JP2015506348A5 - - Google Patents
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- 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
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- 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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2794611B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6122868B2 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2012358805B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2858096C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2647486T3 (cg-RX-API-DMAC7.html) |
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