OA11716A - Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatmentof hepatitis C virus and other togaviruses. - Google Patents

Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatmentof hepatitis C virus and other togaviruses. Download PDF

Info

Publication number: OA11716A
Authority: OA; OAPI
Prior art keywords: formula; compound; virus; compounds; alkyl
Prior art date: 1998-11-24

Application number

OA1200100128A

Other languages

English (en)

Inventor

Clarence Nathaniel Ahlem

James Martin Frincke

Patrick T Prendergast

Original Assignee

Hollis Eden Pharmaceuticals

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.)

1998-11-24

Filing date

1999-11-24

Publication date

2005-01-25

1999-11-24 Application filed by Hollis Eden Pharmaceuticals filed Critical Hollis Eden Pharmaceuticals

2005-01-25 Publication of OA11716A publication Critical patent/OA11716A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 311
239000002243 precursor Substances 0.000 title claims abstract description 8
241000711549 Hepacivirus C Species 0.000 title claims abstract description 6
239000002207 metabolite Substances 0.000 title abstract description 3
238000000034 method Methods 0.000 claims abstract description 105
241000700605 Viruses Species 0.000 claims abstract description 37
208000015181 infectious disease Diseases 0.000 claims abstract description 37
241000531123 GB virus C Species 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 16
241000710831 Flavivirus Species 0.000 claims abstract description 15
208000024891 symptom Diseases 0.000 claims abstract description 12
241000283690 Bos taurus Species 0.000 claims abstract description 6
206010012735 Diarrhoea Diseases 0.000 claims abstract description 4
-1 sulfate ester Chemical class 0.000 claims description 182
239000000203 mixture Substances 0.000 claims description 105
125000000217 alkyl group Chemical group 0.000 claims description 53
125000006239 protecting group Chemical group 0.000 claims description 42
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 36
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 26
150000002148 esters Chemical class 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 20
125000000623 heterocyclic group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
241000282414 Homo sapiens Species 0.000 claims description 19
229960002903 benzyl benzoate Drugs 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
150000008134 glucuronides Chemical group 0.000 claims description 17
150000007970 thio esters Chemical class 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000000304 alkynyl group Chemical group 0.000 claims description 16
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
125000004429 atom Chemical group 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
235000019445 benzyl alcohol Nutrition 0.000 claims description 9
235000014113 dietary fatty acids Nutrition 0.000 claims description 9
229930195729 fatty acid Natural products 0.000 claims description 9
239000000194 fatty acid Substances 0.000 claims description 9
150000004665 fatty acids Chemical class 0.000 claims description 9
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
150000003555 thioacetals Chemical class 0.000 claims description 7
241000288906 Primates Species 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
241001430294 unidentified retrovirus Species 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
206010037660 Pyrexia Diseases 0.000 claims description 4
206010014599 encephalitis Diseases 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
241000710780 Bovine viral diarrhea virus 1 Species 0.000 claims description 2
241001493160 California encephalitis virus Species 0.000 claims description 2
241000204955 Colorado tick fever virus Species 0.000 claims description 2
241000710815 Dengue virus 2 Species 0.000 claims description 2
241000710872 Dengue virus 3 Species 0.000 claims description 2
241000710844 Dengue virus 4 Species 0.000 claims description 2
208000000832 Equine Encephalomyelitis Diseases 0.000 claims description 2
QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 claims description 2
241001529916 Hepatitis GB virus B Species 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 2
241000710842 Japanese encephalitis virus Species 0.000 claims description 2
241000710961 Semliki Forest virus Species 0.000 claims description 2
241000710888 St. Louis encephalitis virus Species 0.000 claims description 2
241000710951 Western equine encephalitis virus Species 0.000 claims description 2
201000003486 coccidioidomycosis Diseases 0.000 claims description 2
QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-LUJOEAJASA-N 0.000 claims description 2
239000011734 sodium Chemical group 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
208000007887 Alphavirus Infections Diseases 0.000 claims 1
241000701465 BK virus strain GS Species 0.000 claims 1
241000725619 Dengue virus Species 0.000 claims 1
241000490229 Eucephalus Species 0.000 claims 1
208000002199 Rubivirus Infections Diseases 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 38
229910052760 oxygen Inorganic materials 0.000 abstract description 17
208000005176 Hepatitis C Diseases 0.000 abstract description 16
208000000255 Togaviridae Infections Diseases 0.000 abstract description 16
239000003795 chemical substances by application Substances 0.000 abstract description 16
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 abstract description 14
210000002540 macrophage Anatomy 0.000 abstract description 14
229960000329 ribavirin Drugs 0.000 abstract description 14
230000003647 oxidation Effects 0.000 abstract description 13
238000007254 oxidation reaction Methods 0.000 abstract description 13
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 abstract description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 11
230000004936 stimulating effect Effects 0.000 abstract description 11
102000006992 Interferon-alpha Human genes 0.000 abstract description 10
108010047761 Interferon-alpha Proteins 0.000 abstract description 10
241000710778 Pestivirus Species 0.000 abstract description 10
239000001301 oxygen Substances 0.000 abstract description 10
238000009423 ventilation Methods 0.000 abstract description 9
241000710929 Alphavirus Species 0.000 abstract description 8
206010019773 Hepatitis G Diseases 0.000 abstract description 5
238000002648 combination therapy Methods 0.000 abstract description 5
241000710799 Rubella virus Species 0.000 abstract description 4
241000710772 Yellow fever virus Species 0.000 abstract description 3
229940051021 yellow-fever virus Drugs 0.000 abstract description 3
230000002265 prevention Effects 0.000 abstract 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 58
