DD255351A5 - Verfahren zur herstellung von carbocyclischen purinnucleosiden - Google Patents

Verfahren zur herstellung von carbocyclischen purinnucleosiden Download PDF

Info

Publication number: DD255351A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; formula; hydroxyl group; preparation; acid
Prior art date: 1986-03-06

Application number

DD87300535A

Other languages

German (de)

English (en)

Inventor

Yoshio Taniyama

Takumi Hamana

Ryuji Marumoto

Naoki Yamamoto

Original Assignee

Takeda Chemical Industries Ltd,Jp

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.)

1986-03-06

Filing date

1987-03-06

Publication date

1988-03-30

1987-03-06 Application filed by Takeda Chemical Industries Ltd,Jp filed Critical Takeda Chemical Industries Ltd,Jp

1988-03-30 Publication of DD255351A5 publication Critical patent/DD255351A5/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 18
239000002777 nucleoside Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 68
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 5
-1 hypoxanthine-9-yl Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 12
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 8
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 claims description 6
UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
238000006722 reduction reaction Methods 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
UXRSUBXVCCYDKK-UHFFFAOYSA-N 1-(7h-purin-2-yl)ethanone Chemical compound CC(=O)C1=NC=C2NC=NC2=N1 UXRSUBXVCCYDKK-UHFFFAOYSA-N 0.000 claims 1
PMPFSQREEWMOPZ-RQJHMYQMSA-N 2-amino-9-[(1s,3r)-3-(hydroxymethyl)cyclopentyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1CC[C@@H](CO)C1 PMPFSQREEWMOPZ-RQJHMYQMSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
229910000083 tin tetrahydride Inorganic materials 0.000 claims 1
SKLQBHROODDCHR-UHFFFAOYSA-N trityltin Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([Sn])C1=CC=CC=C1 SKLQBHROODDCHR-UHFFFAOYSA-N 0.000 claims 1
239000003443 antiviral agent Substances 0.000 abstract description 4
238000004519 manufacturing process Methods 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 29
239000000203 mixture Substances 0.000 description 27
239000002904 solvent Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
210000004027 cell Anatomy 0.000 description 15
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 13
239000000843 powder Substances 0.000 description 13
239000000047 product Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 9
239000002253 acid Substances 0.000 description 8
241000700605 Viruses Species 0.000 description 7
239000000872 buffer Substances 0.000 description 7
AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 7
239000006188 syrup Substances 0.000 description 7
235000020357 syrup Nutrition 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
241000725303 Human immunodeficiency virus Species 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
125000002103 4,4'-dimethoxytriphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)(C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000013078 crystal Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000003826 tablet Substances 0.000 description 5
230000009385 viral infection Effects 0.000 description 5
208000009889 Herpes Simplex Diseases 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
230000000840 anti-viral effect Effects 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
241001493065 dsRNA viruses Species 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000002212 purine nucleoside Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VWCUMTCXBIRRSG-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-methoxybenzene Chemical compound COC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 VWCUMTCXBIRRSG-UHFFFAOYSA-N 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 3
229930024421 Adenine Natural products 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000598436 Human T-cell lymphotropic virus Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 description 3
229960000643 adenine Drugs 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 3
239000008187 granular material Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
108020004707 nucleic acids Proteins 0.000 description 3
150000007523 nucleic acids Chemical class 0.000 description 3
102000039446 nucleic acids Human genes 0.000 description 3
150000003833 nucleoside derivatives Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 3
PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 description 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
108020004414 DNA Proteins 0.000 description 2
241000450599 DNA viruses Species 0.000 description 2
241000283086 Equidae Species 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229930010555 Inosine Natural products 0.000 description 2
UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 description 2
102100034343 Integrase Human genes 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
108010092799 RNA-directed DNA polymerase Proteins 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000000427 antigen Substances 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000000120 cytopathologic effect Effects 0.000 description 2
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000003147 glycosyl group Chemical group 0.000 description 2
125000003738 guanin-9-yl group Chemical group O=C1N([H])C(N([H])[H])=NC2=C1N=C([H])N2[*] 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229960003786 inosine Drugs 0.000 description 2
DRAVOWXCEBXPTN-UHFFFAOYSA-N isoguanine Chemical compound NC1=NC(=O)NC2=C1NC=N2 DRAVOWXCEBXPTN-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000002953 phosphate buffered saline Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
238000005936 thiocarbonylation reaction Methods 0.000 description 2
UGRNVLGKAGREKS-GCXDCGAKSA-N (1r,2s,3r,5r)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1C[C@H](CO)[C@@H](O)[C@H]1O UGRNVLGKAGREKS-GCXDCGAKSA-N 0.000 description 1
UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical compound NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
DVNYTAVYBRSTGK-UHFFFAOYSA-N 5-aminoimidazole-4-carboxamide Chemical compound NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 description 1
HRYKDUPGBWLLHO-UHFFFAOYSA-N 8-azaadenine Chemical compound NC1=NC=NC2=NNN=C12 HRYKDUPGBWLLHO-UHFFFAOYSA-N 0.000 description 1
DKGIDXRLFYRRKD-UHFFFAOYSA-N 9-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-3h-purin-6-one Chemical compound C1=NC(C(N=CN2)=O)=C2N1CC1(C)CC(=C)C(=O)O1 DKGIDXRLFYRRKD-UHFFFAOYSA-N 0.000 description 1
MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
229930186232 Aristeromycin Natural products 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
241000701022 Cytomegalovirus Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000714165 Feline leukemia virus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000700721 Hepatitis B virus Species 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
208000029462 Immunodeficiency disease Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
108091028043 Nucleic acid sequence Proteins 0.000 description 1
208000001388 Opportunistic Infections Diseases 0.000 description 1
241001494479 Pecora 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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241000282887 Suidae Species 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
241000700647 Variola virus Species 0.000 description 1
241000711975 Vesicular stomatitis virus Species 0.000 description 1
VELDDJHOYPMZNR-UHFFFAOYSA-J [C+4].[O-]S(=O)OS([O-])=O.[O-]S(=O)OS([O-])=O Chemical compound [C+4].[O-]S(=O)OS([O-])=O.[O-]S(=O)OS([O-])=O VELDDJHOYPMZNR-UHFFFAOYSA-J 0.000 description 1
RBHODKISOUZAKB-UHFFFAOYSA-N [methylperoxy(diphenyl)methyl]benzene Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)(OOC)C1=CC=CC=C1 RBHODKISOUZAKB-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
231100000354 acute hepatitis Toxicity 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical group 0.000 description 1
125000001931 aliphatic group Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000036436 anti-hiv Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
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 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010367 cloning Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012228 culture supernatant Substances 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000000280 densification Methods 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
239000005546 dideoxynucleotide Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
229940098197 human immunoglobulin g Drugs 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
238000010166 immunofluorescence Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
XUGWUUDOWNZAGW-UHFFFAOYSA-N neplanocin A Natural products C1=NC=2C(N)=NC=NC=2N1C1C=C(CO)C(O)C1O XUGWUUDOWNZAGW-UHFFFAOYSA-N 0.000 description 1
208000020470 nervous system symptom Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
150000003834 purine nucleoside derivatives Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000527 sonication Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical class [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
241000701161 unidentified adenovirus Species 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
229940075420 xanthine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD87300535A 1986-03-06 1987-03-06 Verfahren zur herstellung von carbocyclischen purinnucleosiden DD255351A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4939586		1986-03-06

Publications (1)

Publication Number	Publication Date
DD255351A5 true DD255351A5 (de)	1988-03-30

Family

ID=12829840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87300535A DD255351A5 (de)	1986-03-06	1987-03-06	Verfahren zur herstellung von carbocyclischen purinnucleosiden

Country Status (5)

Country	Link
JP (1)	JPS6310787A (cs)
KR (1)	KR870008911A (cs)
CS (1)	CS264290B2 (cs)
DD (1)	DD255351A5 (cs)
SU (1)	SU1561826A3 (cs)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2007504269A (ja)	2003-09-05	2007-03-01	スリーエムイノベイティブプロパティズカンパニー	Ｃｄ５＋ｂ細胞リンパ腫の治療方法
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
EP1673087B1 (en)	2003-10-03	2015-05-13	3M Innovative Properties Company	Alkoxy substituted imidazoquinolines
AU2004293078B2 (en)	2003-11-25	2012-01-19	3M Innovative Properties Company	Substituted imidazo ring systems and methods
US8017779B2 (en)	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
US7915281B2 (en)	2004-06-18	2011-03-29	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
WO2006009826A1 (en)	2004-06-18	2006-01-26	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
WO2006038923A2 (en)	2004-06-18	2006-04-13	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
JP5313502B2 (ja)	2004-12-30	2013-10-09	スリーエムイノベイティブプロパティズカンパニー	置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
CA2592904C (en)	2004-12-30	2015-04-07	3M Innovative Properties Company	Chiral fused [1,2]imidazo[4,5-c] ring compounds
JP2008530022A (ja)	2005-02-04	2008-08-07	コーリーファーマシューティカルグループ，インコーポレイテッド	免疫反応調節物質を含む水性ゲル処方物
EP1846405A2 (en)	2005-02-11	2007-10-24	3M Innovative Properties Company	Oxime and hydroxylamine substituted imidazo 4,5-c ring compounds and methods
CA2602683A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	Pyrazolopyridine-1,4-diamines and analogs thereof
CA2602590A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
WO2008008432A2 (en)	2006-07-12	2008-01-17	Coley Pharmaceutical Group, Inc.	Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods

1987
- 1987-02-05 JP JP62025074A patent/JPS6310787A/ja active Pending
- 1987-03-05 SU SU874202204A patent/SU1561826A3/ru active
- 1987-03-06 KR KR870002029A patent/KR870008911A/ko not_active Withdrawn
- 1987-03-06 CS CS871517A patent/CS264290B2/cs unknown
- 1987-03-06 DD DD87300535A patent/DD255351A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU1561826A3 (ru)	1990-04-30
CS264290B2 (en)	1989-06-13
KR870008911A (ko)	1987-10-22
JPS6310787A (ja)	1988-01-18
CS151787A2 (en)	1988-09-16

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
AU596400B2 (en)	1990-05-03	Carbocyclic purine nucleosides, their production and use
DE69330274T2 (de)	2001-11-15	Enantiomerisch reine beta-d-dioxolan-nukleoside
DE69034119T2 (de)	2004-08-26	Substituierte-1,3-Oxathiolane mit antiviraler Wirkung
DE69116750T2 (de)	1996-11-14	9-Purinyl-Phosphonsäurederivate
DE3850645T2 (de)	1994-10-27	Puringruppen enthaltende Cyclobutane.
DE68920413T2 (de)	1995-05-11	Carbocyclische Nukleoside und Nukleotide.
DE69425574T2 (de)	2001-01-04	L-2',3'-dideoxy-nukleosidanaloga als anti-hepatitis b-(hbv) und anti-hiv-wirkstoffe
DE69806919T2 (de)	2003-02-27	Antivirale pyrimidin-nukleosid-analogen
AT390000B (de)	1990-02-26	Verwendung von 3'-azido-3'-desoxythymidin oder eines pharmazeutisch annehmbaren derivats hievon zur herstellung von medikamenten
DE69122264T2 (de)	1997-02-06	Substituierte 1,3-oxathiolane mit antiviralen eigenschaften
DE69109482T2 (de)	1996-02-15	Pyrimidinnucleosidderivat.
EP0626387A1 (de)	1994-11-30	Nukleoside und Oligonukleotide mit 2'-Ethergruppen
WO1993016091A1 (de)	1993-08-19	Neue liponucleotide, deren herstellung sowie deren verwendung als antivirale arzneimittel
DE3739366A1 (de)	1988-10-27	Desaza-purin-nucleosid-derivate, verfahren zu deren herstellung sowie deren verwendung bei der nucleinsaeure-sequenzierung sowie als antivirale mittel
EP0545966A1 (de)	1993-06-16	Neue phospholipid-derivate von nucleosiden, deren herstellung sowie deren verwendung als antivirale arzneimittel.
EP0679657A2 (de)	1995-11-02	Nukleoside und Oligonukleotide mit 2'-Ethergruppen
CH626363A5 (cs)	1981-11-13
DD297650A5 (de)	1992-01-16	Verfahren zur herstellung von fluor-substituierten purin-nucleosiden und sie enthaltender pharmazeutischer zubereitungen
DE2915254A1 (de)	1979-11-15	Neue chemische verbindungen, verfahren zu deren herstellung und deren verwendung als arzneimittel mit antiviraler wirkung
DE3887014T2 (de)	1994-05-19	Nukleoside, ihre Herstellung und pharmazeutische Zusammenstellungen.
DE69430587T2 (de)	2003-01-09	Pyrimidin-acyclonukleosid-derivate
DE68918804T2 (de)	1995-02-23	Acyclische 6-substituierte pyrimidin nukleosid-abkömmlinge und antivirale mittel, die dieselben als aktive mittel enthalten.
JPS6310787A (ja)	1988-01-18	ヌクレオシド類縁体、その製造法および抗ウイルス剤
DE3390162T1 (de)	1985-02-21	Desoxyuridinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika
EP0219838A2 (en)	1987-04-29	Carbocyclic purine nucleosides, their production and use