JP2004530731A - 1−アルキル−2−アリール−ベンズイミダゾール誘導体、医薬製剤の製造のためへのそれらの使用、及びそれらの誘導体を含む医薬製剤 - Google Patents
1−アルキル−2−アリール−ベンズイミダゾール誘導体、医薬製剤の製造のためへのそれらの使用、及びそれらの誘導体を含む医薬製剤 Download PDFInfo
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- JP2004530731A JP2004530731A JP2003510034A JP2003510034A JP2004530731A JP 2004530731 A JP2004530731 A JP 2004530731A JP 2003510034 A JP2003510034 A JP 2003510034A JP 2003510034 A JP2003510034 A JP 2003510034A JP 2004530731 A JP2004530731 A JP 2004530731A
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- Prior art keywords
- benzimidazole
- phenyl
- oxy
- pentyl
- group
- 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.)
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title description 4
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 230000002025 microglial effect Effects 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 230000020411 cell activation Effects 0.000 claims abstract description 8
- -1 methanediylbisoxy Chemical group 0.000 claims description 118
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 150000001556 benzimidazoles Chemical class 0.000 claims description 49
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- LRIULHLUCYGQSS-UHFFFAOYSA-N methyl 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxyhexanoate Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 LRIULHLUCYGQSS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- RMJIXEYAHYJJJS-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxy-n-(3-methoxypropyl)hexanamide Chemical compound COCCCN1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=C(C#N)C=C1 RMJIXEYAHYJJJS-UHFFFAOYSA-N 0.000 claims description 3
- ITKZDXQDKWVUOR-UHFFFAOYSA-N 6-[2-(4-tert-butylphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxy-n-(3-methoxypropyl)hexanamide Chemical compound COCCCN1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=C(C(C)(C)C)C=C1 ITKZDXQDKWVUOR-UHFFFAOYSA-N 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 206010010904 Convulsion Diseases 0.000 claims description 3
- RGHBYOXTIZJRDL-UHFFFAOYSA-N methyl 6-(3-benzyl-2-phenylbenzimidazol-5-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1CN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RGHBYOXTIZJRDL-UHFFFAOYSA-N 0.000 claims description 3
- JFHLXZUUDMWTCO-UHFFFAOYSA-N methyl 6-[2-(4-cyanophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(C#N)C=C1 JFHLXZUUDMWTCO-UHFFFAOYSA-N 0.000 claims description 3
- KXDRAQDORWXVBA-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-(3-morpholin-4-ylpropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1COCCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 KXDRAQDORWXVBA-UHFFFAOYSA-N 0.000 claims description 3
- PAUFKJBHZIPPQY-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-(4-phenylpiperazin-1-yl)propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 PAUFKJBHZIPPQY-UHFFFAOYSA-N 0.000 claims description 3
- MEQLPXQFWHNCKG-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=CC=C1 MEQLPXQFWHNCKG-UHFFFAOYSA-N 0.000 claims description 3
- FUBCRGSPXAFASB-UHFFFAOYSA-N methyl 6-[3-[3-[acetyl(methyl)amino]propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound CC(=O)N(C)CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 FUBCRGSPXAFASB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- HHMZXHSSRHIPJS-UHFFFAOYSA-N 6-(3-benzyl-2-phenylbenzimidazol-5-yl)oxyhexanoic acid Chemical compound C=1C=CC=CC=1CN1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 HHMZXHSSRHIPJS-UHFFFAOYSA-N 0.000 claims description 2
