DD206781A5 - Verfahren zur herstellung von purinderivaten - Google Patents

Verfahren zur herstellung von purinderivaten Download PDF

Info

Publication number: DD206781A5
Authority: DD; German Democratic Republic
Prior art keywords: propoxymethyl; guanine; hydrogen; purine; hydroxy
Prior art date: 1982-02-01

Application number

DD83247593A

Other languages

German (de)

English (en)

Inventor

Julien P H Verheyden

John C Martin

Original Assignee

Syntex Inc

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.)

1982-02-01

Filing date

1983-01-31

Publication date

1984-02-08

1983-01-31 Application filed by Syntex Inc filed Critical Syntex Inc

1984-02-08 Publication of DD206781A5 publication Critical patent/DD206781A5/de

Links

150000003212 purines Chemical class 0.000 title claims abstract description 7
229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims abstract description 6
238000004519 manufacturing process Methods 0.000 title abstract description 7
-1 1-ADAMANTYL Chemical class 0.000 claims abstract description 185
239000001257 hydrogen Substances 0.000 claims abstract description 65
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 65
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
150000002431 hydrogen Chemical class 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims abstract description 3
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 248
150000001875 compounds Chemical class 0.000 claims description 154
238000000034 method Methods 0.000 claims description 32
238000002360 preparation method Methods 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
COELUGODEFADMG-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-octanoyloxypropyl] octanoate Chemical compound N1=C(N)NC(=O)C2=C1N(COC(COC(=O)CCCCCCC)COC(=O)CCCCCCC)C=N2 COELUGODEFADMG-UHFFFAOYSA-N 0.000 claims description 3
NSZKHEYZLNPIEJ-UHFFFAOYSA-N [3-acetyloxy-2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]propyl] acetate Chemical compound N1C(N)=NC(=O)C2=C1N(COC(COC(C)=O)COC(=O)C)C=N2 NSZKHEYZLNPIEJ-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
PJWVIYVXUNFHQK-UHFFFAOYSA-N [2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]-3-(2,2-dimethylpropanoyloxy)propyl] 2,2-dimethylpropanoate Chemical compound N1=C(N)NC(=O)C2=C1N(COC(COC(=O)C(C)(C)C)COC(=O)C(C)(C)C)C=N2 PJWVIYVXUNFHQK-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 abstract description 6
SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 abstract description 2
DWPIPTNBOVJYAD-BQKDNTBBSA-N (5s,7r)-3-aminoadamantan-1-ol Chemical compound C([C@H](C1)C2)[C@@H]3CC2(N)CC1(O)C3 DWPIPTNBOVJYAD-BQKDNTBBSA-N 0.000 abstract 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical class [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 47
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 42
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
241001529453 unidentified herpesvirus Species 0.000 description 19
239000002904 solvent Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
241000700605 Viruses Species 0.000 description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
208000015181 infectious disease Diseases 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
150000005690 diesters Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
239000002585 base Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
208000036142 Viral infection Diseases 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 6
125000000468 ketone group Chemical group 0.000 description 6
239000000047 product Substances 0.000 description 6
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
230000009385 viral infection Effects 0.000 description 6
OBOHMJWDFPBPKD-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 OBOHMJWDFPBPKD-UHFFFAOYSA-N 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
239000000908 ammonium hydroxide Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
239000003380 propellant Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
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 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
229930194542 Keto Natural products 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000008065 acid anhydrides Chemical class 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000006071 cream Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000007789 gas Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
229920000053 polysorbate 80 Polymers 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
241000271566 Aves Species 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
241000701074 Human alphaherpesvirus 2 Species 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
241000286209 Phasianidae Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
MHSVUSZEHNVFKW-UHFFFAOYSA-N bis-4-nitrophenyl phosphate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OP(=O)(O)OC1=CC=C([N+]([O-])=O)C=C1 MHSVUSZEHNVFKW-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
GILZZWCROUGLIS-UHFFFAOYSA-N n-(9-acetyl-6-oxo-3h-purin-2-yl)acetamide Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N(C(C)=O)C=N2 GILZZWCROUGLIS-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
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239000008194 pharmaceutical composition Substances 0.000 description 3
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239000002244 precipitate Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
239000000375 suspending agent Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
ARLSYSVVBAMYKA-UHFFFAOYSA-N 1,3-bis(phenylmethoxy)propan-2-ol Chemical compound C=1C=CC=CC=1COCC(O)COCC1=CC=CC=C1 ARLSYSVVBAMYKA-UHFFFAOYSA-N 0.000 description 2
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 2
CHDQAAHKXDWKRD-UHFFFAOYSA-N 2-[[2-(n-benzhydryl-4-methoxyanilino)purin-9-yl]methoxy]propane-1,3-diol Chemical compound C1=CC(OC)=CC=C1N(C=1N=C2N(COC(CO)CO)C=NC2=CN=1)C(C=1C=CC=CC=1)C1=CC=CC=C1 CHDQAAHKXDWKRD-UHFFFAOYSA-N 0.000 description 2
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 2
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239000004255 Butylated hydroxyanisole Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
241000283073 Equus caballus Species 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000006758 Marek Disease Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
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KQQAASREQCQBEF-UHFFFAOYSA-N [3-hydroxy-2-[[2-(methylamino)purin-9-yl]methoxy]propyl] dodecanoate Chemical compound N1=C(NC)N=C2N(COC(CO)COC(=O)CCCCCCCCCCC)C=NC2=C1 KQQAASREQCQBEF-UHFFFAOYSA-N 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
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
MIBQYWIOHFTKHD-UHFFFAOYSA-N adamantane-1-carbonyl chloride Chemical compound C1C(C2)CC3CC2CC1(C(=O)Cl)C3 MIBQYWIOHFTKHD-UHFFFAOYSA-N 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
125000006515 benzyloxy alkyl group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
UUCBJORVOQODID-UHFFFAOYSA-N bis(1-adamantyl) 3-[(2-aminopurin-9-yl)methoxy]pentanedioate Chemical compound C1C(C2)CC(C3)CC2CC13OC(=O)CC(CC(=O)OC12CC3CC(CC(C3)C1)C2)OCN1C=NC2=CN=C(N)N=C21 UUCBJORVOQODID-UHFFFAOYSA-N 0.000 description 1
ZOUZMVDVDGNNMR-UHFFFAOYSA-N bis(1-adamantyl) 3-[[2-(n-benzhydryl-4-methoxyanilino)purin-9-yl]methoxy]pentanedioate Chemical compound C1=CC(OC)=CC=C1N(C=1N=C2N(COC(CC(=O)OC34CC5CC(CC(C5)C3)C4)CC(=O)OC34CC5CC(CC(C5)C3)C4)C=NC2=CN=1)C(C=1C=CC=CC=1)C1=CC=CC=C1 ZOUZMVDVDGNNMR-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 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
239000000872 buffer Substances 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
241001233037 catfish Species 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
229960005215 dichloroacetic acid Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012737 fresh medium Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
208000002672 hepatitis B Diseases 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000008309 hydrophilic cream Substances 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
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239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
150000003956 methylamines Chemical group 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
150000002889 oleic acids Chemical class 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Chemical group 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
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238000000746 purification Methods 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
229960005078 sorbitan sesquioleate Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
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238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1786—Unsaturated ethers containing hydroxy or O-metal groups containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD83247593A 1982-02-01 1983-01-31 Verfahren zur herstellung von purinderivaten DD206781A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US34470382A	1982-02-01	1982-02-01
US07/451,262 US5250535A (en)	1982-02-01	1982-12-22	Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent

Publications (1)

Publication Number	Publication Date
DD206781A5 true DD206781A5 (de)	1984-02-08

Family

ID=26994067

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83247593A DD206781A5 (de)	1982-02-01	1983-01-31	Verfahren zur herstellung von purinderivaten

Country Status (20)

Country	Link
US (1)	US5250535A (fi)
EP (1)	EP0085424A3 (fi)
KR (1)	KR890000191B1 (fi)
AU (2)	AU572777B2 (fi)
BR (1)	BR8300475A (fi)
DD (1)	DD206781A5 (fi)
DK (1)	DK29183A (fi)
ES (1)	ES519423A0 (fi)
FI (1)	FI79851C (fi)
GR (1)	GR81321B (fi)
HU (1)	HU193874B (fi)
IL (1)	IL67791A0 (fi)
IN (1)	IN157856B (fi)
NO (1)	NO161372C (fi)
NZ (1)	NZ203128A (fi)
PH (5)	PH19203A (fi)
PL (1)	PL140556B1 (fi)
PT (1)	PT76149B (fi)
RO (3)	RO86234B (fi)
ZW (1)	ZW2583A1 (fi)

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1982
- 1982-12-22 US US07/451,262 patent/US5250535A/en not_active Expired - Fee Related
1983
- 1983-01-25 DK DK29183A patent/DK29183A/da not_active Application Discontinuation
- 1983-01-26 FI FI830254A patent/FI79851C/fi not_active IP Right Cessation
- 1983-01-27 PH PH28429A patent/PH19203A/en unknown
- 1983-01-27 PT PT76149A patent/PT76149B/pt unknown
- 1983-01-31 PL PL1983240367A patent/PL140556B1/pl unknown
- 1983-01-31 HU HU83314A patent/HU193874B/hu not_active IP Right Cessation
- 1983-01-31 ZW ZW25/83A patent/ZW2583A1/xx unknown
- 1983-01-31 KR KR1019830000360A patent/KR890000191B1/ko not_active Expired
- 1983-01-31 NO NO830316A patent/NO161372C/no unknown
- 1983-01-31 RO RO109871A patent/RO86234B/ro unknown
- 1983-01-31 IN IN113/CAL/83A patent/IN157856B/en unknown
- 1983-01-31 BR BR8300475A patent/BR8300475A/pt unknown
- 1983-01-31 EP EP83100886A patent/EP0085424A3/en not_active Withdrawn
- 1983-01-31 IL IL67791A patent/IL67791A0/xx unknown
- 1983-01-31 RO RO83114877A patent/RO89142A/ro unknown
- 1983-01-31 NZ NZ203128A patent/NZ203128A/en unknown
- 1983-01-31 ES ES519423A patent/ES519423A0/es active Granted
- 1983-01-31 RO RO83114876A patent/RO89143A/ro unknown
- 1983-01-31 GR GR70365A patent/GR81321B/el unknown
- 1983-01-31 DD DD83247593A patent/DD206781A5/de not_active IP Right Cessation
- 1983-02-01 AU AU10961/83A patent/AU572777B2/en not_active Ceased
1984
- 1984-06-19 PH PH30841A patent/PH22817A/en unknown
- 1984-06-19 PH PH30839A patent/PH20099A/en unknown
- 1984-06-19 PH PH30840A patent/PH20360A/en unknown
1985
- 1985-05-13 PH PH32259A patent/PH22824A/en unknown
1988
- 1988-03-03 AU AU12614/88A patent/AU1261488A/en not_active Withdrawn

