ME01143B - BENZOIMIDAZOL-2-IL PIRIMIDINI l PIRAZINI KAO MODULATORI HISTAMINSKOG H4 RECEPTORA - Google Patents
BENZOIMIDAZOL-2-IL PIRIMIDINI l PIRAZINI KAO MODULATORI HISTAMINSKOG H4 RECEPTORAInfo
- Publication number
- ME01143B ME01143B MEP-2010-163A MEP16310A ME01143B ME 01143 B ME01143 B ME 01143B ME P16310 A MEP16310 A ME P16310A ME 01143 B ME01143 B ME 01143B
- Authority
- ME
- Montenegro
- Prior art keywords
- methyl
- propyl
- piperidin
- benzoimidazol
- pyrimidin
- Prior art date
Links
- 102000004187 Histamine H4 receptors Human genes 0.000 title claims 5
- 108090000796 Histamine H4 receptors Proteins 0.000 title claims 5
- WTZRQYJHRXQWTK-UHFFFAOYSA-N 2-pyrimidin-2-yl-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1C1=NC=CC=N1 WTZRQYJHRXQWTK-UHFFFAOYSA-N 0.000 title 1
- 150000003216 pyrazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 229910003827 NRaRb Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 208000035475 disorder Diseases 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 238000000034 method Methods 0.000 claims 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- PJJRYWYAYDVXPC-UHFFFAOYSA-N 4-methyl-5-(4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C=CC=C2N1 PJJRYWYAYDVXPC-UHFFFAOYSA-N 0.000 claims 5
- IQBLAMGGXYNKQV-UHFFFAOYSA-N 5-(1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrazin-2-amine Chemical compound C1CN(C)CCC1CCCNC1=CN=C(C=2NC3=CC=CC=C3N=2)C=N1 IQBLAMGGXYNKQV-UHFFFAOYSA-N 0.000 claims 5
- BRLHVAAQJMFKHY-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-4-ethyl-n-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(C)C(C)=C3N=2)C(CC)=NC=1N(C)CCCC1CCN(C)CC1 BRLHVAAQJMFKHY-UHFFFAOYSA-N 0.000 claims 5
- JURUDPPXJKLNNP-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 JURUDPPXJKLNNP-UHFFFAOYSA-N 0.000 claims 5
- YATKPGCYPNPZGF-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(C)C(C)=C3N=2)C(CCC)=NC=1NCCCC1CCN(C)CC1 YATKPGCYPNPZGF-UHFFFAOYSA-N 0.000 claims 5
- ISKPNXCCSMGZJG-UHFFFAOYSA-N 5-(4,6-difluoro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(F)C=C(F)C=C2N1 ISKPNXCCSMGZJG-UHFFFAOYSA-N 0.000 claims 5
- JTFUKAHIHKKIRU-UHFFFAOYSA-N 5-(4-fluoro-5-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(C)C(F)=C3N=2)C(CCC)=NC=1NCCCC1CCN(C)CC1 JTFUKAHIHKKIRU-UHFFFAOYSA-N 0.000 claims 5
- WWWFRWPAACAUEZ-UHFFFAOYSA-N 5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 WWWFRWPAACAUEZ-UHFFFAOYSA-N 0.000 claims 5
- LGLQDKGMEQZHCV-UHFFFAOYSA-N 5-(6-fluoro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(F)=CC=C2N1 LGLQDKGMEQZHCV-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- OZTXWSMMFSAFEI-UHFFFAOYSA-N 4-cyclobutyl-5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CCC2)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 OZTXWSMMFSAFEI-UHFFFAOYSA-N 0.000 claims 4
- JPIDROZUGRRXLB-UHFFFAOYSA-N 4-cyclobutyl-5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CCC2)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 JPIDROZUGRRXLB-UHFFFAOYSA-N 0.000 claims 4
- LQWNVGIMAZERKF-UHFFFAOYSA-N 4-cyclopropyl-5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 LQWNVGIMAZERKF-UHFFFAOYSA-N 0.000 claims 4
- CZSUPJXGIODQBS-UHFFFAOYSA-N 4-cyclopropyl-5-(4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C=CC=C2N1 CZSUPJXGIODQBS-UHFFFAOYSA-N 0.000 claims 4
- LAYDCJYPQQPMOM-UHFFFAOYSA-N 4-ethyl-5-(4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(CC)=NC=1NCCCC1CCN(C)CC1 LAYDCJYPQQPMOM-UHFFFAOYSA-N 0.000 claims 4