- IHNJMUYVRZNMFL-UHFFFAOYSA-N 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxy-n,n-dimethylhexanamide Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)N(C)C)=CC=C2N=C1C1=CC=CC=C1 IHNJMUYVRZNMFL-UHFFFAOYSA-N 0.000 claims description 2
- HKJWTJDBBPYTNL-UHFFFAOYSA-N 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxy-n-(3-methoxypropyl)hexanamide Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=CC=C1 HKJWTJDBBPYTNL-UHFFFAOYSA-N 0.000 claims description 2
- CLLMEAWOIHEHFU-UHFFFAOYSA-N 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxy-n-(3-methylbutyl)hexanamide Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)NCCC(C)C)=CC=C2N=C1C1=CC=CC=C1 CLLMEAWOIHEHFU-UHFFFAOYSA-N 0.000 claims description 2
- KBGUQMIVASIIDV-UHFFFAOYSA-N 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxy-n-propan-2-ylhexanamide Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)NC(C)C)=CC=C2N=C1C1=CC=CC=C1 KBGUQMIVASIIDV-UHFFFAOYSA-N 0.000 claims description 2
- GNZPFCDJPRHNFQ-UHFFFAOYSA-N 6-(3-cyclohexyl-2-phenylbenzimidazol-5-yl)oxyhexanoic acid Chemical compound C1CCCCC1N1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 GNZPFCDJPRHNFQ-UHFFFAOYSA-N 0.000 claims description 2
- UMODGAQFHCCUKH-UHFFFAOYSA-N 6-[2-(1H-indol-3-yl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound C1=CC=C2C(C=3N(C4=CC(OCCCCCC(O)=O)=CC=C4N=3)CCCOC)=CNC2=C1 UMODGAQFHCCUKH-UHFFFAOYSA-N 0.000 claims description 2
- YPDPQNFDJIQOEX-UHFFFAOYSA-N 6-[2-(4-cyanophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(C#N)C=C1 YPDPQNFDJIQOEX-UHFFFAOYSA-N 0.000 claims description 2
- YQDNKAHOFNWMLC-UHFFFAOYSA-N 6-[2-(4-tert-butylphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(C(C)(C)C)C=C1 YQDNKAHOFNWMLC-UHFFFAOYSA-N 0.000 claims description 2
- OKLSYPCHWCHAIK-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=CC=C1 OKLSYPCHWCHAIK-UHFFFAOYSA-N 0.000 claims description 2
- MPMMWDMEYDMWKB-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-pyridin-3-ylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=CN=C1 MPMMWDMEYDMWKB-UHFFFAOYSA-N 0.000 claims description 2
- JNQUYIJIDBFKJI-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-pyridin-4-ylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=NC=C1 JNQUYIJIDBFKJI-UHFFFAOYSA-N 0.000 claims description 2
- OUDJGPRRQLSYCG-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-thiophen-2-ylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=CS1 OUDJGPRRQLSYCG-UHFFFAOYSA-N 0.000 claims description 2
- GMZHJUOAXAXURF-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-thiophen-3-ylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C=1C=CSC=1 GMZHJUOAXAXURF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- DKLHSCKFBOPALI-UHFFFAOYSA-N methyl 6-[1-(cyclohexylmethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1C1=NC2=CC(OCCCCCC(=O)OC)=CC=C2N1CC1CCCCC1 DKLHSCKFBOPALI-UHFFFAOYSA-N 0.000 claims description 2
- LDDLNQSWRIMWMI-UHFFFAOYSA-N methyl 6-[2-(1H-indol-3-yl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1=CC=C2C(C=3N(C4=CC(OCCCCCC(=O)OC)=CC=C4N=3)CCCOC)=CNC2=C1 LDDLNQSWRIMWMI-UHFFFAOYSA-N 0.000 claims description 2
- SSZZERHKYXONDR-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-(4-pyridin-2-ylpiperazin-1-yl)propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C1CN(C=2N=CC=CC=2)CCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 SSZZERHKYXONDR-UHFFFAOYSA-N 0.000 claims description 2
- NQRKLNCBUQPWTN-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 NQRKLNCBUQPWTN-UHFFFAOYSA-N 0.000 claims description 2
