JP2016537358A5 - - Google Patents
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- JP2016537358A5 JP2016537358A5 JP2016530248A JP2016530248A JP2016537358A5 JP 2016537358 A5 JP2016537358 A5 JP 2016537358A5 JP 2016530248 A JP2016530248 A JP 2016530248A JP 2016530248 A JP2016530248 A JP 2016530248A JP 2016537358 A5 JP2016537358 A5 JP 2016537358A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- aryl
- heterocyclyl
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- -1 stereoisomers Chemical class 0.000 claims description 31
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 20
- 125000001425 triazolyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 208000002672 hepatitis B Diseases 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002720 diazolyl group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 230000003612 virological effect Effects 0.000 claims description 8
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- 108010050904 Interferons Proteins 0.000 claims description 6
- 102000014150 Interferons Human genes 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229940079322 interferon Drugs 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 4
- UQZPGHOJMQTOHB-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)-n-ethylethanamine Chemical compound ClCCN(CC)CCCl UQZPGHOJMQTOHB-UHFFFAOYSA-N 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 102100040018 Interferon alpha-2 Human genes 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- WAEDMQMDOHQPFL-UHFFFAOYSA-N n,n-bis(2-chloroethyl)propan-2-amine Chemical compound ClCCN(C(C)C)CCCl WAEDMQMDOHQPFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WDQLRUYAYXDIFW-RWKIJVEZSA-N (2r,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-4-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1 WDQLRUYAYXDIFW-RWKIJVEZSA-N 0.000 claims description 2
- 108010019182 Alloferon Proteins 0.000 claims description 2
- 108700024845 Hepatitis B virus P Proteins 0.000 claims description 2
- 101000959820 Homo sapiens Interferon alpha-1/13 Proteins 0.000 claims description 2
- 102100040019 Interferon alpha-1/13 Human genes 0.000 claims description 2
- 108010078049 Interferon alpha-2 Proteins 0.000 claims description 2
- 108010005716 Interferon beta-1a Proteins 0.000 claims description 2
- 108010047761 Interferon-alpha Proteins 0.000 claims description 2
- 102000006992 Interferon-alpha Human genes 0.000 claims description 2
- 108010079944 Interferon-alpha2b Proteins 0.000 claims description 2
- 108010002350 Interleukin-2 Proteins 0.000 claims description 2
- 102000000588 Interleukin-2 Human genes 0.000 claims description 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 claims description 2
- 229940123066 Polymerase inhibitor Drugs 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
- 229920002305 Schizophyllan Polymers 0.000 claims description 2
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 claims description 2
- 229960001997 adefovir Drugs 0.000 claims description 2
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 claims description 2
- 229960005338 clevudine Drugs 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229960000980 entecavir Drugs 0.000 claims description 2
- YXPVEXCTPGULBZ-WQYNNSOESA-N entecavir hydrate Chemical compound O.C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)C1=C YXPVEXCTPGULBZ-WQYNNSOESA-N 0.000 claims description 2
- 229960004396 famciclovir Drugs 0.000 claims description 2
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 claims description 2
- 108010050151 hepatitis B hyperimmune globulin Proteins 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000002955 immunomodulating agent Substances 0.000 claims description 2
