HRP20120290T1 - NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 - Google Patents
NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 Download PDFInfo
- Publication number
- HRP20120290T1 HRP20120290T1 HR20120290T HRP20120290T HRP20120290T1 HR P20120290 T1 HRP20120290 T1 HR P20120290T1 HR 20120290 T HR20120290 T HR 20120290T HR P20120290 T HRP20120290 T HR P20120290T HR P20120290 T1 HRP20120290 T1 HR P20120290T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridin
- trifluoromethyl
- diazabicyclo
- dihydro
- connection
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 21
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 14
- 239000002253 acid Substances 0.000 claims abstract 13
- -1 trifluoromethoxy radical Chemical class 0.000 claims abstract 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 5
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- GVUVUWRTJAHUNE-UHFFFAOYSA-N 6-[3-[2-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 GVUVUWRTJAHUNE-UHFFFAOYSA-N 0.000 claims 3
- 150000004702 methyl esters Chemical class 0.000 claims 3
- IGQZGIHYQUNTFP-UHFFFAOYSA-N 2-[3-[2-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 IGQZGIHYQUNTFP-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- ZQNNLLZPPHBUKK-UHFFFAOYSA-N 1-[3-[4-chloro-3-(trifluoromethyl)phenyl]-2,5-dihydropyrrol-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC(=CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 ZQNNLLZPPHBUKK-UHFFFAOYSA-N 0.000 claims 1
- LYOAPQOBFXIYDD-UHFFFAOYSA-N 1-[4-(2,3-dichlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C(=C(Cl)C=CC=1)Cl)C2 LYOAPQOBFXIYDD-UHFFFAOYSA-N 0.000 claims 1
- CZTLZBWOSKNQQE-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(Cl)C=CC=1)C2 CZTLZBWOSKNQQE-UHFFFAOYSA-N 0.000 claims 1
- ZHODRFQYSJZRFV-UHFFFAOYSA-N 1-[4-(3-methylphenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyrazin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound CC1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=NC=3)C2)=C1 ZHODRFQYSJZRFV-UHFFFAOYSA-N 0.000 claims 1
- GSLGDCPSILDSJM-UHFFFAOYSA-N 1-[4-(4-bromophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-chloroethanone Chemical compound C1N(C(=O)CCl)CCC(C=2C=CC(Br)=CC=2)=C1 GSLGDCPSILDSJM-UHFFFAOYSA-N 0.000 claims 1
- MTINWZMEGCBWBN-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyrimidin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=CC(Cl)=CC=C1C1=CCN(C(=O)CN2CC3CCC(N3C=3N=CC=CN=3)C2)CC1 MTINWZMEGCBWBN-UHFFFAOYSA-N 0.000 claims 1
- AKIKCUKQLSCUTH-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[2-[5-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=CC(Cl)=CC=3)CC2C1 AKIKCUKQLSCUTH-UHFFFAOYSA-N 0.000 claims 1
- DESCDSSPMUHXNZ-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[3-[5-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CC(N2CC(=O)N3CC=C(CC3)C=3C=CC(Cl)=CC=3)CCC2C1 DESCDSSPMUHXNZ-UHFFFAOYSA-N 0.000 claims 1
- GBSPHLVVIYDDOC-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=CC(Cl)=CC=1)C2 GBSPHLVVIYDDOC-UHFFFAOYSA-N 0.000 claims 1
- YYCNPFZAOJVUDV-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-2-[8-[5-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=CC(Cl)=CC=1)C2 YYCNPFZAOJVUDV-UHFFFAOYSA-N 0.000 claims 1
- RVJKYIDMWJFVJT-UHFFFAOYSA-N 1-[4-[3,5-bis(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C2 RVJKYIDMWJFVJT-UHFFFAOYSA-N 0.000 claims 1
