JP2005508993A5 - - Google Patents
Download PDFInfo
- 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- Withdrawn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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1465894A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2005508993A (cg-RX-API-DMAC7.html) |
| KR (2) | KR20050044449A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1307177C (cg-RX-API-DMAC7.html) |
| CA (2) | CA2649826A1 (cg-RX-API-DMAC7.html) |
| HR (1) | HRP20040511A2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL161969A0 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2007DE04250A (cg-RX-API-DMAC7.html) |
| IS (1) | IS7260A (cg-RX-API-DMAC7.html) |
| MX (1) | MX242714B (cg-RX-API-DMAC7.html) |
| NO (1) | NO20042433L (cg-RX-API-DMAC7.html) |
| PL (1) | PL371732A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003041647A2 (cg-RX-API-DMAC7.html) |
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 |
| IL161969A0 (en) * | 2001-11-14 | 2005-11-20 | Teva Pharma | Synthesis and purification of valacyclovir |
| 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 |
| AU2003277433A1 (en) * | 2002-10-16 | 2004-05-04 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| WO2004052892A1 (en) * | 2002-12-09 | 2004-06-24 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| EP1633753A1 (en) * | 2003-05-30 | 2006-03-15 | EOS Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ti Caret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| KR100871621B1 (ko) * | 2003-06-02 | 2008-12-02 | 테바 파마슈티컬 인더스트리즈 리미티드 | 발라시클로비르 히드로클로라이드의 신규한 결정질 형태 |
| KR20060117355A (ko) * | 2004-01-21 | 2006-11-16 | 테바 파마슈티컬 인더스트리즈 리미티드 | 발라시클로버 염산염의 제조 방법 |
| 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 |
| 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 |
| WO2017149420A1 (en) * | 2016-03-03 | 2017-09-08 | 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 |
| DK0874631T3 (da) * | 1996-01-19 | 2004-03-22 | Glaxo Group Ltd | Anvendelse af valaciclovir til fremstilling af et medikament til behandling af genital herpes ved en enkelt daglig anvendelse |
| 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 |
| AU735438B2 (en) * | 1996-11-12 | 2001-07-05 | Medivir Ab | Nucleosides |
| 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 |
| IL161969A0 (en) * | 2001-11-14 | 2005-11-20 | Teva Pharma | Synthesis and purification of valacyclovir |
| US20060147519A1 (en) * | 2002-06-24 | 2006-07-06 | Ashish Gogia | 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 |
| AU2003277433A1 (en) * | 2002-10-16 | 2004-05-04 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| WO2004052892A1 (en) * | 2002-12-09 | 2004-06-24 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| EP1633753A1 (en) * | 2003-05-30 | 2006-03-15 | EOS Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ti Caret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| KR100871621B1 (ko) * | 2003-06-02 | 2008-12-02 | 테바 파마슈티컬 인더스트리즈 리미티드 | 발라시클로비르 히드로클로라이드의 신규한 결정질 형태 |
| KR20060117355A (ko) * | 2004-01-21 | 2006-11-16 | 테바 파마슈티컬 인더스트리즈 리미티드 | 발라시클로버 염산염의 제조 방법 |
| 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 IL IL16196902A patent/IL161969A0/xx unknown
- 2002-11-13 KR KR1020047007289A patent/KR20050044449A/ko not_active Ceased
- 2002-11-13 CA CA002649826A patent/CA2649826A1/en not_active Abandoned
- 2002-11-13 US US10/293,347 patent/US6849737B2/en not_active Expired - Fee Related
- 2002-11-13 WO PCT/US2002/036269 patent/WO2003041647A2/en not_active Ceased
- 2002-11-13 KR KR1020077002062A patent/KR20070020149A/ko not_active Ceased
- 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 EP EP02793918A patent/EP1465894A4/en not_active Withdrawn
- 2002-11-13 CN CNB028268970A patent/CN1307177C/zh 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 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005508993A5 (cg-RX-API-DMAC7.html) | ||
| CA2465928A1 (en) | Synthesis and purification of valacyclovir | |
| AU2002344419C1 (en) | Alpha-form or beta-form cyrstal of acetanilide derivative | |
| HU193995B (en) | Process for production of esther prodrug formations of derivatives of 3-hydroxi-morphinane formed with substituted bensoic acids and medical preparatives containing these compounds | |
| WO2011083304A1 (en) | Prodrugs of opioids and uses thereof | |
| RU2261860C2 (ru) | ЗАМЕЩЕННЫЕ В ПОЛОЖЕНИИ 8А ПРОИЗВОДНЫЕ 8,8А-ДИГИДРОИНДЕНО [1,2-d] ТИАЗОЛА, СПОСОБ ИХ ПОЛУЧЕНИЯ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ЛЕКАРСТВЕННЫХ СРЕДСТВ, НАПРИМЕР В КАЧЕСТВЕ АНОРЕКСИЧЕСКИХ СРЕДСТВ | |
| IL192233A (en) | Derivatives of N- (arylsulfonyl) beta-amino acids containing converted amino-methyl groups, for the preparation of a drug for the treatment of pain and inflammation | |
| ES2236833T3 (es) | Compuestos heterociclicos de guanidinilo utiles como agonistas de receptores adrenergicos alfa 2. | |
| CA2585983C (en) | Use of 1,4-bis (3-aminoalkyl) piperazine derivatives in the treatment of neurodegenerative diseases | |
| WO2015004599A1 (en) | An improved process for preparing linagliptin and its key intermediates | |
| JP2004531489A (ja) | 抗炎症性および免疫抑制性活性を有する新規ベンズアミジン誘導体 | |
| CN107987033B (zh) | 香草醛及其异构体在制备na抑制剂中的应用 | |
| CN108047160B (zh) | 2-(2-苄亚肼基)-5-酰基噻唑及其医药用途 | |
| CN113214275B (zh) | 吡喃并咔唑生物碱类衍生物及其治疗神经系统疾病的用途 | |
| JP2010501591A (ja) | ３−（３−インドリル）プロピオン酸カルシウム塩およびそれから３−（３−インドリル）プロピオン酸の遊離酸を作る方法 | |
| WO2001081331A1 (en) | Hydrates and crystals of a neuraminic acid compound | |
| CN109053606B (zh) | 4-(4-羟基苯基亚甲氨基)-1,2,4-三唑-5-硫酮及其应用 | |
| CA2537132A1 (en) | Amorphous valganciclovir hydrochloride | |
| CN101781300B (zh) | 一种恩替卡韦的盐化合物，其制备方法和药物应用 | |
| CN117551081A (zh) | 一种偏头痛治疗药物新的制备方法 | |
| AU729421B2 (en) | Guinidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists | |
| AU6514498A (en) | 5-(2-imidazolinylamino)benzimidazole compounds useful as alpha-2 adrenoceptor agonists | |
| WO2013076688A1 (en) | A process for the preparation of valacyclovir hydrochloride | |
| JPH05262770A (ja) | 化学的製法 | |
| EP0710482B1 (en) | Therapeutic agent for myocardial ischemic damages or reperfusion injuries |