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- Withdrawn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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| US (1) | US7820825B2 (https=) |
| EP (1) | EP1994022A2 (https=) |
| JP (1) | JP2009530274A (https=) |
| AR (1) | AR059905A1 (https=) |
| AU (1) | AU2007227681A1 (https=) |
| BR (1) | BRPI0709612A2 (https=) |
| CA (1) | CA2645731A1 (https=) |
| MX (1) | MX2008011791A (https=) |
| PE (1) | PE20071023A1 (https=) |
| TW (1) | TW200800958A (https=) |
| WO (1) | WO2007108936A2 (https=) |
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| AU2005230902A1 (en) * | 2004-03-31 | 2005-10-20 | Janssen Pharmaceutica, N.V. | Non-imidazole heterocyclic compounds as histamine H3-receptor ligands |
| BRPI0709612A2 (pt) | 2006-03-15 | 2011-07-19 | Wyeth Corp | composto de fórmula i; método para o tratamento de um distúrbio no sistema nervoso central relacionado ou afetado pelo receptor histamina-3 em um paciente que necessita deste tratamento; método para a inibição do receptor h3; composição farmacêutica; e processo para a preparação de um composto de fórmula i |
| EP2027086B1 (en) | 2006-05-19 | 2011-11-16 | Wyeth LLC | N-benzoyl-pyrrolidin-3-ylamines as histamine-3 antagonists |
| EA015555B1 (ru) * | 2006-05-30 | 2011-08-30 | Янссен Фармацевтика Н.В. | Замещенные пиридиламидные соединения в качестве модуляторов гистаминового h-рецептора |
| JP2009542706A (ja) * | 2006-06-29 | 2009-12-03 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ヒスタミンｈ３受容体の置換ベンズアミドモジュレーター |
| 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 |
| TW200901983A (en) * | 2007-05-24 | 2009-01-16 | Wyeth Corp | Azacyclylbenzamide derivatives as histamine-3 antagonists |
| CA2693138A1 (en) | 2007-07-16 | 2009-01-22 | Wyeth Llc | Aminoalkylazole derivatives as histamine-3 antagonists |
| EP2220045A1 (en) * | 2007-11-20 | 2010-08-25 | Janssen Pharmaceutica, N.V. | Substituted pyridyl amide compounds as modulators of the histamine h3 receptor |
| EA018582B1 (ru) | 2007-11-20 | 2013-09-30 | Янссен Фармацевтика Н.В. | Соединения циклоалкилокси- и гетероциклоалкилоксипиридина как модуляторы гистаминового рецептора н |
| AU2010264422B2 (en) * | 2009-06-26 | 2014-12-18 | Sanofi | Novel fumarate salts of a histamine H3 receptor antagonist |
| 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 |
| KR102127939B1 (ko) | 2012-07-17 | 2020-06-29 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴 |
| DK3307734T3 (da) | 2015-06-09 | 2020-01-27 | Abbvie Inc | Nukleære receptormodulatorer (ror) til behandling af inflammatoriske og autoimmune sygdomme |
| WO2020113094A1 (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 |
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| US6699873B1 (en) * | 1999-08-04 | 2004-03-02 | Millennium Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
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| NZ535985A (en) | 2002-03-29 | 2007-04-27 | Chiron Corp | Substituted benzazoles and use thereof as RAF kinase inhibitors |
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| SI1735278T1 (sl) * | 2004-04-01 | 2010-05-31 | Lilly Co Eli | Agenti histamin h receptorja priprava in terapevtska uporaba |
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| US20060014733A1 (en) * | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
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| ES2534605T3 (es) | 2004-08-23 | 2015-04-24 | Eli Lilly And Company | Agentes receptores de la histamina H3, preparación y usos terapéuticos |
| CA2579889A1 (en) * | 2004-09-09 | 2006-03-16 | 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 |
| CN101107231A (zh) | 2005-01-21 | 2008-01-16 | 先灵公司 | 用作组胺h3拮抗剂的咪唑和苯并咪唑衍生物 |
| US20070032475A1 (en) | 2005-04-15 | 2007-02-08 | Ye Xiaocong M | Novel compounds useful for bradykinin B1 receptor antagonism |
| BRPI0709612A2 (pt) | 2006-03-15 | 2011-07-19 | Wyeth Corp | composto de fórmula i; método para o tratamento de um distúrbio no sistema nervoso central relacionado ou afetado pelo receptor histamina-3 em um paciente que necessita deste tratamento; método para a inibição do receptor h3; composição farmacêutica; e processo para a preparação de um composto de fórmula i |
| 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 |
| EP2027086B1 (en) * | 2006-05-19 | 2011-11-16 | Wyeth LLC | N-benzoyl-pyrrolidin-3-ylamines as histamine-3 antagonists |
| PE20081152A1 (es) * | 2006-10-06 | 2008-08-10 | Wyeth Corp | Azaciclilaminas n-sustituidas como antagonistas de histamina-3 |
-
2007
- 2007-03-08 BR BRPI0709612-7A patent/BRPI0709612A2/pt not_active Application Discontinuation
- 2007-03-08 EP EP07752471A patent/EP1994022A2/en not_active Withdrawn
- 2007-03-08 WO PCT/US2007/005776 patent/WO2007108936A2/en not_active Ceased
- 2007-03-08 MX MX2008011791A patent/MX2008011791A/es unknown
- 2007-03-08 CA CA002645731A patent/CA2645731A1/en not_active Abandoned
- 2007-03-08 AU AU2007227681A patent/AU2007227681A1/en not_active Abandoned
- 2007-03-08 JP JP2009500385A patent/JP2009530274A/ja not_active Withdrawn
- 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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