- NAPCQMWDYHTNHH-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-[5-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C=CC=3)C(F)(F)F)CC2C1 NAPCQMWDYHTNHH-UHFFFAOYSA-N 0.000 claims 1
- VVSHZPSVRCEGDW-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[3-[5-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-8-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CC(N2CC(=O)N3CC=C(CC3)C=3C=C(C=CC=3)C(F)(F)F)CCC2C1 VVSHZPSVRCEGDW-UHFFFAOYSA-N 0.000 claims 1
- CKDHBGOJZPUYCV-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-[3-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3C(=CC=CN=3)C(F)(F)F)C2)=C1 CKDHBGOJZPUYCV-UHFFFAOYSA-N 0.000 claims 1
- YUNYQUCFVIZACT-UHFFFAOYSA-N 1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-[5-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C=CC=1)C(F)(F)F)C2 YUNYQUCFVIZACT-UHFFFAOYSA-N 0.000 claims 1
- ZTQLZZPKUHHRPJ-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(2-pyridin-2-yl-2,5-diazabicyclo[2.2.1]heptan-5-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2C3CC(N(C3)C=3N=CC=CC=3)C2)=C1 ZTQLZZPKUHHRPJ-UHFFFAOYSA-N 0.000 claims 1
- RMOBYPSNBJNRPW-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyrazin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=NC=3)C2)=C1 RMOBYPSNBJNRPW-UHFFFAOYSA-N 0.000 claims 1
- LFEYBDYJBBFPDI-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyridin-3-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3C=NC=CC=3)C2)=C1 LFEYBDYJBBFPDI-UHFFFAOYSA-N 0.000 claims 1
- WHQBCKFIQDZNSZ-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyrimidin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=CN=3)C2)=C1 WHQBCKFIQDZNSZ-UHFFFAOYSA-N 0.000 claims 1
- LUMHNBAFUXBCKZ-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-pyrimidin-5-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3C=NC=NC=3)C2)=C1 LUMHNBAFUXBCKZ-UHFFFAOYSA-N 0.000 claims 1
- XRSKWGIMXDGIPB-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-quinolin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=C4C=CC=CC4=CC=3)C2)=C1 XRSKWGIMXDGIPB-UHFFFAOYSA-N 0.000 claims 1
- SNEPXQJUVLYMTN-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-(8-quinolin-3-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3C=C4C=CC=CC4=NC=3)C2)=C1 SNEPXQJUVLYMTN-UHFFFAOYSA-N 0.000 claims 1
- KXPPRNJXWUSNFF-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-(5-fluoropyrimidin-2-yl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CC2C1 KXPPRNJXWUSNFF-UHFFFAOYSA-N 0.000 claims 1
- MYSJLMZVZNTHLP-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-(5-fluoropyrimidin-2-yl)-2,5-diazabicyclo[2.2.2]octan-5-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CCC2C1 MYSJLMZVZNTHLP-UHFFFAOYSA-N 0.000 claims 1
- GTKFRLUSMBHLGD-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-[5-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CC2C1 GTKFRLUSMBHLGD-UHFFFAOYSA-N 0.000 claims 1
- QQNWIVULRMDYDF-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-[6-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethanone Chemical compound N1=NC(C(F)(F)F)=CC=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CC2C1 QQNWIVULRMDYDF-UHFFFAOYSA-N 0.000 claims 1
- XEAQKQRVKDGRNV-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[2-[6-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.2]octan-5-yl]ethanone Chemical compound N1=NC(C(F)(F)F)=CC=C1N1C(CN2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CCC2C1 XEAQKQRVKDGRNV-UHFFFAOYSA-N 0.000 claims 1
