TW201443053A - 嘧啶酮衍生物及其用於治療、改善或預防病毒疾病之用途 - Google Patents
嘧啶酮衍生物及其用於治療、改善或預防病毒疾病之用途 Download PDFInfo
- Publication number
- TW201443053A TW201443053A TW103100719A TW103100719A TW201443053A TW 201443053 A TW201443053 A TW 201443053A TW 103100719 A TW103100719 A TW 103100719A TW 103100719 A TW103100719 A TW 103100719A TW 201443053 A TW201443053 A TW 201443053A
- Authority
- TW
- Taiwan
- Prior art keywords
- benzyloxy
- pyrimidine
- mmol
- isopropyl
- methyl
- Prior art date
Links
- 230000003612 virological effect Effects 0.000 title claims abstract description 41
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 26
- 201000010099 disease Diseases 0.000 title claims abstract description 25
- 230000002265 prevention Effects 0.000 title claims description 8
- 150000008318 pyrimidones Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 265
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 229940002612 prodrug Drugs 0.000 claims abstract description 12
- 239000000651 prodrug Substances 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims description 319
- 238000000034 method Methods 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 206010022000 influenza Diseases 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 24
- 102100031780 Endonuclease Human genes 0.000 claims description 22
- 108010042407 Endonucleases Proteins 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 20
- 239000003446 ligand Substances 0.000 claims description 20
- 241000700605 Viruses Species 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000002911 sialidase inhibitor Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims description 10
- 238000004458 analytical method Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims description 7
- 241000712464 Orthomyxoviridae Species 0.000 claims description 7
- 239000003888 alpha glucosidase inhibitor Substances 0.000 claims description 7
- 229940126523 co-drug Drugs 0.000 claims description 7
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
- 238000002866 fluorescence resonance energy transfer Methods 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
- 238000003556 assay Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 101800004538 Bradykinin Proteins 0.000 claims description 4
- 241000711573 Coronaviridae Species 0.000 claims description 4
- 241000710781 Flaviviridae Species 0.000 claims description 4
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 4
- 241000700586 Herpesviridae Species 0.000 claims description 4
- 102100035792 Kininogen-1 Human genes 0.000 claims description 4
- 241000711504 Paramyxoviridae Species 0.000 claims description 4
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 4
- 229930003827 cannabinoid Natural products 0.000 claims description 4
- 239000003557 cannabinoid Substances 0.000 claims description 4
- 229940125400 channel inhibitor Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
- 241000711950 Filoviridae Species 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 108020004707 nucleic acids Proteins 0.000 claims description 3
- 150000007523 nucleic acids Chemical class 0.000 claims description 3
- 102000039446 nucleic acids Human genes 0.000 claims description 3
- 241000712892 Arenaviridae Species 0.000 claims description 2
- 241000150350 Peribunyaviridae Species 0.000 claims description 2
- 241000709664 Picornaviridae Species 0.000 claims description 2
- 241000711931 Rhabdoviridae Species 0.000 claims description 2
- 241000710924 Togaviridae Species 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 241000701447 unidentified baculovirus Species 0.000 claims description 2
- 239000000867 Lipoxygenase Inhibitor Substances 0.000 claims 3
- 229940122142 Lipoxygenase inhibitor Drugs 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 241001529453 unidentified herpesvirus Species 0.000 claims 1
- 238000002648 combination therapy Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 774
- -1 2,6-diketohexahydropyridyl Chemical group 0.000 description 419
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 377
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 309
- 235000019439 ethyl acetate Nutrition 0.000 description 297
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 204
- 239000000243 solution Substances 0.000 description 186
- 239000011541 reaction mixture Substances 0.000 description 181
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 171
- 239000007787 solid Substances 0.000 description 158
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 152
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- 238000006243 chemical reaction Methods 0.000 description 105
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
- 230000015572 biosynthetic process Effects 0.000 description 68
- 238000003786 synthesis reaction Methods 0.000 description 66
- 239000012043 crude product Substances 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 239000003112 inhibitor Substances 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 53
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 49
- 239000000725 suspension Substances 0.000 description 46
- 230000009850 completed effect Effects 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 45
- 239000002904 solvent Substances 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 239000012267 brine Substances 0.000 description 41
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 39
- 238000004809 thin layer chromatography Methods 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
- 238000004587 chromatography analysis Methods 0.000 description 36
- 230000002829 reductive effect Effects 0.000 description 36
- 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 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000002253 acid Substances 0.000 description 31
- 229910000420 cerium oxide Inorganic materials 0.000 description 30
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- 239000000284 extract Substances 0.000 description 29
- 229920006395 saturated elastomer Polymers 0.000 description 29
- 239000011734 sodium Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 27
- 239000000706 filtrate Substances 0.000 description 26
- 241000712461 unidentified influenza virus Species 0.000 description 26
- ASOQFOGGRQMLJO-OUKQBFOZSA-N 4-o-tert-butyl 1-o-methyl (e)-3-hydroxy-2-phenylmethoxybut-2-enedioate Chemical compound CC(C)(C)OC(=O)C(/O)=C(C(=O)OC)\OCC1=CC=CC=C1 ASOQFOGGRQMLJO-OUKQBFOZSA-N 0.000 description 25
- 239000010410 layer Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 25
- 230000000840 anti-viral effect Effects 0.000 description 23
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 23
- MKYVWVIBNRPTTC-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-2-[(2-phenylphenyl)methyl]-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1=CC=CC=C1C1=CC=CC=C1 MKYVWVIBNRPTTC-UHFFFAOYSA-N 0.000 description 22
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- 238000004896 high resolution mass spectrometry Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 229940079593 drug Drugs 0.000 description 18
- QNEIZSSWCVSZOS-UHFFFAOYSA-N methyl 2-phenylmethoxyacetate Chemical compound COC(=O)COCC1=CC=CC=C1 QNEIZSSWCVSZOS-UHFFFAOYSA-N 0.000 description 18
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 238000000746 purification Methods 0.000 description 16
