JP2015506348A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015506348A5 JP2015506348A5 JP2014548913A JP2014548913A JP2015506348A5 JP 2015506348 A5 JP2015506348 A5 JP 2015506348A5 JP 2014548913 A JP2014548913 A JP 2014548913A JP 2014548913 A JP2014548913 A JP 2014548913A JP 2015506348 A5 JP2015506348 A5 JP 2015506348A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- nhr
- aryl
- salt
- nhc
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- -1 1,2,3,4-tetrahydronaphthyl Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 16
- 230000009385 viral infection Effects 0.000 claims description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 241000711902 Pneumovirus Species 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 108700002314 gontivimab Proteins 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229960001521 motavizumab Drugs 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229960000402 palivizumab Drugs 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 5
- 229960000329 ribavirin Drugs 0.000 claims description 5
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- BLUJRJMLDHEMRX-UHFFFAOYSA-N 2-[[2-hydroxy-5-[(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1N=Cc1ccc(O)c(c1)C(c1ccc(O)cc1)c1cc(C=Nn2nnnc2C)ccc1O BLUJRJMLDHEMRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- KSHJXDWYTZJUEI-UHFFFAOYSA-N 1-cyclopropyl-3-[[1-(4-hydroxybutyl)benzimidazol-2-yl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound N=1C2=CC=CC=C2N(CCCCO)C=1CN(C1=O)C2=CN=CC=C2N1C1CC1 KSHJXDWYTZJUEI-UHFFFAOYSA-N 0.000 claims 1
- 241000711904 Pneumoviridae Species 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 Cc1c[n]2nc(C(CCCC3)N3C(c3c(C(F)(F)F)cccc3)=O)cc2nc1N(C[C@]1*)C[C@@]1O Chemical compound Cc1c[n]2nc(C(CCCC3)N3C(c3c(C(F)(F)F)cccc3)=O)cc2nc1N(C[C@]1*)C[C@@]1O 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- LJMJHHZSIVNEMW-UXPWSPDFSA-N CC(C)[n]1ncc(Cl)c1C(N(CCCC1)[C@@H]1c1n[n](cc(C)c(N(C[C@H]2C#N)C[C@@H]2O)n2)c2c1)=O Chemical compound CC(C)[n]1ncc(Cl)c1C(N(CCCC1)[C@@H]1c1n[n](cc(C)c(N(C[C@H]2C#N)C[C@@H]2O)n2)c2c1)=O LJMJHHZSIVNEMW-UXPWSPDFSA-N 0.000 description 2
- OKQLFHTVGNRMND-HOJAQTOUSA-N Cc1c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)nccc1 Chemical compound Cc1c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)nccc1 OKQLFHTVGNRMND-HOJAQTOUSA-N 0.000 description 2
- VZMDKBIHWMCMLN-BUJZBAMKSA-N Cc1c[n]2nc(C(CCCC3)N3C(c(cc(cc3)F)c3Cl)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc(C(CCCC3)N3C(c(cc(cc3)F)c3Cl)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O VZMDKBIHWMCMLN-BUJZBAMKSA-N 0.000 description 2
- IPAMMMZKTPRJIG-ICTDUYRTSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c(cccc3)c3-c3ccccc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c(cccc3)c3-c3ccccc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O IPAMMMZKTPRJIG-ICTDUYRTSA-N 0.000 description 2
- RRNSJMLVNQMNPL-WTNAPCKOSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3c[s]c4c3CCCC4)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3c[s]c4c3CCCC4)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O RRNSJMLVNQMNPL-WTNAPCKOSA-N 0.000 description 2
