NO315558B1 - Vannfri krystallinsk form av valaciclovir-hydroklorid - Google Patents

Vannfri krystallinsk form av valaciclovir-hydroklorid Download PDF

Info

Publication number: NO315558B1
Authority: NO; Norway
Prior art keywords: hydrochloride; valaciclovir hydrochloride; valaciclovir; weight; crystalline form
Prior art date: 1995-01-20

Application number

NO19973326A

Other languages

English (en)

Norwegian (no)

Other versions

NO973326D0 (no

NO973326L (no

Inventor

Barry Howard Carter

Jane Muse Partin

Peter Gregory Varlashkin

Richard Augustus Winnike

Philip George Lake

David Michael Skinner

David James Whatrup

Gregory Alan Conway

Iii William Bayne Grubb

Original Assignee

Wellcome Found

Priority date (The priority date 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 date listed.)

1995-01-20

Filing date

1997-07-18

Publication date

2003-09-22

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10768347&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO315558(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-07-18 Application filed by Wellcome Found filed Critical Wellcome Found

1997-07-18 Publication of NO973326D0 publication Critical patent/NO973326D0/no

1997-09-16 Publication of NO973326L publication Critical patent/NO973326L/no

2003-09-22 Publication of NO315558B1 publication Critical patent/NO315558B1/no

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 description 94
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 56
238000000034 method Methods 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000843 powder Substances 0.000 claims description 15
238000000634 powder X-ray diffraction Methods 0.000 claims description 14
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 13
239000013078 crystal Substances 0.000 claims description 13
238000009472 formulation Methods 0.000 claims description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
239000004615 ingredient Substances 0.000 claims description 12
230000003381 solubilizing effect Effects 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
229940093257 valacyclovir Drugs 0.000 claims description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
239000008187 granular material Substances 0.000 claims description 9
230000036571 hydration Effects 0.000 claims description 9
238000006703 hydration reaction Methods 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000007787 solid Substances 0.000 claims description 9
239000003826 tablet Substances 0.000 claims description 9
150000002576 ketones Chemical class 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
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 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
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150000003839 salts Chemical group 0.000 claims description 5
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239000000546 pharmaceutical excipient Substances 0.000 claims description 4
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239000002552 dosage form Substances 0.000 claims description 3
239000003701 inert diluent Substances 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims description 3
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239000004094 surface-active agent Substances 0.000 claims description 3
208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 2
239000013557 residual solvent Substances 0.000 claims 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
150000001875 compounds Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
229960004150 aciclovir Drugs 0.000 description 9
239000011928 denatured alcohol Substances 0.000 description 9
-1 L-valine ester Chemical class 0.000 description 7
239000000725 suspension Substances 0.000 description 7
238000002441 X-ray diffraction Methods 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-Valine Natural products CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 5
230000000840 anti-viral effect Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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CANZBRDGRHNSGZ-NSHDSACASA-N (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-NSHDSACASA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000010586 diagram Methods 0.000 description 4
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229960004295 valine Drugs 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
230000037396 body weight Effects 0.000 description 3
229940075614 colloidal silicon dioxide Drugs 0.000 description 3
238000007906 compression Methods 0.000 description 3
230000006835 compression Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229940069328 povidone Drugs 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000001629 suppression Effects 0.000 description 3
208000007514 Herpes zoster Diseases 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
241000700588 Human alphaherpesvirus 1 Species 0.000 description 2
241000701074 Human alphaherpesvirus 2 Species 0.000 description 2
241000701027 Human herpesvirus 6 Species 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
241000700605 Viruses Species 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000011835 investigation Methods 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011812 mixed powder Substances 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
230000000877 morphologic effect Effects 0.000 description 2
238000000465 moulding Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
230000003612 virological effect Effects 0.000 description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000701022 Cytomegalovirus Species 0.000 description 1
206010011831 Cytomegalovirus infection Diseases 0.000 description 1
241000450599 DNA viruses Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
208000001688 Herpes Genitalis Diseases 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
206010019973 Herpes virus infection Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
101000870363 Oryctolagus cuniculus Glutathione S-transferase Yc Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920003081 Povidone K 30 Polymers 0.000 description 1
208000005181 Varicella Zoster Virus Infection Diseases 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
208000000260 Warts Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
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238000013270 controlled release Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
229960000913 crospovidone Drugs 0.000 description 1
238000013480 data collection Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
150000004683 dihydrates Chemical group 0.000 description 1
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239000000796 flavoring agent Substances 0.000 description 1
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235000013355 food flavoring agent Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
201000004946 genital herpes Diseases 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
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235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
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239000007932 molded tablet Substances 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
238000012856 packing Methods 0.000 description 1
208000003154 papilloma Diseases 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000008213 purified water Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
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239000006068 taste-masking agent Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
KZSNJWFQEVHDMF-UHFFFAOYSA-M valinate Chemical compound CC(C)C(N)C([O-])=O KZSNJWFQEVHDMF-UHFFFAOYSA-M 0.000 description 1
208000010531 varicella zoster infection Diseases 0.000 description 1
239000007762 w/o emulsion Substances 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
229960002555 zidovudine Drugs 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- 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
- 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)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)

