CN113501847B - 高效抗乙型肝炎病毒的化合物及其制备方法和应用 - Google Patents
高效抗乙型肝炎病毒的化合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN113501847B CN113501847B CN202111065797.XA CN202111065797A CN113501847B CN 113501847 B CN113501847 B CN 113501847B CN 202111065797 A CN202111065797 A CN 202111065797A CN 113501847 B CN113501847 B CN 113501847B
- Authority
- CN
- China
- Prior art keywords
- hepatitis
- virus
- compound
- preparing
- preparation
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 208000002672 hepatitis B Diseases 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 title claims description 33
- 241000700721 Hepatitis B virus Species 0.000 claims abstract description 40
- -1 4-hydroxy-3-hydroxymethyl-2-methylene cyclopentyl-1-yl Chemical group 0.000 claims abstract description 34
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 241000700605 Viruses Species 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000006454 hepatitis Diseases 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229960003767 alanine Drugs 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims 2
- HFKGHOGNKGGKOF-UHFFFAOYSA-N 2-chloro-2-methylpropane;magnesium Chemical compound [Mg].CC(C)(C)Cl HFKGHOGNKGGKOF-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 17
- 230000000840 anti-viral effect Effects 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 6
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract description 4
- 150000008039 phosphoramides Chemical class 0.000 abstract description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229960000980 entecavir Drugs 0.000 description 6
- 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 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 3
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002777 nucleoside Substances 0.000 description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 description 1
- KUEFXPHXHHANKS-UHFFFAOYSA-N 5-nitro-1h-1,2,4-triazole Chemical compound [O-][N+](=O)C1=NC=NN1 KUEFXPHXHHANKS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 229960001997 adefovir Drugs 0.000 description 1
- 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 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940124405 anti-hepatitis b virus drug Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 230000030944 contact inhibition Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000000311 effect on hepatitis Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000001553 hepatotropic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 238000003753 real-time PCR Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005311 telbivudine Drugs 0.000 description 1
- IQFYYKKMVGJFEH-CSMHCCOUSA-N telbivudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1O[C@@H](CO)[C@H](O)C1 IQFYYKKMVGJFEH-CSMHCCOUSA-N 0.000 description 1
- 229960004556 tenofovir Drugs 0.000 description 1
- 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 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111065797.XA CN113501847B (zh) | 2021-09-13 | 2021-09-13 | 高效抗乙型肝炎病毒的化合物及其制备方法和应用 |
CN202210064857.4A CN114524847B (zh) | 2021-09-13 | 2021-09-13 | 抗乙型肝炎病毒的化合物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111065797.XA CN113501847B (zh) | 2021-09-13 | 2021-09-13 | 高效抗乙型肝炎病毒的化合物及其制备方法和应用 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210064857.4A Division CN114524847B (zh) | 2021-09-13 | 2021-09-13 | 抗乙型肝炎病毒的化合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113501847A CN113501847A (zh) | 2021-10-15 |
CN113501847B true CN113501847B (zh) | 2022-01-11 |
Family
ID=78017192
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111065797.XA Active CN113501847B (zh) | 2021-09-13 | 2021-09-13 | 高效抗乙型肝炎病毒的化合物及其制备方法和应用 |
CN202210064857.4A Active CN114524847B (zh) | 2021-09-13 | 2021-09-13 | 抗乙型肝炎病毒的化合物及其制备方法和应用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210064857.4A Active CN114524847B (zh) | 2021-09-13 | 2021-09-13 | 抗乙型肝炎病毒的化合物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (2) | CN113501847B (zh) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016145142A1 (en) * | 2015-03-10 | 2016-09-15 | Emory University | Nucleotide and nucleoside therapeutics compositions and uses related thereto |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7217815B2 (en) * | 2002-01-17 | 2007-05-15 | Valeant Pharmaceuticals North America | 2-beta -modified-6-substituted adenosine analogs and their use as antiviral agents |
CN102395590A (zh) * | 2009-02-06 | 2012-03-28 | Rfs制药公司 | 用于治疗癌症和病毒感染的嘌呤核苷单磷酸酯前药 |
CN103804416A (zh) * | 2012-11-13 | 2014-05-21 | 中国人民解放军军事医学科学院毒物药物研究所 | 阿昔洛韦的磷酸酯衍生物及其医药用途 |
CN103804417B (zh) * | 2012-11-13 | 2017-09-19 | 北京美倍他药物研究有限公司 | 抗乙肝病毒药物 |
IL280459B2 (en) * | 2014-12-15 | 2023-03-01 | Univ Emory | Phosphoramidates for the treatment of hepatitis b virus |
WO2020121123A2 (en) * | 2018-12-12 | 2020-06-18 | Janssen Biopharma, Inc. | Cyclopentyl nucleoside analogs as anti-virals |
CN109627272A (zh) * | 2018-12-21 | 2019-04-16 | 佛山科学技术学院 | 具有抑制病毒复制活性的核苷磷酸酯类似物、制备方法及其药物用途 |
CN113278041B (zh) * | 2021-07-16 | 2021-10-19 | 南京颐媛生物医学研究院有限公司 | 一种核苷磷酸酯及其合成方法与抗肝炎病毒的制药应用 |
-
2021
- 2021-09-13 CN CN202111065797.XA patent/CN113501847B/zh active Active
- 2021-09-13 CN CN202210064857.4A patent/CN114524847B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016145142A1 (en) * | 2015-03-10 | 2016-09-15 | Emory University | Nucleotide and nucleoside therapeutics compositions and uses related thereto |
Also Published As
Publication number | Publication date |
---|---|
CN114524847B (zh) | 2023-06-20 |
CN113501847A (zh) | 2021-10-15 |
CN114524847A (zh) | 2022-05-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113278041B (zh) | 一种核苷磷酸酯及其合成方法与抗肝炎病毒的制药应用 | |
CN106167504A (zh) | 非环核苷磷酰胺d‑氨基酸酯衍生物及其盐的制备以及在抗病毒方面的应用 | |
WO2017219915A1 (zh) | 一种腺嘌呤衍生物的膦酸酯前药及其在医药上的应用 | |
CN101058535B (zh) | 二(7-羟基-2,3-二氢-1-1h-茚基)醚类及其类似物、合成方法及应用 | |
AU716656B2 (en) | Selected derivatives of K-252a | |
CN106317116A (zh) | 磷酰胺核苷类化合物及其药学上可接受的盐与应用、药物组合物 | |
WO2018000550A1 (zh) | 吡唑并[3,4-d]嘧啶衍生物 | |
WO2016192560A1 (zh) | 替诺福韦单苄酯磷酰胺前药、其制备方法及应用 | |
EP3611170B1 (en) | Deuterated compounds and medical use thereof as antianxiety agents | |
CN116987137B (zh) | 一种加帽化合物及其在mRNA加帽中的应用 | |
CN113501847B (zh) | 高效抗乙型肝炎病毒的化合物及其制备方法和应用 | |
CN113501853B (zh) | 4-硫代尿嘧啶脱氧核苷磷酸酯及其抗病毒药物用途 | |
WO2024027457A1 (zh) | 具有ev71和/或cva16病毒抑制活性的化合物及其应用 | |
CN113461760B (zh) | 4-硫代脱氧胸苷衍生物及其抗乙肝病毒制药应用 | |
CN114230623B (zh) | 2-硫代-n-羟基胞嘧啶核糖核苷磷酸酯及其抗病毒药物用途 | |
CN106699812A (zh) | 替诺福韦前药的制备和纯化方法 | |
CN1634943A (zh) | 一组非环核苷酸类似物及其合成方法和在抗病毒中的应用 | |
CN111777638B (zh) | 喹啉类化合物、其制备方法、药物组合物和用途 | |
CN111393366B (zh) | 四氢异喹啉类衍生物、制备方法、药物组合物及应用 | |
CN111423483A (zh) | 环二核苷酸前药分子及其制备方法和应用 | |
CN115141206B (zh) | 一种ɑ-硫辛酸石蒜碱偶联物及其制备方法和应用 | |
CN117003766B (zh) | 一种抗流感病毒衍生物及其用途 | |
CN112679489B (zh) | N-磺酰基杂环衍生物及其制药用途 | |
CN117209427A (zh) | 两面针碱四环类似物-哌嗪杂合体及其制备与应用 | |
CN114262348A (zh) | 环状核苷磷酸酯类化合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230109 Address after: North Area, 3rd Floor, Building 4, 1058 Halley Road, 888 Cailun Road, China (Shanghai) Pilot Free Trade Zone, Pudong New Area, Shanghai, 200000 Patentee after: Guoqing biomedical (Shanghai) Co.,Ltd. Address before: Room 950-1, block a, phase I, Zhongdan Ecological Life Science Industrial Park, no.3-1, xinjinhu Road, Jiangbei new district, Nanjing City, Jiangsu Province, 210000 Patentee before: Nanjing Yiyuan Biomedical Research Institute Co.,Ltd. Patentee before: Guoqing biomedical (Shanghai) Co.,Ltd. |
|
TR01 | Transfer of patent right |