JP2009532366A5 - - Google Patents
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- Publication number
- JP2009532366A5 JP2009532366A5 JP2009503074A JP2009503074A JP2009532366A5 JP 2009532366 A5 JP2009532366 A5 JP 2009532366A5 JP 2009503074 A JP2009503074 A JP 2009503074A JP 2009503074 A JP2009503074 A JP 2009503074A JP 2009532366 A5 JP2009532366 A5 JP 2009532366A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- propyl
- piperidin
- benzimidazol
- pyrimidin
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 65
- -1 —CF 3 Chemical group 0.000 claims 26
- 239000000126 substance Substances 0.000 claims 21
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- 229940079593 drug Drugs 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 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 5
- 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 5
- 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 5
- 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 class N=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CC)=NC=1NCCCC1CCN(C)CC1 ZPJUBYMZMHXTGP-UHFFFAOYSA-N 0.000 claims 5
- 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 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
- 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 5
- 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 5
- 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 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 class 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
- 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 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
- 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 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
- 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 5
- 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 class 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 5
- 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 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 class 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
- PDBBSWKMAJWONV-UHFFFAOYSA-N 5-(5,6-difluoro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical class C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=CC(F)=C(F)C=C2N1 PDBBSWKMAJWONV-UHFFFAOYSA-N 0.000 claims 5
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C(Cl)=CC=C2N1 KFCWPNNLWGGGRO-UHFFFAOYSA-N 0.000 claims 5
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 AUWBEHSRDMALLO-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
- 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 class 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 5
- 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 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
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(C)C=C(F)C=C2N1 KYERXDDXJNCIFV-UHFFFAOYSA-N 0.000 claims 5
- 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 5
- 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 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- GSJUMTCTWQSZQV-UHFFFAOYSA-N 2-[4-methyl-2-[3-(1-methylpiperidin-4-yl)propylamino]pyrimidin-5-yl]-3h-benzimidazole-5-carbonitrile Chemical compound C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(C#N)=CC=C2N1 GSJUMTCTWQSZQV-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 class C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 LQWNVGIMAZERKF-UHFFFAOYSA-N 0.000 claims 4
- FJWXBBXPJRGQNY-UHFFFAOYSA-N 4-cyclopropyl-5-(4,6-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]pyrimidin-2-amine Chemical class C1CN(C)CCC1CCCNC(N=C1C2CC2)=NC=C1C1=NC2=C(C)C=C(C)C=C2N1 FJWXBBXPJRGQNY-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
- 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 4
- 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 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
- 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 4
- WQFRBIRVVYHUCB-UHFFFAOYSA-N 5-(4,6-dichloro-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical class C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(Cl)C=C(Cl)C=C2N1 WQFRBIRVVYHUCB-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=C(Cl)C=C(C)C=C2N1 UQRGFHZYHLXDNC-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 GQNAJZVSAIWLAV-UHFFFAOYSA-N 0.000 claims 4
- 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 class C1CN(C)CCC1CCCNC(N=C1C)=NC=C1C1=NC2=CC(C)=C(Cl)C=C2N1 MXPGCFADRFAYSU-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 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 4
- 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 4
- 208000003251 Pruritus Diseases 0.000 claims 4
- 229960001340 histamine Drugs 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 239000002207 metabolite Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- LSOJSTAHVGFZJI-UHFFFAOYSA-N 5-(4,5-dimethyl-1h-benzimidazol-2-yl)-n-[3-(1-methylpiperidin-4-yl)propyl]-4-(trifluoromethyl)pyrimidin-2-amine Chemical class C1CN(C)CCC1CCCNC(N=C1C(F)(F)F)=NC=C1C1=NC2=C(C)C(C)=CC=C2N1 LSOJSTAHVGFZJI-UHFFFAOYSA-N 0.000 claims 2
- 206010020751 Hypersensitivity 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
- 150000004683 dihydrates Chemical class 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 150000004682 monohydrates Chemical class 0.000 claims 2
- 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 class C1CN(C)CCC1CCCNC(N=C1C2CCC2)=NC=C1C1=NC2=C(C)C(F)=CC=C2N1 JPIDROZUGRRXLB-UHFFFAOYSA-N 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
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary 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
- 206010012438 Dermatitis atopic 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
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 208000007514 Herpes zoster Diseases 0.000 claims 1
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000018501 Lymphatic disease Diseases 0.000 claims 1
- 208000000592 Nasal Polyps Diseases 0.000 claims 1
- 206010052437 Nasal discomfort Diseases 0.000 claims 1
- 201000011152 Pemphigus Diseases 0.000 claims 1
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| AU2009257434B2 (en) | 2008-06-12 | 2014-12-11 | Janssen Pharmaceutica Nv | Diamino-pyridine, pyrimidine, and pyridazine modulators of the histamine H4 receptor |
| NZ603074A (en) | 2008-06-12 | 2013-08-30 | Janssen Pharmaceutica Nv | Use of histamine h4 antagonist for the treatment of post-operative adhesions |
| EP2865678A3 (en) | 2008-06-30 | 2015-05-27 | Janssen Pharmaceutica NV | Crystalline hemi-tartrate form of a benzoimidazol-2-yl pyrimidine derivative |
| MX2011000080A (es) | 2008-06-30 | 2011-03-02 | Janssen Pharmaceutica Nv | Proceso para la preparacion de derivados de pirimidina sustituidos. |
| WO2010025314A2 (en) | 2008-08-28 | 2010-03-04 | The General Hospital Corporation | Prevention and treatment of itch with cysteine protease inhibition |
| TWI519533B (zh) | 2010-11-01 | 2016-02-01 | Ｌｇ生命科學有限公司 | １－｛（２Ｓ）－２－胺基－４－［２，４－雙（三氟甲基）－５，８－二氫吡啶并［３，４－ｄ］嘧啶－７（６Ｈ）－基］－４－側氧丁基｝－５，５－二氟哌啶－２－酮酒石酸鹽之水合物 |
| EP2465498A1 (en) | 2010-11-23 | 2012-06-20 | Faes Farma, S.A. | Diphenyl-amine derivatives: uses, process of synthesis and pharmaceutical compositions |
| BR112015021463A8 (pt) | 2013-03-06 | 2019-11-19 | Janssen Pharmaceutica Nv | moduladores de benzoimidazol-2-il pirimidina do receptor histamínico h4,seu uso e composição faramacêutica |
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