- ZGUFLPWZJOKDCS-NEWSRXKRSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3c[s]cc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3c[s]cc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O ZGUFLPWZJOKDCS-NEWSRXKRSA-N 0.000 description 2
- VZKFSGYKBYXYOF-XGRCMKMKSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(OC)ccc3Cl)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(OC)ccc3Cl)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O VZKFSGYKBYXYOF-XGRCMKMKSA-N 0.000 description 2
- HYZRHOCPKOUTIS-OIBXWCBGSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3cccc4c3cc[n]4C)=O)cc2nc1N(C[C@H]1N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3cccc4c3cc[n]4C)=O)cc2nc1N(C[C@H]1N)C[C@@H]1O HYZRHOCPKOUTIS-OIBXWCBGSA-N 0.000 description 2
- TUKONYDEGAMPCN-AYBZRNKSSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3ccn[n]3CC(F)(F)F)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3ccn[n]3CC(F)(F)F)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O TUKONYDEGAMPCN-AYBZRNKSSA-N 0.000 description 2
- WNLZNPSVISTKRX-NJAFHUGGSA-N Cc1n[n](C)c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c1Cl Chemical compound Cc1n[n](C)c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c1Cl WNLZNPSVISTKRX-NJAFHUGGSA-N 0.000 description 2
- BBWFJUUKVGEWCJ-UHBFCERESA-N CC(C(CCCC1)N1C(c1cc(CCC=C2)c2cc1OC)=O)/C=C(/C(CC(C(C)=C1)N(CC2)CC2N)=C)\N1N Chemical compound CC(C(CCCC1)N1C(c1cc(CCC=C2)c2cc1OC)=O)/C=C(/C(CC(C(C)=C1)N(CC2)CC2N)=C)\N1N BBWFJUUKVGEWCJ-UHBFCERESA-N 0.000 description 1
- NZVMRLZBENHKIT-UHFFFAOYSA-N CC1=CN2NC(C(CCCC3)N3C(c3cc(Cl)cc(Cl)n3)O)C=C2N=C1N(CC1)CC1N Chemical compound CC1=CN2NC(C(CCCC3)N3C(c3cc(Cl)cc(Cl)n3)O)C=C2N=C1N(CC1)CC1N NZVMRLZBENHKIT-UHFFFAOYSA-N 0.000 description 1
- ZUHIBVFHQMDMSE-CQLNOVPUSA-N C[C@H](CN(C1)c2nc3cc([C@H](CCCC4)N4C(c(cc(CCC4)c4c4)c4OC)=O)n[n]3cc2C)[C@H]1O Chemical compound C[C@H](CN(C1)c2nc3cc([C@H](CCCC4)N4C(c(cc(CCC4)c4c4)c4OC)=O)n[n]3cc2C)[C@H]1O ZUHIBVFHQMDMSE-CQLNOVPUSA-N 0.000 description 1
- DQXXQOYYRHQWOT-PBXQCXKZSA-N C[C@H](CN(C1)c2nc3cc([C@H](CCCC4)N4C(c4nccc(-c5ccccc5)c4)=O)n[n]3cc2C)[C@H]1O Chemical compound C[C@H](CN(C1)c2nc3cc([C@H](CCCC4)N4C(c4nccc(-c5ccccc5)c4)=O)n[n]3cc2C)[C@H]1O DQXXQOYYRHQWOT-PBXQCXKZSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BDCMMTOBVDRGBX-UXPWSPDFSA-N Cc(ccc(F)c1C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c1F Chemical compound Cc(ccc(F)c1C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c1F BDCMMTOBVDRGBX-UXPWSPDFSA-N 0.000 description 1
- SFAZXGULNIOTOJ-PUHATCMVSA-N Cc1c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)[nH]c2c(C)ccc(C)c12 Chemical compound Cc1c(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)[nH]c2c(C)ccc(C)c12 SFAZXGULNIOTOJ-PUHATCMVSA-N 0.000 description 1
- DZCASUFRISLUAW-UHFFFAOYSA-N Cc1c[n]2nc(C(CCCC3)N3C(C3=CCCC4=C3CNN4C)O)cc2nc1N(CC1)CC1NC Chemical compound Cc1c[n]2nc(C(CCCC3)N3C(C3=CCCC4=C3CNN4C)O)cc2nc1N(CC1)CC1NC DZCASUFRISLUAW-UHFFFAOYSA-N 0.000 description 1
- GEXFZAQAQKDOFK-UHFFFAOYSA-N Cc1c[n]2nc(C(CCCC3)N3C(c(cc3)ncc3Cl)=O)cc2nc1N(CC1)CC1NC Chemical compound Cc1c[n]2nc(C(CCCC3)N3C(c(cc3)ncc3Cl)=O)cc2nc1N(CC1)CC1NC GEXFZAQAQKDOFK-UHFFFAOYSA-N 0.000 description 1
