SI20076A - Monociklični L-nukleozidi, analogi in uporaba od teh - Google Patents

Monociklični L-nukleozidi, analogi in uporaba od teh Download PDF

Info

Publication number: SI20076A
Authority: SI; Slovenia
Prior art keywords: lower alkyl; mmol; evaporated; solution; independently
Prior art date: 1996-10-16

Application number

SI9720065A

Other languages

English (en)

Slovenian (sl)

Inventor

Kandasamy Ramasamy

Robert Tam

Devron Averett

Original Assignee

Icn Pharmaceuticals, Inc.

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

1996-10-16

Filing date

1997-10-15

Publication date

2000-04-30

1997-10-15 Application filed by Icn Pharmaceuticals, Inc. filed Critical Icn Pharmaceuticals, Inc.

2000-04-30 Publication of SI20076A publication Critical patent/SI20076A/sl

Links

239000002777 nucleoside Substances 0.000 title claims abstract description 78
125000002950 monocyclic group Chemical group 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 117
206010028980 Neoplasm Diseases 0.000 claims abstract description 10
208000015181 infectious disease Diseases 0.000 claims abstract description 9
206010061217 Infestation Diseases 0.000 claims abstract description 7
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 79
229910052739 hydrogen Inorganic materials 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 44
150000003973 alkyl amines Chemical class 0.000 claims description 36
229910002091 carbon monoxide Inorganic materials 0.000 claims description 36
125000000623 heterocyclic group Chemical group 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 32
229910052760 oxygen Inorganic materials 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 25
235000000346 sugar Nutrition 0.000 claims description 24
125000002877 alkyl aryl group Chemical group 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 22
125000005741 alkyl alkenyl group Chemical group 0.000 claims description 20
229920002554 vinyl polymer Polymers 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
230000000694 effects Effects 0.000 claims description 14
IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000006519 CCH3 Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000006414 CCl Chemical group ClC* 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
230000001225 therapeutic effect Effects 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims description 2
208000035269 cancer or benign tumor Diseases 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
230000002757 inflammatory effect Effects 0.000 claims 1
102000004127 Cytokines Human genes 0.000 abstract description 6
108090000695 Cytokines Proteins 0.000 abstract description 6
230000002519 immonomodulatory effect Effects 0.000 abstract description 5
201000010099 disease Diseases 0.000 abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
230000004044 response Effects 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 231
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 229
239000000243 solution Substances 0.000 description 180
239000011541 reaction mixture Substances 0.000 description 124
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
239000000203 mixture Substances 0.000 description 101
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 97
235000019439 ethyl acetate Nutrition 0.000 description 93
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
239000000047 product Substances 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
239000000741 silica gel Substances 0.000 description 73
229910002027 silica gel Inorganic materials 0.000 description 73
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 70
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
238000006243 chemical reaction Methods 0.000 description 65
239000007787 solid Substances 0.000 description 59
239000012044 organic layer Substances 0.000 description 52
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 50
239000003480 eluent Substances 0.000 description 50
238000003818 flash chromatography Methods 0.000 description 50
239000012267 brine Substances 0.000 description 43
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
239000000725 suspension Substances 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
239000000706 filtrate Substances 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
229910000831 Steel Inorganic materials 0.000 description 28
238000000034 method Methods 0.000 description 28
239000010959 steel Substances 0.000 description 28
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 27
239000010410 layer Substances 0.000 description 26
239000011734 sodium Substances 0.000 description 26
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 25
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 25
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 24
125000003835 nucleoside group Chemical group 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
238000002360 preparation method Methods 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
210000004027 cell Anatomy 0.000 description 21
239000006188 syrup Substances 0.000 description 21
235000020357 syrup Nutrition 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
229910052786 argon Inorganic materials 0.000 description 20
239000003921 oil Substances 0.000 description 20
238000003786 synthesis reaction Methods 0.000 description 20
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 20
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 19
235000019441 ethanol Nutrition 0.000 description 19
229920005989 resin Polymers 0.000 description 19
239000011347 resin Substances 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000012300 argon atmosphere Substances 0.000 description 18
-1 ddl Chemical compound 0.000 description 18
VRWJZGHUCOFGPZ-UHFFFAOYSA-N 2-{[4-(4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=NNC=C1C1=CC=NC=C1 VRWJZGHUCOFGPZ-UHFFFAOYSA-N 0.000 description 17
230000015572 biosynthetic process Effects 0.000 description 17
239000006260 foam Substances 0.000 description 17
229920006395 saturated elastomer Polymers 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 16
239000012043 crude product Substances 0.000 description 16
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
229910000041 hydrogen chloride Inorganic materials 0.000 description 16
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 14
239000005457 ice water Substances 0.000 description 14
239000003795 chemical substances by application Substances 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
239000007858 starting material Substances 0.000 description 13
238000003756 stirring Methods 0.000 description 13
239000003039 volatile agent Substances 0.000 description 13
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 12
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 12
229910052921 ammonium sulfate Inorganic materials 0.000 description 12
235000011130 ammonium sulphate Nutrition 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
229960000329 ribavirin Drugs 0.000 description 12
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical class C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 11
210000001744 T-lymphocyte Anatomy 0.000 description 11
239000013078 crystal Substances 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
125000003729 nucleotide group Chemical group 0.000 description 11
239000000843 powder Substances 0.000 description 11
230000008569 process Effects 0.000 description 11
JPVQCHVLFHXNKB-UHFFFAOYSA-N 1,2,3,4,5,6-hexamethyldisiline Chemical compound CC1=C(C)[Si](C)=[Si](C)C(C)=C1C JPVQCHVLFHXNKB-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
229940127073 nucleoside analogue Drugs 0.000 description 10
239000002773 nucleotide Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
SRBFZHDQGSBBOR-SOOFDHNKSA-N D-ribopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@@H]1O SRBFZHDQGSBBOR-SOOFDHNKSA-N 0.000 description 9
240000006890 Erythroxylum coca Species 0.000 description 9
108010002350 Interleukin-2 Proteins 0.000 description 9
102000000588 Interleukin-2 Human genes 0.000 description 9
IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 9
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
235000008957 cocaer Nutrition 0.000 description 9
238000001914 filtration Methods 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
210000000987 immune system Anatomy 0.000 description 8
238000010992 reflux Methods 0.000 description 8
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
IHNHAHWGVLXCCI-CYDGBPFRSA-N [(2s,3s,4s,5r)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1O[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O IHNHAHWGVLXCCI-CYDGBPFRSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
230000001629 suppression Effects 0.000 description 7
0 *CC(C(*)C1)OC1Cl Chemical compound *CC(C(*)C1)OC1Cl 0.000 description 6
ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 6
OSKSVLBJJXQUPI-UHFFFAOYSA-N 2h-triazole-4-carboxamide Chemical compound NC(=O)C1=CNN=N1 OSKSVLBJJXQUPI-UHFFFAOYSA-N 0.000 description 6
IJUOARZYZPGODW-YSTARVQFSA-N 5-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2H-triazole-4-carboxamide Chemical compound C1([C@H](O)[C@H](O)[C@H](O1)CO)C1=C(N=NN1)C(=O)N IJUOARZYZPGODW-YSTARVQFSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
108010074328 Interferon-gamma Proteins 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 6
108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
PYMYPHUHKUWMLA-MROZADKFSA-N aldehydo-L-ribose Chemical compound OC[C@H](O)[C@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-MROZADKFSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
230000000840 anti-viral effect Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
QMPFMODFBNEYJH-UHFFFAOYSA-N methyl 1h-1,2,4-triazole-5-carboxylate Chemical compound COC(=O)C1=NC=NN1 QMPFMODFBNEYJH-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 6
229940113082 thymine Drugs 0.000 description 6
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
ZBDGHWFPLXXWRD-AZGQCCRYSA-N (2s,3r,4s,5s)-2-methoxyoxane-3,4,5-triol Chemical compound CO[C@H]1OC[C@H](O)[C@H](O)[C@H]1O ZBDGHWFPLXXWRD-AZGQCCRYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 5
102000004388 Interleukin-4 Human genes 0.000 description 5
108090000978 Interleukin-4 Proteins 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
241000700605 Viruses Species 0.000 description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 5
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 5
239000000853 adhesive Substances 0.000 description 5
230000001070 adhesive effect Effects 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
238000012512 characterization method Methods 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
239000000284 extract Substances 0.000 description 5
229960004413 flucytosine Drugs 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 5
239000000463 material Substances 0.000 description 5
150000003833 nucleoside derivatives Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 4
QGJNAHYFZALATE-UHFFFAOYSA-N 1h-pyrrole-2,4-dicarboxamide Chemical compound NC(=O)C1=CNC(C(N)=O)=C1 QGJNAHYFZALATE-UHFFFAOYSA-N 0.000 description 4
GXRMVWOTWXYCBS-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole-4-carboxylic acid Chemical compound OC(=O)C1=CNCN1 GXRMVWOTWXYCBS-UHFFFAOYSA-N 0.000 description 4
229960000549 4-dimethylaminophenol Drugs 0.000 description 4
BGADZIVOWCGKBJ-UHFFFAOYSA-N 4-oxo-3h-pyridine-3-carboxamide Chemical compound NC(=O)C1C=NC=CC1=O BGADZIVOWCGKBJ-UHFFFAOYSA-N 0.000 description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
102000008070 Interferon-gamma Human genes 0.000 description 4
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 4
DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
HNGGSWPHMZXFNN-UHFFFAOYSA-N dimethyl 2h-triazole-4,5-dicarboxylate Chemical compound COC(=O)C1=NNN=C1C(=O)OC HNGGSWPHMZXFNN-UHFFFAOYSA-N 0.000 description 4
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
229940028885 interleukin-4 Drugs 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
125000001424 substituent group Chemical class 0.000 description 4
150000008163 sugars Chemical class 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
150000003852 triazoles Chemical class 0.000 description 4
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 4
BRFDXFXMZSZPEF-UHFFFAOYSA-N 1,2,4-triazole-1-carboxylic acid Chemical compound OC(=O)N1C=NC=N1 BRFDXFXMZSZPEF-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZEVWQFWTGHFIDH-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CNC=1C(O)=O ZEVWQFWTGHFIDH-UHFFFAOYSA-N 0.000 description 3
ZVXTUAKXYXKULZ-UHFFFAOYSA-N 1h-pyrazole-3,5-dicarboxamide Chemical compound NC(=O)C=1C=C(C(N)=O)NN=1 ZVXTUAKXYXKULZ-UHFFFAOYSA-N 0.000 description 3
YDMVPJZBYSWOOP-UHFFFAOYSA-N 1h-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C=1C=C(C(O)=O)NN=1 YDMVPJZBYSWOOP-UHFFFAOYSA-N 0.000 description 3
NDGSDCLCVGQSKB-UHFFFAOYSA-N 1h-pyrazole-4,5-dicarbonitrile Chemical compound N#CC1=CNN=C1C#N NDGSDCLCVGQSKB-UHFFFAOYSA-N 0.000 description 3
NUGZBVBZIDWZAD-UHFFFAOYSA-N 1h-pyrazole-4-carbonitrile Chemical compound N#CC=1C=NNC=1 NUGZBVBZIDWZAD-UHFFFAOYSA-N 0.000 description 3
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
JTIMMNPDSZRQOR-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole-4-carboxamide Chemical compound NC(=O)C1=CNCN1 JTIMMNPDSZRQOR-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
FVRDYQYEVDDKCR-RKEPMNIXSA-N 2-[(3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC(C2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 FVRDYQYEVDDKCR-RKEPMNIXSA-N 0.000 description 3
IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 3
SSPYSWLZOPCOLO-UHFFFAOYSA-N 6-azauracil Chemical compound O=C1C=NNC(=O)N1 SSPYSWLZOPCOLO-UHFFFAOYSA-N 0.000 description 3
KHWJEUGTHXRSES-UHFFFAOYSA-N 6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-7-ol Chemical compound OC1C(OC)OCC2OC(C)(C)OC21 KHWJEUGTHXRSES-UHFFFAOYSA-N 0.000 description 3
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
PHEDXBVPIONUQT-UHFFFAOYSA-N Cocarcinogen A1 Natural products CCCCCCCCCCCCCC(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3(O)CC(CO)=CC2C2C1(OC(C)=O)C2(C)C PHEDXBVPIONUQT-UHFFFAOYSA-N 0.000 description 3
MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 3
241000700721 Hepatitis B virus Species 0.000 description 3
241000725303 Human immunodeficiency virus Species 0.000 description 3
108010002616 Interleukin-5 Proteins 0.000 description 3
102000000743 Interleukin-5 Human genes 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
102000008072 Lymphokines Human genes 0.000 description 3
108010074338 Lymphokines Proteins 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
230000000259 anti-tumor effect Effects 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
NQKKUSLBNWTXQI-UHFFFAOYSA-N diethyl 1h-imidazole-4,5-dicarboxylate Chemical compound CCOC(=O)C=1N=CNC=1C(=O)OCC NQKKUSLBNWTXQI-UHFFFAOYSA-N 0.000 description 3
KQTOKYAUJBRPST-BYBOBHAWSA-N ethyl 2-[(3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2[C@@H]([C@H](O)[C@@H](CO)O2)O)=N1 KQTOKYAUJBRPST-BYBOBHAWSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229960002949 fluorouracil Drugs 0.000 description 3
229940029575 guanosine Drugs 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
230000001965 increasing effect Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
OLQDKJGHMNCLOH-MNXVOIDGSA-N methyl 1-[(2s,3s,4s,5s)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=CN1[C@@H]1[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](COC(C)=O)O1 OLQDKJGHMNCLOH-MNXVOIDGSA-N 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
229940104230 thymidine Drugs 0.000 description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
238000005406 washing Methods 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
SJCDBQHCQSIZHN-UHFFFAOYSA-N 1,2-dihydrotriazole-3-carboxamide Chemical compound NC(=O)N1NNC=C1 SJCDBQHCQSIZHN-UHFFFAOYSA-N 0.000 description 2
LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 2
BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 2
RYQGPAMUUQAEEM-UHFFFAOYSA-N 1h-pyrrole-2,4-dicarbonitrile Chemical compound N#CC1=CNC(C#N)=C1 RYQGPAMUUQAEEM-UHFFFAOYSA-N 0.000 description 2
QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
XEDONBRPTABQFB-UHFFFAOYSA-N 4-[(2-formyl-3-hydroxyphenoxy)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=CC(O)=C1C=O XEDONBRPTABQFB-UHFFFAOYSA-N 0.000 description 2
VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 2
TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 description 2
MFEFTTYGMZOIKO-UHFFFAOYSA-N 5-azacytosine Chemical compound NC1=NC=NC(=O)N1 MFEFTTYGMZOIKO-UHFFFAOYSA-N 0.000 description 2
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 2
XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
239000002126 C01EB10 - Adenosine Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
238000008157 ELISA kit Methods 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
201000005569 Gout Diseases 0.000 description 2
241000711549 Hepacivirus C Species 0.000 description 2
241000701806 Human papillomavirus Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
102100037850 Interferon gamma Human genes 0.000 description 2
108090001005 Interleukin-6 Proteins 0.000 description 2
102000004889 Interleukin-6 Human genes 0.000 description 2
102000004890 Interleukin-8 Human genes 0.000 description 2
108090001007 Interleukin-8 Proteins 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
241000725643 Respiratory syncytial virus Species 0.000 description 2
206010057190 Respiratory tract infections Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
229960005305 adenosine Drugs 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
230000003466 anti-cipated effect Effects 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
229960002756 azacitidine Drugs 0.000 description 2
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 2
DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 description 2
238000004166 bioassay Methods 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
MHSVUSZEHNVFKW-UHFFFAOYSA-N bis-4-nitrophenyl phosphate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OP(=O)(O)OC1=CC=C([N+]([O-])=O)C=C1 MHSVUSZEHNVFKW-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
DDYAZDRFUVZBMM-UHFFFAOYSA-N chloro-[chloro-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)O[Si](Cl)(C(C)C)C(C)C DDYAZDRFUVZBMM-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 description 2
238000002648 combination therapy Methods 0.000 description 2
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
230000004069 differentiation Effects 0.000 description 2
VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
239000002024 ethyl acetate extract Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
229940044627 gamma-interferon Drugs 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000006206 glycosylation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
230000036737 immune function Effects 0.000 description 2
230000036039 immunity Effects 0.000 description 2
229960001438 immunostimulant agent Drugs 0.000 description 2
239000003022 immunostimulating agent Substances 0.000 description 2
230000003308 immunostimulating effect Effects 0.000 description 2
230000028709 inflammatory response Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229960003130 interferon gamma Drugs 0.000 description 2
XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 2
229940096397 interleukin-8 Drugs 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
PGHMRUGBZOYCAA-ADZNBVRBSA-N ionomycin Chemical compound O1[C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)/C=C/C[C@@H](C)C[C@@H](C)C(/O)=C/C(=O)[C@@H](C)C[C@@H](C)C[C@@H](CCC(O)=O)C)CC[C@@]1(C)[C@@H]1O[C@](C)([C@@H](C)O)CC1 PGHMRUGBZOYCAA-ADZNBVRBSA-N 0.000 description 2
PGHMRUGBZOYCAA-UHFFFAOYSA-N ionomycin Natural products O1C(CC(O)C(C)C(O)C(C)C=CCC(C)CC(C)C(O)=CC(=O)C(C)CC(C)CC(CCC(O)=O)C)CCC1(C)C1OC(C)(C(C)O)CC1 PGHMRUGBZOYCAA-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
ZBDGHWFPLXXWRD-UHFFFAOYSA-N methyl alpha-L-arabinopyranoside Natural products COC1OCC(O)C(O)C1O ZBDGHWFPLXXWRD-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
125000002911 monocyclic heterocycle group Chemical group 0.000 description 2
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
150000007523 nucleic acids Chemical class 0.000 description 2
102000039446 nucleic acids Human genes 0.000 description 2
108020004707 nucleic acids Proteins 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
150000002972 pentoses Chemical class 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000002212 purine nucleoside Substances 0.000 description 2
239000002718 pyrimidine nucleoside Substances 0.000 description 2
229910052711 selenium Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
230000000391 smoking effect Effects 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 2
229950009795 tucaresol Drugs 0.000 description 2
102000003390 tumor necrosis factor Human genes 0.000 description 2
DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 2
229940045145 uridine Drugs 0.000 description 2
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
OIRDTQYFTABQOQ-DEGSGYPDSA-N (2S,3S,4R,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound [C@H]1([C@@H](O)[C@@H](O)[C@@H](O1)CO)N1C2=NC=NC(=C2N=C1)N OIRDTQYFTABQOQ-DEGSGYPDSA-N 0.000 description 1
GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
DBZQFUNLCALWDY-PNHWDRBUSA-N (2r,3r,4s,5r)-2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC=CC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O DBZQFUNLCALWDY-PNHWDRBUSA-N 0.000 description 1
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
BRRCLIKFZISBBV-UHFFFAOYSA-M (4-ethoxy-2,4-dioxobutyl)-triphenylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)CC(=O)OCC)C1=CC=CC=C1 BRRCLIKFZISBBV-UHFFFAOYSA-M 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 1
UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
GUQHFZFTGHNVDG-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carbonitrile Chemical compound N#CC1=NC=NN1 GUQHFZFTGHNVDG-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
HPKQEMIXSLRGJU-UUOKFMHZSA-N 2-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-3h-purine-6,8-dione Chemical compound O=C1N(C)C(C(NC(N)=N2)=O)=C2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HPKQEMIXSLRGJU-UUOKFMHZSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
WROOSPIJWMLWLG-UHFFFAOYSA-N 2-nitro-1h-imidazole Chemical compound [O-][N+](=O)C1=NC=CN1.[O-][N+](=O)C1=NC=CN1 WROOSPIJWMLWLG-UHFFFAOYSA-N 0.000 description 1
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
YLDCUKJMEKGGFI-QCSRICIXSA-N 4-acetamidobenzoic acid;9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one;1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C.CC(O)CN(C)C.CC(O)CN(C)C.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.CC(=O)NC1=CC=C(C(O)=O)C=C1.O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(NC=NC2=O)=C2N=C1 YLDCUKJMEKGGFI-QCSRICIXSA-N 0.000 description 1
FZRGWDWDSQMLNN-UHFFFAOYSA-N 4-amino-1,2,5-selenadiazole-3-carboxylic acid Chemical compound NC1=N[se]N=C1C(O)=O FZRGWDWDSQMLNN-UHFFFAOYSA-N 0.000 description 1
OJMKAQZLZNNVTG-UHFFFAOYSA-N 4-amino-1,2,5-thiadiazole-3-carboxylic acid Chemical compound NC1=NSN=C1C(O)=O OJMKAQZLZNNVTG-UHFFFAOYSA-N 0.000 description 1
NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 1
NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
XXAMCWVPBITOGA-UHFFFAOYSA-N 5-bromo-3-nitro-1h-1,2,4-triazole Chemical compound [O-][N+](=O)C1=NNC(Br)=N1 XXAMCWVPBITOGA-UHFFFAOYSA-N 0.000 description 1
VZUHHVCEVDUQHQ-UHFFFAOYSA-N 5-methoxycarbonyl-1h-pyrazole-3-carboxylic acid Chemical compound COC(=O)C1=CC(C(O)=O)=NN1 VZUHHVCEVDUQHQ-UHFFFAOYSA-N 0.000 description 1
DMKPBSKKJZGMPL-UHFFFAOYSA-N 5-methylsulfanyl-3-oxo-1,2-thiazole-4-carbonitrile Chemical compound CSC=1SN=C(O)C=1C#N DMKPBSKKJZGMPL-UHFFFAOYSA-N 0.000 description 1
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
WYXSYVWAUAUWLD-SHUUEZRQSA-N 6-azauridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=N1 WYXSYVWAUAUWLD-SHUUEZRQSA-N 0.000 description 1
GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000007848 Bronsted acid Substances 0.000 description 1
ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 1
IDABAEPWKOIGNM-UHFFFAOYSA-N CC[Na].OC(=O)CC(=O)C(O)=O Chemical compound CC[Na].OC(=O)CC(=O)C(O)=O IDABAEPWKOIGNM-UHFFFAOYSA-N 0.000 description 1
OKUHAMOVKZDBJL-ZRUFSTJUSA-N C[Si](C)(C)C([C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)N=C(N)N=C1)O)O)(O)[Si](C)(C)C Chemical compound C[Si](C)(C)C([C@@H]1[C@H]([C@H]([C@@H](O1)N1C(=O)N=C(N)N=C1)O)O)(O)[Si](C)(C)C OKUHAMOVKZDBJL-ZRUFSTJUSA-N 0.000 description 1
SPVBDQOPTPFTJW-AAQQEJRNSA-N C[Si](C)(C)[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=N1 Chemical compound C[Si](C)(C)[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=N1 SPVBDQOPTPFTJW-AAQQEJRNSA-N 0.000 description 1
229940126639 Compound 33 Drugs 0.000 description 1
UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
AVVWPBAENSWJCB-IVMDWMLBSA-N D-glucofuranose Chemical compound OC[C@@H](O)[C@H]1OC(O)[C@H](O)[C@H]1O AVVWPBAENSWJCB-IVMDWMLBSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
206010018634 Gouty Arthritis Diseases 0.000 description 1
239000007995 HEPES buffer Substances 0.000 description 1
108010078851 HIV Reverse Transcriptase Proteins 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
206010061192 Haemorrhagic fever Diseases 0.000 description 1
108010034145 Helminth Proteins Proteins 0.000 description 1
208000005176 Hepatitis C Diseases 0.000 description 1
208000001688 Herpes Genitalis Diseases 0.000 description 1
208000000903 Herpes simplex encephalitis Diseases 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
208000029462 Immunodeficiency disease Diseases 0.000 description 1
241000712431 Influenza A virus Species 0.000 description 1
102000006992 Interferon-alpha Human genes 0.000 description 1
108010047761 Interferon-alpha Proteins 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010002352 Interleukin-1 Proteins 0.000 description 1
102000003814 Interleukin-10 Human genes 0.000 description 1
108090000174 Interleukin-10 Proteins 0.000 description 1
102000003816 Interleukin-13 Human genes 0.000 description 1
108090000176 Interleukin-13 Proteins 0.000 description 1
108010002335 Interleukin-9 Proteins 0.000 description 1
102000000585 Interleukin-9 Human genes 0.000 description 1
102000015696 Interleukins Human genes 0.000 description 1
108010063738 Interleukins Proteins 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
125000000911 L-ribofuranosyl group Chemical group [H]OC([H])([H])[C@]1([H])OC([H])(*)[C@@]([H])(O[H])[C@@]1([H])O[H] 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
201000005505 Measles Diseases 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
HPXOOLVBMCFLEP-UHFFFAOYSA-N N#Cc1c[n](C(C2)OC(CO)C2O)c(C#N)c1 Chemical compound N#Cc1c[n](C(C2)OC(CO)C2O)c(C#N)c1 HPXOOLVBMCFLEP-UHFFFAOYSA-N 0.000 description 1
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
ORCGELKXZGDXNY-UHFFFAOYSA-N NC(c1c[n](C(C2)OC(CO)C2O)c(C(N)=O)c1)=O Chemical compound NC(c1c[n](C(C2)OC(CO)C2O)c(C(N)=O)c1)=O ORCGELKXZGDXNY-UHFFFAOYSA-N 0.000 description 1
GODSJHAJEWFDAD-UHFFFAOYSA-N NC(c1n[n](C(C2)OC(CO)C2O)cn1)=O Chemical compound NC(c1n[n](C(C2)OC(CO)C2O)cn1)=O GODSJHAJEWFDAD-UHFFFAOYSA-N 0.000 description 1
NNGWMDRHRTYMPN-UHFFFAOYSA-N NC(c1ncn[n]1C(C1)OC(CO)C1O)=O Chemical compound NC(c1ncn[n]1C(C1)OC(CO)C1O)=O NNGWMDRHRTYMPN-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
241000150452 Orthohantavirus Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
241001061127 Thione Species 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
102100040247 Tumor necrosis factor Human genes 0.000 description 1
241000287433 Turdus Species 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
150000003835 adenosine derivatives Chemical class 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000013566 allergen Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000000947 anti-immunosuppressive effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
OIRDTQYFTABQOQ-UHFFFAOYSA-N ara-adenosine Natural products Nc1ncnc2n(cnc12)C1OC(CO)C(O)C1O OIRDTQYFTABQOQ-UHFFFAOYSA-N 0.000 description 1
239000002215 arabinonucleoside Substances 0.000 description 1
125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
230000001363 autoimmune Effects 0.000 description 1
AWAUBADRMJIRAK-UHFFFAOYSA-N azane;methane Chemical compound C.N AWAUBADRMJIRAK-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000002902 bimodal effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
125000003636 chemical group Chemical group 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940125878 compound 36 Drugs 0.000 description 1
229940127573 compound 38 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
229940125900 compound 59 Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 1
102000003675 cytokine receptors Human genes 0.000 description 1
108010057085 cytokine receptors Proteins 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
UVSPVEYCSVXYBB-UHFFFAOYSA-N ethyl 3-amino-3-oxopropanoate Chemical compound CCOC(=O)CC(N)=O UVSPVEYCSVXYBB-UHFFFAOYSA-N 0.000 description 1
VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
239000006261 foam material Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
201000004946 genital herpes Diseases 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000003147 glycosyl group Chemical group 0.000 description 1
230000013595 glycosylation Effects 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
244000000013 helminth Species 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000028996 humoral immune response Effects 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
238000010166 immunofluorescence Methods 0.000 description 1
238000010185 immunofluorescence analysis Methods 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000000415 inactivating effect Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
229940047122 interleukins Drugs 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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 compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960001614 levamisole Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
VFTZKSMAJVLWOV-UHFFFAOYSA-N methyl 1h-pyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NNC=1 VFTZKSMAJVLWOV-UHFFFAOYSA-N 0.000 description 1
UUTDWTOZAWFKFW-UHFFFAOYSA-N methyl 2,4-dioxo-1h-pyrimidine-6-carboxylate Chemical compound COC(=O)C1=CC(=O)NC(=O)N1 UUTDWTOZAWFKFW-UHFFFAOYSA-N 0.000 description 1
QKNWNYLBGAWVPD-UHFFFAOYSA-N methyl 5-amino-4-cyano-1h-phosphole-3-carboxylate Chemical compound COC(=O)C1=CPC(N)=C1C#N QKNWNYLBGAWVPD-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N methylsulphonylmethane Natural products CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
BUOKUWQCVSZNCF-UHFFFAOYSA-N selenadiazole Chemical compound C1=C[se]N=N1 BUOKUWQCVSZNCF-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
230000000892 thymomimetic effect Effects 0.000 description 1
239000000724 thymus hormone Substances 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000440 toxicity profile Toxicity 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
PPCJTWAURVYRFW-UHFFFAOYSA-N trimethyl-(4-methyl-6-trimethylsilyloxypyrimidin-2-yl)oxysilane Chemical compound CC1=CC(O[Si](C)(C)C)=NC(O[Si](C)(C)C)=N1 PPCJTWAURVYRFW-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 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
230000003612 virological effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Immunology (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Glass Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

SI9720065A 1996-10-16 1997-10-15 Monociklični L-nukleozidi, analogi in uporaba od teh SI20076A (sl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2858596P	1996-10-16	1996-10-16
PCT/US1997/018767 WO1998016186A2 (en)	1996-10-16	1997-10-15	Monocyclic l-nucleosides, analogs and uses thereof

Publications (1)

Publication Number	Publication Date
SI20076A true SI20076A (sl)	2000-04-30

Family

ID=21844262

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9720065A SI20076A (sl)	1996-10-16	1997-10-15	Monociklični L-nukleozidi, analogi in uporaba od teh

Country Status (25)

Country	Link
US (4)	US6130326A (cs)
EP (1)	EP1027359B9 (cs)
JP (2)	JP2002503212A (cs)
KR (1)	KR100398923B1 (cs)
CN (1)	CN1268140A (cs)
AT (2)	ATE238328T1 (cs)
AU (1)	AU738170B2 (cs)
BR (1)	BR9712527A (cs)
CA (1)	CA2267279A1 (cs)
CZ (1)	CZ120699A3 (cs)
DE (2)	DE69720811T2 (cs)
DK (2)	DK1132393T3 (cs)
ES (2)	ES2195970T3 (cs)
HU (1)	HUP0001107A3 (cs)
IL (1)	IL129126A0 (cs)
NO (1)	NO313417B1 (cs)
NZ (1)	NZ334915A (cs)
PL (1)	PL187107B1 (cs)
PT (2)	PT1027359E (cs)
RU (2)	RU2188828C2 (cs)
SI (1)	SI20076A (cs)
SK (1)	SK284054B6 (cs)
UA (1)	UA63915C2 (cs)
WO (1)	WO1998016186A2 (cs)
YU (1)	YU18799A (cs)

Families Citing this family (146)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SK284054B6 (sk)	1996-10-16	2004-08-03	Icn Pharmaceuticals, Inc.	Substituované triazolové nukleozidy, farmaceutický prostriedok s ich obsahom a ich použitie
US6033399A (en)	1997-04-09	2000-03-07	Valleylab, Inc.	Electrosurgical generator with adaptive power control
UA63956C2 (uk) *	1997-06-30	2004-02-16	Ай-Сі-Ен Фармасьютикалз, Інк.	Спосіб одержання нуклеозидів
JP4596495B2 (ja) *	1997-07-18	2010-12-08	ソニー株式会社	制御装置、制御方法、電気機器システム、電気機器システムの制御方法、および、記録媒体
US7137980B2 (en)	1998-10-23	2006-11-21	Sherwood Services Ag	Method and system for controlling output of RF medical generator
US7901400B2 (en)	1998-10-23	2011-03-08	Covidien Ag	Method and system for controlling output of RF medical generator
US20040167508A1 (en)	2002-02-11	2004-08-26	Robert Wham	Vessel sealing system
US7364577B2 (en)	2002-02-11	2008-04-29	Sherwood Services Ag	Vessel sealing system
US6407077B1 (en)	1998-11-05	2002-06-18	Emory University	β-L nucleosides for the treatment of HIV infection
CA2348470C (en)	1998-11-05	2007-06-05	Centre National De La Recherche Scientifique	Nucleosides with anti-hepatitis b virus activity
WO2000025799A1 (en) *	1998-11-05	2000-05-11	Centre National De La Recherche Scientifique	β-L-2'-DEOXY-NUCLEOSIDES FOR THE TREATMENT OF HIV INFECTION
CA2357735A1 (en) *	1999-01-29	2000-08-03	Icn Pharmaceuticals, Inc.	Modulation of immune response by ribavirin
US7084125B2 (en)	1999-03-18	2006-08-01	Exiqon A/S	Xylo-LNA analogues
ATE356824T1 (de)	1999-05-04	2007-04-15	Santaris Pharma As	L-ribo-lna analoge
US6525191B1 (en) *	1999-05-11	2003-02-25	Kanda S. Ramasamy	Conformationally constrained L-nucleosides
AU7019200A (en) *	1999-08-31	2001-03-26	Nycomed Amersham Plc	Nucleoside analogues
US6664399B1 (en) *	1999-09-02	2003-12-16	E. I. Du Pont De Nemours & Company	Triazole linked carbohydrates
US6518253B1 (en) *	1999-11-19	2003-02-11	Robert Tam	Treatment of viral infections using the L-isomer of ribavirin
CZ20022112A3 (cs) *	1999-12-23	2003-05-14	Ribapharm Inc.	Prostředky a způsoby, týkající se L-nukleosidů, L-nukleotidů, a jejich analog
US7638496B2 (en)	2000-02-15	2009-12-29	Valeant Pharmaceuticals North America	Nucleoside analogs with carboxamidine modified monocyclic base
US6455508B1 (en) *	2000-02-15	2002-09-24	Kanda S. Ramasamy	Methods for treating diseases with tirazole and pyrrolo-pyrimidine ribofuranosyl nucleosides
US6495677B1 (en)	2000-02-15	2002-12-17	Kanda S. Ramasamy	Nucleoside compounds
JP2003532643A (ja) *	2000-04-13	2003-11-05	フアーマセツト・リミテツド	肝炎ウイルス感染症を治療するための３’−または２’−ヒドロキシメチル置換ヌクレオシド誘導体
MY164523A (en) *	2000-05-23	2017-12-29	Univ Degli Studi Cagliari	Methods and compositions for treating hepatitis c virus
PL359169A1 (en)	2000-05-26	2004-08-23	Idenix (Cayman) Limited	Methods and compositions for treating flaviviruses and pestiviruses
US6815542B2 (en) *	2000-06-16	2004-11-09	Ribapharm, Inc.	Nucleoside compounds and uses thereof
CN100400101C (zh)	2000-08-17	2008-07-09	特里帕普股份公司	包含病毒唑的疫苗及其使用方法
US6858590B2 (en)	2000-08-17	2005-02-22	Tripep Ab	Vaccines containing ribavirin and methods of use thereof
US7022830B2 (en)	2000-08-17	2006-04-04	Tripep Ab	Hepatitis C virus codon optimized non-structural NS3/4A fusion gene
US6680059B2 (en)	2000-08-29	2004-01-20	Tripep Ab	Vaccines containing ribavirin and methods of use thereof
US6720000B2 (en) *	2001-03-19	2004-04-13	Three Rivers Pharmaceutical, Llc	Process for producing wet ribavirin pellets
ATE252594T1 (de) *	2001-07-30	2003-11-15	Clariant Lsm Italia Spa	Verfahren zur herstellung von ribavirin
AU2002330154A1 (en) *	2001-09-28	2003-04-07	Centre National De La Recherche Scientifique	Methods and compositions for treating hepatitis c virus using 4'-modified nucleosides
PL368550A1 (en) *	2001-11-02	2005-04-04	Sandoz Ag	Process for preparing quick dissolving, high loading ribavirin compositions
KR100411398B1 (ko) *	2001-12-06	2003-12-18	주식회사유한양행	베타-디-리보푸라노즈 유도체의 제조방법
WO2003073989A2 (en) *	2002-02-28	2003-09-12	Biota, Inc.	Nucleoside 5'-monophosphate mimics and their prodrugs
EP1501435B1 (en)	2002-05-06	2007-08-29	Covidien AG	Blood detector for controlling an esu
US6982253B2 (en)	2002-06-05	2006-01-03	Supergen, Inc.	Liquid formulation of decitabine and use of the same
KR20050035194A (ko) *	2002-06-28	2005-04-15	이데닉스 (케이만) 리미티드	플라비비리다에 감염 치료용 2'-ｃ-메틸-3'-ｏ-ｌ-발린에스테르 리보푸라노실 사이티딘
US7608600B2 (en) *	2002-06-28	2009-10-27	Idenix Pharmaceuticals, Inc.	Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections
CN101172993A (zh)	2002-06-28	2008-05-07	埃迪尼克斯(开曼)有限公司	用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷
EP1545545A4 (en) *	2002-08-01	2008-09-03	Pharmasset Inc	COMPOUNDS WITH THE BICYCLO 4.2.1 NONAN SYSTEM FOR THE TREATMENT OF FLAVIVIRIDAE / I INFECTIONS
AU2003253380A1 (en) *	2002-08-12	2004-03-11	F. Hoffmann-La-Roche Ag	Process for producing a ribofuranose
US7538094B2 (en) *	2002-09-19	2009-05-26	Three Rivers Pharmacueticals, Llc	Composition containing ribavirin and use thereof
US20040077607A1 (en) *	2002-10-21	2004-04-22	Uckun Fatih M.	Aryl phosphate derivatives of d4T with potent anti-viral activity against hemorrhagic fever viruses
NZ540098A (en)	2002-10-29	2008-09-26	Coley Pharmaceutical Group Ltd	Use of CPG oligonucleotides in the treatment of hepatitis C virus infection
AU2003298658A1 (en)	2002-11-15	2004-06-15	Idenix (Cayman) Limited	2'-branched nucleosides and flaviviridae mutation
TWI294882B (en) *	2002-12-09	2008-03-21	Hoffmann La Roche	Anhydrous crystalline azido cytosine hemisulfate derivative
US7255694B2 (en)	2002-12-10	2007-08-14	Sherwood Services Ag	Variable output crest factor electrosurgical generator
US7044948B2 (en)	2002-12-10	2006-05-16	Sherwood Services Ag	Circuit for controlling arc energy from an electrosurgical generator
US7598373B2 (en) *	2002-12-12	2009-10-06	Idenix Pharmaceuticals, Inc.	Process for the production of 2-C-methyl-D-ribonolactone
MXPA05006865A (es) *	2002-12-23	2005-12-12	Idenix Cayman Ltd	Proceso para la produccion de profarmacos 3'-nucleosidos.
US6943249B2 (en) *	2003-03-17	2005-09-13	Ash Stevens, Inc.	Methods for isolating crystalline Form I of 5-azacytidine
US6887855B2 (en)	2003-03-17	2005-05-03	Pharmion Corporation	Forms of 5-azacytidine
US7038038B2 (en) *	2003-03-17	2006-05-02	Pharmion Corporation	Synthesis of 5-azacytidine
JP2006524227A (ja) *	2003-03-28	2006-10-26	ファーマセット，インク．	フラビウイルス科ウイルス感染の治療のための化合物
WO2004098385A2 (en)	2003-05-01	2004-11-18	Sherwood Services Ag	Method and system for programing and controlling an electrosurgical generator system
RU2358979C2 (ru)	2003-05-30	2009-06-20	Фармассет, Инк.	Модифицированные фторированные аналоги нуклеозида
US20050009848A1 (en) *	2003-07-10	2005-01-13	Icn Pharmaceuticals Switzerland Ltd.	Use of antivirals against inflammatory bowel diseases
US6930093B2 (en) *	2003-07-10	2005-08-16	Valeant Research & Development	Use of ribofuranose derivatives against inflammatory bowel diseases
ATE478886T1 (de)	2003-07-25	2010-09-15	Idenix Pharmaceuticals Inc	Purin nucleoside für die behandlung von durch flavividrae verursachten krankheiten, einschliesslich hepatitis c
WO2005018330A1 (en) *	2003-08-18	2005-03-03	Pharmasset, Inc.	Dosing regimen for flaviviridae therapy
RU2264409C2 (ru) *	2003-10-01	2005-11-20	Государственный научный центр вирусологии и биотехнологии "Вектор" (ГНЦ ВБ "Вектор")	2`-амино-2`-дезоксинуклеозиды - ингибиторы репродукции вирусов кори и марбург
US8104956B2 (en)	2003-10-23	2012-01-31	Covidien Ag	Thermocouple measurement circuit
CA2542849C (en)	2003-10-23	2013-08-20	Sherwood Services Ag	Redundant temperature monitoring in electrosurgical systems for safety mitigation
US7396336B2 (en)	2003-10-30	2008-07-08	Sherwood Services Ag	Switched resonant ultrasonic power amplifier system
US7131860B2 (en)	2003-11-20	2006-11-07	Sherwood Services Ag	Connector systems for electrosurgical generator
US7300435B2 (en)	2003-11-21	2007-11-27	Sherwood Services Ag	Automatic control system for an electrosurgical generator
US7766905B2 (en)	2004-02-12	2010-08-03	Covidien Ag	Method and system for continuity testing of medical electrodes
US20050182252A1 (en)	2004-02-13	2005-08-18	Reddy K. R.	Novel 2'-C-methyl nucleoside derivatives
US7780662B2 (en)	2004-03-02	2010-08-24	Covidien Ag	Vessel sealing system using capacitive RF dielectric heating
US20060040944A1 (en) *	2004-06-23	2006-02-23	Gilles Gosselin	5-Aza-7-deazapurine derivatives for treating Flaviviridae
CN101023094B (zh)	2004-07-21	2011-05-18	法莫赛特股份有限公司	烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备
ES2725457T3 (es)	2004-09-14	2019-09-24	Gilead Pharmasset Llc	Preparación de ribofuranosil pirimidinas y purinas 2'fluoro-2'-alquil-sustituidas u otras opcionalmente sustituidas y sus derivados
US7628786B2 (en)	2004-10-13	2009-12-08	Covidien Ag	Universal foot switch contact port
US7687473B2 (en) *	2005-01-07	2010-03-30	Health Research, Inc.	5-amino-4-imidazolecarboxamide riboside and its nucleobase as potentiators of antifolate transport and metabolism
US7250416B2 (en)	2005-03-11	2007-07-31	Supergen, Inc.	Azacytosine analogs and derivatives
JP4516863B2 (ja) *	2005-03-11	2010-08-04	株式会社ケンウッド	音声合成装置、音声合成方法及びプログラム
EP2805719A1 (en) *	2005-03-30	2014-11-26	Glaxosmithkline LLC	Nicotinamide riboside and analogues thereof
US20070014833A1 (en) *	2005-03-30	2007-01-18	Sirtris Pharmaceuticals, Inc.	Treatment of eye disorders with sirtuin modulators
EP1888751A2 (en) *	2005-05-25	2008-02-20	Tripep Ab	A hepatitis c virus non-structural ns3/4a fusion gene
US20060292099A1 (en) *	2005-05-25	2006-12-28	Michael Milburn	Treatment of eye disorders with sirtuin modulators
US7700567B2 (en)	2005-09-29	2010-04-20	Supergen, Inc.	Oligonucleotide analogues incorporating 5-aza-cytosine therein
US8734438B2 (en)	2005-10-21	2014-05-27	Covidien Ag	Circuit and method for reducing stored energy in an electrosurgical generator
US7947039B2 (en)	2005-12-12	2011-05-24	Covidien Ag	Laparoscopic apparatus for performing electrosurgical procedures
US7781576B2 (en)	2005-12-23	2010-08-24	Idenix Pharmaceuticals, Inc.	Process for preparing a synthetic intermediate for preparation of branched nucleosides
US7513896B2 (en)	2006-01-24	2009-04-07	Covidien Ag	Dual synchro-resonant electrosurgical apparatus with bi-directional magnetic coupling
US7651493B2 (en)	2006-03-03	2010-01-26	Covidien Ag	System and method for controlling electrosurgical snares
AU2007222135B2 (en) *	2006-03-09	2012-02-02	Om Pharma	Immunomodulatory compounds and treatment of diseases related to an overproduction of inflammatory cytokines
FR2907786B1 (fr) *	2006-10-27	2009-09-18	Univ Grenoble 1	Thionucleosides et applications pharmaceutiques
US20100129317A1 (en) *	2006-09-11	2010-05-27	Southern Research Institute	Azole nucleosides and use as inhibitors of rna and dna viral polymerases
CN101595117B (zh)	2006-12-08	2014-01-22	株式会社Api	呋喃糖衍生物的制造方法
WO2008086341A1 (en) *	2007-01-09	2008-07-17	Pericor Therapeutics, Inc.	Methods. compositions, and formulations for preventing or reducing adverse effects in a patient
US7964580B2 (en)	2007-03-30	2011-06-21	Pharmasset, Inc.	Nucleoside phosphoramidate prodrugs
WO2009022236A2 (en)	2007-08-16	2009-02-19	Tripep Ab	Immunogen platform
ES2824261T3 (es)	2007-09-14	2021-05-11	Biogen Ma Inc	Composiciones y procedimientos para el tratamiento de la leucoencefalopatía multifocal progresiva (LMP)
US8227431B2 (en)	2008-03-17	2012-07-24	Hetero Drugs Limited	Nucleoside derivatives
WO2009130588A2 (en) *	2008-04-22	2009-10-29	Tripep Ab	Immunogen platform
DK3782612T3 (da)	2008-05-15	2024-01-15	Celgene Corp	Orale formuleringer af cytidinanaloger og fremgangsmåder til anvendelse deraf
US8173621B2 (en)	2008-06-11	2012-05-08	Gilead Pharmasset Llc	Nucleoside cyclicphosphates
CL2009002206A1 (es)	2008-12-23	2011-08-26	Gilead Pharmasset Llc	Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales.
MX2011006890A (es)	2008-12-23	2011-07-20	Pharmasset Inc	Analogos de nucleosidos.
AR074897A1 (es)	2008-12-23	2011-02-23	Pharmasset Inc	Fosforamidatos de nucleosidos
WO2010108140A1 (en) *	2009-03-20	2010-09-23	Alios Biopharma, Inc.	Substituted nucleoside and nucleotide analogs
TWI576352B (zh)	2009-05-20	2017-04-01	基利法瑪席特有限責任公司	核苷磷醯胺
US8618076B2 (en)	2009-05-20	2013-12-31	Gilead Pharmasset Llc	Nucleoside phosphoramidates
AP2012006535A0 (en)	2010-03-31	2012-10-31	Gilead Pharmasset Llc	Stereoselective synthesis of phosphorous containing actives
PL3290428T3 (pl)	2010-03-31	2022-02-07	Gilead Pharmasset Llc	Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu
WO2012040127A1 (en)	2010-09-22	2012-03-29	Alios Biopharma, Inc.	Substituted nucleotide analogs
AU2011305652B2 (en)	2010-09-22	2016-10-20	Janssen Biopharma, Inc.	Azido nucleosides and nucleotide analogs
ES2716158T3 (es)	2010-11-30	2019-06-10	Gilead Pharmasset Llc	2'-spiro-nucleótidos para el tratamiento de hepatitis C
GB201021867D0 (en) *	2010-12-23	2011-02-02	Mologen Ag	Non-coding immunomodulatory DNA construct
CN102153548B (zh) *	2011-02-24	2012-11-28	河北大学	一种含有噻唑（嗪）烷酮环的类核苷衍生物及其制备方法和其在药物制剂中的应用
WO2012135405A1 (en) *	2011-03-31	2012-10-04	Pharmion Llc	Systhesis of 5-azacytidine
HUE042327T2 (hu)	2011-08-30	2019-06-28	Astex Pharmaceuticals Inc	Decitabin-származék készítmények
HRP20180237T4 (hr)	2011-09-16	2020-12-11	Gilead Pharmasset Llc	Metode za liječenje hcv-a
US8889159B2 (en)	2011-11-29	2014-11-18	Gilead Pharmasset Llc	Compositions and methods for treating hepatitis C virus
EP2794630A4 (en)	2011-12-22	2015-04-01	Alios Biopharma Inc	SUBSTITUTED PHOSPHORTHIOAT NUCLEOTIDE ANALOGUE
KR102072041B1 (ko)	2011-12-22	2020-01-31	앨리오스 바이오파마 인크.	치환된 뉴클레오사이드, 뉴클레오타이드 및 그의 유사체
USRE48171E1 (en)	2012-03-21	2020-08-25	Janssen Biopharma, Inc.	Substituted nucleosides, nucleotides and analogs thereof
NZ631601A (en)	2012-03-21	2016-06-24	Alios Biopharma Inc	Solid forms of a thiophosphoramidate nucleotide prodrug
US9441007B2 (en)	2012-03-21	2016-09-13	Alios Biopharma, Inc.	Substituted nucleosides, nucleotides and analogs thereof
NZ630805A (en)	2012-03-22	2016-01-29	Alios Biopharma Inc	Pharmaceutical combinations comprising a thionucleotide analog
PT2861611T (pt)	2012-05-25	2016-10-11	Janssen Sciences Ireland Uc	Nucleósidos de espirooxetano de uracilo
US9243022B2 (en)	2012-12-21	2016-01-26	Alios Biopharma, Inc.	Substituted nucleosides, nucleotides and analogs thereof
EP2950786B1 (en)	2013-01-31	2019-11-27	Gilead Pharmasset LLC	Combination formulation of two antiviral compounds
AU2014250762A1 (en)	2013-04-12	2015-10-29	Achillion Pharmaceuticals, Inc.	Highly active nucleoside derivative for the treatment of HCV
EA201690473A1 (ru)	2013-08-27	2017-03-31	ГАЙЛИД ФАРМАССЕТ ЭлЭлСи	Комбинированный состав двух противовирусных соединений
CN105829333A (zh)	2013-10-11	2016-08-03	艾丽奥斯生物制药有限公司	取代的核苷、核苷酸及其类似物
JP6670244B2 (ja)	2014-01-07	2020-03-18	バビタアグラワル	免疫調節組成物及びその使用法
EP3623364A1 (en)	2014-02-13	2020-03-18	Ligand Pharmaceuticals, Inc.	Prodrug compounds and their uses
RU2016149767A (ru)	2014-06-06	2018-07-16	Глэксосмитклайн Интеллекчуал Проперти (Но.2) Лимитед	Аналоги никотинамидрибозида и фармацевтические композиции и их применение
CN106687118A (zh)	2014-07-02	2017-05-17	配体药物公司	前药化合物及其用途
ES3029413T3 (en)	2015-04-02	2025-06-24	Ablynx Nv	Bispecific cxcr4-cd-4 polypeptides with potent anti-hiv activity
WO2017004538A1 (en)	2015-07-02	2017-01-05	Otsuka Pharmaceutical Co., Ltd.	Lyophilized pharmaceutical compositions
LU92821B1 (en)	2015-09-09	2017-03-20	Mologen Ag	Combination comprising immunostimulatory oligonucleotides
GB2542425A (en)	2015-09-21	2017-03-22	Mologen Ag	Means for the treatment of HIV
WO2017218580A1 (en)	2016-06-14	2017-12-21	Rejuvenation Therapeutics Corporation	Synthetic methods for the preparation of nicotinamide riboside and related compounds
WO2018009623A1 (en)	2016-07-08	2018-01-11	Atea Pharmaceuticals, Inc.	β-D-2'-DEOXY-2'-SUBSTITUTED-4'-SUBSTITUTED-2-SUBSTITUTED-N6-SUBSTITUTED-6-AMINOPURINE NUCLEOTIDES FOR THE TREATMENT OF PARAMYXOVIRUS AND ORTHOMYXOVIRUS INFECTIONS
RU2624018C2 (ru) *	2016-09-26	2017-06-30	Федеральное государственное бюджетное учреждение науки Институт биоорганической химии им. академиков М.М. Шемякина и Ю.А. Овчинникова РАН (ИБХ РАН)	Амид 5-(тетрагидрофуран-2-ил)-1,2,4-триазол-3-карбоновой кислоты, обладающий противовирусной активностью, и способ его получения
BR112020002280A2 (pt)	2017-08-03	2020-07-28	Otsuka Pharmaceutical Co., Ltd.	composto farmacológico e métodos purificação do mesmo
WO2019139919A1 (en)	2018-01-09	2019-07-18	Ligand Pharmaceuticals, Inc.	Acetal compounds and therapeutic uses thereof
AU2020215175A1 (en) *	2019-02-01	2021-07-29	Janssen Biopharma, Inc.	Antiviral nucleosides and derivatives thereof
PH12022551379A1 (en)	2019-12-06	2023-05-03	Vertex Pharma	Substituted tetrahydrofurans as modulators of sodium channels
SI4347031T1 (sl)	2021-06-04	2026-01-30	Vertex Pharmaceuticals Incorporated	N-(hidroksialkil (hetero)aril) tetrahidrofuran karboksamidi kot modulatorji natrijevih kanalčkov
WO2023288047A2 (en) *	2021-07-15	2023-01-19	Alnylam Pharmaceuticals, Inc.	Multiplexing targeting ligands through click chemistry at the anomeric site of sugars

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3948885A (en) *	1973-03-19	1976-04-06	Icn Pharmaceuticals, Inc.	5-Hydroxyl-1,2,3-triazole-4-carboxamide nucleoside
US4138547A (en) *	1977-12-22	1979-02-06	Icn Pharmaceuticals, Inc.	Process for preparing 1,2,4-triazole nucleosides
EP0054432B1 (en) *	1980-12-15	1990-01-31	Viratek, Inc.	Use of 2-beta-d-ribofuranosylthiazole-4-carboxamides for the manufacture of medicaments inhibiting malignant tumors
JPS60193997A (ja) *	1984-03-14	1985-10-02	Sumitomo Chem Co Ltd	新規シアノイミダゾ−ルリボヌクレオシド誘導体およびその製造法
US5041426A (en) *	1987-12-21	1991-08-20	Brigham Young University	Immune system enhancing 3-β-d-ribofuranosylthiazolo[4,5-d]pyridimine nucleosides and nucleotides
EP0331080A3 (en) *	1988-02-29	1990-11-22	Yamasa Shoyu Kabushiki Kaisha	Imidazole derivatives, process for production thereof, and use thereof
US5082829A (en) *	1989-01-24	1992-01-21	Gensia Pharmaceuticals	AICA riboside prodrugs
US4992426A (en) *	1989-02-27	1991-02-12	Nucleic Acid Research Institute	Antiparasitic 5'-sulfamoyl nucleosides
IT1246983B (it) *	1990-11-13	1994-12-12	Consiglio Nazionale Ricerche	L-2'-desossiuridine e composizioni farmaceutiche che le contengono.
US5248776A (en) *	1990-12-05	1993-09-28	University Of Georgia Research Foundation, Inc.	Process for enantiomerically pure β-L-1,3-oxathiolane nucleosides
US5438131A (en) *	1992-09-16	1995-08-01	Bergstrom; Donald E.	3-nitropyrrole nucleoside
WO1994021658A1 (en) *	1993-03-15	1994-09-29	Kalman Thomas I	Antiviral imidazolinone nucleoside derivatives
TW374087B (en) *	1993-05-25	1999-11-11	Univ Yale	L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents
US5627160A (en) *	1993-05-25	1997-05-06	Yale University	L-2',3'-dideoxy nucleoside analogs as anti-hepatitis B (HBV) and anti-HIV agents
US5567689A (en) *	1993-08-13	1996-10-22	The Uab Research Foundation	Methods for increasing uridine levels with L-nucleosides
US5599796A (en) *	1993-12-02	1997-02-04	Emory University	Treatment of urogenital cancer with boron neutron capture therapy
US5587362A (en) *	1994-01-28	1996-12-24	Univ. Of Ga Research Foundation	L-nucleosides
DE19518216A1 (de) *	1994-10-07	1996-04-11	Max Delbrueck Centrum	Neue ß-L-Nucleoside und ihre Verwendung
US5559101A (en) *	1994-10-24	1996-09-24	Genencor International, Inc.	L-ribofuranosyl nucleosides
US5672594A (en) *	1994-10-24	1997-09-30	Genencor International, Inc.	L-erythrosyl nucleosides
IT1281498B1 (it) *	1995-06-07	1998-02-18	Sardinian Antiviral Research C	Pirazolo - derivati ad attivita' antitumorale, processo per la loro preparazione e composizioni farmaceutiche che li contengono , e
SK284054B6 (sk) *	1996-10-16	2004-08-03	Icn Pharmaceuticals, Inc.	Substituované triazolové nukleozidy, farmaceutický prostriedok s ich obsahom a ich použitie

