NO822712L - Nye derivater av guanin. - Google Patents

Nye derivater av guanin.

Info

Publication number: NO822712L
Authority: NO; Norway
Prior art keywords: compound; formula; hydroxy; groups; hydrogen
Prior art date: 1980-12-22

Application number

NO822712A

Other languages

English (en)

Norwegian (no)

Inventor

Curt-Erik Hagberg

Zsuzsanna Maria Ilona Kovacs

Goeran Bertil Stening

Karl Nils-Gunnar Johansson

Original Assignee

Astra Laekemedel Ab

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.)

1980-12-22

Filing date

1982-08-09

Publication date

1982-08-09

1982-08-09 Application filed by Astra Laekemedel Ab filed Critical Astra Laekemedel Ab

1982-08-09 Publication of NO822712L publication Critical patent/NO822712L/no

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
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208000000903 Herpes simplex encephalitis Diseases 0.000 description 2
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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
229940124532 absorption promoter Drugs 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
201000008275 breast carcinoma Diseases 0.000 description 2
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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)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (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)
Detection And Prevention Of Errors In Transmission (AREA)
Saccharide Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO822712A 1980-12-22 1982-08-09 Nye derivater av guanin. NO822712L (no)

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 (da)
EP (1)	EP0055239B1 (da)
JP (1)	JPS57501963A (da)
AT (1)	ATE20748T1 (da)
AU (1)	AU542373B2 (da)
CA (1)	CA1172633A (da)
DE (1)	DE3174948D1 (da)
DK (1)	DK148279C (da)
FI (1)	FI68054C (da)
GR (1)	GR76971B (da)
IL (1)	IL64501A (da)
NO (1)	NO822712L (da)
NZ (1)	NZ199334A (da)
RO (1)	RO85288B (da)
SU (2)	SU1272991A3 (da)
WO (1)	WO1982002202A1 (da)
ZA (1)	ZA818781B (da)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE8203855D0 (sv) *	1982-06-21	1982-06-21	Astra Laekemedel Ab	Novel derivatives of guanine i
SE8203856D0 (sv) *	1982-06-21	1982-06-21	Astra Laekemedel Ab	Novel derivatives of guanine ii
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
EP0141927B1 (en) *	1983-08-18	1991-10-30	Beecham Group Plc	Antiviral guanine derivatives
US5684153A (en)	1984-08-16	1997-11-04	Beecham Group Plc	Process for the preparation of purine derivatives
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 (en) *	1985-02-25	1986-09-03	Merck & Co. Inc.	8-Substituted-9-hydroxyalkyl and hydroxyalkoxymethyl-guanines and pharmaceutical compositions containing them
EP0219838A3 (en) *	1985-10-22	1988-04-06	Takeda Chemical Industries, Ltd.	Carbocyclic purine nucleosides, their production and use
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 (en)	2001-10-30	2005-02-02	Conforma Therapeutic Corp	PURINE ANALOGS HAVING HSP90 INHIBITORY ACTIVITY
US20070129334A1 (en) *	2001-10-30	2007-06-07	Conforma Therapeutics Corporation	Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
NZ546611A (en)	2003-09-18	2010-02-26	Conforma Therapeutics Corp	Novel heterocyclic compounds as HSP90-inhibitors
BRPI0609509A2 (pt)	2005-03-30	2010-04-13	Conforma Therapeutics Corp	composto ou um polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso do composto, polimorfo, solvato, tautÈmero, enanciÈmero, pró-droga ou sal farmaceuticamente aceitável
CA2653247C (en) *	2005-06-14	2012-12-18	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

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* Cited by examiner, † Cited by third party
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 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
- 1981-12-21 NZ NZ199334A patent/NZ199334A/xx unknown
- 1981-12-22 WO PCT/SE1981/000389 patent/WO1982002202A1/en not_active Ceased
- 1981-12-22 JP JP57500239A patent/JPS57501963A/ja active Pending
- 1981-12-22 AT AT81850250T patent/ATE20748T1/de not_active IP Right Cessation
- 1981-12-22 DE DE8181850250T patent/DE3174948D1/de not_active Expired
- 1981-12-22 EP EP81850250A patent/EP0055239B1/en not_active Expired
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
ZA818781B (en)	1982-11-24
RO85288A (ro)	1984-11-25
IL64501A0 (en)	1982-03-31
DK148279C (da)	1986-02-17
DE3174948D1 (en)	1986-08-21
GR76971B (da)	1984-09-04
US4495190A (en)	1985-01-22
AU7872181A (en)	1982-07-01
ATE20748T1 (de)	1986-08-15
CA1172633A (en)	1984-08-14
WO1982002202A1 (en)	1982-07-08
DK369982A (da)	1982-08-18
AU542373B2 (en)	1985-02-21
EP0055239A1 (en)	1982-06-30
FI68054B (fi)	1985-03-29
SU1272992A3 (ru)	1986-11-23
FI822891L (fi)	1982-08-19
EP0055239B1 (en)	1986-07-16
DK148279B (da)	1985-05-28
FI68054C (fi)	1985-07-10
FI822891A0 (fi)	1982-08-19
RO85288B (ro)	1984-11-30
NZ199334A (en)	1985-09-13
JPS57501963A (da)	1982-11-04
SU1272991A3 (ru)	1986-11-23
IL64501A (en)	1985-07-31

Publication	Publication Date	Title
US4495190A (en)	1985-01-22	Derivatives of guanine for combating herpes virus infections
US4798833A (en)	1989-01-17	Guanine derivative
US5036071A (en)	1991-07-30	Derivatives of purine
US4287188A (en)	1981-09-01	Purine derivatives
WO1999035147A1 (en)	1999-07-15	Purine derivatives and adenosine a2 receptor antagonists serving as preventives/remedies for diabetes
DK146595B (da)	1983-11-14	Analogifremgangsmaade til fremstilling af substituerede 9-alkoxymethyl- eller -alkylthiomethylpuriner eller salte heraf
EP0291229B1 (en)	1994-04-13	9(2-(hydroxymethyl) cycloalkylmethyl)guanines
EP0182024A2 (en)	1986-05-28	Purine derivatives and their pharmaceutical use
HU208825B (en)	1994-01-28	Process for producing new xantine derivatives and pharmaceutical preparatives containing said compounds
CA2257807C (en)	2002-09-24	Improved methods for the synthesis of chemical compounds having pde-iv inhibitory activity
Larsson et al.	1983	9-(3, 4-Dihydroxybutyl) guanine, a new inhibitor of herpesvirus multiplication
GB2122198A (en)	1984-01-11	Antiviral guanine derivatives
HU200461B (en)	1990-06-28	Process for producing new 9-(n-hyudroxyalkoxy)-purine derivatives and pharmaceutical compositions comprising such compounds
EP0103552A2 (en)	1984-03-21	Novel derivatives of guanine
US5250688A (en)	1993-10-05	Purine derivatives
US7045525B1 (en)	2006-05-16	Use of (R)-peniciclovir triphosphate for the manufacture of a medicament for the treatment of viral diseases
STENING	1983	9-(3, 4-Dihydroxybutyl) guanine, Inhibitor of Herpesvirus Multiplication
NO145404B (no)	1981-12-07	Analogifremgangsmaate til fremstilling av terapeutisk virksomme purinforbindelser og salter derav
NO874782L (no)	1983-08-02	Guaninderivater.