- ZPJUBYMZMHXTGP-UHFFFAOYSA-N 4-ethyl-5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CC)=NC=1NCCCC1CCN(C)CC1 ZPJUBYMZMHXTGP-UHFFFAOYSA-N 0.000 claims 4
- CFHHGHPRFXZSKO-UHFFFAOYSA-N 4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]-5-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(C(F)(F)F)=CC=C2N1 CFHHGHPRFXZSKO-UHFFFAOYSA-N 0.000 claims 4
- ARAIBGJAUSWRDP-UHFFFAOYSA-N 5-(1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC=CC=C2N1 ARAIBGJAUSWRDP-UHFFFAOYSA-N 0.000 claims 4
- SIYUECLFUKKWTD-UHFFFAOYSA-N 5-(4,5-difluoro-1h-benzimidazol-2-yl)-4-ethyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(F)C(F)=C3N=2)C(CC)=NC=1NCCCC1CCN(C)CC1 SIYUECLFUKKWTD-UHFFFAOYSA-N 0.000 claims 4
- FGPDYHWYLFFVRS-UHFFFAOYSA-N 5-(4,5-difluoro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(F)C(F)=CC=C2N1 FGPDYHWYLFFVRS-UHFFFAOYSA-N 0.000 claims 4
- LSOJSTAHVGFZJI-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 LSOJSTAHVGFZJI-UHFFFAOYSA-N 0.000 claims 4
- PHBVEYWDUUAXCQ-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrazin-2-amine Chemical compound C1CN(C)CCC1CCCNC1=CN=C(C=2NC3=CC=C(C)C(C)=C3N=2)C=N1 PHBVEYWDUUAXCQ-UHFFFAOYSA-N 0.000 claims 4
- NDDDKWKUDSCDHZ-UHFFFAOYSA-N 5-(4,6-dimethyl-1h-benzimidazol-2-yl)-n,4-dimethyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC(C)=CC(C)=C3N=2)C(C)=NC=1N(C)CCCC1CCN(C)CC1 NDDDKWKUDSCDHZ-UHFFFAOYSA-N 0.000 claims 4
- PDBBSWKMAJWONV-UHFFFAOYSA-N 5-(5,6-difluoro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=CC(F)=C(F)C=C2N1 PDBBSWKMAJWONV-UHFFFAOYSA-N 0.000 claims 4
- OMZOBZRBRDTSFA-UHFFFAOYSA-N 5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC1=NC=C(C=2NC3=CC=C(F)C(C)=C3N=2)C=N1 OMZOBZRBRDTSFA-UHFFFAOYSA-N 0.000 claims 4
- KYERXDDXJNCIFV-UHFFFAOYSA-N 5-(6-fluoro-4-methyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C=C(F)C=C2N1 KYERXDDXJNCIFV-UHFFFAOYSA-N 0.000 claims 4
- XIWNFTRGYWFCRW-UHFFFAOYSA-N 5-(6-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(C)C=C(F)C=C2N1 XIWNFTRGYWFCRW-UHFFFAOYSA-N 0.000 claims 4
- 101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 claims 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- YCGCJDYROXPNHW-UHFFFAOYSA-N 4-cyclobutyl-5-(4,6-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CCC2)=NC=C1C1=NC2=C(C)C=C(C)C=C2N1 YCGCJDYROXPNHW-UHFFFAOYSA-N 0.000 claims 3
- FJWXBBXPJRGQNY-UHFFFAOYSA-N 4-cyclopropyl-5-(4,6-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C=C(C)C=C2N1 FJWXBBXPJRGQNY-UHFFFAOYSA-N 0.000 claims 3
- AXHZAMUWSMFUAB-UHFFFAOYSA-N 4-cyclopropyl-5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 AXHZAMUWSMFUAB-UHFFFAOYSA-N 0.000 claims 3
- LWUKRCUSHNAFNR-UHFFFAOYSA-N 4-cyclopropyl-5-(6-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C=C(F)C=C2N1 LWUKRCUSHNAFNR-UHFFFAOYSA-N 0.000 claims 3
- QIHYSXIESUUFQG-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propan-2-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(C)C(C)=C3N=2)C(C(C)C)=NC=1NCCCC1CCN(C)CC1 QIHYSXIESUUFQG-UHFFFAOYSA-N 0.000 claims 3
- WCXNIZNFUUQYKG-UHFFFAOYSA-N 5-(4,6-dimethyl-1h-benzimidazol-2-yl)-4-ethyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC(C)=CC(C)=C3N=2)C(CC)=NC=1NCCCC1CCN(C)CC1 WCXNIZNFUUQYKG-UHFFFAOYSA-N 0.000 claims 3
- WNGRFKJIQUHAGU-UHFFFAOYSA-N 5-(4,6-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propan-2-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC(C)=CC(C)=C3N=2)C(C(C)C)=NC=1NCCCC1CCN(C)CC1 WNGRFKJIQUHAGU-UHFFFAOYSA-N 0.000 claims 3
