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ES 2 331 421 T3 Venta De Fascículos: Oficina Española De Patentes Y Marcas 11 Número de publicación: 2 331 421 19 OFICINA ESPAÑOLA DE PATENTES Y MARCAS 51 Int. Cl.: C07H 19/01 (2006.01) (2006.01) ESPAÑA A01N 43/90 A61K 31/7048 (2006.01) A61P 33/00 (2006.01) 12 TRADUCCIÓN DE PATENTE EUROPEA T3 96 Número de solicitud europea: 05715877 .6 96 Fecha de presentación : 09.03.2005 97 Número de publicación de la solicitud: 1737876 97 Fecha de publicación de la solicitud: 03.01.2007 54 Título: Avermectina y monosacárido de avermectina, sustituido en la posición 4”- y 4’- respectivamente. 30 Prioridad: 07.04.2004 EP 04008413 73 Titular/es: Merial Limited 3239 Satellite Boulevard, Building 500 Duluth, Georgia 30096, US 45 Fecha de publicación de la mención BOPI: 72 Inventor/es: Jung, Pierre Joseph Marcel; 04.01.2010 Pitterna, Thomas; Quaranta, Laura; Hueter, Ottmar Franz y Murphy-Kessabi, Fiona 45 Fecha de la publicación del folleto de la patente: 74 Agente: Elzaburu Márquez, Alberto 04.01.2010 Aviso: En el plazo de nueve meses a contar desde la fecha de publicación en el Boletín europeo de patentes, de la mención de concesión de la patente europea, cualquier persona podrá oponerse ante la Oficina Europea de Patentes a la patente concedida. La oposición deberá formularse por escrito y estar motivada; sólo se considerará como formulada una vez que se haya realizado el pago de la tasa de oposición (art. 99.1 del Convenio sobre concesión de Patentes Europeas). ES 2 331 421 T3 Venta de fascículos: Oficina Española de Patentes y Marcas. Pº de la Castellana, 75 – 28071 Madrid ES 2 331 421 T3 DESCRIPCIÓN Avermectina y monosacárido de avermectina, sustituido en la posición 4”- y 4’- respectivamente. 5 La presente invención se refiere en particular a ciertos derivados de avermectina y de monosacárido de avermectina, a procesos para preparar dichos derivados, a intermedios en la preparación de dichos derivados y al uso de ciertos derivados para el control de plagas. Se conocen algunos compuestos macrólidos para el control de plagas. Sin embargo, las propiedades biológicas de 10 estos compuestos conocidos no son totalmente satisfactorias, y, como consecuencia, sigue existiendo una necesidad de compuestos adicionales que tengan propiedades pesticidas. Se ha descubierto que algunos derivados desoxi de avermectina y monosacárido de avermectina, que tienen un grupo hidrocarbilo o un grupo sustituido del mismo en la posición 4” o 4’, son útiles en el control de plagas, en 15 particular plagas que son dañinas para el cultivo de plantas y para su material de propagación, siendo representativos la clase insecta, el orden Acarina y la clase nematoda. Por consiguiente, en un primer aspecto, la presente invención proporciona un compuesto de la fórmula (I) 20 25 30 35 40 45 en la que el enlace entre los átomos de carbono 22 y 23 indicado con una línea discontinua es un enlace sencillo o un doble enlace, es 0 ó 1, 50 m R1 representa un grupo alquilo C1-C12, cicloalquilo C3-C8 o alquenilo C2-C12, R2 representa un alquilo C1-C12 sin sustituir o alquilo C1-C12 halógeno-sustituido, cicloalquilo C3-C8 sin sustituir o cicloalquilo C -C halógeno-sustituido, alquenilo C -C sin sustituir o alquenilo C -C halógeno-sustitui- 55 3 8 2 12 2 12 do, alquinilo C2-C8 sin sustituir o alquinilo C2-C8 halógeno-sustituido, CN, arilo o heterociclilo sin sustituir, o arilo o heterociclilo que están, dependiendo de las posibilidades de sustitución en el anillo, de mono- a pen- tasustituidos con sustituyentes seleccionados entre el grupo que consiste en =O, OH, =S, SH, halógeno, CN, NO2, alquilo C1-C12, cicloalquilo C3-C8, haloalquilo C1-C12, alcoxi C1-C12, haloalcoxi C1-C12, alquiltio C1- C , haloalquiltio C -C , alcoxi C -C -alquilo C -C , alquenilo C -C , alquinilo C -C , fenoxi y metilendioxi, 60 12 1 12 1 6 1 6 2 8 2 8 y R3 es hidrógeno, alquilo C1-C12 sin sustituir o alquilo C1-C12 halógeno-sustituido, cicloalquilo C3-C8 sin susti- tuir o cicloalquilo C3-C8 halógeno-sustituido, alquenilo C2-C12 sin sustituir o alquenilo C2-C12 halógeno-sus- tituido, alquinilo C -C sn sustituir o alquinilo C -C halógeno-sustituido, alcoxi C -C sin sustituir o alcoxi 65 2 8 2 8 1 12 C1-C12 halógeno-sustituido, fenoxi sin sustituir, OH, arilo, grupo heterociclilo, CN, -N(R5)2, -SR8, -S(=O)R8, -S(=O)2R8, o -S(=O)2N(R5)2, donde 2 ES 2 331 421 T3 R5 representa H o alquilo C1-C6 que está opcionalmente sustituido con uno a cinco sustituyentes seleccionados entre el grupo que consiste en halógeno, alcoxi C1-C6, cicloalcoxi C3-C8, hidroxi y ciano, alcoxi C1-C6, cicloal- quilo C3-C8, alquenilo C2-C12, alquinilo C2-C8, arilo, bencilo, heteroarilo o arilo, bencilo o heteroarilo que, dependiendo de las posibilidades de sustitución en el anillo, están de mono- a trisustituidos con sustituyentes 5 seleccionados entre el grupo que consiste en OH, halógeno, CN, NO2, alquilo C1-C12, haloalquilo C1-C12, alcoxi C1-C12, haloalcoxi C1-C12, alquiltio C1-C12 y haloalquiltio C1-C12; y R8 representa alquilo C1-C6 que está opcionalmente sustituido con uno a cinco sustituyentes seleccionados entre el grupo que consiste en halógeno, alcoxi C1-C6, hidroxi, ciano y bencilo, arilo, bencilo, heteroarilo o arilo, 10 bencilo o heteroarilo que, dependiendo de las posibilidades de sustitución en el anillo, están de mono- a trisus- tituidos con sustituyentes seleccionados entre el grupo que consiste en OH, halógeno, CN, NO2, alquilo C1-C12, haloalquilo C1-C12, alcoxi C1-C12,C1-C12 haloalcoxi, alquiltio C1-C12 y haloalquiltio C1-C12; y R4 es hidrógeno, alquilo C1-C12 sin sustituir, cicloalquilo C3-C12 sin sustituir, alquenilo C2-C12 sin sustituir o al- 15 quinilo C2-C12 sin sustituir; o R2 y R3 juntos o R3 y R4 juntos representan un puente alquileno de tres a siete miembros o alquenileno de cuatro a siete miembros, para cada uno de los cuales al menos uno, preferiblemente un grupo CH2 puede reemplazarse por O, S o NR6, donde R6 representa hidrógeno; o, si es apropiado, un isómero E/Z y/o tautómero del compuesto 20 de fórmula (I), en cada caso en forma libre o en forma de sal. El símbolo ε representa que la configuración del átomo de carbono en la posición 4’ o 4” es (S) o (R). 25 En un segundo aspecto, la presente invención proporciona un proceso para preparar un compuesto de fórmula (I) 30 35 40 45 50 en la que R1,R2,R3,R4, el enlace entre los átomos de carbono 22 y 23 y m son como se han definido en el primer 55 aspecto, que comprende las etapas de: 60 65 3 ES 2 331 421 T3 (i) sintetizar un compuesto de fórmula (α) 5 10 15 20 25 en la que R1, el enlace entre los átomos de carbono 22 y 23 y m son como se han definido para la fórmula (I) en el primer aspecto y Q es un grupo protector; 30 (ii) hacer reaccionar un disulfuro, una fosfina alifática o aromática y un compuesto de fórmula (α) para producir un derivado de sulfenimina del compuesto de fórmula (α); (iii) oxidar el derivado de sulfenimina del compuesto de fórmula (α) para producir un derivado de sulfinimina del compuesto de fórmula (α); 35 (iva) hacer reaccionar un reactivo organometálico que tiene el grupo R2 con el derivado de sulfinimina del com- puesto de fórmula (α) para producir un derivado de desoxi-sulfinamida-hidrocarbilo del compuesto de fór- mula (α); o 40 (ivb) hacer reaccionar un reactivo de isonitrilo de fórmula 45 en la que R12 es alquilo C1-C12 sin sustituir o de mono- a pentasustituido, cicloalquilo C3-C12 sin sustituir o de mono- a pentasustituido, alquenilo C2-C12 sin sustituir o de mono- a pentasustituido, alquinilo C2-C12 sin sustituir o de mono- a pentasustituido, arilo sin sustituir o de mono- a pentasustituido, bencilo sin sustituir o de mono- a pentasustituido, cicloalquil C3-C12 éster sin sustituir o de mono- a pentasustituido, alquil C1- C éster sin sustituir o de mono- a pentasustituido, alquil C -C sulfona sin sustituir o de mono- a penta- 50 12 1 12 sustituido o alquil C1-C12 nitrito sin sustituir o de mono- a pentasustituido con el derivado de sulfinimina del compuesto de fórmula (α) para producir un derivado de desoxi-amina-hidrocarbilo del compuesto de fórmula (α); o (ivc) hacer reaccionar un reactivo de nitroalquilo de fórmula 55 60 en la que R10 y R11 son independientemente entre sí H, CN, alquilo C1-C12 sin sustituir o de mono- a pentasustituido, cicloalquilo C3-C12 sin sustituir o de mono- a pentasustituido, alquenilo C2-C12 sin sustituir 65 o de mono- a pentasustituido, alquinilo C2-C12 sin sustituir o de mono- a pentasustituido, arilo sin sustituir o de mono- a pentasustituido, bencilo sin sustituir o de mono- a pentasustituido, cicloalquil C3-C12 éster sin sustituir o de mono- a pentasustituido, un alquil C1-C12 éster sin sustituir o de mono- a pentasustituido, 4 ES 2 331 421 T3 alquil C1-C12 sulfona sin sustituir o de mono- a pentasustituido o alquil C1-C12 nitrilo sin sustituir o de mono- a pentasustituido con el derivado de sulfinimina del compuesto de fórmula (α) para producir un derivado de desoxi-amina-hidrocarbilo del compuesto de fórmula (α); y 5 (va) retirar el grupo sulfinilo y un grupo protector Q en una etapa o secuencialmente uno después de otro para producir un compuesto de fórmula (I), en la que cada uno de R3 y R4 representa hidrógeno, o (vb) retirar solamente el grupo sulfinilo, realizando reacciones en uno o más de los grupos R2,R3 y R4 para modificar el grupo y después retirar el grupo protector Q para producir un compuesto de fórmula (I), o 10 (vc) retirar el grupo protector Q si el grupo sulfinilo se retira durante (iva) o (ivb) o (ivc) para producir un compuesto de fórmula (I).
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