JP2005508993A5 - - Google Patents
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- Publication number
- JP2005508993A5 JP2005508993A5 JP2003543534A JP2003543534A JP2005508993A5 JP 2005508993 A5 JP2005508993 A5 JP 2005508993A5 JP 2003543534 A JP2003543534 A JP 2003543534A JP 2003543534 A JP2003543534 A JP 2003543534A JP 2005508993 A5 JP2005508993 A5 JP 2005508993A5
- Authority
- JP
- Japan
- Prior art keywords
- valine
- valaciclovir
- protected
- pure
- valaciclovir hydrochloride
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 claims 32
- ZCDDBUOENGJMLV-QRPNPIFTSA-N Valacyclovir hydrochloride Chemical compound Cl.N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 ZCDDBUOENGJMLV-QRPNPIFTSA-N 0.000 claims 22
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 16
- 229960004295 valine Drugs 0.000 claims 16
- 239000004474 valine Substances 0.000 claims 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 12
- 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 claims 10
- 239000002002 slurry Substances 0.000 claims 10
- 238000010511 deprotection reaction Methods 0.000 claims 9
- 229940093257 valacyclovir Drugs 0.000 claims 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- 229960004150 aciclovir Drugs 0.000 claims 8
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 8
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 7
- 239000007822 coupling agent Substances 0.000 claims 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- 150000001718 carbodiimides Chemical group 0.000 claims 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 5
- 230000008878 coupling Effects 0.000 claims 5
- 238000010168 coupling process Methods 0.000 claims 5
- 238000005859 coupling reaction Methods 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 239000000243 solution Substances 0.000 claims 5
- QBYYLBWFBPAOKU-YFKPBYRVSA-N (2s)-2-formamido-3-methylbutanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC=O QBYYLBWFBPAOKU-YFKPBYRVSA-N 0.000 claims 4
- 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 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000005233 alkylalcohol group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 239000002552 dosage form Substances 0.000 claims 4
- 235000019253 formic acid Nutrition 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000012535 impurity Substances 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 239000006186 oral dosage form Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241001529453 unidentified herpesvirus Species 0.000 claims 2
- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 claims 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- -1 aminopropyl Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940064636 valacyclovir hydrochloride Drugs 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33280201P | 2001-11-14 | 2001-11-14 | |
| US34227301P | 2001-12-21 | 2001-12-21 | |
| PCT/US2002/036269 WO2003041647A2 (en) | 2001-11-14 | 2002-11-13 | Synthesis and purification of valacyclovir |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508993A JP2005508993A (ja) | 2005-04-07 |
| JP2005508993A5 true JP2005508993A5 (enExample) | 2005-12-22 |
Family
ID=26988392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003543534A Withdrawn JP2005508993A (ja) | 2001-11-14 | 2002-11-13 | バラシクロビルの合成及び精製 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6849737B2 (enExample) |
| EP (1) | EP1465894A4 (enExample) |
| JP (1) | JP2005508993A (enExample) |
| KR (2) | KR20070020149A (enExample) |
| CN (1) | CN1307177C (enExample) |
| CA (2) | CA2649826A1 (enExample) |
| HR (1) | HRP20040511A2 (enExample) |
| IL (1) | IL161969A0 (enExample) |
| IN (1) | IN2007DE04250A (enExample) |
| IS (1) | IS7260A (enExample) |
| MX (1) | MX242714B (enExample) |
| NO (1) | NO20042433L (enExample) |
| PL (1) | PL371732A1 (enExample) |
| WO (1) | WO2003041647A2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL374179A1 (en) * | 2001-09-07 | 2005-10-03 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of valacyclovir hydrochloride |
| JP2005511612A (ja) * | 2001-11-05 | 2005-04-28 | グラクソ グループ リミテッド | 塩酸バラシクロビルの無水結晶形 |
