DK166823B1 - Purinforbindelser, fremgangsmaade til fremstilling heraf, samt anvendelse af forbindelserne som farmaceutika - Google Patents

Purinforbindelser, fremgangsmaade til fremstilling heraf, samt anvendelse af forbindelserne som farmaceutika Download PDF

Info

Publication number: DK166823B1
Authority: DK; Denmark
Prior art keywords: oxy; compound; amino; general formula; purine
Prior art date: 1985-12-13

Application number

DK595886A

Other languages

Danish (da)

English (en)

Other versions

DK595886A (da

DK595886D0 (da

Inventor

Paul Graham Wyatt

Michael Raymond Harnden

Original Assignee

Beecham Group Plc

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.)

1985-12-13

Filing date

1986-12-11

Publication date

1993-07-19

1985-12-13 Priority claimed from GB858530813A external-priority patent/GB8530813D0/en

1986-02-10 Priority claimed from GB868603228A external-priority patent/GB8603228D0/en

1986-08-28 Priority claimed from GB868620849A external-priority patent/GB8620849D0/en

1986-10-31 Priority claimed from GB868626041A external-priority patent/GB8626041D0/en

1986-12-11 Application filed by Beecham Group Plc filed Critical Beecham Group Plc

1986-12-11 Publication of DK595886D0 publication Critical patent/DK595886D0/da

1987-06-14 Publication of DK595886A publication Critical patent/DK595886A/da

1993-07-19 Application granted granted Critical

1993-07-19 Publication of DK166823B1 publication Critical patent/DK166823B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 33
239000003814 drug Substances 0.000 title claims abstract description 8
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 115
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 54
-1 hydroxy, amino Chemical group 0.000 claims abstract description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 26
238000002360 preparation method Methods 0.000 claims abstract description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 8
229910019142 PO4 Inorganic materials 0.000 claims abstract description 6
239000010452 phosphate Substances 0.000 claims abstract description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 18
239000000460 chlorine Substances 0.000 claims description 11
125000002252 acyl group Chemical class 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
230000009385 viral infection Effects 0.000 claims description 4
UWCACOXRVYDNEE-UHFFFAOYSA-N 2-amino-9-(3-hydroxypropoxy)-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(OCCCO)C=N2 UWCACOXRVYDNEE-UHFFFAOYSA-N 0.000 claims description 3
LGERQLHLISVRPT-UHFFFAOYSA-N 2-amino-9-[3-hydroxy-2-(hydroxymethyl)propoxy]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(OCC(CO)CO)C=N2 LGERQLHLISVRPT-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 2
125000002015 acyclic group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
150000001733 carboxylic acid esters Chemical group 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
QMVAMZDEARZBRT-UHFFFAOYSA-N 2-[(2-aminopurin-9-yl)oxymethyl]propane-1,3-diol Chemical compound NC1=NC=C2N=CN(OCC(CO)CO)C2=N1 QMVAMZDEARZBRT-UHFFFAOYSA-N 0.000 claims 2
WBYVECBLBRQCCE-RXMQYKEDSA-N (2r)-3-(2-aminopurin-9-yl)oxypropane-1,2-diol Chemical compound NC1=NC=C2N=CN(OC[C@H](O)CO)C2=N1 WBYVECBLBRQCCE-RXMQYKEDSA-N 0.000 claims 1
RVUURJWOGFGXMM-UHFFFAOYSA-N 2-(2-aminopurin-9-yl)oxybutane-1,4-diol Chemical compound NC1=NC=C2N=CN(OC(CO)CCO)C2=N1 RVUURJWOGFGXMM-UHFFFAOYSA-N 0.000 claims 1
ARGAGMONNGMNFI-UHFFFAOYSA-N 2-amino-9-(2,3-dihydroxypropoxy)-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(OCC(O)CO)C=N2 ARGAGMONNGMNFI-UHFFFAOYSA-N 0.000 claims 1
FBMDLCFJQAPBNK-UHFFFAOYSA-N 3-(2-aminopurin-9-yl)oxypropan-1-ol Chemical compound NC1=NC=C2N=CN(OCCCO)C2=N1 FBMDLCFJQAPBNK-UHFFFAOYSA-N 0.000 claims 1