1997
- 1997-10-15 SK SK471-99A patent/SK284054B6/sk unknown
- 1997-10-15 EP EP97912762A patent/EP1027359B9/en not_active Expired - Lifetime
- 1997-10-15 IL IL12912697A patent/IL129126A0/xx unknown
- 1997-10-15 JP JP51861298A patent/JP2002503212A/ja active Pending
- 1997-10-15 AT AT97912762T patent/ATE238328T1/de not_active IP Right Cessation
- 1997-10-15 NZ NZ334915A patent/NZ334915A/xx unknown
- 1997-10-15 WO PCT/US1997/018767 patent/WO1998016186A2/en not_active Ceased
- 1997-10-15 CZ CZ991206A patent/CZ120699A3/cs unknown
- 1997-10-15 BR BR9712527-0A patent/BR9712527A/pt not_active Application Discontinuation
- 1997-10-15 UA UA99042175A patent/UA63915C2/uk unknown
- 1997-10-15 CN CN97180619A patent/CN1268140A/zh active Pending
- 1997-10-15 HU HU0001107A patent/HUP0001107A3/hu unknown
- 1997-10-15 DK DK01108303T patent/DK1132393T3/da active
- 1997-10-15 DK DK97912762T patent/DK1027359T3/da active
- 1997-10-15 DE DE69720811T patent/DE69720811T2/de not_active Expired - Fee Related
- 1997-10-15 AT AT01108303T patent/ATE236921T1/de not_active IP Right Cessation
- 1997-10-15 PT PT97912762T patent/PT1027359E/pt unknown
- 1997-10-15 AU AU49867/97A patent/AU738170B2/en not_active Ceased
- 1997-10-15 CA CA002267279A patent/CA2267279A1/en not_active Abandoned
- 1997-10-15 DE DE69721339T patent/DE69721339T2/de not_active Expired - Fee Related
- 1997-10-15 KR KR10-1999-7003326A patent/KR100398923B1/ko not_active Expired - Fee Related
- 1997-10-15 ES ES01108303T patent/ES2195970T3/es not_active Expired - Lifetime
- 1997-10-15 PL PL97333419A patent/PL187107B1/pl not_active IP Right Cessation
- 1997-10-15 RU RU99109459/04A patent/RU2188828C2/ru active
- 1997-10-15 SI SI9720065A patent/SI20076A/sl not_active IP Right Cessation
- 1997-10-15 PT PT01108303T patent/PT1132393E/pt unknown
- 1997-10-15 ES ES97912762T patent/ES2195125T3/es not_active Expired - Lifetime
1999
- 1999-04-14 US US09/291,903 patent/US6130326A/en not_active Expired - Fee Related
- 1999-04-15 NO NO19991785A patent/NO313417B1/no not_active IP Right Cessation
- 1999-04-15 YU YU18799A patent/YU18799A/sh unknown
2000
- 2000-08-07 US US09/633,493 patent/US6552183B1/en not_active Expired - Lifetime
2001
- 2001-12-03 RU RU2001132536/04A patent/RU2001132536A/ru not_active Application Discontinuation
- 2001-12-31 US US09/969,355 patent/US6573248B2/en not_active Expired - Lifetime
2002
- 2002-04-09 US US10/120,101 patent/US6642206B2/en not_active Expired - Lifetime
- 2002-10-31 JP JP2002318773A patent/JP2003176296A/ja active Pending

