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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Claims (33)
1. Hemijsko jedinjenje formule (I) gde svaki R1-4 je nezavisno H, C1-4alkil, C2-4alkenil, C2-4alkinil, fenil, -CF3, -OCF3, -CN, halo, -NO2, -OC1-4alkil, -SC1-4alkil, -S(0)C1-4alkil, -SO2C1-4 -C(0)C1-4alkil, -C(0)fenil, -C(0)NRaRb, -C02C1-4aIkil, -C02H, -C(0)NRaRb ili -NRaRb; gde Ra i Rb su svaki nezavisno H, C1-4alkil ili C3-7cikloalkil; jedan od X1 i X1 je N, a drugi je C-Rc; gde je Rc H, metil, hidroksimetil, dimetilaminometil, etil, propil, izopropil, -CF3, ciklopropil ili ciklobutil; nje 1 ili 2; Z je N, CH ili C(C1-4alkil); R6 je H, C1-6alkil ili monociklični cikloalkil; R8 je H ili C1-4alkil; R9 i R10 su svaki nezavisno H ili C1-4alkil; i Ru je H ili C1-4alkil; farmaceutski prihvatljiva so jedinjenja formule (I) ili hidrat jedinjenja formule (I)
2. Hemijsko jedinjenje prema zahtevu 1, gde svaki R1-2 je nezavisno H, metil, terc-butil, metoksi, -CF3, -CN, fluoro, hloro, metoksikarbonil ili benzoil.
3. Hemijsko jedinjenje prema zahtevu 1, gde j e X2 N.
4. Hemijsko jedinjenje prema zahtevu 1, gde je X1 N.
5. Hemijsko jedinjenje prema zahtevu 1, gde je Rc H, metil, etil, CF3, ciklopropil ili ciklobutil.
6. Hemijsko jedinjenje prema zahtevu 1, gde Rc je H ili metil.
7. Hemijsko jedinjenje prema zahtevu 1, gde je n 1.
8. Hemijsko jedinjenje prema zahtevu 1, gde je Z N ili CH.
9. Hemij sko j edinj enj e prema zahtevu 1, gde j e Z CH.
10. Hemijsko jedinjenje prema zahtevu 1, gde R6 je H, metil, etil, propil, izopropil, ciklopropil ili ciklobutil.
11. Hemijsko jedinjenje prema zahtevu 1, gde je R6 H ili metil.
12. Hemijsko jedinjenje prema zahtevu 1, gde je R H.
13. Hemijsko jedinjenje prema zahtevu 1, gde su R9 i R10 nezavisno H ili metil.
14. Hemijsko jedinjenje prema zahtevu 1, gde su oba R9 i R10 H.
15. Hemijsko jedinjenje prema zahtevu 1, gde je R11 H ili metil.
16. Hemijsko jedinjenje prema zahtevu 1, gde je R11 metil.
17. Hemijsko jedinjenje prema zahtevu 1 izabrano od: [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Difluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3 -(1 -metil-piperidin-4-il)-propil] -amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-metil-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-1 H-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-metil-[3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4-Fluoro-5-metil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-difluoro-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimiđin-2-il]-[3-(l-metil-piperidin-4-iI)-propil] -amin; [5-(4,5-Dimetil-1 H-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Etil-5-(5-fluoro-4-metiI-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propiI]-amin; [5-(5-FIuoro-4-metil-1 H-benzoimidazol-2-il)-4-izopropil-pirimidin-2-iI]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-MetiI-5-(4-metil-lH-benzoimidazol-2-iI)-pirimidin-2-il]-[3-(l-metil-piperidin- 4-il)-propiI]-amin; [5-(lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)- propil]-amin; [5-(5-Fluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [3-(l-Metil-piperidin-4-il)-propil]-[4-metil-5-(5-trifluorometil-1 H-benzimidazol-2-il)-pirimidin-2-il]-amin; [5-(5-terc-Butil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Hloro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propiI]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil] -amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3- (l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dihloro-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperiđin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(5,6-Difluoro-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5*(4,5-Difluoro-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(lH-Benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i njihove faR1-4aceutski prihvatljive soli.
18. Hemijsko jedinjenje prema zahtevu 1, gde hemijsko jedinjenje ima foR1-4ulu (I) ili je faR1-4aceutski prihvatljiva so pomenutog jedinjenja formule (I).
19. Farmaceutska kompozicija za lečenje bolesti, poremećaja ili medicinskog stanja na koje se utiče preko aktivnosti histaminskog H4 receptora, koja sadrži bar jednu efikasnu količinu bar jednog sredstva izabranog od jedinjenja formule (I): gde svaki od R1-4 je nezavisno H, C1-4alkil, C2-4alkenil, C2-4alkiniI, fenil, -CF3, -OCF3, -CN, halo, -N02, -OC1-4alkil, -SC1-4alkil, -S(0)C1-4alkil, -S02C1-4alkil, -C(0)C1-4alkil, -C(0)fenil, -C(0)NRaRb, -C02C1-4aIkil, -C02H, -C(0)NRaRb ili -NRaRb; gde su Ra i Rb svaki nezavisno H, C1-4alkil, ili C3-7cikloalkil; jedan od X1 i X2 je N, a drugi je C-Rc; gde Rc je H, metil, hidroksimetil, dimetilaminometil, etil, propil, izopropil, -CF3, ciklopropil ili ciklobutil; nje 1 ili 2; Z je N, CH ili C(C1-4alkil); R6 je H, C1-6alkil ili monociklični cikoalkil; R8 je H ili C1-4alkil; R9 i R10 su svaki nezavisno H ili C1-4alkil; i R11 je H ili C1-4alkil; farmaceutski prihvatljive soli jedinjenja formule (I) ili hidrata jedinjenja formule (I).
20. Farmaceutska kompozicija prema zahtevu 19, gde je bar jedno pomenuto sredstvo izabrano od: [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazoI-2-iI)-4-metiI-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Difluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-metiI-[3-( 1 -metil-piperidin-4-il)-propil] -amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-metil-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4-Fluoro-5-metil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil- piperidin-4-iI)-propiI]-amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-iI]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-difluoro-lH-benzoimidazol-2-iI)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il] -[3 -(1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-1 H-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Etil-5-(5 -fluoro-4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-iI] - [3 -(1 -metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l- metil-piperidin-4-iI)-propil]-amin; [4-Metil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]- [3 -(1 -metil-piperidin-4-il)-propil]-amin; [5 -(1 H-Benzoimidazol-2-il)-4-metil-pirimidin-2-il] -[3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Fluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil] -amin; [3-(l-Metil-piperidin-4-il)-propil]-[4-metil-5-(5-trifluorometil-lH-benzimidazoI- 2-il)-pirimidin-2-il]-amin; [5-(5-terc-Butil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il] - [3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-4-metil-lH-benzoimidazoI-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(6-Fluoro-4-metil-lH-benzoimidazo]-2-il)-4-trifluorometi]-pirimidin-2-il]-[3- (l-metil-piperidin-4-iI)-propil]-amin; [5-(4,6-Dihloro-lH-benzoimiđazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(5,6-Difluoro-lH-benzoimidazol-2-il)-4-trifluorometiI-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-izopropiI-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i njihove farmaceutski prihvatljive soli.
21. Sredstvo izabrano objedinjenja formule (I): gde svaki od R1-4 je nezavisno H, C1-4alkil, C2-4alkenil, C2-4alkinil, fenil, -CF3, -OCF3, -CN, halo, -NO2, -OC1-4alkil, -SC1-4akil, -S(0)C1-4alkil, -SC2C1-4alkil, -C(0)C1-4alkil, -C(0)fenil, -C(0)NRaRb, -C02C1-4alkil, -C02H, -C(0)NRaRb ili -NRaRb; gde su Ra i Rb svaki nezavisno H, C1-4alkil, ili C3-7cikloalkil; jedan od X1 i X2 je N, a drugi je C-Rc; gde Rc je H, metil, hidroksimetil, dimetilaminometil, etil, propil, izopropil, -CF3, ciklopropil ili ciklobutil; nje 1 ili 2; Z je N, CH ili C(C1-4alkil); R6 je H, C1-6alkil ili monociklični cikloalkil; R8 je H ili C1-4alkil; R9 i R10 su svaki nezavisno H ili C1-4alkil; i R11 je H ili C1-4alkil; farmaceutski prihvatljive soli jedinjenja formule (I) za upotrebu u postupku lečenja subjekta koji pati od ili kod koga je dijagnozirana bolest, poremećaja ili medicinskog stanja na koje se utiče preko aktivnosti histaminskog H4 receptora, a pomenuti postupak se sastoji od davnja subjektu kome je potrebno takvo lečenje efikasne količine bar jednog od pomenutih sredstava.
22. Sredstvo za upotrebu u postupku prema zahtevu 21, gde je bar jedno od sredstava izabrano od: [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimiđin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-i!)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-metil-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-metil-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4-Fluoro-5-metil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Dimetil-1 H-benzoimidazol-2-il)-4-izopropiI-pirimidin-2-il]-[3-( 1 -metil-piperiđin-4-iI)-propil] -amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-iI]-[3-(l-metil- piperidin-4-iI)-propil]-amin; [4-Ciklobutil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-difluoro-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metiI- piperidin-4-il)-propil]-amin; [4-CiklobutiI-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Etil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-iI]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Metil-5-(4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin- 4-il)-propil]-amin; [5-(lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)- propil]-amin; [5-(5-Fluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [3-(l-Metil-piperidin-4-il)-propil]-[4-metil-5-(5-trifluorometil-lH-benzimidazol- 2-il)-pirimidin-2-il]-amin; [5-(5-terc-Butil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(5-Hloro-4-metil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-iI]-[3-( 1 -metil-piperiđin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3- (l-metil-piperidin-4-il)-propil]-amin; [5-(6-FIuoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3- (l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dihloro-1 H-benzoimidazol-2-il)-4-trifluorometil-pirimiđin-2-il]-[3 -(1 -metil-piperidin-4-il)-propiI]-amin; [5-(4,5-Diraetil-l H-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propiI]-amin; [5-(5,6-Difluoro-l H-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-iI]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-izopropiI-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-iI)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propiI]-amin; i njihove farmaceutski prihvatljive soli.
23. Sredstvo prema zahtevu 21, što je bolest, poremećaj ili medicinsko stanje zapaljenje.
24. Sredstvo prema zahtevu 21, što je bolest, poremećaj ili medicinsko stanje izabrano iz grupe koja se sastoji od inflamatomih poremećaja, alergijskih poremećaja, deR1-4atoloških poremećaja, autoimune bolesti, limfatičkih poremećaja i imunodeficijentnih poremećaja.
25. Sredstvo prema zahtevu 21, što je bolest, poremećaj ili medicinsko stanje izabrano od: alergije, astme, suvog oka, hronične bolesti plućne opstrukcije (COPD - chronic obstructed pulmonary disease), ateroskleroze, reumatoidnog artritisa, multiple skleroze, inflamatrone bolesti creva, kolitisa, Kronove bolesti, ulceroznog kolitisa, psorijaze, pruritusa, svraba kože, atopičnog deR1-4atitisa, urtikarije, koprivnjače, zapaljenja oka, konjuktivitisa, nazalnih polipa, alergijskog rinitisa, nazalnog svrba, sklerodeR1-4e, autoimunih bolesti tiroidee, imuno posredovane šećerne bolesti, lupusa, miastenije gravis, autoimune neuropatije, Žilijan Bareovog sindroma, autoimunog uveitisa, autoimune hemolitičke anemije, pemiciozne anemije, autoimune trombocitopenije, temporalnogi artritisa, anti-fosfolipidnog sindroma, vaskulitisa, Vagenerove granulomatoze, Behčetove bolesti, dermatitis herpetiformisa, pemfigus vulgarisa, vitiliga, primame ciroze jetre, autoimunog hepatitisa, autoimunog oophoritisa, autoimunog orchitisa, autoimune bolesti adrenalne žlezde, polimiozitisa, dermatomiozitisa, spondiloartropatije, ankiloznog spondilitisa i Sjogrenov sindroma.
26. Sredstvo prema zahtevu 21, što je bolest, poremećaj ili medicinsko stanje izabrano od: alergije, astme, autoimune bolesti i pruritusa.
