WO2018056865A1 - Composition pharmaceutique pour traiter une infection par le vih - Google Patents

Composition pharmaceutique pour traiter une infection par le vih Download PDF

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Publication number
WO2018056865A1
WO2018056865A1 PCT/RU2017/000622 RU2017000622W WO2018056865A1 WO 2018056865 A1 WO2018056865 A1 WO 2018056865A1 RU 2017000622 W RU2017000622 W RU 2017000622W WO 2018056865 A1 WO2018056865 A1 WO 2018056865A1
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
ritonavir
composition according
lopinavir
peg
Prior art date
Application number
PCT/RU2017/000622
Other languages
English (en)
Russian (ru)
Inventor
Елена Сергеевна ХАЗАНОВА
Сергей Юрьевич НОГАЙ
Дмитрий Владимирович ЯКОВЛЕВ
Original Assignee
Общество С Ограниченной Ответственностью Изварино Фарма
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.)
Filing date
Publication date
Application filed by Общество С Ограниченной Ответственностью Изварино Фарма filed Critical Общество С Ограниченной Ответственностью Изварино Фарма
Priority to CN201780057215.9A priority Critical patent/CN109789140A/zh
Publication of WO2018056865A1 publication Critical patent/WO2018056865A1/fr

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Classifications

    • 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
    • A61K31/41—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
    • 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
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • A61K9/10—Dispersions; Emulsions
    • 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
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • 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
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • 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
    • A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2121/00—Preparations for use in therapy

Definitions

  • composition for treating HIV infection comprises
  • the invention relates to the field of the pharmaceutical industry.
  • HIV protease (PI) inhibitors which include lopinavir and ritonavir, are substances with an affinity for the active site of the HIV protease, which should cleave the Gag-Pol virus polyprotein into individual functional proteins.
  • protease does not fulfill its function, and viral particles are formed that are not able to infect new cells.
  • PIs often have a side effect on the digestive tract. With prolonged use, lipid metabolism disorders of varying severity and the development of lipodystrophy are possible.
  • HIV protease inhibitors substances such as nelfinvavir, saquinavir, tipranavir, darunavir, indinavir, atazanavir, ritonavir, lopinavir, palinavir, fosamprenavir are known.
  • polymeric carrier compositions for the formation of solid dispersions are in demand, which exhibit a higher ability to dissolve the drug and / or make it possible to reduce the melt viscosity without compromising the mechanical properties and storage stability of the dosage form.
  • melt extrusion technology One way to improve the bioavailability of sparingly soluble substances is to use melt extrusion technology.
  • Mandatory steps of this technology are the melting or melting of a mixture of a polymer binder and an active pharmaceutical ingredient and, possibly, but not necessarily, additional excipients and the formation of an extrudate from the melt.
  • the labor is processed, in order to prepare for the formation of the finished dosage form, by any suitable methods.
  • a solid solution of active pharmaceutical ingredient in the matrix There are a number of difficulties in the selection of a suitable composition of excipients and technological parameters. Constant research is underway to develop new compositions suitable for solving the problem.
  • WO 01/00175 discloses mechanically stable pharmaceutical dosage forms that are solid solutions of the active ingredients in an auxiliary reagent matrix.
  • the matrix contains a homopolymer or copolymer of ⁇ -vinylpyrrolidone and a liquid or semi-liquid surfactant.
  • WO 00/57854 discloses mechanically stable pharmaceutical oral dosage forms which contain at least one active compound, at least one thermoplastic forming matrix forming adjuvant, and from more than 10% to 40% May.
  • a surfactant that has an HLB value (hydrophilic-lipophilic balance index) of 2 to 18 is liquid at 20 ° C or has a dropping point of 20 to 50 ° C.
  • BCS is a biopharmaceutical classification system.
  • Figure 1 The analysis of the degree of crystallinity of the pharmaceutical composition according to example 2 analyzed using small angle x-ray scattering - SAXS (Anton Paar). 1 - a mixture of polymers and APS (extrudate), 2 - lopinavir, 3 - a mixture of polymers included in the extrudate.
  • Figure 2 The analysis of the degree of crystallinity of the pharmaceutical composition according to example 2 analyzed using SAXS (Anton Paar). 1 - a mixture of polymers and APS after extrusion (extrudate) after 6 months of storage, 2 - lopinavir, 3 - a mixture of polymers after extrusion after 6 months of storage, 4 - ritonavir
  • Figure 3 The study of the kinetics of the release of lopinavir ( Figures ZA, V, D, G) and ritonavir ( Figures ST, G, E, 3) from the studied drug (PI) - Lopinavir and Ritonavir (solid line), tablets, film-coated from example 5, 7, 8 and 4, respectively, in comparison with the Comparative Preparation (PS) - Kaletra (dotted line).
  • the ordinate indicates the amount of substance transferred to the solution in%, and the abscissa indicates the time of sampling, min.
  • the objective of the invention is the development of alternative formulations and technologies for the production of the dosage form of the drug (HIV protease inhibitor), improving the pharmacokinetic parameters of the drug.
  • the content of copovidone in the finished dosage form should be from 5 to 65% by weight of the finished dosage form, and the matrix polymer PEG 6000 / vinylcaprolactam / vinyl acetate - from 5 to 55%.
  • the copovidone content of the finished dosage form should be from 45 to 65%, and PEG 6000 / vinylcaprolactam / vinyl acetate should be from 5 to 25%. In the case of a change in the content of these substances or the exclusion of one of the substances from the finished dosage form, it was not possible to improve the kinetics of dissolution of the active substances (see Figure ZD, E, G and 3).
  • the AUC of ritonavir was 5842.50
  • AUC of ritonavir was 6204.75
  • AUC of lopinavir was 5986.50
  • AUC of lopinavir was 6387.00 .
  • the differences in the numerical characteristics of almost 10% suggest the presence of the influence of the dissolution rate on the pharmacokinetic parameters.
  • PEG 6000 / vinylcaprolactam / vinyl acetate As the matrix polymer, PEG 6000 / vinylcaprolactam / vinyl acetate can be used.
  • the pharmaceutical composition may contain conventional excipients adopted in the preparation of medicines, such as binders, fillers, preservatives, flow regulators, emollients, wetting agents , dispersing agents, emulsifying agents, solvents, antioxidants and / or propellants, prolonging agents of action of Sucker et al .: Pharmazeutician Technologie, Thieme-Verlag, Stuttgard, 1991.
  • the pharmaceutical composition contains one or more of the following substances: sugars and their derivatives (lactose, modified lactose, sucrose, glucose, mannitol, modified mannitol, sorbitol, fructose), polysaccharides (cellulose and its derivatives, starch, modified starch, starch, dextrin, dextrose, dextrate, maltodextrin, calcium and its salts (phosphates, carbonates, chlorides), crospovidone, copovidones, cyclodextrins, alginic acid and its salts, saccharin and its salts, sodium and its salts (chloride, citrate, fumarate, carbonate), aspartame, lactic acid and its salts, succinic acid, ascorbic acid, tartaric acid, colloidal silicon dioxide.
  • sugars and their derivatives lactose, modified lactose, sucrose, glucose, mannitol, modified mannitol, sorbitol,
  • the pharmaceutical composition contains from 0.5 to 60 wt.% The above excipients (in terms of 100 wt.% Of the entire solid dosage form).
  • the finished dosage form may contain other pharmaceutically acceptable polymers that can be selected from the group consisting of water soluble polymers, water dispersible polymers and water swellable polymers and any mixtures thereof.
  • Polymers are considered water soluble if they form a clear, homogeneous solution in water. After dissolving at 20 ° C. in water at a concentration of 2% ( May / vol.),
  • the water-soluble polymer preferably has a viscosity of 1 to 5000 MPa-s, more preferably 1 to 700 MPa s and most preferably from 5 to 100 MPa s.
  • Water-dispersible polymers are those which, when reacted with water, form colloidal dispersions, rather than a clear solution. When interacting with water or aqueous solutions, water-swellable polymers usually form a rubbery gel.
  • preferred pharmaceutically acceptable polymers can be selected from the group consisting of water soluble polymers suitable for use in the pharmaceutical composition of the present invention, including but not limited to the following materials: ⁇ -vinyl lactam homopolymers and copolymers, especially homopolymers and copolymers of ⁇ -vinylpyrrolidone, for example polyvinylpyrrolidone (PVP), copolymers of ⁇ -vinylpyrrolidone and vinyl acetate or vinyl propionate; high molecular weight polyalkylene oxides such as polyethylene oxide and polypropylene oxide and copolymers of ethylene oxide and propylene oxide; by- lyacrylates and polymethacrylates such as methacrylic acid / ethyl acrylate copolymers, methacrylic acid / methyl methacrylate copolymers, butyl methacrylate / 2-dimethylaminoethyl methacrylate copolymers, poly (hydroxyalkyl acrylates, poly
  • Water-insoluble polymers that may be used in the present invention include, but are not limited to, the following materials: microcrystalline cellulose, low-substituted hyprolose (hydroxypropyl cellulose).
  • the pharmaceutical composition contains from 10 to 70.0 wt.% Polymer (in terms of 100 wt.% Of the entire solid dosage form).
  • Surfactants suitable for use in the pharmaceutical composition of the present invention include, but are not limited to the following substances: polysorbate 80 (e.g., TWIN-80 polysorbate), macrogol 6000 (polyethylene glycol 6000), sorbitan fatty acid monoesters, such as Span® 20, Span® 40 and Span® 60; or mixtures of one or more of them; polyoxyethylene derivatives of castor oil, for example polyoxyethylene glycerol triticinoleate or polyoxyl 35 castor oil (Cremophor® EL; BASF Corp.), or polyoxy ethylene glycerol oxystearate such as polyethylene glycol 40 hydrogenated castor oil (Cremophor® RH 40) or polyethylene glycol 60 oil (Cremophor® RH 60); alpha-tocopheryl polyethylene glycol succinate, which is usually abbreviated as Vitamin E GSH C; as well as polyalkoxylated glycerides sold by Gattefosse under the trade names Gelucire
  • the pharmaceutical composition contains from 0.3 to 10.0 wt.% Surfactants (in terms of 100 wt.% Of the entire solid dosage form).
  • the finished dosage form may further include one or more lubricants and glidants, which may include stearic acid and its derivatives or esters, such as: sodium stearate, magnesium stearate, calcium stearate and the corresponding esters, such as : sodium fumarate stearyl; talc and silicon dioxide, respectively, but are not limited to.
  • the amount of lubricant and / or glidant is preferably in the range from 0.25% to 5% by weight of the composition.
  • the drug can be made in in the form of powders, tablets, combination tablets, capsules, dragees, coated granules, suppository, powders for the preparation of suspensions.
  • Dosage forms can be performed in the traditional way ("Pharmaceutical technology. Technology of dosage forms", 2nd ed., Moscow, 2006).
  • the pharmaceutical composition of the invention may be administered orally. Dosage depends on the age, condition and weight of the patient.
  • melt temperature is in the range of from about 40 ° C to about 200 ° C, preferably from about 50 ° C to about 160 ° C.
  • the mixing of the components and the preparation of the moldable mass can be carried out in different ways. Mixing can be carried out before, during and / or after heating of some or all of the components of the mass. For example, in order to obtain a moldable mass, the respective components may first be mixed and then heated. In addition, they can be mixed and heated at the same time. Often, additional homogenization of the moldable mass is carried out to provide a highly dispersed distribution of the biologically active substance.
  • Heating is carried out in devices commonly used for this purpose.
  • heated extruders or mixers in particular continuous mixers (for example, such as ORP, CRP, AP or DTB from List, type Reaktotherm from Krauss-Maffei or Baker-Perkins worm mixers from Buss), two-blade two-tray mixers (trough mixers), plunger (internal) mixers or rotor / stator systems (e.g. PSA Dispax).
  • continuous mixers for example, such as ORP, CRP, AP or DTB from List, type Reaktotherm from Krauss-Maffei or Baker-Perkins worm mixers from Buss
  • two-blade two-tray mixers trough mixers
  • plunger (internal) mixers or rotor / stator systems e.g. PSA Dispax.
  • extruders single-screw extruders, comb screw extruders, as well as multi-screw, in particular double-screw extruders, if necessary equipped with kneading disks, with unidirectional or multidirectional rotation of the worms, can be used.
  • Werner u twin screw extruders are particularly preferred.
  • the mass in the extruders or mixers is loaded in the usual way continuously or periodically.
  • Powdered components can be loaded by gravity, for example, using differential metering weights.
  • Plastic masses can be fed directly from the extruder or by means of a gear pump, the use of which is preferred in case of high viscosity and pressure.
  • Liquid media can be dosed with a suitable pump.
  • the resulting masses have a pasty or pasty consistency. They are usually subjected to molding. In this case, depending on the type of forming tool and the molding method, the most diverse form can be given to the molded masses.
  • the extruded strand can be molded between one tape and one roll, between two tapes or two rolls, as described in European patent application EP-A-358105, or by processing on a calender equipped with two forming rolls - mi (see, for example, European patent application EP-A-240904).
  • By extrusion and hot or cold cutting of an extruded tow for example, fine granules can be obtained.
  • the cooled mass may be milled to a powder state and subsequently conventionally compressed to form tablets.
  • auxiliary substances intended for tabletting can be used.
  • the resulting mixture was extruded at a temperature of 105 to 145 ° C, dusted, and tabletted.
  • the resulting mixture is extruded at a temperature of 135 ° C, powder, tablet to tiroat.
  • the resulting mixture is extruded at a temperature of 120 ° C, dusted, tableted.
  • SAXS SAXSpace - Small Angle X-ray Scattering

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne le domaine de l'industrie chimico-pharmaceutique. La composition pharmaceutique pour traiter une infection par le VIH comprend le Lopinavir et le Ritonavir en quantités suffisantes ainsi qu'un polymère. La composition chimique est obtenue par extrusion. La composition utilise en tant que polymère un matériau constitué de polyéthylène glycol 6000, caprolactame de vinyle / acétate de vinyle de 5 à 25 % de la masse de composition pharmaceutique en combinaison avec le Copovidon dans des proportions de 45 à 65 % du poids de la composition pharmaceutique. L'invention permet d'élargir la gamme de moyens médicamenteux possédant des propriétés pharmacocinétiques améliorées.
PCT/RU2017/000622 2016-09-21 2017-08-25 Composition pharmaceutique pour traiter une infection par le vih WO2018056865A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201780057215.9A CN109789140A (zh) 2016-09-21 2017-08-25 用于治疗hiv感染的药物组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
RU2016137670 2016-09-21
RU2016137670A RU2619840C1 (ru) 2016-09-21 2016-09-21 Фармацевтическая композиция для лечения ВИЧ-инфекции

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WO2018056865A1 true WO2018056865A1 (fr) 2018-03-29

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WO (1) WO2018056865A1 (fr)

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Publication number Priority date Publication date Assignee Title
CN112263554B (zh) * 2020-10-22 2022-09-30 安徽贝克生物制药有限公司 一种洛匹那韦利托那韦复方片剂及其制备方法

Citations (3)

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Publication number Priority date Publication date Assignee Title
EA011924B1 (ru) * 2003-08-28 2009-06-30 Эбботт Лэборетриз Твердая фармацевтическая дозированная форма
US20130190337A1 (en) * 2010-08-02 2013-07-25 Ranbaxy Laboratories Limited Solid dosage forms of hiv protease inhibitors
US20160193151A1 (en) * 2015-01-06 2016-07-07 Maria Del Pilar Noriega Escobar Dosage form incorporating an amorphous drug solid solution

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DE19913692A1 (de) * 1999-03-25 2000-09-28 Basf Ag Mechanisch stabile pharmazeutische Darreichungsformen, enthaltend flüssige oder halbfeste oberflächenaktive Substanzen
DE19929361A1 (de) * 1999-06-25 2001-01-04 Basf Ag Mechanisch stabile pharmazeutische Darreichungsformen, enthaltend flüssige oder halbfeste oberflächenaktive Substanzen
US8377952B2 (en) * 2003-08-28 2013-02-19 Abbott Laboratories Solid pharmaceutical dosage formulation
DE102005053066A1 (de) * 2005-11-04 2007-05-10 Basf Ag Verwendung von Copolymeren als Solubilisatoren für in Wasser schwerlöslichen Verbindungen
EP1880715A1 (fr) * 2006-07-19 2008-01-23 Abbott GmbH & Co. KG Composition de solubilisation acceptable sur le plan pharmaceutique et forme posologique contenant celle-ci
US9594073B2 (en) * 2010-02-18 2017-03-14 Abbvie Deutschland Gmbh & Co Kg Test solvent for evaluating the compatibility of biologically active substances and graft copolymers
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Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
EA011924B1 (ru) * 2003-08-28 2009-06-30 Эбботт Лэборетриз Твердая фармацевтическая дозированная форма
US20130190337A1 (en) * 2010-08-02 2013-07-25 Ranbaxy Laboratories Limited Solid dosage forms of hiv protease inhibitors
US20160193151A1 (en) * 2015-01-06 2016-07-07 Maria Del Pilar Noriega Escobar Dosage form incorporating an amorphous drug solid solution

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CN109789140A (zh) 2019-05-21

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