NO822712L - Nye derivater av guanin. - Google Patents
Nye derivater av guanin.Info
- Publication number
- NO822712L NO822712L NO822712A NO822712A NO822712L NO 822712 L NO822712 L NO 822712L NO 822712 A NO822712 A NO 822712A NO 822712 A NO822712 A NO 822712A NO 822712 L NO822712 L NO 822712L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- hydroxy
- groups
- hydrogen
- Prior art date
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 238000000034 method Methods 0.000 claims abstract description 131
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 230000009385 viral infection Effects 0.000 claims abstract description 6
- 230000007062 hydrolysis Effects 0.000 claims description 35
- 238000006460 hydrolysis reaction Methods 0.000 claims description 35
- 239000000460 chlorine Substances 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 19
- -1 cyclic carbonate ester Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 241001529453 unidentified herpesvirus Species 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- QOVUZUCXPAZXDZ-UHFFFAOYSA-N 2-amino-9-(3,4-dihydroxybutyl)-3h-purin-6-one Chemical group N1C(N)=NC(=O)C2=C1N(CCC(O)CO)C=N2 QOVUZUCXPAZXDZ-UHFFFAOYSA-N 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- BOVGCIHOTQTZKJ-UHFFFAOYSA-N 2-amino-9-(2,4-dihydroxybutyl)-3h-purin-6-one Chemical group N1C(N)=NC(=O)C2=C1N(CC(O)CCO)C=N2 BOVGCIHOTQTZKJ-UHFFFAOYSA-N 0.000 claims description 4
- YIPVUMLDHIUDAJ-UHFFFAOYSA-N 2-amino-9-(3-fluoro-4-hydroxybutyl)-3h-purin-6-one Chemical group O=C1NC(N)=NC2=C1N=CN2CCC(F)CO YIPVUMLDHIUDAJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000003682 fluorination reaction Methods 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- AULIMVGVNBKKDP-UHFFFAOYSA-N 2-amino-9-(2,3,4-trihydroxybutyl)-3h-purin-6-one Chemical group O=C1NC(N)=NC2=C1N=CN2CC(O)C(O)CO AULIMVGVNBKKDP-UHFFFAOYSA-N 0.000 claims description 2
- OPCRDORBRKLDFT-UHFFFAOYSA-N 2-amino-9-(2,3-difluoro-4-hydroxybutyl)-3h-purin-6-one Chemical group O=C1NC(N)=NC2=C1N=CN2CC(F)C(F)CO OPCRDORBRKLDFT-UHFFFAOYSA-N 0.000 claims description 2
- MBIFPLWWTFPPET-UHFFFAOYSA-N 2-amino-9-(2-fluoro-4-hydroxybutyl)-3h-purin-6-one Chemical group O=C1NC(N)=NC2=C1N=CN2CC(F)CCO MBIFPLWWTFPPET-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 235000019000 fluorine Nutrition 0.000 claims 9
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 claims 2
- ZOLACKDSSUBCNN-UHFFFAOYSA-N 5,6-dimethylcyclohexa-2,4-diene-1-carboxylic acid Chemical class CC1C(C(O)=O)C=CC=C1C ZOLACKDSSUBCNN-UHFFFAOYSA-N 0.000 claims 1
- 244000028178 Marasmius oreades Species 0.000 claims 1
- 230000009089 cytolysis Effects 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 32
- 241000700605 Viruses Species 0.000 abstract description 27
- 201000010099 disease Diseases 0.000 abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 14
- 230000000840 anti-viral effect Effects 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 206010028980 Neoplasm Diseases 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003826 tablet Substances 0.000 description 11
- 239000013543 active substance Substances 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 230000006870 function Effects 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002674 ointment Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- 230000003612 virological effect Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000001613 neoplastic effect Effects 0.000 description 6
- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 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 5
- 239000002253 acid Substances 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000003443 antiviral agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003889 eye drop Substances 0.000 description 4
- 229940012356 eye drops Drugs 0.000 description 4
- 238000005805 hydroxylation reaction Methods 0.000 description 4
- 206010023332 keratitis Diseases 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QSGGLAGTJDEIAN-UHFFFAOYSA-N 3-fluorooxolan-2-one Chemical compound FC1CCOC1=O QSGGLAGTJDEIAN-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000007514 Herpes zoster Diseases 0.000 description 3
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 3
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001540 azides Chemical group 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 230000007541 cellular toxicity Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QOVUZUCXPAZXDZ-YFKPBYRVSA-N 2-amino-9-[(3s)-3,4-dihydroxybutyl]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(CC[C@H](O)CO)C=N2 QOVUZUCXPAZXDZ-YFKPBYRVSA-N 0.000 description 2
- BDZHKUAKSMWSAJ-UHFFFAOYSA-N 2-chloro-n,n-diethyl-1,1,2-trifluoroethanamine Chemical compound CCN(CC)C(F)(F)C(F)Cl BDZHKUAKSMWSAJ-UHFFFAOYSA-N 0.000 description 2
- WKXIWQVKQZNQKK-UHFFFAOYSA-N 4-(2-amino-6-chloropurin-9-yl)-2-fluorobutan-1-ol Chemical compound NC1=NC(Cl)=C2N=CN(CCC(F)CO)C2=N1 WKXIWQVKQZNQKK-UHFFFAOYSA-N 0.000 description 2
- CMGRSRISJNVRFI-UHFFFAOYSA-N 4-(2-amino-6-oxo-3h-purin-9-yl)-2-hydroxybutanoic acid Chemical compound O=C1NC(N)=NC2=C1N=CN2CCC(O)C(O)=O CMGRSRISJNVRFI-UHFFFAOYSA-N 0.000 description 2
- QEQROBXJKMVNGZ-UHFFFAOYSA-N 6-chloro-9-(1,3-dioxan-4-ylmethyl)purin-2-amine Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1CC1CCOCO1 QEQROBXJKMVNGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-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 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
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- 208000000903 Herpes simplex encephalitis Diseases 0.000 description 2
- 206010019973 Herpes virus infection Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 2
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 206010067152 Oral herpes Diseases 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- HQOJMTATBXYHNR-UHFFFAOYSA-M thallium(I) acetate Chemical compound [Tl+].CC([O-])=O HQOJMTATBXYHNR-UHFFFAOYSA-M 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8009040 | 1980-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO822712L true NO822712L (no) | 1982-08-09 |
Family
ID=20342543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822712A NO822712L (no) | 1980-12-22 | 1982-08-09 | Nye derivater av guanin. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4495190A (de) |
| EP (1) | EP0055239B1 (de) |
| JP (1) | JPS57501963A (de) |
| AT (1) | ATE20748T1 (de) |
| AU (1) | AU542373B2 (de) |
| CA (1) | CA1172633A (de) |
| DE (1) | DE3174948D1 (de) |
| DK (1) | DK148279C (de) |
| FI (1) | FI68054C (de) |
| GR (1) | GR76971B (de) |
| IL (1) | IL64501A (de) |
| NO (1) | NO822712L (de) |
| NZ (1) | NZ199334A (de) |
| RO (1) | RO85288B (de) |
| SU (2) | SU1272991A3 (de) |
| WO (1) | WO1982002202A1 (de) |
| ZA (1) | ZA818781B (de) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8203856D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine ii |
| SE8203855D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine i |
