CS594082A2 - Method of antiviral effective 2-amino-9-/(2-hydroxy-1-hydroxymethyl-ethoxy)methyl/purines production - Google Patents
Method of antiviral effective 2-amino-9-/(2-hydroxy-1-hydroxymethyl-ethoxy)methyl/purines production Download PDFInfo
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- CS594082A2 CS594082A2 CS825940A CS594082A CS594082A2 CS 594082 A2 CS594082 A2 CS 594082A2 CS 825940 A CS825940 A CS 825940A CS 594082 A CS594082 A CS 594082A CS 594082 A2 CS594082 A2 CS 594082A2
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- Czechoslovakia
- Prior art keywords
- group
- compound
- hydroxy
- formula
- mixture
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 230000000840 anti-viral effect Effects 0.000 title abstract description 10
- -1 2-hydroxy-1-hydroxymethyl-ethoxy Chemical group 0.000 title description 45
- 150000003212 purines Chemical class 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 150000002148 esters Chemical class 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 3
- 238000011282 treatment Methods 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 125000005002 aryl methyl group Chemical group 0.000 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 238000003797 solvolysis reaction Methods 0.000 claims description 3
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 238000007883 cyanide addition reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 84
- 125000003277 amino group Chemical group 0.000 abstract description 6
- 241001529453 unidentified herpesvirus Species 0.000 abstract description 2
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
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- 239000004480 active ingredient Substances 0.000 description 34
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- 239000000243 solution Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 238000009472 formulation Methods 0.000 description 19
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 18
- 229960004150 aciclovir Drugs 0.000 description 18
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
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- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
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- 230000003612 virological effect Effects 0.000 description 9
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
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- 238000003756 stirring Methods 0.000 description 7
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- 238000004809 thin layer chromatography Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
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- 238000001228 spectrum Methods 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 241000283073 Equus caballus Species 0.000 description 5
- 208000000903 Herpes simplex encephalitis Diseases 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 4
- XVXLEAXBSGQNCK-UHFFFAOYSA-N 1,3-bis(phenylmethoxy)propane-2-thiol Chemical compound C=1C=CC=CC=1COCC(S)COCC1=CC=CC=C1 XVXLEAXBSGQNCK-UHFFFAOYSA-N 0.000 description 3
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- 238000001665 trituration Methods 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
-
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8124444 | 1981-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS594082A2 true CS594082A2 (en) | 1989-08-14 |
Family
ID=10523843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS825940A CS594082A2 (en) | 1981-08-11 | 1982-08-10 | Method of antiviral effective 2-amino-9-/(2-hydroxy-1-hydroxymethyl-ethoxy)methyl/purines production |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0072027B1 (no) |
