NZ314225A - Bis-triazine derivatives and pharmaceutical compositions thereof, useful in the treatment of viral infections - Google Patents

Bis-triazine derivatives and pharmaceutical compositions thereof, useful in the treatment of viral infections

Info

Publication number: NZ314225A
Authority: NZ; New Zealand
Prior art keywords: bis; pharmaceutically acceptable; acceptable salt; triazin; aminophenyl
Prior art date: 1996-02-13

Application number

NZ31422597A

Other languages

English (en)

Inventor

Yakov Gluzman

James Paul Larocque

Bryan Mark O'hara

John Edward Morin

George Alfred Ellestad

Boris Mitsner

Wei-Dong Ding

Yuri Efimovich Raifeld

Antonina Aristotelev Nikitenko

Original Assignee

American Cyanamid Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-02-13

Filing date

1997-02-13

Publication date

2001-03-30

1997-02-13 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

2001-03-30 Publication of NZ314225A publication Critical patent/NZ314225A/en

Links

230000009385 viral infection Effects 0.000 title claims abstract description 18
208000036142 Viral infection Diseases 0.000 title claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
238000011282 treatment Methods 0.000 title description 7
CASHWAGXBJSQDV-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical class C1=NC=NC(C=2N=CN=CN=2)=N1 CASHWAGXBJSQDV-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 120
150000003839 salts Chemical class 0.000 claims abstract description 37
229910052731 fluorine Inorganic materials 0.000 claims abstract description 14
229910052794 bromium Inorganic materials 0.000 claims abstract description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
229910006069 SO3H Inorganic materials 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
241000124008 Mammalia Species 0.000 claims abstract description 8
229910004727 OSO3H Inorganic materials 0.000 claims abstract description 5
239000002253 acid Substances 0.000 claims description 35
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 18
229910052727 yttrium Inorganic materials 0.000 claims description 7
BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 claims description 6
230000000241 respiratory effect Effects 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
241000725303 Human immunodeficiency virus Species 0.000 claims description 3
206010011831 Cytomegalovirus infection Diseases 0.000 claims 1
208000009889 Herpes Simplex Diseases 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
229910052801 chlorine Inorganic materials 0.000 abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
239000000047 product Substances 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
-1 sulfonic acid stilbenes Chemical class 0.000 description 40
239000000243 solution Substances 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 27
239000000203 mixture Substances 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
241000700605 Viruses Species 0.000 description 23
238000003756 stirring Methods 0.000 description 22
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
210000004027 cell Anatomy 0.000 description 19
235000011121 sodium hydroxide Nutrition 0.000 description 19
208000015181 infectious disease Diseases 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
235000002639 sodium chloride Nutrition 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000004128 high performance liquid chromatography Methods 0.000 description 16
239000007787 solid Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
230000000120 cytopathologic effect Effects 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 12
210000004072 lung Anatomy 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
239000000443 aerosol Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
230000003612 virological effect Effects 0.000 description 11
238000003556 assay Methods 0.000 description 10
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
239000008363 phosphate buffer Substances 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 9
REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 description 9
241000711920 Human orthopneumovirus Species 0.000 description 9
241000700584 Simplexvirus Species 0.000 description 9
239000000725 suspension Substances 0.000 description 9
241000701022 Cytomegalovirus Species 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
235000014113 dietary fatty acids Nutrition 0.000 description 8
239000000194 fatty acid Substances 0.000 description 8
229930195729 fatty acid Natural products 0.000 description 8
239000002609 medium Substances 0.000 description 8
238000004007 reversed phase HPLC Methods 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
241000725643 Respiratory syncytial virus Species 0.000 description 7
238000009472 formulation Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003599 detergent Substances 0.000 description 6
238000011534 incubation Methods 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
MBJAPGAZEWPEFB-UHFFFAOYSA-N 5-amino-2-(4-amino-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O MBJAPGAZEWPEFB-UHFFFAOYSA-N 0.000 description 5
239000008367 deionised water Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
230000012010 growth Effects 0.000 description 5
206010022000 influenza Diseases 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
230000017960 syncytium formation Effects 0.000 description 5
150000003918 triazines Chemical class 0.000 description 5
210000003501 vero cell Anatomy 0.000 description 5
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
206010061603 Respiratory syncytial virus infection Diseases 0.000 description 4
241000144282 Sigmodon 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
230000000840 anti-viral effect Effects 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
GFBPEAQMMVZVOQ-UHFFFAOYSA-N 5-hydroxy-2-(4-hydroxy-2-sulfophenyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=CC=C1C1=CC=C(O)C=C1S(O)(=O)=O GFBPEAQMMVZVOQ-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000712003 Human respirovirus 3 Species 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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000003443 antiviral agent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
210000002950 fibroblast Anatomy 0.000 description 3
210000003953 foreskin Anatomy 0.000 description 3
230000004927 fusion Effects 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
238000011081 inoculation Methods 0.000 description 3
239000000902 placebo Substances 0.000 description 3
229940068196 placebo Drugs 0.000 description 3
230000007505 plaque formation Effects 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
208000030925 respiratory syncytial virus infectious disease Diseases 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
238000010792 warming Methods 0.000 description 3
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000282552 Chlorocebus aethiops Species 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000701024 Human betaherpesvirus 5 Species 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
