FI111370B - Förfarande för framställning av virusmotverkande monoesterföreningar - Google Patents
Förfarande för framställning av virusmotverkande monoesterföreningar Download PDFInfo
- Publication number
- FI111370B FI111370B FI954727A FI954727A FI111370B FI 111370 B FI111370 B FI 111370B FI 954727 A FI954727 A FI 954727A FI 954727 A FI954727 A FI 954727A FI 111370 B FI111370 B FI 111370B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- ribofuranose
- acid
- hydroxymethyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/056—Triazole or tetrazole radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Claims (6)
1. Förfarande för framställning av nya virusmotver-kande monoesterföreningar med formeln 5 Nu-O-Fa (I) där O är syre, Nu är en nukleosidanalog, Fa är en acylgrupp i en mono-omättad Ci8- eller C2o-w-9-fettsyra, som är es-10 terifierad med en hydroxylgrupp, som föreligger i 5'-ställning i nuklosidanalogens sockerdel, eller med en terminal hydroxylgrupp pä den icke-cykliska gruppen i nuklosi-danalogen, och där Nu har formeln II:
15 B-S (II) där S antingen är ett monosackaridderivat, som valts bland följande: Ι-β-D-ribofuranos, Ι-β-D-arabinofuranos, 2-deoxi-Ι-β-D-ribofuranos, 2,3-dideoxi-l-B-D-ribofuranos, 2,3-dide-20 hydro-2,3-dideoxi-l-fi-D-ribofuranos, 2-deoxi-2-fluor-l-B-D-arabinofuranos, 2,3-dideoxi-3-azido-l-B-D-ribofuranos eller 4-hydroximetyl-2-cyklopenten-l-yl, eller som valts ur gruppen bestäende av följande: 2-hydroxietoximetyl, 4-hydroxi- 3-(hydroximetyl)butyl, 2-hydroxi-l-(hydroximetyl)etoxi- 25 metyl, 2,3-dihydroxipropoxi eller 2,3-dihydroxipropyl; och B är ett heterocykliskt ringsystem som valts bland följande formler: (i)
30. X x NV nva i I T 111370 där X = O, S, NH och Ri = NH2, CH3, CH30 och A = NH, S, Se, CH2, O, , eller (ii) o x ' H--vr HiN V- Λ» Λ» 10 //° H2N"\ H2N-X
15 JT\ Y'^XN/N NX/N där X = NH, S, O och Y = H, OH, F, Cl, Br, I, NH2, CH2CN, 20 C=CH, eller (iii) H OH
25 HN | % eller 30 (iv) o 35. jj j I o Nr I 1 111370 där R4 = H, NH2, NHOH, NHCOCH3, NHCH3, NHNH2 och R5 = H, F, Cl, Br, I, CH3, CF3 och R6 = CH3, F, I, C=CHBr, CH2OH, CH2NH2, C=CCH3, eller (v) 5 *2 /N fXy där R2 = OH, SH, H, Cl och R3 = H, OH, Cl, SH, NH2; föruts-15 tatt att när S är Ι-β-D-arabinofuranos, 2,3-dideoxi-3- azido-l-F-D-ribofuranos, 2-hydroxietoximetyl, 4-hydroxi-3-(hydroximetyl)butyl, 2-hydroxi-l-(hydroxiraetyl)etoximetyl eller 2,3-dihydroxipropoxi, sä kan B inte vara: (a) (b)
20. O J JL ,
25 O^-N (c) eller (d)
30 OH NH2 11 > 1 ) «,ΑΙ-» °*γ 111370 och förutsatt att föreningen enligt formel (I) inte är 5'-oktadekenoyl-5-fluoruridin, kännetecknat av att en förening med formeln
5 B-S-OH där B och S har ovannämnda betyldelse, bringas att reagera med en förening med formeln
10 Fa X där Fa är en acylgrupp i en mono-omättad Cig- eller C20-g>-9-fettsyra, och X är Cl, Br, O-CO-R', varvid R' är Fa, CH3, CH2CH3 eller 15 CF3; eller bensotriazoldelen i fettsyrabensotriazol.
2. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening med formeln (I) där B-S är ribavirin, selenazol, pyrazomycin, 2'-deoxicoformycin. 20
3. Förfarande enligt patentkrav 1 eller 2, kän netecknat av att man framställer en förening med formeln (I) där Fa är oleinsyra, elaidinsyra eller eicosen-syra, cis eller trans.
4. Förfarande enligt patentkrav 1, k ä n n e -25 tecknat av att man framställer en förening med formeln (I) där B-S är ribavirin och Fa är oleinsyra.
5. Förfarande enligt patentkrav 1, kännetecknat av att man framställer en förening med formeln (I) där B-S är ribavirin och Fa är elaidinsyra. 30
6. Förfarande enligt patentkrav 1, k ä n n e - tecknat av att man framställer en förening med formeln (I) där B-S är ribavirin och Fa är eicosensyra, cis eller trans.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939307043A GB9307043D0 (en) | 1993-04-05 | 1993-04-05 | Chemical compounds |
| GB9307043 | 1993-05-04 | ||
| NO9400071 | 1994-04-05 | ||
| PCT/NO1994/000071 WO1994022887A1 (en) | 1993-04-05 | 1994-04-05 | New antiviral compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI954727A0 FI954727A0 (sv) | 1995-10-04 |
| FI954727A FI954727A (sv) | 1995-10-04 |
| FI111370B true FI111370B (sv) | 2003-07-15 |
Family
ID=10733340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI954727A FI111370B (sv) | 1993-04-05 | 1995-10-04 | Förfarande för framställning av virusmotverkande monoesterföreningar |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6153594A (sv) |
| EP (1) | EP0693077B1 (sv) |
| JP (1) | JP3049258B2 (sv) |
| KR (1) | KR100309194B1 (sv) |
| AT (1) | ATE171457T1 (sv) |
| AU (1) | AU685104B2 (sv) |
| CA (1) | CA2158853C (sv) |
| CZ (1) | CZ287755B6 (sv) |
| DE (1) | DE69413529T2 (sv) |
| DK (1) | DK0693077T3 (sv) |
| ES (1) | ES2124883T3 (sv) |
| FI (1) | FI111370B (sv) |
| GB (1) | GB9307043D0 (sv) |
| HK (1) | HK1003437A1 (sv) |
| HU (1) | HU228064B1 (sv) |
| NZ (1) | NZ263888A (sv) |
| PL (1) | PL177263B1 (sv) |
| RU (1) | RU2139884C1 (sv) |
| SK (1) | SK281231B6 (sv) |
| UA (1) | UA41361C2 (sv) |
| WO (1) | WO1994022887A1 (sv) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9515279D0 (en) | 1995-07-25 | 1995-09-20 | Norsk Hydro As | Improved therapeutic agents |
| US6703394B2 (en) | 1996-02-16 | 2004-03-09 | Medivir Ab | Acyclic nucleoside derivatives |
| US5869493A (en) | 1996-02-16 | 1999-02-09 | Medivir Ab | Acyclic nucleoside derivatives |
| WO1998032762A1 (en) * | 1997-01-24 | 1998-07-30 | Norsk Hydro Asa | Gemcitabine derivatives |
| US5891881A (en) * | 1997-11-21 | 1999-04-06 | Clarion Pharmaceuticals Inc. | Aminoheterocycle-substituted glycerols |
| EP1042341A1 (en) * | 1997-11-25 | 2000-10-11 | Protarga Inc. | Nucleoside analog compositions and uses thereof |
| KR100622889B1 (ko) | 1998-07-09 | 2006-09-12 | 상꾜 가부시키가이샤 | 신규 항세균 화합물 |
| US6277830B1 (en) | 1998-10-16 | 2001-08-21 | Schering Corporation | 5′-amino acid esters of ribavirin and the use of same to treat hepatitis C with interferon |