NO19973326A 1995-01-20 1997-07-18 Vannfri krystallinsk form av valaciclovir-hydroklorid NO315558B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9501178.9A GB9501178D0 (en)	1995-01-20	1995-01-20	Guanine derivative
PCT/GB1996/000117 WO1996022291A1 (fr)	1995-01-20	1996-01-19	Derive de guanine

Publications (3)

Publication Number	Publication Date
NO973326D0 NO973326D0 (no)	1997-07-18
NO973326L NO973326L (no)	1997-09-16
NO315558B1 true NO315558B1 (no)	2003-09-22

Family

ID=10768347

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19973326A NO315558B1 (no)	1995-01-20	1997-07-18	Vannfri krystallinsk form av valaciclovir-hydroklorid

Country Status (40)

Country	Link
US (1)	US6107302A (fr)
EP (1)	EP0804436B1 (fr)
JP (1)	JP3176633B2 (fr)
KR (1)	KR100376074B1 (fr)
CN (1)	CN1049893C (fr)
AP (1)	AP662A (fr)
AR (1)	AR002270A1 (fr)
AT (1)	ATE302777T1 (fr)
AU (1)	AU702794B2 (fr)
BG (1)	BG63393B1 (fr)
BR (1)	BR9606768A (fr)
CA (1)	CA2210799C (fr)
CY (1)	CY2531B1 (fr)
CZ (1)	CZ297065B6 (fr)
DE (1)	DE69635106T2 (fr)
DK (1)	DK0804436T3 (fr)
EA (1)	EA000364B1 (fr)
EE (1)	EE03528B1 (fr)
ES (1)	ES2248806T3 (fr)
FI (1)	FI973063L (fr)
GB (1)	GB9501178D0 (fr)
GE (1)	GEP20001940B (fr)
HR (1)	HRP960024B1 (fr)
HU (1)	HU222993B1 (fr)
IL (1)	IL116831A (fr)
IN (1)	IN182468B (fr)
IS (1)	IS2268B (fr)
NO (1)	NO315558B1 (fr)
NZ (1)	NZ298851A (fr)
OA (1)	OA10499A (fr)
PL (1)	PL182175B1 (fr)
RO (1)	RO118693B1 (fr)
RS (1)	RS49518B (fr)
SI (1)	SI0804436T1 (fr)
SK (1)	SK285329B6 (fr)
TR (1)	TR199700656T1 (fr)
UA (1)	UA46001C2 (fr)
UY (1)	UY25779A1 (fr)
WO (1)	WO1996022291A1 (fr)
ZA (1)	ZA96449B (fr)