| US6849737B2 (en) * | 2001-11-14 | 2005-02-01 | Teva Pharmaceutical Industries Ltd. | Synthesis and purification of valacyclovir |
| US20050043329A1 (en) * | 2002-09-06 | 2005-02-24 | Shlomit Wizel | Crystalline forms of valacyclovir hydrochloride |
| ES2270172T3 (es) * | 2002-10-16 | 2007-04-01 | Teva Pharmaceutical Industries Ltd. | Procedimiento para reducir alcoholes residuales en hidrocloruro de valaciclovir cristalino. |
| US20050059684A1 (en) * | 2002-10-16 | 2005-03-17 | Ben-Zion Dolitzky | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| US20060229322A1 (en) * | 2002-12-09 | 2006-10-12 | Pau Cid | Anhydrous crystalline form of valacyclovir hydrochloride |
| US7786302B2 (en) * | 2003-05-30 | 2010-08-31 | Eczacibasi-Zentiva Kimyasal Urunler Sanayi Ve Ticaret A.S. | Crystalline forms of valacyclovir hydrochloride |
| US20050085491A1 (en) * | 2003-06-02 | 2005-04-21 | Igor Lifshitz | Novel crystalline forms of valacyclovir hydrochloride |
| US20050192296A1 (en) * | 2004-01-21 | 2005-09-01 | Zvi Harel | 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 |
| US7629461B2 (en) * | 2004-09-04 | 2009-12-08 | Teva Pharmaceutical Industries Ltd | Isolated valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard |
| 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 |
| WO2008139539A1 (ja) * | 2007-04-27 | 2008-11-20 | Ajinomoto Co., Inc. | 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 |
| ATE199719T1 (de) * | 1993-06-10 | 2001-03-15 | Rolabo Sl | 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 |
| WO1997025989A1 (en) * | 1996-01-19 | 1997-07-24 | Glaxo Group Limited | Use of valaciclovir for the manufacture of a medicament for the treatment of genital herpes by a single daily application |
| 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 |
| PL374179A1 (en) * | 2001-09-07 | 2005-10-03 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of valacyclovir hydrochloride |
| JP2005511612A (ja) * | 2001-11-05 | 2005-04-28 | グラクソ グループ リミテッド | 塩酸バラシクロビルの無水結晶形 |
| US6849737B2 (en) * | 2001-11-14 | 2005-02-01 | Teva Pharmaceutical Industries Ltd. | Synthesis and purification of valacyclovir |
| WO2004000265A2 (en) * | 2002-06-24 | 2003-12-31 | 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 |
| ES2270172T3 (es) * | 2002-10-16 | 2007-04-01 | Teva Pharmaceutical Industries Ltd. | Procedimiento para reducir alcoholes residuales en hidrocloruro de valaciclovir cristalino. |
| US20050059684A1 (en) * | 2002-10-16 | 2005-03-17 | Ben-Zion Dolitzky | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| US20060229322A1 (en) * | 2002-12-09 | 2006-10-12 | Pau Cid | Anhydrous crystalline form of valacyclovir hydrochloride |
| US7786302B2 (en) * | 2003-05-30 | 2010-08-31 | Eczacibasi-Zentiva Kimyasal Urunler Sanayi Ve Ticaret A.S. | Crystalline forms of valacyclovir hydrochloride |
| US20050085491A1 (en) * | 2003-06-02 | 2005-04-21 | Igor Lifshitz | Novel crystalline forms of valacyclovir hydrochloride |
| US20050192296A1 (en) * | 2004-01-21 | 2005-09-01 | Zvi Harel | 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 US US10/293,347 patent/US6849737B2/en not_active Expired - Fee Related
- 2002-11-13 EP EP02793918A patent/EP1465894A4/en not_active Withdrawn
- 2002-11-13 CA CA002649826A patent/CA2649826A1/en not_active Abandoned
- 2002-11-13 HR HR20040511A patent/HRP20040511A2/hr not_active Application Discontinuation
- 2002-11-13 CN CNB028268970A patent/CN1307177C/zh not_active Expired - Fee Related
- 2002-11-13 IL IL16196902A patent/IL161969A0/xx unknown
- 2002-11-13 MX MXPA04004656 patent/MX242714B/es active IP Right Grant
- 2002-11-13 CA CA002465928A patent/CA2465928C/en not_active Expired - Fee Related
- 2002-11-13 JP JP2003543534A patent/JP2005508993A/ja not_active Withdrawn
- 2002-11-13 PL PL02371732A patent/PL371732A1/xx not_active Application Discontinuation
- 2002-11-13 KR KR1020077002062A patent/KR20070020149A/ko not_active Ceased
- 2002-11-13 WO PCT/US2002/036269 patent/WO2003041647A2/en not_active Ceased
- 2002-11-13 KR KR1020047007289A patent/KR20050044449A/ko not_active Ceased
-
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
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