- HUDUYUNMIUMUJD-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)cyclopentyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=CC(Cl)=CC=2)CCCC1 HUDUYUNMIUMUJD-UHFFFAOYSA-N 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 14
- 229910004298 SiO 2 Inorganic materials 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000001648 tannin Substances 0.000 description 13
- 235000018553 tannin Nutrition 0.000 description 13
- 229920001864 tannin Polymers 0.000 description 13
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 13
- YBXSVQTZLVNAKE-UHFFFAOYSA-N 2-[[1-(2,5-dichlorophenyl)cyclopentyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C(=CC=C(Cl)C=2)Cl)CCCC1 YBXSVQTZLVNAKE-UHFFFAOYSA-N 0.000 description 12
- QMMFVYPAHWMCMS-DYCDLGHISA-O C[S+]([2H])C Chemical compound C[S+]([2H])C QMMFVYPAHWMCMS-DYCDLGHISA-O 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- 206010057190 Respiratory tract infections Diseases 0.000 description 12
- 239000013058 crude material Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 12
- OMURGRVZFYQLBG-UHFFFAOYSA-N 2-[(2,3-dichlorophenyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1=CC=CC(Cl)=C1Cl OMURGRVZFYQLBG-UHFFFAOYSA-N 0.000 description 11
- XHGFWRFENBSKGD-UHFFFAOYSA-N 2-[decyl(propan-2-yl)amino]ethanol Chemical compound CCCCCCCCCCN(C(C)C)CCO XHGFWRFENBSKGD-UHFFFAOYSA-N 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- 102000028391 RNA cap binding Human genes 0.000 description 11
- 108091000106 RNA cap binding Proteins 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 11
- 239000003443 antiviral agent Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 description 11
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- GDXMFFGTPGAGGX-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCC1 GDXMFFGTPGAGGX-UHFFFAOYSA-N 0.000 description 10
- ORKWQPUBEOIVJF-UHFFFAOYSA-N 2-[(5-methoxy-2-phenylphenyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound C=1C(OC)=CC=C(C=2C=CC=CC=2)C=1CC(N=C1C(O)=O)=NC(O)=C1OCC1=CC=CC=C1 ORKWQPUBEOIVJF-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 235000010357 aspartame Nutrition 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000012265 solid product Substances 0.000 description 10
- 238000013518 transcription Methods 0.000 description 10
- 230000035897 transcription Effects 0.000 description 10
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 9
- FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 9
- CNHTVOASBDBLDV-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)phenyl]acetonitrile Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1CC#N CNHTVOASBDBLDV-UHFFFAOYSA-N 0.000 description 9
- VDQIXKGCAZRYJQ-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)phenyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1=CC=CC=C1C1=CC=CC=C1Cl VDQIXKGCAZRYJQ-UHFFFAOYSA-N 0.000 description 9
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 108020004999 messenger RNA Proteins 0.000 description 9
- 230000010076 replication Effects 0.000 description 9
- WJMWSPUOZRYMJD-UHFFFAOYSA-N (1-phenylcyclopentyl)methanol Chemical compound C=1C=CC=CC=1C1(CO)CCCC1 WJMWSPUOZRYMJD-UHFFFAOYSA-N 0.000 description 8
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 8
- MBWMQVJGGRPLAF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopentyl]acetonitrile Chemical compound C1=CC(Cl)=CC=C1C1(CC#N)CCCC1 MBWMQVJGGRPLAF-UHFFFAOYSA-N 0.000 description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 8
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- OQFQKNFHVKYTDG-UHFFFAOYSA-N n-propan-2-yldecan-1-amine Chemical compound CCCCCCCCCCNC(C)C OQFQKNFHVKYTDG-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- SCKXKZOLUSWBRC-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)cyclopentane-1-carbaldehyde Chemical compound ClC1=CC=C(Cl)C(C2(CCCC2)C=O)=C1 SCKXKZOLUSWBRC-UHFFFAOYSA-N 0.000 description 7
- RTGXLBAVGIYVCT-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1=CC=CC=C1Br RTGXLBAVGIYVCT-UHFFFAOYSA-N 0.000 description 7
- BBEXFVAHGHYTFL-UHFFFAOYSA-N 2-[[1-(4-bromophenyl)cyclopentyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=CC(Br)=CC=2)CCCC1 BBEXFVAHGHYTFL-UHFFFAOYSA-N 0.000 description 7
- NNXRJYFQRYRBQZ-UHFFFAOYSA-N 4-oxo-2-[(1-phenylcyclopentyl)methyl]-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=CC=CC=2)CCCC1 NNXRJYFQRYRBQZ-UHFFFAOYSA-N 0.000 description 7
- NNRSWOGAACVMRX-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-2-[(3-phenylpyridin-2-yl)methyl]-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1=NC=CC=C1C1=CC=CC=C1 NNRSWOGAACVMRX-UHFFFAOYSA-N 0.000 description 7
- SBSFFROVIBCLNP-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-2-[[1-[4-(trifluoromethyl)phenyl]cyclopentyl]methyl]-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=CC(=CC=2)C(F)(F)F)CCCC1 SBSFFROVIBCLNP-UHFFFAOYSA-N 0.000 description 7
- 229910052684 Cerium Inorganic materials 0.000 description 7
- JIKYMOWXZLUFEQ-UHFFFAOYSA-N [1-(2,5-dichlorophenyl)cyclopentyl]methanol Chemical compound C=1C(Cl)=CC=C(Cl)C=1C1(CO)CCCC1 JIKYMOWXZLUFEQ-UHFFFAOYSA-N 0.000 description 7
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 7
- 231100000673 dose–response relationship Toxicity 0.000 description 7
- 239000000890 drug combination Substances 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 230000003834 intracellular effect Effects 0.000 description 7
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- 230000003389 potentiating effect Effects 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- VVEDYRAHNYIUKL-UHFFFAOYSA-N tert-butyl 4-oxo-5-phenylmethoxy-2-[(2-phenylphenyl)methyl]-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1=CC=CC=C1C1=CC=CC=C1 VVEDYRAHNYIUKL-UHFFFAOYSA-N 0.000 description 7
- 230000009385 viral infection Effects 0.000 description 7
- ZEPPSIVTTCKELV-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)cyclopentane-1-carbonitrile Chemical compound ClC1=CC=C(Cl)C(C2(CCCC2)C#N)=C1 ZEPPSIVTTCKELV-UHFFFAOYSA-N 0.000 description 6
- KZCVVVIPPHGCOH-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCCC1 KZCVVVIPPHGCOH-UHFFFAOYSA-N 0.000 description 6
- GTVFCTLUZMPIJI-UHFFFAOYSA-N 2-(2-bromophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1Br GTVFCTLUZMPIJI-UHFFFAOYSA-N 0.000 description 6
- ZAJCNIHBBMCVKH-UHFFFAOYSA-N 2-[1-[4-(trifluoromethyl)phenyl]cyclopentyl]acetonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CC#N)CCCC1 ZAJCNIHBBMCVKH-UHFFFAOYSA-N 0.000 description 6
- XUOLTZBENDBPDQ-UHFFFAOYSA-N 4-oxo-2-[(1-phenylcyclohexyl)methyl]-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=CC=CC=2)CCCCC1 XUOLTZBENDBPDQ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 6
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 235000018102 proteins Nutrition 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- RLNNOWYDUKFUFJ-UHFFFAOYSA-N (1-naphthalen-2-ylcyclopentyl)methanol Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CO)CCCC1 RLNNOWYDUKFUFJ-UHFFFAOYSA-N 0.000 description 5
- NZIDEIRWYRJYAI-UHFFFAOYSA-N (1-phenylcyclohexyl)methanol Chemical compound C=1C=CC=CC=1C1(CO)CCCCC1 NZIDEIRWYRJYAI-UHFFFAOYSA-N 0.000 description 5
- SSBGLUVSZQPEOF-UHFFFAOYSA-N (1-phenylcyclohexyl)methyl methanesulfonate Chemical compound C=1C=CC=CC=1C1(COS(=O)(=O)C)CCCCC1 SSBGLUVSZQPEOF-UHFFFAOYSA-N 0.000 description 5
- FAUPBSCUZRPAIV-UHFFFAOYSA-N (2-methyl-2-phenylpropyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(C)(C)C1=CC=CC=C1 FAUPBSCUZRPAIV-UHFFFAOYSA-N 0.000 description 5
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 5
- ROCIEOUYIMZFGP-UHFFFAOYSA-N 1-naphthalen-2-ylcyclopentane-1-carbonitrile Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C#N)CCCC1 ROCIEOUYIMZFGP-UHFFFAOYSA-N 0.000 description 5
- AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 5
- UHVOPTGFTCRQSQ-UHFFFAOYSA-N 2-(1,1,1-trifluoropropan-2-ylamino)ethanol Chemical compound FC(F)(F)C(C)NCCO UHVOPTGFTCRQSQ-UHFFFAOYSA-N 0.000 description 5
- AJTLJILQHLRKAC-UHFFFAOYSA-N 2-(1-naphthalen-2-ylcyclopentyl)acetonitrile Chemical compound C=1C=C2C=CC=CC2=CC=1C1(CC#N)CCCC1 AJTLJILQHLRKAC-UHFFFAOYSA-N 0.000 description 5
- IZAIMJVWYJKDFF-UHFFFAOYSA-N 2-(1-naphthalen-2-ylcyclopentyl)ethanimidamide;hydrochloride Chemical compound Cl.C=1C=C2C=CC=CC2=CC=1C1(CC(=N)N)CCCC1 IZAIMJVWYJKDFF-UHFFFAOYSA-N 0.000 description 5
- QTZSJWWGPBHVRZ-UHFFFAOYSA-N 2-(1-phenylcyclohexyl)acetonitrile Chemical compound C=1C=CC=CC=1C1(CC#N)CCCCC1 QTZSJWWGPBHVRZ-UHFFFAOYSA-N 0.000 description 5
- MSILGXYVRBMZJA-UHFFFAOYSA-N 2-(1-phenylcyclopentyl)acetonitrile Chemical compound C=1C=CC=CC=1C1(CC#N)CCCC1 MSILGXYVRBMZJA-UHFFFAOYSA-N 0.000 description 5
- BVCOJESIQPNOIF-UHFFFAOYSA-N 2-(2-bromophenyl)acetonitrile Chemical compound BrC1=CC=CC=C1CC#N BVCOJESIQPNOIF-UHFFFAOYSA-N 0.000 description 5
- AQXXSQWNVCHBPR-UHFFFAOYSA-N 2-(2-methyl-2-phenylpropyl)-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound C=1C=CC=CC=1C(C)(C)CC(N=C1C(O)=O)=NC(O)=C1OCC1=CC=CC=C1 AQXXSQWNVCHBPR-UHFFFAOYSA-N 0.000 description 5
- CRGVWXVIMVMUDM-UHFFFAOYSA-N 2-(3-phenylpyridin-2-yl)acetonitrile Chemical compound N#CCC1=NC=CC=C1C1=CC=CC=C1 CRGVWXVIMVMUDM-UHFFFAOYSA-N 0.000 description 5
- LDTHZLHPAOSVKH-UHFFFAOYSA-N 2-[1-(2,5-dichlorophenyl)cyclopentyl]ethanimidamide;hydrochloride Chemical compound Cl.C=1C(Cl)=CC=C(Cl)C=1C1(CC(=N)N)CCCC1 LDTHZLHPAOSVKH-UHFFFAOYSA-N 0.000 description 5
- KEGBVYJMPIYKEQ-UHFFFAOYSA-N 2-[1-(4-bromophenyl)cyclopentyl]acetonitrile Chemical compound C1=CC(Br)=CC=C1C1(CC#N)CCCC1 KEGBVYJMPIYKEQ-UHFFFAOYSA-N 0.000 description 5
- JAFHLKVKGIKNRF-UHFFFAOYSA-N 2-[1-(4-bromophenyl)cyclopentyl]ethanimidamide Chemical compound C=1C=C(Br)C=CC=1C1(CC(=N)N)CCCC1 JAFHLKVKGIKNRF-UHFFFAOYSA-N 0.000 description 5
- VSJLEBWBSJMLND-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)phenyl]-n'-hydroxyethanimidamide Chemical compound ONC(=N)CC1=CC=CC=C1C1=CC=CC=C1Cl VSJLEBWBSJMLND-UHFFFAOYSA-N 0.000 description 5
- GDMNROWUYDCXRE-UHFFFAOYSA-N 3-methyl-3-phenylbutanenitrile Chemical compound N#CCC(C)(C)C1=CC=CC=C1 GDMNROWUYDCXRE-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- DHYFIHUDHWJOEK-UHFFFAOYSA-N [1-(4-bromophenyl)cyclopentyl]methanol Chemical compound C=1C=C(Br)C=CC=1C1(CO)CCCC1 DHYFIHUDHWJOEK-UHFFFAOYSA-N 0.000 description 5
- JPVGEFSYKNYYAU-UHFFFAOYSA-N [1-(4-chlorophenyl)cyclopentyl]methanol Chemical compound C=1C=C(Cl)C=CC=1C1(CO)CCCC1 JPVGEFSYKNYYAU-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 208000037797 influenza A Diseases 0.000 description 5
- 230000010534 mechanism of action Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical compound CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 5
- 229960003752 oseltamivir Drugs 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- VZOPRCCTKLAGPN-ZFJVMAEJSA-L potassium;sodium;(2r,3r)-2,3-dihydroxybutanedioate;tetrahydrate Chemical compound O.O.O.O.[Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VZOPRCCTKLAGPN-ZFJVMAEJSA-L 0.000 description 5
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 5
- 230000001932 seasonal effect Effects 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- QRQXOUFVHQDYJS-UHFFFAOYSA-N (1-phenylcyclopentyl)methyl methanesulfonate Chemical compound C=1C=CC=CC=1C1(COS(=O)(=O)C)CCCC1 QRQXOUFVHQDYJS-UHFFFAOYSA-N 0.000 description 4
- MPKBPMYJCDNVEF-UHFFFAOYSA-N (4-bromothiophen-3-yl)methanol Chemical compound OCC1=CSC=C1Br MPKBPMYJCDNVEF-UHFFFAOYSA-N 0.000 description 4
- YOWQODGCIURGAO-CMDGGOBGSA-N (e)-2-hydroxy-3-phenylmethoxybut-2-enedioic acid Chemical compound OC(=O)C(\O)=C(C(O)=O)/OCC1=CC=CC=C1 YOWQODGCIURGAO-CMDGGOBGSA-N 0.000 description 4
- NLHJLQZXHOLSBX-UHFFFAOYSA-N 1-(4-bromophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC(Br)=CC=C1C1(C#N)CCCC1 NLHJLQZXHOLSBX-UHFFFAOYSA-N 0.000 description 4
- UTOAJPCXCJNPNA-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopentane-1-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1(C=O)CCCC1 UTOAJPCXCJNPNA-UHFFFAOYSA-N 0.000 description 4
- SFLBUWNIEZIWSB-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]cyclopentane-1-carbaldehyde Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(C=O)CCCC1 SFLBUWNIEZIWSB-UHFFFAOYSA-N 0.000 description 4
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 4
- DKKRQSHSFCLKNG-UHFFFAOYSA-N 1-naphthalen-2-ylcyclopentane-1-carbaldehyde Chemical compound C=1C=C2C=CC=CC2=CC=1C1(C=O)CCCC1 DKKRQSHSFCLKNG-UHFFFAOYSA-N 0.000 description 4
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 4
- ZQAPMQNYBFIJJR-UHFFFAOYSA-N 2-(1-phenylcyclopentyl)ethanimidamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(CC(=N)N)CCCC1 ZQAPMQNYBFIJJR-UHFFFAOYSA-N 0.000 description 4
- ADODIWDJDMWOEF-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)ethanimidamide;hydrochloride Chemical compound Cl.COC1=CC=C(Br)C(CC(N)=N)=C1 ADODIWDJDMWOEF-UHFFFAOYSA-N 0.000 description 4
- URJIMSMUIDZLTA-UHFFFAOYSA-N 2-(2-phenylphenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC=C1C1=CC=CC=C1 URJIMSMUIDZLTA-UHFFFAOYSA-N 0.000 description 4
- KSIUCNSNELRLQL-UHFFFAOYSA-N 2-(4-bromothiophen-3-yl)acetonitrile Chemical compound BrC1=CSC=C1CC#N KSIUCNSNELRLQL-UHFFFAOYSA-N 0.000 description 4
- CHUIFAFFCFPALU-UHFFFAOYSA-N 2-(4-phenylthiophen-3-yl)acetonitrile Chemical compound N#CCC1=CSC=C1C1=CC=CC=C1 CHUIFAFFCFPALU-UHFFFAOYSA-N 0.000 description 4
- KDSSSIOQFZSUSO-UHFFFAOYSA-N 2-(4-phenylthiophen-3-yl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CSC=C1C1=CC=CC=C1 KDSSSIOQFZSUSO-UHFFFAOYSA-N 0.000 description 4
- RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- ULPGKXWODVWLMP-UHFFFAOYSA-N 2-[(1-naphthalen-2-ylcyclopentyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)O)=NC=1CC1(C=2C=C3C=CC=CC3=CC=2)CCCC1 ULPGKXWODVWLMP-UHFFFAOYSA-N 0.000 description 4
- KQRXAGHJMZJQAL-UHFFFAOYSA-N 2-[1-(2,5-dichlorophenyl)cyclopentyl]acetonitrile Chemical compound ClC1=CC=C(Cl)C(C2(CC#N)CCCC2)=C1 KQRXAGHJMZJQAL-UHFFFAOYSA-N 0.000 description 4
- FBSYJMMTEKHEAL-UHFFFAOYSA-N 2-[2-(2,3-difluorophenyl)phenyl]acetonitrile Chemical compound FC1=CC=CC(C=2C(=CC=CC=2)CC#N)=C1F FBSYJMMTEKHEAL-UHFFFAOYSA-N 0.000 description 4
- WAOUDEYEBADGNN-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)cyclopentyl]methyl]-n-(2-hydroxyethyl)-4-oxo-5-phenylmethoxy-n-(1,1,1-trifluoropropan-2-yl)-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)N(CCO)C(C)C(F)(F)F)=NC=1CC1(C=2C=CC(Cl)=CC=2)CCCC1 WAOUDEYEBADGNN-UHFFFAOYSA-N 0.000 description 4
- JGMHBULHZNOKMR-UHFFFAOYSA-N 2-methyl-2-(trifluoromethyl)-1,3-oxazolidine Chemical compound FC(F)(F)C1(C)NCCO1 JGMHBULHZNOKMR-UHFFFAOYSA-N 0.000 description 4
- YTFXBGFBUGEUCB-UHFFFAOYSA-N 3-bromo-4-(chloromethyl)thiophene Chemical compound ClCC1=CSC=C1Br YTFXBGFBUGEUCB-UHFFFAOYSA-N 0.000 description 4
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 4
- QXFNFVRKUOTYAG-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-2-pyridin-2-yl-1h-pyrimidine-6-carboxylic acid Chemical compound OC(=O)C1=NC(C=2N=CC=CC=2)=NC(O)=C1OCC1=CC=CC=C1 QXFNFVRKUOTYAG-UHFFFAOYSA-N 0.000 description 4
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229940123734 Endonuclease inhibitor Drugs 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 108020000999 Viral RNA Proteins 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- CSDXGWKBNIWHDT-UHFFFAOYSA-N [1-(2,5-dichlorophenyl)cyclopentyl]methyl methanesulfonate Chemical compound C=1C(Cl)=CC=C(Cl)C=1C1(COS(=O)(=O)C)CCCC1 CSDXGWKBNIWHDT-UHFFFAOYSA-N 0.000 description 4
- KQZYPZKNPALNEU-UHFFFAOYSA-N [1-(4-chlorophenyl)cyclopentyl]methyl methanesulfonate Chemical compound C=1C=C(Cl)C=CC=1C1(COS(=O)(=O)C)CCCC1 KQZYPZKNPALNEU-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000009977 dual effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229940126181 ion channel inhibitor Drugs 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- ZKBMNBLAOMYOHJ-VXGBXAGGSA-N methyl (1r,2s)-2-phenylcyclopentane-1-carboxylate Chemical compound COC(=O)[C@@H]1CCC[C@@H]1C1=CC=CC=C1 ZKBMNBLAOMYOHJ-VXGBXAGGSA-N 0.000 description 4
- YXSARWFSYZHULU-UHFFFAOYSA-N methyl 2-(trifluoromethylsulfonyloxy)cyclopentene-1-carboxylate Chemical compound COC(=O)C1=C(OS(=O)(=O)C(F)(F)F)CCC1 YXSARWFSYZHULU-UHFFFAOYSA-N 0.000 description 4
- ZRXXWPHNSUNQEZ-UHFFFAOYSA-N methyl 2-phenylcyclopentene-1-carboxylate Chemical compound C1CCC(C(=O)OC)=C1C1=CC=CC=C1 ZRXXWPHNSUNQEZ-UHFFFAOYSA-N 0.000 description 4
- QVGVOTGXLLTMAE-UHFFFAOYSA-N n-[2-[tert-butyl(dimethyl)silyl]oxyethyl]propan-2-amine Chemical compound CC(C)NCCO[Si](C)(C)C(C)(C)C QVGVOTGXLLTMAE-UHFFFAOYSA-N 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 4
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
- FEOVLTVDUWEMSA-UHFFFAOYSA-N tert-butyl 2-[(1-naphthalen-2-ylcyclopentyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1(C=2C=C3C=CC=CC3=CC=2)CCCC1 FEOVLTVDUWEMSA-UHFFFAOYSA-N 0.000 description 4
- QGZHMFZDGSZJCR-UHFFFAOYSA-N tert-butyl 2-[[2-(2-chlorophenyl)phenyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1=CC=CC=C1C1=CC=CC=C1Cl QGZHMFZDGSZJCR-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000029812 viral genome replication Effects 0.000 description 4
- NLEIDKFNCMKNIF-MDZDMXLPSA-N (E)-3-phenylmethoxybut-2-en-2-ol Chemical compound C(C1=CC=CC=C1)O\C(\C)=C(/C)\O NLEIDKFNCMKNIF-MDZDMXLPSA-N 0.000 description 3
- HDLXZRNBHPORST-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]cyclopentane-1-carbonitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(C#N)CCCC1 HDLXZRNBHPORST-UHFFFAOYSA-N 0.000 description 3
- CHNMUXHAGUGWJF-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C=O)CCCCC1 CHNMUXHAGUGWJF-UHFFFAOYSA-N 0.000 description 3
- GXIWMXAAPLZOBY-UHFFFAOYSA-N 2-(1-phenylethylamino)ethanol Chemical compound OCCNC(C)C1=CC=CC=C1 GXIWMXAAPLZOBY-UHFFFAOYSA-N 0.000 description 3
- CDGLONLCRQZFNU-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC(Cl)=C1Cl CDGLONLCRQZFNU-UHFFFAOYSA-N 0.000 description 3
- YSCYSJMOXDKGQZ-UHFFFAOYSA-N 2-(3-phenylpyridin-2-yl)ethanimidamide Chemical compound NC(=N)CC1=NC=CC=C1C1=CC=CC=C1 YSCYSJMOXDKGQZ-UHFFFAOYSA-N 0.000 description 3
- IGHVHNVXANBJNH-UHFFFAOYSA-N 2-(4-oxo-1-phenylcyclohexyl)acetonitrile Chemical compound C1CC(=O)CCC1(CC#N)C1=CC=CC=C1 IGHVHNVXANBJNH-UHFFFAOYSA-N 0.000 description 3
- BKUIDGOTIQPEQN-UHFFFAOYSA-N 2-[2-(2,3-difluorophenyl)phenyl]ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1C1=CC=CC(F)=C1F BKUIDGOTIQPEQN-UHFFFAOYSA-N 0.000 description 3
- QAXVCFHHWOWDIQ-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)cyclopentyl]methyl]-n-(2-hydroxyethyl)-4-oxo-n-phenyl-5-phenylmethoxy-1h-pyrimidine-6-carboxamide Chemical compound C=1C=CC=CC=1N(CCO)C(=O)C(C(=C(O)N=1)OCC=2C=CC=CC=2)=NC=1CC1(C=2C=CC(Cl)=CC=2)CCCC1 QAXVCFHHWOWDIQ-UHFFFAOYSA-N 0.000 description 3
- CZTUASLUYCFZKL-UHFFFAOYSA-N 2-o-butyl 1-o-methyl oxalate Chemical compound CCCCOC(=O)C(=O)OC CZTUASLUYCFZKL-UHFFFAOYSA-N 0.000 description 3
- KDNYCTPSPZHJQF-UHFFFAOYSA-N 3-phenylbutan-2-ol Chemical compound CC(O)C(C)C1=CC=CC=C1 KDNYCTPSPZHJQF-UHFFFAOYSA-N 0.000 description 3
- LQBCOOHJJBGAGG-UHFFFAOYSA-N 4-oxo-5-phenylmethoxy-2-[1-(2-phenylphenyl)ethyl]-1h-pyrimidine-6-carboxylic acid Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(C)C(NC1=O)=NC(C(O)=O)=C1OCC1=CC=CC=C1 LQBCOOHJJBGAGG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZEQWRSJQVHEPCG-UHFFFAOYSA-N C(CCC)C(C(Cl)(C)C)CCCCCCCC Chemical compound C(CCC)C(C(Cl)(C)C)CCCCCCCC ZEQWRSJQVHEPCG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 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
- 208000002979 Influenza in Birds Diseases 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 108020005161 RNA Caps Proteins 0.000 description 3
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 3
- 229940124639 Selective inhibitor Drugs 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- NWMZFDWGBCYBJA-UHFFFAOYSA-N [1-[4-(trifluoromethyl)phenyl]cyclopentyl]methanol Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(CO)CCCC1 NWMZFDWGBCYBJA-UHFFFAOYSA-N 0.000 description 3
- GKSQPBCSWMRKDG-UHFFFAOYSA-N acetic acid;2-(2-phenylphenyl)ethanimidamide Chemical compound CC(O)=O.NC(=N)CC1=CC=CC=C1C1=CC=CC=C1 GKSQPBCSWMRKDG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
- 229960003805 amantadine Drugs 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 206010064097 avian influenza Diseases 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- YSJJYGWMTGJNGH-UHFFFAOYSA-N carbon dioxide;ethane-1,2-diol Chemical compound O=C=O.OCCO YSJJYGWMTGJNGH-UHFFFAOYSA-N 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
- 238000011161 development Methods 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- IFOOQGCWMLSFQB-UHFFFAOYSA-N ethyl 3-indol-1-yl-3-methylbutanoate Chemical compound C1=CC=C2N(C(C)(C)CC(=O)OCC)C=CC2=C1 IFOOQGCWMLSFQB-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 229940102223 injectable solution Drugs 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229960000329 ribavirin Drugs 0.000 description 3
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- 229940074446 sodium potassium tartrate tetrahydrate Drugs 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- SPAYOBGXIOAZEV-UHFFFAOYSA-N tert-butyl 2-(naphthalen-1-ylmethyl)-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound CC(C)(C)OC(=O)C=1N=C(CC=2C3=CC=CC=C3C=CC=2)NC(=O)C=1OCC1=CC=CC=C1 SPAYOBGXIOAZEV-UHFFFAOYSA-N 0.000 description 3
- IGSFYLSWLBJJFS-UHFFFAOYSA-N tert-butyl 2-[[1-(4-chlorophenyl)cyclopentyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1(C=2C=CC(Cl)=CC=2)CCCC1 IGSFYLSWLBJJFS-UHFFFAOYSA-N 0.000 description 3
- DXGWYMZLKHQOEO-UHFFFAOYSA-N tert-butyl 4-oxo-5-phenylmethoxy-2-pyridin-2-yl-1h-pyrimidine-6-carboxylate Chemical compound CC(C)(C)OC(=O)C1=NC(C=2N=CC=CC=2)=NC(O)=C1OCC1=CC=CC=C1 DXGWYMZLKHQOEO-UHFFFAOYSA-N 0.000 description 3
- OYAYTQKSBZPBSX-UHFFFAOYSA-N (1-naphthalen-2-ylcyclopentyl)methyl methanesulfonate Chemical compound C=1C=C2C=CC=CC2=CC=1C1(COS(=O)(=O)C)CCCC1 OYAYTQKSBZPBSX-UHFFFAOYSA-N 0.000 description 2
- GWSYUMWTJOICLS-NDXYWBNTSA-N (1r,2s)-2-phenylcyclopentane-1-carboximidamide;hydrochloride Chemical compound Cl.NC(=N)[C@@H]1CCC[C@@H]1C1=CC=CC=C1 GWSYUMWTJOICLS-NDXYWBNTSA-N 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
- ICRAWERFPUHELI-UHFFFAOYSA-N 1-(4-bromophenyl)cyclopentane-1-carbaldehyde Chemical compound C1=CC(Br)=CC=C1C1(C=O)CCCC1 ICRAWERFPUHELI-UHFFFAOYSA-N 0.000 description 2
- TXVNBTOIDITCBF-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclopentane-1-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C#N)CCCC1 TXVNBTOIDITCBF-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
- CZLINJDTCHACEH-UHFFFAOYSA-N 2-(2,3-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(CC#N)=C1Cl CZLINJDTCHACEH-UHFFFAOYSA-N 0.000 description 2
- RLUBZPCKOYSHNQ-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(Cl)C(CC#N)=C1 RLUBZPCKOYSHNQ-UHFFFAOYSA-N 0.000 description 2
- VSSZEBGUCILFSV-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(Br)C(CC#N)=C1 VSSZEBGUCILFSV-UHFFFAOYSA-N 0.000 description 2
- TYSWNHWAGMAOJF-UHFFFAOYSA-N 2-(3-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=CN=C1CC#N TYSWNHWAGMAOJF-UHFFFAOYSA-N 0.000 description 2
- MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 2
- VENLCWMUKMKXEA-UHFFFAOYSA-N 2-(naphthalen-1-ylmethyl)-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound OC(=O)C=1N=C(CC=2C3=CC=CC=C3C=CC=2)NC(=O)C=1OCC1=CC=CC=C1 VENLCWMUKMKXEA-UHFFFAOYSA-N 0.000 description 2
- ZSCVMEDDRCPART-UHFFFAOYSA-N 2-[1-(4-methylphenyl)cyclopentyl]ethanimidamide Chemical compound C1=CC(C)=CC=C1C1(CC(N)=N)CCCC1 ZSCVMEDDRCPART-UHFFFAOYSA-N 0.000 description 2
- VNYGKNLXTBQTJY-UHFFFAOYSA-N 2-[1-(4-methylphenyl)cyclopentyl]ethanimidamide hydrochloride Chemical compound CC1=CC=C(C=C1)C2(CCCC2)CC(=N)N.Cl VNYGKNLXTBQTJY-UHFFFAOYSA-N 0.000 description 2
- FWZXPZJOELALMT-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)phenyl]ethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1C1=CC=CC=C1Cl FWZXPZJOELALMT-UHFFFAOYSA-N 0.000 description 2
- QNKOCFJZJWOXDE-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC(F)(F)C1=CC=C(CC#N)C=C1 QNKOCFJZJWOXDE-UHFFFAOYSA-N 0.000 description 2
- NTKKGQGVFZECME-UHFFFAOYSA-N 2-[[2-(2-chlorophenyl)phenyl]methyl]-n-(2-hydroxyethyl)-4-oxo-5-phenylmethoxy-n-propan-2-yl-1h-pyrimidine-6-carboxamide Chemical class N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)N(CCO)C(C)C)=NC=1CC1=CC=CC=C1C1=CC=CC=C1Cl NTKKGQGVFZECME-UHFFFAOYSA-N 0.000 description 2
- GWQLMSTUGJQEAW-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxy-n-methylethanamine Chemical compound CNCCO[Si](C)(C)C(C)(C)C GWQLMSTUGJQEAW-UHFFFAOYSA-N 0.000 description 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- ZVSCENGNXWPDPL-UHFFFAOYSA-N 2-methyl-2-phenylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=CC=C1 ZVSCENGNXWPDPL-UHFFFAOYSA-N 0.000 description 2
- IANIEJYWVZTFHA-UHFFFAOYSA-N 2-naphthalen-1-ylethanimidamide;hydrochloride Chemical compound Cl.C1=CC=C2C(CC(=N)N)=CC=CC2=C1 IANIEJYWVZTFHA-UHFFFAOYSA-N 0.000 description 2
- LPCWDVLDJVZIHA-UHFFFAOYSA-N 2-naphthalen-2-ylacetonitrile Chemical compound C1=CC=CC2=CC(CC#N)=CC=C21 LPCWDVLDJVZIHA-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ASOQFOGGRQMLJO-UHFFFAOYSA-N 4-o-tert-butyl 1-o-methyl 3-hydroxy-2-phenylmethoxybut-2-enedioate Chemical compound CC(C)(C)OC(=O)C(O)=C(C(=O)OC)OCC1=CC=CC=C1 ASOQFOGGRQMLJO-UHFFFAOYSA-N 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- FUZUXHOKVNHOEK-UHFFFAOYSA-N C(C)(C)(C)C(C(OCCNC)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)C(C(OCCNC)(C)C)CCCCCCCC FUZUXHOKVNHOEK-UHFFFAOYSA-N 0.000 description 2
- BNHRZSROBDHJJP-UHFFFAOYSA-N C=O.C1(=CC=CC=C1)C1CCCC1 Chemical compound C=O.C1(=CC=CC=C1)C1CCCC1 BNHRZSROBDHJJP-UHFFFAOYSA-N 0.000 description 2
- SJURLVIEIKTKGD-UHFFFAOYSA-N CC(C)(C)OC(=O)C(=CC(=O)OC)O Chemical compound CC(C)(C)OC(=O)C(=CC(=O)OC)O SJURLVIEIKTKGD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 108091006146 Channels Proteins 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 2
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000712431 Influenza A virus Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 108060004795 Methyltransferase Proteins 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 102000005348 Neuraminidase Human genes 0.000 description 2
- 108010006232 Neuraminidase Proteins 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 108010067390 Viral Proteins Proteins 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- NUPSHWCALHZGOV-UHFFFAOYSA-N acetic acid n-decyl ester Natural products CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012131 assay buffer Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000007975 buffered saline Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 241001493065 dsRNA viruses Species 0.000 description 2
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 2
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 229940014259 gelatin Drugs 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000037798 influenza B Diseases 0.000 description 2
- 208000037799 influenza C Diseases 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LBTAXVIGKZQJMU-UHFFFAOYSA-N n-propyldecan-1-amine Chemical compound CCCCCCCCCCNCCC LBTAXVIGKZQJMU-UHFFFAOYSA-N 0.000 description 2
- GCNSBDBCGMZVSY-UHFFFAOYSA-N n-pyridin-2-ylpyrimidine-4-carboxamide Chemical compound C=1C=NC=NC=1C(=O)NC1=CC=CC=N1 GCNSBDBCGMZVSY-UHFFFAOYSA-N 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- GMHCEDDZKAYPLB-UHFFFAOYSA-N pyridine-2-carboximidamide;hydrochloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=N1 GMHCEDDZKAYPLB-UHFFFAOYSA-N 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 201000010740 swine influenza Diseases 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- IGAZUJALTBQJBM-UHFFFAOYSA-N tert-butyl 2-(2-methyl-2-phenylpropyl)-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC(C)(C)C1=CC=CC=C1 IGAZUJALTBQJBM-UHFFFAOYSA-N 0.000 description 2
- MBSWKXRTNVVNKH-UHFFFAOYSA-N tert-butyl 2-[(2,6-dichlorophenyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(=O)C(OCC=2C=CC=CC=2)=C(C(=O)OC(C)(C)C)NC=1CC1=C(Cl)C=CC=C1Cl MBSWKXRTNVVNKH-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- 230000006490 viral transcription Effects 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 description 2
- 229960001028 zanamivir Drugs 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- CZHYAAVLICZNRV-UHFFFAOYSA-N (4-bromophenyl)methanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=C(Br)C=C1 CZHYAAVLICZNRV-UHFFFAOYSA-N 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- SXWIAEOZZQADEY-UHFFFAOYSA-N 1,3,5-triphenylbenzene Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=CC(C=2C=CC=CC=2)=C1 SXWIAEOZZQADEY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IJZCIJLGIPCFTE-UHFFFAOYSA-N 1,4-diazaspiro[5.5]undecane;dihydrochloride Chemical compound Cl.Cl.C1CCCCC21NCCNC2 IJZCIJLGIPCFTE-UHFFFAOYSA-N 0.000 description 1
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 1
- MCBVXMDHQQTCFE-UHFFFAOYSA-N 1-(1-phenylethylamino)butan-2-ol Chemical compound CCC(O)CNC(C)C1=CC=CC=C1 MCBVXMDHQQTCFE-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- YNPZJFKKDYCULJ-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)ethanimidamide;hydrochloride Chemical compound [Cl-].NC(=[NH2+])CC1=C(Cl)C=CC=C1Cl YNPZJFKKDYCULJ-UHFFFAOYSA-N 0.000 description 1
- CAKUAVIXSOZILM-UHFFFAOYSA-N 2-(2-bromophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC=C1Br CAKUAVIXSOZILM-UHFFFAOYSA-N 0.000 description 1
- FPSGTRJUQLYLHE-UHFFFAOYSA-N 2-(2-iodophenyl)acetonitrile Chemical compound IC1=CC=CC=C1CC#N FPSGTRJUQLYLHE-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- ZTSVHMDIMMQLSP-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N=1C(=O)C(OCC=2C=CC=CC=2)=C(C(=O)O)NC=1CC1=C(Cl)C=CC=C1Cl ZTSVHMDIMMQLSP-UHFFFAOYSA-N 0.000 description 1