| JP (1) | JPS5841879A (no) |
| KR (1) | KR880002276B1 (no) |
| AT (2) | ATE34393T1 (no) |
| AU (1) | AU569462B2 (no) |
| CA (1) | CA1305138C (no) |
| CS (1) | CS594082A2 (no) |
| DD (1) | DD202717A5 (no) |
| DE (1) | DE3278501D1 (no) |
| DK (1) | DK154561C (no) |
| ES (3) | ES8403128A1 (no) |
| FI (1) | FI76086C (no) |
| GB (1) | GB2104070B (no) |
| GR (1) | GR76891B (no) |
| HU (1) | HU189609B (no) |
| IE (1) | IE54148B1 (no) |
| MC (1) | MC1475A1 (no) |
| NO (1) | NO158539C (no) |
| NZ (1) | NZ201547A (no) |
| PH (3) | PH19940A (no) |
| PL (3) | PL141198B1 (no) |
| PT (1) | PT75406B (no) |
| ZA (1) | ZA825792B (no) |
| ZM (1) | ZM6082A1 (no) |
| ZW (1) | ZW16882A1 (no) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
| US5157120A (en) * | 1980-09-16 | 1992-10-20 | Syntex (U.S.A.) Inc. | Guanine derivatives |
| US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
| NZ201662A (en) * | 1981-08-26 | 1986-07-11 | Merck & Co Inc | 9-(1,3-(and 2,3)-dihydroxy-1-(and 2)-propoxy-methyl)guanine derivatives and methods for their preparation |
| IE830186L (en) * | 1982-02-01 | 1983-08-01 | Syntex Inc | Purines |
| US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
| EP0095813A3 (en) * | 1982-06-01 | 1985-05-08 | THE PROCTER & GAMBLE COMPANY | Penetrating topical pharmaceutical compositions containing 9-(2-hydroxyethoxymethyl) guanine |
| US4556659A (en) * | 1982-08-09 | 1985-12-03 | Syntex (U.S.A.) Inc. | Substituted 9-(1-0- or 3-0-monosubstituted or 1,3-Di-0-substituted propoxymethyl)-purines as antiviral agents |
| US4462986A (en) * | 1982-11-04 | 1984-07-31 | Ens Bio Logicals, Inc. | Synergistic anti-herpes compositions |
| HUT36464A (en) * | 1983-05-24 | 1985-09-30 | Newport Pharmaceuticals | Process for producing erythro-4-amino-3-/2-hydroxy-3-alkyl/-imidazol-5-carboxamide |
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| EP0141927B1 (en) * | 1983-08-18 | 1991-10-30 | Beecham Group Plc | Antiviral guanine derivatives |
| AU577303B2 (en) * | 1983-08-18 | 1988-09-22 | Novartis International Pharmaceutical Ltd | 9-substituted-2-amino purines |
| EP0138683A3 (en) * | 1983-09-30 | 1988-01-20 | Merck & Co. Inc. | Purine derivatives, their application in anti-viral compositions |
| US4897479A (en) * | 1983-09-30 | 1990-01-30 | Merck & Co., Inc. | Arylsulfonyloxy purine intermediates |
| IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| EP0152316B1 (en) * | 1984-01-26 | 1989-07-26 | Merck & Co. Inc. | Substituted butyl guanines and their utilization in antiviral compositions |
| US4621140A (en) * | 1984-02-23 | 1986-11-04 | Syntex (U.S.A.) Inc. | Process for preparing 2,6-substituted-9-(1,3-dihydroxy-2-propoxymethyl)-purines and certain derivatives |
| US4579849A (en) * | 1984-04-06 | 1986-04-01 | Merck & Co., Inc. | N-alkylguanine acyclonucleosides as antiviral agents |
| EP0190123A1 (en) * | 1984-07-20 | 1986-08-13 | GAUNTT, Charles, O. | Immunoregulatory and anti-viral compound |
| IL78643A0 (en) * | 1985-05-02 | 1986-08-31 | Wellcome Found | Purine derivatives,their preparation and pharmaceutical compositions containing them |
| DE3667058D1 (en) | 1985-05-02 | 1989-12-28 | Wellcome Found | Antiviral compounds |
| DE3627024A1 (de) | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
| CA2005815C (en) * | 1988-12-19 | 1999-08-03 | Wellcome Foundation Limited (The) | Antiviral acyclic nucleoside derivatives |
| GB8829571D0 (en) * | 1988-12-19 | 1989-02-08 | Wellcome Found | Antiviral compounds |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| DE4020481A1 (de) * | 1990-06-27 | 1992-01-02 | Hoechst Ag | Verfahren zur herstellung von substituierten acyclischen nukleosiden und dabei auftretende zwischenprodukte |
