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ES2660594T3 - Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina - Google Patents

Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina Download PDF

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ES2660594T3
ES2660594T3 ES09800657.0T ES09800657T ES2660594T3 ES 2660594 T3 ES2660594 T3 ES 2660594T3 ES 09800657 T ES09800657 T ES 09800657T ES 2660594 T3 ES2660594 T3 ES 2660594T3
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oligosaccharide
oligosaccharides
methods
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compositions related
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Gerald B. Pier
Nikolay Nifantiev
Yury Tsvetkov
Marina Gening
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Brigham and Womens Hospital Inc
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    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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Abstract

Una composición que comprende un conjugado de oligosacárido-vehículo que comprende un oligosacárido conjugado a un vehículo a través de un enlazador que es **(Ver fórmula)** o **(Ver fórmula)** en las que n es mayor de 1, m es un número seleccionado de 1 a 10, p es un número seleccionado de 1 a 20 y R es H o un grupo alquilo, y en donde el enlazador está O-enlazado al oligosacárido y N-enlazado al vehículo, y en donde la composición es capaz de estimular una respuesta inmunitaria.

Description

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Se pretende que los oligosacáridos de la invención imiten regiones de PNAG o dPNAG. De este modo, cuando se utilizan in vivo, los conjugados de oligosacárido-vehículo inducen respuestas inmunitarias dirigidas a regiones del oligosacárido que son similares o idénticas a PNAG y/o dPNAG y, por tanto, dichas respuestas inmunitarias son
5 útiles para dirigirse a especies bacterianas que fabrican o son capaces de fabricar PNAG y/o dPNAG.
En algunos aspectos de la invención, los oligosacáridos comprenden solamente unidades de D-glucosamina, o solamente N-acetil-D-glucosamina, o una relación predeterminada y orden de ambos tipos de estos monómeros. Se pretende que la relación y el orden imiten, en algunas realizaciones, las relaciones y órdenes que se encuentran en
10 un PNAG natural. Los oligosacáridos se manipulan de acuerdo con la invención para comprender un separador (o un enlazador, ya que los términos se usan de manera indistinta en el presente documento) que tienen un grupo tiol en su extremo (por ejemplo, su extremo reductor).
La preparación de oligosacáridos comprende grupos amino, tal como oligosacáridos de glucosamina unidos (u
15 oligoglucosaminas, ya que los términos se usan de manera indistinta en el presente documento) para su conjugación con uno o más vehículos, ha supuesto un desafío en la técnica. Esto se debe parcialmente a que la síntesis estereoespecífica de la glucosamina unida requiere el uso de grupos acilo N protectores participantes pero temporales (los denominados "grupos participantes") de los donantes de glicosilo para formar el necesario enlace βglucósido entre los monómeros. N-ftaloilo, N-tricloroetoxicarbonilo y algunos otros restos son adecuados como
20 grupos participantes. Sin embargo, algunos otros grupos participantes son menos adecuados incluidos los grupos participantes de N-acetilo que están presentes en algunos de los oligosacáridos considerados en la invención. A modo de ejemplo, los donantes de glicosilo N-acetilados son de baja reactividad y proporcionan solamente bajos rendimientos de productos de glicosilación. Además, la presencia de grupos N-acetilo en el donante de glicosilo complica la reacción de glicosilación debido a la formación del intermedio oxazolina, la migración de los grupos N
25 acetilo, y otras reacciones químicas indeseables.
Con respecto a las glucosaminas unidas, su estructura y, más especialmente, el número de grupos amino que contienen, requiere la introducción del enlazador antes de la liberación total de los grupos amino. La eliminación de los grupos protectores de N temporales anteriormente mencionados para preparar el oligosacárido libre se lleva a
30 cabo en condiciones básicas. El reactivo más eficaz para eliminar un grupo participante de N-ftaloilo es el hidrato de hidrazina en etanol en ebullición. Este reactivo también es eficaz para eliminar los grupos protectores de O-acilo incluidos los grupos acetilo y benzoílo que pueden estar incluidos en el oligosacárido de interés.
Los ligandos comercialmente disponibles que se han usado para la unión de ligandos que contienen grupos amino a
35 proteínas son S-acetiltioglicolato de pentafluorofenilo (estructura química 8 mostrada en los Ejemplos) y acetilsulfanil-propionato de N-hidroxisuccinimidilo 3 (estructura química 12 mostrada en los Ejemplos). Estos reactivos enlazadores se pueden usar para introducir un resto tiol en un oligosacárido; sin embargo, como se describe con mayor detalle en los Ejemplos, ambos son inestables en las condiciones de eliminación de los grupos ftaloilo. El Ejemplo 5 muestra que un enlazador basado en ácido tioglicólico experimenta reordenamiento oxidativo, y
40 el Ejemplo 6 muestra que un derivado del ácido 3-mercaptopropiónico proporciona una mezcla compleja de productos secundarios. Ambas transformaciones dan como resultado la pérdida de la necesaria función tiol.
Por tanto, la invención se basa en parte en el descubrimiento y el uso de una clase de enlazadores que es eficaz y mejor que los enlazadores anteriormente conocidos para conjugar oligosacáridos (incluidas las versiones que
45 contienen amina de los mismos) con un vehículo tal como una proteína. Esta clase de enlazadores se define como derivados del ácido ω-acetilsulfanil carbónico de Fórmula I (donde n > 1).
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Fórmula I
50 Esta clase de enlazadores proporciona una N-acilación eficaz durante la unión a un oligosacárido. El enlazador puede ser un éster activo de Fórmula I o su derivado ciano, azido, o haloide. Puede haber otro derivado de Fórmula I siempre que dicho derivado sea activo como agente acilante y por tanto adecuado para su unión a los oligosacáridos de la presente invención. Y representa un grupo bloqueante temporal de átomos de azufre, que son conocidos en la
55 técnica y que incluyen grupos acilo y acetilo. La eliminación del grupo Y libera un grupo SH que es necesario para la unión del oligosacárido al vehículo. X representa cualquier grupo saliente que proporcione la capacidad acilante necesaria al compuesto de Fórmula I.
Se entenderá que cualquiera de las clases de enlazadores proporcionadas por la invención se puede usar para 60 conjugar los oligosacáridos con los compuestos vehículo. A modo de ejemplo, una clase de enlazador puede comprender la estructura de Fórmula II (donde n > 1):
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Claims (1)

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ES09800657.0T 2008-07-21 2009-07-21 Métodos y composiciones relacionados con oligosacáridos sintéticos de beta-1,6 glucosamina Active ES2660594T3 (es)

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