- LPLRVONTLVIGJQ-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)cyclopentyl]methyl]-5-phenylmethoxy-1H-pyrimidin-6-one Chemical compound C(C1=CC=CC=C1)OC=1C=NC(=NC=1O)CC1(CCCC1)C1=CC=C(C=C1)Cl LPLRVONTLVIGJQ-UHFFFAOYSA-N 0.000 description 1
- ADBHIDDMCREJHH-UHFFFAOYSA-N 2-[[2-(2,3-difluorophenyl)phenyl]methyl]-4-oxo-5-phenylmethoxy-1h-pyrimidine-6-carboxylic acid Chemical compound N1C(=O)C(OCC=2C=CC=CC=2)=C(C(=O)O)N=C1CC1=CC=CC=C1C1=CC=CC(F)=C1F ADBHIDDMCREJHH-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- UXUZARPLRQRNNX-DXTOWSMRSA-N 2-amino-9-[(2r,3r,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F UXUZARPLRQRNNX-DXTOWSMRSA-N 0.000 description 1
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
- IFMWWVGVDOTBNN-UHFFFAOYSA-N 2-chloro-2,3,3-trimethylbutane Chemical compound CC(C)(C)C(C)(C)Cl IFMWWVGVDOTBNN-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- IJJJSNBMFDDFBC-UHFFFAOYSA-N 2-cyanoethyl acetate Chemical compound CC(=O)OCCC#N IJJJSNBMFDDFBC-UHFFFAOYSA-N 0.000 description 1
- NYBRWRYIFSUGGJ-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid;hydroiodide Chemical compound I.C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 NYBRWRYIFSUGGJ-UHFFFAOYSA-N 0.000 description 1
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 1
- OQRMWUNUKVUHQO-UHFFFAOYSA-N 2-naphthalen-1-ylacetonitrile Chemical compound C1=CC=C2C(CC#N)=CC=CC2=C1 OQRMWUNUKVUHQO-UHFFFAOYSA-N 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- YHPUKWSIJCYFLM-UHFFFAOYSA-N 2-o-tert-butyl 1-o-methyl oxalate Chemical compound COC(=O)C(=O)OC(C)(C)C YHPUKWSIJCYFLM-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- WXUJYEIALSHRGX-UHFFFAOYSA-N 3-methoxycarbonylheptanoic acid Chemical compound CCCCC(CC(O)=O)C(=O)OC WXUJYEIALSHRGX-UHFFFAOYSA-N 0.000 description 1
- JTZZMXVIHNHASS-UHFFFAOYSA-N 3-methyl-3-phenylbutanoic acid Chemical compound OC(=O)CC(C)(C)C1=CC=CC=C1 JTZZMXVIHNHASS-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
- VDDRQJHPSHDTGX-UHFFFAOYSA-N 3-tert-butyl-2-chloro-2-methylundecane Chemical compound C(C)(C)(C)C(C(C)(C)Cl)CCCCCCCC VDDRQJHPSHDTGX-UHFFFAOYSA-N 0.000 description 1
- XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- APBIZVFQQBCAAT-UHFFFAOYSA-N 4-bromothiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC=C1Br APBIZVFQQBCAAT-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- JXGSPIGZPGWMSP-UHFFFAOYSA-N 4-o-tert-butyl 1-o-methyl 2-hydroxybut-2-enedioate Chemical compound COC(=O)C(O)=CC(=O)OC(C)(C)C JXGSPIGZPGWMSP-UHFFFAOYSA-N 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- OGHAROSJZRTIOK-KQYNXXCUSA-O 7-methylguanosine Chemical group C1=2N=C(N)NC(=O)C=2[N+](C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OGHAROSJZRTIOK-KQYNXXCUSA-O 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000701242 Adenoviridae Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241001533362 Astroviridae Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 201000001178 Bacterial Pneumonia Diseases 0.000 description 1
- 108091032955 Bacterial small RNA Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000776207 Bornaviridae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- CRXBTDWNHVBEIC-HBFHXPTCSA-N CC=1C(=C(C(=C2C=3C(=C(C(=C(C3CC12)[2H])[2H])[2H])[2H])[2H])[2H])C Chemical compound CC=1C(=C(C(=C2C=3C(=C(C(=C(C3CC12)[2H])[2H])[2H])[2H])[2H])[2H])C CRXBTDWNHVBEIC-HBFHXPTCSA-N 0.000 description 1
- 229940124638 COX inhibitor Drugs 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000714198 Caliciviridae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 241000104338 Delitschia confertaspora Species 0.000 description 1
- 241001533413 Deltavirus Species 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- SIXHCCPAJIVTOY-UHFFFAOYSA-N Flutimide Natural products CC(C)CC1=NC(=CC(C)C)C(=O)N(O)C1=O SIXHCCPAJIVTOY-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 102000004366 Glucosidases Human genes 0.000 description 1
- 108010056771 Glucosidases Proteins 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 1
- 206010069767 H1N1 influenza Diseases 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 description 1
- 241000700739 Hepadnaviridae Species 0.000 description 1
- 241001122120 Hepeviridae Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241000713196 Influenza B virus Species 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 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 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 241000713112 Orthobunyavirus Species 0.000 description 1
- 241000150452 Orthohantavirus Species 0.000 description 1
- 208000009620 Orthomyxoviridae Infections Diseases 0.000 description 1
- 241000150218 Orthonairovirus Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical group C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 229940121708 Oxygenase inhibitor Drugs 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 101150020891 PRKCA gene Proteins 0.000 description 1
- 241001631646 Papillomaviridae Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000701945 Parvoviridae Species 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 241000713137 Phlebovirus Species 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001631648 Polyomaviridae Species 0.000 description 1
- 229920003081 Povidone K 30 Polymers 0.000 description 1
- 241000700625 Poxviridae Species 0.000 description 1
- 102000029797 Prion Human genes 0.000 description 1
- 108091000054 Prion Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 1
- 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000702247 Reoviridae Species 0.000 description 1
- 102000004389 Ribonucleoproteins Human genes 0.000 description 1
- 108010081734 Ribonucleoproteins Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 108020004459 Small interfering RNA Proteins 0.000 description 1
- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241000223996 Toxoplasma Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- NKCRWCXWGYLXGQ-UHFFFAOYSA-N [1-(4-bromophenyl)cyclopentyl]methyl methanesulfonate Chemical compound C=1C=C(Br)C=CC=1C1(COS(=O)(=O)C)CCCC1 NKCRWCXWGYLXGQ-UHFFFAOYSA-N 0.000 description 1
- LCKUWDYMVYQQCU-UHFFFAOYSA-N [1-[4-(trifluoromethyl)phenyl]cyclopentyl]methyl methanesulfonate Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(COS(=O)(=O)C)CCCC1 LCKUWDYMVYQQCU-UHFFFAOYSA-N 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 108700010877 adenoviridae proteins Proteins 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940023476 agar Drugs 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 229940092782 bentonite Drugs 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000011325 biochemical measurement Methods 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VPCAAUUIFCAFRZ-UHFFFAOYSA-N butylalumane Chemical compound CCCC[AlH2] VPCAAUUIFCAFRZ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000003556 cannabinoid 2 receptor agonist Substances 0.000 description 1
- 239000007894 caplet Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 238000000423 cell based assay Methods 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940090805 clavulanate Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexane-carboxaldehyde Natural products O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- BALGDZWGNCXXES-UHFFFAOYSA-N cyclopentane;propanoic acid Chemical compound CCC(O)=O.C1CCCC1 BALGDZWGNCXXES-UHFFFAOYSA-N 0.000 description 1