Families Citing this family (61)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9501178D0 (en) *	1995-01-20	1995-03-08	Wellcome Found	Guanine derivative
EP0874631B1 (fr) *	1996-01-19	2003-11-19	Glaxo Group Limited	Utilisation de valaciclovir dans la fabrication d'un medicament destine au traitement de l'herpes genital par administration journaliere unique
IT1283447B1 (it) *	1996-07-18	1998-04-21	Ind Chimica Srl	Processo di preparazione del valaciclovir e relativi intermedi
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1995
- 1995-01-20 GB GBGB9501178.9A patent/GB9501178D0/en active Pending
1996
- 1996-01-19 RS YU3396A patent/RS49518B/sr unknown
- 1996-01-19 IL IL11683196A patent/IL116831A/en not_active IP Right Cessation
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- 1996-01-19 CA CA002210799A patent/CA2210799C/fr not_active Expired - Fee Related
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- 1996-01-19 AU AU44539/96A patent/AU702794B2/en not_active Ceased
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- 1996-01-19 AT AT96900631T patent/ATE302777T1/de not_active IP Right Cessation
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- 1996-01-19 WO PCT/GB1996/000117 patent/WO1996022291A1/fr not_active Ceased
1997
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Publication number	Publication date
CY2531B1 (en)	2006-04-12
HUP9801836A3 (en)	1999-06-28
PL182175B1 (pl)	2001-11-30
IS2268B (is)	2007-07-15
TR199700656T1 (xx)	1998-03-21
MX9705462A (es)	1997-10-31
CA2210799C (fr)	2008-06-10
JPH11503718A (ja)	1999-03-30
GEP20001940B (en)	2000-02-05
YU3396A (sh)	1998-12-23
WO1996022291A1 (fr)	1996-07-25
CZ229497A3 (en)	1997-12-17
DK0804436T3 (da)	2005-12-27
SI0804436T1 (sl)	2006-02-28
IL116831A0 (en)	1996-05-14
SK285329B6 (sk)	2006-11-03
CA2210799A1 (fr)	1996-07-25
EE9700175A (et)	1998-02-16
AP9701058A0 (en)	1997-10-31
DE69635106T2 (de)	2006-06-08
IN182468B (fr)	1999-04-17
RO118693B1 (ro)	2003-09-30
PL321326A1 (en)	1997-12-08
AU702794B2 (en)	1999-03-04
JP3176633B2 (ja)	2001-06-18
UY25779A1 (es)	2000-08-21
AR002270A1 (es)	1998-03-11
KR19980701525A (ko)	1998-05-15
AP662A (en)	1998-08-19
BG63393B1 (bg)	2001-12-29
CN1049893C (zh)	2000-03-01
ZA96449B (en)	1996-08-07
FI973063A7 (fi)	1997-09-18
DE69635106D1 (de)	2005-09-29
FI973063L (fi)	1997-09-18
CN1179159A (zh)	1998-04-15
IL116831A (en)	1998-10-30
EE03528B1 (et)	2001-10-15
RS49518B (sr)	2006-10-27
NZ298851A (en)	1999-01-28
BR9606768A (pt)	1997-12-30
KR100376074B1 (ko)	2003-06-02
ES2248806T3 (es)	2006-03-16
HUP9801836A2 (hu)	1999-05-28
HRP960024A2 (en)	1997-10-31
BG101833A (bg)	1998-04-30
IS4527A (is)	1997-07-15
HRP960024B1 (en)	2005-08-31
ATE302777T1 (de)	2005-09-15
GB9501178D0 (en)	1995-03-08
AU4453996A (en)	1996-08-07
EP0804436B1 (fr)	2005-08-24
EA000364B1 (ru)	1999-06-24
HU222993B1 (hu)	2004-01-28
CZ297065B6 (cs)	2006-08-16
NO973326D0 (no)	1997-07-18
NO973326L (no)	1997-09-16
EP0804436A1 (fr)	1997-11-05
SK96597A3 (en)	1998-02-04
OA10499A (en)	2002-04-10
EA199700124A1 (ru)	1997-12-30
UA46001C2 (uk)	2002-05-15
US6107302A (en)	2000-08-22
FI973063A0 (fi)	1997-07-18

Legal Events

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2011-09-05	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO315558B1 (no)	2003-09-22	Vannfri krystallinsk form av valaciclovir-hydroklorid
KR100412298B1 (ko)	2004-04-21	콜로이드이산화규소를함유하는발라시클로비르정제
CA2243237C (fr)	2008-09-02	Utilisation de valaciclovir dans la fabrication d'un medicament destine au traitement de l'herpes genital
EP3749673B1 (fr)	2022-03-16	Form cristalline de sodium de bictegravir
PL194752B1 (pl)	2007-07-31	Krystaliczna postać VI 5,6-dichloro-2-(izopropyloamino)-1-(ß-L-rybofuranozylo)-1H-benzimidazolu, sposób jej wytwarzania, kompozycja farmaceutyczna zawierająca krystaliczną postać i zastosowanie krystalicznej postaci
MXPA97005462A (en)	1998-07-03	Derived from guan
EA020944B1 (ru)	2015-02-27	Кристаллическая форма i соли розувастатина цинка
HK1003055B (en)	2006-02-03	Guanine derivative
HK1063621B (en)	2009-04-24	Crystalline form of a phenylethanolamine, the preparation thereof and pharmaceutical compositions comprising the same
MXPA97005459A (en)	1998-07-03	Valaciclovir tablets containing silicon dioxide color
HK1063621A1 (zh)	2005-01-07	苯基乙醇胺的晶形，其製備方法和含有它的藥物組合物
CZ20003709A3 (cs)	2001-05-16	Nové krystalické formy protivirivé benzimidazolové sloučeniny