| US5047533A (en) * | 1983-05-24 | 1991-09-10 | Sri International | Acyclic purine phosphonate nucleotide analogs |
| HUT36464A (en) * | 1983-05-24 | 1985-09-30 | Newport Pharmaceuticals | Process for producing erythro-4-amino-3-/2-hydroxy-3-alkyl/-imidazol-5-carboxamide |
| GB8320308D0 (en) * | 1983-07-28 | 1983-09-01 | Wellcome Found | Antiviral combinations |
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| DE3485225D1 (de) * | 1983-08-18 | 1991-12-05 | Beecham Group Plc | Antivirale guanin-derivate. |
| IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| US4579849A (en) * | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| US4801710A (en) * | 1984-10-26 | 1989-01-31 | Merck & Co., Inc. | Regioselective synthesis of 9-substituted purine acyclonucleoside derivatives |
| YU45690B (sh) * | 1984-12-22 | 1992-07-20 | Krka Tovarna Zdraviln.Sol.O. | Postopek za pripravo 9-(2-hidroksietoksimetil)-gvanina |
| EP0193454A1 (de) * | 1985-02-25 | 1986-09-03 | Merck & Co. Inc. | 8-Substituierte-9-Hydroxyalkyl- und -Hydroxyalkoxymethylguanine und sie enthaltende pharmazeutische Zusammensetzungen |
| EP0219838A3 (de) * | 1985-10-22 | 1988-04-06 | Takeda Chemical Industries, Ltd. | Carbocyclische Purin-Nukleoside, ihre Herstellung und Verwendung |
| US5578468A (en) * | 1987-08-10 | 1996-11-26 | Duke University | Site-specific RNA cleavage |
| US5443964A (en) * | 1987-08-10 | 1995-08-22 | Duke University | Poxvirus insertion/expression vector |
| US4935427A (en) * | 1987-12-31 | 1990-06-19 | The United States Of America As Represented By The Department Of Health And Human Services | Pyrimidine and purine 1,2-butadiene-4-ols as anti-retroviral agents |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| US5352669A (en) * | 1990-03-13 | 1994-10-04 | The Of The United States Of America As Represented By The Department Of Health And Human Services | O6 -benzylated guanine, guanosine and 2'-deoxyguanosine compounds possessing O6 -alkylguanine-DNA alkyltransferase depleting activity |
| US5091432A (en) * | 1990-03-28 | 1992-02-25 | Glasky Alvin J | 9-substituted hypoxanthine bi-functional compounds and their neuroimmunological methods of use |
| SK280313B6 (sk) * | 1990-04-24 | 1999-11-08 | �Stav Organick� Chemie A Biochemie Av �R | N-(3-fluór-2-fosfonylmetoxypropyl)deriváty purínov |
| US5368853A (en) * | 1990-05-11 | 1994-11-29 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Leukoregulin anti-viral therapy |
| JP2939646B2 (ja) * | 1990-07-17 | 1999-08-25 | チッソ株式会社 | ４―置換―２―ヒドロキシブタン酸エステルおよび製造法 |
| US5874578A (en) * | 1992-07-13 | 1999-02-23 | Bristol-Myers Squibb | Process for preparing guanine-containing antiviral agents and purinyl salts useful in such process |
| US5525606A (en) | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| US6359114B1 (en) | 1995-06-07 | 2002-03-19 | Aphton Corp. | System for method for the modification and purification of proteins |
| US6060458A (en) * | 1998-02-13 | 2000-05-09 | The United States Of America As Represented By The Department Of Health And Human Services | Oligodeoxyribonucleotides comprising O6 -benzylguanine and their use |
| EP1440072A4 (de) * | 2001-10-30 | 2005-02-02 | Conforma Therapeutic Corp | Purinanaloga mit hsp90-inhibierender wirkung |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| US7129244B2 (en) * | 2003-09-18 | 2006-10-31 | Conforma Therapeutics Corporation | Triazolopyrimidines and related analogs as HSP90-inhibitors |
| CA2602257A1 (en) * | 2005-03-30 | 2006-10-05 | Conforma Therapeutics Corporation | Alkynyl pyrrolopyrimidines and related analogs as hsp90-inhibitors |
| AU2006259431B2 (en) * | 2005-06-14 | 2011-09-29 | Brigham Young University | Methods for selective N-9 glycosylation of purines |
| US20070105874A1 (en) * | 2005-09-23 | 2007-05-10 | Conforma Therapeutics Corporation | Anti-Tumor Methods Using Multi Drug Resistance Independent Synthetic HSP90 Inhibitors |
| CN108912055B (zh) * | 2018-08-20 | 2020-06-30 | 河南师范大学 | 一种合成抗病毒药物西多福韦中间体和布昔洛韦中间体的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL34188A (en) * | 1969-04-09 | 1972-12-29 | Seiyaku T Co | 4-(9-adenyl)-2,3-dihydroxy butyric acid and the preparation thereof |
| US3836656A (en) * | 1972-02-07 | 1974-09-17 | Sandoz Ag | Substituted purines as hypolipidemics |
| US4199574A (en) * | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| CS199093B1 (en) * | 1977-10-20 | 1980-07-31 | Antonin Holy | Antiviral agent |
| US4230708A (en) * | 1977-10-20 | 1980-10-28 | Stichting Rega V.Z.W. | Therapeutic application of (S) -or (RS)-9-(2, 3-dihydroxypropyl) adenine for use as antiviral agents |
| US4221910A (en) * | 1978-09-15 | 1980-09-09 | Newport Pharmaceuticals International, Inc. | 9-(Hydroxy alkyl)purines |
| US4423050A (en) * | 1981-05-21 | 1983-12-27 | Syntex (U.S.A.) Inc. | 9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent |
| US4451478A (en) * | 1982-03-12 | 1984-05-29 | Newport Pharmaceuticals International, Inc. | Imidazole compounds |
-
1981
- 1981-12-10 IL IL64501A patent/IL64501A/xx unknown
- 1981-12-18 ZA ZA818781A patent/ZA818781B/xx unknown
- 1981-12-21 NZ NZ199334A patent/NZ199334A/xx unknown
- 1981-12-21 AU AU78721/81A patent/AU542373B2/en not_active Ceased
- 1981-12-21 CA CA000392782A patent/CA1172633A/en not_active Expired
- 1981-12-21 GR GR66864A patent/GR76971B/el unknown
- 1981-12-22 DE DE8181850250T patent/DE3174948D1/de not_active Expired
- 1981-12-22 AT AT81850250T patent/ATE20748T1/de not_active IP Right Cessation
- 1981-12-22 EP EP81850250A patent/EP0055239B1/de not_active Expired
- 1981-12-22 WO PCT/SE1981/000389 patent/WO1982002202A1/en active IP Right Grant
- 1981-12-22 JP JP57500239A patent/JPS57501963A/ja active Pending
-
1982
- 1982-08-09 NO NO822712A patent/NO822712L/no unknown
- 1982-08-18 DK DK369982A patent/DK148279C/da not_active IP Right Cessation
- 1982-08-19 FI FI822891A patent/FI68054C/fi not_active IP Right Cessation
- 1982-08-20 SU SU823480213A patent/SU1272991A3/ru active
- 1982-08-21 RO RO108498A patent/RO85288B/ro unknown
- 1982-10-25 US US06/436,522 patent/US4495190A/en not_active Expired - Fee Related
-
1983
- 1983-10-31 SU SU833657074A patent/SU1272992A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0055239A1 (de) | 1982-06-30 |
| IL64501A (en) | 1985-07-31 |
| SU1272992A3 (ru) | 1986-11-23 |
| RO85288A (ro) | 1984-11-25 |
| NZ199334A (en) | 1985-09-13 |
| CA1172633A (en) | 1984-08-14 |
| US4495190A (en) | 1985-01-22 |
| AU542373B2 (en) | 1985-02-21 |
| DK148279B (da) | 1985-05-28 |
| WO1982002202A1 (en) | 1982-07-08 |
| SU1272991A3 (ru) | 1986-11-23 |
| GR76971B (de) | 1984-09-04 |
| FI68054C (fi) | 1985-07-10 |
| DK369982A (da) | 1982-08-18 |
| FI822891L (fi) | 1982-08-19 |
| FI822891A0 (fi) | 1982-08-19 |
| JPS57501963A (de) | 1982-11-04 |
| AU7872181A (en) | 1982-07-01 |
| DK148279C (da) | 1986-02-17 |
| FI68054B (fi) | 1985-03-29 |
| ATE20748T1 (de) | 1986-08-15 |
| DE3174948D1 (en) | 1986-08-21 |
| ZA818781B (en) | 1982-11-24 |
| IL64501A0 (en) | 1982-03-31 |
| EP0055239B1 (de) | 1986-07-16 |
| RO85288B (ro) | 1984-11-30 |
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