CS263951B1 - 9-(phosponylmethoxyalkyl)adenines and method of their preparation - Google Patents
9-(phosponylmethoxyalkyl)adenines and method of their preparation Download PDFInfo
- Publication number
- CS263951B1 CS263951B1 CS853017A CS301785A CS263951B1 CS 263951 B1 CS263951 B1 CS 263951B1 CS 853017 A CS853017 A CS 853017A CS 301785 A CS301785 A CS 301785A CS 263951 B1 CS263951 B1 CS 263951B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- adenine
- compound
- dimethylformamide
- compounds
- Prior art date
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- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- -1 methylene, ethylene, propylene, ethylidene, methoxyethylene, benzyloxyethylene Chemical group 0.000 claims abstract description 23
- UAYCAARGGQRWMQ-UHFFFAOYSA-N 1-ethenoxy-1-ethoxyethane Chemical group CCOC(C)OC=C UAYCAARGGQRWMQ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000004255 ion exchange chromatography Methods 0.000 claims description 2
- NGVNAUIRSOXAJB-UHFFFAOYSA-N prop-1-ene-1,2-diol Chemical group CC(O)=CO NGVNAUIRSOXAJB-UHFFFAOYSA-N 0.000 claims 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 claims 1
- NMVZYNYULBGMRI-UHFFFAOYSA-N 1-methoxybuta-1,2-diene Chemical group COC=C=CC NMVZYNYULBGMRI-UHFFFAOYSA-N 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 230000000840 anti-viral effect Effects 0.000 abstract description 3
- 230000004071 biological effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229930024421 Adenine Natural products 0.000 description 21
- 229960000643 adenine Drugs 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910003002 lithium salt Inorganic materials 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 159000000002 lithium salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000700605 Viruses Species 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 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 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000000120 cytopathologic effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- BYUNYALHUMSCSA-UHFFFAOYSA-N 2-ethenoxyoxane Chemical group C=COC1CCCCO1 BYUNYALHUMSCSA-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- WGQMNJYLZXTHIN-UHFFFAOYSA-N dimethoxyphosphorylmethyl 4-methylbenzenesulfonate Chemical compound COP(=O)(OC)COS(=O)(=O)C1=CC=C(C)C=C1 WGQMNJYLZXTHIN-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 210000003292 kidney cell Anatomy 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- XVNBPVQOGWKDEA-UHFFFAOYSA-N 3-(6-aminopurin-9-yl)-2-phenylmethoxypropan-1-ol Chemical compound C1=NC=2C(N)=NC=NC=2N1CC(CO)OCC1=CC=CC=C1 XVNBPVQOGWKDEA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- TYBWABJIIOVYOR-UHFFFAOYSA-N OCC(C(O)=O)OP(=O)=O Chemical compound OCC(C(O)=O)OP(=O)=O TYBWABJIIOVYOR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- SUPKOOSCJHTBAH-UHFFFAOYSA-N adefovir Chemical compound NC1=NC=NC2=C1N=CN2CCOCP(O)(O)=O SUPKOOSCJHTBAH-UHFFFAOYSA-N 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- FZXSSJIKXCFPDP-UHFFFAOYSA-N chloro(dichlorophosphoryl)methane Chemical compound ClCP(Cl)(Cl)=O FZXSSJIKXCFPDP-UHFFFAOYSA-N 0.000 description 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- UOEFFQWLRUBDME-UHFFFAOYSA-N diethoxyphosphorylmethyl 4-methylbenzenesulfonate Chemical compound CCOP(=O)(OCC)COS(=O)(=O)C1=CC=C(C)C=C1 UOEFFQWLRUBDME-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical group C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Inorganic materials [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- DTMFTBZNVFUECB-UHFFFAOYSA-N n-[9-(2-hydroxyethyl)purin-6-yl]benzamide Chemical compound N1=CN=C2N(CCO)C=NC2=C1NC(=O)C1=CC=CC=C1 DTMFTBZNVFUECB-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 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 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 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 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS853017A CS263951B1 (en) | 1985-04-25 | 1985-04-25 | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
| DK198601678A DK173625B1 (da) | 1985-04-25 | 1986-04-11 | 9-(fosfonylmethoxyalkyl)adeniner, fremgangsmåde til fremstilling og anvendelse af samme |
| AT86302822T ATE78259T1 (de) | 1985-04-25 | 1986-04-16 | 9-(phosphonylmethoxyalkyl)-adenine, verfahren zu ihrer herstellung und ihre verwendung. |
| EP86302822A EP0206459B1 (en) | 1985-04-25 | 1986-04-16 | 9-(phosphonylmethoxyalkyl) adenines, method for their preparation and their use |
| DE8686302822T DE3686002T2 (de) | 1985-04-25 | 1986-04-16 | 9-(phosphonylmethoxyalkyl)-adenine, verfahren zu ihrer herstellung und ihre verwendung. |
| AU56328/86A AU580151B2 (en) | 1985-04-25 | 1986-04-17 | 9-(phosphonylmethoxyalkyl) adenines, the method of preparation and utilization thereof |
| NZ215925A NZ215925A (en) | 1985-04-25 | 1986-04-23 | 9-(phosphonylmethoxyalkyl)adenines |
| CA000507444A CA1295614C (en) | 1985-04-25 | 1986-04-24 | 9-(phosphonylmethoxyalkyl)adenines, the method of preparation and utilization thereof |
| NO861621A NO174510B (no) | 1985-04-25 | 1986-04-24 | Anlogifremgangsmaate for fremstilling av terapeutisk aktivt 9-(2- fosfonylmethoxyethyl)-adenin |
| JP61093514A JPS61275289A (ja) | 1985-04-25 | 1986-04-24 | ９−（ホスホニルメトキシアルキル）アデニン，その製造法及びその利用 |
| US06/856,299 US4808716A (en) | 1985-04-25 | 1986-04-25 | 9-(phosponylmethoxyalkyl) adenines, the method of preparation and utilization thereof |
| EG243/86A EG18079A (en) | 1985-04-25 | 1986-04-27 | Process for preparing of 9-(phosphonylmetoxya-lkyl)adenines and utilisation thereof |
| HK213296A HK213296A (en) | 1985-04-25 | 1996-12-05 | 9-(phosphonylmethoxyalkyl) adenines, method for their preparation and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS853017A CS263951B1 (en) | 1985-04-25 | 1985-04-25 | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS263951B1 true CS263951B1 (en) | 1989-05-12 |
Family
ID=5369028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS853017A CS263951B1 (en) | 1985-04-25 | 1985-04-25 | 9-(phosponylmethoxyalkyl)adenines and method of their preparation |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4808716A (Direct) |
| EP (1) | EP0206459B1 (Direct) |
| JP (1) | JPS61275289A (Direct) |
| AT (1) | ATE78259T1 (Direct) |
| AU (1) | AU580151B2 (Direct) |
| CA (1) | CA1295614C (Direct) |
| CS (1) | CS263951B1 (Direct) |
| DE (1) | DE3686002T2 (Direct) |
| DK (1) | DK173625B1 (Direct) |
| EG (1) | EG18079A (Direct) |
| HK (1) | HK213296A (Direct) |
| NO (1) | NO174510B (Direct) |
| NZ (1) | NZ215925A (Direct) |
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| IL84477A (en) * | 1986-11-18 | 1995-12-08 | Bristol Myers Squibb Co | History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them |
| US5247085A (en) * | 1987-11-30 | 1993-09-21 | Beecham Group P.L.C. | Antiviral purine compounds |
| IL88518A (en) * | 1987-11-30 | 1994-02-27 | Beecham Group Plc | 3-(phosphoryl methoxyethoxy) -purine derivatives, their preparation and pharmaceutical compositions containing them |
| EP0335770B1 (en) * | 1988-04-01 | 1997-01-15 | Merrell Pharmaceuticals Inc. | Novel fluorophosphonate nucleotide derivatives |
| EP0339161A1 (en) * | 1988-04-01 | 1989-11-02 | Merrell Dow Pharmaceuticals Inc. | Novel fluorophosphonate nucleotide derivatives |
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| EP0353955A3 (en) * | 1988-08-02 | 1991-08-14 | Beecham Group Plc | Novel compounds |
| US5744600A (en) * | 1988-11-14 | 1998-04-28 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Phosphonomethoxy carbocyclic nucleosides and nucleotides |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| US5688778A (en) * | 1989-05-15 | 1997-11-18 | Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic | Nucleoside analogs |
| GB8912043D0 (en) * | 1989-05-25 | 1989-07-12 | Beecham Group Plc | Novel compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
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| GB2150570B (en) * | 1983-05-24 | 1987-04-08 | Stanford Res Inst Int | Novel antiviral agents |
| AU8092587A (en) * | 1986-11-18 | 1988-05-19 | Bristol-Myers Squibb Company | Synthesis of purin-9-ylalkylenoxymethyl phosphonic acids |
-
1985
- 1985-04-25 CS CS853017A patent/CS263951B1/cs not_active IP Right Cessation
-
1986
- 1986-04-11 DK DK198601678A patent/DK173625B1/da not_active IP Right Cessation
- 1986-04-16 DE DE8686302822T patent/DE3686002T2/de not_active Expired - Lifetime
- 1986-04-16 AT AT86302822T patent/ATE78259T1/de not_active IP Right Cessation
- 1986-04-16 EP EP86302822A patent/EP0206459B1/en not_active Expired - Lifetime
- 1986-04-17 AU AU56328/86A patent/AU580151B2/en not_active Expired
- 1986-04-23 NZ NZ215925A patent/NZ215925A/xx unknown
- 1986-04-24 JP JP61093514A patent/JPS61275289A/ja active Granted
- 1986-04-24 CA CA000507444A patent/CA1295614C/en not_active Expired - Lifetime
- 1986-04-24 NO NO861621A patent/NO174510B/no unknown
- 1986-04-25 US US06/856,299 patent/US4808716A/en not_active Expired - Lifetime
- 1986-04-27 EG EG243/86A patent/EG18079A/xx active
-
1996
- 1996-12-05 HK HK213296A patent/HK213296A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO174510B (no) | 1994-02-07 |
| EG18079A (en) | 1992-06-30 |
| DK173625B1 (da) | 2001-05-07 |
| HK213296A (en) | 1996-12-06 |
| DE3686002D1 (de) | 1992-08-20 |
| JPS61275289A (ja) | 1986-12-05 |
| NO861621L (no) | 1986-10-27 |
| JPH0433798B2 (Direct) | 1992-06-04 |
| US4808716A (en) | 1989-02-28 |
| ATE78259T1 (de) | 1992-08-15 |
| AU5632886A (en) | 1986-10-30 |
| EP0206459A2 (en) | 1986-12-30 |
| DK167886D0 (da) | 1986-04-11 |
| AU580151B2 (en) | 1989-01-05 |
| EP0206459A3 (en) | 1987-05-20 |
| EP0206459B1 (en) | 1992-07-15 |
| NO174510C (Direct) | 1994-05-18 |
| DE3686002T2 (de) | 1992-12-17 |
| NZ215925A (en) | 1989-01-27 |
| DK167886A (da) | 1986-10-26 |
| CA1295614C (en) | 1992-02-11 |
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| Date | Code | Title | Description |
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| MK4A | Patent expired |
Effective date: 20000425 |