JP2018536681A5 - - Google Patents
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- JP2018536681A5 JP2018536681A5 JP2018529614A JP2018529614A JP2018536681A5 JP 2018536681 A5 JP2018536681 A5 JP 2018536681A5 JP 2018529614 A JP2018529614 A JP 2018529614A JP 2018529614 A JP2018529614 A JP 2018529614A JP 2018536681 A5 JP2018536681 A5 JP 2018536681A5
- Authority
- JP
- Japan
- Prior art keywords
- membered
- alkylene
- independently
- ring
- alkyl
- 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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- 125000002947 alkylene group Chemical group 0.000 claims description 123
- 125000000623 heterocyclic group Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- -1 C 2-6 alkini Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 230000009385 viral infection Effects 0.000 claims description 12
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 10
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 241000712461 unidentified influenza virus Species 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 4
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims description 4
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 239000002207 metabolite Substances 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 4
- 229940002612 prodrug Drugs 0.000 claims description 4
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- KZIMLUFVKJLCCH-UHFFFAOYSA-N 5-[2-(1h-imidazol-5-yl)ethylamino]-5-oxopentanoic acid Chemical compound OC(=O)CCCC(=O)NCCC1=CNC=N1 KZIMLUFVKJLCCH-UHFFFAOYSA-N 0.000 claims description 2
- 229940124873 Influenza virus vaccine Drugs 0.000 claims description 2
- QNRRHYPPQFELSF-CNYIRLTGSA-N Laninamivir Chemical compound OC[C@@H](O)[C@@H](OC)[C@@H]1OC(C(O)=O)=C[C@H](N=C(N)N)[C@H]1NC(C)=O QNRRHYPPQFELSF-CNYIRLTGSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003805 amantadine Drugs 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 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
- ZCGNOVWYSGBHAU-UHFFFAOYSA-N favipiravir Chemical compound NC(=O)C1=NC(F)=CNC1=O ZCGNOVWYSGBHAU-UHFFFAOYSA-N 0.000 claims description 2
- 229950008454 favipiravir Drugs 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 206010022000 influenza Diseases 0.000 claims description 2
- 229960003971 influenza vaccine Drugs 0.000 claims description 2
- 229950004244 laninamivir Drugs 0.000 claims description 2
- 229950005327 laninamivir octanoate hydrate Drugs 0.000 claims description 2
- UKTIJASCFRNWCB-RMIBSVFLSA-N laninamivir octanoate hydrate Chemical compound CCCCCCCC(=O)OC[C@@H](O)[C@@H](OC)[C@@H]1OC(C(O)=O)=C[C@H](N=C(N)N)[C@H]1NC(C)=O UKTIJASCFRNWCB-RMIBSVFLSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims description 2
- 229960003752 oseltamivir Drugs 0.000 claims description 2
- XRQDFNLINLXZLB-CKIKVBCHSA-N peramivir Chemical compound CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N XRQDFNLINLXZLB-CKIKVBCHSA-N 0.000 claims description 2
- 229960001084 peramivir Drugs 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- 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 2