208000035415 Reinfection Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000001506 calcium phosphate Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
230000010261 cell growth Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
229940126142 compound 16 Drugs 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000009036 growth inhibition Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
210000003292 kidney cell Anatomy 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
230000010534 mechanism of action Effects 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
230000008569 process Effects 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
239000000344 soap Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
238000003860 storage Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000011285 therapeutic regimen Methods 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
230000014616 translation Effects 0.000 description 2
241000712461 unidentified influenza virus Species 0.000 description 2
230000006656 viral protein synthesis Effects 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
PGJJYXPMHZOQHJ-UHFFFAOYSA-N 2-[1,2-diamino-2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound C=1C=CC=C(S(O)(=O)=O)C=1C(N)=C(N)C1=CC=CC=C1S(O)(=O)=O PGJJYXPMHZOQHJ-UHFFFAOYSA-N 0.000 description 1
NSMMFSKPGXCMOE-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O NSMMFSKPGXCMOE-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical class NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 description 1
JPVKCHIPRSQDKL-UHFFFAOYSA-N 3-aminobenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1 JPVKCHIPRSQDKL-UHFFFAOYSA-N 0.000 description 1
MOQVHOPVBREXLY-UHFFFAOYSA-N 3h-dioxol-4-ylmethanol Chemical compound OCC1=COOC1 MOQVHOPVBREXLY-UHFFFAOYSA-N 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
PHICKPBIPXXFIP-UHFFFAOYSA-N 5-amino-2-(4-amino-5-methyl-2-sulfophenyl)-4-methylbenzenesulfonic acid Chemical compound C1=C(N)C(C)=CC(C=2C(=CC(N)=C(C)C=2)S(O)(=O)=O)=C1S(O)(=O)=O PHICKPBIPXXFIP-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 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
239000005995 Aluminium silicate Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
206010006448 Bronchiolitis Diseases 0.000 description 1
239000004255 Butylated hydroxyanisole Substances 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241000282465 Canis Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000002330 Congenital Heart Defects Diseases 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
206010011416 Croup infectious Diseases 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
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 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
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 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108091006027 G proteins Proteins 0.000 description 1
102000030782 GTP binding Human genes 0.000 description 1
108091000058 GTP-Binding Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000282412 Homo Species 0.000 description 1
241001027439 Huangpi virus Species 0.000 description 1
241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
206010061218 Inflammation Diseases 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
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
101710085938 Matrix protein Proteins 0.000 description 1
101710127721 Membrane protein Proteins 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
206010029260 Neuroblastoma Diseases 0.000 description 1
108090001074 Nucleocapsid Proteins Proteins 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
101100150875 Oryza sativa subsp. japonica SUS1 gene Proteins 0.000 description 1
101710181008 P protein Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
101710177166 Phosphoprotein Proteins 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
206010057190 Respiratory tract infections Diseases 0.000 description 1
208000036071 Rhinorrhea Diseases 0.000 description 1
206010039101 Rhinorrhoea Diseases 0.000 description 1
241000724205 Rice stripe tenuivirus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
108700005077 Viral Genes Proteins 0.000 description 1
108010067390 Viral Proteins Proteins 0.000 description 1
108020000999 Viral RNA Proteins 0.000 description 1
229930003427 Vitamin E Natural products 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
235000011132 calcium sulphate Nutrition 0.000 description 1
244000309466 calf Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000007910 cell fusion Effects 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
208000028831 congenital heart disease Diseases 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
201000010549 croup Diseases 0.000 description 1
GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000036576 dermal application Effects 0.000 description 1
238000011033 desalting Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
238000007499 fusion processing Methods 0.000 description 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000014509 gene expression Effects 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
230000036541 health Effects 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
231100000516 lung damage Toxicity 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000003595 mist Substances 0.000 description 1
XGTQXAMURMYHPC-UHFFFAOYSA-N n,n-dimethylformamide;thiolane 1,1-dioxide Chemical compound CN(C)C=O.O=S1(=O)CCCC1 XGTQXAMURMYHPC-UHFFFAOYSA-N 0.000 description 1
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000008180 pharmaceutical surfactant Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
YWWGOKNLNRUDAC-UHFFFAOYSA-N piperidine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CNCC(C(O)=O)C1 YWWGOKNLNRUDAC-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
238000002962 plaque-reduction assay Methods 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
208000026425 severe pneumonia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000035897 transcription Effects 0.000 description 1
238000013518 transcription Methods 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 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
238000002211 ultraviolet spectrum Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000006648 viral gene expression Effects 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NZ31422597A 1996-02-13 1997-02-13 Bis-triazine derivatives and pharmaceutical compositions thereof, useful in the treatment of viral infections NZ314225A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US1154296P	1996-02-13	1996-02-13

Publications (1)

Publication Number	Publication Date
NZ314225A true NZ314225A (en)	2001-03-30

Family

ID=21750852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ31422597A NZ314225A (en)	1996-02-13	1997-02-13	Bis-triazine derivatives and pharmaceutical compositions thereof, useful in the treatment of viral infections