| US6403564B1 (en) | 1998-10-16 | 2002-06-11 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable HCV-RNA in patients having chronic hepatitis C infection |
| AU762395B2 (en) * | 1998-10-16 | 2003-06-26 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable HCV-RNA in patients having chronic hepatitis C infection |
| TWI245047B (en) | 1999-08-20 | 2005-12-11 | Sankyo Co | Novel A-500359 derivatives |
| US7638496B2 (en) | 2000-02-15 | 2009-12-29 | Valeant Pharmaceuticals North America | Nucleoside analogs with carboxamidine modified monocyclic base |
| EP1282632A1 (en) | 2000-04-20 | 2003-02-12 | Schering Corporation | Ribavirin-interferon alfa combination therapy for eradicating detectable hcv-rna in patients having chronic hepatitis c infection |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| AP1727A (en) * | 2000-05-26 | 2007-03-06 | Idenix Cayman Ltd | Methods and compositions for treating flaviviruses and pestiviruses. |
| US20030229082A1 (en) * | 2002-01-16 | 2003-12-11 | The Regents Of The University Of California | Inhibition of RNA function |
| EP1536804A4 (en) | 2002-06-28 | 2007-10-31 | Idenix Cayman Ltd | 2'-C-METHYL-3'-O-L-VALINESTER-RIBOFURANOSYLCYTIDINE FOR THE TREATMENT OF FLAVIVIRIDAE INFECTIONS |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US20040077607A1 (en) * | 2002-10-21 | 2004-04-22 | Uckun Fatih M. | Aryl phosphate derivatives of d4T with potent anti-viral activity against hemorrhagic fever viruses |
| JP2006504438A (ja) * | 2002-11-01 | 2006-02-09 | エヴォジェニクス・ピーティーワイ・リミテッド | リバビリンおよび／またはｒｎａレプリカーゼを使用した変異誘発方法 |
| HUE033832T2 (en) | 2002-11-15 | 2018-01-29 | Idenix Pharmaceuticals Llc | 2'-methyl nucleosides in combination with interferon and Flaviviridae mutation |
| TWI332507B (en) | 2002-11-19 | 2010-11-01 | Hoffmann La Roche | Antiviral nucleoside derivatives |
| JP5116972B2 (ja) | 2002-12-12 | 2013-01-09 | イデニクス（ケイマン）リミテツド | ２’−分枝ヌクレオシドの製造方法 |
| WO2004084453A2 (en) * | 2003-03-20 | 2004-09-30 | Microbiologica Quimica E Farmaceutica Ltd. | METHODS OF MANUFACTURE OF 2'-DEOXY-β-L-NUCLEOSIDES |
| WO2005049633A1 (en) * | 2003-11-03 | 2005-06-02 | Cognis Ip Management Gmbh | Acyl ribonucleosides and acyl deoxyribonucleosides |
| FR2874016B1 (fr) | 2004-06-30 | 2006-11-24 | Centre Nat Rech Scient Cnrse | Nanoparticules de derives de la gemcitabine |
| US8114847B2 (en) | 2005-03-16 | 2012-02-14 | Case Western Reserve University | Selective inhibitors of translesion DNA replication |
| WO2008147454A1 (en) * | 2006-11-16 | 2008-12-04 | Case Western Reserve University | Selective inhibitors of translesion dna replication |
| NO324263B1 (no) * | 2005-12-08 | 2007-09-17 | Clavis Pharma Asa | Kjemiske forbindelser, anvendelse derav ved behandling av kreft, samt farmasoytiske preparater som omfatter slike forbindelser |
| WO2007075876A2 (en) | 2005-12-23 | 2007-07-05 | Idenix Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| US8497292B2 (en) * | 2005-12-28 | 2013-07-30 | Translational Therapeutics, Inc. | Translational dysfunction based therapeutics |
| RU2488591C2 (ru) * | 2007-09-26 | 2013-07-27 | Маунт Синай Скул Оф Медсин | Аналоги азацитидина и их применение |
| WO2013033705A2 (en) | 2011-09-01 | 2013-03-07 | Case Western Reserve University | Non-natural nucleosides as theranostic agents |
| US9821173B2 (en) | 2013-02-08 | 2017-11-21 | Case Western Reserve University | Anti-cancer agents and methods of use |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920630A (en) * | 1970-09-24 | 1975-11-18 | Upjohn Co | 2,2{40 -Anhydro-ara-cytidine compounds and process of preparation |
| GB1325797A (en) * | 1970-09-24 | 1973-08-08 | Upjohn Co | Medicines comprising cytidine derivatives |
| US3984396A (en) * | 1971-06-01 | 1976-10-05 | Icn Pharmaceuticals, Inc. | 1-(β,-D-ribofuranosyl)-1,2,4-triazole acid esters |
| US3998807A (en) * | 1972-03-03 | 1976-12-21 | Syntex (U.S.A.) Inc. | Arabinofuranosyl cytosines and methods of making |
| GB1482736A (en) * | 1974-03-18 | 1977-08-10 | Icn Pharmaceuticals | 1-(beta-d-ribofuranosyl)-1,2,4-triazole acid derivatives |
| US3960836A (en) * | 1974-07-22 | 1976-06-01 | Eli Lilly And Company | Acylated derivatives of pyrazofurin and process for their preparation |
| JPS5159880A (en) * | 1974-11-22 | 1976-05-25 | Asahi Chemical Ind | N44 ashirunukureoshidojikarubonsanesuteruno seiho |
| DE3100478A1 (de) * | 1981-01-09 | 1982-08-12 | Dr. Thilo & Co GmbH, 8021 Sauerlach | 5'ester von pyrimidinnucleosiden mit antiviraler wirksamkeit, verfahren zur herstellung und daraus hergestellte arzneimittel |
| US4531001A (en) * | 1982-03-23 | 1985-07-23 | Brigham Young University | 2-β-D-ribofuranosylselenazole-4-carboxamide compounds |
| US4684631A (en) * | 1984-10-09 | 1987-08-04 | Toyama Chemical Co., Ltd. | Novel 5-fluoro-2-deoxyuridine derivatives and salts thereof, process for producing the same, and antitumor agents containing the same |
| JPH0655755B2 (ja) * | 1985-01-23 | 1994-07-27 | 富山化学工業株式会社 | 新規な５−フルオロ−２′−デオキシウリジン−３′−ホスフエ−ト誘導体およびその塩 |
| US5223263A (en) * | 1988-07-07 | 1993-06-29 | Vical, Inc. | Liponucleotide-containing liposomes |
| JPS6483092A (en) * | 1987-09-24 | 1989-03-28 | Arakawa Chotaro & Co | Novel n6,n6-dimethyladenosine derivative having carcinostatic activity, its production and carcinostatic agent containing said derivative as active component |
| JPH0278696A (ja) * | 1988-09-13 | 1990-03-19 | Shoichiro Ozaki | ５−フルオロウラシル誘導体 |
| US5216142A (en) * | 1989-04-17 | 1993-06-01 | Efamol Holdings Plc | Anti-virals |
| GB2260319B (en) * | 1991-10-07 | 1995-12-06 | Norsk Hydro As | Acyl derivatives of nucleosides and nucleoside analogues having anti-viral activity |
| US5405837A (en) * | 1993-05-18 | 1995-04-11 | Indiana University Foundation | Method for the treatment of neoplastic disease utilizing tiazofurin and ribavirin |
-
1993
- 1993-04-05 GB GB939307043A patent/GB9307043D0/en active Pending
-
1994
- 1994-04-05 JP JP6521952A patent/JP3049258B2/ja not_active Expired - Lifetime
- 1994-04-05 AU AU65141/94A patent/AU685104B2/en not_active Expired
- 1994-04-05 DE DE69413529T patent/DE69413529T2/de not_active Expired - Lifetime
- 1994-04-05 RU RU95119386A patent/RU2139884C1/ru active