- UQRGFHZYHLXDNC-UHFFFAOYSA-N 5-(4-chloro-6-methyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(Cl)C=C(C)C=C2N1 UQRGFHZYHLXDNC-UHFFFAOYSA-N 0.000 claims 3
- LAXSIUKHUBYMHV-UHFFFAOYSA-N 5-(5,6-dichloro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(Cl)=C(Cl)C=C2N1 LAXSIUKHUBYMHV-UHFFFAOYSA-N 0.000 claims 3
- KFCWPNNLWGGGRO-UHFFFAOYSA-N 5-(5-chloro-4-methyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C(Cl)=CC=C2N1 KFCWPNNLWGGGRO-UHFFFAOYSA-N 0.000 claims 3
- HGFVXRFLCSVTRB-UHFFFAOYSA-N 5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propan-2-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(C(C)C)=NC=1NCCCC1CCN(C)CC1 HGFVXRFLCSVTRB-UHFFFAOYSA-N 0.000 claims 3
- KNODUAZVZAOBLI-UHFFFAOYSA-N 5-(6-chloro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(Cl)=CC=C2N1 KNODUAZVZAOBLI-UHFFFAOYSA-N 0.000 claims 3
- HUTREJKNMOVXLQ-UHFFFAOYSA-N 5-(6-tert-butyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 HUTREJKNMOVXLQ-UHFFFAOYSA-N 0.000 claims 3
- 208000003251 Pruritus Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- HVHBGEFITQVWSF-UHFFFAOYSA-N 4-cyclobutyl-5-(4,5-difluoro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C2CCC2)=NC=C1C1=NC2=C(F)C(F)=CC=C2N1 HVHBGEFITQVWSF-UHFFFAOYSA-N 0.000 claims 2
- UBBXIWRZIDNVQT-UHFFFAOYSA-N 5-(4,5-difluoro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-propan-2-ylpyrimidin-2-amine Chemical compound N=1C=C(C=2NC3=CC=C(F)C(F)=C3N=2)C(C(C)C)=NC=1NCCCC1CCN(C)CC1 UBBXIWRZIDNVQT-UHFFFAOYSA-N 0.000 claims 2
- WQFRBIRVVYHUCB-UHFFFAOYSA-N 5-(4,6-dichloro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(Cl)C=C(Cl)C=C2N1 WQFRBIRVVYHUCB-UHFFFAOYSA-N 0.000 claims 2
- FCRFVPZAXGJLPW-UHFFFAOYSA-N 5-(4,6-dimethyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C=C(C)C=C2N1 FCRFVPZAXGJLPW-UHFFFAOYSA-N 0.000 claims 2
- MXPGCFADRFAYSU-UHFFFAOYSA-N 5-(5-chloro-6-methyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(C)=C(Cl)C=C2N1 MXPGCFADRFAYSU-UHFFFAOYSA-N 0.000 claims 2
- RDJBCNLPTKFHQB-UHFFFAOYSA-N 5-(6-methoxy-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(C(=N1)C)=CN=C1NCCCC1CCN(C)CC1 RDJBCNLPTKFHQB-UHFFFAOYSA-N 0.000 claims 2
- LWDKAJGOYUQBRB-UHFFFAOYSA-N 5-[4,6-bis(trifluoromethyl)-1h-benzimidazol-2-yl]-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C(F)(F)F)C=C(C(F)(F)F)C=C2N1 LWDKAJGOYUQBRB-UHFFFAOYSA-N 0.000 claims 2
- QIPRWLNJUHMSKN-UHFFFAOYSA-N 5-[4-chloro-6-(trifluoromethyl)-1h-benzimidazol-2-yl]-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(Cl)C=C(C(F)(F)F)C=C2N1 QIPRWLNJUHMSKN-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- GQNAJZVSAIWLAV-UHFFFAOYSA-N 5-(5-chloro-6-fluoro-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 GQNAJZVSAIWLAV-UHFFFAOYSA-N 0.000 claims 1
- AUWBEHSRDMALLO-UHFFFAOYSA-N 5-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-4-methyl-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 AUWBEHSRDMALLO-UHFFFAOYSA-N 0.000 claims 1
- 208000020576 Adrenal disease Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 1
- 208000027496 Behcet disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012468 Dermatitis herpetiformis Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010015943 Eye inflammation Diseases 0.000 claims 1
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Landscapes
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Applications Claiming Priority (3)
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| US78819006P | 2006-03-31 | 2006-03-31 | |
| PCT/US2007/008216 WO2007117399A2 (en) | 2006-03-31 | 2007-03-30 | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
| EP07754700A EP2007752B1 (en) | 2006-03-31 | 2007-03-30 | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
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| ME01143B true ME01143B (me) | 2013-03-20 |
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| MEP-2010-163A ME01143B (me) | 2006-03-31 | 2007-03-30 | BENZOIMIDAZOL-2-IL PIRIMIDINI l PIRAZINI KAO MODULATORI HISTAMINSKOG H4 RECEPTORA |
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| WO2007117400A2 (en) * | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyridines as modulators of the histamine h4 receptor |
| WO2007117399A2 (en) * | 2006-03-31 | 2007-10-18 | Janssen Pharmaceutica N.V. | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
| WO2007120690A2 (en) * | 2006-04-10 | 2007-10-25 | Janssen Pharmaceutica N.V. | Combination histamine h1r and h4r antagonist therapy for treating pruritus |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009079001A1 (en) * | 2007-12-18 | 2009-06-25 | Janssen Pharmaceutica N.V. | Bicyclic heteroaryl-substituted imidazoles as modulators of the histamine h4 receptor |
| BRPI0915526A2 (pt) * | 2008-06-12 | 2016-01-26 | Janssen Pharmaceutica Nv | uso de um antagonista da histamina h4 para o tratamento de aderências pós-operatórias |
| BRPI0915720A2 (pt) | 2008-06-12 | 2015-08-04 | Janssen Pharmaceutica Nv | Moduladores de diaminopiridina, pirimidina, e piridazina do receptor de histamina h4 |
| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
| CN102137672B (zh) * | 2008-06-30 | 2014-03-26 | 詹森药业有限公司 | 取代的嘧啶衍生物的制备方法 |
| SG192446A1 (en) | 2008-06-30 | 2013-08-30 | Janssen Pharmaceutica Nv | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| AU2013204436B2 (en) * | 2008-06-30 | 2014-12-04 | Janssen Pharmaceutica Nv | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| AR074209A1 (es) | 2008-11-24 | 2010-12-29 | Boehringer Ingelheim Int | Derivados de pirimidina utiles para el tratamiento del cancer |
| TWI491605B (zh) | 2008-11-24 | 2015-07-11 | Boehringer Ingelheim Int | 新穎化合物 |
| EP2201982A1 (en) | 2008-12-24 | 2010-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Histamine H4 receptor antagonists for the treatment of vestibular disorders |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| WO2010115736A2 (en) * | 2009-04-02 | 2010-10-14 | Merck Serono S.A. | Dihydroorotate dehydrogenase inhibitors |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| EP2681200A4 (en) | 2011-03-03 | 2015-05-27 | Zalicus Pharmaceuticals Ltd | INHIBITORS OF BENZIMIDAZOLE TYPE OF SODIUM CHANNEL |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP3378476A1 (en) | 2012-06-08 | 2018-09-26 | Sensorion | H4 receptor inhibitors for treating tinnitus |
| PT2964229T (pt) | 2013-03-06 | 2020-03-23 | Janssen Pharmaceutica Nv | Moduladores de piridina benzimidazol-2-ilo do recetor h4 de histamina |
| GB201504689D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Chemical compounds |
| WO2017076888A1 (en) | 2015-11-03 | 2017-05-11 | Janssen Pharmaceutica Nv | 2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carboxylic acids and amides and methods of making the same |
| KR20240068737A (ko) | 2021-09-27 | 2024-05-17 | 테른스 파마슈티칼스, 인크. | Glp-1r 효능제로서의 벤즈이미다졸 카복실산 |
| AU2022375634A1 (en) | 2021-10-25 | 2024-06-06 | Terns Pharmaceuticals, Inc. | Compounds as glp-1r agonists |
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