954A7/fi not_active Application Discontinuation
- 1978-03-29 NL NL7803312A patent/NL7803312A/xx not_active Application Discontinuation
- 1978-03-29 IE IE608/78A patent/IE46507B1/en unknown
- 1978-03-29 DE DE19782813523 patent/DE2813523A1/de not_active Ceased
- 1978-03-29 JP JP3536678A patent/JPS53141287A/ja active Granted
- 1978-03-30 PT PT67855A patent/PT67855B/pt unknown
- 1978-03-30 NZ NZ186836A patent/NZ186836A/xx unknown
- 1978-03-30 HU HU78JA815A patent/HU180477B/hu unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2709169A (en) * | 1955-05-24 | X c chs | ||
| US3133069A (en) * | 1960-05-18 | 1964-05-12 | May & Baker Ltd | N-phenylpiperazinyl derivatives of benzimidazole |
| US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
Non-Patent Citations (2)
| Title |
|---|
| Immunology, 7 (1964), S. 681 |
| J. Gen. Chem. USSR, 33 (1963), S. 2289 |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986001204A1 (en) * | 1984-08-15 | 1986-02-27 | Schering Aktiengesellschaft | New dopamine derivatives, process for their production, and their use as medicinal products |
| EP0175525A1 (en) * | 1984-09-12 | 1986-03-26 | Smithkline Beecham Corporation | 7-[2-(Dialkylamino)ethyl]-4-hydroxy-1,3-benzimidazol-2-ones |
| WO2005058869A1 (en) * | 2003-12-18 | 2005-06-30 | Tibotec Pharmaceuticals Ltd. | Aminobenzimidazoles and benzimidazoles as inhibitors of respiratory syncytial virus replication |
| CN1918146B (zh) * | 2003-12-18 | 2011-09-14 | 泰博特克药品有限公司 | 作为呼吸道合胞病毒复制抑制剂的氨基苯并咪唑和苯并咪唑 |
| US8044073B2 (en) | 2003-12-18 | 2011-10-25 | Tibotec Pharmaceuticals | Aminobenzimidazoles and benzimidazoles as inhibitors of respiratory syncytial virus replication |
Also Published As
| Publication number | Publication date |
|---|---|
| SU986297A3 (ru) | 1982-12-30 |
| PT67855A (en) | 1978-04-01 |
| JPS6339591B2 (https=) | 1988-08-05 |
| PL205650A1 (pl) | 1979-04-09 |
| AU517661B2 (en) | 1981-08-20 |
| FR2385713B1 (https=) | 1983-12-23 |
| IT1103464B (it) | 1985-10-14 |
| FR2385713A1 (fr) | 1978-10-27 |
| IE46507B1 (en) | 1983-06-29 |
| NZ186836A (en) | 1981-03-16 |
| PT67855B (en) | 1980-03-04 |
| AU3431378A (en) | 1979-09-27 |
| PH16204A (en) | 1983-08-02 |
| ES468077A1 (es) | 1979-09-01 |
| JPS53141287A (en) | 1978-12-08 |
| IE780608L (en) | 1978-09-30 |
| DK135878A (da) | 1978-10-01 |
| NO781078L (no) | 1978-10-03 |
| US4179505A (en) | 1979-12-18 |
| HU180477B (en) | 1983-03-28 |
| LU79326A1 (fr) | 1978-06-29 |
| GB1598278A (en) | 1981-09-16 |
| IL54373A0 (en) | 1978-06-15 |
| IL54373A (en) | 1982-03-31 |
| SE7803057L (sv) | 1978-10-01 |
| FI780954A7 (fi) | 1978-10-01 |
| NL7803312A (nl) | 1978-10-03 |
| ATA220978A (de) | 1982-01-15 |
| GR66124B (https=) | 1981-01-16 |
| CA1119597A (en) | 1982-03-09 |
| IT7848628A0 (it) | 1978-03-28 |
| PL118310B1 (en) | 1981-09-30 |
| AT368136B (de) | 1982-09-10 |
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| 8110 | Request for examination paragraph 44 | ||
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Ipc: C07D235/26 |
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| 8128 | New person/name/address of the agent |
Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
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| 8131 | Rejection |