- 1994-04-05 WO PCT/NO1994/000071 patent/WO1994022887A1/en active IP Right Grant
- 1994-04-05 UA UA95104367A patent/UA41361C2/uk unknown
- 1994-04-05 US US08/532,754 patent/US6153594A/en not_active Expired - Lifetime
- 1994-04-05 AT AT94912709T patent/ATE171457T1/de active
- 1994-04-05 SK SK1233-95A patent/SK281231B6/sk not_active IP Right Cessation
- 1994-04-05 DK DK94912709T patent/DK0693077T3/da active
- 1994-04-05 NZ NZ263888A patent/NZ263888A/en not_active IP Right Cessation
- 1994-04-05 KR KR1019950704292A patent/KR100309194B1/ko not_active IP Right Cessation
- 1994-04-05 CA CA002158853A patent/CA2158853C/en not_active Expired - Lifetime
- 1994-04-05 ES ES94912709T patent/ES2124883T3/es not_active Expired - Lifetime
- 1994-04-05 CZ CZ19952593A patent/CZ287755B6/cs not_active IP Right Cessation
- 1994-04-05 EP EP94912709A patent/EP0693077B1/en not_active Expired - Lifetime
- 1994-04-05 HU HU9502896A patent/HU228064B1/hu unknown
- 1994-04-05 PL PL94310970A patent/PL177263B1/pl unknown
-
1995
- 1995-10-04 FI FI954727A patent/FI111370B/sv not_active IP Right Cessation
-
1998
- 1998-03-24 HK HK98102521A patent/HK1003437A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994022887A1 (en) | 1994-10-13 |
| FI954727A0 (sv) | 1995-10-04 |
| EP0693077A1 (en) | 1996-01-24 |
| JPH08508477A (ja) | 1996-09-10 |
| CZ287755B6 (en) | 2001-01-17 |
| JP3049258B2 (ja) | 2000-06-05 |
| NZ263888A (en) | 1998-05-27 |
| DE69413529T2 (de) | 1999-04-29 |
| AU6514194A (en) | 1994-10-24 |
| GB9307043D0 (en) | 1993-05-26 |
| HUT73659A (en) | 1996-09-30 |
| CZ259395A3 (en) | 1996-06-12 |
| FI954727A (sv) | 1995-10-04 |
| DK0693077T3 (da) | 1999-06-14 |
| KR100309194B1 (ko) | 2002-06-20 |
| PL310970A1 (en) | 1996-01-22 |
| PL177263B1 (pl) | 1999-10-29 |
| SK123395A3 (en) | 1996-04-03 |
| HU228064B1 (en) | 2012-09-28 |
| CA2158853A1 (en) | 1994-10-13 |
| SK281231B6 (sk) | 2001-01-18 |
| ATE171457T1 (de) | 1998-10-15 |
| UA41361C2 (uk) | 2001-09-17 |
| HU9502896D0 (en) | 1995-11-28 |
| EP0693077B1 (en) | 1998-09-23 |
| US6153594A (en) | 2000-11-28 |
| AU685104B2 (en) | 1998-01-15 |
| CA2158853C (en) | 1999-07-27 |
| DE69413529D1 (de) | 1998-10-29 |
| HK1003437A1 (en) | 1998-10-30 |
| ES2124883T3 (es) | 1999-02-16 |
| RU2139884C1 (ru) | 1999-10-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI111370B (sv) | Förfarande för framställning av virusmotverkande monoesterföreningar | |
| EP2615101B1 (en) | Nucleoside derivatives, synthesis methods and uses thereof for preparing anti-tumor and anti-virus medicaments | |
| US20130018013A1 (en) | Bicyclic nucleosides and nucleotides as therapeutic agents | |
| JP2008532950A (ja) | 治療薬としての二環式ヌクレオシドおよび二環式ヌクレオチド | |
| KR100272732B1 (ko) | 항바이러스성을 나타내는 누클레오시드 및 누클레오시드 유사체의 아실 유도체 및 이 화합물을 함유하는 약학 조성물 | |
| AU732120B2 (en) | Pyrimidine nucleotide precursors for treatment of systemic inflammation and inflammatory hepatitis | |
| AU672369C (en) | Chemical compounds | |
| IE930047A1 (en) | Chemical compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |