AU2006226182C1 - Phosphoramidate derivatives of nucleoside compounds for use in the treatment of cancer - Google Patents
Phosphoramidate derivatives of nucleoside compounds for use in the treatment of cancer Download PDFInfo
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- AU2006226182C1 AU2006226182C1 AU2006226182A AU2006226182A AU2006226182C1 AU 2006226182 C1 AU2006226182 C1 AU 2006226182C1 AU 2006226182 A AU2006226182 A AU 2006226182A AU 2006226182 A AU2006226182 A AU 2006226182A AU 2006226182 C1 AU2006226182 C1 AU 2006226182C1
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- Prior art keywords
- compound according
- treatment
- compound
- prophylaxis
- cancer
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 16
- 201000011510 cancer Diseases 0.000 title claims abstract description 14
- 238000011282 treatment Methods 0.000 title claims description 31
- -1 nucleoside compounds Chemical class 0.000 title abstract description 21
- 239000002777 nucleoside Substances 0.000 title abstract description 6
- 150000008298 phosphoramidates Chemical class 0.000 title abstract description 3
- 208000032839 leukemia Diseases 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 101
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- 229910019142 PO4 Inorganic materials 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000010452 phosphate Substances 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 12
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 235000001014 amino acid Nutrition 0.000 claims description 5
- 150000001413 amino acids Chemical class 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
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- 235000004279 alanine Nutrition 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 22
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 abstract description 15
- 229960002436 cladribine Drugs 0.000 abstract description 12
- WDDPHFBMKLOVOX-AYQXTPAHSA-N clofarabine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F WDDPHFBMKLOVOX-AYQXTPAHSA-N 0.000 abstract description 11
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- 229960000390 fludarabine Drugs 0.000 description 8
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- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
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- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- 229910052794 bromium Inorganic materials 0.000 description 3
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 3
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- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- 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 description 2
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000004400 serine Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229950002757 teoclate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000008521 threonine Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| PCT/GB2006/000932 WO2006100439A1 (en) | 2005-03-21 | 2006-03-16 | Phosphoramidate derivatives of nucleoside compounds for use in the treatment of cancer |
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| AU2006226182A1 AU2006226182A1 (en) | 2006-09-28 |
| AU2006226182B2 AU2006226182B2 (en) | 2011-09-01 |
| AU2006226182C1 true AU2006226182C1 (en) | 2012-06-14 |
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| SI (1) | SI1866324T1 (enExample) |
| WO (1) | WO2006100439A1 (enExample) |
| ZA (1) | ZA200709011B (enExample) |
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| AU2012216500B2 (en) * | 2006-11-24 | 2013-06-20 | Katholieke Universiteit Leuven | Nucleoside aryl phosphoramidates and their use as anti-viral agents for the treatment of hepatitis C virus |
| GB0623493D0 (en) * | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| CN102753563A (zh) | 2008-12-23 | 2012-10-24 | 吉利德制药有限责任公司 | 核苷类似物 |
| AR074977A1 (es) | 2008-12-23 | 2011-03-02 | Pharmasset Inc | Sintesis de nucleosidos de purina |
| US8716262B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| MX2011007364A (es) | 2009-01-09 | 2012-02-28 | Univ Cardiff | Derivados de fosforamidato de compuestos de nuecleosido de guanosina para tratamiento de infecciones virales. |
| PT3290428T (pt) | 2010-03-31 | 2021-12-27 | Gilead Pharmasset Llc | Comprimido compreendendo 2-(((s)-(((2r,3r,4r,5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1-(2h)-il)¿4¿fluoro¿3¿hidroxi¿4¿metiltetrahidrofuran¿2¿il)metoxi) (fenoxi)fosforil)amino)propanoato de (s)- isopropil cristalino |
| GB201016855D0 (en) * | 2010-10-06 | 2010-11-17 | Nucana Biomed Ltd | Chemical compounds |
| EP2658857B1 (en) * | 2010-12-29 | 2016-11-02 | Inhibitex, Inc. | Substituted purine nucleosides, phosphoroamidate and phosphorodiamidate derivatives for treatment of viral infections |
| WO2012094248A1 (en) * | 2011-01-03 | 2012-07-12 | Nanjing Molecular Research, Inc. | O-(substituted benzyl) phosphoramidate compounds and therapeutic use |
| CA2828326C (en) * | 2011-03-01 | 2019-05-07 | Nucana Biomed Limited | Phosphoramidate derivatives of 5 - fluoro - 2' - deoxyuridine for use in the treatment of cancer |
| US9085599B2 (en) | 2011-03-16 | 2015-07-21 | Enanta Pharmaceuticals, Inc. | 2′allene-substituted nucleoside derivatives |
| US10005810B2 (en) | 2012-11-16 | 2018-06-26 | University College Cardiff Consultants Limited | Process for preparing nucleoside prodrugs |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
| BR112016011949A8 (pt) * | 2013-11-27 | 2020-04-28 | Idenix Pharmaceuticals Llc | composto, composição farmacêutica, e, uso dos mesmos |
| KR20170005492A (ko) * | 2014-05-28 | 2017-01-13 | 아이데닉스 파마슈티칼스 엘엘씨 | 암의 치료를 위한 뉴클레오시드 유도체 |
| US20170101431A1 (en) * | 2014-05-28 | 2017-04-13 | Idenix Pharmaceuticals Llc | Nucleoside derivatives for the treatment of cancer |
| IL291927A (en) | 2014-11-28 | 2022-06-01 | NuCana plc | Oligonucleotides containing modified nucleosides |
| IL302877A (en) | 2015-03-06 | 2023-07-01 | Atea Pharmaceuticals Inc | Cell-D-2'-deoxy-2'-alpha-fluoro-2'-cell-C-modified-2-different-N6-purine modified nucleotides for the treatment of hepatitis C virus |
| CA3005444A1 (en) * | 2015-11-16 | 2017-05-26 | Ichorion Therapeutics, Inc. | Nucleic acid prodrugs |
| GB201522764D0 (en) * | 2015-12-23 | 2016-02-03 | Nucana Biomed Ltd | Formulations of phosphate derivatives |
| GB201609600D0 (en) * | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Cancer treatments |
| GB201609602D0 (en) * | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Chemical compounds |
| GB201609601D0 (en) * | 2016-06-01 | 2016-07-13 | Nucana Biomed Ltd | Phosphoramidate compounds |
| LU100724B1 (en) | 2016-07-14 | 2018-07-31 | Atea Pharmaceuticals Inc | Beta-d-2'-deoxy-2'-alpha-fluoro-2'-beta-c-substituted-4'-fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection |
| KR102456417B1 (ko) | 2016-09-07 | 2022-10-19 | 아테아 파마슈티컬즈, 인크. | Rna 바이러스 치료를 위한 2'-치환된-n6-치환된 퓨린 뉴클레오티드 |
| US11202792B2 (en) | 2016-10-12 | 2021-12-21 | Georgetown University | CD99 inhibitors and their uses |
| GB201709471D0 (en) | 2017-06-14 | 2017-07-26 | Nucana Biomed Ltd | Diastereoselective synthesis of hosphate derivatives |
| GB201715011D0 (en) | 2017-09-18 | 2017-11-01 | Nucana Biomed Ltd | Floxuridine synthesis |
| GB201720279D0 (en) | 2017-12-05 | 2018-01-17 | Nucana Biomed Ltd | Anticancer compounds |
| JP2020164521A (ja) * | 2019-03-29 | 2020-10-08 | 国立大学法人 長崎大学 | 抗ウィルス薬 |
| GB201904544D0 (en) | 2019-04-01 | 2019-05-15 | NuCana plc | Anticancer compounds |
| WO2021173713A1 (en) | 2020-02-27 | 2021-09-02 | Atea Pharmaceuticals, Inc. | Highly active compounds against covid-19 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| CN113549076B (zh) * | 2021-07-23 | 2022-12-06 | 中国药科大学 | 一种多取代嘌呤类化合物及其制备方法和应用 |
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| KR880000094B1 (ko) | 1984-12-07 | 1988-02-23 | 보령제약 주식회사 | 뉴클레오시드 유도체의 제조방법 |
| CA2004695C (en) | 1988-12-12 | 1999-08-10 | Rosanne Bonjouklian | Phospholipid nucleosides |
