HRP20220046T1 - Priprema čvrstih kompleksa ciklodekstrina za uporabu oftalmološki aktivnih farmaceutskih sastojka - Google Patents

Priprema čvrstih kompleksa ciklodekstrina za uporabu oftalmološki aktivnih farmaceutskih sastojka Download PDF

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HRP20220046T1
HRP20220046T1 HRP20220046TT HRP20220046T HRP20220046T1 HR P20220046 T1 HRP20220046 T1 HR P20220046T1 HR P20220046T T HRP20220046T T HR P20220046TT HR P20220046 T HRP20220046 T HR P20220046T HR P20220046 T1 HRP20220046 T1 HR P20220046T1
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dexamethasone
cyclodextrin
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Thorsteinn Loftsson
Zoltan FULOP
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Oculis SA
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    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • 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
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    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • 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
    • A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • 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
    • A61K9/08—Solutions
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof

Claims (15)

1. Oftalmološki pripravak koji sadrži, u oftalmološki prihvatljivom mediju: čvrsti kompleks koji sadrži deksametazon i γ-ciklodekstrin, pri čemu pripravak sadrži bilo (i) manje od 1%, posebno manje od 0.8% mase bilo kojeg proizvoda koji nije dobrovoljno uveden u pripravak iz navedenog, ali je nastao in situ tijekom proizvodnje pripravka, na temelju težine deksametazona, ili, (ii) manje od 0.5%, posebno manje od 0.3%, točnije manje od 0.2% mase deksametazon enol aldehida na temelju težine deksametazona.
2. Oftalmološki pripravak prema zahtjevu 1, naznačen time što pripravak nadalje sadrži polimer, na primjer poloksamer.
3. Oftalmološki pripravak prema zahtjevu 2, u kojem je količina polimera 0.5 do 5%, posebno 1 do 4%, točnije 2 do 3%, točnije 2.2 do 2.8%, mase polimera na temelju volumena pripravka.
4. Oftalmološki pripravak prema zahtjevu 3, naznačen time što je viskoznost pripravka od 4 do 14 cP, poželjno 5 do 13 cP, poželjnije 6 do 12 cP.
5. Oftalmološki pripravak prema bilo kojem od zahtjeva 1 do 4, u kojem je deksametazon prisutan u pripravku u koncentraciji od 10 mg/mL do 20 mg/mL.
6. Oftalmološki pripravak prema bilo kojem od zahtjeva 1 do 5, u kojem je 60 do 95% mase, posebno 70 do 90% mase deksametazona u pripravku u obliku čvrstog kompleksa deksametazona i γ-ciklodekstrina.
7. Oftalmološki pripravak prema bilo kojem od zahtjeva 1 do 6, naznačen time što je količina γ-ciklodekstrina od 1 do 25%, posebno 5 do 20%, točnije 10 do 18%, još preciznije 12 do 16%, mase γ-ciklodekstrina na temelju volumena pripravka.
8. Oftalmološki pripravak prema bilo kojem od zahtjeva 1 do 7, naznačen time što pripravak sadrži: - 1 do 2% deksametazona, na primjer 1.5% deksametazona; - 12 do 16% γ-ciklodekstrina, na primjer 14% γ-ciklodekstrina; - 2.2 do 2.8% polimera, na primjer 2.5% poloksamera; - 0 do 0.2% stabilizirajućeg sredstva, na primjer 0.1% dinatrijevog edetata; - 0 do 1% elektrolita, na primjer 0.57% natrijevog klorida; i - vodu; pri čemu % su % mase na temelju volumena pripravka.
9. Postupak za pripremu oftalmološkog pripravka, koji sadrži korake: a) suspendiranje deksametazona u oftalmološki prihvatljivom mediju da se dobije suspenzija i zagrijavanje navedene suspenzije sve dok se deksametazon znatno ne otopi u oftalmološki prihvatljivom mediju; b) suspendiranje γ-ciklodekstrina u oftalmološki prihvatljivom mediju da se dobije suspenzija i zagrijavanje navedene suspenzije sve dok se γ-ciklodekstrin znatno ne otopi u oftalmološki prihvatljivom mediju; c) miješanje pripravka iz koraka a) i b) na temperaturi Tl nižoj od 120°C i zagrijavanje mješavine na temperaturi T1 nižoj od 120°C tijekom vremena t; i d) hlađenje rezultirajuće otopine na temperaturu T2 da se dobije oftalmološki pripravak koji sadrži čvrsti kompleks deksametazona i γ-ciklodekstrina.
10. Postupak prema zahtjevu 9, naznačen time što je temperatura T1 80 do 110°C, posebno 80 do 105°C, točnije 80 do 100°C.
11. Postupak prema zahtjevu 9 ili 10, naznačen time što je temperatura T2 10 do 40°C, posebno 15 do 35°C, točnije 20 do 30°C.
12. Postupak prema bilo kojem od zahtjeva 9 do 11, naznačen time što se temperatura T1 hladi na temperaturu T2 brzinom od 1 do 25°C/min, posebno 2 do 20°C/min, točnije 5 do 18°C/ min.
13. Oftalmološki pripravak koji se može dobiti postupkom prema bilo kojem od zahtjeva 9 do 12, naznačen time što oftalmološki pripravak sadrži bilo (i) manje od 1%, točnije manje od 0.8% mase bilo kojeg proizvoda koji nije dobrovoljno uveden u pripravak iz navedenog, ali je nastao in situ tijekom proizvodnje pripravka na temelju težine deksametazona, ili, (ii) manje od 0.5 %, posebno manje od 0.3 %, točnije manje od 0.2 % mase deksametazon enol aldehida na temelju težine deksametazona.
14. Oftalmološki pripravak prema bilo kojem od zahtjeva 1 do 8 i 13, za uporabu u liječenju očnog stanja, posebno prednjeg ili stražnjeg očnog stanja, točnije uveitisa i makularnog edema.
15. Oftalmološki pripravak za uporabu prema zahtjevu 14, naznačen time što se pripravak koristi kao kapi za oči.
HRP20220046TT 2016-11-29 2017-11-29 Priprema čvrstih kompleksa ciklodekstrina za uporabu oftalmološki aktivnih farmaceutskih sastojka HRP20220046T1 (hr)

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Application Number Priority Date Filing Date Title
US201662427737P 2016-11-29 2016-11-29
PCT/IB2017/001659 WO2018100434A1 (en) 2016-11-29 2017-11-29 Preparation of solid cyclodextrin complexes for ophthalmic active pharmaceutical ingredient delivery
EP17851871.8A EP3548091B1 (en) 2016-11-29 2017-11-29 Preparation of solid cyclodextrin complexes for ophthalmic active pharmaceutical ingredient delivery

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HRP20220046T1 true HRP20220046T1 (hr) 2022-04-15

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US (6) US20190343846A1 (hr)
EP (2) EP3548091B1 (hr)
JP (2) JP7138103B2 (hr)
KR (3) KR20240036731A (hr)
CN (2) CN110177576B (hr)
AR (2) AR110270A1 (hr)
AU (1) AU2017369971B2 (hr)
BR (1) BR112019011067A2 (hr)
CA (1) CA3045226A1 (hr)
CL (1) CL2019001447A1 (hr)
CO (1) CO2019005729A2 (hr)
CY (1) CY1124917T1 (hr)
DK (1) DK3548091T3 (hr)
EA (1) EA201991299A1 (hr)
ES (1) ES2903383T3 (hr)
HR (1) HRP20220046T1 (hr)
HU (1) HUE057221T2 (hr)
IL (2) IL266964B1 (hr)
LT (1) LT3548091T (hr)
MA (1) MA46997B1 (hr)
MD (1) MD3548091T2 (hr)
MX (1) MX2019006221A (hr)
PH (1) PH12019550088A1 (hr)
PL (1) PL3548091T3 (hr)
PT (1) PT3548091T (hr)
RS (1) RS62845B1 (hr)
SI (1) SI3548091T1 (hr)
TW (2) TWI773706B (hr)
UA (1) UA124774C2 (hr)
WO (1) WO2018100434A1 (hr)
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EP4171507A1 (en) * 2020-06-30 2023-05-03 Oculis SA Preparation of solid cyclodextrin complexes for ophthalmic active pharmaceutical ingredient delivery
CN111728953B (zh) * 2020-07-29 2023-08-08 中国科学院上海药物研究所 一种托法替布或其盐的缓释制剂及其制备方法
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US20220233564A1 (en) * 2021-01-25 2022-07-28 University Of South Florida Ophthalmological formulations for the prevention of a coronavirus infection
WO2023132947A1 (en) * 2022-01-05 2023-07-13 The Regents Of The University Of California Closo-dodecaiododecaborate complexes and methods of use for same
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