238000009472 formulation Methods 0.000 description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
239000000546 pharmaceutical excipient Substances 0.000 description 34
102000014150 Interferons Human genes 0.000 description 26
108010050904 Interferons Proteins 0.000 description 26
125000004432 carbon atom Chemical group C* 0.000 description 26
150000003431 steroids Chemical class 0.000 description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
229940079322 interferon Drugs 0.000 description 22
239000000047 product Substances 0.000 description 20
235000013772 propylene glycol Nutrition 0.000 description 19
229960004063 propylene glycol Drugs 0.000 description 19
239000007788 liquid Substances 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 13
239000000243 solution Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
229920001223 polyethylene glycol Polymers 0.000 description 11
230000001225 therapeutic effect Effects 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
229910052717 sulfur Inorganic materials 0.000 description 10
229930182480 glucuronide Natural products 0.000 description 9
208000006454 hepatitis Diseases 0.000 description 9
208000010710 hepatitis C virus infection Diseases 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
239000000725 suspension Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229920000858 Cyclodextrin Polymers 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
241000710801 Rubivirus Species 0.000 description 8
229960004217 benzyl alcohol Drugs 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
239000003814 drug Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229910052698 phosphorus Inorganic materials 0.000 description 8
229940068886 polyethylene glycol 300 Drugs 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
238000002560 therapeutic procedure Methods 0.000 description 8
208000006154 Chronic hepatitis C Diseases 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000008280 blood Substances 0.000 description 7
238000003776 cleavage reaction Methods 0.000 description 7
125000005842 heteroatom Chemical group 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 7
210000004185 liver Anatomy 0.000 description 7
239000005022 packaging material Substances 0.000 description 7
229910052710 silicon Inorganic materials 0.000 description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
238000012552 review Methods 0.000 description 6
230000007017 scission Effects 0.000 description 6
230000000707 stereoselective effect Effects 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
206010008909 Chronic Hepatitis Diseases 0.000 description 5
108091034117 Oligonucleotide Proteins 0.000 description 5
229920002556 Polyethylene Glycol 300 Polymers 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
229940024606 amino acid Drugs 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 5
230000000840 anti-viral effect Effects 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
229930182478 glucoside Natural products 0.000 description 5
150000008131 glucosides Chemical class 0.000 description 5
231100000283 hepatitis Toxicity 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
230000004044 response Effects 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 4
239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 4
102000004127 Cytokines Human genes 0.000 description 4
108090000695 Cytokines Proteins 0.000 description 4
206010019799 Hepatitis viral Diseases 0.000 description 4
FDQAOULAVFHKBX-UHFFFAOYSA-N Isosilybin A Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC(=CC=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
241000283984 Rodentia Species 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
239000013011 aqueous formulation Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
235000019197 fats Nutrition 0.000 description 4
239000008187 granular material Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
229940047124 interferons Drugs 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
238000010253 intravenous injection Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 description 4
235000007625 naringenin Nutrition 0.000 description 4
229940117954 naringenin Drugs 0.000 description 4
DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 4
229930019673 naringin Natural products 0.000 description 4
229940052490 naringin Drugs 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
230000008569 process Effects 0.000 description 4
230000009467 reduction Effects 0.000 description 4
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
229940124597 therapeutic agent Drugs 0.000 description 4
230000001052 transient effect Effects 0.000 description 4
201000001862 viral hepatitis Diseases 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
RMCRQBAILCLJGU-HIBKWJPLSA-N Didymin Chemical compound C1=CC(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 RMCRQBAILCLJGU-HIBKWJPLSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
206010016654 Fibrosis Diseases 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 3
102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 3
208000031886 HIV Infections Diseases 0.000 description 3
241000282412 Homo Species 0.000 description 3
241000713772 Human immunodeficiency virus 1 Species 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
SEBFKMXJBCUCAI-UHFFFAOYSA-N NSC 227190 Natural products C1=C(O)C(OC)=CC(C2C(OC3=CC=C(C=C3O2)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-UHFFFAOYSA-N 0.000 description 3
RMCRQBAILCLJGU-UHFFFAOYSA-N Neoponcirin Natural products C1=CC(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 RMCRQBAILCLJGU-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
102000003929 Transaminases Human genes 0.000 description 3
108090000340 Transaminases Proteins 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229960005274 benzocaine Drugs 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229920005549 butyl rubber Polymers 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000010949 copper Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
230000002255 enzymatic effect Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229930003935 flavonoid Natural products 0.000 description 3
235000017173 flavonoids Nutrition 0.000 description 3
150000002215 flavonoids Chemical class 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
238000001802 infusion Methods 0.000 description 3
239000002502 liposome Substances 0.000 description 3
239000003589 local anesthetic agent Substances 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000178 monomer Substances 0.000 description 3
239000004006 olive oil Substances 0.000 description 3
235000008390 olive oil Nutrition 0.000 description 3
125000000962 organic group Chemical group 0.000 description 3
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 3
229960004919 procaine Drugs 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000000714 pyrimidinyl group Chemical group 0.000 description 3
SEBFKMXJBCUCAI-HKTJVKLFSA-N silibinin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC=C(C=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 SEBFKMXJBCUCAI-HKTJVKLFSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
FDQAOULAVFHKBX-KMRPREKFSA-N (+)-Isosilybin A Natural products C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@@H]2[C@@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-KMRPREKFSA-N 0.000 description 2
FDQAOULAVFHKBX-HKTJVKLFSA-N (2r,3r)-3,5,7-trihydroxy-2-[(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@@H]2[C@H](C(=O)C3=C(O)C=C(O)C=C3O2)O)CO)=C1 FDQAOULAVFHKBX-HKTJVKLFSA-N 0.000 description 2
DGGOLFCPSUVVHX-RTHJTPBESA-N (2s)-2-(3,4-dihydroxyphenyl)-8-hydroxy-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(C(=O)C[C@H](O2)C=3C=C(O)C(O)=CC=3)C2=C1O DGGOLFCPSUVVHX-RTHJTPBESA-N 0.000 description 2
DSSYKIVIOFKYAU-OIBJUYFYSA-N (S)-camphor Chemical compound C1C[C@]2(C)C(=O)C[C@H]1C2(C)C DSSYKIVIOFKYAU-OIBJUYFYSA-N 0.000 description 2
LTYOJFOTFBGRPP-GHRIWEEISA-N (e)-(2-phenyl-2,3-dihydrochromen-4-ylidene)hydrazine Chemical compound O1C2=CC=CC=C2C(=N/N)/CC1C1=CC=CC=C1 LTYOJFOTFBGRPP-GHRIWEEISA-N 0.000 description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
150000000185 1,3-diols Chemical group 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
VOCGSQHKPZSIKB-FQEVSTJZSA-N Bavachinin Chemical compound C1([C@H]2OC=3C=C(C(=CC=3C(=O)C2)CC=C(C)C)OC)=CC=C(O)C=C1 VOCGSQHKPZSIKB-FQEVSTJZSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
208000003322 Coinfection Diseases 0.000 description 2
241000699800 Cricetinae Species 0.000 description 2
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 2
241000450599 DNA viruses Species 0.000 description 2
241000283086 Equidae Species 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
239000001116 FEMA 4028 Substances 0.000 description 2
241000282324 Felis Species 0.000 description 2
DGGOLFCPSUVVHX-UHFFFAOYSA-N Flavanomarein Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C(=O)CC(O2)C=3C=C(O)C(O)=CC=3)C2=C1O DGGOLFCPSUVVHX-UHFFFAOYSA-N 0.000 description 2
241000710781 Flaviviridae Species 0.000 description 2
230000005526 G1 to G0 transition Effects 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 2
241000713340 Human immunodeficiency virus 2 Species 0.000 description 2
102100037852 Insulin-like growth factor I Human genes 0.000 description 2
108090000174 Interleukin-10 Proteins 0.000 description 2
108090000978 Interleukin-4 Proteins 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDMGQPNVTKUNHV-UHFFFAOYSA-N Isosilybin Natural products C1=C(O)C(OC)=CC=C1C1C(CO)OC2=CC=C(C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)C=C2O1 KDMGQPNVTKUNHV-UHFFFAOYSA-N 0.000 description 2
CYGIJEJDYJOUAN-UHFFFAOYSA-N Isosilychristin Natural products C1=C(O)C(OC)=CC(C2C3C=C(C4C(C3=O)(O)OCC42)C2C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 CYGIJEJDYJOUAN-UHFFFAOYSA-N 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
125000003047 N-acetyl group Chemical group 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 2
VLGROHBNWZUINI-UHFFFAOYSA-N Silybin Natural products COc1cc(ccc1O)C2OC3C=C(C=CC3OC2CO)C4Oc5cc(O)cc(O)c5C(=O)C4O VLGROHBNWZUINI-UHFFFAOYSA-N 0.000 description 2
RIAZZJBPJQWPIS-UHFFFAOYSA-N Silychristin Natural products COc1cc(ccc1O)C2OC3C(C=C(C=C3O)C4Oc5cc(O)cc(O)c5C(=O)C4O)C2CO RIAZZJBPJQWPIS-UHFFFAOYSA-N 0.000 description 2
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 2
229930006000 Sucrose Natural products 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000004809 Teflon Substances 0.000 description 2
229920006362 Teflon® Polymers 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
208000024799 Thyroid disease Diseases 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
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 2
150000001241 acetals Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
150000008209 arabinosides Chemical class 0.000 description 2
230000001363 autoimmune Effects 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
125000004069 aziridinyl group Chemical group 0.000 description 2
VOCGSQHKPZSIKB-UHFFFAOYSA-N bavachinin A Natural products C1C(=O)C=2C=C(CC=C(C)C)C(OC)=CC=2OC1C1=CC=C(O)C=C1 VOCGSQHKPZSIKB-UHFFFAOYSA-N 0.000 description 2
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
235000011175 beta-cyclodextrine Nutrition 0.000 description 2
229960004853 betadex Drugs 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000006243 carbonyl protecting group Chemical group 0.000 description 2
230000003915 cell function Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
208000020403 chronic hepatitis C virus infection Diseases 0.000 description 2
230000007882 cirrhosis Effects 0.000 description 2
208000019425 cirrhosis of liver Diseases 0.000 description 2
238000013329 compounding Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000012084 conversion product Substances 0.000 description 2
239000003246 corticosteroid Substances 0.000 description 2
229960001334 corticosteroids Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
229960000935 dehydrated alcohol Drugs 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
SOTDSZCPWKTPCI-UHFFFAOYSA-N didymin Natural products COc1ccc(cc1)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 SOTDSZCPWKTPCI-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
241001493065 dsRNA viruses Species 0.000 description 2
206010016256 fatigue Diseases 0.000 description 2
239000000945 filler Substances 0.000 description 2
229930003949 flavanone Natural products 0.000 description 2
150000002207 flavanone derivatives Chemical class 0.000 description 2
235000011981 flavanones Nutrition 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000008195 galaktosides Chemical class 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000036541 health Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
239000012678 infectious agent Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229950000038 interferon alfa Drugs 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
239000012528 membrane Substances 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
150000005217 methyl ethers Chemical class 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000000465 moulding Methods 0.000 description 2
UNGWSRDLOLQJGX-LVZFUZTISA-N n-acetyl-n-[(e)-(2-phenyl-2,3-dihydrochromen-4-ylidene)amino]acetamide Chemical compound O1C2=CC=CC=C2C(=N/N(C(=O)C)C(C)=O)/CC1C1=CC=CC=C1 UNGWSRDLOLQJGX-LVZFUZTISA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
239000006072 paste Substances 0.000 description 2
JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
229940068918 polyethylene glycol 400 Drugs 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
230000000750 progressive effect Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
150000008265 rhamnosides Chemical class 0.000 description 2
108010038379 sargramostim Proteins 0.000 description 2
235000014899 silybin Nutrition 0.000 description 2
229940043175 silybin Drugs 0.000 description 2
BMLIIPOXVWESJG-LMBCONBSSA-N silychristin Chemical compound C1=C(O)C(OC)=CC([C@H]2[C@@H](C3=C(C(=CC(=C3)[C@@H]3[C@H](C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-LMBCONBSSA-N 0.000 description 2
BMLIIPOXVWESJG-UHFFFAOYSA-N silychristin A Natural products C1=C(O)C(OC)=CC(C2C(C3=C(C(=CC(=C3)C3C(C(=O)C4=C(O)C=C(O)C=C4O3)O)O)O2)CO)=C1 BMLIIPOXVWESJG-UHFFFAOYSA-N 0.000 description 2
238000009097 single-agent therapy Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012439 solid excipient Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000005017 substituted alkenyl group Chemical group 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
208000021510 thyroid gland disease Diseases 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
230000009466 transformation Effects 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
230000003442 weekly effect Effects 0.000 description 2
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical group CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
RUDATBOHQWOJDD-UHFFFAOYSA-N (3beta,5beta,7alpha)-3,7-Dihydroxycholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 RUDATBOHQWOJDD-UHFFFAOYSA-N 0.000 description 1
SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 description 1
ZOJKRWXDNYZASL-NSCUHMNNSA-N (e)-4-methoxybut-2-enoic acid Chemical compound COC\C=C\C(O)=O ZOJKRWXDNYZASL-NSCUHMNNSA-N 0.000 description 1
ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 1
MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
ATPQHBQUXWELOE-UHFFFAOYSA-N 1-hydroxysulfanyl-2,4-dinitrobenzene Chemical compound OSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ATPQHBQUXWELOE-UHFFFAOYSA-N 0.000 description 1
AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 1
KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical group C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
FFFIRKXTFQCCKJ-UHFFFAOYSA-M 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=C(C([O-])=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-M 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
FFMBYMANYCDCMK-UHFFFAOYSA-N 2,5-dihydro-1h-imidazole Chemical group C1NCN=C1 FFMBYMANYCDCMK-UHFFFAOYSA-N 0.000 description 1
YURLCYGZYWDCHL-UHFFFAOYSA-N 2-(2,6-dichloro-4-methylphenoxy)acetic acid Chemical compound CC1=CC(Cl)=C(OCC(O)=O)C(Cl)=C1 YURLCYGZYWDCHL-UHFFFAOYSA-N 0.000 description 1
TYYAMZMDZWXHHA-UHFFFAOYSA-N 2-(dibromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(Br)Br TYYAMZMDZWXHHA-UHFFFAOYSA-N 0.000 description 1
NEESBXODYBPTFM-UHFFFAOYSA-N 2-(methylsulfanylmethoxy)ethyl hydrogen carbonate Chemical compound CSCOCCOC(O)=O NEESBXODYBPTFM-UHFFFAOYSA-N 0.000 description 1
QXQMENSTZKYZCE-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetic acid Chemical compound CCC(C)(C)C1=CC=C(OCC(O)=O)C(C(C)(C)CC)=C1 QXQMENSTZKYZCE-UHFFFAOYSA-N 0.000 description 1
SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
CJNZAXGUTKBIHP-UHFFFAOYSA-M 2-iodobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-M 0.000 description 1
125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
125000004922 2-methyl-3-pentyl group Chemical group CC(C)C(CC)* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
125000004919 3-methyl-2-pentyl group Chemical group CC(C(C)*)CC 0.000 description 1
125000004921 3-methyl-3-pentyl group Chemical group CC(CC)(CC)* 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical group C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical group C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
UBARRNXCKBFUEN-UHFFFAOYSA-N 4,5-diphenyl-5h-1,3-oxazol-2-one Chemical compound N=1C(=O)OC(C=2C=CC=CC=2)C=1C1=CC=CC=C1 UBARRNXCKBFUEN-UHFFFAOYSA-N 0.000 description 1
CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
NDRAHSMAGKWWFZ-UHFFFAOYSA-N 4-(methylsulfanylmethoxy)butanoic acid Chemical compound CSCOCCCC(O)=O NDRAHSMAGKWWFZ-UHFFFAOYSA-N 0.000 description 1
WAGMYTXJRVPMGW-UHFFFAOYSA-N 4-azidobutanoic acid Chemical compound OC(=O)CCCN=[N+]=[N-] WAGMYTXJRVPMGW-UHFFFAOYSA-N 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
KHKJLJHJTQRHSA-UHFFFAOYSA-N 4-methyl-4-nitropentanoic acid Chemical compound [O-][N+](=O)C(C)(C)CCC(O)=O KHKJLJHJTQRHSA-UHFFFAOYSA-N 0.000 description 1
150000000527 4-oxazolines Chemical class 0.000 description 1
NNJMFJSKMRYHSR-UHFFFAOYSA-M 4-phenylbenzoate Chemical compound C1=CC(C(=O)[O-])=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-M 0.000 description 1
125000005986 4-piperidonyl group Chemical group 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000282672 Ateles sp. Species 0.000 description 1
241000972773 Aulopiformes Species 0.000 description 1
206010003827 Autoimmune hepatitis Diseases 0.000 description 1
241000271566 Aves Species 0.000 description 1
241000157302 Bison bison athabascae Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241001118702 Border disease virus Species 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical class CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
ZRVIHIHTDPBEDE-UHFFFAOYSA-N CCOBO Chemical compound CCOBO ZRVIHIHTDPBEDE-UHFFFAOYSA-N 0.000 description 1
241000282465 Canis Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
241000282994 Cervidae Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
241000710827 Dengue virus 1 Species 0.000 description 1
208000000059 Dyspnea Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
241000713800 Feline immunodeficiency virus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
102000008857 Ferritin Human genes 0.000 description 1
108050000784 Ferritin Proteins 0.000 description 1
238000008416 Ferritin Methods 0.000 description 1
206010054261 Flavivirus infection Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102000006395 Globulins Human genes 0.000 description 1
108010044091 Globulins Proteins 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
208000031220 Hemophilia Diseases 0.000 description 1
208000009292 Hemophilia A Diseases 0.000 description 1
206010019663 Hepatic failure Diseases 0.000 description 1
206010019755 Hepatitis chronic active Diseases 0.000 description 1
206010019791 Hepatitis post transfusion Diseases 0.000 description 1
241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
241000725303 Human immunodeficiency virus Species 0.000 description 1