- 229960000888 rimantadine Drugs 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- KCFYEAOKVJSACF-UHFFFAOYSA-N umifenovir Chemical compound CN1C2=CC(Br)=C(O)C(CN(C)C)=C2C(C(=O)OCC)=C1CSC1=CC=CC=C1 KCFYEAOKVJSACF-UHFFFAOYSA-N 0.000 claims description 2
- 229960004626 umifenovir Drugs 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 229960001028 zanamivir Drugs 0.000 claims description 2
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- IYXLGNJQZFZRFP-LJQANCHMSA-N CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccccc2)c1 Chemical compound CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccccc2)c1 IYXLGNJQZFZRFP-LJQANCHMSA-N 0.000 description 1
- VUFDMXAKBCFELU-QGZVFWFLSA-N CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccccc2)c1F Chemical compound CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccccc2)c1F VUFDMXAKBCFELU-QGZVFWFLSA-N 0.000 description 1
- YNPQZXDXIGHAED-QGZVFWFLSA-N CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2ccc[o]2)c1 Chemical compound CC(C)(C)[C@@H](CC(O)=O)Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2ccc[o]2)c1 YNPQZXDXIGHAED-QGZVFWFLSA-N 0.000 description 1
- AXEFCXUVZHWHGX-PGRUHTEZSA-N CC(C)[n](cc1)c2c1c(N[C@@H](C(CCC1)CC1C1)[C@H]1C(O)=O)nc(-c(c1c3)c[nH]c1ncc3F)n2 Chemical compound CC(C)[n](cc1)c2c1c(N[C@@H](C(CCC1)CC1C1)[C@H]1C(O)=O)nc(-c(c1c3)c[nH]c1ncc3F)n2 AXEFCXUVZHWHGX-PGRUHTEZSA-N 0.000 description 1
- QGXBAXVERMIPRL-CLONCEMUSA-N CC(C)[n](cc1)c2c1c(N[C@@H](C1CCC3CC1)[C@H]3C(O)=O)nc(-c1c[nH]c3nc(F)ccc13)n2 Chemical compound CC(C)[n](cc1)c2c1c(N[C@@H](C1CCC3CC1)[C@H]3C(O)=O)nc(-c1c[nH]c3nc(F)ccc13)n2 QGXBAXVERMIPRL-CLONCEMUSA-N 0.000 description 1
- BOZSJEUVUOGAPD-QGZVFWFLSA-N CC(C)[n](cc1)c2c1c(N[C@H](CC(O)=O)C(C)(C)C)nc(-c1c[nH]c(nc3)c1cc3F)n2 Chemical compound CC(C)[n](cc1)c2c1c(N[C@H](CC(O)=O)C(C)(C)C)nc(-c1c[nH]c(nc3)c1cc3F)n2 BOZSJEUVUOGAPD-QGZVFWFLSA-N 0.000 description 1
- QCCGXNMHWWZGIT-UHFFFAOYSA-N Cc(nc(c1c2)[nH]cc1-c1nc(-c3ccccc3)cc(NC(C3CCC4CC3)C4C(O)=O)n1)c2F Chemical compound Cc(nc(c1c2)[nH]cc1-c1nc(-c3ccccc3)cc(NC(C3CCC4CC3)C4C(O)=O)n1)c2F QCCGXNMHWWZGIT-UHFFFAOYSA-N 0.000 description 1
- CALZYKFFWFNLPQ-MQBCKMQZSA-N Fc(cc1)nc2c1c(-c1nc(-c3ccc[o]3)cc(N[C@H]3C(CC4)CCC4C3)n1)c[nH]2 Chemical compound Fc(cc1)nc2c1c(-c1nc(-c3ccc[o]3)cc(N[C@H]3C(CC4)CCC4C3)n1)c[nH]2 CALZYKFFWFNLPQ-MQBCKMQZSA-N 0.000 description 1
- TWOYUNLMJFFZHT-UHFFFAOYSA-N Fc1cc(c(-c2nc(C#Cc3ccccc3)cc(NCC3C(CC4)CCC4C3)n2)c[nH]2)c2nc1 Chemical compound Fc1cc(c(-c2nc(C#Cc3ccccc3)cc(NCC3C(CC4)CCC4C3)n2)c[nH]2)c2nc1 TWOYUNLMJFFZHT-UHFFFAOYSA-N 0.000 description 1
- KKZHFHUKMNBQBU-UHFFFAOYSA-N Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2ccc([N+]([O-])=O)[o]2)c1 Chemical compound Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2ccc([N+]([O-])=O)[o]2)c1 KKZHFHUKMNBQBU-UHFFFAOYSA-N 0.000 description 1
- NDEQSCVITBUECF-UHFFFAOYSA-N OC(C(C1CCC2CC1)C2Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccn[o]2)c1F)=O Chemical compound OC(C(C1CCC2CC1)C2Nc1nc(-c(c2c3)c[nH]c2ncc3F)nc(-c2ccn[o]2)c1F)=O NDEQSCVITBUECF-UHFFFAOYSA-N 0.000 description 1
- SMTZKOKXSOOYNG-UHFFFAOYSA-N OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2cc(-c3ccccc3)c[o]2)c1)=O Chemical compound OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2cc(-c3ccccc3)c[o]2)c1)=O SMTZKOKXSOOYNG-UHFFFAOYSA-N 0.000 description 1
- CWESJCUHNCHWIW-UHFFFAOYSA-N OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2cc(CCCC3)c3[o]2)c1)=O Chemical compound OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c(nc3)c2cc3F)nc(-c2cc(CCCC3)c3[o]2)c1)=O CWESJCUHNCHWIW-UHFFFAOYSA-N 0.000 description 1
- QYCUEMLOXWGPQO-UHFFFAOYSA-N OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c3nc(F)ccc23)nc(-c2ccc[o]2)c1F)=O Chemical compound OC(C(C1CCC2CC1)C2Nc1nc(-c2c[nH]c3nc(F)ccc23)nc(-c2ccc[o]2)c1F)=O QYCUEMLOXWGPQO-UHFFFAOYSA-N 0.000 description 1
- ZIPJJDPWVGOPDF-JKUSDIHRSA-N OC([C@@H](C1CCC2CC1)[C@H]2Nc1nc(-c2c[nH]c3c2ccc(F)n3)nc(-c2ccccc2)c1)=O Chemical compound OC([C@@H](C1CCC2CC1)[C@H]2Nc1nc(-c2c[nH]c3c2ccc(F)n3)nc(-c2ccccc2)c1)=O ZIPJJDPWVGOPDF-JKUSDIHRSA-N 0.000 description 1
- PNKGHXVHKCJNBW-KAVNDROISA-N OC([C@H]1C(CC2)CCC2C1)=O Chemical compound OC([C@H]1C(CC2)CCC2C1)=O PNKGHXVHKCJNBW-KAVNDROISA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510908329 | 2015-12-09 | ||
| CN201510908329.2 | 2015-12-09 | ||
| PCT/CN2016/109079 WO2017097234A1 (en) | 2015-12-09 | 2016-12-08 | Inhibitors of influenza virus replication, application methods and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018536681A JP2018536681A (ja) | 2018-12-13 |
| JP2018536681A5 true JP2018536681A5 (OSRAM) | 2019-11-21 |
| JP6952695B2 JP6952695B2 (ja) | 2021-10-20 |
Family
ID=59012608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018529614A Active JP6952695B2 (ja) | 2015-12-09 | 2016-12-08 | インフルエンザウイルス複製の阻害剤、その適用方法および使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US10717732B2 (OSRAM) |
| EP (1) | EP3362451B1 (OSRAM) |
| JP (1) | JP6952695B2 (OSRAM) |
| KR (1) | KR102671350B1 (OSRAM) |
| CN (2) | CN106854205B (OSRAM) |
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Families Citing this family (18)
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| CN106854205B (zh) * | 2015-12-09 | 2019-07-09 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其使用方法和用途 |
| CN109071567B (zh) * | 2016-05-19 | 2021-03-23 | 四川大学 | 抗流感小分子化合物及其制备方法和用途 |
| WO2018033082A1 (en) | 2016-08-16 | 2018-02-22 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication, application methods and uses thereof |
| CN109641868B (zh) | 2016-08-30 | 2021-12-03 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其使用方法和用途 |
| RU2727772C1 (ru) * | 2016-09-05 | 2020-07-23 | Гуандун Рэйновент Байотек Ко., Лтд. | Производные пиримидина против вируса гриппа |
| EP3555095B1 (en) | 2016-12-15 | 2023-04-12 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication and uses thereof |
| US11098042B2 (en) | 2017-01-05 | 2021-08-24 | Sunshine Lake Pharma Co., Ltd. | Inhibitors of influenza virus replication and uses thereof |
| CN110446711B (zh) | 2017-03-02 | 2022-02-15 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其用途 |
| PH12019502376B1 (en) | 2017-04-24 | 2024-06-05 | Cocrystal Pharma Inc | Pyrrolopyrimidine derivatives useful as inhibitors of influenza virus replication |
| CN109384783A (zh) * | 2017-08-09 | 2019-02-26 | 银杏树药业(苏州)有限公司 | 新型杂环化合物及其作为抗流感病毒抑制剂的医药用途 |
