CN118477088A - N4-羟基胞苷及衍生物和与其相关的抗病毒用途 - Google Patents
N4-羟基胞苷及衍生物和与其相关的抗病毒用途 Download PDFInfo
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- CN118477088A CN118477088A CN202410334363.2A CN202410334363A CN118477088A CN 118477088 A CN118477088 A CN 118477088A CN 202410334363 A CN202410334363 A CN 202410334363A CN 118477088 A CN118477088 A CN 118477088A
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- optionally substituted
- alkyl
- amino acid
- disubstituted
- lipid
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- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 title abstract description 9
- 230000000840 anti-viral effect Effects 0.000 title description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 54
- -1 hydroxy, amino Chemical group 0.000 claims description 1183
- 125000000217 alkyl group Chemical group 0.000 claims description 379
- 150000002632 lipids Chemical class 0.000 claims description 212
- 125000003118 aryl group Chemical group 0.000 claims description 192
- 125000003545 alkoxy group Chemical group 0.000 claims description 172
- 150000003573 thiols Chemical group 0.000 claims description 156
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 154
- 125000000623 heterocyclic group Chemical group 0.000 claims description 151
- 125000001072 heteroaryl group Chemical group 0.000 claims description 149
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 148
- 125000003342 alkenyl group Chemical group 0.000 claims description 147
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 147
- 125000000304 alkynyl group Chemical group 0.000 claims description 146
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 137
- 125000004104 aryloxy group Chemical group 0.000 claims description 135
- 125000003282 alkyl amino group Chemical group 0.000 claims description 134
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 133
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 133
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical group 0.000 claims description 133
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 133
- 125000004414 alkyl thio group Chemical group 0.000 claims description 132
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 132
- 125000001769 aryl amino group Chemical group 0.000 claims description 131
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 131
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 131
- 125000005282 allenyl group Chemical group 0.000 claims description 130
- 125000005110 aryl thio group Chemical group 0.000 claims description 130
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 130
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- 125000005368 heteroarylthio group Chemical group 0.000 claims description 130
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 130
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 129
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 126
- 229910052805 deuterium Inorganic materials 0.000 claims description 126
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 124
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 117
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 116
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 116
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 115
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 115
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 94
- 150000003839 salts Chemical class 0.000 claims description 70
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- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
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- 239000002202 Polyethylene glycol Chemical group 0.000 claims description 34
- 229920001223 polyethylene glycol Chemical group 0.000 claims description 34
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 32
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
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- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N isourea group Chemical group NC(O)=N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 101150065749 Churc1 gene Proteins 0.000 claims description 8
- 102100038239 Protein Churchill Human genes 0.000 claims description 8
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical class O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims description 5
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- 239000003380 propellant Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 4
- 150000005828 hydrofluoroalkanes Chemical class 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical class CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003570 air Substances 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 2
- 229940112141 dry powder inhaler Drugs 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 229940071648 metered dose inhaler Drugs 0.000 claims description 2
- 239000001272 nitrous oxide Substances 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims 18
- 125000003544 oxime group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 125000003875 hemiaminal group Chemical group 0.000 claims 2
- 150000007857 hydrazones Chemical class 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 238000011282 treatment Methods 0.000 abstract description 11
- 201000009182 Chikungunya Diseases 0.000 abstract description 10
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- 206010014587 Encephalitis eastern equine Diseases 0.000 abstract description 6
- 208000006825 Eastern Equine Encephalomyelitis Diseases 0.000 abstract description 5
- 201000005804 Eastern equine encephalitis Diseases 0.000 abstract description 5
- 206010014611 Encephalitis venezuelan equine Diseases 0.000 abstract description 5
- 206010014614 Encephalitis western equine Diseases 0.000 abstract description 5
- 208000002687 Venezuelan Equine Encephalomyelitis Diseases 0.000 abstract description 5
- 201000009145 Venezuelan equine encephalitis Diseases 0.000 abstract description 5
- 208000005466 Western Equine Encephalomyelitis Diseases 0.000 abstract description 5
- 201000005806 Western equine encephalitis Diseases 0.000 abstract description 5
- 201000011001 Ebola Hemorrhagic Fever Diseases 0.000 abstract description 4
- 208000001455 Zika Virus Infection Diseases 0.000 abstract description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 40
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- 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
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- A—HUMAN NECESSITIES
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07H19/06—Pyrimidine radicals
- C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
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- 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
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
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- 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
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- Dispersion Chemistry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| PCT/US2018/064503 WO2019113462A1 (en) | 2017-12-07 | 2018-12-07 | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| CN201880073278.8A CN111372592A (zh) | 2017-12-07 | 2018-12-07 | N4-羟基胞苷及衍生物和与其相关的抗病毒用途 |
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| JP7381190B2 (ja) | 2014-12-26 | 2023-11-15 | エモリー・ユニバーシテイ | Ｎ４－ヒドロキシシチジン及び誘導体並びにそれに関連する抗ウイルス用途 |
| CA3059777C (en) | 2017-05-01 | 2023-02-21 | Gilead Sciences, Inc. | Crystalline forms of (s)-2-ethylbutyl 2-(((s)-(((2r,3s,4r,5r)-5-(4-aminopyrrolo[2,1-f] [1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy) phosphoryl)amino)propanoate |
| PT3706762T (pt) | 2017-12-07 | 2024-12-05 | Univ Emory | N4-hidroxicitidina e derivados e utilizações antivirais relacionadas com os mesmos |
| CN112390838A (zh) * | 2019-08-14 | 2021-02-23 | 斯微(上海)生物科技有限公司 | 一种改性核苷及其合成方法 |
| KR20220066303A (ko) | 2019-09-11 | 2022-05-24 | 더 스크립스 리서치 인스티튜트 | 항바이러스 전구약물 및 이의 약제학적 조성물 |
| WO2021159044A1 (en) * | 2020-02-07 | 2021-08-12 | Emory University | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
| CN111285911B (zh) * | 2020-02-26 | 2021-04-02 | 山东大学 | Gem-1mt两亲小分子化合物及其制剂、制备方法和应用 |
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