Country Status (6)

Country	Link
AU (1)	AU1470497A (fr)
BR (1)	BR9700939A (fr)
CA (1)	CA2197393A1 (fr)
NZ (1)	NZ314225A (fr)
TW (1)	TW438797B (fr)
ZA (1)	ZA971185B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1098644A1 (fr)	1998-07-20	2001-05-16	Bristol-Myers Squibb Company	Antiviraux a base de benzimidazoles substitues
US6489338B2 (en)	2000-06-13	2002-12-03	Bristol-Myers Squibb Company	Imidazopyridine and imidazopyrimidine antiviral agents
US9850251B2 (en)	2013-12-10	2017-12-26	Shandong Danhong Pharmaceutical Co., Ltd.	Imidazole derivative used as antiviral agent and use therof in preparation of medicament
ES2821649T3 (es)	2015-06-08	2021-04-27	Shangdong Danhong Pharmaceutical Co Ltd	Método para preparar derivados de imidazol e intermedios de los mismos y formas cristalinas

1997
- 1997-02-12 CA CA002197393A patent/CA2197393A1/fr not_active Abandoned
- 1997-02-12 ZA ZA971185A patent/ZA971185B/xx unknown
- 1997-02-12 BR BR9700939A patent/BR9700939A/pt active Search and Examination
- 1997-02-13 AU AU14704/97A patent/AU1470497A/en not_active Abandoned
- 1997-02-13 TW TW86101818A patent/TW438797B/zh active
- 1997-02-13 NZ NZ31422597A patent/NZ314225A/en unknown

Also Published As

Publication number	Publication date
BR9700939A (pt)	1998-09-01
ZA971185B (en)	1998-08-12
TW438797B (en)	2001-06-07
CA2197393A1 (fr)	1997-08-14
AU1470497A (en)	1997-08-21

Legal Events

Date	Code	Title	Description
2001-07-27	PSEA	Patent sealed
2001-07-27	RENW	Renewal (renewal fees accepted)

Publication	Publication Date	Title
EP0795549A1 (fr)	1997-09-17	Dérivés de bis-aryloxy(amino)-triazinyl-oxy(amino)aryl, leur préparation et leur utilisation comme agents antiviraux
JP2019048898A (ja)	2019-03-28	インフルエンザウイルスの複製の阻害剤
DK170068B1 (da)	1995-05-15	Analogifremgangsmåde til fremstilling af xanthater
WO2023197791A1 (fr)	2023-10-19	Composé nucléosidique de carbonate cyclique et son utilisation
PT96321B (pt)	1998-06-30	Processo para a preparacao de nucleosidos de purina
RU2294936C1 (ru)	2007-03-10	Натриевая соль 2-метилтио-6-нитро-1,2-4-триазоло[5,1-c]-1,2,4-триазин-7(4h)-она, дигидрат, обладающая противовирусной активностью
US4835168A (en)	1989-05-30	Thiadiazole antiviral agents
US5198552A (en)	1993-03-30	Indole derivative having antiviral, interferon-inducing and immunomodulatory effects
US20230293576A1 (en)	2023-09-21	Antiviral polymers
EP0806418A2 (fr)	1997-11-12	Composés de pyrimidine et agent anti-rotavirus
CN114699419B (zh)	2026-04-28	PLpro蛋白抑制剂在治疗或预防新型冠状病毒感染的药物中的应用
MX2014015648A (es)	2015-08-05	Cianoguanidinas y usos de las mismas.
US5852015A (en)	1998-12-22	Triazine containing anionic compounds useful as antiviral agents
NZ314225A (en)	2001-03-30	Bis-triazine derivatives and pharmaceutical compositions thereof, useful in the treatment of viral infections
US4461757A (en)	1984-07-24	Dimethylaminomethylenated anti-herpes compounds
US5543413A (en)	1996-08-06	Heterocyclic thioamides and related analogs as antiviral agents with a unique mode of action
IE55328B1 (en)	1990-08-15	Ethers and oxime-ethers of alkylaminoalcohols as medicaments and novel products,and processes for their preparation
CA2675934A1 (fr)	2008-07-31	Composes antiviraux
US6433016B1 (en)	2002-08-13	Drugs for treating viral infections
HK1002657A (en)	1998-09-11	Bis-aryloxy(amino)-triazinyl-oxy(amino)aryl derivatives, their preparation and their use as antiviral agents
AU710536B2 (en)	1999-09-23	Triazine containing compounds useful as antiviral agents
EP0762878B1 (fr)	1998-12-16	Inhibition des infections retrovirales par administration de composes de l'acide naphtalene sulfonique
HU177992B (en)	1982-02-28	Process for producing substituted 2,3-dihydro-imidazo-square bracket-1,2--c-square bracket closed-pyrimidine derivatives
EP0229501B1 (fr)	1990-12-27	Agents antiviraux à base de thiadiazole
CN100364975C (zh)	2008-01-30	一种抗呼吸道病毒的药物及用途