27. Sredstvo izabrano od jedinjenja formule (I): gde svaki od R1-4 je nezavisno H, C1-4alkil, C2-4alkenil, C2-4alkinil, fenil, -CF3, -OCF3, -CN, halo, -N02, -OC1-4alkil, -SC1-4alkil, -S(0)C1-4alkil, -S02C1-4alkil, -C(0)C1-4alkil, -C(0)fenil, -C(0)NRaRb, -C02C1-4alkil, -C02H, -C(0)NRaRb ili -NRaRb; gde su Ra i Rb svaki nezavisno H, C1-4alkil, ili C3-7cikloalkil; jedan od X1 i X2 je N, a drugi je C-Rc; gde Rc je H, metil, hidroksimetil, dimetilaminometil, etil, propil, izopropil, -CF3, ciklopropil ili ciklobutil; nje 1 ili 2; Z je N, CH ili C(C1-4alkil); R6 je H, C1-6alkil ili monociklični cikloalkil; R8 je H ili C1-4alkil; R9 i R10 su svaki nezavisno H ili C1-4alkil; i Rn je H ili C1-4alkil; i prihvatljiva so jedinjenja formule (I) za upotrebu u postupku modulacije aktivnosti histaminskog H4 receptora, a pomenuti postupak obuhvata izlaganje histaminskog H4 receptora efikasnoj količini bar jednog od pomenutih sredstava.
28. Sredstvo za upotrebu u postupku prema zahtevu 27, što je pomenuto sredstvo bar jedno od [5-(5-Fluoro-4-metil-l H-benzoimidazol-2-il)-4-metil-pirimiđin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-prop,il]-amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-rnetil-piperidin-4-il)-propil] -amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperiđin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-metil-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-metil-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4-Fluoro-5-metil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il] -[3 -(1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-dimetil-l H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-difluoro-lH-benzoimiđazol-2-il)-pirirnidin-2-il]-[3-(l-metil- piperidin-4-il)-propiI]-amin; [5-(5-Fluoro-4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,6-đimetil-lH-benzoiniidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-iI]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Etil-5-(5-fluoro-4-metiI-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Metil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(lH-Benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)- propil]-amin; [5-(5-Fluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [3-(l-Metil-piperidin-4-il)-propil]-[4-metil-5-(5-trifluorometil-lH-benzimidazol- 2-il)-pirimidin-2-il]-amin; [5-(5-terc-Butil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Hloro-4-metil-1 H-benzoimidazol-2-iI)-4-metil-pirimidin-2-iI]-[3-( 1 -metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propiI]-amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimiđin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dihloro-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l- metiI-piperidin-4-il)-propil]-amin; [5-(5,6-Difluoro-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(I- metil-piperidin-4-il)-propiI]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propiI]-amin; [5-(lH-Benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i njihove soli.
29. Hemijsko jedinjenje prema zahtevu 1 izabrano od [5-(4,6-Bis-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; 2- {4-Metil-2-[3-( 1 -metil-piperidin-4-il)-propilamino]-piridmidin-5-il} -1H-benzimidazol-5-karbonitril; [5-(5 -Metoksi-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il] - [3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4-Hloro-6-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-6-fluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Hloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin- 4-il)-propil]-amin; [5-(5,6-Dihloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-EtiI-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4,5-dimetil-lH-benzoimiđazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(6-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-iI]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(6-Hloro-5-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i [5-(4-Hloro-6-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i njihova farmaceutski prihvatljiva so.
30. Farmaceutska kompozicija prema zahtevu 19, što je bar jedno sredstvo izabrano od [5-(4,6-Bis-trifluorometil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l -metil-piperidin-4-il)-propil]-amin; 2- {4-Metil-2-[3-( 1 -metil-piperidin-4-il)-propilamino] -piridmidin-5-il} -1H-benzimidazol-5 -karbonitril; [5-(5-Metoksi-IH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metiI- piperidin-4-il)-propil]-amin; [5-(4-Hloro-6-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirirnidin-2-il]-[3-(1 -metiI-piperidin-4-il)-propil]-amin; [5-(5-HIoro-6-fluoro-1 H-benzoimidazol-2-il)-4-metil-pifimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(5,6-Dihloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-1 H-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Etil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il] -[3 -(1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3 -(1 -metil-piperidin-4-i l)-propil] -amin; [4-Ciklopropil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(6-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-CikIopropil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [5-(6-Hloro-5-metil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; i [5-(4-Hloro-6-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; i njihova farmaceutski prihvatljiva so.