| US20200383984A1 (en) * | 2018-02-08 | 2020-12-10 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. | Heteroaryl compounds, pharmaceutical compositions thereof, and their therapeutic use |
| AU2019230497B2 (en) | 2018-03-05 | 2021-08-05 | Guangdong Raynovent Biotech Co., Ltd. | Crystal form and salt form of pyridoimidazole compound and preparation method therefor |
| CN110590768B (zh) * | 2018-06-13 | 2021-02-26 | 银杏树药业(苏州)有限公司 | 杂环化合物、其组合物及其作为抗流感病毒药物的应用 |
| CN114340614B (zh) * | 2019-09-27 | 2024-01-16 | 广东东阳光药业股份有限公司 | 一种奥司他韦制剂 |
| CN110967239B (zh) * | 2020-01-02 | 2022-05-10 | 国家地质实验测试中心 | 一种金属铬溶解氧化方法 |
| TW202202500A (zh) * | 2020-07-10 | 2022-01-16 | 大陸商四川海思科製藥有限公司 | Pb2抑制劑及其製備方法和用途 |
| US12274700B1 (en) | 2020-10-30 | 2025-04-15 | Accencio LLC | Methods of treating symptoms of coronavirus infection with RNA polymerase inhibitors |
| US20250289826A1 (en) * | 2022-04-29 | 2025-09-18 | Tsinghua University | Plpro protein inhibitor, and preparation method and application thereof |
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| PT1730146E (pt) * | 2004-03-30 | 2011-07-11 | Vertex Pharma | Azaindoles úteis como inibidores de jak e outras proteínas quinases |
| PH12015501678B1 (en) | 2009-06-17 | 2022-07-06 | Vertex Pharma | Inhibitors of influenza viruses replication |
| KR20130128436A (ko) | 2010-12-16 | 2013-11-26 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| RU2013132683A (ru) | 2010-12-16 | 2015-01-27 | Вертекс Фармасьютикалз Инкорпорейтед | Ингибиторы репликации вирусов гриппа |
| AU2011343642A1 (en) * | 2010-12-16 | 2013-05-02 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| CN103702998A (zh) * | 2011-07-05 | 2014-04-02 | 沃泰克斯药物股份有限公司 | 生产氮杂吲哚类的方法和中间体 |
| UA118010C2 (uk) * | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| WO2013184985A1 (en) | 2012-06-08 | 2013-12-12 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| AU2014348752C1 (en) | 2013-11-13 | 2019-11-21 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| JP6615755B2 (ja) * | 2013-11-13 | 2019-12-04 | バーテックス ファーマシューティカルズ インコーポレイテッド | インフルエンザウイルスの複製の阻害剤 |
| EP3068434A1 (en) | 2013-11-13 | 2016-09-21 | Vertex Pharmaceuticals Inc. | Formulations of azaindole compounds |
| WO2016020526A1 (en) | 2014-08-08 | 2016-02-11 | Janssen Sciences Ireland Uc | Indoles for use in influenza virus infection |
| KR102531340B1 (ko) | 2014-09-08 | 2023-05-10 | 얀센 사이언시즈 아일랜드 언리미티드 컴퍼니 | 인플루엔자 바이러스 감염에 사용하기 위한 피롤로피리미딘 |
| CN106854205B (zh) * | 2015-12-09 | 2019-07-09 | 广东东阳光药业有限公司 | 流感病毒复制抑制剂及其使用方法和用途 |
| WO2017133664A1 (en) * | 2016-02-05 | 2017-08-10 | Savira Pharmaceuticals Gmbh | Bicyclic pyridine and pyrimidine derivatives and their use in the treatment， amelioration or prevention of influenza |
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2016
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- 2016-12-08 EP EP16872423.5A patent/EP3362451B1/en active Active
- 2016-12-08 RU RU2018124993A patent/RU2737190C2/ru active
- 2016-12-08 WO PCT/CN2016/109079 patent/WO2017097234A1/en not_active Ceased
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2020
- 2020-06-09 US US16/897,256 patent/US11225477B2/en active Active
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