| US5068119A (en) * | 1990-09-28 | 1991-11-26 | Nabisco Brands, Inc. | Acid-hydrolyzable ester derivatives as low calorie fat mimetics |
| US5567816A (en) * | 1994-07-26 | 1996-10-22 | Syntex (U.S.A.) Inc. | Preparation of acyclovir using 1,3 dioxolane |
| CA2152863A1 (en) * | 1994-07-26 | 1996-01-27 | Yeun-Kwei Han | Preparation of acyclovir |
| US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
| US5840891A (en) * | 1994-07-28 | 1998-11-24 | Syntex (U.S.A.) Inc. | 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol derivative |
| US5565565A (en) * | 1994-08-04 | 1996-10-15 | Syntex (U.S.A.) Inc. | Preparation of N-9 substituted guanine compounds |
| US5559114A (en) * | 1994-12-16 | 1996-09-24 | Exley; Ray W. | Treatment of autoimmune disease using 2-amino purine derivatives |
| US6040446A (en) | 1996-01-26 | 2000-03-21 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol derivative |
| US5840890A (en) * | 1996-01-26 | 1998-11-24 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
| US5700936A (en) * | 1996-01-26 | 1997-12-23 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl) methoxy-1,3-propanediol valinate |
| US5756736A (en) * | 1996-01-26 | 1998-05-26 | Syntex (U.S.A.) Inc. | Process for preparing a 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
| US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
| NZ201662A (en) * | 1981-08-26 | 1986-07-11 | Merck & Co Inc | 9-(1,3-(and 2,3)-dihydroxy-1-(and 2)-propoxy-methyl)guanine derivatives and methods for their preparation |
| US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
-
1982
- 1982-08-10 FI FI822783A patent/FI76086C/fi not_active IP Right Cessation
- 1982-08-10 ZM ZM60/82A patent/ZM6082A1/xx unknown
- 1982-08-10 GR GR69006A patent/GR76891B/el unknown
- 1982-08-10 ZW ZW168/82A patent/ZW16882A1/xx unknown
- 1982-08-10 AU AU87020/82A patent/AU569462B2/en not_active Ceased
- 1982-08-10 PL PL1982237847A patent/PL141198B1/pl unknown
- 1982-08-10 GB GB08222977A patent/GB2104070B/en not_active Expired
- 1982-08-10 DK DK359082A patent/DK154561C/da not_active IP Right Cessation
- 1982-08-10 MC MC821601A patent/MC1475A1/fr unknown
- 1982-08-10 NZ NZ201547A patent/NZ201547A/en unknown
- 1982-08-10 HU HU822577A patent/HU189609B/hu not_active IP Right Cessation
- 1982-08-10 KR KR8203589A patent/KR880002276B1/ko not_active Expired
- 1982-08-10 ES ES514877A patent/ES8403128A1/es not_active Expired
- 1982-08-10 PT PT75406A patent/PT75406B/pt not_active IP Right Cessation
- 1982-08-10 JP JP57139086A patent/JPS5841879A/ja active Granted
- 1982-08-10 PH PH27698A patent/PH19940A/en unknown
- 1982-08-10 ZA ZA825792A patent/ZA825792B/xx unknown
- 1982-08-10 IE IE1921/82A patent/IE54148B1/en not_active IP Right Cessation
- 1982-08-10 AT AT82107247T patent/ATE34393T1/de active
- 1982-08-10 PL PL1982247393A patent/PL141281B1/pl unknown
- 1982-08-10 PL PL24739482A patent/PL247394A1/xx unknown
- 1982-08-10 NO NO822725A patent/NO158539C/no unknown
- 1982-08-10 EP EP82107247A patent/EP0072027B1/en not_active Expired
- 1982-08-10 DE DE8282107247T patent/DE3278501D1/de not_active Expired
- 1982-08-10 CA CA000409132A patent/CA1305138C/en not_active Expired - Fee Related
- 1982-08-10 AT AT0306082A patent/AT380252B/de not_active IP Right Cessation
- 1982-08-10 CS CS825940A patent/CS594082A2/cs unknown
- 1982-08-10 DD DD82242394A patent/DD202717A5/de unknown
-
1983
- 1983-04-15 ES ES521550A patent/ES8504802A1/es not_active Expired
- 1983-04-15 ES ES521551A patent/ES521551A0/es active Granted
- 1983-12-16 PH PH29987A patent/PH20148A/en unknown
- 1983-12-16 PH PH29988A patent/PH18814A/en unknown
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