CS203093B2 - Method of preparing substituted purines - Google Patents
Method of preparing substituted purines Download PDFInfo
- Publication number
- CS203093B2 CS203093B2 CS773087A CS308777A CS203093B2 CS 203093 B2 CS203093 B2 CS 203093B2 CS 773087 A CS773087 A CS 773087A CS 308777 A CS308777 A CS 308777A CS 203093 B2 CS203093 B2 CS 203093B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- amino
- formula
- carbon atoms
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 150000003212 purines Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- -1 C 1 -C 4 alkoxy Chemical class 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 150000003839 salts Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 239000007795 chemical reaction product Substances 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
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical class N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000840 anti-viral effect Effects 0.000 abstract description 7
- 241000124008 Mammalia Species 0.000 abstract description 5
- CSMCRCLIPQDIKB-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethanol Chemical compound NC1=NC(N)=C2N=CN(COCCO)C2=N1 CSMCRCLIPQDIKB-UHFFFAOYSA-N 0.000 abstract description 4
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 abstract description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000002431 hydrogen Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 10
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229930024421 Adenine Natural products 0.000 description 7
- 229960000643 adenine Drugs 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- YDLAHBBJAGGIJZ-UHFFFAOYSA-N 2-sulfanylethyl acetate Chemical compound CC(=O)OCCS YDLAHBBJAGGIJZ-UHFFFAOYSA-N 0.000 description 3
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 3
- LEYMKLZVUYUKSH-UHFFFAOYSA-N 6-chloro-9-(ethylsulfanylmethyl)purine Chemical compound N1=CN=C2N(CSCC)C=NC2=C1Cl LEYMKLZVUYUKSH-UHFFFAOYSA-N 0.000 description 3
- NGDBUGSDGNWXQR-UHFFFAOYSA-N 9-(ethylsulfanylmethyl)purin-6-amine Chemical compound N1=CN=C2N(CSCC)C=NC2=C1N NGDBUGSDGNWXQR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000055025 Adenosine deaminases Human genes 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 3
- 241001529453 unidentified herpesvirus Species 0.000 description 3
- ZZQWOHMPHXYXCX-UHFFFAOYSA-N 1-(6-amino-2-methylpurin-9-yl)oxypropan-2-ol Chemical compound OC(CON1C2=NC(=NC(=C2N=C1)N)C)C ZZQWOHMPHXYXCX-UHFFFAOYSA-N 0.000 description 2
- KFGDVSVZKZPADB-UHFFFAOYSA-N 2-[(6-amino-2-chloropurin-9-yl)methoxy]ethanol Chemical compound NC1=NC(Cl)=NC2=C1N=CN2COCCO KFGDVSVZKZPADB-UHFFFAOYSA-N 0.000 description 2
- PEIRNIBZTBBIHT-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methoxy]ethanol Chemical compound NC1=NC=NC2=C1N=CN2COCCO PEIRNIBZTBBIHT-UHFFFAOYSA-N 0.000 description 2
- IFCSUTHKDBXWGF-UHFFFAOYSA-N 2-[(6-chloropurin-9-yl)methylsulfanyl]ethyl acetate Chemical compound N1=CN=C2N(CSCCOC(=O)C)C=NC2=C1Cl IFCSUTHKDBXWGF-UHFFFAOYSA-N 0.000 description 2
- KRSXHHCWFICKCO-UHFFFAOYSA-N 2-[1-(6-aminopurin-9-yl)octoxy]ethanol Chemical compound N1=CN=C2N(C(OCCO)CCCCCCC)C=NC2=C1N KRSXHHCWFICKCO-UHFFFAOYSA-N 0.000 description 2
- RWCYGLJSLQIGDH-UHFFFAOYSA-N 2-chloro-9-(2-hydroxyethoxymethyl)-3h-purin-6-one Chemical compound N1=C(Cl)NC(=O)C2=C1N(COCCO)C=N2 RWCYGLJSLQIGDH-UHFFFAOYSA-N 0.000 description 2
- RTKIXOQNORJYCY-UHFFFAOYSA-N 4-[2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethoxy]-4-oxobutanoic acid Chemical compound O=C1NC(N)=NC2=C1N=CN2COCCOC(=O)CCC(O)=O RTKIXOQNORJYCY-UHFFFAOYSA-N 0.000 description 2
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000700618 Vaccinia virus Species 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- XZCHJYXUPALGHH-UHFFFAOYSA-N chloromethylsulfanylethane Chemical compound CCSCCl XZCHJYXUPALGHH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 1
- HNQDBKBFYQVYLX-UHFFFAOYSA-N 2-(chloromethoxy)ethyl benzoate Chemical compound ClCOCCOC(=O)C1=CC=CC=C1 HNQDBKBFYQVYLX-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- CBGCJDKLQNGINO-UHFFFAOYSA-N 2-(chloromethylsulfanyl)ethyl acetate Chemical compound CC(=O)OCCSCCl CBGCJDKLQNGINO-UHFFFAOYSA-N 0.000 description 1
- MIQAYYADYWRRMJ-UHFFFAOYSA-N 2-(purin-9-ylmethoxy)ethanol Chemical class N1=CN=C2N(COCCO)C=NC2=C1 MIQAYYADYWRRMJ-UHFFFAOYSA-N 0.000 description 1
- RHMAZSNTRRZPMG-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethyl acetate Chemical compound N1=C(N)N=C2N(COCCOC(=O)C)C=NC2=C1N RHMAZSNTRRZPMG-UHFFFAOYSA-N 0.000 description 1
- VUJCFVXDTNKPKW-UHFFFAOYSA-N 2-[(2,6-dichloropurin-9-yl)methoxy]ethyl benzoate Chemical compound C12=NC(Cl)=NC(Cl)=C2N=CN1COCCOC(=O)C1=CC=CC=C1 VUJCFVXDTNKPKW-UHFFFAOYSA-N 0.000 description 1
- MKTTXCDPHPEDCL-UHFFFAOYSA-N 2-[(2-amino-6-chloropurin-9-yl)methoxy]ethyl benzoate Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1COCCOC(=O)C1=CC=CC=C1 MKTTXCDPHPEDCL-UHFFFAOYSA-N 0.000 description 1
- FZLBUUNVTLPQAK-UHFFFAOYSA-N 2-[(2-amino-6-methylsulfanylpurin-9-yl)methoxy]ethanol Chemical compound CSC1=NC(N)=NC2=C1N=CN2COCCO FZLBUUNVTLPQAK-UHFFFAOYSA-N 0.000 description 1
- XAZMDVUJLSYFIQ-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl benzoate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1COCCOC(=O)C1=CC=CC=C1 XAZMDVUJLSYFIQ-UHFFFAOYSA-N 0.000 description 1
- AQNIHRZKSKEVRM-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methylsulfanyl]ethanol Chemical compound NC1=NC=NC2=C1N=CN2CSCCO AQNIHRZKSKEVRM-UHFFFAOYSA-N 0.000 description 1
- DELWFOSIVCZBMF-UHFFFAOYSA-N 2-[(6-chloropurin-9-yl)methoxy]ethyl benzoate Chemical compound C1=NC=2C(Cl)=NC=NC=2N1COCCOC(=O)C1=CC=CC=C1 DELWFOSIVCZBMF-UHFFFAOYSA-N 0.000 description 1
- PNTVPZKGFNDNLI-UHFFFAOYSA-N 2-[1-[6-(dimethylamino)purin-9-yl]ethoxy]ethanol Chemical compound N1=CN=C2N(C(OCCO)C)C=NC2=C1N(C)C PNTVPZKGFNDNLI-UHFFFAOYSA-N 0.000 description 1
- YZPZJYIBJTVVKO-UHFFFAOYSA-N 2-amino-9-(3-hydroxypropoxymethyl)-3h-purin-6-one Chemical compound O=C1NC(N)=NC2=C1N=CN2COCCCO YZPZJYIBJTVVKO-UHFFFAOYSA-N 0.000 description 1
- PFSWUZHMRYIAAE-UHFFFAOYSA-N 2-amino-9-[2-(2-hydroxyethoxy)ethyl]-3h-purin-6-one Chemical compound O=C1NC(N)=NC2=C1N=CN2CCOCCO PFSWUZHMRYIAAE-UHFFFAOYSA-N 0.000 description 1
- AVQYIFWCVPLCHT-UHFFFAOYSA-N 4-[2-[(6-aminopurin-9-yl)methoxy]ethylcarbamoyl]benzenesulfonyl fluoride Chemical compound C1=NC=2C(N)=NC=NC=2N1COCCNC(=O)C1=CC=C(S(F)(=O)=O)C=C1 AVQYIFWCVPLCHT-UHFFFAOYSA-N 0.000 description 1
- ZBWLXZPWFUGKQP-UHFFFAOYSA-N 9-(1-aminopropan-2-yloxymethyl)-N,N-dimethylpurin-6-amine hydrochloride Chemical compound Cl.N1=CN=C2N(COC(CN)C)C=NC2=C1N(C)C ZBWLXZPWFUGKQP-UHFFFAOYSA-N 0.000 description 1
- TVVDJOHQDKVVHQ-UHFFFAOYSA-N 9-[(2-amino-1-cyclopentylethoxy)methyl]-N,N-dimethylpurin-6-amine dihydrochloride Chemical compound Cl.Cl.C1=NC=2C(N(C)C)=NC=NC=2N1COC(CN)C1CCCC1 TVVDJOHQDKVVHQ-UHFFFAOYSA-N 0.000 description 1
- YECXMYYFCZOAQQ-UHFFFAOYSA-N 9-[1,3-bis(phenylmethoxy)propan-2-yloxymethyl]purin-6-amine Chemical compound C1=NC=2C(N)=NC=NC=2N1COC(COCC=1C=CC=CC=1)COCC1=CC=CC=C1 YECXMYYFCZOAQQ-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
- UBRISLKLDNNLKP-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)OCC(COC(C1=CC=CC=C1)=O)OCN1C2=NC=NC(=C2N=C1)N Chemical compound C(C1=CC=CC=C1)(=O)OCC(COC(C1=CC=CC=C1)=O)OCN1C2=NC=NC(=C2N=C1)N UBRISLKLDNNLKP-UHFFFAOYSA-N 0.000 description 1
- LRMCSRVUZMPTGZ-UHFFFAOYSA-N CC=1C(=C(C(=O)O)C=CC1)O.C(C(C)O)O Chemical compound CC=1C(=C(C(=O)O)C=CC1)O.C(C(C)O)O LRMCSRVUZMPTGZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
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- 229940080428 lactose 200 mg Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical class [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
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- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB38278/74A GB1523865A (en) | 1974-09-02 | 1974-09-02 | Purine compunds and salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203093B2 true CS203093B2 (en) | 1981-02-27 |
Family
ID=10402412
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS773087A CS203093B2 (en) | 1974-09-02 | 1975-09-02 | Method of preparing substituted purines |
| CS755957A CS203092B2 (en) | 1974-09-02 | 1975-09-02 | Method of preparing substituted purines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS755957A CS203092B2 (en) | 1974-09-02 | 1975-09-02 | Method of preparing substituted purines |
Country Status (35)
| Country | Link |
|---|---|
| US (3) | US4323573A (en]) |
| JP (1) | JPS5154589A (en]) |
| AR (4) | AR220299A1 (en]) |
| AT (1) | AT354462B (en]) |
| AU (1) | AU503160B2 (en]) |
| BE (1) | BE833006A (en]) |
| BG (4) | BG26536A4 (en]) |
| CA (1) | CA1062257A (en]) |
| CH (7) | CH626363A5 (en]) |
| CS (2) | CS203093B2 (en]) |
| CY (1) | CY1033A (en]) |
| DD (1) | DD122092A5 (en]) |
| DE (1) | DE2539963C2 (en]) |
| DK (1) | DK146595C (en]) |
| ES (3) | ES440631A1 (en]) |
| FI (1) | FI60709C (en]) |
| FR (1) | FR2282892A1 (en]) |
| GB (1) | GB1523865A (en]) |
| HK (1) | HK84379A (en]) |
| HU (1) | HU176730B (en]) |
| IE (1) | IE42282B1 (en]) |
| IL (1) | IL48035A (en]) |
| KE (1) | KE3002A (en]) |
| LU (1) | LU73304A1 (en]) |
| MC (1) | MC1068A1 (en]) |
| MY (1) | MY8200191A (en]) |
| NL (1) | NL175061C (en]) |
| NO (1) | NO144216C (en]) |
| NZ (1) | NZ178556A (en]) |
| RO (4) | RO74275A (en]) |
| SE (1) | SE428562C (en]) |
| SU (7) | SU904523A3 (en]) |
| YU (4) | YU39947B (en]) |
| ZA (1) | ZA755574B (en]) |
| ZM (1) | ZM12875A1 (en]) |
Families Citing this family (120)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146715A (en) | 1975-08-27 | 1979-03-27 | Burroughs Wellcome Co. | 2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines |
| US4060616A (en) * | 1976-03-01 | 1977-11-29 | Burroughs Wellcome Co. | Purine derivatives with repeating unit |
| AU521577B2 (en) * | 1977-02-24 | 1982-04-22 | Wellcome Foundation Limited, The | 9-hydroxyethoxymethyl guanine phosphates |
| US4287188A (en) | 1977-02-24 | 1981-09-01 | Burroughs Wellcome Co. | Purine derivatives |
| KR830005852A (ko) * | 1980-07-18 | 1983-09-14 | 미첼 페터 잭슨 | 피부와 점막의 비루스 감염치료에 적합한 국소치료제의 제조방법 |
| US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
| US5157120A (en) * | 1980-09-16 | 1992-10-20 | Syntex (U.S.A.) Inc. | Guanine derivatives |
| JPS57102818A (en) * | 1980-10-15 | 1982-06-26 | Wellcome Found | Treatment for fish virus diseases |
| US4423050A (en) * | 1981-05-21 | 1983-12-27 | Syntex (U.S.A.) Inc. | 9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent |
| US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
| US4603219A (en) * | 1981-05-21 | 1986-07-29 | Syntex (U.S.A.) Inc. | 1,3-dibenzyloxy-2-acetoxymethoxypropane, intermediate for 9-(1,3-dihydroxy-2-propoxymethyl)guanine |
| CA1305138C (en) * | 1981-08-11 | 1992-07-14 | Howard J. Schaeffer | Antiviral acyclic nucleoside derivatives and their preparation |
| FI823195A7 (fi) * | 1981-09-16 | 1983-03-17 | Ens Bio Logicals Inc | Puriinijohdannaisten valmistusmenetelmä. |
| AU564576B2 (en) * | 1981-09-24 | 1987-08-20 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Purine derivatives |
| US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
| MC1585A1 (fr) * | 1982-02-12 | 1985-02-22 | Ens Bio Logicals Inc | Procede de fabrication de compositions antivirales |
| 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 |
| NL8202626A (nl) * | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| DE3376325D1 (en) * | 1982-10-14 | 1988-05-26 | Wellcome Found | Antiviral purine derivatives |
| US4745119A (en) * | 1982-10-14 | 1988-05-17 | Burroughs Wellcome Co. | Method for using purine derivatives |
| US5059604A (en) * | 1982-10-14 | 1991-10-22 | Burroughs Wellcome Co. | 2-amino purine derivatives |
| US4649140A (en) * | 1982-10-14 | 1987-03-10 | Burroughs Wellcome Co. | Purine derivatives |
| US4609662A (en) * | 1982-10-14 | 1986-09-02 | Burroughs Wellcome Co. | Method for using purine derivatives |
| US4612314A (en) * | 1982-12-22 | 1986-09-16 | Syntex (U.S.A.) Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
| US4461757A (en) * | 1983-02-23 | 1984-07-24 | Ens Bio Logicals Inc. | Dimethylaminomethylenated anti-herpes compounds |
| ES8403904A1 (es) * | 1983-02-25 | 1984-04-01 | Ind Farma Especial | Un procedimiento para la preparacion de acicloguanosina. |
| US5047533A (en) * | 1983-05-24 | 1991-09-10 | Sri International | Acyclic purine phosphonate nucleotide analogs |
| US4557934A (en) | 1983-06-21 | 1985-12-10 | The Procter & Gamble Company | Penetrating topical pharmaceutical compositions containing 1-dodecyl-azacycloheptan-2-one |
| ZA844744B (en) * | 1983-06-24 | 1986-02-26 | Merck & Co Inc | Antiviral agents |
| US4880820A (en) * | 1983-06-24 | 1989-11-14 | Merck & Co., Inc. | Guanine derivatives |
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| US4897479A (en) * | 1983-09-30 | 1990-01-30 | Merck & Co., Inc. | Arylsulfonyloxy purine intermediates |
| JPS6094992A (ja) * | 1983-10-28 | 1985-05-28 | Sankyo Co Ltd | グリゼオ−ル酸誘導体 |
| US4918219A (en) * | 1983-10-31 | 1990-04-17 | Warner-Lambert Company | Glycerine derivatives |
| ZA848080B (en) * | 1983-10-31 | 1985-06-26 | Warner Lambert Co | Purine derivatives |
| US4806642A (en) * | 1984-10-05 | 1989-02-21 | Warner-Lambert Company | Purine derivatives |
| IE842642L (en) * | 1983-10-31 | 1985-04-30 | Harvard College | Purine Derivatives |
| US4579849A (en) * | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| US4617304A (en) * | 1984-04-10 | 1986-10-14 | Merck & Co., Inc. | Purine derivatives |
| DK163985A (da) * | 1984-04-13 | 1985-10-14 | Wellcome Found | Antivirale purinderivater, fremgangsmaade til deres fremstilling og farmaceutiske kompositioner indeholdende forbindelserne |
| US4636507A (en) * | 1984-04-30 | 1987-01-13 | Hoechst-Roussel Pharmaceuticals Inc. | Host defense mechanism enhancement |
| DE3585643D1 (de) | 1984-07-03 | 1992-04-23 | Wellcome Found | Antiviren-verbindungen, behandlung und formulierungen. |
| WO1986000901A1 (en) * | 1984-07-20 | 1986-02-13 | Gauntt Charles O | Immunoregulatory and anti-viral compound |
| SE8406538D0 (sv) * | 1984-12-21 | 1984-12-21 | Astra Laekemedel Ab | Novel derivatives of purine |
| US5683990A (en) * | 1985-03-16 | 1997-11-04 | Glaxo Wellcome Inc. | Treatment of human viral infections |
| US4724232A (en) * | 1985-03-16 | 1988-02-09 | Burroughs Wellcome Co. | Treatment of human viral infections |
| CS263952B1 (en) * | 1985-04-25 | 1989-05-12 | Holy Antonin | Remedy with antiviral effect |
| CS263951B1 (en) * | 1985-04-25 | 1989-05-12 | Antonin Holy | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| DE3667058D1 (en) | 1985-05-02 | 1989-12-28 | Wellcome Found | Antiviral compounds |
| IL78643A0 (en) * | 1985-05-02 | 1986-08-31 | Wellcome Found | Purine derivatives,their preparation and pharmaceutical compositions containing them |
| DE3529497A1 (de) * | 1985-08-17 | 1987-02-26 | Boehringer Mannheim Gmbh | N(pfeil hoch)6(pfeil hoch)-disubstituierte purinderivate, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel |
| DE3627024A1 (de) * | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
| IT1207507B (it) * | 1985-10-21 | 1989-05-25 | Baldacci Lab Spa | Coniugato della 9-(2-idrossietossimetil)guanina con albumina umana lattosaminata, procedimento per la sua preparazione e composizioni farmaceutiche che la contengono. |
| AU618723B2 (en) * | 1986-10-06 | 1992-01-09 | University Of Virginia Alumni Patents Foundation, The | Use of an adenosine, hypoxanthine and ribose-containing solution for improved protection of the heart during surgery |
| US4916225A (en) * | 1986-11-25 | 1990-04-10 | Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr | 9-substituted guanines |
| US4978655A (en) * | 1986-12-17 | 1990-12-18 | Yale University | Use of 3'-deoxythymidin-2'-ene (3'deoxy-2',3'-didehydrothymidine) in treating patients infected with retroviruses |
| US4829055A (en) * | 1987-01-23 | 1989-05-09 | Naficy Sadeque S | Method of treatment for herpes infections of external tissues |
| US5565566A (en) * | 1987-04-24 | 1996-10-15 | Discovery Therapeutics, Inc. | N6 -substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US4835104A (en) * | 1987-06-16 | 1989-05-30 | Ajinomoto Co., Inc., Patent & Licensing Department | Process for producing and purifying 2',3'-dideoxynucleosides, and process for producing 2',3'-dideoxy-2',3'-didehydronucleosides |
| US6306647B1 (en) | 1987-06-16 | 2001-10-23 | Ajinomoto Co., Inc. | Process for producing and purifying 2′,3′-dideoxynucleosides, and process for producing 2′,3′-dideoxy-2′,3′-didehydronucleosides |
| GB8725939D0 (en) * | 1987-11-05 | 1987-12-09 | Wellcome Found | Therapeutic compounds |
| GB8719367D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Therapeutic compounds |
| CA1302887C (en) * | 1987-11-24 | 1992-06-09 | Yves Langelier | Combination of acyclovir or a derivative thereof and bacitracin |
| JPH01121424U (en]) * | 1988-02-10 | 1989-08-17 | ||
| GB8815241D0 (en) * | 1988-06-27 | 1988-08-03 | Wellcome Found | Antiviral combinations & compounds therefor |
| US5164395A (en) * | 1988-06-27 | 1992-11-17 | Burroughs Wellcome Co. | Antiviral acetyl pyridine derivative or said acetyl pyridine derivative in combination with acyclovir |
| GB8816760D0 (en) * | 1988-07-14 | 1988-08-17 | Wellcome Found | Therapeutic compounds |
| EP0366385B1 (en) * | 1988-10-24 | 1993-06-09 | The Wellcome Foundation Limited | Guanine derivatives having antiviral activity and their pharmaceutically acceptable salts |
| WO1990009178A1 (en) * | 1989-01-31 | 1990-08-23 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| GB8907173D0 (en) * | 1989-03-30 | 1989-05-10 | Beecham Group Plc | Novel compounds |
| GB8912043D0 (en) * | 1989-05-25 | 1989-07-12 | Beecham Group Plc | Novel compounds |
| GB9001886D0 (en) * | 1990-01-26 | 1990-03-28 | Beecham Group Plc | Pharmaceutical formulation |
| DE4008858A1 (de) * | 1990-03-20 | 1991-09-26 | Hoechst Ag | Substituierte purine, verfahren zu ihrer hertellung sowie ihre verwendung als antivirale mittel |
| CA2033447C (en) * | 1990-12-31 | 1999-08-31 | Robert Deziel | Synergistic combination for treating herpes infections |
| US5580571A (en) * | 1991-10-15 | 1996-12-03 | Hostetler; Karl Y. | Nucleoside analogues |
| US5879700A (en) * | 1991-10-15 | 1999-03-09 | Hostetler; Karl Y. | Nucleoside analogue phosphates for topical use |
| CA2091732C (en) * | 1992-07-08 | 1998-07-21 | Anica Markovac | A process for the preparation of 2-fluoro-9-(2,3,5-tri-o-benzyl-beta-d-arabinofuranosyl) adenine |
| DK169121B1 (da) | 1992-09-09 | 1994-08-22 | Gea Farmaceutisk Fabrik As | Antiviralt virksom farmaceutisk olie-i-vand-emulsion indeholdende 9-[(2-hydroxyethoxy)methyl]guanin (acyclovir) eller et salt eller en ester deraf |
| EP0589335B1 (de) * | 1992-09-24 | 2003-06-18 | Hoechst Aktiengesellschaft | N1-Substituierte 1H-1,2,3-Triazolo[4,5-d]pyrimidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als antivirale Mittel |