- GXUXOOMUDORFPZ-UHFFFAOYSA-N Cc1c[n]2nc(C(CCCC3)N3C(c3c[s]c(cc4)c3cc4Br)O)cc2nc1N(CC1)CC1N Chemical compound Cc1c[n]2nc(C(CCCC3)N3C(c3c[s]c(cc4)c3cc4Br)O)cc2nc1N(CC1)CC1N GXUXOOMUDORFPZ-UHFFFAOYSA-N 0.000 description 1
- UMEMAYVFWWNFBR-QLEIAVNASA-N Cc1c[n]2nc([C@H](CCCC3)N3C(C3C=CC4=CC=CCC4C3)=O)cc2nc1N(CC1)CC1N Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(C3C=CC4=CC=CCC4C3)=O)cc2nc1N(CC1)CC1N UMEMAYVFWWNFBR-QLEIAVNASA-N 0.000 description 1
- CVXOOYSXUGCKIK-XGRCMKMKSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c(c(F)c3)ccc3OC)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c(c(F)c3)ccc3OC)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O CVXOOYSXUGCKIK-XGRCMKMKSA-N 0.000 description 1
- OJLTTZSVHLCMAL-RZFJZAQRSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c(cc3)ncc3-c3ccccc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c(cc3)ncc3-c3ccccc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O OJLTTZSVHLCMAL-RZFJZAQRSA-N 0.000 description 1
- LTLAPWAEPHATSO-LEOXJPRUSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c(ccc3ccc4)nc3c4F)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c(ccc3ccc4)nc3c4F)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O LTLAPWAEPHATSO-LEOXJPRUSA-N 0.000 description 1
- LWQANBKGJRSQOD-XGRCMKMKSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(Cl)ccc3NS(C)(=O)=O)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(Cl)ccc3NS(C)(=O)=O)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O LWQANBKGJRSQOD-XGRCMKMKSA-N 0.000 description 1
- RCEBYRIHHSYWMN-WTNAPCKOSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(F)cc4c3OCOC4)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3cc(F)cc4c3OCOC4)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O RCEBYRIHHSYWMN-WTNAPCKOSA-N 0.000 description 1
- MRXWDPJDCLGSHP-AGHHOFFYSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3cccc4ccn[n]34)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3cccc4ccn[n]34)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O MRXWDPJDCLGSHP-AGHHOFFYSA-N 0.000 description 1
- FSHGZALLVVXDGZ-LEOXJPRUSA-N Cc1c[n]2nc([C@H](CCCC3)N3C(c3nc4ccncc4cc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O Chemical compound Cc1c[n]2nc([C@H](CCCC3)N3C(c3nc4ccncc4cc3)=O)cc2nc1N(C[C@H]1C#N)C[C@@H]1O FSHGZALLVVXDGZ-LEOXJPRUSA-N 0.000 description 1
- DZMBFEFYCVIZBP-UHFFFAOYSA-N Cc1ccc(C(N(CCCC2)C2c2n[n](cc(C)c(N3CCCC3)n3)c3c2)O)c(OC)c1 Chemical compound Cc1ccc(C(N(CCCC2)C2c2n[n](cc(C)c(N3CCCC3)n3)c3c2)O)c(OC)c1 DZMBFEFYCVIZBP-UHFFFAOYSA-N 0.000 description 1
- MGKPNWCWSKJHES-WTNAPCKOSA-N Cc1ccc(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c(Cl)c1 Chemical compound Cc1ccc(C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C[C@@H]3O)n3)c3c2)=O)c(Cl)c1 MGKPNWCWSKJHES-WTNAPCKOSA-N 0.000 description 1
- NXXYUNPTIPXYSD-GCJKJVERSA-N Cc1n[o]c(-c(cccc2)c2C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C=C3O)n3)c3c2)=O)n1 Chemical compound Cc1n[o]c(-c(cccc2)c2C(N(CCCC2)[C@@H]2c2n[n](cc(C)c(N(C[C@H]3C#N)C=C3O)n3)c3c2)=O)n1 NXXYUNPTIPXYSD-GCJKJVERSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161579625P | 2011-12-22 | 2011-12-22 | |
| US61/579,625 | 2011-12-22 | ||
| US201261618510P | 2012-03-30 | 2012-03-30 | |
| US61/618,510 | 2012-03-30 | ||
| PCT/US2012/071065 WO2013096681A1 (en) | 2011-12-22 | 2012-12-20 | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016224719A Division JP2017036336A (ja) | 2011-12-22 | 2016-11-18 | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015506348A JP2015506348A (ja) | 2015-03-02 |
| JP2015506348A5 true JP2015506348A5 (OSRAM) | 2016-02-12 |
| JP6122868B2 JP6122868B2 (ja) | 2017-04-26 |
Family
ID=47557523
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014548913A Active JP6122868B2 (ja) | 2011-12-22 | 2012-12-20 | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
| JP2016224719A Withdrawn JP2017036336A (ja) | 2011-12-22 | 2016-11-18 | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016224719A Withdrawn JP2017036336A (ja) | 2011-12-22 | 2016-11-18 | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US8946238B2 (OSRAM) |
| EP (1) | EP2794611B1 (OSRAM) |
| JP (2) | JP6122868B2 (OSRAM) |
| AU (1) | AU2012358805B2 (OSRAM) |
| CA (1) | CA2858096C (OSRAM) |
| ES (1) | ES2647486T3 (OSRAM) |
| PT (1) | PT2794611T (OSRAM) |
| WO (1) | WO2013096681A1 (OSRAM) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2585467T3 (en) | 2010-06-24 | 2016-06-13 | Gilead Sciences Inc | PYRAZOLO [1,5-A] PYRIMIDINES AND TRIAZINES AS ANTIVIRAL AGENTS |
| JP6122868B2 (ja) | 2011-12-22 | 2017-04-26 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
| SI2838900T1 (sl) | 2012-04-17 | 2019-10-30 | Gilead Sciences Inc | Spojine in postopki za protivirusno zdravljenje |
| CN114716426A (zh) | 2013-08-21 | 2022-07-08 | 詹森生物制药有限公司 | 抗病毒化合物 |
| WO2016022464A1 (en) * | 2014-08-05 | 2016-02-11 | Alios Biopharma, Inc. | Combination therapy for treating a paramyxovirus |
| EP3230288B1 (en) * | 2014-12-08 | 2018-11-21 | Janssen Sciences Ireland UC | Piperidine substituted tricyclic pyrazolo[1,5-a]pyrimidine derivatives with inhibitory activity on the replication of the respiratory syncytial virus (rsv) |
| MX368162B (es) | 2014-12-08 | 2019-09-20 | Janssen Sciences Ireland Uc | Derivados de pirazolo[1,5-a]pirimidina sustituida con piperidina con actividad inhibidora sobre la replicacion del virus sincicial respiratorio (vsr). |
| SG11201705069YA (en) | 2014-12-26 | 2017-07-28 | Univ Emory | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| MA41614A (fr) | 2015-02-25 | 2018-01-02 | Alios Biopharma Inc | Composés antiviraux |
| JP2018076234A (ja) * | 2015-03-16 | 2018-05-17 | 大正製薬株式会社 | ピラゾロ［１，５−ａ］ピリミジン化合物 |
| CN108200760B (zh) | 2015-07-22 | 2022-04-01 | 英安塔制药有限公司 | 作为rsv抑制剂的苯并二氮杂䓬衍生物 |
| EP3402799B1 (en) | 2016-01-15 | 2022-05-04 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as rsv inhibitors |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EP4491236A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| JP6957518B2 (ja) * | 2016-05-20 | 2021-11-02 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 感染症の治療のための酸素、硫黄および窒素リンカーを有する新規ピラジン化合物 |
| IL314380A (en) | 2016-10-06 | 2024-09-01 | Orbus Therapeutics Inc | Preparations for administration of aflornithine |
| EP3582784B1 (en) | 2017-02-16 | 2022-06-08 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of benzodiazepine derivatives |
| CN118440096A (zh) | 2017-06-20 | 2024-08-06 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| WO2019006295A1 (en) | 2017-06-30 | 2019-01-03 | Enanta Pharmaceuticals, Inc. | HETEROCYCLIC COMPOUNDS AS RSV INHIBITORS |
| JP7065951B2 (ja) | 2017-09-22 | 2022-05-12 | ジュビラント エピパッド エルエルシー | Ｐａｄ阻害剤としての複素環式化合物 |
| AU2018339068B2 (en) | 2017-09-29 | 2022-12-15 | Enanta Pharmaceuticals, Inc. | Combination pharmaceutical agents as RSV inhibitors |
| WO2019077631A1 (en) | 2017-10-18 | 2019-04-25 | Jubilant Biosys Limited | IMIDAZO-PYRIDINE COMPOUNDS FOR USE AS PAD INHIBITORS |
| EP3707135A1 (en) | 2017-11-06 | 2020-09-16 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| MX394621B (es) | 2017-11-13 | 2025-03-24 | Enanta Pharm Inc | Procesos para la resolucion de los derivados de la benzodiazepina-2-ona y de la benzoazepin-2-ona |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as prmt5 inhibitors |
| PL3706762T3 (pl) | 2017-12-07 | 2025-02-10 | Emory University | N4-hydroksycytydyna i pochodne oraz związane z nimi zastosowania przeciwwirusowe |
| US11491157B2 (en) | 2018-01-31 | 2022-11-08 | Janssen Sciences Ireland Unlimited Company Co Cork, IE | Cycloalkyl substituted pyrazolopyrimidines having activity against RSV |
| WO2019175897A1 (en) | 2018-03-13 | 2019-09-19 | Jubilant Biosys Limited | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
| WO2019206828A1 (en) | 2018-04-23 | 2019-10-31 | Janssen Sciences Ireland Unlimited Company | Heteroaromatic compounds having activity against rsv |
| MX2021006138A (es) * | 2018-11-26 | 2021-06-23 | Janssen Sciences Ireland Unlimited Co | Otros compuestos heteroaromaticos que tienen actividad contra el vrs. |
| US20230069963A1 (en) | 2018-12-27 | 2023-03-09 | Taisho Pharmaceutical Co., Ltd. | Pyrazolo[1,5-a]pyrimidine macrocyclic compound |
| PH12021552201A1 (en) | 2019-03-18 | 2022-05-30 | Enanta Pharm Inc | Benzodiazepine derivatives as rsv inhibitors |
| US11505558B1 (en) | 2019-10-04 | 2022-11-22 | Enanta Pharmaceuticals, Inc. | Antiviral heterocyclic compounds |
| MX2022003984A (es) | 2019-10-04 | 2022-07-27 | Enanta Pharm Inc | Compuestos heterociclicos antivirales. |
| UY39032A (es) | 2020-01-24 | 2021-07-30 | Enanta Pharm Inc | Compuestos heterocíclicos como agentes antivirales |
| US11534439B2 (en) | 2020-07-07 | 2022-12-27 | Enanta Pharmaceuticals, Inc. | Dihydroquinoxaline and dihydropyridopyrazine derivatives as RSV inhibitors |
| US11945824B2 (en) | 2020-10-19 | 2024-04-02 | Enanta Pharmaceuticals, Inc. | Heterocyclic compounds as anti-viral agents |
| US11945830B2 (en) | 2021-02-26 | 2024-04-02 | Enanta Pharmaceuticals, Inc. | Antiviral heterocyclic compounds |
| JPWO2022270628A1 (OSRAM) * | 2021-06-25 | 2022-12-29 | ||
| AR129003A1 (es) | 2022-04-07 | 2024-07-03 | Enanta Pharm Inc | Compuestos heterocíclicos antivirales |
| US12162857B2 (en) | 2022-04-27 | 2024-12-10 | Enanta Pharmaceuticals, Inc. | Antiviral compounds |
| CN117658980A (zh) * | 2022-09-08 | 2024-03-08 | 郑州同源康医药有限公司 | 双环类prmt5抑制剂 |
