ES2626648T3 - Composición farmacéutica que comprende sal L-hemitartrato de levalbuterol como formulación en aerosol - Google Patents

Composición farmacéutica que comprende sal L-hemitartrato de levalbuterol como formulación en aerosol Download PDF

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Publication number
ES2626648T3
ES2626648T3 ES10176026.2T ES10176026T ES2626648T3 ES 2626648 T3 ES2626648 T3 ES 2626648T3 ES 10176026 T ES10176026 T ES 10176026T ES 2626648 T3 ES2626648 T3 ES 2626648T3
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levalbuterol
mcg
aerosol formulation
average
pharmaceutical composition
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Paul Mcglynn
Roger Bakale
Craig Sturge
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Sunovion Pharmaceuticals Inc
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Sunovion Pharmaceuticals Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C07C215/60—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
    • 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
    • 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
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/0001—Details of inhalators; Constructional features thereof
    • A61M15/002—Details of inhalators; Constructional features thereof with air flow regulating means
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/009—Inhalators using medicine packages with incorporated spraying means, e.g. aerosol cans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/235—Saturated compounds containing more than one carboxyl group
    • C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
    • C07C59/255—Tartaric acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M2202/00—Special media to be introduced, removed or treated
    • A61M2202/04—Liquids
    • A61M2202/0468—Liquids non-physiological
    • A61M2202/0484—Alcohol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M2202/00—Special media to be introduced, removed or treated
    • A61M2202/04—Liquids
    • A61M2202/0468—Liquids non-physiological
    • A61M2202/0488—Surfactant, e.g. for the lung
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M2202/00—Special media to be introduced, removed or treated
    • A61M2202/06—Solids
    • A61M2202/064—Powder
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Hematology (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Otolaryngology (AREA)
  • Dispersion Chemistry (AREA)
  • Materials Engineering (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
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Abstract

Una composición farmacéutica que comprende L-hemitartrato de levalbuterol y un vehículo farmacéuticamente aceptable, donde la composición es una formulación de un aerosol adaptada para su administración usando un inhalador de dosis medidas, comprendiendo la formulación del aerosol L-hemitartrato de levalbuterol en forma cristalina y un agente propulsor.