Also Published As

Publication number	Publication date
CZ120699A3 (cs)	1999-09-15
DE69721339T2 (de)	2004-01-22
NO313417B1 (no)	2002-09-30
DE69721339D1 (de)	2003-05-28
HUP0001107A3 (en)	2003-01-28
DE69720811D1 (de)	2003-05-15
DK1132393T3 (da)	2003-07-21
ES2195970T3 (es)	2003-12-16
NO991785D0 (no)	1999-04-15
NO991785L (no)	1999-06-15
PL187107B1 (pl)	2004-05-31
EP1027359B9 (en)	2003-09-17
US6552183B1 (en)	2003-04-22
IL129126A0 (en)	2000-02-17
ATE238328T1 (de)	2003-05-15
NZ334915A (en)	2000-11-24
SK47199A3 (en)	2000-12-11
PT1027359E (pt)	2003-09-30
RU2001132536A (ru)	2003-08-20
SK284054B6 (sk)	2004-08-03
US20030018186A1 (en)	2003-01-23
EP1027359B1 (en)	2003-04-23
YU18799A (sh)	2002-06-19
CA2267279A1 (en)	1998-04-23
HK1028977A1 (en)	2001-03-16
AU738170B2 (en)	2001-09-13
JP2003176296A (ja)	2003-06-24
EP1027359A2 (en)	2000-08-16
EP1027359A4 (en)	2001-07-25
PL333419A1 (en)	1999-12-06
JP2002503212A (ja)	2002-01-29
US20020095033A1 (en)	2002-07-18
KR20000049224A (ko)	2000-07-25
HK1038365A1 (en)	2002-03-15
ES2195125T3 (es)	2003-12-01
US6573248B2 (en)	2003-06-03
US6642206B2 (en)	2003-11-04
WO1998016186A3 (en)	1998-06-11
DE69720811T2 (de)	2004-03-11
US6130326A (en)	2000-10-10
DK1027359T3 (da)	2003-08-11
HUP0001107A2 (hu)	2001-06-28
CN1268140A (zh)	2000-09-27
PT1132393E (pt)	2003-08-29
KR100398923B1 (ko)	2003-09-19
ATE236921T1 (de)	2003-04-15
UA63915C2 (uk)	2004-02-16
RU2188828C2 (ru)	2002-09-10
BR9712527A (pt)	2000-03-08
AU4986797A (en)	1998-05-11
WO1998016186A2 (en)	1998-04-23

Legal Events

Date	Code	Title	Description
2005-01-10	IF	Valid on the event date
2005-10-31	KO00	Lapse of patent	Effective date: 20050722

Publication	Publication Date	Title
US6130326A (en)	2000-10-10	Monocyclic L-Nucleosides, analogs and uses thereof
EP1928475B1 (en)	2018-05-23	Antiviral phosphoramidates of 4'-c-azido-substituted pronucleotides
EP1058686B1 (en)	2006-11-02	2'-fluoronucleosides
EP1296995A2 (en)	2003-04-02	3'-prodrugs of 2'-deoxy-beta-l-nucleosides
AU2001266927A1 (en)	2002-03-14	3'-prodrugs of 2'-deoxy-beta-L-nucleosides
JP3142874B2 (ja)	2001-03-07	３´−置換ヌクレオシド誘導体
WO2003062255A2 (en)	2003-07-31	Sugar modified nucleosides as viral replication inhibitors
EP0296573B1 (en)	1994-01-12	Novel nucleosides, their preparation and pharmaceutical compositions
BG108000A (bg)	2004-08-31	Н"кл...озидни производни, използвани ка'о инхиби'ори на зави'има о' рнк, рнк вир"'на полим...раза
EP1302474A1 (en)	2003-04-16	Monocyclic L-nucleosides, analogs and uses thereof
MXPA99003434A (en)	2000-07-01	Monocyclic l-nucleosides, analogs and uses thereof
HK1050901A (en)	2003-07-11	Monocyclic l-nucleosides, analogs and uses thereof
HRP990147A2 (en)	2001-02-28	Monocyclic l-nucleosides, analogs and uses thereof
HK1053841A (en)	2003-11-07	Monocyclic l-nucleosides, analogs and uses thereof
HK1028977B (en)	2003-09-26	Monocyclic l-nucleosides, analogs and uses thereof
WO2006122207A1 (en)	2006-11-16	6-hydrazinopurine 2'-methyl ribonucleosides and nucleotides for treatment of hcv
HK1038365B (en)	2003-08-29	L-ribavirin and uses thereof
HK1029998A (en)	2001-04-20	Monocyclic l-nucleosides, analogs and uses thereof