WBYVECBLBRQCCE-UHFFFAOYSA-N 3-(2-aminopurin-9-yl)oxypropane-1,2-diol Chemical compound NC1=NC=C2N=CN(OCC(O)CO)C2=N1 WBYVECBLBRQCCE-UHFFFAOYSA-N 0.000 claims 1
WILWCOALRNYBOO-UHFFFAOYSA-N 3-(2-aminopurin-9-yl)oxypropyl acetate Chemical compound N1=C(N)N=C2N(OCCCOC(=O)C)C=NC2=C1 WILWCOALRNYBOO-UHFFFAOYSA-N 0.000 claims 1
BNHYWKMFVYGYNM-UHFFFAOYSA-N 3-(2-aminopurin-9-yl)oxypropyl benzoate Chemical compound C12=NC(N)=NC=C2N=CN1OCCCOC(=O)C1=CC=CC=C1 BNHYWKMFVYGYNM-UHFFFAOYSA-N 0.000 claims 1
ACLNDNSSROFMMN-UHFFFAOYSA-N 3-[(2-amino-6-oxo-3h-purin-9-yl)oxy]propyl acetate Chemical compound N1C(N)=NC(=O)C2=C1N(OCCCOC(=O)C)C=N2 ACLNDNSSROFMMN-UHFFFAOYSA-N 0.000 claims 1
RYOWDYGUCWBPMC-UHFFFAOYSA-N 3-[(2-amino-6-oxo-3h-purin-9-yl)oxy]propyl hexanoate Chemical compound N1C(N)=NC(=O)C2=C1N(OCCCOC(=O)CCCCC)C=N2 RYOWDYGUCWBPMC-UHFFFAOYSA-N 0.000 claims 1
NVQRNWRCVHDOMM-UHFFFAOYSA-N 4-(2-aminopurin-9-yl)oxybutane-1,2-diol Chemical compound NC1=NC=C2N=CN(OCCC(O)CO)C2=N1 NVQRNWRCVHDOMM-UHFFFAOYSA-N 0.000 claims 1
HWRFTOWHSBECMR-UHFFFAOYSA-N 6-n-[(4-aminophenyl)methyl]-2-n-[[3-(trifluoromethyl)phenyl]methyl]-7h-purine-2,6-diamine Chemical compound C1=CC(N)=CC=C1CNC1=NC(NCC=2C=C(C=CC=2)C(F)(F)F)=NC2=C1NC=N2 HWRFTOWHSBECMR-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
QCXJRISMPUSYTF-UHFFFAOYSA-N OCCCON1C2=NC=NC=C2N=C1 Chemical compound OCCCON1C2=NC=NC=C2N=C1 QCXJRISMPUSYTF-UHFFFAOYSA-N 0.000 claims 1
XCOUNIRIAHYWOO-UHFFFAOYSA-N [2-(acetyloxymethyl)-3-(2-aminopurin-9-yl)oxypropyl] acetate Chemical compound N1=C(N)N=C2N(OCC(COC(C)=O)COC(=O)C)C=NC2=C1 XCOUNIRIAHYWOO-UHFFFAOYSA-N 0.000 claims 1
BPDVRJCMZGPRHI-UHFFFAOYSA-N [3-(2-aminopurin-9-yl)oxy-4-butanoyloxybutyl] butanoate Chemical compound N1=C(N)N=C2N(OC(COC(=O)CCC)CCOC(=O)CCC)C=NC2=C1 BPDVRJCMZGPRHI-UHFFFAOYSA-N 0.000 claims 1
DYAHUBFMJQEOKT-UHFFFAOYSA-N [4-acetyloxy-3-(2-aminopurin-9-yl)oxybutyl] acetate Chemical compound N1=C(N)N=C2N(OC(COC(C)=O)CCOC(=O)C)C=NC2=C1 DYAHUBFMJQEOKT-UHFFFAOYSA-N 0.000 claims 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
150000001804 chlorine Chemical class 0.000 claims 1
231100000433 cytotoxic Toxicity 0.000 claims 1
230000001472 cytotoxic effect Effects 0.000 claims 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
238000006467 substitution reaction Methods 0.000 claims 1
230000001988 toxicity Effects 0.000 claims 1
231100000419 toxicity Toxicity 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 25
229910052739 hydrogen Inorganic materials 0.000 abstract description 10
239000001257 hydrogen Substances 0.000 abstract description 10
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
230000000840 anti-viral effect Effects 0.000 abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
150000002431 hydrogen Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000002329 infrared spectrum Methods 0.000 description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
241000700605 Viruses Species 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
210000004027 cell Anatomy 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
238000010511 deprotection reaction Methods 0.000 description 8
239000006188 syrup Substances 0.000 description 8
235000020357 syrup Nutrition 0.000 description 8
230000000120 cytopathologic effect Effects 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
229920000936 Agarose Polymers 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
108091003079 Bovine Serum Albumin Proteins 0.000 description 5
241000700588 Human alphaherpesvirus 1 Species 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
239000012894 fetal calf serum Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
238000010992 reflux Methods 0.000 description 5
241000701085 Human alphaherpesvirus 3 Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000013553 cell monolayer Substances 0.000 description 4
230000020176 deacylation Effects 0.000 description 4
238000005947 deacylation reaction Methods 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
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 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000701074 Human alphaherpesvirus 2 Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
230000010933 acylation Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
230000003013 cytotoxicity Effects 0.000 description 3
231100000135 cytotoxicity Toxicity 0.000 description 3
IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000002458 infectious effect Effects 0.000 description 3
SJUZRTBKERGCTK-UHFFFAOYSA-N n-(4,6-dichloro-2-formamidopyrimidin-5-yl)formamide Chemical compound ClC1=NC(NC=O)=NC(Cl)=C1NC=O SJUZRTBKERGCTK-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000002335 preservative effect Effects 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
239000002356 single layer Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 description 2
NAJUETUQIDQWTL-UHFFFAOYSA-N 2-(3-phenylmethoxypropoxy)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OCCCOCC1=CC=CC=C1 NAJUETUQIDQWTL-UHFFFAOYSA-N 0.000 description 2
MTVWFVDWRVYDOR-UHFFFAOYSA-N 3,4-Dihydroxyphenylglycol Chemical compound OCC(O)C1=CC=C(O)C(O)=C1 MTVWFVDWRVYDOR-UHFFFAOYSA-N 0.000 description 2
ZXWGHENZKVQKPX-UHFFFAOYSA-N 4,6-dichloropyrimidine-2,5-diamine Chemical compound NC1=NC(Cl)=C(N)C(Cl)=N1 ZXWGHENZKVQKPX-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
208000009889 Herpes Simplex Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000713325 Visna/maedi virus Species 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
244000309466 calf Species 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 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
239000000284 extract Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
CXDRPCDUTWYDIQ-UHFFFAOYSA-N n-[6-chloro-9-(3-phenylmethoxypropoxy)purin-2-yl]formamide Chemical compound C1=NC=2C(Cl)=NC(NC=O)=NC=2N1OCCCOCC1=CC=CC=C1 CXDRPCDUTWYDIQ-UHFFFAOYSA-N 0.000 description 2
CFZZKAWHXHOCNL-UHFFFAOYSA-N n-[6-chloro-9-[3-phenylmethoxy-2-(phenylmethoxymethyl)propoxy]purin-2-yl]formamide Chemical compound C1=NC=2C(Cl)=NC(NC=O)=NC=2N1OCC(COCC=1C=CC=CC=1)COCC1=CC=CC=C1 CFZZKAWHXHOCNL-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
NMMPNPCPOWXIMY-UHFFFAOYSA-N o-(3-phenylmethoxypropyl)hydroxylamine Chemical compound NOCCCOCC1=CC=CC=C1 NMMPNPCPOWXIMY-UHFFFAOYSA-N 0.000 description 2
FFYAYUWRPXIJFJ-UHFFFAOYSA-N o-(3-phenylmethoxypropyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCCCOCC1=CC=CC=C1 FFYAYUWRPXIJFJ-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000002953 phosphate buffered saline Substances 0.000 description 2
230000000865 phosphorylative effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
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 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 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
230000000699 topical effect Effects 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
YMBVEKISMARXEM-UHFFFAOYSA-N 2-amino-2-cyanoacetamide;hydrochloride Chemical compound Cl.N#CC(N)C(N)=O YMBVEKISMARXEM-UHFFFAOYSA-N 0.000 description 1
NJDPBWLDVFCXNP-UHFFFAOYSA-N 2-cyanoethyl dihydrogen phosphate Chemical group OP(O)(=O)OCCC#N NJDPBWLDVFCXNP-UHFFFAOYSA-N 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
FUCYABRIJPUVAT-UHFFFAOYSA-N 3-phenylmethoxypropan-1-ol Chemical compound OCCCOCC1=CC=CC=C1 FUCYABRIJPUVAT-UHFFFAOYSA-N 0.000 description 1
UUARXJNAXZTHQO-UHFFFAOYSA-N 5-(benzoylcarbamothioylamino)-1-(3-phenylmethoxypropoxy)imidazole-4-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NC1=C(C(=O)N)N=CN1OCCCOCC1=CC=CC=C1 UUARXJNAXZTHQO-UHFFFAOYSA-N 0.000 description 1
HSJKUGYIZMMHJC-UHFFFAOYSA-N 5-amino-1-(3-phenylmethoxypropoxy)imidazole-4-carboxamide Chemical compound NC1=C(C(=O)N)N=CN1OCCCOCC1=CC=CC=C1 HSJKUGYIZMMHJC-UHFFFAOYSA-N 0.000 description 1
HPCYGBQBGKTNTI-UHFFFAOYSA-N 6-ethoxy-9-(3-phenylmethoxypropoxy)purin-2-amine Chemical compound C1=NC=2C(OCC)=NC(N)=NC=2N1OCCCOCC1=CC=CC=C1 HPCYGBQBGKTNTI-UHFFFAOYSA-N 0.000 description 1
OOPHRECJSLUWEV-UHFFFAOYSA-N 9-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]purine-2,6-diamine Chemical compound C1OC(C)(C)OCC1CON1C2=NC(N)=NC(N)=C2N=C1 OOPHRECJSLUWEV-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UNEMZSPYOHYULT-UHFFFAOYSA-N CC(C)OClF Chemical compound CC(C)OClF UNEMZSPYOHYULT-UHFFFAOYSA-N 0.000 description 1
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
HOOWCUZPEFNHDT-UHFFFAOYSA-N DHPG Natural products OC(=O)C(N)C1=CC(O)=CC(O)=C1 HOOWCUZPEFNHDT-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
241000725303 Human immunodeficiency virus Species 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 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
241000713666 Lentivirus Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700584 Simplexvirus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
208000010094 Visna Diseases 0.000 description 1
229960004150 aciclovir Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
239000002585 base Substances 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
239000012470 diluted sample Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
230000004927 fusion Effects 0.000 description 1
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 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
239000012362 glacial acetic acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
JHFSAYYKEARTQH-UHFFFAOYSA-N n-[4-chloro-2-formamido-6-(3-phenylmethoxypropoxyamino)pyrimidin-5-yl]formamide Chemical compound ClC1=NC(NC=O)=NC(NOCCCOCC=2C=CC=CC=2)=C1NC=O JHFSAYYKEARTQH-UHFFFAOYSA-N 0.000 description 1
MZDWIZNUQGKVOH-UHFFFAOYSA-N n-[4-chloro-2-formamido-6-[[3-phenylmethoxy-2-(phenylmethoxymethyl)propoxy]amino]pyrimidin-5-yl]formamide Chemical compound ClC1=NC(NC=O)=NC(NOCC(COCC=2C=CC=CC=2)COCC=2C=CC=CC=2)=C1NC=O MZDWIZNUQGKVOH-UHFFFAOYSA-N 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
SILQQWDDGULIBM-UHFFFAOYSA-N o-[3-phenylmethoxy-2-(phenylmethoxymethyl)propyl]hydroxylamine Chemical compound C=1C=CC=CC=1COCC(CON)COCC1=CC=CC=C1 SILQQWDDGULIBM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000003362 replicative effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
210000003501 vero cell Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Sub-Exchange Stations And Push- Button Telephones (AREA)
Saccharide Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Superconductors And Manufacturing Methods Therefor (AREA)
Jib Cranes (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)
Cephalosporin Compounds (AREA)
Nonmetallic Welding Materials (AREA)
General Factory Administration (AREA)
Compositions Of Oxide Ceramics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK595886A 1985-12-13 1986-12-11 Purinforbindelser, fremgangsmaade til fremstilling heraf, samt anvendelse af forbindelserne som farmaceutika DK166823B1 (da)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
GB858530813A GB8530813D0 (en)	1985-12-13	1985-12-13	Compounds
GB8530813		1985-12-13
GB868603228A GB8603228D0 (en)	1986-02-10	1986-02-10	Compounds
GB8603228		1986-02-10
GB8620849		1986-08-28
GB868620849A GB8620849D0 (en)	1986-08-28	1986-08-28	Compounds
GB868626041A GB8626041D0 (en)	1986-10-31	1986-10-31	Compounds
GB8626041		1986-10-31