Also Published As

Publication number	Publication date
FI79851B (fi)	1989-11-30
RO86234B (ro)	1985-03-31
US5250535A (en)	1993-10-05
BR8300475A (pt)	1983-11-01
HU193874B (en)	1987-12-28
EP0085424A2 (en)	1983-08-10
DK29183A (da)	1983-08-02
PT76149A (en)	1983-02-01
FI79851C (fi)	1990-03-12
PL240367A1 (en)	1985-10-08
GR81321B (fi)	1984-12-11
KR840003253A (ko)	1984-08-20
PH19203A (en)	1986-01-31
NZ203128A (en)	1987-08-31
AU572777B2 (en)	1988-05-19
FI830254L (fi)	1983-08-02
IN157856B (fi)	1986-07-12
PL140556B1 (en)	1987-05-30
PH20360A (en)	1986-12-04
PH20099A (en)	1986-09-24
PT76149B (en)	1985-11-25
NO830316L (no)	1983-08-02
NO161372B (no)	1989-05-02
AU1261488A (en)	1988-06-02
KR890000191B1 (ko)	1989-03-10
PH22817A (en)	1989-01-19
EP0085424A3 (en)	1984-07-18
PH22824A (en)	1989-01-19
ES8504194A1 (es)	1985-04-16
AU1096183A (en)	1983-08-11
IL67791A0 (en)	1983-05-15
RO89143A (ro)	1986-04-30
NO161372C (no)	1989-08-09
RO89142A (ro)	1986-04-30
DK29183D0 (da)	1983-01-25
ZW2583A1 (en)	1983-05-11
FI830254A0 (fi)	1983-01-26
ES519423A0 (es)	1985-04-16
RO86234A (ro)	1985-03-15

Publication	Publication Date	Title
DD206781A5 (de)	1984-02-08	Verfahren zur herstellung von purinderivaten
EP0072027B1 (en)	1988-05-18	Antiviral compounds
CA1305140C (en)	1992-07-14	Protected n -9-(1,3-dihydroxy-2-propoxymethyl) guanine derivatives
DE69025723T2 (de)	1996-10-31	N-(Pyrrolo(2-3-d)pyrimidin-3-ylacyl)-Glutaminsäurederivate
DD264924A5 (de)	1989-02-15	Verfahren zur herstellung von pyrimidin-nucleosiden
GB2130204A (en)	1984-05-31	Antiviral purines
DD296927A5 (de)	1991-12-19	Verfahren zur herstellung von 4(3h)-pteridinonen
EP0089028B1 (de)	1988-05-25	Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung
EP0116360B1 (de)	1987-07-01	1-Phenyl-2-aminocarbonylindol-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US4423050A (en)	1983-12-27	9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent
EP0105135B1 (en)	1987-03-18	Substituted 9-(1-0- or 3-0-monosubstituted or 1,3-di-0-substituted 1,3 dihydroxy-2-propoxymethyl) purines as antiviral agents
DE3786109T2 (de)	1993-12-09	Pyrido[2,3-d]pyrimidin-Derivate.
US4612314A (en)	1986-09-16	Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent
US4609661A (en)	1986-09-02	Substituted 9-(1-O- or 3-O-monosubstituted or 1,3-di-O-substituted propoxymethyl)purines as antiviral agents
US4565868A (en)	1986-01-21	Process for preparing guanine derivatives
EP0452680B1 (de)	1996-11-06	Substituierte Purine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als antivirale Mittel
US4603219A (en)	1986-07-29	1,3-dibenzyloxy-2-acetoxymethoxypropane, intermediate for 9-(1,3-dihydroxy-2-propoxymethyl)guanine
DE3785076T2 (de)	1993-07-08	Pyrido(4,3-d)pyrimidin-derivate.
DE69029547T2 (de)	1997-06-26	Purinverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate und Zwischenverbindungen
US4507305A (en)	1985-03-26	9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent
SU1553012A3 (ru)	1990-03-23	Способ получени производных 9-(2-пропоксиметил)гуанина
US5252575A (en)	1993-10-12	Antiviral purine derivatives with improved gastrointestinal absorption
NO874782L (no)	1983-08-02	Guaninderivater.
KR100290533B1 (ko)	2001-05-15	항바이러스 활성을 가지는 2-아미노퓨린
DD221179A5 (de)	1992-05-07	Kombinierter elektromagnetischer und - akustischer wandler fuer fernraeumgeraete

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