CA2465928C - Synthesis and purification of valacyclovir - Google Patents
Synthesis and purification of valacyclovir Download PDFInfo
- Publication number
- CA2465928C CA2465928C CA002465928A CA2465928A CA2465928C CA 2465928 C CA2465928 C CA 2465928C CA 002465928 A CA002465928 A CA 002465928A CA 2465928 A CA2465928 A CA 2465928A CA 2465928 C CA2465928 C CA 2465928C
- Authority
- CA
- Canada
- Prior art keywords
- valacyclovir
- valine
- protected
- pure
- deprotecting
- 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.)
- Expired - Fee Related
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- HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 title claims abstract description 68
- 229940093257 valacyclovir Drugs 0.000 title claims abstract description 66
- 230000015572 biosynthetic process Effects 0.000 title description 3
- 238000000746 purification Methods 0.000 title description 3
- 238000003786 synthesis reaction Methods 0.000 title description 3
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229960004150 aciclovir Drugs 0.000 claims abstract description 40
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- 238000005859 coupling reaction Methods 0.000 claims abstract description 30
- FGLBYLSLCQBNHV-NSHDSACASA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)C)C=N2 FGLBYLSLCQBNHV-NSHDSACASA-N 0.000 claims abstract description 29
- 230000008878 coupling Effects 0.000 claims abstract description 28
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- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- FETSQPAGYOVAQU-UHFFFAOYSA-N glyceryl palmitostearate Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O FETSQPAGYOVAQU-UHFFFAOYSA-N 0.000 description 1
- 229940046813 glyceryl palmitostearate Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000010224 hepatic metabolism Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 230000010226 intestinal metabolism Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960000540 polacrilin potassium Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- WVWZXTJUCNEUAE-UHFFFAOYSA-M potassium;1,2-bis(ethenyl)benzene;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O.C=CC1=CC=CC=C1C=C WVWZXTJUCNEUAE-UHFFFAOYSA-M 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical compound O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940108442 valtrex Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- 229940107931 zovirax Drugs 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
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002649826A CA2649826A1 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33280201P | 2001-11-14 | 2001-11-14 | |
| US60/332,802 | 2001-11-14 | ||
| US34227301P | 2001-12-21 | 2001-12-21 | |
| US60/342,273 | 2001-12-21 | ||
| PCT/US2002/036269 WO2003041647A2 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002649826A Division CA2649826A1 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2465928A1 CA2465928A1 (en) | 2003-05-22 |
| CA2465928C true CA2465928C (en) | 2010-01-19 |
Family
ID=26988392
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002465928A Expired - Fee Related CA2465928C (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
| CA002649826A Abandoned CA2649826A1 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002649826A Abandoned CA2649826A1 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6849737B2 (en:Method) |
| EP (1) | EP1465894A4 (en:Method) |
| JP (1) | JP2005508993A (en:Method) |
| KR (2) | KR20050044449A (en:Method) |
| CN (1) | CN1307177C (en:Method) |
| CA (2) | CA2465928C (en:Method) |
| HR (1) | HRP20040511A2 (en:Method) |
| IL (1) | IL161969A0 (en:Method) |
| IN (1) | IN2007DE04250A (en:Method) |
| IS (1) | IS7260A (en:Method) |
| MX (1) | MX242714B (en:Method) |
| NO (1) | NO20042433L (en:Method) |
| PL (1) | PL371732A1 (en:Method) |
| WO (1) | WO2003041647A2 (en:Method) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04002192A (es) * | 2001-09-07 | 2005-02-17 | Teva Pharma | Formas cristalinas de clorhidrato de valaciclovir. |
