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

DK595886D0 (da

DK595886A (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
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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
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230000000120 cytopathologic effect Effects 0.000 description 7
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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
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238000004458 analytical method Methods 0.000 description 6
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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
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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
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241000700588 Human alphaherpesvirus 1 Species 0.000 description 5
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239000012894 fetal calf serum Substances 0.000 description 5
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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
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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
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
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229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
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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
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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IRUNKQSGDBYUDC-UHFFFAOYSA-N diethoxymethyl acetate Chemical compound CCOC(OCC)OC(C)=O IRUNKQSGDBYUDC-UHFFFAOYSA-N 0.000 description 3
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239000011591 potassium Substances 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
- 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)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Virology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Superconductors And Manufacturing Methods Therefor (AREA)
Jib Cranes (AREA)
Cephalosporin Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Compositions Of Oxide Ceramics (AREA)
Nonmetallic Welding Materials (AREA)
General Factory Administration (AREA)
Saccharide Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 (pl)
JP (1)	JPH085886B2 (pl)
KR (1)	KR940010033B1 (pl)
AT (1)	ATE127466T1 (pl)
AU (1)	AU599066B2 (pl)
CA (1)	CA1296726C (pl)
DE (1)	DE3650384T2 (pl)
DK (1)	DK166823B1 (pl)
ES (1)	ES2076139T3 (pl)
FI (1)	FI85143C (pl)
GR (1)	GR3018105T3 (pl)
HU (1)	HU200461B (pl)
IL (1)	IL80947A (pl)
MA (1)	MA20828A1 (pl)
MY (1)	MY101126A (pl)
NO (1)	NO166226C (pl)
NZ (1)	NZ218598A (pl)
PL (3)	PL150926B1 (pl)
PT (1)	PT83911B (pl)

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
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
US4965270A (en) *	1987-05-30	1990-10-23	Beecham Group P.L.C.	Purine derivatives
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 (en) *	1988-08-02	1991-08-14	Beecham Group Plc	Novel compounds
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
US5252575A (en) *	1989-08-17	1993-10-12	Beecham Group P.L.C.	Antiviral purine derivatives with improved gastrointestinal absorption
GB8918827D0 (en) *	1989-08-17	1989-09-27	Beecham Group Plc	Novel compounds
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
DE3376326D1 (en) *	1982-10-14	1988-05-26	Wellcome Found	Antiviral purine derivatives
IL72173A0 (en) *	1983-06-24	1984-10-31	Merck & Co Inc	Guanine derivatives,their preparation and pharmaceutical compositions containing them
ES8705889A1 (es) *	1984-12-12	1987-06-01	Syntex Inc	Un metodo para preparar eteres alcaximetilicos y esteres alcoximetilicos de derivados de guananina.

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

Also Published As

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

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 (en)	1992-07-22	Purine and pyrimidine compounds and their use as anti-viral agents
US6057305A (en)	2000-05-02	Antiretroviral enantiomeric nucleotide analogs
FI90422B (fi)	1993-10-29	Menetelmä uusien terapeuttisesti käyttökelpoisten purinyyli- ja pyrimidinyylisyklobutaanijohdannaisten valmistamiseksi
JPH0680061B2 (ja)	1994-10-12	新規なプリン誘導体
CA2032422A1 (en)	1991-06-21	Analogs of oxetanyl purines and pyrimidines
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 (en)	1993-09-30	Antiviral phosphonic acid derivatives of purine analogues
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