JP2009530274A5 - - Google Patents
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- JP2009530274A5 JP2009530274A5 JP2009500385A JP2009500385A JP2009530274A5 JP 2009530274 A5 JP2009530274 A5 JP 2009530274A5 JP 2009500385 A JP2009500385 A JP 2009500385A JP 2009500385 A JP2009500385 A JP 2009500385A JP 2009530274 A5 JP2009530274 A5 JP 2009530274A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzimidazol
- benzoyl
- bipyrrolidine
- pyrrolidin
- 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.)
- Withdrawn
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- -1 cycloheteroalkyl Chemical group 0.000 claims 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- ZZCKGXAYSCVENO-UHFFFAOYSA-N 1-[[4-[(4-fluorobenzimidazol-1-yl)methyl]phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC=CC(F)=C2N=C1 ZZCKGXAYSCVENO-UHFFFAOYSA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 claims 2
- GOYZVDIXNJVGAM-NRFANRHFSA-N 5-fluoro-1-[[4-[[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methyl]phenyl]methyl]benzimidazole Chemical compound N1([C@H]2CCN(C2)CC2=CC=C(C=C2)CN2C3=CC=C(C=C3N=C2)F)CCCC1 GOYZVDIXNJVGAM-NRFANRHFSA-N 0.000 claims 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- 102000004384 Histamine H3 receptors Human genes 0.000 claims 2
- 108090000981 Histamine H3 receptors Proteins 0.000 claims 2
- JZSKJBGVSGURIV-FQEVSTJZSA-N [4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=C(C=C3N=C2)F)CCCC1 JZSKJBGVSGURIV-FQEVSTJZSA-N 0.000 claims 2
- HKSPIQPSCHDGLG-NRFANRHFSA-N [4-[(6-chloro-2-methylbenzimidazol-1-yl)methyl]phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC(Cl)=CC=C3N=C2C)CCCC1 HKSPIQPSCHDGLG-NRFANRHFSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 102000005962 receptors Human genes 0.000 claims 2
- 108020003175 receptors Proteins 0.000 claims 2
- NKJNVVMJEBRTDJ-NRFANRHFSA-N (4-benzylphenyl)-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(CC=3C=CC=CC=3)=CC=2)CCCC1 NKJNVVMJEBRTDJ-NRFANRHFSA-N 0.000 claims 1
- XNEFBIXQNVFRLQ-WIIYFNMSSA-N 1-[1-[4-[(3s)-3-pyrrolidin-1-ylpyrrolidine-1-carbonyl]phenyl]ethyl]indole-5-carbonitrile Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)C(C)N2C3=CC=C(C=C3C=C2)C#N)CCCC1 XNEFBIXQNVFRLQ-WIIYFNMSSA-N 0.000 claims 1
- WNYFCVHBWNPGFS-UHFFFAOYSA-N 1-[[2-chloro-4-[(3-piperidin-1-ylpyrrolidin-1-yl)methyl]phenyl]methyl]benzimidazole Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C(Cl)=CC=1CN(C1)CCC1N1CCCCC1 WNYFCVHBWNPGFS-UHFFFAOYSA-N 0.000 claims 1
- OAATWPVYGXYKIX-UHFFFAOYSA-N 1-[[2-chloro-4-[(3-pyrrolidin-1-ylpyrrolidin-1-yl)methyl]phenyl]methyl]benzimidazole Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C(Cl)=CC=1CN(C1)CCC1N1CCCC1 OAATWPVYGXYKIX-UHFFFAOYSA-N 0.000 claims 1
- FSCHBUFEORTTSK-UHFFFAOYSA-N 1-[[4-(benzimidazol-1-ylmethyl)-3-chlorophenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1Cl)=CC=C1CN1C2=CC=CC=C2N=C1 FSCHBUFEORTTSK-UHFFFAOYSA-N 0.000 claims 1
- XIKKJGSHMQMXPV-UHFFFAOYSA-N 1-[[4-(benzimidazol-1-ylmethyl)-3-chlorophenyl]methyl]-n-ethyl-n-methylpyrrolidin-3-amine Chemical compound C1C(N(C)CC)CCN1CC(C=C1Cl)=CC=C1CN1C2=CC=CC=C2N=C1 XIKKJGSHMQMXPV-UHFFFAOYSA-N 0.000 claims 1
- FKYWWSRNAPEWLB-UHFFFAOYSA-N 1-[[4-(indol-1-ylmethyl)phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC=CC=C2C=C1 FKYWWSRNAPEWLB-UHFFFAOYSA-N 0.000 claims 1
- ULCMJQLTPQGROK-UHFFFAOYSA-N 1-[[4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC=C(F)C=C2N=C1 ULCMJQLTPQGROK-UHFFFAOYSA-N 0.000 claims 1
- QWRDXHCEAZUHDY-UHFFFAOYSA-N 1-[[4-[(6-fluorobenzimidazol-1-yl)methyl]phenyl]methyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CC(C=C1)=CC=C1CN1C2=CC(F)=CC=C2N=C1 QWRDXHCEAZUHDY-UHFFFAOYSA-N 0.000 claims 1
- LUEPEBVFWPXDQQ-QFIPXVFZSA-N 1-ethyl-2-[[4-[[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methyl]phenyl]methyl]benzimidazole Chemical compound N1([C@H]2CCN(C2)CC2=CC=C(C=C2)CC=2N(C3=CC=CC=C3N=2)CC)CCCC1 LUEPEBVFWPXDQQ-QFIPXVFZSA-N 0.000 claims 1
- OSZHOKFIDJUEGU-UHFFFAOYSA-N 4-fluoro-1-[[4-[(3-piperidin-1-ylpyrrolidin-1-yl)methyl]phenyl]methyl]benzimidazole Chemical compound C1=NC=2C(F)=CC=CC=2N1CC(C=C1)=CC=C1CN(C1)CCC1N1CCCCC1 OSZHOKFIDJUEGU-UHFFFAOYSA-N 0.000 claims 1
- ITAJFFQEBAKMJR-ZZWBGTBQSA-N 5-fluoro-1-[[4-[[3-[(2r)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methyl]phenyl]methyl]benzimidazole Chemical compound C[C@@H]1CCCN1C1CN(CC=2C=CC(CN3C4=CC=C(F)C=C4N=C3)=CC=2)CC1 ITAJFFQEBAKMJR-ZZWBGTBQSA-N 0.000 claims 1
- GZGMNXQGFBEWFA-NRFANRHFSA-N 6-fluoro-1-[[4-[[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methyl]phenyl]methyl]benzimidazole Chemical compound N1([C@H]2CCN(C2)CC2=CC=C(C=C2)CN2C=NC3=CC=C(C=C32)F)CCCC1 GZGMNXQGFBEWFA-NRFANRHFSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- XPFYAAVBFKWWSE-UHFFFAOYSA-N CC1N(CCCC1)C1CN(CC1)C(=O)C1=CC=C(CN2C=NC3=C2C=CC=C3)C=C1 Chemical compound CC1N(CCCC1)C1CN(CC1)C(=O)C1=CC=C(CN2C=NC3=C2C=CC=C3)C=C1 XPFYAAVBFKWWSE-UHFFFAOYSA-N 0.000 claims 1
- 208000012239 Developmental disease Diseases 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- BZWDTZMVRVTPQF-NRFANRHFSA-N [(3s)-3-(azepan-1-yl)pyrrolidin-1-yl]-[4-[(7-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C=NC=3C=CC=C(C2=3)F)CCCCCC1 BZWDTZMVRVTPQF-NRFANRHFSA-N 0.000 claims 1
- YFOVYMUNACKLJM-SFHVURJKSA-N [(3s)-3-(azetidin-1-yl)pyrrolidin-1-yl]-[4-[(7-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C=NC=3C=CC=C(C2=3)F)CCC1 YFOVYMUNACKLJM-SFHVURJKSA-N 0.000 claims 1
- ZKAJTXVFCUQAHA-FQEVSTJZSA-N [(3s)-3-(dimethylamino)pyrrolidin-1-yl]-[4-[(1-methylindol-3-yl)methyl]phenyl]methanone Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C(C=C1)=CC=C1CC1=CN(C)C2=CC=CC=C12 ZKAJTXVFCUQAHA-FQEVSTJZSA-N 0.000 claims 1
- AGGGVCYHWZMNEH-SFHVURJKSA-N [(3s)-3-[ethyl(methyl)amino]pyrrolidin-1-yl]-[4-[(7-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1[C@@H](N(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1C2=C(F)C=CC=C2N=C1 AGGGVCYHWZMNEH-SFHVURJKSA-N 0.000 claims 1
- CUHVFDRJOCNUTK-ACJLOTCBSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(1r)-1-(5-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]methanone Chemical compound C1=CC([C@@H](C)N2C3=CC=C(Cl)C=C3N=C2C)=CC=C1C(=O)N1CC[C@H](N)C1 CUHVFDRJOCNUTK-ACJLOTCBSA-N 0.000 claims 1
- STRDTYMZVGDYCN-ACJLOTCBSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(1r)-1-(6-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]methanone Chemical compound C1=CC([C@@H](C)N2C3=CC(Cl)=CC=C3N=C2C)=CC=C1C(=O)N1CC[C@H](N)C1 STRDTYMZVGDYCN-ACJLOTCBSA-N 0.000 claims 1
- CUHVFDRJOCNUTK-UGSOOPFHSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(1s)-1-(5-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]methanone Chemical compound C1=CC([C@H](C)N2C3=CC=C(Cl)C=C3N=C2C)=CC=C1C(=O)N1CC[C@H](N)C1 CUHVFDRJOCNUTK-UGSOOPFHSA-N 0.000 claims 1
- STRDTYMZVGDYCN-UGSOOPFHSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(1s)-1-(6-chloro-2-methylbenzimidazol-1-yl)ethyl]phenyl]methanone Chemical compound C1=CC([C@H](C)N2C3=CC(Cl)=CC=C3N=C2C)=CC=C1C(=O)N1CC[C@H](N)C1 STRDTYMZVGDYCN-UGSOOPFHSA-N 0.000 claims 1
- OYJUQBUJIKMYLC-INIZCTEOSA-N [(3s)-3-aminopyrrolidin-1-yl]-[4-[(5-chlorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1[C@@H](N)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=C(Cl)C=C2N=C1 OYJUQBUJIKMYLC-INIZCTEOSA-N 0.000 claims 1
- MXFTYPZMFCWDGD-IBGZPJMESA-N [(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]-[4-[[2-(trifluoromethyl)benzimidazol-1-yl]methyl]phenyl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C2=CC=C(C=C2)CN2C3=CC=CC=C3N=C2C(F)(F)F)CCCC1 MXFTYPZMFCWDGD-IBGZPJMESA-N 0.000 claims 1
- IJIVJXMGORRXAU-UHFFFAOYSA-N [3-(2-benzylpyrrolidin-1-yl)pyrrolidin-1-yl]-[4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCCC1CC1=CC=CC=C1 IJIVJXMGORRXAU-UHFFFAOYSA-N 0.000 claims 1
- LPTXIOWQQHYDOK-UHFFFAOYSA-N [3-(azepan-1-yl)pyrrolidin-1-yl]-[4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCCCCC1 LPTXIOWQQHYDOK-UHFFFAOYSA-N 0.000 claims 1
- JQMJISOLRBAIJJ-UHFFFAOYSA-N [3-(azetidin-1-yl)pyrrolidin-1-yl]-[4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1)=CC=C1C(=O)N(C1)CCC1N1CCC1 JQMJISOLRBAIJJ-UHFFFAOYSA-N 0.000 claims 1
- YHKWENOEKQIQIK-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(indol-1-ylmethyl)phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=CC=C2C=C1 YHKWENOEKQIQIK-UHFFFAOYSA-N 0.000 claims 1
- UYKJSYAQDGARFD-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(2-phenylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=CC=C2N=C1C1=CC=CC=C1 UYKJSYAQDGARFD-UHFFFAOYSA-N 0.000 claims 1
- KMGRYCOPEWXFGC-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(4-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=CC(F)=C2N=C1 KMGRYCOPEWXFGC-UHFFFAOYSA-N 0.000 claims 1
- LKKTYXFSXVJHDQ-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(5-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=C(F)C=C2N=C1 LKKTYXFSXVJHDQ-UHFFFAOYSA-N 0.000 claims 1
- VUKGGORJGGCJMA-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=C(C)C=C2N=C1 VUKGGORJGGCJMA-UHFFFAOYSA-N 0.000 claims 1
- VGKWMGNAFBTILL-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(6-fluorobenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC(F)=CC=C2N=C1 VGKWMGNAFBTILL-UHFFFAOYSA-N 0.000 claims 1
- MTWVKIPKXDPFST-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-[(6-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC(C)=CC=C2N=C1 MTWVKIPKXDPFST-UHFFFAOYSA-N 0.000 claims 1
- HCQNTGCTJYYFSN-UHFFFAOYSA-N [3-[ethyl(methyl)amino]pyrrolidin-1-yl]-[4-[(5-methylbenzimidazol-1-yl)methyl]phenyl]methanone Chemical compound C1C(N(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1C2=CC=C(C)C=C2N=C1 HCQNTGCTJYYFSN-UHFFFAOYSA-N 0.000 claims 1
- CHXYRVONIWLABP-UHFFFAOYSA-N [4-(1h-benzimidazol-2-ylmethyl)phenyl]-(3-piperidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C=1C=C(CC=2NC3=CC=CC=C3N=2)C=CC=1C(=O)N(C1)CCC1N1CCCCC1 CHXYRVONIWLABP-UHFFFAOYSA-N 0.000 claims 1
- HCASEGGSGZPNRG-UHFFFAOYSA-N [4-(1h-benzimidazol-2-ylmethyl)phenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound C=1C=C(CC=2NC3=CC=CC=C3N=2)C=CC=1C(=O)N(C1)CCC1N1CCCC1 HCASEGGSGZPNRG-UHFFFAOYSA-N 0.000 claims 1
- RHHNYZPUWAFSQK-NRFANRHFSA-N [4-(1h-indol-3-ylmethyl)phenyl]-[(3s)-3-pyrrolidin-1-ylpyrrolidin-1-yl]methanone Chemical compound N1([C@H]2CCN(C2)C(=O)C=2C=CC(CC=3C4=CC=CC=C4NC=3)=CC=2)CCCC1 RHHNYZPUWAFSQK-NRFANRHFSA-N 0.000 claims 1
- MKFUTLJBZBYCCA-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)-2-fluorophenyl]-(3-pyrrolidin-1-ylpyrrolidin-1-yl)methanone Chemical compound FC1=CC(CN2C3=CC=CC=C3N=C2)=CC=C1C(=O)N(C1)CCC1N1CCCC1 MKFUTLJBZBYCCA-UHFFFAOYSA-N 0.000 claims 1
- LABNTHHPJNEGQR-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)-2-methoxyphenyl]-[3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound COC1=CC(CN2C3=CC=CC=C3N=C2)=CC=C1C(=O)N1CCC(N(C)C)C1 LABNTHHPJNEGQR-UHFFFAOYSA-N 0.000 claims 1
- FLFNHBOROKVAFC-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-(3-piperidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C=CC=1C(=O)N(C1)CCCC1N1CCCCC1 FLFNHBOROKVAFC-UHFFFAOYSA-N 0.000 claims 1
- WSVDCIDSNHAANT-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-(3-pyrrolidin-1-ylpiperidin-1-yl)methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3N=C2)C=CC=1C(=O)N(C1)CCCC1N1CCCC1 WSVDCIDSNHAANT-UHFFFAOYSA-N 0.000 claims 1
- WMGFFKHQNCLGHB-WIYYLYMNSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[(3r)-3-[(2r)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@@H]1CCCN1[C@H]1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CC1 WMGFFKHQNCLGHB-WIYYLYMNSA-N 0.000 claims 1
- WMGFFKHQNCLGHB-GHTZIAJQSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[(3r)-3-[(2s)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]methanone Chemical compound C[C@H]1CCCN1[C@H]1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CC1 WMGFFKHQNCLGHB-GHTZIAJQSA-N 0.000 claims 1
- RBFNAMZWICIZDO-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[3-(2-methylpyrrolidin-1-yl)piperidin-1-yl]methanone Chemical compound CC1CCCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CCC1 RBFNAMZWICIZDO-UHFFFAOYSA-N 0.000 claims 1
- YOPCFDOLUZCVKR-UHFFFAOYSA-N [4-(benzimidazol-1-ylmethyl)phenyl]-[3-(4-methylpiperidin-1-yl)pyrrolidin-1-yl]methanone Chemical compound C1CC(C)CCN1C1CN(C(=O)C=2C=CC(CN3C4=CC=CC=C4N=C3)=CC=2)CC1 YOPCFDOLUZCVKR-UHFFFAOYSA-N 0.000 claims 1
- CCUDNLWFJUWTMY-AIBWNMTMSA-N [4-(indazol-1-ylmethyl)phenyl]-[1-[(3s)-pyrrolidin-3-yl]pyrrolidin-2-yl]methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3C=N2)C=CC=1C(=O)C1CCCN1[C@H]1CCNC1 CCUDNLWFJUWTMY-AIBWNMTMSA-N 0.000 claims 1
- DZNOGNRCWAFGJA-BBQAJUCSSA-N [4-(indol-1-ylmethyl)phenyl]-[1-[(3s)-pyrrolidin-3-yl]pyrrolidin-2-yl]methanone Chemical compound C=1C=C(CN2C3=CC=CC=C3C=C2)C=CC=1C(=O)C1CCCN1[C@H]1CCNC1 DZNOGNRCWAFGJA-BBQAJUCSSA-N 0.000 claims 1
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| JP2009500385A Withdrawn JP2009530274A (ja) | 2006-03-15 | 2007-03-08 | ヒスタミン−３アンタゴニストとしてのｎ−置換−アザシクリルアミン化合物 |
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| Country | Link |
|---|---|
| US (1) | US7820825B2 (OSRAM) |
| EP (1) | EP1994022A2 (OSRAM) |
| JP (1) | JP2009530274A (OSRAM) |
| AR (1) | AR059905A1 (OSRAM) |
| AU (1) | AU2007227681A1 (OSRAM) |
| BR (1) | BRPI0709612A2 (OSRAM) |
| CA (1) | CA2645731A1 (OSRAM) |
| MX (1) | MX2008011791A (OSRAM) |
| PE (1) | PE20071023A1 (OSRAM) |
| TW (1) | TW200800958A (OSRAM) |
| WO (1) | WO2007108936A2 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1972914A (zh) * | 2004-03-31 | 2007-05-30 | 詹森药业有限公司 | 作为组胺h3受体配合体的非咪唑杂环化合物 |
| AU2007227681A1 (en) | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| JP2009537542A (ja) | 2006-05-19 | 2009-10-29 | ワイス | ヒスタミン−３アンタゴニストとしてのｎ−ベンゾイルピロリジン−３−イルアミンおよびｎ−ベンジルピロリジン−３−イルアミン |
| EA015555B1 (ru) | 2006-05-30 | 2011-08-30 | Янссен Фармацевтика Н.В. | Замещенные пиридиламидные соединения в качестве модуляторов гистаминового h-рецептора |
| EP2038269A1 (en) * | 2006-06-29 | 2009-03-25 | Janssen Pharmaceutica N.V. | Substituted benzamide modulators of the histamine h3 receptor |
| PE20081152A1 (es) | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| EP2155719A1 (en) * | 2007-05-24 | 2010-02-24 | Wyeth LLC | Azacyclylbenzamide derivatives as histamine-3 antagonists |
| CL2008002088A1 (es) | 2007-07-16 | 2008-09-05 | Wyeth Corp | Compuestos derivados de fenilo sustituido, moduladores del receptor de histamina 3; proceso de preparacion; composicion farmaceutica; y uso en el tratamiento de trastornos cognitivos tales como demencia, alzheimer, entre otros. |
| US8883776B2 (en) * | 2007-11-20 | 2014-11-11 | Janssen Pharmaceutica N.V. | Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine H3 receptor |
| US20090131417A1 (en) * | 2007-11-20 | 2009-05-21 | Letavic Michael A | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
| PL2445899T3 (pl) * | 2009-06-26 | 2017-08-31 | Sanofi | Nowe sole fumaranowe antagonisty receptora histaminy H3 |
| WO2012102254A1 (ja) | 2011-01-25 | 2012-08-02 | キッセイ薬品工業株式会社 | インドール誘導体、またはその薬理学的に許容される塩 |
| ES2657912T3 (es) * | 2012-07-17 | 2018-03-07 | Glaxosmithkline Intellectual Property (No. 2) Limited | Indolcarbonitrilos como moduladores selectivos de los receptores de andrógenos |
| HRP20200064T1 (hr) | 2015-06-09 | 2020-04-03 | Abbvie Inc. | Modulatori nuklearnih receptora (ror) namijenjeni liječenju upalnih i autoimunih bolesti |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
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| US3933829A (en) | 1974-08-22 | 1976-01-20 | John Wyeth & Brother Limited | 4-Aminoquinoline derivatives |
| US4166853A (en) | 1978-05-05 | 1979-09-04 | The Upjohn Company | Antihypertensive 7-trifluoromethyl-4-aminoquinolones |
| US4159331A (en) | 1978-05-05 | 1979-06-26 | The Upjohn Company | Antihypertensive 4-aminoquinolines |
| EP0525129A4 (en) | 1990-04-13 | 1993-03-24 | Smith-Kline Beecham Corporation | Substituted benzimidazoles |
| CA2136999C (en) | 1993-04-07 | 2004-05-11 | Takafumi Fujioka | Peripheral vasodilating agent containing piperidine derivative as active ingredient |
| IL117149A0 (en) | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US6034093A (en) * | 1995-06-07 | 2000-03-07 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid N-[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds |
| AU7270798A (en) | 1997-05-01 | 1998-11-24 | Eli Lilly And Company | Antithrombotic agents |
| US6699873B1 (en) * | 1999-08-04 | 2004-03-02 | Millennium Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
| US7375125B2 (en) * | 1999-08-04 | 2008-05-20 | Ore Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
| WO2001042224A1 (en) | 1999-12-09 | 2001-06-14 | Mitsubishi Pharma Corporation | Carboxyamido derivatives |
| AU2001247906A1 (en) | 2000-03-31 | 2001-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Phenyl-substituted indoles and indazoles |
| US20070004713A1 (en) | 2000-12-07 | 2007-01-04 | Bernard Barlaam | Therapeutic benimidazole compounds |
| HN2002000156A (es) | 2001-07-06 | 2003-11-27 | Inc Agouron Pharmaceuticals | Derivados de benzamida tiazol y composiciones farmaceuticas para inhibir la proliferacion de celulas y metodos para su utilización. |
| ATE447404T1 (de) | 2002-03-29 | 2009-11-15 | Novartis Vaccines & Diagnostic | Substituierte benzazole und ihre verwendung als raf-kinase-hemmer |
| ATE489388T1 (de) | 2003-03-14 | 2010-12-15 | Medigene Ltd | Immunmodulierende heterocyclische verbindungen |
| ATE454372T1 (de) * | 2004-04-01 | 2010-01-15 | Lilly Co Eli | Am histamin-h3-rezeptor wirksame mittel, herstellung und therapeutische anwendungen |
| JP4467616B2 (ja) | 2004-05-14 | 2010-05-26 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | Ａｕｒｏｒａキナーゼの阻害により有糸分裂の進行を阻止するための化合物および方法 |
| TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
| US20060014733A1 (en) | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
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| JP4942654B2 (ja) | 2004-08-23 | 2012-05-30 | イーライ リリー アンド カンパニー | ヒスタミンｈ３受容体薬剤、製剤及び治療的使用 |
| US20080015202A1 (en) * | 2004-09-09 | 2008-01-17 | Astellas Pharma Inc. | Thiazole Derivatives Having Vap-1 Inhibitory Activity |
| UY29149A1 (es) | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| US7381732B2 (en) | 2004-10-26 | 2008-06-03 | Bristol-Myers Squibb Company | Pyrazolobenzamides and derivatives as factor Xa inhibitors |
| MX2007008843A (es) | 2005-01-21 | 2007-08-22 | Schering Corp | Derivados de imidazol y bencimidazol utiles como antagonistas de histamina h3. |
| WO2006113140A2 (en) | 2005-04-15 | 2006-10-26 | Elan Pharmaceuticals, Inc. | Novel compounds useful for bradykinin b1 receptor antagonism |
| AU2007227681A1 (en) | 2006-03-15 | 2007-09-27 | Wyeth | N-substituted-azacyclylamines as histamine-3 antagonists |
| CA2646585A1 (en) | 2006-03-20 | 2007-09-27 | Glaxo Group Limited | Compounds which potentiate ampa receptor and uses thereof in medicine |
| US20070238718A1 (en) | 2006-04-06 | 2007-10-11 | Matthias Grauert | Thiazolyl-dihydro-indazole |
| JP2009537542A (ja) * | 2006-05-19 | 2009-10-29 | ワイス | ヒスタミン−３アンタゴニストとしてのｎ−ベンゾイルピロリジン−３−イルアミンおよびｎ−ベンジルピロリジン−３−イルアミン |
| PE20081152A1 (es) | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
-
2007
- 2007-03-08 AU AU2007227681A patent/AU2007227681A1/en not_active Abandoned
- 2007-03-08 EP EP07752471A patent/EP1994022A2/en not_active Withdrawn
- 2007-03-08 JP JP2009500385A patent/JP2009530274A/ja not_active Withdrawn
- 2007-03-08 BR BRPI0709612-7A patent/BRPI0709612A2/pt not_active Application Discontinuation
- 2007-03-08 CA CA002645731A patent/CA2645731A1/en not_active Abandoned
- 2007-03-08 MX MX2008011791A patent/MX2008011791A/es unknown
- 2007-03-08 WO PCT/US2007/005776 patent/WO2007108936A2/en not_active Ceased
- 2007-03-13 PE PE2007000268A patent/PE20071023A1/es not_active Application Discontinuation
- 2007-03-13 TW TW096108558A patent/TW200800958A/zh unknown
- 2007-03-14 US US11/724,078 patent/US7820825B2/en not_active Expired - Fee Related
- 2007-03-15 AR ARP070101063A patent/AR059905A1/es unknown
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