| US20040197396A1 (en) * | 2001-11-05 | 2004-10-07 | Fain Helen S | Anhydrous crystal form of valaciclovir hydrochloride |
| MX242714B (es) * | 2001-11-14 | 2006-12-15 | Teva Pharma | Sintesis y purificacion de valaciclovir. |
| US20050043329A1 (en) * | 2002-09-06 | 2005-02-24 | Shlomit Wizel | Crystalline forms of valacyclovir hydrochloride |
| US20050059684A1 (en) * | 2002-10-16 | 2005-03-17 | Ben-Zion Dolitzky | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| EP1551838B1 (en) * | 2002-10-16 | 2006-08-09 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| AU2003289995A1 (en) * | 2002-12-09 | 2004-06-30 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| WO2004106338A1 (en) * | 2003-05-30 | 2004-12-09 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| EP2014660A3 (en) * | 2003-06-02 | 2009-07-15 | Teva Pharmaceutical Industries Ltd | Novel crystalline forms of valacyclovir hydrochloride |
| EP1706406A1 (en) * | 2004-01-21 | 2006-10-04 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of valacyclovir hydrochloride |
| CA2572268A1 (en) * | 2004-06-30 | 2006-02-02 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| CN101068814A (zh) * | 2004-09-04 | 2007-11-07 | 特瓦制药工业有限公司 | 分离的伐昔洛韦杂质，制备伐昔洛韦杂质的方法及其作为参比标准物的应用 |
| US7958087B2 (en) * | 2004-11-17 | 2011-06-07 | Iron Mountain Incorporated | Systems and methods for cross-system digital asset tag propagation |
| EP1746098A1 (en) * | 2005-07-21 | 2007-01-24 | SOLMAG S.p.A. | Valacyclovir polymorphs and a process for the preparation thereof |
| US20070112193A1 (en) * | 2005-11-14 | 2007-05-17 | Khunt Mayur D | Valacyclovir process |
| GB0605344D0 (en) * | 2006-03-17 | 2006-04-26 | Pliva Istrazivanje I Razvoj D | Pharmaceutically acceptable salts and polymorphic forms |
| CN1903854B (zh) * | 2006-08-09 | 2012-05-23 | 丽珠医药集团股份有限公司 | 一种合成盐酸伐昔洛韦的方法 |
| JP5152180B2 (ja) * | 2007-04-27 | 2013-02-27 | 味の素株式会社 | バラシクロビルの製造方法 |
| US20080281099A1 (en) * | 2007-05-07 | 2008-11-13 | Mayur Devjibhai Khunt | Process for purifying valacyclovir hydrochloride and intermediates thereof |
| CN102584825B (zh) * | 2011-01-17 | 2014-04-02 | 四川科伦药物研究有限公司 | 一种合成盐酸伐昔洛韦的方法 |
| US10836765B2 (en) * | 2016-03-03 | 2020-11-17 | Aurobindo Pharma Ltd | Process for the preparation of valacyclovir |
| CN106632335A (zh) * | 2016-12-27 | 2017-05-10 | 河南康达制药有限公司 | 一种盐酸伐昔洛韦的制备方法 |
| CN114621227B (zh) * | 2022-02-28 | 2024-07-09 | 海南久常制药有限公司 | 一种盐酸伐昔洛韦、制剂及其制备方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199574A (en) | 1974-09-02 | 1980-04-22 | Burroughs Wellcome Co. | Methods and compositions for treating viral infections and guanine acyclic nucleosides |
| GB8719367D0 (en) | 1987-08-15 | 1987-09-23 | Wellcome Found | Therapeutic compounds |
| DE69426880T2 (de) * | 1993-06-10 | 2001-10-31 | Rolabo S.L., Zaragoza | Verfahren zur herstellung von aminosäureester von nukleosid analogen |
| GB9501178D0 (en) * | 1995-01-20 | 1995-03-08 | Wellcome Found | Guanine derivative |
| GB9501127D0 (en) * | 1995-01-20 | 1995-03-08 | Wellcome Found | Tablet |
| US6117453A (en) * | 1995-04-14 | 2000-09-12 | Pharma Pass | Solid compositions containing polyethylene oxide and an active ingredient |
| US5672243A (en) * | 1995-11-28 | 1997-09-30 | Mosel Vitelic, Inc. | Antireflection coating for highly reflective photolithographic layers comprising chromium oxide or chromium suboxide |
| PT874631E (pt) * | 1996-01-19 | 2004-04-30 | Glaxo Group Ltd | Utilizacao de valaciclovir para a manufactura de um medicamento para o tratamento de herpes genital por aplicacao diaria unica |
| 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 |
| 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 |
| IT1283447B1 (it) * | 1996-07-18 | 1998-04-21 | Ind Chimica Srl | Processo di preparazione del valaciclovir e relativi intermedi |
| JP2001503767A (ja) * | 1996-11-12 | 2001-03-21 | メディヴィル・アクチボラグ | ヌクレオシド |
| MXPA04002192A (es) * | 2001-09-07 | 2005-02-17 | Teva Pharma | Formas cristalinas de clorhidrato de valaciclovir. |