- ZITDWWQNCHCBBQ-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[3-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-8-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1CC(N2CC(=O)N3CC=C(CC3)C=3C=C(C(Cl)=CC=3)C(F)(F)F)CCC2C1 ZITDWWQNCHCBBQ-UHFFFAOYSA-N 0.000 claims 1
- XNMACNUVKKDVTN-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 XNMACNUVKKDVTN-UHFFFAOYSA-N 0.000 claims 1
- WMVPUFWFSOVFML-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 WMVPUFWFSOVFML-UHFFFAOYSA-N 0.000 claims 1
- FNEFGWXQCQJCIF-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-(6-fluoropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound C1=NC(F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 FNEFGWXQCQJCIF-UHFFFAOYSA-N 0.000 claims 1
- VYVWCIUKTRKUMX-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-[5-(trifluoromethyl)pyridin-2-yl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 VYVWCIUKTRKUMX-UHFFFAOYSA-N 0.000 claims 1
- IEQOEKWSADUXCI-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[8-[6-(trifluoromethyl)pyridin-3-yl]-3,8-diazabicyclo[3.2.1]octan-3-yl]ethanone Chemical compound C1=NC(C(F)(F)F)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 IEQOEKWSADUXCI-UHFFFAOYSA-N 0.000 claims 1
- CXBAFNOYPXNBAE-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-[9-[5-(trifluoromethyl)pyridin-2-yl]-3,9-diazabicyclo[3.3.1]nonan-3-yl]ethanone Chemical compound N1=CC(C(F)(F)F)=CC=C1N1C2CCCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 CXBAFNOYPXNBAE-UHFFFAOYSA-N 0.000 claims 1
- XJTQPGZMIOAAIU-UHFFFAOYSA-N 1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-3-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]propan-1-one Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CCC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 XJTQPGZMIOAAIU-UHFFFAOYSA-N 0.000 claims 1
- FNEZDXFWERSPBM-UHFFFAOYSA-N 2-(3-pyrazin-2-yl-3,8-diazabicyclo[3.2.1]octan-8-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2C3CCC2CN(C3)C=2N=CC=NC=2)=C1 FNEZDXFWERSPBM-UHFFFAOYSA-N 0.000 claims 1
- FDHLQGAHHRNOED-UHFFFAOYSA-N 2-(8-pyrazin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=NC=3)C2)=C1 FDHLQGAHHRNOED-UHFFFAOYSA-N 0.000 claims 1
- PNFIJSYMMOSWST-UHFFFAOYSA-N 2-(8-pyridin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=CC=3)C2)=C1 PNFIJSYMMOSWST-UHFFFAOYSA-N 0.000 claims 1
- OILNWQAFXRIUQJ-UHFFFAOYSA-N 2-(8-pyrimidin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC=CN=3)C2)=C1 OILNWQAFXRIUQJ-UHFFFAOYSA-N 0.000 claims 1
- RQGCXCMPQHXNAI-UHFFFAOYSA-N 2-(8-pyrimidin-4-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CN=CC=3)C2)=C1 RQGCXCMPQHXNAI-UHFFFAOYSA-N 0.000 claims 1
- RYLJDXKMYJEPSW-UHFFFAOYSA-N 2-(8-quinolin-2-yl-3,8-diazabicyclo[3.2.1]octan-3-yl)-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=C4C=CC=CC4=CC=3)C2)=C1 RYLJDXKMYJEPSW-UHFFFAOYSA-N 0.000 claims 1
- PMDWIYHHPYFAMF-UHFFFAOYSA-N 2-[8-(5-chloropyridin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC(Cl)=CC=3)C2)=C1 PMDWIYHHPYFAMF-UHFFFAOYSA-N 0.000 claims 1
- BWCQIIKSBMKUSK-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[3-[3-(trifluoromethyl)phenyl]-2,5-dihydropyrrol-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC(=CC1)C=1C=C(C=CC=1)C(F)(F)F)C2 BWCQIIKSBMKUSK-UHFFFAOYSA-N 0.000 claims 1