Publications (3)

Publication Number	Publication Date
DK595886D0 DK595886D0 (da)	1986-12-11
DK595886A DK595886A (da)	1987-06-14
DK166823B1 true DK166823B1 (da)	1993-07-19

Family

ID=27449713

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK595886A DK166823B1 (da)	1985-12-13	1986-12-11	Purinforbindelser, fremgangsmaade til fremstilling heraf, samt anvendelse af forbindelserne som farmaceutika

Country Status (19)

Country	Link
EP (1)	EP0242482B1 (fr)
JP (1)	JPH085886B2 (fr)
KR (1)	KR940010033B1 (fr)
AT (1)	ATE127466T1 (fr)
AU (1)	AU599066B2 (fr)
CA (1)	CA1296726C (fr)
DE (1)	DE3650384T2 (fr)
DK (1)	DK166823B1 (fr)
ES (1)	ES2076139T3 (fr)
FI (1)	FI85143C (fr)
GR (1)	GR3018105T3 (fr)
HU (1)	HU200461B (fr)
IL (1)	IL80947A (fr)
MA (1)	MA20828A1 (fr)
MY (1)	MY101126A (fr)
NO (1)	NO166226C (fr)
NZ (1)	NZ218598A (fr)
PL (3)	PL150841B1 (fr)
PT (1)	PT83911B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8602346D0 (en) *	1986-01-30	1986-03-05	Wellcome Found	Antiviral combinations
US4965270A (en) *	1987-05-30	1990-10-23	Beecham Group P.L.C.	Purine derivatives
GB8713695D0 (en) *	1987-06-11	1987-07-15	Beecham Group Plc	Process
GB8712744D0 (en) *	1987-05-30	1987-07-01	Beecham Group Plc	Active compounds
GB8724765D0 (en) *	1987-10-22	1987-11-25	Beecham Group Plc	Process
SE8801729D0 (sv) *	1988-05-06	1988-05-06	Astra Ab	Purine derivatives for use in therapy
EP0353955A3 (fr) *	1988-08-02	1991-08-14	Beecham Group Plc	Composés chimiques
DK135489D0 (da) *	1989-03-20	1989-03-20	Gea Farmaceutisk Fabrik As	Fremgangsmaade til fremstilling af 9-substituerede guaninderivater og mellemprodukter til brug ved fremgangsmaaden
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
GB8918827D0 (en) *	1989-08-17	1989-09-27	Beecham Group Plc	Novel compounds
US5252575A (en) *	1989-08-17	1993-10-12	Beecham Group P.L.C.	Antiviral purine derivatives with improved gastrointestinal absorption
GB9107896D0 (en) *	1991-04-13	1991-05-29	Smithkline Beecham Plc	Pharmaceuticals
JP2720681B2 (ja) *	1992-01-06	1998-03-04	株式会社村田製作所	移動体の移動検出装置
GB9402161D0 (en) *	1994-02-04	1994-03-30	Wellcome Found	Chloropyrimidine intermediates

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4347360A (en) *	1980-09-16	1982-08-31	Ens Bio Logicals Inc.	Ring open nucleoside analogues
KR890001487B1 (ko) *	1982-10-14	1989-05-04	더 웰컴 파운데이숀 리미티드	푸린 유도체의 제조방법
IL72173A0 (en) *	1983-06-24	1984-10-31	Merck & Co Inc	Guanine derivatives,their preparation and pharmaceutical compositions containing them
CA1330797C (fr) *	1984-12-12	1994-07-19	David J. Morgans, Jr.	Derives alkoxymethylether et alkoxymethylester

1986
- 1986-12-10 MY MYPI86000187A patent/MY101126A/en unknown
- 1986-12-11 IL IL80947A patent/IL80947A/xx not_active IP Right Cessation
- 1986-12-11 AU AU66443/86A patent/AU599066B2/en not_active Ceased
- 1986-12-11 PT PT83911A patent/PT83911B/pt not_active IP Right Cessation
- 1986-12-11 EP EP86309667A patent/EP0242482B1/fr not_active Expired - Lifetime
- 1986-12-11 CA CA000525073A patent/CA1296726C/fr not_active Expired - Fee Related
- 1986-12-11 PL PL1986262930A patent/PL150841B1/pl unknown
- 1986-12-11 AT AT86309667T patent/ATE127466T1/de not_active IP Right Cessation
- 1986-12-11 DK DK595886A patent/DK166823B1/da not_active IP Right Cessation
- 1986-12-11 NZ NZ218598A patent/NZ218598A/xx unknown
- 1986-12-11 NO NO865014A patent/NO166226C/no unknown
- 1986-12-11 ES ES86309667T patent/ES2076139T3/es not_active Expired - Lifetime
- 1986-12-11 PL PL1986272031A patent/PL150925B1/pl unknown
- 1986-12-11 KR KR1019860010590A patent/KR940010033B1/ko not_active Expired - Fee Related
- 1986-12-11 DE DE3650384T patent/DE3650384T2/de not_active Expired - Lifetime
- 1986-12-11 PL PL1986272032A patent/PL150926B1/pl unknown
- 1986-12-12 HU HU865196A patent/HU200461B/hu not_active IP Right Cessation
- 1986-12-12 FI FI865075A patent/FI85143C/fi not_active IP Right Cessation
- 1986-12-12 JP JP61295096A patent/JPH085886B2/ja not_active Expired - Lifetime
- 1986-12-12 MA MA21060A patent/MA20828A1/fr unknown
1995
- 1995-11-16 GR GR950403221T patent/GR3018105T3/el unknown

Also Published As

Publication number	Publication date
ES2076139T3 (es)	1995-11-01
PT83911B (pt)	1989-05-12
NO865014L (no)	1987-06-15
FI85143B (fi)	1991-11-29
AU599066B2 (en)	1990-07-12
PL262930A1 (en)	1988-09-01
NO865014D0 (no)	1986-12-11
PL150926B1 (en)	1990-07-31
DE3650384D1 (de)	1995-10-12
HUT43069A (en)	1987-09-28
AU6644386A (en)	1987-06-18
JPS62181279A (ja)	1987-08-08
DK595886A (da)	1987-06-14
PT83911A (en)	1987-01-01
JPH085886B2 (ja)	1996-01-24
NO166226C (no)	1991-06-19
ATE127466T1 (de)	1995-09-15
NO166226B (no)	1991-03-11
MA20828A1 (fr)	1987-07-01
EP0242482B1 (fr)	1995-09-06
PL272032A1 (en)	1989-01-05
CA1296726C (fr)	1992-03-03
EP0242482A3 (en)	1989-02-08
EP0242482A2 (fr)	1987-10-28
FI865075A7 (fi)	1987-06-14
FI865075A0 (fi)	1986-12-12
FI85143C (fi)	1992-03-10
KR940010033B1 (ko)	1994-10-21
NZ218598A (en)	1990-10-26
HU200461B (en)	1990-06-28
PL272031A1 (en)	1989-01-05
IL80947A (en)	1990-01-18
KR880005129A (ko)	1988-06-28
PL150841B1 (en)	1990-07-31
PL150925B1 (en)	1990-07-31
DE3650384T2 (de)	1996-06-13
GR3018105T3 (en)	1996-02-29
DK595886D0 (da)	1986-12-11
MY101126A (en)	1991-07-31

Legal Events

Date	Code	Title	Description
1993-07-19	B1	Patent granted (law 1993)
1996-08-19	PBP	Patent lapsed

Publication	Publication Date	Title
DK167019B1 (da)	1993-08-16	2-aminopurinderivater, fremgangsmaade til fremstilling heraf, farmaceutiske praeparater indeholdende disse forbindelser samt anvendelse heraf
US6573378B1 (en)	2003-06-03	Antiviral guanine derivatives
KR0128661B1 (ko)	1998-04-04	시클로부탄 유도체 및 그 제조 방법
FI60709B (fi)	1981-11-30	Analogifoerfarande foer framstaellning av 9-substituerade puriner anvaendbara saosom antivirala medel
EP0243670B1 (fr)	1992-07-22	Composés de purine et pyrimidine et leur usage comme agents antiviraux
US6057305A (en)	2000-05-02	Antiretroviral enantiomeric nucleotide analogs
FI90422B (fi)	1993-10-29	Menetelmä uusien terapeuttisesti käyttökelpoisten purinyyli- ja pyrimidinyylisyklobutaanijohdannaisten valmistamiseksi
CA2032422A1 (fr)	1991-06-21	Analogues d'oxetanylpurines et d'oxetanylpyrimidines
JPH0680061B2 (ja)	1994-10-12	新規なプリン誘導体
KR940010033B1 (ko)	1994-10-21	항비루스 활성을 갖는 화합물의 제조방법
US5356886A (en)	1994-10-18	Antiviral phosphono-alken derivatives of purines
US5153352A (en)	1992-10-06	Process for preparation of intermediates of carbocyclic nucleoside analogs
WO1993019075A1 (fr)	1993-09-30	Derives acides phosphoniques antiviraux d'analogues de purine
DE3852008T2 (de)	1995-03-23	Verbindungen.
Lee et al.	1987	Antitumor agents. 86. Synthesis and cytotoxicity of. alpha.-methylene-. gamma.-lactone-bearing purines
US5246931A (en)	1993-09-21	Carbocyclic nucleoside analogs
IE910908A1 (en)	1991-09-25	Substituted purines, processes for their preparation and¹their use as antiviral agents
JP3072600B2 (ja)	2000-07-31	新規化合物、その製法及びそれを含む医薬組成物
DK147596B (da)	1984-10-15	Analogifremgangsmaade til fremstilling af 7-alkoxymethylpuriner
JP2632646B2 (ja)	1997-07-23	新規なシクロブタン誘導体及びその製造法
JPH05178746A (ja)	1993-07-20	抗ウイルス剤
NL8921278A (nl)	1990-10-01	Nieuw cyclobutaanderivaat en werkwijze voor het bereiden ervan.
CS199666B2 (cs)	1980-07-31	Způsob přípravy 9-substituovaných purinů
JPH06206880A (ja)	1994-07-26	新規シクロペンテン誘導体
HK136493A (en)	1993-12-17	Purine and pyrimidine compounds and their use as anti-viral agents