| DE4418690A1 (de) | 1994-05-28 | 1996-01-11 | Boehringer Mannheim Gmbh | Neue Lipidester von Nucleosid-Monophosphaten und deren Verwendung als immunsuppressive Arzneimittel |
| GB9505025D0 (en) * | 1995-03-13 | 1995-05-03 | Medical Res Council | Chemical compounds |
| DE69534745T2 (de) | 1995-04-21 | 2006-10-05 | University Of South Florida, Tampa | Immunopotenzierende 5'-nucleotidase-resistente inosinmonophosphat-derivate und ihre verwendung |
| JP3761958B2 (ja) | 1996-03-12 | 2006-03-29 | 彰 松田 | ３′−カルバモイルアルキルヌクレオシド誘導体 |
| EP1167972B1 (en) * | 1998-01-23 | 2017-03-08 | Kiadis Pharma Intellectual Property B.V. | Enzyme catalyzed therapeutic agents |
| GB9821058D0 (en) * | 1998-09-28 | 1998-11-18 | Univ Cardiff | Chemical compound |
| JP4768909B2 (ja) | 2000-09-29 | 2011-09-07 | 扶桑薬品工業株式会社 | トポイソメラーゼ阻害剤 |
| US20030073618A1 (en) * | 2001-02-08 | 2003-04-17 | Kozhemyakin Leonid A. | Compounds comprising disulfide-containing peptides and nitrogenous bases, and medical uses thereof |
| DE10108851A1 (de) * | 2001-02-23 | 2002-09-12 | Resprotect Gmbh | Verwendung von 5'-substituierten Nukleosiden und/oder deren Prodrugs zur resistenzfreien Therapie von Infektionskrankheiten |
| BR0210594A (pt) | 2001-06-22 | 2005-11-01 | Pharmasset Ltd | (beta)-d ou (beta)-l-3-halonucleosìdeo |
| GB0317009D0 (en) | 2003-07-21 | 2003-08-27 | Univ Cardiff | Chemical compounds |
| GB0401088D0 (en) | 2004-01-19 | 2004-02-18 | Univ Cardiff | Phosphoramidate derivatives |
| CN1972696B (zh) * | 2004-06-24 | 2010-08-11 | 默沙东公司 | 用于治疗rna依赖性rna病毒感染的核苷氨基磷酸芳基酯 |
| WO2007020193A2 (en) * | 2005-08-15 | 2007-02-22 | F. Hoffmann-La Roche Ag | Antiviral phosphoramidates of 4 ' -substituted pronucleotides |
-
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- 2006-03-16 SI SI200630762T patent/SI1866324T1/sl unknown
- 2006-03-16 US US11/886,931 patent/US8263575B2/en not_active Expired - Fee Related
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2010
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2013
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| FU HUA ET AL: "Reaction of ADP with amino acid methyl esters mediated by trimethylsilyl chloride." CHEMICAL COMMUNICATIONS (CAMBRIDGE, ENGLAND) 7 JAN 2003, no. 1, 7 January 2003 (2003-01-07), pages 134-135 * |
| FU, HUA ET AL: "Electrospray ionization mass spectra of amino acid phosphoramidates of adenosine" RAPID COMMUNICATIONS IN MASS SPECTROMETRY , 14(19), 1813-1822 * |
| GRIFFITH, T. M. et al: "Enhanced inhibition of the EDHF phenomenon by a phenyl methoxyalaninyl phosphoramidate derivative of dideoxyadenosine", British J. Pharmacology, 2004, 142, 27-30. * |
| IVNOVSKAYA M. G. et al: Modification of Oligo(poly)nucleotide phosphomonoester groups in aqueous solutions", Nucleosides & Nucleotides, 1987, 6(5), 913-934. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2348741T3 (es) | 2010-12-13 |
| JP5863702B2 (ja) | 2016-02-17 |
| IL186104A (en) | 2013-06-27 |
| JP2013173786A (ja) | 2013-09-05 |
| CA2602324C (en) | 2015-02-24 |
| CA2602324A1 (en) | 2006-09-28 |
| IL186104A0 (en) | 2008-01-20 |
| CY1111538T1 (el) | 2015-08-05 |
| PT1866324E (pt) | 2010-09-16 |
| EP1866324A1 (en) | 2007-12-19 |
| BRPI0609704B8 (pt) | 2021-09-28 |
| CN103936807A (zh) | 2014-07-23 |
| US20090215715A1 (en) | 2009-08-27 |
| GB0505781D0 (en) | 2005-04-27 |
| DE602006014949D1 (de) | 2010-07-29 |
| JP5345381B2 (ja) | 2013-11-20 |
| ATE471334T1 (de) | 2010-07-15 |
| PL1866324T3 (pl) | 2010-12-31 |
| EP1866324B1 (en) | 2010-06-16 |
| DK1866324T3 (da) | 2010-09-27 |
| CN101175763A (zh) | 2008-05-07 |
| US8263575B2 (en) | 2012-09-11 |
| JP2008533191A (ja) | 2008-08-21 |
| BRPI0609704B1 (pt) | 2020-12-01 |
| AU2006226182A1 (en) | 2006-09-28 |
| MX2007011666A (es) | 2007-11-14 |
| WO2006100439A1 (en) | 2006-09-28 |
| SI1866324T1 (sl) | 2010-10-29 |
| BRPI0609704A2 (pt) | 2010-04-20 |
| ZA200709011B (en) | 2009-01-28 |
| AU2006226182B2 (en) | 2011-09-01 |
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