- YKUAQCUBZVRUSF-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-(3-methoxyphenyl)-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound COC1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC(F)=CN=3)C2)=C1 YKUAQCUBZVRUSF-UHFFFAOYSA-N 0.000 claims 1
- RXDGIAJLDHQRMP-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-(3-methylphenyl)-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound CC1=CC=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3N=CC(F)=CN=3)C2)=C1 RXDGIAJLDHQRMP-UHFFFAOYSA-N 0.000 claims 1
- YAPMFXQDXUEHQA-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-[3-(trifluoromethoxy)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(OC(F)(F)F)C=CC=1)C2 YAPMFXQDXUEHQA-UHFFFAOYSA-N 0.000 claims 1
- TYSGJBCSXQPARS-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C=CC=1)C(F)(F)F)C2 TYSGJBCSXQPARS-UHFFFAOYSA-N 0.000 claims 1
- YRYXHSFZEXSASR-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-[4-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=CC(=CC=1)C(F)(F)F)C2 YRYXHSFZEXSASR-UHFFFAOYSA-N 0.000 claims 1
- DEDUATFAWOTWOW-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[5-[2-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC(=CCC1)C=1C(=CC=CC=1)C(F)(F)F)C2 DEDUATFAWOTWOW-UHFFFAOYSA-N 0.000 claims 1
- XJDLEXLOSJGILU-UHFFFAOYSA-N 2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[5-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound N1=CC(F)=CN=C1N1C2CCC1CN(CC(=O)N1CC(=CCC1)C=1C=C(C=CC=1)C(F)(F)F)C2 XJDLEXLOSJGILU-UHFFFAOYSA-N 0.000 claims 1
- XVKKSSHZYOWBQK-UHFFFAOYSA-N 2-[8-(6-chloropyridin-3-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]-1-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(C=2CCN(CC=2)C(=O)CN2CC3CCC(N3C=3C=NC(Cl)=CC=3)C2)=C1 XVKKSSHZYOWBQK-UHFFFAOYSA-N 0.000 claims 1
- HQIOKKAJAOKFAA-UHFFFAOYSA-N 2-chloro-1-[4-(2-methoxyphenyl)-3,6-dihydro-2h-pyridin-1-yl]ethanone Chemical compound COC1=CC=CC=C1C1=CCN(C(=O)CCl)CC1 HQIOKKAJAOKFAA-UHFFFAOYSA-N 0.000 claims 1
- MLBODGCLRWYRAQ-UHFFFAOYSA-N 3-[1-[2-[8-(5-fluoropyrimidin-2-yl)-3,8-diazabicyclo[3.2.1]octan-3-yl]acetyl]-3,6-dihydro-2h-pyridin-5-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2CN(CCC=2)C(=O)CN2CC3CCC(N3C=3N=CC(F)=CN=3)C2)=C1 MLBODGCLRWYRAQ-UHFFFAOYSA-N 0.000 claims 1
- BBEKMDKAIAQDLY-UHFFFAOYSA-N 6-[3-[2-[4-[4-chloro-3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-2-oxoethyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1N1C2CCC1CN(CC(=O)N1CC=C(CC1)C=1C=C(C(Cl)=CC=1)C(F)(F)F)C2 BBEKMDKAIAQDLY-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
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- Transplantation (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0803299A FR2932482B1 (fr) | 2008-06-13 | 2008-06-13 | Nouveaux derives de (phenyl-3,6-dihydro-2h-pyridinyl)- (piperazinyl ponte)-1-alcanone et leur utilisation comme inhibiteurs de p75 |
| PCT/FR2009/051118 WO2009150388A1 (fr) | 2008-06-13 | 2009-06-12 | NOUVEAUX DERIVES DE (PIPERAZINYL PONTE)-1-ALCANONE ET LEUR UTILISATION COMME INHIBITEURS DE p75 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120290T1 true HRP20120290T1 (hr) | 2012-04-30 |
Family
ID=40305395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20120290T HRP20120290T1 (hr) | 2008-06-13 | 2012-04-02 | NOVI DERIVATI (PREMOŠTENI PIPERAZINIL)-1-ALKANONA I NJIHOVA UPOTREBA KAO INHIBITORA p75 |
Country Status (39)
| Country | Link |
|---|---|
| US (2) | US8193190B2 (de) |
| EP (1) | EP2297148B8 (de) |
| JP (1) | JP5476373B2 (de) |
