EA029018B1 - Фармацевтические составы нитазоксанида с контролируемым высвобождением - Google Patents
Фармацевтические составы нитазоксанида с контролируемым высвобождением Download PDFInfo
- Publication number
- EA029018B1 EA029018B1 EA201190127A EA201190127A EA029018B1 EA 029018 B1 EA029018 B1 EA 029018B1 EA 201190127 A EA201190127 A EA 201190127A EA 201190127 A EA201190127 A EA 201190127A EA 029018 B1 EA029018 B1 EA 029018B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- nitazoxanide
- polymorph
- amide
- ester
- salt
- Prior art date
Links
- YQNQNVDNTFHQSW-UHFFFAOYSA-N acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 YQNQNVDNTFHQSW-UHFFFAOYSA-N 0.000 title claims abstract description 98
- 229960002480 nitazoxanide Drugs 0.000 title claims abstract description 97
- 238000013270 controlled release Methods 0.000 title claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000012729 immediate-release (IR) formulation Substances 0.000 claims abstract description 31
- 239000011230 binding agent Substances 0.000 claims abstract description 29
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims abstract description 28
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims abstract description 28
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 208000005176 Hepatitis C Diseases 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract 56
- 150000002148 esters Chemical class 0.000 claims abstract 56
- -1 polymorph Chemical class 0.000 claims abstract 56
- 150000003839 salts Chemical class 0.000 claims abstract 56
- 238000000034 method Methods 0.000 claims abstract 30
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical group CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 claims abstract 18
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims abstract 8
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims abstract 8
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims abstract 8
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 claims description 32
- 239000000945 filler Substances 0.000 claims description 22
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000008187 granular material Substances 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 235000019359 magnesium stearate Nutrition 0.000 claims description 10
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 7
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 239000000375 suspending agent Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 229920002261 Corn starch Polymers 0.000 claims description 5
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 5
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 5
- 239000008120 corn starch Substances 0.000 claims description 5
- 229960001681 croscarmellose sodium Drugs 0.000 claims description 5
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 5
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 5
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 5
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 108010050904 Interferons Proteins 0.000 claims description 3
- 102000014150 Interferons Human genes 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- 229940079322 interferon Drugs 0.000 claims description 3
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
- 239000007909 solid dosage form Substances 0.000 claims 23
- 239000000314 lubricant Substances 0.000 claims 8
- 239000003085 diluting agent Substances 0.000 claims 6
- 239000003443 antiviral agent Substances 0.000 claims 2
- 239000007884 disintegrant Substances 0.000 claims 2
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- 150000002334 glycols Chemical class 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- 238000009472 formulation Methods 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract 2
- 239000006186 oral dosage form Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 64
- FDTZUTSGGSRHQF-UHFFFAOYSA-N Desacetyl-nitazoxanide Chemical compound OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 FDTZUTSGGSRHQF-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 11
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 10
- 230000002411 adverse Effects 0.000 description 8
- 238000002648 combination therapy Methods 0.000 description 7
- 239000008213 purified water Substances 0.000 description 7
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- 239000000902 placebo Substances 0.000 description 6
- 229940068196 placebo Drugs 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- 238000001035 drying Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
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- 210000002966 serum Anatomy 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
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- 208000004998 Abdominal Pain Diseases 0.000 description 3
- 208000006154 Chronic hepatitis C Diseases 0.000 description 3
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- 229940099112 cornstarch Drugs 0.000 description 3
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- 238000005469 granulation Methods 0.000 description 3
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- 208000010710 hepatitis C virus infection Diseases 0.000 description 3
- 230000008693 nausea Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 206010012735 Diarrhoea Diseases 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000009265 virologic response Effects 0.000 description 2
- 206010008796 Chromaturia Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 102000004855 Multi drug resistance-associated proteins Human genes 0.000 description 1
- 108090001099 Multi drug resistance-associated proteins Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- UJTOVSZPBVTOMC-QKZHPOIUSA-N Tizoxanide glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC=CC=C1C(=O)NC1=NC=C([N+]([O-])=O)S1 UJTOVSZPBVTOMC-QKZHPOIUSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002706 dry binder Substances 0.000 description 1
- 238000007908 dry granulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 206010016766 flatulence Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100001079 no serious adverse effect Toxicity 0.000 description 1
- 229960003930 peginterferon alfa-2a Drugs 0.000 description 1
- 108010092853 peginterferon alfa-2a Proteins 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
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- 238000005070 sampling Methods 0.000 description 1
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- 229940033134 talc Drugs 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
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- 238000005550 wet granulation Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2086—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat
- A61K9/209—Layered tablets, e.g. bilayer tablets; Tablets of the type inert core-active coat containing drug in at least two layers or in the core and in at least one outer layer
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
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- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
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- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
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- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
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- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
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- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4808—Preparations in capsules, e.g. of gelatin, of chocolate characterised by the form of the capsule or the structure of the filling; Capsules containing small tablets; Capsules with outer layer for immediate drug release
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20228509P | 2009-02-13 | 2009-02-13 | |
| PCT/US2010/024000 WO2010093854A1 (en) | 2009-02-13 | 2010-02-12 | Controlled release pharmaceutical formulations of nitazoxanide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201190127A1 EA201190127A1 (ru) | 2012-03-30 |
| EA029018B1 true EA029018B1 (ru) | 2018-01-31 |
Family
ID=42560126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201190127A EA029018B1 (ru) | 2009-02-13 | 2010-02-12 | Фармацевтические составы нитазоксанида с контролируемым высвобождением |
Country Status (23)
| Country | Link |
|---|---|
| US (5) | US8524278B2 (https=) |
| EP (1) | EP2395840B1 (https=) |
| JP (3) | JP5726766B2 (https=) |
| KR (1) | KR101697800B1 (https=) |
| CN (2) | CN102395276A (https=) |
| AU (3) | AU2010213678B2 (https=) |
| BR (1) | BRPI1007945C8 (https=) |
| CA (1) | CA2752233C (https=) |
| CO (1) | CO6501159A2 (https=) |
| CY (1) | CY1123162T1 (https=) |
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| US9498441B2 (en) | 2012-01-27 | 2016-11-22 | Siegfried Rhein S.A. De C.V. | Nitazoxadine composition and process to prepare same |
| WO2013124768A1 (en) * | 2012-02-20 | 2013-08-29 | Lupin Limited | Bilayer tablet of dronedarone |
| KR101639692B1 (ko) * | 2013-12-13 | 2016-07-14 | 제일약품주식회사 | 2 이상의 유효성분을 포함하는 구강 내 속붕해 다중유닛 약제학적 조성물 |
| CN107105660A (zh) | 2014-11-11 | 2017-08-29 | 罗马克实验室有限公司 | 使用替唑尼特、其类似物或盐的前药的治疗组合物和治疗方法 |
| CN108289961A (zh) | 2016-03-31 | 2018-07-17 | 罗马克实验室有限公司 | 用于治疗病毒性感染的噻唑化物化合物 |
| CN109152760B (zh) * | 2016-04-11 | 2022-09-23 | 基恩菲特公司 | 胆汁淤积性和纤维化疾病的治疗方法 |
| US10905680B2 (en) * | 2016-04-11 | 2021-02-02 | Genfit | Methods of treatment for cholestatic and fibrotic diseases |
| EA201992116A1 (ru) * | 2017-03-08 | 2020-01-29 | СИНРКС ФАРМА, ЭлЭлСи | Фармацевтические составы флороглюцинола и триметилфлороглюцинола |
| KR20190122806A (ko) * | 2017-03-13 | 2019-10-30 | 장피트 | 조합 치료요법용 약학 조성물 |
| US11173149B2 (en) | 2017-04-18 | 2021-11-16 | Romark Laboratories L.C. | Inhibition of protein disulfide-isomerase A3 |
| EP3639854B1 (en) | 2017-06-16 | 2026-01-07 | The Doshisha | Mtor-inhibitor-containing medicine for treating or preventing fuchs' endothelial corneal dystrophy |
| US20200121652A1 (en) * | 2017-06-16 | 2020-04-23 | The Doshisha | Compounds having caspase inhibitory activity, pharmaceutical agent containing said compounds and for treating or preventing corneal endothelial symptoms, disorders, or diseases, and application of said pharmaceutical agent |
| CN108524460B (zh) * | 2018-05-14 | 2021-01-01 | 佛山市南海东方澳龙制药有限公司 | 烯啶虫胺双层片 |
| WO2019241376A1 (en) | 2018-06-14 | 2019-12-19 | The Trustees Of Columbia University In The City Of New York | Treatment of cognitive disorders using nitazoxanide (ntz), nitazoxanide (ntz) analogs, and metabolites thereof |
| CN110025621A (zh) * | 2019-03-13 | 2019-07-19 | 中国农业科学院上海兽医研究所(中国动物卫生与流行病学中心上海分中心) | 替唑尼特和硝唑尼特在制备抗炎药物中的应用 |
| CN111012788B (zh) * | 2019-12-12 | 2021-01-15 | 武汉职业技术学院 | 硝唑尼特和替唑尼特在制备抗猪繁殖与呼吸综合征病毒药物中的应用 |
| JP2023510140A (ja) * | 2019-12-19 | 2023-03-13 | セルトリオン， インク． | シベンゾリンまたはその塩を含む薬学剤形 |
| EP4182304A1 (en) | 2020-07-20 | 2023-05-24 | Romark Laboratories, L.C. | Crystalline salts of tizoxanide and 2-hydroxy-n-(5-chloro-1,3-thiazol-2-yl)benzamide (rm-4848) with ethanolamine, morpholine, propanolamine, piperazine and n-methylpiperazine |
| MX2023002208A (es) | 2020-08-24 | 2023-05-17 | Romark Laboratories Lc | Uso de tiazolidas contra los coronavirus. |
| WO2022130406A1 (en) * | 2020-12-15 | 2022-06-23 | Cipla Limited | Inhalation composition of nitazoxanide or its derivatives for use in coronavirus disease |
| DE112022004799T5 (de) | 2021-10-05 | 2024-08-14 | Council Of Scientific And Industrial Research An Indian Registered Body Incorporated Under The Regn. Of Soc. Act (Act Xxi Of 1860) | Verbessertes Verfahren zur Herstellung von Nitazoxanid und Zwischenprodukten davon |
| CN114259492A (zh) * | 2021-12-21 | 2022-04-01 | 中以海德人工智能药物研发股份有限公司 | 硝唑尼特在治疗乙肝中的应用 |
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| US20070167504A1 (en) * | 2006-01-09 | 2007-07-19 | Jean-Francois Rossignol | Viral hepatitis treatment |
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