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
108010002350 Interleukin-2 Proteins 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-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
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-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
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241000282553 Macaca Species 0.000 description 1
241000283923 Marmota monax Species 0.000 description 1
FNJSWIPFHMKRAT-UHFFFAOYSA-N Monomethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(O)=O FNJSWIPFHMKRAT-UHFFFAOYSA-N 0.000 description 1
241001529936 Murinae Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000282339 Mustela Species 0.000 description 1
229910014299 N-Si Inorganic materials 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
206010060860 Neurological symptom Diseases 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229940099408 Oxidizing agent Drugs 0.000 description 1
GYTOXSCAOFRGPK-UHFFFAOYSA-N P(=O)(O)(O)OC(C(O)C(O)C(CCCCCCCCCCCCCCCCC)=O)C(CCCCCCCCCCCCCCCCC)=O Chemical compound P(=O)(O)(O)OC(C(O)C(O)C(CCCCCCCCCCCCCCCCC)=O)C(CCCCCCCCCCCCCCCCC)=O GYTOXSCAOFRGPK-UHFFFAOYSA-N 0.000 description 1
239000008118 PEG 6000 Substances 0.000 description 1
239000002033 PVDF binder Substances 0.000 description 1
241000282579 Pan Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
241000682990 Pegivirus A Species 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 1
102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
229920002535 Polyethylene Glycol 1500 Polymers 0.000 description 1
229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 1
229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 1
229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 1
229940123066 Polymerase inhibitor Drugs 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
CZWCKYRVOZZJNM-UHFFFAOYSA-N Prasterone sodium sulfate Natural products C1C(OS(O)(=O)=O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 CZWCKYRVOZZJNM-UHFFFAOYSA-N 0.000 description 1
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
206010038997 Retroviral infections Diseases 0.000 description 1
108010083644 Ribonucleases Proteins 0.000 description 1
102000006382 Ribonucleases Human genes 0.000 description 1
102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
241000277331 Salmonidae Species 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
CRPGUMMYQABYES-HFRGRHLUSA-N Silandrin Natural products O(C)c1c(O)ccc([C@@H]2[C@H](CO)Oc3c(O2)ccc([C@@H]2Oc4c(c(O)cc(O)c4)C(=O)C2)c3)c1 CRPGUMMYQABYES-HFRGRHLUSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000713311 Simian immunodeficiency virus Species 0.000 description 1
241000710960 Sindbis virus Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000272534 Struthio camelus Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
208000002903 Thalassemia Diseases 0.000 description 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
241000710924 Togaviridae Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
241000710959 Venezuelan equine encephalitis virus Species 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
206010058874 Viraemia Diseases 0.000 description 1
108010067390 Viral Proteins Proteins 0.000 description 1
229930003427 Vitamin E Natural products 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
208000003152 Yellow Fever Diseases 0.000 description 1
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
JBJATMLSPNOMLU-UHFFFAOYSA-N [CH2-]C(=O)C=CC(Cl)(Cl)Cl Chemical compound [CH2-]C(=O)C=CC(Cl)(Cl)Cl JBJATMLSPNOMLU-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
230000009471 action Effects 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000009798 acute exacerbation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000005585 adamantoate group Chemical group 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
OVVGHDNPYGTYIT-ROUHPGRKSA-N alpha-L-Rhap-(1->6)-D-Glcp Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 OVVGHDNPYGTYIT-ROUHPGRKSA-N 0.000 description 1
VSRVRBXGIRFARR-OUEGHFHCSA-N alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O VSRVRBXGIRFARR-OUEGHFHCSA-N 0.000 description 1
229940043377 alpha-cyclodextrin Drugs 0.000 description 1
230000001668 ameliorated effect Effects 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
125000003277 amino group Chemical group 0.000 description 1
238000007098 aminolysis reaction Methods 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000003429 antifungal agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
238000013459 approach Methods 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 description 1
VOCGSQHKPZSIKB-HXUWFJFHSA-N bavachinin Natural products C1([C@@H]2OC=3C=C(C(=CC=3C(=O)C2)CC=C(C)C)OC)=CC=C(O)C=C1 VOCGSQHKPZSIKB-HXUWFJFHSA-N 0.000 description 1
230000006399 behavior Effects 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
KVPFKMBYCSISTN-UHFFFAOYSA-N benzylsulfanylformic acid Chemical compound OC(=O)SCC1=CC=CC=C1 KVPFKMBYCSISTN-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000012472 biological sample Substances 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
GWWWNAKRFFANNF-UHFFFAOYSA-N bis(dimethylamino)phosphinic acid Chemical compound CN(C)P(O)(=O)N(C)C GWWWNAKRFFANNF-UHFFFAOYSA-N 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
241001233037 catfish Species 0.000 description 1
150000001768 cations Chemical group 0.000 description 1
UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
239000012539 chromatography resin Substances 0.000 description 1
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000006071 cream 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
150000005676 cyclic carbonates Chemical class 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
PWAPCRSSMCLZHG-UHFFFAOYSA-N cyclopentylidene Chemical group [C]1CCCC1 PWAPCRSSMCLZHG-UHFFFAOYSA-N 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 1
CZWCKYRVOZZJNM-USOAJAOKSA-N dehydroepiandrosterone sulfate Chemical compound C1[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 CZWCKYRVOZZJNM-USOAJAOKSA-N 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
229940120124 dichloroacetate Drugs 0.000 description 1
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002009 diols Chemical group 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000004252 dithioacetals Chemical class 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000036267 drug metabolism Effects 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
230000012953 feeding on blood of other organism Effects 0.000 description 1
239000011094 fiberboard Substances 0.000 description 1
230000004761 fibrosis Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000013020 final formulation Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000019688 fish Nutrition 0.000 description 1
QOLIPNRNLBQTAU-UHFFFAOYSA-N flavan Chemical class C1CC2=CC=CC=C2OC1C1=CC=CC=C1 QOLIPNRNLBQTAU-UHFFFAOYSA-N 0.000 description 1
229930003944 flavone Natural products 0.000 description 1
150000002213 flavones Chemical class 0.000 description 1
235000011949 flavones Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
229940080345 gamma-cyclodextrin Drugs 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
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 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
125000004395 glucoside group Chemical group 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229940075507 glyceryl monostearate Drugs 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
238000001631 haemodialysis Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000000322 hemodialysis Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
SSILHZFTFWOUJR-UHFFFAOYSA-M hexadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCCS([O-])(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-M 0.000 description 1
FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical class CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
IDUWTCGPAPTSFB-UHFFFAOYSA-N hexyl hydrogen sulfate Chemical compound CCCCCCOS(O)(=O)=O IDUWTCGPAPTSFB-UHFFFAOYSA-N 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000028993 immune response Effects 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical group C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
125000004926 indolenyl group Chemical group 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002664 inhalation therapy Methods 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000004936 isatinoyl group Chemical group N1(C(=O)C(=O)C2=CC=CC=C12)C(=O)* 0.000 description 1
125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
229940087875 leukine Drugs 0.000 description 1
201000002364 leukopenia Diseases 0.000 description 1
231100001022 leukopenia Toxicity 0.000 description 1
229940058352 levulinate Drugs 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
231100000835 liver failure Toxicity 0.000 description 1
208000007903 liver failure Diseases 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
210000004962 mammalian cell Anatomy 0.000 description 1
238000007726 management method Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
RMIODHQZRUFFFF-UHFFFAOYSA-M methoxyacetate Chemical compound COCC([O-])=O RMIODHQZRUFFFF-UHFFFAOYSA-M 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
NYEBKUUITGFJAK-UHFFFAOYSA-N methylsulfanylmethanethioic s-acid Chemical compound CSC(O)=S NYEBKUUITGFJAK-UHFFFAOYSA-N 0.000 description 1
QXJSNJMLOMKMMR-UHFFFAOYSA-N methylsulfanylmethoxymethyl benzoate Chemical compound CSCOCOC(=O)C1=CC=CC=C1 QXJSNJMLOMKMMR-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
239000003595 mist Substances 0.000 description 1
ZAHQPTJLOCWVPG-UHFFFAOYSA-N mitoxantrone dihydrochloride Chemical compound Cl.Cl.O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO ZAHQPTJLOCWVPG-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
150000004250 monothioacetals Chemical class 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
230000035772 mutation Effects 0.000 description 1
229940043348 myristyl alcohol Drugs 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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 1
CBKFHSNATJJWQK-UHFFFAOYSA-N n-pyridin-3-ylformamide Chemical compound O=CNC1=CC=CN=C1 CBKFHSNATJJWQK-UHFFFAOYSA-N 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000010606 normalization Methods 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
229940127073 nucleoside analogue Drugs 0.000 description 1
125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000006195 pent-4-inyl group Chemical group [H]C#CC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000004932 phenoxathinyl group Chemical group 0.000 description 1
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
DKTXXUNXVCHYDO-UHFFFAOYSA-N phenoxyborinic acid Chemical compound OBOC1=CC=CC=C1 DKTXXUNXVCHYDO-UHFFFAOYSA-N 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-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
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005547 pivalate group Chemical group 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920002981 polyvinylidene fluoride Polymers 0.000 description 1
239000010491 poppyseed oil Substances 0.000 description 1
230000002064 post-exposure prophylaxis Effects 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
235000004252 protein component Nutrition 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
230000005180 public health Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical group C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
201000005404 rubella Diseases 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
235000005713 safflower oil Nutrition 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
235000019515 salmon Nutrition 0.000 description 1
238000012216 screening Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
CRPGUMMYQABYES-DNVKUUNQSA-N silandrin Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@H](OC3=CC(=CC=C3O2)[C@H]2OC3=CC(O)=CC(O)=C3C(=O)C2)CO)=C1 CRPGUMMYQABYES-DNVKUUNQSA-N 0.000 description 1
229960004245 silymarin Drugs 0.000 description 1
235000017700 silymarin Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229960004249 sodium acetate Drugs 0.000 description 1
239000000176 sodium gluconate Substances 0.000 description 1
235000012207 sodium gluconate Nutrition 0.000 description 1
229940005574 sodium gluconate Drugs 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
229940005581 sodium lactate Drugs 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000011272 standard treatment Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
NJMMLKHXBSGMOH-UHFFFAOYSA-N sulfo octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OS(O)(=O)=O NJMMLKHXBSGMOH-UHFFFAOYSA-N 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
VUYXVWGKCKTUMF-UHFFFAOYSA-N tetratriacontaethylene glycol monomethyl ether Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO VUYXVWGKCKTUMF-UHFFFAOYSA-N 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003573 thiols Chemical group 0.000 description 1
229930192474 thiophene Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 1
229960001661 ursodiol Drugs 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000007501 viral attachment Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000001790 virustatic effect Effects 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
208000016261 weight loss Diseases 0.000 description 1
230000004580 weight loss Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1