| KR (1) | KR101642526B1 (de) |
| CN (1) | CN102124006B (de) |
| AR (1) | AR072103A1 (de) |
| AT (1) | ATE540039T1 (de) |
| AU (1) | AU2009259121B2 (de) |
| BR (1) | BRPI0915126B8 (de) |
| CA (1) | CA2727669C (de) |
| CL (1) | CL2010001429A1 (de) |
| CO (1) | CO6280535A2 (de) |
| CR (1) | CR11832A (de) |
| CY (1) | CY1112610T1 (de) |
| DK (1) | DK2297148T3 (de) |
| DO (2) | DOP2010000380A (de) |
| EA (1) | EA019074B1 (de) |
| EC (1) | ECSP10010672A (de) |
| ES (1) | ES2379685T3 (de) |
| FR (1) | FR2932482B1 (de) |
| HK (1) | HK1158631A1 (de) |
| HR (1) | HRP20120290T1 (de) |
| IL (1) | IL209902A (de) |
| JO (1) | JO2774B1 (de) |
| MA (1) | MA32474B1 (de) |
| MX (1) | MX2010013695A (de) |
| MY (1) | MY150988A (de) |
| NI (1) | NI201000215A (de) |
| NZ (1) | NZ589840A (de) |
| PE (1) | PE20110154A1 (de) |
| PL (1) | PL2297148T3 (de) |
| PT (1) | PT2297148E (de) |
| RS (1) | RS52262B (de) |
| SI (1) | SI2297148T1 (de) |
| SV (1) | SV2010003755A (de) |
| TW (1) | TWI432433B (de) |
| UA (1) | UA101979C2 (de) |
| UY (1) | UY31893A (de) |
| WO (1) | WO2009150388A1 (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2931223B1 (fr) | 2008-05-16 | 2010-08-20 | Air Liquide | Dispositif distributeur de gaz sous pression, ensemble comprenant un tel dispositif et dispositif de commande, recipient pourvu d'un tel dispositif distributeur |
| FR2932481B1 (fr) * | 2008-06-13 | 2010-10-08 | Sanofi Aventis | Derives de 4-{2-°4-phenyl-3,6-dihydro-2h-pyridin-1-yl!-2- oxo-alkyl}-1-piperazin-2-one, leur preparation et leur application en therapeutique. |
| FR2953836B1 (fr) | 2009-12-14 | 2012-03-16 | Sanofi Aventis | Nouveaux derives (heterocycle-tetrahydro-pyridine)-(piperazinyl)-1-alcanone et (heterocycle-dihydro-pyrrolidine)-(piperazinyl)-1-alcanone et leur utilisation comme inhibiteurs de p75 |
| FR2953839A1 (fr) | 2009-12-14 | 2011-06-17 | Sanofi Aventis | Nouveaux derives d'(heterocycle-piperidine condensee)-(piperazinyl)-1alcanone ou d'(heterocycle-pyrrolidine condensee)-(piperazinyl)-1alcanone et leur utilisation comme inhibiteurs de p75 |
| EP2606894A1 (de) | 2011-12-20 | 2013-06-26 | Sanofi | Neuartige therapeutische Verwendung von p75-Rezeptorantagonisten |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3236243A1 (de) * | 1982-09-30 | 1984-04-05 | Merck Patent Gmbh, 6100 Darmstadt | Schwefelhaltige indolderivate |
| FR2744448B1 (fr) * | 1996-02-02 | 1998-04-24 | Pf Medicament | Nouvelles piperidines derivees d'aryl piperazine, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| US6613942B1 (en) * | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| BR9810378A (pt) * | 1997-07-01 | 2000-08-29 | Novo Nordisk As | Composto,uso do mesmo, composição farmacêutica, e, processos de tratar a diabete do tipo i ou do tipo ii, de tratar a hiperglicemia, e de diminuir a glicose do sangue em um mamìfero |
| WO2000059893A1 (en) | 1999-04-06 | 2000-10-12 | Krenitsky Pharmaceuticals Inc. | Neurotrophic thio substituted pyrimidines |
| UA77526C2 (en) * | 2002-06-07 | 2006-12-15 | Sanofi Aventis | Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy |
| FR2862967B1 (fr) * | 2003-12-01 | 2006-08-04 | Sanofi Synthelabo | Derives de (4-phenylpiperazin-1-yl)acylpiperidine, leur preparation et leur application en therapeutique |
| FR2862968B1 (fr) | 2003-12-01 | 2006-08-04 | Sanofi Synthelabo | Derives de 4-[(arylmethyl)aminomethyl]piperidine, leur preparation et leur application en therapeutique |
