HU176907B - Process for preparing 2-amino-9-/ethoxy-methyl-purine derivatives,acid addition and alkali metal salts - Google Patents
Process for preparing 2-amino-9-/ethoxy-methyl-purine derivatives,acid addition and alkali metal salts Download PDFInfo
- Publication number
- HU176907B HU176907B HU77WE550A HUWE000550A HU176907B HU 176907 B HU176907 B HU 176907B HU 77WE550 A HU77WE550 A HU 77WE550A HU WE000550 A HUWE000550 A HU WE000550A HU 176907 B HU176907 B HU 176907B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- guanine
- amino
- preparation
- mixture
- Prior art date
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- -1 alkali metal salts Chemical class 0.000 title claims description 20
- 239000002253 acid Substances 0.000 title claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 51
- 238000002360 preparation method Methods 0.000 claims description 31
- 239000007787 solid Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- JGSACAANCVVBKM-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl propanoate Chemical compound N1=C(N)NC(=O)C2=C1N(COCCOC(=O)CC)C=N2 JGSACAANCVVBKM-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- OFDJYPIEYXKRHP-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl formate Chemical compound O=C1NC(N)=NC2=C1N=CN2COCCOC=O OFDJYPIEYXKRHP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- TYHQCBMIGOIZEH-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethyl formate Chemical compound NC1=NC(N)=C2N=CN(COCCOC=O)C2=N1 TYHQCBMIGOIZEH-UHFFFAOYSA-N 0.000 claims description 5
- XTUQFZILUDKKEU-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl 2,2-dimethylpropanoate Chemical compound N1=C(N)NC(=O)C2=C1N(COCCOC(=O)C(C)(C)C)C=N2 XTUQFZILUDKKEU-UHFFFAOYSA-N 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000003797 solvolysis reaction Methods 0.000 claims description 3
- 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 claims description 2
- 150000005019 2-aminopurines Chemical class 0.000 claims description 2
- ICHLNDWMYWZUTG-UHFFFAOYSA-N 2-azido-7h-purine Chemical class [N-]=[N+]=NC1=NC=C2NC=NC2=N1 ICHLNDWMYWZUTG-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- RRLWYLINGKISHN-UHFFFAOYSA-N ethoxymethanol Chemical class CCOCO RRLWYLINGKISHN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- DSOJUSIKEHUEGN-UHFFFAOYSA-N 9-(ethoxymethyl)purin-2-amine Chemical class N1=C(N)N=C2N(COCC)C=NC2=C1 DSOJUSIKEHUEGN-UHFFFAOYSA-N 0.000 claims 2
- 229960000643 adenine Drugs 0.000 claims 1
- ADIDQIZBYUABQK-UHFFFAOYSA-N alpha-Guaiene Natural products C1C(C(C)=C)CCC(C)C2=C1C(C)CC2 ADIDQIZBYUABQK-UHFFFAOYSA-N 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 20
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 3
- 241000700605 Viruses Species 0.000 abstract description 3
- 230000000840 anti-viral effect Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 150000003212 purines Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000010183 spectrum analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000001110 calcium chloride Substances 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- 238000005550 wet granulation Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- IFLLOYOADZYYGC-UHFFFAOYSA-N 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl 3-chlorobenzoate Chemical compound ClC=1C=C(C(=O)OCCOCN2C=3N=C(NC(C=3N=C2)=O)N)C=CC=1 IFLLOYOADZYYGC-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 description 3
- FFWXHQFJNOGDJE-UHFFFAOYSA-N 2-(4-methylphenoxy)ethanol Chemical compound CC1=CC=C(OCCO)C=C1 FFWXHQFJNOGDJE-UHFFFAOYSA-N 0.000 description 2
- AIUZWPFLGQMINO-UHFFFAOYSA-N 2-(chloromethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCl AIUZWPFLGQMINO-UHFFFAOYSA-N 0.000 description 2
- HVPBQEYFXWIYBP-UHFFFAOYSA-N 2-(chloromethoxy)ethyl propanoate Chemical compound C(CC)(=O)OCCOCCl HVPBQEYFXWIYBP-UHFFFAOYSA-N 0.000 description 2
- CSMCRCLIPQDIKB-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethanol Chemical compound NC1=NC(N)=C2N=CN(COCCO)C2=N1 CSMCRCLIPQDIKB-UHFFFAOYSA-N 0.000 description 2
- VXABKQHGUVWTAN-UHFFFAOYSA-N 2-[(2,6-diaminopurin-9-yl)methoxy]ethyl dodecanoate Chemical compound N1=C(N)N=C2N(COCCOC(=O)CCCCCCCCCCC)C=NC2=C1N VXABKQHGUVWTAN-UHFFFAOYSA-N 0.000 description 2
- BZTJSAXWUKYHCI-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl butanoate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)CCC)C=N2 BZTJSAXWUKYHCI-UHFFFAOYSA-N 0.000 description 2
- SLVUVSMVSSTFHH-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl hexanoate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)CCCCC)C=N2 SLVUVSMVSSTFHH-UHFFFAOYSA-N 0.000 description 2
- JPFMNESGLYNBJP-UHFFFAOYSA-N 2-amino-9-[2-(4-methylphenoxy)ethoxymethyl]-1H-purin-6-one Chemical compound C1(=CC=C(C=C1)OCCOCN1C=2N=C(NC(C=2N=C1)=O)N)C JPFMNESGLYNBJP-UHFFFAOYSA-N 0.000 description 2
- WRUZSOBIWRZLRI-UHFFFAOYSA-N 2-hydroxyethyl 3-chlorobenzoate Chemical compound OCCOC(=O)C1=CC=CC(Cl)=C1 WRUZSOBIWRZLRI-UHFFFAOYSA-N 0.000 description 2
- OTSSKELQKOKVFV-UHFFFAOYSA-N 2-hydroxyethyl naphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCO)=CC=CC2=C1 OTSSKELQKOKVFV-UHFFFAOYSA-N 0.000 description 2
- SFAMKDPMPDEXGH-UHFFFAOYSA-N 2-hydroxyethyl propanoate Chemical compound CCC(=O)OCCO SFAMKDPMPDEXGH-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 2
- 241000450599 DNA viruses Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- KZCPELQCBCVJDJ-UHFFFAOYSA-N 1-[2-(chloromethoxy)ethoxy]-4-methylbenzene Chemical compound CC1=CC=C(OCCOCCl)C=C1 KZCPELQCBCVJDJ-UHFFFAOYSA-N 0.000 description 1
- DOJARZOFEXJALA-UHFFFAOYSA-N 2-(acetyloxymethoxy)ethyl butanoate Chemical compound C(C)(=O)OCOCCOC(CCC)=O DOJARZOFEXJALA-UHFFFAOYSA-N 0.000 description 1
- WDXXXEBDLGCFOL-UHFFFAOYSA-N 2-(chloromethoxy)ethyl 3-chlorobenzoate Chemical compound ClC=1C=C(C(=O)OCCOCCl)C=CC=1 WDXXXEBDLGCFOL-UHFFFAOYSA-N 0.000 description 1
- PTXSLPXLYZHGEM-UHFFFAOYSA-N 2-(chloromethoxy)ethyl formate Chemical compound ClCOCCOC=O PTXSLPXLYZHGEM-UHFFFAOYSA-N 0.000 description 1
- DLBSNYHPCTZFLY-UHFFFAOYSA-N 2-(chloromethoxy)ethyl naphthalene-1-carboxylate Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)OCCOCCl DLBSNYHPCTZFLY-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- IVXUOOVXNYSWEX-UHFFFAOYSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl tridecanoate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)CCCCCCCCCCCC)C=N2 IVXUOOVXNYSWEX-UHFFFAOYSA-N 0.000 description 1
- XDWWJDAXPMJQLC-UHFFFAOYSA-N 2-[(6-amino-2-azidopurin-9-yl)methoxy]ethyl formate Chemical compound N(=[N+]=[N-])C1=NC(=C2N=CN(C2=N1)COCCOC=O)N XDWWJDAXPMJQLC-UHFFFAOYSA-N 0.000 description 1
- QFNIAQMULZQGOW-UHFFFAOYSA-N 2-[bis(trimethylsilyl)amino]-8-trimethylsilyl-3,7-dihydropurin-6-one Chemical compound O=C1NC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=C1NC([Si](C)(C)C)=N2 QFNIAQMULZQGOW-UHFFFAOYSA-N 0.000 description 1
- CTXGTHVAWRBISV-UHFFFAOYSA-N 2-hydroxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCO CTXGTHVAWRBISV-UHFFFAOYSA-N 0.000 description 1
- UKQJDWBNQNAJHB-UHFFFAOYSA-N 2-hydroxyethyl formate Chemical compound OCCOC=O UKQJDWBNQNAJHB-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- UKADKJJNEZZNGH-UHFFFAOYSA-N 7h-purine-2,6-diamine;hydrate Chemical compound O.NC1=NC(N)=C2N=CNC2=N1 UKADKJJNEZZNGH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 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 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700618 Vaccinia virus Species 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 208000011323 eye infectious disease Diseases 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical class 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7988/76A GB1561380A (en) | 1976-03-01 | 1976-03-01 | Esters of hydroxyalkoxyalkyl purines their preparation and pharmaceutical compositions containing them |
| US71810576A | 1976-08-27 | 1976-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176907B true HU176907B (en) | 1981-05-28 |
Family
