FR2831885A1 - Forme cristalline anhydre de chlorhydrate de valaciclovir - Google Patents
Forme cristalline anhydre de chlorhydrate de valaciclovir Download PDFInfo
- Publication number
- FR2831885A1 FR2831885A1 FR0213752A FR0213752A FR2831885A1 FR 2831885 A1 FR2831885 A1 FR 2831885A1 FR 0213752 A FR0213752 A FR 0213752A FR 0213752 A FR0213752 A FR 0213752A FR 2831885 A1 FR2831885 A1 FR 2831885A1
- Authority
- FR
- France
- Prior art keywords
- valaciclovir hydrochloride
- anhydrous crystalline
- hydrochloride
- sep
- solvent
- 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- Withdrawn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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 13
- 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 abstract description 285
- 230000008569 process Effects 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims description 90
- 239000002904 solvent Substances 0.000 claims description 68
- 238000011282 treatment Methods 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 238000001228 spectrum Methods 0.000 claims description 30
- 238000010533 azeotropic distillation Methods 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 238000001237 Raman spectrum Methods 0.000 claims description 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
- 238000011321 prophylaxis Methods 0.000 claims description 21
- 239000000725 suspension Substances 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims description 19
- 238000010586 diagram Methods 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 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 description 12
- 238000002441 X-ray diffraction Methods 0.000 claims description 12
- 238000004064 recycling Methods 0.000 claims description 12
- 229940093257 valacyclovir Drugs 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- 238000000862 absorption spectrum Methods 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 11
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- 235000010446 mineral oil Nutrition 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 10
- 241001529453 unidentified herpesvirus Species 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 C 6 ethers Chemical class 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 238000005481 NMR spectroscopy Methods 0.000 claims description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 6
- 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 claims description 5
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 5
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 4
- 241001502974 Human gammaherpesvirus 8 Species 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- KEKPAPJXCXKIDQ-UHFFFAOYSA-N 4-methylpentan-2-one Chemical compound CC(C)CC(C)=O.CC(C)CC(C)=O KEKPAPJXCXKIDQ-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
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- 238000010438 heat treatment Methods 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002002 slurry Substances 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 1
- 239000011928 denatured alcohol Substances 0.000 claims 1
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- 238000000968 medical method and process Methods 0.000 abstract 1
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- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
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- 230000003612 virological effect Effects 0.000 description 5
- 229910000530 Gallium indium arsenide Inorganic materials 0.000 description 4
- 229960004150 aciclovir Drugs 0.000 description 4
- 238000002399 angioplasty Methods 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
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- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 3
- 229910001634 calcium fluoride Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000036571 hydration Effects 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
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- 230000001629 suppression Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010056489 Coronary artery restenosis Diseases 0.000 description 2
- 208000005156 Dehydration Diseases 0.000 description 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
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- 230000003247 decreasing effect Effects 0.000 description 2
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- 239000002274 desiccant Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 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
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-Valine Natural products CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 208000032420 Latent Infection Diseases 0.000 description 1
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
- 229960004748 abacavir Drugs 0.000 description 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
- 229960001830 amprenavir Drugs 0.000 description 1
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
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- 150000007942 carboxylates Chemical group 0.000 description 1
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- 229940075894 denatured ethanol Drugs 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- 238000007416 differential thermogravimetric analysis Methods 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 208000037771 disease arising from reactivation of latent virus Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229960004396 famciclovir Drugs 0.000 description 1
- 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
- 230000004927 fusion Effects 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
- 229960002963 ganciclovir Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 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
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
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- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 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
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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33331301P | 2001-11-05 | 2001-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2831885A1 true FR2831885A1 (fr) | 2003-05-09 |
Family
ID=23302261
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR0213752A Withdrawn FR2831885A1 (fr) | 2001-11-05 | 2002-11-04 | Forme cristalline anhydre de chlorhydrate de valaciclovir |
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 |
|---|---|---|---|---|
| EP1746098A1 (en) * | 2005-07-21 | 2007-01-24 | SOLMAG S.p.A. | Valacyclovir polymorphs and a process for the preparation thereof |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5043286B2 (ja) * | 2001-09-07 | 2012-10-10 | テバ ファーマシューティカル インダストリーズ リミティド | バラシクロビル塩酸塩の結晶型 |
| AU2002348022B2 (en) * | 2001-11-05 | 2006-06-15 | Glaxo Group Limited | Anhydrous crystal form of valaciclovir hydrochloride |
| CA2465928C (en) * | 2001-11-14 | 2010-01-19 | Teva Pharmaceutical Industries Ltd. | Synthesis and purification of valacyclovir |
| US20050043329A1 (en) * | 2002-09-06 | 2005-02-24 | Shlomit Wizel | Crystalline forms of valacyclovir hydrochloride |
| EP1575953A1 (en) * | 2002-12-09 | 2005-09-21 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| AU2003232719A1 (en) * | 2003-05-30 | 2005-01-21 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| EP1638972A2 (en) * | 2003-06-02 | 2006-03-29 | Teva Pharmaceutical Industries Limited | 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 |
| US20080167325A1 (en) * | 2006-12-27 | 2008-07-10 | Bs Praveen Kumar | Valacyclovir compositions |
| WO2009031576A1 (ja) * | 2007-09-03 | 2009-03-12 | Ajinomoto Co., Inc. | バラシクロビル塩酸塩結晶の製造方法 |
| 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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| US4957924A (en) * | 1987-08-15 | 1990-09-18 | Burroughs Wellcome Co. | Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof |
| US6107302A (en) * | 1995-01-20 | 2000-08-22 | Glaxo Wellcome Inc. | Guanine derivative |
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| 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 |
| GB9501127D0 (en) * | 1995-01-20 | 1995-03-08 | Wellcome Found | Tablet |
| JP5043286B2 (ja) * | 2001-09-07 | 2012-10-10 | テバ ファーマシューティカル インダストリーズ リミティド | バラシクロビル塩酸塩の結晶型 |
| AU2002348022B2 (en) * | 2001-11-05 | 2006-06-15 | Glaxo Group Limited | Anhydrous crystal form of valaciclovir hydrochloride |
| CA2465928C (en) * | 2001-11-14 | 2010-01-19 | Teva Pharmaceutical Industries Ltd. | 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 |
| EP1575953A1 (en) * | 2002-12-09 | 2005-09-21 | Texcontor Etablissement | Anhydrous crystalline form of valacyclovir hydrochloride |
| AU2003232719A1 (en) * | 2003-05-30 | 2005-01-21 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S. | Novel crystalline forms of valacyclovir hydrochloride |
| EP1638972A2 (en) * | 2003-06-02 | 2006-03-29 | Teva Pharmaceutical Industries Limited | 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 AU AU2002348022A patent/AU2002348022B2/en not_active Ceased
- 2002-10-23 EP EP02784234A patent/EP1453834A1/en not_active Withdrawn
- 2002-10-23 JP JP2003542191A patent/JP2005511612A/ja active Pending
- 2002-10-23 US US10/494,115 patent/US20040197396A1/en not_active Abandoned
- 2002-10-23 CA CA002465420A patent/CA2465420A1/en not_active Abandoned
- 2002-10-23 WO PCT/US2002/033926 patent/WO2003040145A1/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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4957924A (en) * | 1987-08-15 | 1990-09-18 | Burroughs Wellcome Co. | Therapeutic valine esters of acyclovir and pharmaceutically acceptable salts thereof |
| US6107302A (en) * | 1995-01-20 | 2000-08-22 | Glaxo Wellcome Inc. | Guanine derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1746098A1 (en) * | 2005-07-21 | 2007-01-24 | SOLMAG S.p.A. | Valacyclovir polymorphs and a process for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002348022B2 (en) | 2006-06-15 |
| GB2383038B (en) | 2005-01-19 |
| GB0225771D0 (en) | 2002-12-11 |
| ITRM20020555A1 (it) | 2003-05-06 |
| GB2383038A (en) | 2003-06-18 |
| GR1004358B (el) | 2003-10-07 |
| CA2465420A1 (en) | 2003-05-15 |
| GR20020100478A (el) | 2003-07-16 |
| EP1453834A1 (en) | 2004-09-08 |
| JP2005511612A (ja) | 2005-04-28 |
| US20040197396A1 (en) | 2004-10-07 |
| WO2003040145A1 (en) | 2003-05-15 |
| US20070093511A1 (en) | 2007-04-26 |
| ITRM20020555A0 (it) | 2002-11-05 |
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