| CN115710200B (zh) * | 2022-11-21 | 2024-08-09 | 重庆医科大学 | 苯甲酰氟类化合物、苯甲酸类化合物及其制备方法 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5543413A (en) * | 1994-02-25 | 1996-08-06 | Regents Of The University Of Michigan | Heterocyclic thioamides and related analogs as antiviral agents with a unique mode of action |
| US6342501B1 (en) * | 1994-02-25 | 2002-01-29 | The Regents Of The University Of Michigan | Pyrrolo[2,3-d] pyrimidines as antiviral agents |
| BR9508178A (pt) | 1994-06-29 | 1997-11-18 | Smithkline Beecham Corp | Antagonistas de receptor de vitronectina |
| CA2321153A1 (en) | 1998-02-17 | 1999-08-19 | Timothy D. Cushing | Anti-viral pyrimidine derivatives |
| TWI225488B (en) | 1999-12-21 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivatives of homopiperidinyl substituted benzimidazole analogues |
| BR0308391A (pt) | 2002-03-13 | 2005-01-11 | Pharmacia & Upjohn Co Llc | Derivados de pirazolo(1,5-a)piridina como moduladores neurotransmissores |
| ATE365740T1 (de) | 2002-05-10 | 2007-07-15 | Smithkline Beecham Corp | Substituierte pyrazolopyrimidine |
| CA2487211C (en) * | 2002-06-04 | 2010-09-14 | Neogenesis Pharmaceuticals, Inc. | Pyrazolo(1,5a) pyrimidine compounds as antiviral agents |
| DE10247271A1 (de) | 2002-10-10 | 2004-08-26 | Grünenthal GmbH | Substituierte C-Imidazo[1,2-a]pyridin-3-yle |
| ES2360222T3 (es) | 2003-12-24 | 2011-06-02 | Biota Scientific Management Pty. Ltd. | Agentes policíclicos para el tratamiento de infecciones respiratorias por virus sincicial. |
| SG133452A1 (en) | 2005-12-30 | 2007-07-30 | Novartis Ag | Peptide deformylase inhibitors for treatment of mycobacterial and other parasitic diseases |
| WO2008070447A2 (en) | 2006-11-21 | 2008-06-12 | Smithkline Beecham Corporation | Anti-viral compounds |
| EP2229459B1 (en) | 2007-12-13 | 2014-08-27 | Alnylam Pharmaceuticals, Inc. | Methods and compositions for prevention or treatment of RSV infection |
| EP2234487A4 (en) | 2007-12-19 | 2011-09-07 | Scripps Research Inst | ANILIDES AND ANALOGUES AS INHIBITORS OF RHO KINASE |
| US20110009429A1 (en) | 2008-02-26 | 2011-01-13 | Paul Oakley | Heterocyclic compounds as inhibitors of cxcr2 |
| US8461163B2 (en) * | 2008-03-31 | 2013-06-11 | Takeda Pharmaceutical Company Limited | Substituted N-(pyrazolo[1,5-a]pyrimidin-5-yl)amides as inhibitors of apoptosis signal-regulating kinase 1 |
| EP2282742A1 (en) | 2008-04-09 | 2011-02-16 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| US20110275673A1 (en) | 2008-09-19 | 2011-11-10 | Yibin Xiang | Inhibitors of sphingosine kinase 1 |
| EP2182081B1 (de) | 2008-10-29 | 2014-01-22 | Neue Materialien Bayreuth GmbH | Verfahren zur thermischen Behandlung eines beschichteten Stahlblechkörpers |
| CN104163816A (zh) | 2008-12-03 | 2014-11-26 | 普雷西迪奥制药公司 | Hcv ns5a的抑制剂 |
| EP2379524A1 (en) | 2008-12-18 | 2011-10-26 | Boehringer Ingelheim International GmbH | Serotonin 5-ht2b receptor inhibitors |
| MX2011006332A (es) | 2008-12-23 | 2011-06-27 | Abbott Lab | Compuestos antivirales. |
| TWI438200B (zh) | 2009-02-17 | 2014-05-21 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| KR20130130875A (ko) | 2009-02-27 | 2013-12-02 | 이난타 파마슈티칼스, 인코포레이티드 | Ｃ형 간염 바이러스 억제제 |
| EP2404902A1 (en) | 2009-03-05 | 2012-01-11 | Shionogi&Co., Ltd. | Piperidine and pyrrolidine derivatives having npy y5 receptor antagonism |
