IL310246A - נוגדי נגיפים שהם נגזרות של נובל ספירופירולידין - Google Patents

Info

Publication number

IL310246A

IL310246A IL310246A IL31024624A IL310246A IL 310246 A IL310246 A IL 310246A IL 310246 A IL310246 A IL 310246A IL 31024624 A IL31024624 A IL 31024624A IL 310246 A IL310246 A IL 310246A

Authority

IL

Israel

Prior art keywords

page

compound

nmr

acetone

mhz

Prior art date

2021-07-29

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• 239000003443 antiviral agent Substances 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 215
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 51
• 238000000034 method Methods 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 239000001257 hydrogen Substances 0.000 claims description 44
• 241000711573 Coronaviridae Species 0.000 claims description 24
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 230000003612 virological effect Effects 0.000 claims description 10
• 241000700605 Viruses Species 0.000 claims description 9
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 239000004365 Protease Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 230000009385 viral infection Effects 0.000 claims description 7
• 208000001528 Coronaviridae Infections Diseases 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 4
• 108091005804 Peptidases Proteins 0.000 claims description 3
• 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 3
• 229920006395 saturated elastomer Polymers 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• 241000315672 SARS coronavirus Species 0.000 claims description 2
• 230000001154 acute effect Effects 0.000 claims description 2
• 230000001684 chronic effect Effects 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• 150000003951 lactams Chemical class 0.000 claims description 2
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 2
• 208000023504 respiratory system disease Diseases 0.000 claims description 2
• 208000032376 Lung infection Diseases 0.000 claims 2
• 241000709661 Enterovirus Species 0.000 claims 1
• 208000019693 Lung disease Diseases 0.000 claims 1
• 241000127282 Middle East respiratory syndrome-related coronavirus Species 0.000 claims 1
• 241001263478 Norovirus Species 0.000 claims 1
• 208000024716 acute asthma Diseases 0.000 claims 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 230
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
• 239000000203 mixture Substances 0.000 description 114
• -1 R23 Chemical compound 0.000 description 102
• CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 91
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 85
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 68
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 65
• 239000000243 solution Substances 0.000 description 61
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
• 239000007787 solid Substances 0.000 description 48
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 40
• 239000000651 prodrug Substances 0.000 description 38
• 229940002612 prodrug Drugs 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
• 239000012267 brine Substances 0.000 description 32
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
• 235000019439 ethyl acetate Nutrition 0.000 description 31
• 239000012044 organic layer Substances 0.000 description 31
• 235000017557 sodium bicarbonate Nutrition 0.000 description 31
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 31
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 30
• 229910052938 sodium sulfate Inorganic materials 0.000 description 30
• 235000011152 sodium sulphate Nutrition 0.000 description 30
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 28
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 27
• 150000002148 esters Chemical class 0.000 description 27
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 26
• 239000007832 Na2SO4 Substances 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• 239000011541 reaction mixture Substances 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
• 238000005481 NMR spectroscopy Methods 0.000 description 21
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 21
• 239000000741 silica gel Substances 0.000 description 21
• 229910002027 silica gel Inorganic materials 0.000 description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
• 125000001424 substituent group Chemical group 0.000 description 18
• 239000007821 HATU Substances 0.000 description 17
• 229940024606 amino acid Drugs 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• 239000003814 drug Substances 0.000 description 17
• 238000010898 silica gel chromatography Methods 0.000 description 17
• 235000001014 amino acid Nutrition 0.000 description 16
• 239000000047 product Substances 0.000 description 16
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 150000001413 amino acids Chemical class 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
• 230000000694 effects Effects 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 101800000504 3C-like protease Proteins 0.000 description 10
• 125000000217 alkyl group Chemical group 0.000 description 10
• 125000000524 functional group Chemical group 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 8
• 125000001931 aliphatic group Chemical group 0.000 description 8
• 150000003862 amino acid derivatives Chemical class 0.000 description 8
• YSHOWEKUVWPFNR-UHFFFAOYSA-N burgess reagent Chemical compound CC[N+](CC)(CC)S(=O)(=O)N=C([O-])OC YSHOWEKUVWPFNR-UHFFFAOYSA-N 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 235000019441 ethanol Nutrition 0.000 description 7
• 239000003112 inhibitor Substances 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 238000002560 therapeutic procedure Methods 0.000 description 7
• 238000011282 treatment Methods 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 241001678559 COVID-19 virus Species 0.000 description 6
• 244000309467 Human Coronavirus Species 0.000 description 6
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
• 241000282412 Homo Species 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 230000000840 anti-viral effect Effects 0.000 description 5
• 230000008901 benefit Effects 0.000 description 5
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• 125000000392 cycloalkenyl group Chemical group 0.000 description 5
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• 239000002552 dosage form Substances 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 5
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• 108090000623 proteins and genes Proteins 0.000 description 5
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• 208000024891 symptom Diseases 0.000 description 5
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• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• 102000004127 Cytokines Human genes 0.000 description 4
• 108090000695 Cytokines Proteins 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 239000000556 agonist Substances 0.000 description 4
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• 229920000615 alginic acid Polymers 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 125000000304 alkynyl group Chemical group 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 125000000539 amino acid group Chemical group 0.000 description 4
• 125000001309 chloro group Chemical group Cl* 0.000 description 4
• 125000004122 cyclic group Chemical group 0.000 description 4
• 125000000753 cycloalkyl group Chemical group 0.000 description 4
• 230000000120 cytopathologic effect Effects 0.000 description 4
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• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 235000018102 proteins Nutrition 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 238000001228 spectrum Methods 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• 235000019698 starch Nutrition 0.000 description 4
• 239000000454 talc Substances 0.000 description 4
• 235000012222 talc Nutrition 0.000 description 4
• 229910052623 talc Inorganic materials 0.000 description 4
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 230000009466 transformation Effects 0.000 description 4
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• 239000001993 wax Substances 0.000 description 4
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• 229940125673 3C-like protease inhibitor Drugs 0.000 description 3
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• ZBVVRIAMQNZAEH-JKWIPACXSA-N C(Cl([2H])([2H])([2H])([2H])([2H])[2H])([ClH][2H])(Cl)[2H] Chemical compound C(Cl([2H])([2H])([2H])([2H])([2H])[2H])([ClH][2H])(Cl)[2H] ZBVVRIAMQNZAEH-JKWIPACXSA-N 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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• 241000282326 Felis catus Species 0.000 description 3
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• 241000124008 Mammalia Species 0.000 description 3
• 229910019142 PO4 Inorganic materials 0.000 description 3
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
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• 208000036142 Viral infection Diseases 0.000 description 3
• 239000002253 acid Substances 0.000 description 3
• 125000002252 acyl group Chemical group 0.000 description 3
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• 150000001299 aldehydes Chemical class 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
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