JP2005511612A - 塩酸バラシクロビルの無水結晶形 - Google Patents
塩酸バラシクロビルの無水結晶形 Download PDFInfo
- Publication number
- JP2005511612A JP2005511612A JP2003542191A JP2003542191A JP2005511612A JP 2005511612 A JP2005511612 A JP 2005511612A JP 2003542191 A JP2003542191 A JP 2003542191A JP 2003542191 A JP2003542191 A JP 2003542191A JP 2005511612 A JP2005511612 A JP 2005511612A
- Authority
- JP
- Japan
- Prior art keywords
- valaciclovir hydrochloride
- anhydrous crystalline
- anhydrous
- hydrochloride
- hydrated
- 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.)
- Pending
Links
- 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 title claims abstract description 295
- 239000013078 crystal Substances 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 94
- 239000002904 solvent Substances 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 32
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 25
- 238000002441 X-ray diffraction Methods 0.000 claims description 25
- 238000010533 azeotropic distillation Methods 0.000 claims description 25
- 238000001228 spectrum Methods 0.000 claims description 23
- 238000001237 Raman spectrum Methods 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 19
- 230000002265 prevention Effects 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
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- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
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- 201000001320 Atherosclerosis Diseases 0.000 description 3
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 3
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- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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- KNOVZDRKHSHEQN-JZGIKJSDSA-N 2-[(2-amino-6-oxo-3h-purin-9-yl)methoxy]ethyl (2s)-2-amino-3-methylbutanoate;hydrate;hydrochloride Chemical compound O.Cl.N1=C(N)NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 KNOVZDRKHSHEQN-JZGIKJSDSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-Valine Natural products CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
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- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
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- 229960001627 lamivudine Drugs 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
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- 229960004295 valine Drugs 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
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- 230000004580 weight loss Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33331301P | 2001-11-05 | 2001-11-05 | |
| PCT/US2002/033926 WO2003040145A1 (en) | 2001-11-05 | 2002-10-23 | Anhydrous crystal form of valaciclovir hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005511612A true JP2005511612A (ja) | 2005-04-28 |
| JP2005511612A5 JP2005511612A5 (enExample) | 2005-12-22 |
Family
ID=23302261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003542191A Pending JP2005511612A (ja) | 2001-11-05 | 2002-10-23 | 塩酸バラシクロビルの無水結晶形 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20040197396A1 (enExample) |
| EP (1) | EP1453834A1 (enExample) |
| JP (1) | JP2005511612A (enExample) |
| AU (1) | AU2002348022B2 (enExample) |
| CA (1) | CA2465420A1 (enExample) |
| FR (1) | FR2831885A1 (enExample) |
| GB (1) | GB2383038B (enExample) |
| GR (1) | GR1004358B (enExample) |
| IT (1) | ITRM20020555A1 (enExample) |
| WO (1) | WO2003040145A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2009031576A1 (ja) * | 2007-09-03 | 2010-12-16 | 味の素株式会社 | バラシクロビル塩酸塩結晶の製造方法 |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0500753A3 (en) * | 2001-09-07 | 2006-05-29 | Teva Pharma | Crystalline forms of valacyclovir hydrochloride |
| EP1453834A1 (en) * | 2001-11-05 | 2004-09-08 | Glaxo Group Limited | 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 |
| CA2548608A1 (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 |
| US20050085491A1 (en) * | 2003-06-02 | 2005-04-21 | Igor Lifshitz | Novel crystalline forms of valacyclovir hydrochloride |
| CN1331471C (zh) * | 2003-09-22 | 2007-08-15 | 陈云芳 | 盐酸万乃洛韦软胶囊组合物 |
| EP1746098A1 (en) * | 2005-07-21 | 2007-01-24 | SOLMAG S.p.A. | Valacyclovir polymorphs and a process for the preparation thereof |
| US20080167325A1 (en) * | 2006-12-27 | 2008-07-10 | Bs Praveen Kumar | Valacyclovir compositions |
| WO2011158252A1 (en) | 2010-06-15 | 2011-12-22 | Matrix Laboratories Ltd | Process for the preparation of valacyclovir hydrochloride polymorphic form ii |
| CN105753868B (zh) * | 2016-04-12 | 2017-08-01 | 浙江理工大学 | 一种盐酸伐昔洛韦的半水合物及其制备方法 |
| CN112176011B (zh) * | 2020-10-26 | 2022-10-18 | 辰欣药业股份有限公司 | 一种酶催化制备盐酸伐昔洛韦的方法 |
| CN116754538B (zh) * | 2023-06-15 | 2024-05-07 | 深圳市新阳唯康科技有限公司 | 一种阿昔洛韦软膏的晶型定量方法 |
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| 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 |
| GB9501127D0 (en) * | 1995-01-20 | 1995-03-08 | Wellcome Found | Tablet |
| GB9501178D0 (en) * | 1995-01-20 | 1995-03-08 | Wellcome Found | Guanine derivative |
| HUP0500753A3 (en) * | 2001-09-07 | 2006-05-29 | Teva Pharma | Crystalline forms of valacyclovir hydrochloride |
| EP1453834A1 (en) * | 2001-11-05 | 2004-09-08 | Glaxo Group Limited | 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 |
| WO2004035583A1 (en) * | 2002-10-16 | 2004-04-29 | Teva Pharmaceutical Industries Ltd. | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| US20050059684A1 (en) * | 2002-10-16 | 2005-03-17 | Ben-Zion Dolitzky | Method for reducing residual alcohols in crystalline valacyclovir hydrochloride |
| CA2548608A1 (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 |
| US20050085491A1 (en) * | 2003-06-02 | 2005-04-21 | Igor Lifshitz | Novel crystalline forms of valacyclovir hydrochloride |
| KR20060117355A (ko) * | 2004-01-21 | 2006-11-16 | 테바 파마슈티컬 인더스트리즈 리미티드 | 발라시클로버 염산염의 제조 방법 |
| 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 |
-
2002
- 2002-10-23 EP EP02784234A patent/EP1453834A1/en not_active Withdrawn
- 2002-10-23 CA CA002465420A patent/CA2465420A1/en not_active Abandoned
- 2002-10-23 JP JP2003542191A patent/JP2005511612A/ja active Pending
- 2002-10-23 WO PCT/US2002/033926 patent/WO2003040145A1/en not_active Ceased
- 2002-10-23 US US10/494,115 patent/US20040197396A1/en not_active Abandoned
- 2002-10-23 AU AU2002348022A patent/AU2002348022B2/en not_active Ceased
- 2002-11-04 FR FR0213752A patent/FR2831885A1/fr not_active Withdrawn
- 2002-11-05 IT IT000555A patent/ITRM20020555A1/it unknown
- 2002-11-05 GR GR20020100478A patent/GR1004358B/el unknown
- 2002-11-05 GB GB0225771A patent/GB2383038B/en not_active Expired - Fee Related
-
2006
- 2006-10-24 US US11/552,218 patent/US20070093511A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2009031576A1 (ja) * | 2007-09-03 | 2010-12-16 | 味の素株式会社 | バラシクロビル塩酸塩結晶の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GR20020100478A (el) | 2003-07-16 |
| GB0225771D0 (en) | 2002-12-11 |
| FR2831885A1 (fr) | 2003-05-09 |
| WO2003040145A1 (en) | 2003-05-15 |
| GB2383038B (en) | 2005-01-19 |
| EP1453834A1 (en) | 2004-09-08 |
| US20040197396A1 (en) | 2004-10-07 |
| GR1004358B (el) | 2003-10-07 |
| AU2002348022B2 (en) | 2006-06-15 |
| CA2465420A1 (en) | 2003-05-15 |
| ITRM20020555A1 (it) | 2003-05-06 |
| ITRM20020555A0 (it) | 2002-11-05 |
| US20070093511A1 (en) | 2007-04-26 |
| GB2383038A (en) | 2003-06-18 |
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