| DK2368890T3 (da) | 2009-06-11 | 2013-07-22 | Abbvie Bahamas Ltd | Hepatitis C-virusinhibitorer |
| WO2010148006A1 (en) | 2009-06-16 | 2010-12-23 | Enanta Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| WO2011015658A1 (en) | 2009-08-07 | 2011-02-10 | Tibotec Pharmaceuticals | Bis-benzimidazole derivatives as hepatitis c virus inhibitors |
| US20110274648A1 (en) | 2009-11-11 | 2011-11-10 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| ES2475970T3 (es) * | 2009-12-23 | 2014-07-11 | Katholieke Universiteit Leuven | Novedosos compuestos antivirales |
| WO2011099832A2 (en) | 2010-02-12 | 2011-08-18 | Crystalgenomics, Inc. | Novel benzimidazole compound, preparation method thereof and pharmaceutical composition comprising the same |
| CA2800509A1 (en) | 2010-05-24 | 2011-12-01 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| DK2585467T3 (en) | 2010-06-24 | 2016-06-13 | Gilead Sciences Inc | PYRAZOLO [1,5-A] PYRIMIDINES AND TRIAZINES AS ANTIVIRAL AGENTS |
| UA111163C2 (uk) | 2010-07-22 | 2016-04-11 | Гайлід Сайєнсіз, Інк. | Способи й сполуки для лікування вірусних інфекцій paramyxoviridae |
| JP6122868B2 (ja) | 2011-12-22 | 2017-04-26 | ギリアード サイエンシーズ， インコーポレイテッド | 抗ウイルス剤としてのピラゾロ［１，５−ａ］ピリミジン |
| SI2838900T1 (sl) | 2012-04-17 | 2019-10-30 | Gilead Sciences Inc | Spojine in postopki za protivirusno zdravljenje |
-
2012
- 2012-12-20 JP JP2014548913A patent/JP6122868B2/ja active Active
- 2012-12-20 US US13/722,962 patent/US8946238B2/en active Active
- 2012-12-20 AU AU2012358805A patent/AU2012358805B2/en active Active
- 2012-12-20 WO PCT/US2012/071065 patent/WO2013096681A1/en not_active Ceased
- 2012-12-20 EP EP12814092.8A patent/EP2794611B1/en active Active
- 2012-12-20 CA CA2858096A patent/CA2858096C/en active Active
- 2012-12-20 ES ES12814092.8T patent/ES2647486T3/es active Active
- 2012-12-20 PT PT128140928T patent/PT2794611T/pt unknown
-
2014
- 2014-12-10 US US14/566,340 patent/US9278975B2/en active Active
-
2016
- 2016-01-19 US US15/000,821 patent/US20160235748A1/en not_active Abandoned
- 2016-11-18 JP JP2016224719A patent/JP2017036336A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2015506348A5 (OSRAM) | ||
| KR101756050B1 (ko) | 톨 유사 수용체 조정제 화합물 | |
| JP2013512903A5 (OSRAM) | ||
| AU2013345107B2 (en) | Heteroaromatic compounds as PI3 kinase modulators and methods of use | |
| KR20190040338A (ko) | 톨 유사 수용체 조정제 화합물 | |
| JP2013542261A5 (OSRAM) | ||
| JP2010523522A5 (OSRAM) | ||
| JP2019537570A5 (OSRAM) | ||
| JP2011529918A5 (OSRAM) | ||
| CA2870024A1 (en) | Compounds and methods for antiviral treatment | |
| JP2017523169A5 (OSRAM) | ||
| JP2014500295A5 (OSRAM) | ||
| RU2016141569A (ru) | Комбинации | |
| JP2014532716A5 (OSRAM) | ||
| JP2011516428A5 (OSRAM) | ||
| JP2010513523A5 (OSRAM) | ||
| JP2013529196A5 (OSRAM) | ||
| JP2016515561A5 (OSRAM) | ||
| JP2011507881A5 (OSRAM) | ||
| JP2019511542A (ja) | カプシド集合阻害剤を含む組み合わせ及び方法 | |
| JP2012524089A5 (OSRAM) | ||
| JP2019505529A5 (OSRAM) | ||
| JP2017525699A5 (OSRAM) | ||
| RU2016150326A (ru) | Производные изоиндолина для применения в лечении вирусной инфекции | |
| JP2008517913A5 (OSRAM) |