- 229940121354 immunomodulator Drugs 0.000 claims description 2
- 230000002584 immunomodulator Effects 0.000 claims description 2
- 229960004461 interferon beta-1a Drugs 0.000 claims description 2
- 229960001627 lamivudine Drugs 0.000 claims description 2
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 claims description 2
- 229960001614 levamisole Drugs 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229960002480 nitazoxanide Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 claims description 2
- 229950002828 propagermanium Drugs 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
- 229960004556 tenofovir Drugs 0.000 claims description 2
- VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 description 3
- 0 *CC(NC(*)=NC1*)=C1C(**)=O Chemical compound *CC(NC(*)=NC1*)=C1C(**)=O 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- OKRWVGPNIBIPNJ-BOFCVJQFSA-N CCOC(C1=C(CN(CC/S(/C2)=C/C)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CC/S(/C2)=C/C)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1F)=O OKRWVGPNIBIPNJ-BOFCVJQFSA-N 0.000 description 1
- GVJLROIHTUPYMY-CTCAENTCSA-N CCOC(C1=C(CN(CCS(C2)(=O)=O)[C@@H]2C(O)=O)NC(c2ncc[n]2C)N[C@H]1c(c(Cl)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCS(C2)(=O)=O)[C@@H]2C(O)=O)NC(c2ncc[n]2C)N[C@H]1c(c(Cl)c1)ccc1F)=O GVJLROIHTUPYMY-CTCAENTCSA-N 0.000 description 1
- FPPUJHSMNRFRSG-PTYRHSMUSA-N CCOC(C1=C(CN(CCS(C2)=O)C2C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O Chemical compound CCOC(C1=C(CN(CCS(C2)=O)C2C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O FPPUJHSMNRFRSG-PTYRHSMUSA-N 0.000 description 1
- ILHCHZJKIVXGSA-BALUQIDSSA-N CCOC(C1=C(CN(CCS(C2C)(=O)=O)C2C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O Chemical compound CCOC(C1=C(CN(CCS(C2C)(=O)=O)C2C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O ILHCHZJKIVXGSA-BALUQIDSSA-N 0.000 description 1
- NKGYJXUXORBBMJ-XGLRFROISA-N CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[n]2C)=N[C@H]1c(ccc(F)c1)c1Br)=O Chemical compound CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[n]2C)=N[C@H]1c(ccc(F)c1)c1Br)=O NKGYJXUXORBBMJ-XGLRFROISA-N 0.000 description 1
- WOADSNSRPSKYBE-XNUZUHMRSA-N CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[s]2)=N[C@H]1C(CCC(F)=C1)=C1Br)=O Chemical compound CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[s]2)=N[C@H]1C(CCC(F)=C1)=C1Br)=O WOADSNSRPSKYBE-XNUZUHMRSA-N 0.000 description 1
- VRFOJGLFPSWMBJ-XNUZUHMRSA-N CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O Chemical compound CCOC(C1=C(CN(CCSC2)C2(C)C(O)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O VRFOJGLFPSWMBJ-XNUZUHMRSA-N 0.000 description 1
- VMKJQPXFPRLUMS-DAFXYXGESA-N CCOC(C1=C(CN(CCSC2)C2C(N)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O Chemical compound CCOC(C1=C(CN(CCSC2)C2C(N)=O)NC(c2ncc[s]2)=N[C@H]1c(ccc(F)c1)c1Br)=O VMKJQPXFPRLUMS-DAFXYXGESA-N 0.000 description 1
- QTQYOWUIUOYBCH-NNBQYGFHSA-N CCOC(C1=C(CN(CCSC2)C2C(O)=O)NC(c2ncc[n]2C)=N[C@H]1c(c(Br)c1)ccc1F)=O Chemical compound CCOC(C1=C(CN(CCSC2)C2C(O)=O)NC(c2ncc[n]2C)=N[C@H]1c(c(Br)c1)ccc1F)=O QTQYOWUIUOYBCH-NNBQYGFHSA-N 0.000 description 1
- CYSOMRQBOYXORO-ATNAJCNCSA-N CCOC(C1=C(CN(CCSC2)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O Chemical compound CCOC(C1=C(CN(CCSC2)[C@@H]2C(O)=O)NC(c2ncc[s]2)=NC1c(c(Cl)c1)ccc1Cl)=O CYSOMRQBOYXORO-ATNAJCNCSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310590683.6 | 2013-11-19 | ||
| CN201310590683 | 2013-11-19 | ||
| CN201410108925.8 | 2014-03-23 | ||
| CN201410108925 | 2014-03-23 | ||
| PCT/CN2014/091444 WO2015074546A1 (en) | 2013-11-19 | 2014-11-18 | Dihydropyrimidine compounds and their application in pharmaceuticals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016537358A JP2016537358A (ja) | 2016-12-01 |
| JP2016537358A5 true JP2016537358A5 (enExample) | 2017-11-24 |
| JP6524081B2 JP6524081B2 (ja) | 2019-06-05 |
Family
ID=53178948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016530248A Active JP6524081B2 (ja) | 2013-11-19 | 2014-11-18 | ジヒドロピリミジン化合物及び医薬におけるその適用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9498479B2 (enExample) |
| EP (1) | EP3071564B1 (enExample) |
| JP (1) | JP6524081B2 (enExample) |
| KR (1) | KR20160077050A (enExample) |
| CN (1) | CN104650068B (enExample) |
| AU (1) | AU2014352404B2 (enExample) |
| CA (1) | CA2920415A1 (enExample) |
| MX (1) | MX2016006564A (enExample) |
| RU (1) | RU2678990C1 (enExample) |
| WO (1) | WO2015074546A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102284944B1 (ko) | 2013-11-27 | 2021-08-03 | 선샤인 레이크 파르마 컴퍼니 리미티드 | 다이하이드로피리미딘 유도체 및 이의 중간산물의 제조 방법 |
| MX2016012573A (es) | 2014-03-28 | 2018-02-19 | Sunshine Lake Pharma Co Ltd | Compuestos de dihidropirimidina y su aplicacion en productos farmaceuticos. |
| AU2016214799A1 (en) | 2015-02-07 | 2017-06-15 | Sunshine Lake Pharma Co., Ltd. | Complexes and salts of dihydropyrimidine derivatives and their application in pharmaceuticals |
| US10021567B2 (en) * | 2015-03-23 | 2018-07-10 | Qualcomm Incorporated | Schedule selection and connection setup between devices participating in a NAN data link |
| WO2016161268A1 (en) | 2015-04-01 | 2016-10-06 | Enanta Pharmaceuticals, Inc. | Hepatitis b antviral agents |
| US10738035B2 (en) | 2015-05-13 | 2020-08-11 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| WO2017011552A1 (en) | 2015-07-13 | 2017-01-19 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| US10301255B2 (en) | 2015-07-22 | 2019-05-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| WO2017076791A1 (en) | 2015-11-03 | 2017-05-11 | F. Hoffmann-La Roche Ag | Combination therapy of an hbv capsid assembly inhibitor and an interferon |
| WO2017136403A1 (en) | 2016-02-02 | 2017-08-10 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2017136254A1 (en) * | 2016-02-04 | 2017-08-10 | Merck Sharp & Dohme Corp. | Methods of preparing hydroxylamine derivatives useful in the preparation of anti-infective agents |
| KR102398439B1 (ko) | 2016-03-07 | 2022-05-16 | 이난타 파마슈티칼스, 인코포레이티드 | B형 간염 항바이러스제 |
| EP3468561A4 (en) | 2016-06-10 | 2019-12-04 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| EP3503894A1 (en) | 2016-08-24 | 2019-07-03 | H. Hoffnabb-La Roche Ag | Combination therapy of an hbv capsid assembly inhibitor and a nucleos(t)ide analogue |
| JP7139568B2 (ja) | 2016-11-18 | 2022-09-21 | シチュアン ケルン－バイオテック バイオファーマシューティカル カンパニー リミテッド | ジヒドロピリミジン化合物並びにその調製方法及び使用 |
| US11166954B2 (en) | 2016-11-18 | 2021-11-09 | Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd. | Dihydropyrimidine compound and preparation method and use thereof |
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2014
- 2014-11-18 CA CA2920415A patent/CA2920415A1/en not_active Abandoned
- 2014-11-18 WO PCT/CN2014/091444 patent/WO2015074546A1/en not_active Ceased
- 2014-11-18 MX MX2016006564A patent/MX2016006564A/es unknown
- 2014-11-18 EP EP14863769.7A patent/EP3071564B1/en active Active
- 2014-11-18 JP JP2016530248A patent/JP6524081B2/ja active Active
- 2014-11-18 RU RU2016122908A patent/RU2678990C1/ru active
- 2014-11-18 KR KR1020167008618A patent/KR20160077050A/ko not_active Withdrawn
- 2014-11-18 CN CN201410657898.XA patent/CN104650068B/zh active Active
- 2014-11-18 US US15/022,562 patent/US9498479B2/en active Active
- 2014-11-18 AU AU2014352404A patent/AU2014352404B2/en active Active