Classifications

- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/5685—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Virology (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Diabetes (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Hematology (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

OA1200100128A 1998-11-24 1999-11-24 Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatmentof hepatitis C virus and other togaviruses. OA11716A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US10992498P	1998-11-24	1998-11-24
US12408799P	1999-03-11	1999-03-11
US12605699P	1999-03-23	1999-03-23

Publications (1)

Publication Number	Publication Date
OA11716A true OA11716A (en)	2005-01-25

Family

ID=27380740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200100128A OA11716A (en)	1998-11-24	1999-11-24	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatmentof hepatitis C virus and other togaviruses.

Country Status (14)

Country	Link
EP (1)	EP1133287A2 (id)
JP (1)	JP2002531397A (id)
KR (1)	KR20010101074A (id)
CN (1)	CN1328463A (id)
AP (1)	AP2001002181A0 (id)
AU (1)	AU775614B2 (id)
BR (1)	BR9915644A (id)
CA (1)	CA2352205A1 (id)
HK (1)	HK1042426A1 (id)
ID (1)	ID29864A (id)
IL (2)	IL142942A0 (id)
NZ (1)	NZ511721A (id)
OA (1)	OA11716A (id)
WO (1)	WO2000032177A2 (id)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6667299B1 (en)	2000-03-16	2003-12-23	Hollis-Eden Pharmaceuticals, Inc.	Pharmaceutical compositions and treatment methods
US6555523B1 (en)	1999-07-08	2003-04-29	Patrick T. Prendergast	Use of cirsiliol and derivatives to treat infections
PT1955700E (pt)	1999-09-30	2011-05-04	Harbor Biosciences Inc	Tratamento terap?utico de doen?as associadas ao receptor de androg?nios
CN1665515A (zh)	2002-07-02	2005-09-07	科塞普特治疗公司	治疗与干扰素α治疗相关的精神病的方法
EP2298315A1 (en) *	2002-08-28	2011-03-23	Harbor BioSciences, Inc.	Therapeutic treatment methods
ES2374117T3 (es) *	2007-11-15	2012-02-13	Madaus Gmbh	Componente de silibinina para el tratamiento de la hepatitis.
CN102993148B (zh) *	2011-09-13	2015-12-09	复旦大学	槲皮素衍生物或其类似物及其应用
WO2013178782A1 (en) *	2012-05-30	2013-12-05	Universidad De Zaragoza	Allosteric inhibitors of ns3 protease from hepatitis c virus
CN108003212A (zh) *	2017-12-24	2018-05-08	扬州工业职业技术学院	一种去氢表雄酮-6-葡萄糖苷衍生物及其作为抗丙型肝炎病毒药物的应用
CN110452280B (zh) *	2019-07-25	2020-11-17	中国人民解放军第二军医大学	一类四环三萜酸衍生物及其制备方法与应用
CA3193390A1 (en) *	2020-09-22	2022-03-31	Andrey Factor	Nebulizer and nebulized anti-virals

