ES2252958T3 - Nitratos de cetirizina. - Google Patents

Nitratos de cetirizina.

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Publication number
ES2252958T3
ES2252958T3 ES99938300T ES99938300T ES2252958T3 ES 2252958 T3 ES2252958 T3 ES 2252958T3 ES 99938300 T ES99938300 T ES 99938300T ES 99938300 T ES99938300 T ES 99938300T ES 2252958 T3 ES2252958 T3 ES 2252958T3
Authority
ES
Spain
Prior art keywords
nitrate
cetirizine
salt
compound
treatment
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
ES99938300T
Other languages
English (en)
Inventor
Piero Del Soldato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nicox SA
Original Assignee
Nicox SA
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Filing date
Publication date
Application filed by Nicox SA filed Critical Nicox SA
Application granted granted Critical
Publication of ES2252958T3 publication Critical patent/ES2252958T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • G06Q20/00—Payment architectures, schemes or protocols
    • G06Q20/04—Payment circuits
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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    • A—HUMAN NECESSITIES
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
    • C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
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    • 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
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    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/86—Hydrazides; Thio or imino analogues thereof
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
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    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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Abstract

Sal nitrato de Cetirizina. Un objeto de la presente invención son sales nitrato de un compuesto o sus composiciones farmacéuticas, para usar para el tratamiento de patologías del sistema respiratorio, específicamente enfermedades pulmonares crónicas (enfermedades pulmonares obstructivas crónicas (COPD)), tales como asma, bronquitis, enfisema, tromboembolia, enfermedades pulmonares no eficaces, estando caracterizado dicho compuesto por contener al menos un grupo reactivo capaz de salificarse con ácido nítrico, dicho compuesto es Cetirizina que tiene la fórmula (II)

Description

Nitratos de cetirizina.
Sales nitrato medicinales.
La presente invención se refiere a compuestos, o composiciones farmacéuticas de los mismos, para uso sistémico y no sistémico, para emplear en el tratamiento de patologías del sistema respiratorio con o sin base etiopatogenética infecciosa, específicamente enfermedades pulmonares crónicas (enfermedades pulmonares obstructivas crónicas (COPD)), tales como asma, bronquitis, enfisema, tromboembolia con menores efectos secundarios comparado con los fármacos usados actualmente para el tratamiento de estas patologías.
Se sabe en la técnica que para el tratamiento de estas patologías los productos más usados son Salbutamol, Salmeterol, etc. Véase por ejemplo, el volumen "Textbook of Therapeutics - Drugs and Disease Management - 6ª Edición 1996" página 685. Estos productos son eficaces pero tienen el inconveniente de provocar efectos secundarios en particular hacia el aparato cardiovascular. Dichos productos deben administrarse con precaución a pacientes que padecen patologías cardiovasculares.
Otros productos usados en estas patologías como tales o como coadyuvantes de otros medicamentos son por ejemplo Ambroxol y Bromhexina, cuya administración va acompañada también por la presencia de efectos secundarios para el aparato gastrointestinal, tales como quemaduras y sensibilidad gástrica.
Hey et al. en Arzneium.-Forsch./Drug Res. 1996, 46 (1), páginas 153-158 presentaron un estudio referido a la evaluación del potencial arritmiogénico de una serie de antagonistas de histamina H_{1} de segunda generación, en un modelo experimental predictivo de los efectos ECG negativos en el hombre. Los resultados demostraron que en este modelo la cetirizina y otros fármacos ensayados estaban desprovistos de efectos cardiovasculares.
Se necesitaba tener compuestos disponibles y sus composiciones farmacéuticas, eficaces en el tratamiento de patologías del sistema respiratorio, combinado con menores efectos secundarios para el aparato cardiovascular y/o el aparato gastrointestinal.
Se han descubierto inesperada y sorprendentemente compuestos específicos y composiciones de los mismos que resuelven el problema técnico mencionado anteriormente.
Un objeto de la presente invención son sales nitrato de un compuesto o sus composiciones farmacéuticas, para usar para el tratamiento de patologías del sistema respiratorio, específicamente enfermedades pulmonares crónicas (enfermedades pulmonares obstructivas crónicas (COPD)), tales como asma, bronquitis, enfisema, tromboembolia, enfermedades pulmonares no eficaces, estando caracterizado dicho compuesto por contener al menos un grupo reactivo capaz de salificarse con ácido nítrico, dicho compuesto es Cetirizina que tiene la fórmula (II)
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En las composiciones de acuerdo con la presente invención puede usarse también el isómero óptico D, L o el enantiómero racémico. En general una forma isomérica tiene mayor actividad con respecto a la otra, por ejemplo, la forma D con respecto a la forma L y viceversa.
Las sales de la invención contienen al menos un mol de ión nitrato/mol de precursor. Preferiblemente la proporción entre los moles de ión nitrato y los de precursor es unitaria; pueden obtenerse sales con una mayor proporción molar cuando en la molécula hay otros grupos amina suficientemente básicos para formar un enlace iónico con el anión nitrato.
Las sales de la presente invención se formulan en las composiciones farmacéuticas correspondientes de acuerdo con técnicas conocidas en el campo, junto con los excipientes habituales; véase por ejemplo el volumen "Remington's Pharmaceutical Sciences 15ª Ed.".
El precursor de las sales se prepara de acuerdo con los métodos descritos en el Merck Index 14ª Ed.
Las sales de la presente invención pueden obtenerse de acuerdo con uno de los siguientes métodos.
Si el precursor a usar para formar la sal de acuerdo con la invención está disponible como una base libre, o como una sal correspondiente, solubles ambas en un disolvente orgánico que preferiblemente no contiene grupos hidroxilo en la molécula, tales como por ejemplo acetonitrilo, acetato de etilo, tetrahidrofurano, etc., la sal nitrato se prepara disolviendo la sustancia o su sal en dicho disolvente a una concentración preferiblemente igual o mayor del 10% v/v, y añadiendo después la cantidad requerida de ácido nítrico concentrado, preferiblemente diluido antes de la adición en el mismo disolvente usado anteriormente para disolver el compuesto, preferiblemente enfriando la mezcla durante y después de dicha adición a temperaturas entre 20ºC y 0ºC, recuperando el producto obtenido por filtración y opcionalmente lavando el sólido con el mismo disolvente enfriado.
Cuando el precursor o su sal disponible sean ligeramente solubles en el disolvente mencionado anteriormente, se añade un disolvente hidroxilado a dicho disolvente para mejorar la solubilidad. Los ejemplos de dicho disolvente hidroxilado son alcohol metílico, alcohol etílico y agua. La preparación puede acelerarse diluyendo con un disolvente apolar después de la adición de ácido nítrico.
Cuando el precursor se salifica con un halogenuro de hidrógeno, la sal con ácido nítrico puede prepararse añadiendo nitrato de plata a la solución del halogenuro en el disolvente anterior. Después de retirar por filtración el halogenuro de plata, la solución se concentra y se enfría para recuperar la sal nitrato por precipitación.
Partiendo de una sal del precursor en la que el anión es diferente de cloruro es preferible, sin embargo, tratar una solución acuosa de dicha sal con una solución saturada de sal carbonato o bicarbonato sódico o potásico, o con una solución diluida de hidróxido sódico o potásico, extrayendo después la fase acuosa con un disolvente orgánico adecuado (por ejemplo, disolventes halogenados, ésteres, éteres), deshidratando y evaporando después la solución orgánica, disolviendo el residuo obtenido de esta manera en los disolventes mencionados anteriormente que no contienen grupos hidroxilo, por ejemplo, acetonitrilo, o en una mezcla de dicho disolvente con un disolvente hidroxilado, y siguiendo después los métodos de preparación descritos anteriormente.
Las sales y composiciones de la presente invención pueden usarse para la administración sistémica, por ejemplo, pueden administrarse por vía oral, tales como para expectorantes; por vía intramuscular, intravenosa, etc.; o pueden usarse para administraciones no sistémicas, por ejemplo, en forma de aerosoles o aplicaciones tópicas. En general, las sales de la invención se usan para las mismas aplicaciones terapéuticas de los precursores.
Las sales nitrato de la invención han aumentado la seguridad general haciendo frente a los precursores.
Las dosis administradas son las típicas de los precursores; sin embargo como los productos de la invención muestran una eficacia terapéutica mayor que la de los precursores, pueden usarse también a dosis mayores que las de los precursores sin producir efectos secundarios.
Otras aplicaciones de los productos de la invención son como antihistamínicos (antialérgicos) por ejemplo para aplicaciones oftálmicas. Pueden administrase por vía sistémica o no sistémica, como se ha indicado anteriormente, o también en la forma de composiciones oftálmicas, tales como colirios, etc.
Los siguientes ejemplos se dan únicamente con propósito de ilustrar la invención.
Ejemplo 1 Estudios de toxicidad grave de las sales de la invención
Los productos se han administrado en suspensión de carboximetilcelulosa del 2% en peso a grupos de 10 ratones cada uno.
La toxicidad aguda de la sal se evaluó por administración oral de dosis individuales de los compuestos a grupos de 10 ratas cada uno, aumentado hasta 100 mg/kg.
Los animales se mantuvieron en observación durante 14 días, registrando la incidencia de letalidad y la aparición de síntomas tóxicos.
Después de administrar una dosis de 100 mg/kg no se observaron tampoco signos de toxicidad aparente.
Ejemplo 2 Preparación de sal nitrato de cetirizina
La sal se prepara añadiendo a una solución de Cetirizina (2 g, 5,14 mmol) en una mezcla de disolvente preparada con acetonitrilo (10 ml) y tetrahidrofurano (5 ml), 1,23 ml de la solución de ácido nítrico en acetonitrilo (3,5 ml tomados de una solución obtenida añadiendo acetonitrilo a 2,7 ml de ácido nítrico al 65% y llevando a un volumen final de 10 ml con acetonitrilo). Se obtiene un sólido amorfo que en el análisis elemental corresponde a la sal nitrato de Cetirizina:
C H N Cl
Calculado 55,81% 5,79% 9,29% 7,84%
Encontrado 55,84% 5,75% 9,22% 7,83%
Ensayos farmacológicos Ejemplo 3 Actividad antihistamínica en cobaya de nitrato de Cetirizina y clorhidrato de Cetirizina - estudios sobre la broncoconstricción experimental
Los animales se prepararon de acuerdo con el método de Del Soldado et al., J. Pharmacol. Methods 5 279 1981 para el estudio de la actividad cardiorrespiratoria. 0,1 ml de una solución salina de histamina (2 \mug/kg) se inyectaron por vía intravenosa a los animales. Se formaron tres grupos, estando compuesto cada grupo por 8 animales. Se administró nitrato de Cetirizina, clorhidrato de Cetirizina, o el vehículo solo, por vía intravenosa a una dosis de 77 \mumol/\mug.
Se midió la variación de aire tidal antes y después de la administración de capsaicina mediante un aparato Konzett modificado como se describe en la referencia de Del Soldado mencionada anteriormente, conectado a un sistema poligráfico.
En la siguiente Tabla II se expresa la respuesta del animal para grupo tratado como valores porcentuales con respecto al control.
Como se ha indicado en la Tabla, la sal nitrato de Cetirizina posee una actividad antihistamínica mejorada a diferencia del clorhidrato de Cetirizina.
TABLA II
Tratamiento Broncoconstricción (%)
Vehículo 100
Nitrato de Cetirizina 0
Clorhidrato de Cetirizina 40