31. Sredstvo za upotrebu u postupku prema zahtevu 13, što je bar jedno sredstvo izabrano od: [5-(4,6-Bis-trifluorometil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; 2-{4-Metil-2-[3-(l-metil-piperidin-4-il)-propilamino]-piridmidin-5-il}-lH-benzimidazol-5-karbonitril; [5-(5-Metoksi-lH-benzoimidazoI-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4-Hloro-6-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-6-fluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin- 4-il)-propil]-amin; [5-(5,6-Dihloro-lH-benzoimidazol-2-iI)-4-metil-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propi 1] -amin; [4-Etil-5-(4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4- il)-propil]-amin; [4-Ciklopropil-5-(4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [4-Ciklopropil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(6-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4,6-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(5-fluoro-4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(6-Hloro-5-metil-lH-benzoimidazol-2-il)-4-metiI-pirimiđin-2-il]-[3-(l-metil-piperiđin-4-il)-propiI]-amin; i [5-(4-Hloro-6-metiI-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l -metil-piperidin-4-il)-propil]-amin; i njihova farmaceutski prihvatljiva so.
32. Hemihidratna so jedinjenja formule (I) prema zahtevu I.
33. Hemijsko jedinjenje prema zahtevu 1, izabrano od [5-(5-Fluoro-4-metil-1 H-benzoimidazol-2-il)-4-metiI-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metiI-piperidin-4-il)-propiI] -amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperiđin-4-il)-propil] -amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Difluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-metil-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-metil-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-1 H-benzoimidazol-2-il)-4-etiI-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4-Fluoro-5-metil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-1 H-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dimetil-lH-benzoimidazoI-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-dimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil- piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(4,5-difluoro-lH-benzoimidazol-2-iI)-pirimidin-2-il]-[3-(l-metiI-piperidin-4-il)-propil]-amin; [5-(5-Fluoro-4-metil-lH-benzoimidazoI-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5-(5-fluoro-4-metiI-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l- metil-piperidin-4-il)-propil]-amin; [4-Ciklobutil-5 -(4,6-dimetil-1 H-benzoimidazol-2-il)-pirimidin-2-il] - [3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-propil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Etil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-1 H-benzoimidazol-2-iI)-4-izopropil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Metil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(lH-Benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propiI]-amin; [5-(5-Fluoro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [3-(l-Metil-piperidin-4-il)-propil]-[4-metil-5-(5-trifluorometil-lH-benzimidazol-2-il)-pirimidin-2-il] -amin; [5-(5-terc-Butil-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [5-(5-Hloro-4-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(5-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(6-Fluoro-4-metil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil]-amin; [5-(4,6-Dihloro-1 H-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]- [3 -(1 -metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(5,6-Difluoro-lH-benzoimidazol-2-il)-4-trifluorometil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Difluoro-lH-benzoimidazol-2-il)-4-izopropil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(lH-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,5-Dimetil-lH.-benzoimidazol-2-il)-pirazin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(4,6-Bis-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; 2-{4-Metil-2-[3-(l-metil-piperidin-4-il)-propilamino]-piridmidin-5-il}-lH-benzimidazol-5-karbonitril; [5-(5-Metoksi-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4-Hloro-6-trifluorometil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(1 -metil-piperidin-4-il)-propil] -amin; [5-(5-Hloro-6-fluoro-1 H-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil] -amin; [5-(5-Hloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(5,6-Dihloro-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4,6-Dimetil-lH-benzoimidazol-2-il)-4-etil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Etil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(4,5-dimetil-1 H-benzoimidazol-2-il)-pirimidin-2-il]- [3-( 1 -metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(6-fluoro-4-metil-1 H-benzoimidazol-2-il)-pirimidin-2-il]-[3-( 1-metil-piperidin-4-iI)-propil]-amin; [4-Ciklopropil-5-(4,6-đimetil-lH-benzoimidazol-2-il)-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [4-Ciklopropil-5-(5-fluoro-4-metil-lH-benzoimidazol-2-il)-pirirnidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; [5-(6-Hloro-5-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil] -amin; [5-(4-Hloro-6-metil-lH-benzoimidazol-2-il)-4-metil-pirimidin-2-il]-[3-(l-metil-piperidin-4-il)-propil]-amin; i monohidrati, dihidrati i njihovih soli.
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| PCT/US2007/008216 WO2007117399A2 (en) | 2006-03-31 | 2007-03-30 | Benzoimidazol-2-yl pyrimidines and pyrazines as modulators of the histamine h4 receptor |
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