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL194728C (nl) *	1987-04-16	2003-01-07	Hollis Eden Pharmaceuticals	Farmaceutisch preparaat geschikt voor de profylaxe of therapie van een retrovirale infectie of een complicatie of gevolg daarvan.
US5837269A (en) *	1989-09-25	1998-11-17	University Of Utah Research Foundation	Vaccine compositions and method for enhancing an immune response
EP0901375A1 (en) *	1996-04-17	1999-03-17	Patrick Thomas Prendergast	Dhea combination therapy
WO1998047516A1 (en) *	1997-04-17	1998-10-29	Prendergast Patrick T	Combination therapy utilising 17-ketosteroids and interleukin inhibitors, or interleukin-10 potionally with interleukin inhibitors

1999
- 1999-11-24 EP EP99965050A patent/EP1133287A2/en not_active Withdrawn
- 1999-11-24 HK HK02102267.0A patent/HK1042426A1/zh unknown
- 1999-11-24 JP JP2000584873A patent/JP2002531397A/ja active Pending
- 1999-11-24 OA OA1200100128A patent/OA11716A/en unknown
- 1999-11-24 IL IL14294299A patent/IL142942A0/xx active IP Right Grant
- 1999-11-24 AU AU31052/00A patent/AU775614B2/en not_active Ceased
- 1999-11-24 KR KR1020017006525A patent/KR20010101074A/ko not_active Ceased
- 1999-11-24 CA CA002352205A patent/CA2352205A1/en not_active Abandoned
- 1999-11-24 BR BR9915644-0A patent/BR9915644A/pt not_active Application Discontinuation
- 1999-11-24 WO PCT/US1999/028082 patent/WO2000032177A2/en not_active Ceased
- 1999-11-24 NZ NZ511721A patent/NZ511721A/en unknown
- 1999-11-24 CN CN99813658A patent/CN1328463A/zh active Pending
- 1999-11-24 ID IDW00200101129A patent/ID29864A/id unknown
- 1999-11-24 AP APAP/P/2001/002181A patent/AP2001002181A0/en unknown
2001
- 2001-05-03 IL IL142942A patent/IL142942A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL142942A (en)	2006-08-20
EP1133287A2 (en)	2001-09-19
CN1328463A (zh)	2001-12-26
ID29864A (id)	2001-10-18
AU3105200A (en)	2000-06-19
IL142942A0 (en)	2002-04-21
WO2000032177A3 (en)	2001-03-22
BR9915644A (pt)	2001-08-07
AU775614B2 (en)	2004-08-05
WO2000032177A2 (en)	2000-06-08
JP2002531397A (ja)	2002-09-24
AP2001002181A0 (en)	2001-05-24
NZ511721A (en)	2004-07-30
HK1042426A1 (zh)	2002-08-16
KR20010101074A (ko)	2001-11-14
CA2352205A1 (en)	2000-06-08

Publication	Publication Date	Title
US8022234B2 (en)	2011-09-20	Compounds and compositions
US7947846B2 (en)	2011-05-24	15-OXA-steroid compounds
AU2008201188B2 (en)	2011-02-03	Use of certain steroids for treatment of blood cell deficiencies
US20030060425A1 (en)	2003-03-27	Immune modulation method using steroid compounds
US20030083231A1 (en)	2003-05-01	Blood cell deficiency treatment method
US20040220114A1 (en)	2004-11-04	Pharmaceutical compositions and treatment methods
US8541600B2 (en)	2013-09-24	11-aza, 11-thia and 11-oxa sterol compounds and compositions
AU2002244247A1 (en)	2003-03-13	Use of certain steroids for treatment of blood cell deficiencies
RU2295534C2 (ru)	2007-03-20	Полугидрат 16 альфа-бромо-3 бета-гидрокси-5 альфа-андростан-17-он, способ его получения, фармацевтические композиции, применение соединений
OA11716A (en)	2005-01-25	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatmentof hepatitis C virus and other togaviruses.
AU2004237812B2 (en)	2007-11-29	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatment of malaria and the treatment of African and American trypanosomiasis
EP1422234A2 (en)	2004-05-26	Immunomodulatory steroids, in particular the hemihydrate of 16.alpha.-bromoepiandrosterone
WO2000032176A2 (en)	2000-06-08	Use of 17-ketosteroids for the treatment of toxoplasmosis and cryptosporidosis
MXPA01005170A (en)	2002-07-25	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatment of hepatitis c virus and other togaviruses
ZA200103845B (en)	2002-05-13	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in treatment of toxoplasmosis and in the treatment of cryptosporidiosis.
MXPA01005166A (en)	2002-07-25	Use of 17-ketosteroid compounds and derivatives, metabolites and precursors thereof in the treatment of malaria and the treatment of african and american trypanosomiasis