- LKPKPWVBDJOXOY-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-[methyl(3-methylsulfanylpropanoyl)amino]propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound CSCCC(=O)N(C)CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 LKPKPWVBDJOXOY-UHFFFAOYSA-N 0.000 claims description 2
- TUFNYNADVSNXOT-UHFFFAOYSA-N methyl 6-[2-(4-tert-butylphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(C(C)(C)C)C=C1 TUFNYNADVSNXOT-UHFFFAOYSA-N 0.000 claims description 2
- SGSJYGBZBAYWMQ-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-pyridin-3-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=CN=C1 SGSJYGBZBAYWMQ-UHFFFAOYSA-N 0.000 claims description 2
- MKHAEOJLABGZLU-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-pyridin-4-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=NC=C1 MKHAEOJLABGZLU-UHFFFAOYSA-N 0.000 claims description 2
- KWNGXBFAEJFQKK-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-thiophen-2-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=CS1 KWNGXBFAEJFQKK-UHFFFAOYSA-N 0.000 claims description 2
- UFVFOISUPZLVLT-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-thiophen-3-ylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C=1C=CSC=1 UFVFOISUPZLVLT-UHFFFAOYSA-N 0.000 claims description 2
- PNBPAFKPELCSRJ-UHFFFAOYSA-N methyl 6-[3-(cyclohexylmethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C1CCCCC1CN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 PNBPAFKPELCSRJ-UHFFFAOYSA-N 0.000 claims description 2
- GEXKUHKIWJFYRS-UHFFFAOYSA-N methyl 6-[3-[3-(diethylamino)propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCN(CC)CC)C=1C1=CC=C(OC)C=C1 GEXKUHKIWJFYRS-UHFFFAOYSA-N 0.000 claims description 2
- PZUFVSVYRGHSRY-UHFFFAOYSA-N methyl 6-[3-[3-[(2-methoxyacetyl)-methylamino]propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCN(C)C(=O)COC)C=1C1=CC=C(OC)C=C1 PZUFVSVYRGHSRY-UHFFFAOYSA-N 0.000 claims description 2
- CBSGFSOURRXBFI-UHFFFAOYSA-N methyl 6-[3-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 CBSGFSOURRXBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- FRCCULHHQGRNLO-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]-1h-benzimidazole Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=NC2=CC=CC=C2N1 FRCCULHHQGRNLO-UHFFFAOYSA-N 0.000 claims 1
- ARBOZSHSTKHBFN-UHFFFAOYSA-N 6-(2-phenyl-3-propan-2-ylbenzimidazol-5-yl)oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(C(C)C)C=1C1=CC=CC=C1 ARBOZSHSTKHBFN-UHFFFAOYSA-N 0.000 claims 1
- BPERYSXAZVTDEJ-UHFFFAOYSA-N 6-[1-(carboxymethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC(OCCCCCC(=O)O)=CC=C2N(CC(O)=O)C=1C1=CC=CC=C1 BPERYSXAZVTDEJ-UHFFFAOYSA-N 0.000 claims 1
- FWZDLNHQKUCTAC-UHFFFAOYSA-N 6-[1-[2-(diethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC(OCCCCCC(O)=O)=CC=C2N(CC(=O)N(CC)CC)C=1C1=CC=CC=C1 FWZDLNHQKUCTAC-UHFFFAOYSA-N 0.000 claims 1
- OGVVKQLIONJIHK-UHFFFAOYSA-N 6-[1-[2-(dimethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC(OCCCCCC(O)=O)=CC=C2N(CC(=O)N(C)C)C=1C1=CC=CC=C1 OGVVKQLIONJIHK-UHFFFAOYSA-N 0.000 claims 1
- WDBPXDYBPRXCQQ-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxy-n-(3-methoxypropyl)hexanamide Chemical compound COCCCN1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=C(F)C=C1 WDBPXDYBPRXCQQ-UHFFFAOYSA-N 0.000 claims 1
- ZEJCKBHPQNAROT-UHFFFAOYSA-N 6-[2-(4-fluorophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(F)C=C1 ZEJCKBHPQNAROT-UHFFFAOYSA-N 0.000 claims 1
- RTLJHXOOKDBXLM-UHFFFAOYSA-N 6-[2-(4-hydroxyphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(O)C=C1 RTLJHXOOKDBXLM-UHFFFAOYSA-N 0.000 claims 1
- UDWWFUWSOLCJIU-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxy-n-(3-methoxypropyl)hexanamide Chemical compound COCCCN1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=C(OC)C=C1 UDWWFUWSOLCJIU-UHFFFAOYSA-N 0.000 claims 1
- WRHLLRJKNFZKNT-UHFFFAOYSA-N 6-[2-(4-methoxyphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(OC)C=C1 WRHLLRJKNFZKNT-UHFFFAOYSA-N 0.000 claims 1
- UQBWVILSXNUIKE-UHFFFAOYSA-N 6-[2-[4-(dimethylamino)phenyl]-3-(3-methoxypropyl)benzimidazol-5-yl]oxy-n-(3-methoxypropyl)hexanamide Chemical compound COCCCN1C2=CC(OCCCCCC(=O)NCCCOC)=CC=C2N=C1C1=CC=C(N(C)C)C=C1 UQBWVILSXNUIKE-UHFFFAOYSA-N 0.000 claims 1
- XFVIUATYVUTSGF-UHFFFAOYSA-N 6-[2-phenyl-1-(3-phenylprop-2-enyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound C=1C=CC=CC=1C1=NC2=CC(OCCCCCC(=O)O)=CC=C2N1CC=CC1=CC=CC=C1 XFVIUATYVUTSGF-UHFFFAOYSA-N 0.000 claims 1
- QEIKHUOVEAKQFG-UHFFFAOYSA-N 6-[2-phenyl-3-(3-phenylprop-2-enyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound C=1C=CC=CC=1C=CCN1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 QEIKHUOVEAKQFG-UHFFFAOYSA-N 0.000 claims 1
- SMFVADHEYCEWOY-UHFFFAOYSA-N 6-[3-(2-methoxyethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCOC)C=1C1=CC=CC=C1 SMFVADHEYCEWOY-UHFFFAOYSA-N 0.000 claims 1
- DFDWLURHOGQFSW-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-(3-methyl-1-benzothiophen-2-yl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound S1C2=CC=CC=C2C(C)=C1C1=NC2=CC=C(OCCCCCC(O)=O)C=C2N1CCCOC DFDWLURHOGQFSW-UHFFFAOYSA-N 0.000 claims 1
- INDPJVRGOZYEAY-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-(4-methylphenyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(C)C=C1 INDPJVRGOZYEAY-UHFFFAOYSA-N 0.000 claims 1
- NHYSZAWNZBJCFK-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-(4-nitrophenyl)benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C([N+]([O-])=O)C=C1 NHYSZAWNZBJCFK-UHFFFAOYSA-N 0.000 claims 1
- UGZOMCBFYNICFL-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-[4-(trifluoromethoxy)phenyl]benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(OC(F)(F)F)C=C1 UGZOMCBFYNICFL-UHFFFAOYSA-N 0.000 claims 1
- LOLSGIVBOJQSAF-UHFFFAOYSA-N 6-[3-(3-methoxypropyl)-2-[4-(trifluoromethyl)phenyl]benzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CCCOC)C=1C1=CC=C(C(F)(F)F)C=C1 LOLSGIVBOJQSAF-UHFFFAOYSA-N 0.000 claims 1
- HOPXHXGYTHUNCL-UHFFFAOYSA-N 6-[3-(carboxymethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound OC(=O)CN1C2=CC(OCCCCCC(=O)O)=CC=C2N=C1C1=CC=CC=C1 HOPXHXGYTHUNCL-UHFFFAOYSA-N 0.000 claims 1
- SVXWBZWYXJFCIJ-UHFFFAOYSA-N 6-[3-[2-(dimethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoic acid Chemical compound N=1C2=CC=C(OCCCCCC(O)=O)C=C2N(CC(=O)N(C)C)C=1C1=CC=CC=C1 SVXWBZWYXJFCIJ-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims 1
- JVWQOQXSRSYCFT-UHFFFAOYSA-N methyl 6-(2-phenyl-3-propan-2-ylbenzimidazol-5-yl)oxyhexanoate Chemical compound CC(C)N1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 JVWQOQXSRSYCFT-UHFFFAOYSA-N 0.000 claims 1
- RJRZEGRYMOBHPO-UHFFFAOYSA-N methyl 6-(3-methyl-2-phenylbenzimidazol-5-yl)oxyhexanoate Chemical compound CN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RJRZEGRYMOBHPO-UHFFFAOYSA-N 0.000 claims 1
- FCCVCYZQZGSGCH-UHFFFAOYSA-N methyl 6-[1-(2-ethoxy-2-oxoethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC(OCCCCCC(=O)OC)=CC=C2N(CC(=O)OCC)C=1C1=CC=CC=C1 FCCVCYZQZGSGCH-UHFFFAOYSA-N 0.000 claims 1
- QODFCHJHUGUGCY-UHFFFAOYSA-N methyl 6-[1-[2-(diethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC(OCCCCCC(=O)OC)=CC=C2N(CC(=O)N(CC)CC)C=1C1=CC=CC=C1 QODFCHJHUGUGCY-UHFFFAOYSA-N 0.000 claims 1
- CVIJMGQOPWGJBM-UHFFFAOYSA-N methyl 6-[1-[2-(dimethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC(OCCCCCC(=O)OC)=CC=C2N(CC(=O)N(C)C)C=1C1=CC=CC=C1 CVIJMGQOPWGJBM-UHFFFAOYSA-N 0.000 claims 1
- MQCSPZYKSFVIKO-UHFFFAOYSA-N methyl 6-[1-[3-(4-fluorophenyl)prop-2-enyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1C1=NC2=CC(OCCCCCC(=O)OC)=CC=C2N1CC=CC1=CC=C(F)C=C1 MQCSPZYKSFVIKO-UHFFFAOYSA-N 0.000 claims 1
- MJOQXZCOCAIHCQ-UHFFFAOYSA-N methyl 6-[2-(4-fluorophenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(F)C=C1 MJOQXZCOCAIHCQ-UHFFFAOYSA-N 0.000 claims 1
- ARFNZJCBZZFXAO-UHFFFAOYSA-N methyl 6-[2-(4-hydroxyphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(O)C=C1 ARFNZJCBZZFXAO-UHFFFAOYSA-N 0.000 claims 1
- HCMUGMOZEUSJKN-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(OC)C=C1 HCMUGMOZEUSJKN-UHFFFAOYSA-N 0.000 claims 1
- OMDAFTQNHNPAMM-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-(3-piperidin-1-ylpropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1CCCCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 OMDAFTQNHNPAMM-UHFFFAOYSA-N 0.000 claims 1
- GHUHBUMRBFJICW-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-(3-pyrrolidin-1-ylpropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1CCCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 GHUHBUMRBFJICW-UHFFFAOYSA-N 0.000 claims 1
- YQHQXJXCZDIHSK-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-(4-methylpiperazin-1-yl)propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound C1CN(C)CCN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 YQHQXJXCZDIHSK-UHFFFAOYSA-N 0.000 claims 1
- ZURGVXYAXSCPMY-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-[methyl(2-methylpropanoyl)amino]propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound CC(C)C(=O)N(C)CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 ZURGVXYAXSCPMY-UHFFFAOYSA-N 0.000 claims 1
- BJDNBMQGFNMXSU-UHFFFAOYSA-N methyl 6-[2-(4-methoxyphenyl)-3-[3-[methyl(propanoyl)amino]propyl]benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCN(C)C(=O)CC)C=1C1=CC=C(OC)C=C1 BJDNBMQGFNMXSU-UHFFFAOYSA-N 0.000 claims 1
- XQDFHCKKUULYNQ-UHFFFAOYSA-N methyl 6-[2-(furan-2-yl)-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=CO1 XQDFHCKKUULYNQ-UHFFFAOYSA-N 0.000 claims 1
- CQLOUTFHHRNXGI-UHFFFAOYSA-N methyl 6-[2-[4-(dimethylamino)phenyl]-3-(3-methoxypropyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(N(C)C)C=C1 CQLOUTFHHRNXGI-UHFFFAOYSA-N 0.000 claims 1
- NJYIDPVITDBJLJ-UHFFFAOYSA-N methyl 6-[2-phenyl-1-(3-phenylprop-2-enyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1C1=NC2=CC(OCCCCCC(=O)OC)=CC=C2N1CC=CC1=CC=CC=C1 NJYIDPVITDBJLJ-UHFFFAOYSA-N 0.000 claims 1
- PSPITSJOOQJZSR-UHFFFAOYSA-N methyl 6-[2-phenyl-3-(3-phenylprop-2-enyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C=1C=CC=CC=1C=CCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 PSPITSJOOQJZSR-UHFFFAOYSA-N 0.000 claims 1
- OJTHYUXAUQLVDB-UHFFFAOYSA-N methyl 6-[3-(2-ethoxy-2-oxoethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CC(=O)OCC)C=1C1=CC=CC=C1 OJTHYUXAUQLVDB-UHFFFAOYSA-N 0.000 claims 1
- BXHZSBNJSVRVRJ-UHFFFAOYSA-N methyl 6-[3-(2-methoxyethyl)-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCOC)C=1C1=CC=CC=C1 BXHZSBNJSVRVRJ-UHFFFAOYSA-N 0.000 claims 1
- LQEIKXSUJUKTFP-UHFFFAOYSA-N methyl 6-[3-(3-hydroxypropyl)-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound OCCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 LQEIKXSUJUKTFP-UHFFFAOYSA-N 0.000 claims 1
- ACTSGGUDEBKBPY-UHFFFAOYSA-N methyl 6-[3-(3-imidazol-1-ylpropyl)-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1=CN=CN1CCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 ACTSGGUDEBKBPY-UHFFFAOYSA-N 0.000 claims 1
- VSRYKJXMXRQERW-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-(2-methyl-1-benzothiophen-3-yl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1=CC=C2C(C=3N(C4=CC(OCCCCCC(=O)OC)=CC=C4N=3)CCCOC)=C(C)SC2=C1 VSRYKJXMXRQERW-UHFFFAOYSA-N 0.000 claims 1
- ZHJQDDRKBXGDDT-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-(4-methylphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(C)C=C1 ZHJQDDRKBXGDDT-UHFFFAOYSA-N 0.000 claims 1
- JQNVQURGJLVNEI-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-(4-nitrophenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C([N+]([O-])=O)C=C1 JQNVQURGJLVNEI-UHFFFAOYSA-N 0.000 claims 1
- ALUAUSVSQDWZNC-UHFFFAOYSA-N methyl 6-[3-(3-methoxypropyl)-2-[4-(trifluoromethyl)phenyl]benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCOC)C=1C1=CC=C(C(F)(F)F)C=C1 ALUAUSVSQDWZNC-UHFFFAOYSA-N 0.000 claims 1
- QYCVTWSQNDNKKF-UHFFFAOYSA-N methyl 6-[3-[2-(diethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CC(=O)N(CC)CC)C=1C1=CC=CC=C1 QYCVTWSQNDNKKF-UHFFFAOYSA-N 0.000 claims 1
- RWQOGDKQMUUSNP-UHFFFAOYSA-N methyl 6-[3-[2-(dimethylamino)-2-oxoethyl]-2-phenylbenzimidazol-5-yl]oxyhexanoate Chemical compound CN(C)C(=O)CN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=CC=C1 RWQOGDKQMUUSNP-UHFFFAOYSA-N 0.000 claims 1
- LIESOHRJUOLECF-UHFFFAOYSA-N methyl 6-[3-[3-(2-hydroxyethylamino)propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound OCCNCCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 LIESOHRJUOLECF-UHFFFAOYSA-N 0.000 claims 1
- GCSPSQXDMVTRRZ-UHFFFAOYSA-N methyl 6-[3-[3-(3-imidazol-1-ylpropylamino)propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound C1=CN=CN1CCCNCCCN1C2=CC(OCCCCCC(=O)OC)=CC=C2N=C1C1=CC=C(OC)C=C1 GCSPSQXDMVTRRZ-UHFFFAOYSA-N 0.000 claims 1
- DFJVEVFGJMHNFE-UHFFFAOYSA-N methyl 6-[3-[3-[bis(2-methoxyethyl)amino]propyl]-2-(4-methoxyphenyl)benzimidazol-5-yl]oxyhexanoate Chemical compound N=1C2=CC=C(OCCCCCC(=O)OC)C=C2N(CCCN(CCOC)CCOC)C=1C1=CC=C(OC)C=C1 DFJVEVFGJMHNFE-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
- 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
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Neurosurgery (AREA)
- Diabetes (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10134775A DE10134775A1 (de) | 2001-07-06 | 2001-07-06 | 1-Alkyl-2.aryl-benzimidazolderivate, deren Verwendung zur Herstellung von Arzneimitteln sowie diese Derivate enthaltende pharmazeutische Präparate |
PCT/EP2002/007597 WO2003004023A1 (de) | 2001-07-06 | 2002-07-06 | 1-alkyl-2-aryl-benzimidazolderivate, deren verwendung zur herstellung von arzneimitteln sowie diese derivate enthaltende pharmazeutische präparate |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2004530731A true JP2004530731A (ja) | 2004-10-07 |
JP2004530731A5 JP2004530731A5 (enrdf_load_stackoverflow) | 2009-10-01 |
Family
ID=7692119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003510034A Pending JP2004530731A (ja) | 2001-07-06 | 2002-07-06 | 1−アルキル−2−アリール−ベンズイミダゾール誘導体、医薬製剤の製造のためへのそれらの使用、及びそれらの誘導体を含む医薬製剤 |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1404321A1 (enrdf_load_stackoverflow) |
JP (1) | JP2004530731A (enrdf_load_stackoverflow) |
DE (1) | DE10134775A1 (enrdf_load_stackoverflow) |
WO (1) | WO2003004023A1 (enrdf_load_stackoverflow) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006503817A (ja) * | 2002-08-19 | 2006-02-02 | ローラス セラピューティクス インコーポレーテッド | 2,4,5−三置換イミダゾールおよび抗菌薬としてのこの使用 |
US9309247B2 (en) | 2013-03-20 | 2016-04-12 | Lorus Therapeutics Inc. | 2-substituted imidazo[4,5-D]phenanthroline derivatives and their use in the treatment of cancer |
JP2024056694A (ja) * | 2018-08-06 | 2024-04-23 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | 神経変性疾患を治療するためのPpargc1a活性化剤としての2‐アリールベンゾイミダゾール |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10207843A1 (de) * | 2002-02-15 | 2003-09-04 | Schering Ag | Mikrolia-Inhibitoren zur Unterbrechung von Interleukin 12 und IFN-gamma vermittelten Immunreaktionen |
CA2501539A1 (en) | 2002-10-17 | 2004-04-29 | Amgen Inc. | Benzimidazole derivatives and their use as vanilloid receptor ligands |
AU2004289539C1 (en) | 2003-11-14 | 2012-06-07 | Lorus Therapeutics Inc. | Aryl imidazoles and their use as anti-cancer agents |
DE102004026590A1 (de) * | 2004-06-01 | 2006-01-12 | Siemens Ag | Assistenzsystem für Kraftfahrzeuge |
US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
ES2473597T3 (es) | 2005-05-25 | 2014-07-07 | Lorus Therapeutics Inc. | Derivados de 2-indolil imidazo[4,5-d]fenantrolina y su uso en el tratamiento del cáncer |
US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
WO2010036908A1 (en) * | 2008-09-26 | 2010-04-01 | Eisai R & D Management Co., Ltd. | Use of benzoxazole compounds in the treatment of malaria |
WO2010036905A1 (en) * | 2008-09-26 | 2010-04-01 | Eisai R & D Management Co., Ltd. | Benzoxazole compounds and methods of use |
ES2620177T3 (es) * | 2009-10-15 | 2017-06-27 | Guerbet | Agentes de formación de imágenes y su uso para el diagnóstico in vivo de enfermedades neurodegenerativas, particularmente la enfermedad de Alzheimer y enfermedades derivadas |
WO2015051302A1 (en) | 2013-10-04 | 2015-04-09 | Aptose Biosciences Inc. | Compositions and methods for treating cancers |
WO2017106050A1 (en) * | 2015-12-15 | 2017-06-22 | The Board Of Trustees Of The Leland Stanford Junior University | Method for preventing and/or treating aging-associated cognitive impairment and neuroinflammation |
EP3703685A4 (en) | 2017-10-30 | 2021-07-28 | Aptose Biosciences Inc. | ARYLIMIDAZOLES FOR CANCER TREATMENT |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4330959A1 (de) * | 1993-09-09 | 1995-03-16 | Schering Ag | Neue Benzimidazolderivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
US5552426A (en) * | 1994-04-29 | 1996-09-03 | Eli Lilly And Company | Methods for treating a physiological disorder associated with β-amyloid peptide |
CA2396227C (en) * | 2000-01-14 | 2012-03-20 | Schering Aktiengesellschaft | 1,2-diaryl benzimidazoles for treating illnesses associated with a microglia activation |
-
2001
- 2001-07-06 DE DE10134775A patent/DE10134775A1/de not_active Ceased
-
2002
- 2002-07-06 WO PCT/EP2002/007597 patent/WO2003004023A1/de active Application Filing
- 2002-07-06 EP EP02762333A patent/EP1404321A1/de not_active Withdrawn
- 2002-07-06 JP JP2003510034A patent/JP2004530731A/ja active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006503817A (ja) * | 2002-08-19 | 2006-02-02 | ローラス セラピューティクス インコーポレーテッド | 2,4,5−三置換イミダゾールおよび抗菌薬としてのこの使用 |
JP4854960B2 (ja) * | 2002-08-19 | 2012-01-18 | ローラス セラピューティクス インコーポレーテッド | 2,4,5−三置換イミダゾールおよび抗菌薬としてのこの使用 |
US9309247B2 (en) | 2013-03-20 | 2016-04-12 | Lorus Therapeutics Inc. | 2-substituted imidazo[4,5-D]phenanthroline derivatives and their use in the treatment of cancer |
JP2024056694A (ja) * | 2018-08-06 | 2024-04-23 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | 神経変性疾患を治療するためのPpargc1a活性化剤としての2‐アリールベンゾイミダゾール |
Also Published As
Publication number | Publication date |
---|---|
DE10134775A1 (de) | 2003-01-30 |
WO2003004023A1 (de) | 2003-01-16 |
EP1404321A1 (de) | 2004-04-07 |
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