Claims (10)

1. Sal nitrato de Cetirizina que tiene la fórmula (II)
2
y enantiómeros y mezcla racémica de la misma.
2. Una sal nitrato de acuerdo con la reivindicación 1 en la que la sal de dicho compuesto contiene al menos un mol de ión nitrato/mol de compuesto.
3. Composiciones farmacéuticas que comprenden un compuesto de acuerdo con la reivindicación 1 y un excipiente farmacéuticamente aceptable.
4. Una sal nitrato de acuerdo con la reivindicación 1 para usar como medicamento.
5. Uso de sales nitrato de acuerdo con la reivindicación 1 para fabricar un medicamento para el tratamiento de patologías del sistema respiratorio.
6. Uso de sales nitrato de acuerdo con la reivindicación 1 para fabricar un medicamento para el tratamiento de alergias.
7. Uso de sales nitrato de acuerdo con la reivindicación 1 para fabricar un medicamento para el tratamiento del asma.
8. La composición farmacéutica de la reivindicación 3, en la que la composición está en una forma que puede administrarse por administración no sistémica.
9. La composición farmacéutica de la reivindicación 7, en la que la composición está en una forma que puede administrarse como aerosol.
10. La composición farmacéutica de la reivindicación 3, en la que la composición está en una forma administrable por vía tópica.
ES99938300T 1998-07-28 1999-07-20 Nitratos de cetirizina. Expired - Lifetime ES2252958T3 (es)

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