- 150000001940 cyclopentanes Chemical class 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- CLRLHXKNIYJWAW-QBTAGHCHSA-N deaminoneuraminic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H]1OC(O)(C(O)=O)C[C@H](O)[C@H]1O CLRLHXKNIYJWAW-QBTAGHCHSA-N 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000035617 depilation Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 229960002097 dibutylsuccinate Drugs 0.000 description 1
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000003596 drug target Substances 0.000 description 1
- 229940112141 dry powder inhaler Drugs 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 1
- 229950000206 estolate Drugs 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethane-1,2-disulfonate Chemical compound [O-]S(=O)(=O)CCS([O-])(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- ZCGNOVWYSGBHAU-UHFFFAOYSA-N favipiravir Chemical compound NC(=O)C1=NC(F)=CNC1=O ZCGNOVWYSGBHAU-UHFFFAOYSA-N 0.000 description 1
- 229950008454 favipiravir Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- SIXHCCPAJIVTOY-UITAMQMPSA-N flutimide Chemical compound CC(C)CC1=N\C(=C/C(C)C)C(=O)N(O)C1=O SIXHCCPAJIVTOY-UITAMQMPSA-N 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 229960001731 gluceptate Drugs 0.000 description 1
- KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003084 hiv integrase inhibitor Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- WITYUUTUSPKOAB-UHFFFAOYSA-N methyl 2-methyl-2-phenylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=CC=C1 WITYUUTUSPKOAB-UHFFFAOYSA-N 0.000 description 1
- PZBBESSUKAHBHD-UHFFFAOYSA-N methyl 2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1CCCC1=O PZBBESSUKAHBHD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 description 1
- 235000018342 monosodium citrate Nutrition 0.000 description 1
- 239000002524 monosodium citrate Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- NAMAHOPLNMCDSC-UHFFFAOYSA-N n'-hydroxy-2-(3-phenylpyridin-2-yl)ethanimidamide Chemical compound ONC(=N)CC1=NC=CC=C1C1=CC=CC=C1 NAMAHOPLNMCDSC-UHFFFAOYSA-N 0.000 description 1
- HEUWTVFKSKHTRY-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-(2-methyl-2-phenylpropyl)-4-oxo-5-phenylmethoxy-n-propan-2-yl-1h-pyrimidine-6-carboxamide Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)N(CCO)C(C)C)=NC=1CC(C)(C)C1=CC=CC=C1 HEUWTVFKSKHTRY-UHFFFAOYSA-N 0.000 description 1
- MRSVLASJVMRUSV-UHFFFAOYSA-N n-(2-hydroxyethyl)-4-oxo-5-phenylmethoxy-n-propan-2-yl-2-pyridin-2-yl-1h-pyrimidine-6-carboxamide Chemical compound OCCN(C(C)C)C(=O)C1=NC(C=2N=CC=CC=2)=NC(O)=C1OCC1=CC=CC=C1 MRSVLASJVMRUSV-UHFFFAOYSA-N 0.000 description 1
- NNUFPNIVWSBZNU-UHFFFAOYSA-N n-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-n-methyl-4-oxo-5-phenylmethoxy-2-[(2-phenylphenyl)methyl]-1h-pyrimidine-6-carboxamide Chemical class N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)N(CCO[Si](C)(C)C(C)(C)C)C)=NC=1CC1=CC=CC=C1C1=CC=CC=C1 NNUFPNIVWSBZNU-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 1
- IKVDMBQGHZVMRN-UHFFFAOYSA-N n-methyldecan-1-amine Chemical compound CCCCCCCCCCNC IKVDMBQGHZVMRN-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 210000000633 nuclear envelope Anatomy 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 108700013356 oplunofusp Proteins 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003650 oxygenase inhibitor Substances 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- XRQDFNLINLXZLB-CKIKVBCHSA-N peramivir Chemical compound CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N XRQDFNLINLXZLB-CKIKVBCHSA-N 0.000 description 1
- 229960001084 peramivir Drugs 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- RHBIFAXTKNBTRC-UHFFFAOYSA-N pyreno[5,4-b]pyridine Chemical class C1=CC=C2C=CC=3C=CC=C4C=3C2=C1C=1C=CC=NC4=1 RHBIFAXTKNBTRC-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229960000888 rimantadine Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 208000018316 severe headache Diseases 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 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
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PFEFZDQGHVBHAZ-UHFFFAOYSA-N tert-butyl 4-oxo-2-[(1-phenylcyclohexyl)methyl]-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1(C=2C=CC=CC=2)CCCCC1 PFEFZDQGHVBHAZ-UHFFFAOYSA-N 0.000 description 1
- ZETBECNZGHFDJE-UHFFFAOYSA-N tert-butyl 4-oxo-2-[(1-phenylcyclopentyl)methyl]-5-phenylmethoxy-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1(C=2C=CC=CC=2)CCCC1 ZETBECNZGHFDJE-UHFFFAOYSA-N 0.000 description 1
- UQIABHKQXLMGEY-UHFFFAOYSA-N tert-butyl 4-oxo-5-phenylmethoxy-2-[1-(2-phenylphenyl)ethyl]-1h-pyrimidine-6-carboxylate Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(C)C(NC1=O)=NC(C(=O)OC(C)(C)C)=C1OCC1=CC=CC=C1 UQIABHKQXLMGEY-UHFFFAOYSA-N 0.000 description 1
- WRQBOSLEXQUCDR-UHFFFAOYSA-N tert-butyl 4-oxo-5-phenylmethoxy-2-[[1-[4-(trifluoromethyl)phenyl]cyclopentyl]methyl]-1h-pyrimidine-6-carboxylate Chemical compound N=1C(O)=C(OCC=2C=CC=CC=2)C(C(=O)OC(C)(C)C)=NC=1CC1(C=2C=CC(=CC=2)C(F)(F)F)CCCC1 WRQBOSLEXQUCDR-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 229960005196 titanium dioxide Drugs 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002103 transcriptional effect Effects 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
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000017613 viral reproduction Effects 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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
-
- 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
-
- 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
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361750017P | 2013-01-08 | 2013-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201443053A true TW201443053A (zh) | 2014-11-16 |
Family
ID=50070507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW103100719A TW201443053A (zh) | 2013-01-08 | 2014-01-08 | 嘧啶酮衍生物及其用於治療、改善或預防病毒疾病之用途 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9045486B2 (https=) |
| EP (1) | EP2943495B1 (https=) |
| JP (1) | JP2016518305A (https=) |
| KR (1) | KR20150103285A (https=) |
| CN (1) | CN104918942A (https=) |
| AR (1) | AR094378A1 (https=) |
| AU (1) | AU2014204889A1 (https=) |
| BR (1) | BR112015012693A2 (https=) |
| CA (1) | CA2894642A1 (https=) |
| CL (1) | CL2015001916A1 (https=) |
| CR (1) | CR20150337A (https=) |
| EA (1) | EA201591291A1 (https=) |
| HK (1) | HK1211286A1 (https=) |
| IL (1) | IL239656A0 (https=) |
| MA (1) | MA38323B1 (https=) |
| MX (1) | MX2015008293A (https=) |
| PE (1) | PE20151722A1 (https=) |
| PH (1) | PH12015501517A1 (https=) |
| SG (1) | SG11201503946UA (https=) |
| TW (1) | TW201443053A (https=) |
| WO (1) | WO2014108406A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL239682B (en) | 2013-01-08 | 2018-10-31 | Kalvista Pharmaceuticals Ltd | History of benzylamine and 2-(aminomethyl)pyridine |
| GB201300304D0 (en) | 2013-01-08 | 2013-02-20 | Kalvista Pharmaceuticals Ltd | Benzylamine derivatives |
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| WO2015038655A1 (en) | 2013-09-12 | 2015-03-19 | Alios Biopharma, Inc. | Aza-pyridone compounds and uses thereof |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| WO2016145103A1 (en) | 2015-03-11 | 2016-09-15 | Alios Biopharma, Inc. | Aza-pyridone compounds and uses thereof |
| BR112017022550B1 (pt) | 2015-04-28 | 2021-02-23 | Shionogi & Co., Ltd | derivados policíclicos de piridona substituída |
| MX394421B (es) | 2015-04-28 | 2025-03-24 | Shionogi & Co | Derivados de piridona policiclica sustituida y profarmaco de los mismos |
| TW201726678A (zh) | 2015-10-30 | 2017-08-01 | 赫孚孟拉羅股份公司 | 嘧啶酮衍生物及其於治療、改善或預防病毒性疾病之用途 |
| AU2016374416A1 (en) | 2015-12-15 | 2018-06-14 | Shionogi & Co., Ltd. | Medicine for treating influenza characterized by comprising combination of cap-dependent endonuclease inhibitor with anti-influenza drug |
| WO2017109088A1 (en) | 2015-12-23 | 2017-06-29 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| ES2881776T3 (es) | 2016-03-08 | 2021-11-30 | Novartis Ag | Compuestos tricíclicos útiles para tratar las infecciones por ortomixovirus |
| WO2017158147A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| WO2017158151A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| JP6961963B2 (ja) * | 2016-04-01 | 2021-11-05 | 三菱ケミカル株式会社 | フルフラールの製造方法 |
| EP3458455B1 (en) * | 2016-05-20 | 2021-06-16 | F. Hoffmann-La Roche AG | Novel pyrazine compounds with oxygen, sulfur and nitrogen linker for the treatment of infectious diseases |
| IL263235B (en) | 2016-05-31 | 2022-07-01 | Kalvista Pharmaceuticals Ltd | History of pyrazoles as plasma kallikrein inhibitors |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| RU2727962C1 (ru) | 2016-08-10 | 2020-07-28 | Сионоги Энд Ко., Лтд. | Фармацевтические композиции, содержащие замещенные полициклические пиридоновые производные и их пролекарство |
| JOP20170169A1 (ar) | 2016-08-29 | 2019-01-30 | Novartis Ag | مركبات بيريدازين ثلاثية الحلقة مندمجة تفيد في علاج العدوى بفيروس أورثوميكسو |
| HUE057912T2 (hu) | 2017-11-29 | 2022-06-28 | Kalvista Pharmaceuticals Ltd | Plazma kallikrein inhibitort tartalmazó dózisformák |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| KR20230031990A (ko) | 2018-02-28 | 2023-03-07 | 노파르티스 아게 | 인플루엔자의 치료를 위한 오르토믹소바이러스 복제의 억제제로서의 10-(디(페닐)메틸)-4-히드록시-8,9,9a,10-테트라히드로-7h-피롤로[1',2':4,5]피라지노[1,2-b]피리다진-3,5-디온 유도체 및 관련 화합물 |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
| US20240228495A1 (en) * | 2020-03-25 | 2024-07-11 | Sri International | Tricyclic Inhibitors of Influenza Virus Endonuclease |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| WO2024061300A1 (en) * | 2022-09-22 | 2024-03-28 | Insilico Medicine Ip Limited | Inhibitors of trex1 and uses thereof |
| PE20251587A1 (es) | 2022-10-19 | 2025-06-16 | Astrazeneca Ab | 1,3,5-triazinas 2,4,6-trisustituidas como modulares de cx3cr1 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5475109A (en) | 1994-10-17 | 1995-12-12 | Merck & Co., Inc. | Dioxobutanoic acid derivatives as inhibitors of influenza endonuclease |
| WO2005087766A1 (en) | 2004-03-09 | 2005-09-22 | Istituto Di Ricerche Di Biologia Molecolare P Angeletti Spa | Hiv integrase inhibitors |
| CN101014572B (zh) | 2004-09-15 | 2011-07-06 | 盐野义制药株式会社 | 具有hiv整合酶抑制活性的氨基甲酰基吡啶酮衍生物 |
| TW200716632A (en) | 2005-05-16 | 2007-05-01 | Gilead Sciences Inc | Integrase inhibitor compounds |
| CA2616314A1 (en) * | 2005-07-27 | 2007-02-01 | Gilead Sciences, Inc. | Antiviral phosphonate conjugates for inhibition of hiv |
| TWI518084B (zh) | 2009-03-26 | 2016-01-21 | 鹽野義製藥股份有限公司 | 哌喃酮與吡啶酮衍生物之製造方法 |
| US8835461B2 (en) | 2009-03-26 | 2014-09-16 | Shionogi & Co., Ltd. | Substituted 3-hydroxy-4-pyridone derivative |
| LT2444400T (lt) | 2009-06-15 | 2018-06-11 | Shionogi & Co., Ltd. | Pakeistasis policiklinis karbamoilpiridono darinys |
| WO2011000566A2 (en) | 2009-06-30 | 2011-01-06 | Savira Pharmaceuticals Gmbh | Compounds and pharmaceutical compositions for the treatment of negative-sense ssrna virus infections |
| MX2013003139A (es) | 2010-09-24 | 2013-06-18 | Shionogi & Co | Profarmaco de derivado de carbamoilpiridona policiclica substituida. |
-
2014
- 2014-01-07 CN CN201480004139.1A patent/CN104918942A/zh active Pending
- 2014-01-07 KR KR1020157021361A patent/KR20150103285A/ko not_active Withdrawn
- 2014-01-07 HK HK15112095.2A patent/HK1211286A1/xx unknown
- 2014-01-07 US US14/149,284 patent/US9045486B2/en not_active Expired - Fee Related
- 2014-01-07 MA MA38323A patent/MA38323B1/fr unknown
- 2014-01-07 AR ARP140100051A patent/AR094378A1/es unknown
- 2014-01-07 EA EA201591291A patent/EA201591291A1/ru unknown
- 2014-01-07 MX MX2015008293A patent/MX2015008293A/es unknown
- 2014-01-07 WO PCT/EP2014/050165 patent/WO2014108406A1/en not_active Ceased
- 2014-01-07 BR BR112015012693A patent/BR112015012693A2/pt active Search and Examination
- 2014-01-07 PE PE2015001253A patent/PE20151722A1/es not_active Application Discontinuation
- 2014-01-07 CA CA2894642A patent/CA2894642A1/en not_active Abandoned
- 2014-01-07 SG SG11201503946UA patent/SG11201503946UA/en unknown
- 2014-01-07 AU AU2014204889A patent/AU2014204889A1/en not_active Abandoned
- 2014-01-07 JP JP2015551199A patent/JP2016518305A/ja active Pending
- 2014-01-07 EP EP14703275.9A patent/EP2943495B1/en not_active Not-in-force
- 2014-01-08 TW TW103100719A patent/TW201443053A/zh unknown
-
2015
- 2015-06-25 CR CR20150337A patent/CR20150337A/es unknown
- 2015-06-25 IL IL239656A patent/IL239656A0/en unknown
- 2015-07-03 PH PH12015501517A patent/PH12015501517A1/en unknown
- 2015-07-06 CL CL2015001916A patent/CL2015001916A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CL2015001916A1 (es) | 2016-01-22 |
| MX2015008293A (es) | 2016-06-02 |
| HK1211286A1 (en) | 2016-05-20 |
| SG11201503946UA (en) | 2015-09-29 |
| CR20150337A (es) | 2015-11-02 |
| AU2014204889A1 (en) | 2015-06-11 |
| EA201591291A1 (ru) | 2015-12-30 |
| EP2943495A1 (en) | 2015-11-18 |
| US9045486B2 (en) | 2015-06-02 |
| PH12015501517A1 (en) | 2015-11-09 |
| IL239656A0 (en) | 2015-08-31 |
| US20140194431A1 (en) | 2014-07-10 |
| MA38323A1 (fr) | 2017-02-28 |
| BR112015012693A2 (pt) | 2017-07-11 |
| AR094378A1 (es) | 2015-07-29 |
| EP2943495B1 (en) | 2016-12-28 |
| PE20151722A1 (es) | 2015-11-19 |
| KR20150103285A (ko) | 2015-09-09 |
| JP2016518305A (ja) | 2016-06-23 |
| HK1212686A1 (en) | 2016-06-17 |
| MA38323B1 (fr) | 2018-05-31 |
| CA2894642A1 (en) | 2014-07-17 |
| CN104918942A (zh) | 2015-09-16 |
| WO2014108406A1 (en) | 2014-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201443053A (zh) | 嘧啶酮衍生物及其用於治療、改善或預防病毒疾病之用途 | |
| US9701681B2 (en) | Fused ring heteroaryl compounds and their use as Trk inhibitors | |
| CN105246883B (zh) | Dna‑pk抑制剂 | |
| TWI542590B (zh) | 1,2-雙取代雜環化合物 | |
| CN105315285B (zh) | 2,4‑二取代7H‑吡咯并[2,3‑d]嘧啶衍生物、其制法与医药上的用途 | |
| CN112839935A (zh) | 可用作shp2抑制剂的新型杂环衍生物 | |
| WO2019158019A1 (zh) | 嘧啶并环化合物及其制备方法和应用 | |
| TWI572593B (zh) | 四氫喹唑啉酮衍生物 | |
| WO2018177297A1 (zh) | 一种取代内酰胺类化合物及其制备方法和用途 | |
| WO2015127872A1 (zh) | 2,4-二取代苯-1,5-二胺衍生物及其应用以及由其制备的药物组合物和药用组合物 | |
| CN101790527A (zh) | Rho激酶的苯并噻吩抑制剂 | |
| CN106220644A (zh) | 稠环嘧啶氨基衍生物﹑其制备方法、中间体、药物组合物及应用 | |
| CN105452257A (zh) | 新型稠合嘧啶化合物或其盐 | |
| CN105524068B (zh) | 氮杂双环衍生物、其制法与医药上的用途 | |
| CN111936144B (zh) | Jak抑制剂 | |
| WO2016169421A1 (zh) | 咪唑并异吲哚类衍生物、其制备方法及其在医药上的应用 | |
| CN103391932B (zh) | 用于抑制pask的杂环化合物 | |
| TW202515544A (zh) | 作為c-kit激酶抑制劑的醫藥化合物及組合物 | |
| CN114262322A (zh) | 一类细胞程序性坏死抑制剂及其制备方法和用途 | |
| KR20150103672A (ko) | 나프티리디논 유도체 및 바이러스성 질환의 치료, 개선 또는 예방에서의 이의 용도 | |
| WO2023020209A1 (zh) | 含2-芳杂环取代的脲类化合物、其制备方法和用途 | |
| WO2018171740A1 (zh) | 一种哌尼诺安衍生物及其制备方法和应用 | |
| WO2019154053A1 (zh) | Iap抑制剂及其在药物中的应用 | |
| HK1230186B (zh) | 稠环嘧啶氨基衍生物、其制备方法、中间体、药物组合物及应用 | |
| HK1212686B (en) | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |