JPH01501478A - ９―置換グアニン - Google Patents
９―置換グアニンInfo
- Publication number
- JPH01501478A JPH01501478A JP88500627A JP50062788A JPH01501478A JP H01501478 A JPH01501478 A JP H01501478A JP 88500627 A JP88500627 A JP 88500627A JP 50062788 A JP50062788 A JP 50062788A JP H01501478 A JPH01501478 A JP H01501478A
- Authority
- JP
- Japan
- Prior art keywords
- acetylguanine
- acyclovir
- tetrahydrofuryloxy
- temperature
- ethoxymethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims description 14
- -1 2-tetrahydropyranyl Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 29
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 19
- 229960004150 aciclovir Drugs 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 6
- MXSMRDDXWJSGMC-UHFFFAOYSA-N n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N=CN2 MXSMRDDXWJSGMC-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 235000019441 ethanol Nutrition 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
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000009889 Herpes Simplex Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 208000000903 Herpes simplex encephalitis Diseases 0.000 description 2
- 241000700584 Simplexvirus Species 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000000609 ganglia Anatomy 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 230000001953 sensory effect Effects 0.000 description 2
- 241000271566 Aves Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000007835 Cyamopsis tetragonoloba Species 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 208000037018 Herpes simplex virus encephalitis Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- DATAGRPVKZEWHA-YFKPBYRVSA-N L-Theanine Natural products CCNC(=O)CC[C@H]([NH3+])C([O-])=O DATAGRPVKZEWHA-YFKPBYRVSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000111306 Torreya nucifera Species 0.000 description 1
- 235000006732 Torreya nucifera Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000002642 intravenous therapy Methods 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- DJMINGJGFGSDDB-UHFFFAOYSA-N n-[9-(2-hydroxyethoxymethyl)-6-oxo-3h-purin-2-yl]acetamide Chemical compound N1C(NC(=O)C)=NC(=O)C2=C1N(COCCO)C=N2 DJMINGJGFGSDDB-UHFFFAOYSA-N 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 230000003589 nefrotoxic effect Effects 0.000 description 1
- 231100000381 nephrotoxic Toxicity 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940026510 theanine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000009385 viral infection Effects 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU4152348/23 | 1986-11-25 | ||
| SU4152348 | 1986-11-25 | ||
| PCT/SU1987/000135 WO1988003923A1 (fr) | 1986-11-25 | 1987-11-23 | Guanines substitutees en position 9 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01501478A true JPH01501478A (ja) | 1989-05-25 |
| JPH0587073B2 JPH0587073B2 (enExample) | 1993-12-15 |
Family
ID=21269444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP88500627A Granted JPH01501478A (ja) | 1986-11-25 | 1987-11-23 | ９―置換グアニン |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4916225A (enExample) |
| EP (1) | EP0290630A4 (enExample) |
| JP (1) | JPH01501478A (enExample) |
| WO (1) | WO1988003923A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010528045A (ja) * | 2007-05-25 | 2010-08-19 | バーロウ ファーマシューティカルズ，インコーポレイティド | 腎毒性を低めるために有用な組成物及びその使用方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995003572A1 (en) * | 1993-07-23 | 1995-02-02 | Apple Computer, Inc. | Method and apparatus for fuzzy logic rule execution |
| DE19541264A1 (de) * | 1995-11-06 | 1997-05-07 | Bayer Ag | Purin-6-on-derivate |
| CN102250126A (zh) * | 2010-05-18 | 2011-11-23 | 北京化工大学 | 一种双嘌呤类衍生物及其合成 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228937A (en) * | 1963-07-17 | 1966-01-11 | Shell Oil Co | Adenine derivative |
| US3903169A (en) * | 1973-08-27 | 1975-09-02 | Polaroid Corp | Process of reacting cyclopentanone with lactones |
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| US4199574A (en) * | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| US4241063A (en) * | 1979-08-06 | 1980-12-23 | Bristol-Myers Company | Purine derivatives and their use as bronchodilators |
| EP0052964A1 (en) * | 1980-11-20 | 1982-06-02 | Beecham Group Plc | Adenine derivatives possessing pharmacological activity |
| US4507305A (en) * | 1981-05-21 | 1985-03-26 | Syntex (U.S.A.) Inc. | 9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent |
| SE8203856D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine ii |
| SE8203855D0 (sv) * | 1982-06-21 | 1982-06-21 | Astra Laekemedel Ab | Novel derivatives of guanine i |
| US4612314A (en) * | 1982-12-22 | 1986-09-16 | Syntex (U.S.A.) Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
| US4826981A (en) * | 1984-12-22 | 1989-05-02 | Krka | Process for preparing 9-(2-hydroxyethoxymethyl)-guanine |
| YU45690B (sh) * | 1984-12-22 | 1992-07-20 | Krka Tovarna Zdraviln.Sol.O. | Postopek za pripravo 9-(2-hidroksietoksimetil)-gvanina |
| JPH0633263B2 (ja) * | 1985-05-27 | 1994-05-02 | 鐘淵化学工業株式会社 | ７−ヒドロキシグアニン誘導体及びその製造方法並びにそれを有効成分とする抗腫瘍剤 |
-
1987
- 1987-11-23 JP JP88500627A patent/JPH01501478A/ja active Granted
- 1987-11-23 US US07/242,191 patent/US4916225A/en not_active Expired - Fee Related
- 1987-11-23 EP EP19880900265 patent/EP0290630A4/de not_active Withdrawn
- 1987-11-23 WO PCT/SU1987/000135 patent/WO1988003923A1/ru not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010528045A (ja) * | 2007-05-25 | 2010-08-19 | バーロウ ファーマシューティカルズ，インコーポレイティド | 腎毒性を低めるために有用な組成物及びその使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0290630A4 (de) | 1990-02-26 |
| EP0290630A1 (de) | 1988-11-17 |
| US4916225A (en) | 1990-04-10 |
| JPH0587073B2 (enExample) | 1993-12-15 |
| WO1988003923A1 (fr) | 1988-06-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU799664A3 (ru) | Способ получени 9-(2-оксиэтоксиметил)гуАНиНА или ЕгО СОлЕй | |
| JPH08501071A (ja) | １，５−アンヒドロヘキシトールヌクレオシド類似体および該類似体の医薬としての使用 | |
| HU189709B (en) | Process for preparing ester derivatives of 9-/2-hydroxy-ethoxy-methyl/-guanine | |
| BR112014003420B1 (pt) | Hemifumarato de tenofovir alafenamida. composição, seus métodos de preparação e uso | |
| JPH031309B2 (enExample) | ||
| US3666856A (en) | Treating immune response with amino purine derivatives | |
| US3991190A (en) | Treatment of viral infections | |
| AU2013249708A1 (en) | Cyclopropanecarboxylate esters of purine analogues | |
| JPH01501478A (ja) | ９―置換グアニン | |
| GB2174391A (en) | 5-pyrimidinecarboxamides and treatment of leukemia and tumours therewith | |
| JPH0240369A (ja) | 新規なネプラノシン誘導体類 | |
| JPS59186985A (ja) | ジメチルアミノメチレン化された抗ヘルペス化合物 | |
| JPH013197A (ja) | 抗ウイルス化合物およびそれを含有する抗ウイルス剤 | |
| JPH05507719A (ja) | 薬学的治療 | |
| Diana et al. | Chemotherapy of virus diseases | |
| JPS6363547B2 (enExample) | ||
| US3796798A (en) | 3-(1-piperazinyliminomethyl)rifamycin sv antiviral methods | |
| AU2023404746A1 (en) | Compound and use thereof in treatment of treg-related diseases | |
| RU2533232C2 (ru) | Применение поликарбоксильного производного фуллерена в качестве микробицидного противовирусного средства | |
| CN112661801B (zh) | 一种核苷类似物及其氘代物及其制备方法和用途 | |
| JPS61502891A (ja) | 新規の免疫に有効な化合物 | |
| JPS6041670B2 (ja) | ２，６−ジメチル−１，４−ジヒドロピリジン−３，５−ジカルボン酸エステルおよびその製造方法 | |
| RU2441016C1 (ru) | Соли 5'-аминокарбонилфосфоната 3'-азидо-3'-дезокситимидина, являющиеся селективными ингибиторами продукции вируса иммунодефицита человека вич-1 | |
| SU1678206A3 (ru) | Способ получени 1, 3, 4-тиадиазол-2-цианамида или его фармацевтически приемлемых солей | |
| DE69406293T2 (de) | Benzothiophen analoga als antivirale mittel |