| FR2932481B1 (fr) * | 2008-06-13 | 2010-10-08 | Sanofi Aventis | Derives de 4-{2-°4-phenyl-3,6-dihydro-2h-pyridin-1-yl!-2- oxo-alkyl}-1-piperazin-2-one, leur preparation et leur application en therapeutique. |
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2008
- 2008-06-13 FR FR0803299A patent/FR2932482B1/fr not_active Expired - Fee Related
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2009
- 2009-06-04 JO JO2009204A patent/JO2774B1/en active
- 2009-06-11 AR ARP090102110A patent/AR072103A1/es active IP Right Grant
- 2009-06-11 TW TW098119564A patent/TWI432433B/zh active
- 2009-06-12 PL PL09761939T patent/PL2297148T3/pl unknown
- 2009-06-12 PE PE2010001120A patent/PE20110154A1/es not_active Application Discontinuation
- 2009-06-12 CN CN200980131366.XA patent/CN102124006B/zh active Active
- 2009-06-12 MX MX2010013695A patent/MX2010013695A/es active IP Right Grant
- 2009-06-12 AU AU2009259121A patent/AU2009259121B2/en active Active
- 2009-06-12 MY MYPI20105850 patent/MY150988A/en unknown
- 2009-06-12 KR KR1020117000792A patent/KR101642526B1/ko active IP Right Grant
- 2009-06-12 CA CA2727669A patent/CA2727669C/fr active Active
- 2009-06-12 PT PT09761939T patent/PT2297148E/pt unknown
- 2009-06-12 SI SI200930220T patent/SI2297148T1/sl unknown
- 2009-06-12 DK DK09761939.9T patent/DK2297148T3/da active
- 2009-06-12 EP EP09761939A patent/EP2297148B8/de active Active
- 2009-06-12 RS RS20120137A patent/RS52262B/en unknown
- 2009-06-12 UA UAA201100370A patent/UA101979C2/ru unknown
- 2009-06-12 JP JP2011513038A patent/JP5476373B2/ja active Active
- 2009-06-12 ES ES09761939T patent/ES2379685T3/es active Active
- 2009-06-12 BR BRPI0915126A patent/BRPI0915126B8/pt active Search and Examination
- 2009-06-12 UY UY0001031893A patent/UY31893A/es not_active Application Discontinuation
- 2009-06-12 EA EA201170016A patent/EA019074B1/ru not_active IP Right Cessation
- 2009-06-12 AT AT09761939T patent/ATE540039T1/de active
- 2009-06-12 NZ NZ589840A patent/NZ589840A/xx not_active IP Right Cessation
- 2009-06-12 WO PCT/FR2009/051118 patent/WO2009150388A1/fr active Application Filing
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2010
- 2010-12-08 CR CR11832A patent/CR11832A/es unknown
- 2010-12-08 DO DO2010000380A patent/DOP2010000380A/es unknown
- 2010-12-09 IL IL209902A patent/IL209902A/en active IP Right Grant
- 2010-12-09 SV SV2010003755A patent/SV2010003755A/es unknown
- 2010-12-10 EC EC2010010672A patent/ECSP10010672A/es unknown
- 2010-12-10 NI NI201000215A patent/NI201000215A/es unknown
- 2010-12-13 CO CO10156029A patent/CO6280535A2/es active IP Right Grant
- 2010-12-13 CL CL2010001429A patent/CL2010001429A1/es unknown
- 2010-12-13 US US12/966,413 patent/US8193190B2/en active Active
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2011
- 2011-01-13 MA MA33517A patent/MA32474B1/fr unknown
- 2011-11-29 HK HK11112930.5A patent/HK1158631A1/xx not_active IP Right Cessation
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2012
- 2012-04-02 HR HR20120290T patent/HRP20120290T1/hr unknown
- 2012-04-04 CY CY20121100339T patent/CY1112610T1/el unknown
- 2012-05-17 US US13/473,885 patent/US8519143B2/en active Active
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2013
- 2013-06-04 DO DO2013000124A patent/DOP2013000124A/es unknown
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