| US20040197396A1 (en) * | 2001-11-05 | 2004-10-07 | Fain Helen S | Anhydrous crystal form of valaciclovir hydrochloride |
| MX242714B (es) * | 2001-11-14 | 2006-12-15 | Teva Pharma | Sintesis y purificacion de valaciclovir. |
| AU2003240213A1 (en) * | 2002-06-24 | 2004-01-06 | Ranbaxy Laboratories Limited | Process for the preparation of robust formulations of valacyclovir hydrochloride tablets |
| US20050043329A1 (en) * | 2002-09-06 | 2005-02-24 | Shlomit Wizel | Crystalline forms of valacyclovir hydrochloride |
| US20050059684A1 (en) * | 2002-10-16 | 2005-03-17 | Ben-Zion Dolitzky | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| EP1551838B1 (en) * | 2002-10-16 | 2006-08-09 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| AU2003289995A1 (en) * | 2002-12-09 | 2004-06-30 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| WO2004106338A1 (en) * | 2003-05-30 | 2004-12-09 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| EP2014660A3 (en) * | 2003-06-02 | 2009-07-15 | Teva Pharmaceutical Industries Ltd | Novel crystalline forms of valacyclovir hydrochloride |
| EP1706406A1 (en) * | 2004-01-21 | 2006-10-04 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of valacyclovir hydrochloride |
| US20060178512A1 (en) * | 2005-02-04 | 2006-08-10 | Cheruthur Govindan | Method for preparing amino acid esters of nucleoside analogues |
| EP1746098A1 (en) * | 2005-07-21 | 2007-01-24 | SOLMAG S.p.A. | Valacyclovir polymorphs and a process for the preparation thereof |
| US20070112193A1 (en) * | 2005-11-14 | 2007-05-17 | Khunt Mayur D | Valacyclovir process |
| US20080281099A1 (en) * | 2007-05-07 | 2008-11-13 | Mayur Devjibhai Khunt | Process for purifying valacyclovir hydrochloride and intermediates thereof |
-
2002
- 2002-11-13 MX MXPA04004656 patent/MX242714B/es active IP Right Grant
- 2002-11-13 KR KR1020047007289A patent/KR20050044449A/ko not_active Ceased
- 2002-11-13 JP JP2003543534A patent/JP2005508993A/ja not_active Withdrawn
- 2002-11-13 KR KR1020077002062A patent/KR20070020149A/ko not_active Ceased
- 2002-11-13 EP EP02793918A patent/EP1465894A4/en not_active Withdrawn
- 2002-11-13 CN CNB028268970A patent/CN1307177C/zh not_active Expired - Fee Related
- 2002-11-13 CA CA002465928A patent/CA2465928C/en not_active Expired - Fee Related
- 2002-11-13 CA CA002649826A patent/CA2649826A1/en not_active Abandoned
- 2002-11-13 IL IL16196902A patent/IL161969A0/xx unknown
- 2002-11-13 WO PCT/US2002/036269 patent/WO2003041647A2/en not_active Ceased
- 2002-11-13 US US10/293,347 patent/US6849737B2/en not_active Expired - Fee Related
- 2002-11-13 PL PL02371732A patent/PL371732A1/xx not_active Application Discontinuation
- 2002-11-13 HR HR20040511A patent/HRP20040511A2/hr not_active Application Discontinuation
-
2004
- 2004-05-11 IS IS7260A patent/IS7260A/is unknown
- 2004-06-11 NO NO20042433A patent/NO20042433L/no not_active Application Discontinuation
-
2005
- 2005-01-25 US US11/042,538 patent/US20050130993A1/en not_active Abandoned
-
2007
- 2007-06-05 IN IN4250DE2007 patent/IN2007DE04250A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1465894A4 (en) | 2008-10-08 |
| WO2003041647A2 (en) | 2003-05-22 |
| KR20070020149A (ko) | 2007-02-16 |
| JP2005508993A (ja) | 2005-04-07 |
| IN2007DE04250A (en:Method) | 2007-08-31 |
| NO20042433L (no) | 2004-07-22 |
| CA2465928A1 (en) | 2003-05-22 |
| EP1465894A2 (en) | 2004-10-13 |
| MX242714B (es) | 2006-12-15 |
| CN1307177C (zh) | 2007-03-28 |
| HRP20040511A2 (en) | 2004-10-31 |
| KR20050044449A (ko) | 2005-05-12 |
| MXPA04004656A (es) | 2004-08-13 |
| IL161969A0 (en) | 2005-11-20 |
| IS7260A (is) | 2004-05-11 |
| US20030153757A1 (en) | 2003-08-14 |
| PL371732A1 (en) | 2005-06-27 |
| CN1612878A (zh) | 2005-05-04 |
| CA2649826A1 (en) | 2003-05-22 |
| US20050130993A1 (en) | 2005-06-16 |
| US6849737B2 (en) | 2005-02-01 |
| WO2003041647A3 (en) | 2003-11-20 |
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| Publication | Publication Date | Title |
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