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
- 210000001944 turbinate Anatomy 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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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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- 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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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- A61P31/14—Antivirals for RNA viruses
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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
- A61P31/14—Antivirals for RNA viruses
- 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
-
- 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
-
- 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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- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
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- Dispersion Chemistry (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US201862626998P | 2018-02-06 | 2018-02-06 | |
| US62/626,998 | 2018-02-06 | ||
| US201862760434P | 2018-11-13 | 2018-11-13 | |
| US62/760,434 | 2018-11-13 | ||
| 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 |
| PCT/US2018/064503 WO2019113462A1 (en) | 2017-12-07 | 2018-12-07 | N4-hydroxycytidine and derivatives and anti-viral uses related thereto |
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| CN201880073278.8A Pending 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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| 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 |
| PE20221037A1 (es) | 2019-09-11 | 2022-06-17 | Scripps Research Inst | Profarmacos antivirales y composiciones farmaceuticas de los mismos |
| 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 |
| JP7554841B2 (ja) | 2020-03-12 | 2024-09-20 | ギリアード サイエンシーズ， インコーポレイテッド | １’－シアノヌクレオシドを調製する方法 |
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