Description

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La válvula se engarza en su sitio con un engastador de apriete. Se rellena luego a presión, a través de la válvula, HFA 134a (por ejemplo, 14,28 gramos por bote) usando un cargador de pistón positivo con un adaptador adecuado. Se almacena todas las unidades (orientadas con las válvulas abajo) durante tres días, seguido de una comprobación del peso para retirar las unidades con grandes fugas.
5 El bote se carga en un dispositivo estándar que acciona el inhalador de dosis medidas que se puede conseguir de Bespak Europe, King´s Lynn, Norfolk, PE30 2JJ, Reino Unido, que tiene una abertura con un diámetro en el intervalo de 0,30 a 0,36 mm.
Estudio de estabilidad
Se ha realizado un estudio de estabilidad sobre cargas de productos de 45 µg y 90 µg por actuación, preparados 10 como se describió anteriormente. Los resultados son como sigue: 25ºC/60% HR, orientación de la válvula arriba 25ºC/60% HR, orientación de la válvula abajo 40ºC/75% HR, orientación de la válvula arriba 40ºC/75% HR, orientación de la válvula abajo 15 Los resultados están tabulados a continuación. 25/60 válvula arriba
ENSAYO
INICIAL 1 MES 3 MESES 6 MESES
Tamaño de partícula – Impactador de cascada Andersen MMAD (µm) (promedio)
1,9 2,0 2,0 1,9
Tamaño de partícula – Impactador de cascada Andersen GSD (promedio)
1,7 1,7 1,7 1,6
Tamaño de partícula – Impactador de cascada Andersen fpf (promedio)
31,6% 34,5% 32,5% 34,1%
Promedio de uniformidad de la dosis emitida (RSD)
41,1 mcg (5,0%) 42,0 mcg (2,7%) 146,1 mcg (3,1%) 145,9 mcg (2,3%)
25/60 válvula abajo
ENSAYO
INICIAL 1 MES 3 MESES 6 MESES
Tamaño de partícula – Impactador de cascada Andersen MMAD (µm) (promedio)
1,9 1,9 2,0 1.8
Tamaño de partícula – Impactador de cascada Andersen GSD (promedio)
1,7 1,7 1,7 1,5
Tamaño de partícula – Impactador de cascada Andersen fpf (promedio)
31,6% 32,9% 32,9% 34,6%
Promedio de uniformidad de la dosis emitida (RSD)
41,1 mcg (5,0%) 42,2 mcg (4,7%) 146,8 mcg (3,5%) 147,1 mcg (3,5%)
40/75 válvula arriba
ENSAYO
INICIAL 1 MES 3 MESES 6 MESES
Tamaño de partícula – Impactador de cascada Andersen MMAD (µm) (promedio)
1,9 2,0 2,0 1,9
Tamaño de partícula – Impactador de cascada Andersen GSD (promedio)
1,7 1,8 1,7 1,6
7
ENSAYO
INICIAL 1 MES 3 MESES 6 MESES
Tamaño de partícula – Impactador de cascada Andersen fpf (promedio)
31,6% 31,6% 32,8% 34,3%
Promedio de uniformidad de la dosis emitida (RSD)
41,1 mcg (5,0%) 41,9 mcg (3,4%) 147,3 mcg (3,3%) 148,1 mcg (3,3%)
40/75 válvula abajo
ENSAYO
INICIAL 1 MES 3 MESES 6 MESES
Tamaño de partícula – Impactador de cascada Andersen MMAD (µm) (promedio)
1,9 2,1 2,1 2,0
Tamaño de partícula – Impactador de cascada Andersen GSD (promedio)
1,7 1,8 1,6 1,6
Tamaño de partícula – Impactador de cascada Andersen fpf (promedio)
31,6% 31,6% 33,5% 33,7%
Promedio de uniformidad de la dosis emitida (RSD)
41,1 mcg (5,0%) 40,5 mcg (3,2%) 148,0 mcg (3,3%) 151,0 mcg (2,4%)
1. Nota importante: el conjunto de datos a los 3 meses incluyen un cambio de método que mejoró la eficacia de la recopilación.
Definiciones de tamaño de partícula
5 Diámetro aerodinámico – El diámetro de una esfera de densidad unidad, que tiene la misma velocidad de sedimentación que la partícula en cuestión. Se usa para predecir dónde se depositarán tales partículas en el tracto respiratorio.
Diámetro aerodinámico (equivalente) -diámetro de una esfera de densidad unidad que tiene la misma velocidad de sedimentación-gravitacional que la partícula en cuestión. Un diámetro aerodinámico tiene en cuanta la forma, la
10 rugosidad, y el arrastre aerodinámico de la partícula. Usado para el movimiento de partículas a través de un gas.
Impactador de cascada – un dispositivo que usa una serie de etapas de impacto con tamaño de corte de partículas decreciente, de forma que las partículas se pueden separa en intervalos relativamente estrechos de diámetro aerodinámico; usado para medir la distribución de tamaño aerodinámico de un aerosol.
Desviación estándar geométrica – (GSD) -Una medida de la dispersión en una distribución logarítmica normal 15 (siempre superior o igual a 1,0).
Diámetro aerodinámico mediano másico – (MMAD) -El diámetro aerodinámico medio geométrico. El cincuenta por ciento en peso de las partículas será inferior al MMAD, el 50% será mayor.
Fracción de partículas finas – (fpf) – una proporción de la dosis emitida recogida en las etapas 3 para el filtro de un impactador de cascada Andersen.
20 Desviación estándar relativa – (RSD)
Referencias:
1-Aerosol Measurement: Principles, Technique and Applications. Editado por Klaus Willeke y Paul A. Brown. Van Nostrand Reinhold, New York, 1993.
2-Fundamentals of Aerosol Sampling. Gregory D. Wight. Lewis Publishers, CRC Press, 1994.
25 Comparación de la solubilidad de los cristales de L-tartrato de levalbuterol con la de los cristales de hidrocloruro de levalbuterol en mezclas de HFA 134/Etanol
8
Sal activa
Etanol real % Día 1 µg/g Día 2 µg/g Día 4-5 µg/g Día 6-8 µg/g Día 57-65 µg/g
Tartrato
0,00 Despreciable 0,00 0,02 0,12
2,01
0,07 0,10 0,44 1,18
5,28
0,69 0,94 1,81 2,97
9,80
1,65 2,32 5,30 6,82
Hidrocloruro
0,00 0,08 1,13 0,33 4,20
2,16
4,45 5,01 5,25 10,57
5,25
30,93 31,89 36,54 41,07
10,16
127,78 132,92 134,15 151,96
Los resultados muestran que el L-tratrato de levalbuterol tiene una solubilidad sustancialmente inferior en etanol que el hidrocloruro de levalbuterol. Esta propiedad es deseable en cristales que se van a usar en la preparación de una formulación de un aerosol adaptado para su uso en un inhalador de dosis medidas, debido a que tales formulaciones se preparan comúnmente combinando cristales micronizados con etanol (como un co-disolvente), añadiendo luego el agente propulsor (que forzará a cualquier producto disuelto a salir de la solución, originando potencialmente el crecimiento de los cristales).
9

Claims (1)

  1. imagen1
ES10176026.2T 2002-12-10 2003-12-08 Composición farmacéutica que comprende sal L-hemitartrato de levalbuterol como formulación en aerosol Expired - Lifetime ES2626648T3 (es)

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US432195P 2002-12-10

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ES06110646.4T Expired - Lifetime ES2361172T5 (es) 2002-12-10 2003-12-08 Formulación de aerosol que comprende sal L-tartrato de levalbuterol
ES03786896T Expired - Lifetime ES2263051T3 (es) 2002-12-10 2003-12-08 Uso de l-tartrato de levalbuterol en la produccion de un inhalador de dosis medias.
ES10176026.2T Expired - Lifetime ES2626648T3 (es) 2002-12-10 2003-12-08 Composición farmacéutica que comprende sal L-hemitartrato de levalbuterol como formulación en aerosol

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ES06110646.4T Expired - Lifetime ES2361172T5 (es) 2002-12-10 2003-12-08 Formulación de aerosol que comprende sal L-tartrato de levalbuterol
ES03786896T Expired - Lifetime ES2263051T3 (es) 2002-12-10 2003-12-08 Uso de l-tartrato de levalbuterol en la produccion de un inhalador de dosis medias.

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US (8) US7256310B2 (es)
EP (3) EP2292584B1 (es)
JP (1) JP4570960B2 (es)
KR (3) KR20050088307A (es)
AT (2) ATE324364T1 (es)
AU (1) AU2003295695B2 (es)
CA (1) CA2507572C (es)
CY (2) CY1106315T1 (es)
DE (2) DE60336089D1 (es)
DK (3) DK2292584T3 (es)
ES (3) ES2361172T5 (es)
IL (2) IL168739A (es)
MX (1) MXPA05006087A (es)
NO (1) NO331649B1 (es)
NZ (1) NZ541168A (es)
PL (1) PL212725B1 (es)
PT (3) PT2292584T (es)
SI (2) SI1572622T1 (es)
WO (1) WO2004052835A1 (es)

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