| US5654286A (en) * | 1993-05-12 | 1997-08-05 | Hostetler; Karl Y. | Nucleotides for topical treatment of psoriasis, and methods for using same |
| US6015573A (en) * | 1993-05-12 | 2000-01-18 | Hostetler; Karl Y. | Nucleoside phosphate therapy for viral infection |
| IT1264599B1 (it) * | 1993-06-14 | 1996-10-04 | Solar Chem Sa | Processo per la sintesi della 9-(2-idrossietossimetil)- guanina |
| US5567816A (en) * | 1994-07-26 | 1996-10-22 | Syntex (U.S.A.) Inc. | Preparation of acyclovir using 1,3 dioxolane |
| US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
| US6083953A (en) * | 1994-07-28 | 2000-07-04 | Syntex (U.S.A.) Inc. | 2- (2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3- propanediol derivative |
| US5565565A (en) | 1994-08-04 | 1996-10-15 | Syntex (U.S.A.) Inc. | Preparation of N-9 substituted guanine compounds |
| US5627185A (en) * | 1994-11-23 | 1997-05-06 | Gosselin; Gilles | Acyclovir derivatives as antiviral agents |
| US5756736A (en) * | 1996-01-26 | 1998-05-26 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
| US5840890A (en) * | 1996-01-26 | 1998-11-24 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
| US6040446A (en) * | 1996-01-26 | 2000-03-21 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol derivative |
| US5700936A (en) * | 1996-01-26 | 1997-12-23 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol valinate |
| IN179493B (en]) * | 1996-02-22 | 1997-10-11 | Lupin Laboraties Ltd | |
| US5789589A (en) * | 1996-04-22 | 1998-08-04 | Drug Innovation & Design, Inc. | Guanine analog phosphates |
| US6440980B1 (en) | 1996-09-17 | 2002-08-27 | Avanir Pharmaceuticals | Synergistic inhibition of viral replication by long-chain hydrocarbons and nucleoside analogs |
| RU2111967C1 (ru) * | 1996-09-26 | 1998-05-27 | Генкин Дмитрий Дмитриевич | Способ получения ацикловира |
| US6180790B1 (en) | 1997-05-15 | 2001-01-30 | Drug Innovation And Design, Inc. | Methods of preparing acyclovir prodrugs |
| AU731225C (en) * | 1997-05-15 | 2001-10-18 | Drug Innovation & Design, Inc. | Acyclovir diester derivatives |
| RU2160105C1 (ru) * | 2000-04-27 | 2000-12-10 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Противовирусное средство и способ его получения |
| RU2179851C1 (ru) * | 2000-12-21 | 2002-02-27 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Противовирусный фармацевтический состав |
| RU2175230C1 (ru) * | 2001-01-23 | 2001-10-27 | Открытое акционерное общество "Химико-фармацевтический комбинат "Акрихин" | Фармацевтическая композиция с противовирусной активностью и способ ее получения |
| JP2005519868A (ja) * | 2001-10-16 | 2005-07-07 | アバニール・ファーマシューティカルズ | ｎ−ドコサノールによるウイルス阻害 |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| EP1440072A4 (en) * | 2001-10-30 | 2005-02-02 | Conforma Therapeutic Corp | PURINE ANALOGS HAVING HSP90 INHIBITORY ACTIVITY |
| WO2004048380A1 (en) | 2002-11-22 | 2004-06-10 | Ranbaxy Laboratories Limited | Process for the synthesis of ganciclovir |
| RU2233842C1 (ru) * | 2003-01-13 | 2004-08-10 | Петров Владимир Иванович | Производные пурина, обладающие противовирусной активностью |
| US20060234982A1 (en) | 2003-01-14 | 2006-10-19 | Dahl Terrence C | Compositions and methods for combination antiviral therapy |
| US20040200730A1 (en) * | 2003-04-14 | 2004-10-14 | Kyo Jibiki | Hydrometallurgical copper recovery process |
| BRPI0510820A (pt) | 2004-05-19 | 2007-11-27 | Emisphere Tech Inc | composição farmacêutica, forma unitária de dosagem e seus usos |
| TWI471145B (zh) | 2005-06-13 | 2015-02-01 | Bristol Myers Squibb & Gilead Sciences Llc | 單一式藥學劑量型 |
| TWI375560B (en) | 2005-06-13 | 2012-11-01 | Gilead Sciences Inc | Composition comprising dry granulated emtricitabine and tenofovir df and method for making the same |
| JP5571947B2 (ja) * | 2006-03-14 | 2014-08-13 | アルト ソリューションズ インコーポレーテッド | 癌およびその他の疾患の予防および治療 |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| WO2010075517A2 (en) | 2008-12-23 | 2010-07-01 | Pharmasset, Inc. | Nucleoside analogs |
| CN102325783A (zh) | 2008-12-23 | 2012-01-18 | 法莫赛特股份有限公司 | 嘌呤核苷的合成 |
| PA8855601A1 (es) | 2008-12-23 | 2010-07-27 | Forformidatos de nucleósidos | |
| SMT201700412T1 (it) | 2010-03-31 | 2017-11-15 | Gilead Pharmasset Llc | Procedimento per la cristallizzazione di (s)-isopropil 2-(((s)-(perfluorofenossi)(fenossi)fosforil)ammino)propanoato |
| GB201819418D0 (en) | 2018-11-29 | 2019-01-16 | Daniel Calladine Ltd | Anti-viral compositions |
| US20230218644A1 (en) | 2020-04-16 | 2023-07-13 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199574A (en) * | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| US4146715A (en) * | 1975-08-27 | 1979-03-27 | Burroughs Wellcome Co. | 2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines |
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1974
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1975
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- 1975-09-02 IL IL48035A patent/IL48035A/xx unknown
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- 1975-09-02 BG BG032819A patent/BG24815A3/xx unknown
- 1975-09-02 HU HU75WE527A patent/HU176730B/hu unknown
- 1975-09-02 LU LU73304A patent/LU73304A1/xx unknown
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- 1975-09-02 AU AU84459/75A patent/AU503160B2/en not_active Expired
- 1975-09-02 JP JP50106479A patent/JPS5154589A/ja active Granted
- 1975-09-02 DE DE2539963A patent/DE2539963C2/de not_active Expired
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- 1975-09-02 DD DD188132A patent/DD122092A5/xx active Search and Examination
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- 1975-09-02 FI FI752465A patent/FI60709C/fi not_active IP Right Cessation
- 1975-09-02 BE BE159690A patent/BE833006A/xx not_active IP Right Cessation
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- 1975-09-02 AT AT676375A patent/AT354462B/de not_active IP Right Cessation
- 1975-09-02 ZM ZM128/75A patent/ZM12875A1/xx unknown
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- 1976-04-23 AR AR262994A patent/AR220885A1/es active
- 1976-04-28 AR AR262993A patent/AR212914A1/es active
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- 1977-01-24 SU SU772444408A patent/SU700064A3/ru active
- 1977-01-24 SU SU772442252A patent/SU686618A3/ru active
- 1977-01-24 SU SU772442435A patent/SU751325A3/ru active
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