ES2564419T3 - Composiciones de poliuretano hidrófilo - Google Patents

Composiciones de poliuretano hidrófilo Download PDF

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Publication number
ES2564419T3
ES2564419T3 ES07733393.8T ES07733393T ES2564419T3 ES 2564419 T3 ES2564419 T3 ES 2564419T3 ES 07733393 T ES07733393 T ES 07733393T ES 2564419 T3 ES2564419 T3 ES 2564419T3
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Prior art keywords
polymer
swelling
polymers
fluconazole
respect
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Jukka Tuominen
Amaia Zurutuza
Mark Livingston
Janet A. Halliday
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Ferring BV
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Ferring BV
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    • 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
    • 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
    • A61K31/4196—1,2,4-Triazoles
    • 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
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • 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
    • A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • A61K9/0036—Devices retained in the vagina or cervix for a prolonged period, e.g. intravaginal rings, medicated tampons, medicated diaphragms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Reproductive Health (AREA)
  • Engineering & Computer Science (AREA)
  • Urology & Nephrology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Biomedical Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Inorganic Chemistry (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Una composición farmacéutica de liberación controlada en forma de dosificación sólida que comprende (i) un polímero lineal apto para hinchamiento en agua que se puede obtener haciendo reaccionar juntos (a) un óxido de polietileno de peso molecular medio menor o igual a 4000; (b) un diol C5 a C20 alifático; y (c) un isocianato difuncional, en el que la relación de los componentes (a) con respecto a (b) con respecto a (c) está dentro del intervalo 0,01-0,1 a 1 a 1,01-1,1 en términos de pesos equivalentes; junto con (ii) un agente farmacéuticamente activo.

Description

imagen1
imagen2
imagen3
imagen4
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imagen6
Ejemplo 7. Capacidad de hinchamiento de polímeros en diferentes disolventes
Las determinaciones de hinchamiento para un número de polímeros seleccionados se llevaron a cabo en agua, etanol, alcohol isopropílico (IPA) y una mezcla al 50 % de IPA/agua con el fin de medir la cantidad de disolvente absorbido por el polímero. Los resultados se calcularon en base al hinchamiento medio de 5-10 muestras de ensayo y se muestran en la Tabla 3. La fórmula usada para los cálculos se muestra a continuación:
imagen7
Tabla 3. Porcentaje de hinchamiento de polímeros seleccionados en diferentes medios de hinchamiento (agua, etanol, IPA e IPA/agua al 50 %)
Nombre de
% de Hinchamiento en % de Hinchamiento % de Hinchamiento % de Hinchamiento
Polímero
Agua en Etanol en IPA en IPA/Agua al 50 %
Polímero A
81 190 15 300
Polímero E
41 80 18 115
Polímero J
10 - - -
Polímero K
5,6 - - -
Polímero P*3
1,5 - - -
10 Ejemplo 8. Ensayo de dureza Shore
Los polímeros fabricados se sometieron a ensayo en cuanto a la dureza Shore usando durómetros A y D. Estas mediciones se conocen bien por parte del experto en la técnica. Los resultados se presentan como la media de cuatro mediciones y se presentan en la Tabla 4.
Tabla 4. Valores de dureza Shore determinada para los polímeros fabricados
Nombre de Polímero
Durómetro A Durómetro D
Dureza Máxima Deformación permanente por fatiga(15 segundos)
Dureza Máxima Deformación permanente por fatiga(15 segundos)
Polímero A
95,3 0,8 59,3 5,3
Polímero B
98,0 0,0 60,6 4,1
Polímero C
97,5 0,5 53,1 2,1
Polímero D
96,0 0,0 50,5 4,3
Polímero E
98,0 0,0 67,0 6,5
Polímero F
94,5 0,0 53,5 3,3
Polímero G
97,5 0,0 65,8 6,0
Polímero H
N/A N/A N/A N/A
Polímero I
96,5 1,0 53,8 0,8
Polímero J
93,0 1,5 55,8 2,3
Polímero K
99,0 0,0 63,0 3,6
Polímero L
99,0 0,0 66,0 4,8
Polímero M
99,0 0,0 68,4 4,9
Polímero N
99,5 0,0 77,8 4,9
Polímero O
99,0 0,0 70,6 2,9
Polímero P
100,0 0,0 67,8 3,8
Condiciones experimentales: Temperatura 21 ºC Humedad relativa % HR 39
8 5
10
15
20
Ejemplo 9. Películas poliméricas fabricadas por medio de moldeo por compresión
Un número de polímeros seleccionados y una formulación polimérica cargada de fármaco de la Tabla 1 se secaron durante la noche a vacío antes del procesado. Las temperaturas de placa superior e inferior de la máquina de moldeo por compresión se ajustaron a la temperatura de procesado objetivo. Se colocaron dos láminas de Teflon entre el molde y las placas calientes. El tiempo de fusión fue de 3-5 minutos seguido de un tiempo de retención de 30-120 segundos a presión (170-200 bar). Se usó una cantidad predeterminada de polímero para llenar el molde. Tras el enfriamiento hasta temperatura ambiente las muestras (dispositivos de óvulo vaginal con dimensiones de 30 mm x 10 mm x 1 mm) se empujaron mecánicamente hacia afuera y se mantuvieron en el congelador para análisis posterior. Las condiciones de procesado se muestran en la Tabla 5.
Tabla 5. Procesado térmico de polímeros fabricados usando moldeo por compresión.
Polímero
Fluconazol (% Temperatura Presión de Tiempo de Tiempo de Espesor de
en peso)
(ºC) Cilindro (Bar) Fusión (s) Presión (s) Molde (mm)
Polímero
- 150 200 180 60 0,4
A
Polímero
- 160 170 180 30 1,0
B
Polímero
- 160 200 240 120 1,0
B
Polímero
- 190 200 180 20 0,4
C
Polímero
- 200 200 180 60 0,4
C
Polímero
- 180 200 300 60 0,4
D
Polímero
- 200 200 180 50 0,4
D
Polímero
- 165 200 270 60 0,4
E
Polímero
20 160 200 270 60 1,0
E
Polímero
- 170 200 210 60 0,4
E
Polímero
- 160 170 180 30 1,0
H
Polímero
- 200 200 180 50 0,4
P

Ejemplo 10. Carga de fármaco -extrusión
Los polímeros seleccionados se cargaron con el fluconazol de fármaco modelo. Se usó un extrusor de laboratorio de husillo gemelar en co-rotación de 16 mm para la carga de los polímeros. La Tabla 6 muestra las condiciones de carga de fármaco.
Tabla 6. Condiciones de carga por extrusión usadas en los dispositivos cargados con fluconazol
Polímero
Fármaco Fármaco (% enpeso) Velocidad de husillo (rpm) Perfil de temperatura desde la alimentación hasta la boquilla (ºC)
Polímero A
Fluconazol 20 30 96-150-150-150-155
Polímero E
Fluconazol 20 30 95-135-135-135-135
Ejemplo 11. Estudios de liberación de fármaco
La cantidad de fluconazol liberado a partir de los polímeros cargados por extrusión se investigó por medio de un procedimiento de solución basado en el procedimiento de paletas USP. Esta técnica está formada por un sistema de solución UV automatizado en el que se conecta una paleta de solución Distek (modelo 2100C) (velocidad de 50 rpm) a un espectrofotómetro Unicam UV 500 por medio de una bomba peristáltica Icalis. El sistema se opera usando un soporte lógico Dsolve.
9
Condiciones experimentales:
Temperatura 37 ºC
Medio de solución 500 ml de agua desgasificada y desionizada
Los perfiles de liberación de fármaco in vitro de los polímeros cargados por extrusión se compararon con los
5 polímeros lineales de hinchamiento elevado y los reticulados cargados por difusión, véase Figura 2. Los polímeros A y E cargados por extrusión se representaron con otro polímero lineal de hinchamiento elevado cargado por extrusión de la patente WO2004029125 (fluconazol al 20 % en peso de % SW elevado). El polímero reticulado cargado por difusión de la patente EP0016652/EP0016654 (fluconazol al 17 % en peso reticulado) también se muestra en el gráfico siguiente con otro polímero lineal de hinchamiento elevado cargado por difusión de la patente
10 WO2004029125 (fluconazol al 17 % en peso de % de SW elevado).
10

Claims (1)

  1. imagen1
ES07733393.8T 2006-07-05 2007-06-27 Composiciones de poliuretano hidrófilo Active ES2564419T3 (es)

Applications Claiming Priority (3)

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GB0613333 2006-07-05
GBGB0613333.4A GB0613333D0 (en) 2006-07-05 2006-07-05 Hydrophilic polyurethane compositions
PCT/GB2007/002401 WO2008003932A1 (en) 2006-07-05 2007-06-27 Hydrophilic polyurethane compositions

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ES2564419T3 true ES2564419T3 (es) 2016-03-22

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US (2) US8974813B2 (es)
EP (2) EP2966104B1 (es)
JP (1) JP5394237B2 (es)
CN (1) CN101484493B (es)
AU (1) AU2007271000B2 (es)
BR (1) BRPI0713630B1 (es)
CA (1) CA2656489C (es)
ES (2) ES2707749T3 (es)
GB (1) GB0613333D0 (es)
HK (1) HK1220220A1 (es)
PL (1) PL2966104T3 (es)
TR (1) TR201900597T4 (es)
WO (1) WO2008003932A1 (es)

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