ID=26241801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77WE550A HU176907B (en) | 1976-03-01 | 1977-03-01 | Process for preparing 2-amino-9-/ethoxy-methyl-purine derivatives,acid addition and alkali metal salts |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS52106896A (en, 2012) |
| AR (4) | AR228232A1 (en, 2012) |
| AT (1) | AT361007B (en, 2012) |
| AU (1) | AU515553B2 (en, 2012) |
| BE (1) | BE851972R (en, 2012) |
| BG (2) | BG27750A3 (en, 2012) |
| CA (1) | CA1086316A (en, 2012) |
| CH (4) | CH629806A5 (en, 2012) |
| DD (1) | DD128611A5 (en, 2012) |
| DE (1) | DE2708827A1 (en, 2012) |
| DK (1) | DK147824C (en, 2012) |
| ES (1) | ES456432A2 (en, 2012) |
| FI (1) | FI60710C (en, 2012) |
| FR (1) | FR2342972A2 (en, 2012) |
| GR (1) | GR66070B (en, 2012) |
| HU (1) | HU176907B (en, 2012) |
| IE (1) | IE44708B1 (en, 2012) |
| IT (1) | IT8048953A0 (en, 2012) |
| LU (1) | LU76869A1 (en, 2012) |
| NL (2) | NL7702175A (en, 2012) |
| PL (2) | PL115242B1 (en, 2012) |
| RO (1) | RO76591A (en, 2012) |
| SE (1) | SE433216B (en, 2012) |
| SU (1) | SU637086A3 (en, 2012) |
| ZA (1) | ZA771220B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8202626A (nl) * | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| ES8403904A1 (es) * | 1983-02-25 | 1984-04-01 | Ind Farma Especial | Un procedimiento para la preparacion de acicloguanosina. |
| GB8816760D0 (en) * | 1988-07-14 | 1988-08-17 | Wellcome Found | Therapeutic compounds |
| US5994361A (en) * | 1994-06-22 | 1999-11-30 | Biochem Pharma | Substituted purinyl derivatives with immunomodulating activity |
| JP4704223B2 (ja) * | 2006-01-30 | 2011-06-15 | Ｈｏｙａ株式会社 | 送りねじ機構 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5122049A (ja) * | 1974-08-19 | 1976-02-21 | Sanwa Denki Kk | Kahenteikosochi |
-
1977
- 1977-02-28 AU AU22759/77A patent/AU515553B2/en not_active Expired
- 1977-03-01 BG BG035556A patent/BG27750A3/xx unknown
- 1977-03-01 CH CH257177A patent/CH629806A5/de not_active IP Right Cessation
- 1977-03-01 DK DK88677A patent/DK147824C/da not_active IP Right Cessation
- 1977-03-01 FR FR7705924A patent/FR2342972A2/fr active Granted
- 1977-03-01 AT AT134877A patent/AT361007B/de not_active IP Right Cessation
- 1977-03-01 NL NL7702175A patent/NL7702175A/xx active Search and Examination
- 1977-03-01 SU SU772455681A patent/SU637086A3/ru active
- 1977-03-01 BG BG036534A patent/BG28067A3/xx unknown
- 1977-03-01 PL PL1977211568A patent/PL115242B1/pl unknown
- 1977-03-01 CA CA272,888A patent/CA1086316A/en not_active Expired
- 1977-03-01 HU HU77WE550A patent/HU176907B/hu not_active IP Right Cessation
- 1977-03-01 IE IE438/77A patent/IE44708B1/en unknown
- 1977-03-01 DE DE19772708827 patent/DE2708827A1/de active Granted
- 1977-03-01 AR AR266728A patent/AR228232A1/es active
- 1977-03-01 DD DD197619A patent/DD128611A5/xx unknown
- 1977-03-01 RO RO7796630A patent/RO76591A/ro unknown
- 1977-03-01 JP JP2211377A patent/JPS52106896A/ja active Granted
- 1977-03-01 FI FI770655A patent/FI60710C/fi not_active IP Right Cessation
- 1977-03-01 SE SE7702233A patent/SE433216B/xx not_active IP Right Cessation
- 1977-03-01 BE BE175383A patent/BE851972R/xx not_active IP Right Cessation
- 1977-03-01 PL PL1977196356A patent/PL115267B1/pl not_active IP Right Cessation
- 1977-03-01 ZA ZA00771220A patent/ZA771220B/xx unknown
- 1977-03-01 LU LU76869A patent/LU76869A1/xx unknown
- 1977-03-01 GR GR52881A patent/GR66070B/el unknown
- 1977-03-01 ES ES456432A patent/ES456432A2/es not_active Expired
-
1980
- 1980-06-12 IT IT8048953A patent/IT8048953A0/it unknown
-
1981
- 1981-07-24 AR AR286219A patent/AR228282A1/es active
- 1981-07-24 AR AR286220A patent/AR228283A1/es active
- 1981-07-24 AR AR286218A patent/AR228281A1/es active
- 1981-08-31 CH CH558581A patent/CH631176A5/de not_active IP Right Cessation
- 1981-08-31 CH CH558681A patent/CH632757A5/de not_active IP Right Cessation
- 1981-08-31 CH CH558781A patent/CH632758A5/de not_active IP Right Cessation
-
1984
- 1984-03-21 NL NL8400896A patent/NL8400896A/nl not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |