ES2607647T3 - Modificador del sabor dulce - Google Patents

Modificador del sabor dulce Download PDF

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ES2607647T3
ES2607647T3 ES12824307.8T ES12824307T ES2607647T3 ES 2607647 T3 ES2607647 T3 ES 2607647T3 ES 12824307 T ES12824307 T ES 12824307T ES 2607647 T3 ES2607647 T3 ES 2607647T3
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alkyl
category
substituted
alkylene
branched
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Catherine Tachdjian
Xiao Qing Tang
Donald S. Karanewsky
Guy Servant
Xiaodong Li
Feng Zhang
Qing Chen
Hong Zhang
Timothy Davis
Vincent Darmohusodo
Melissa Wong
Victor Selchau
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Firmenich Inc
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Senomyx Inc
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
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Abstract

Un compuesto que tiene la Fórmula estructural (I):**Fórmula** o una sal o solvato del mismo, en donde R1 y R2 son independientemente hidrógeno o alquilo C1 a C6; L es alquileno C1 a C12 o alquileno C1 a C12 sustituido; M es -NR4-C(O)- o -C(O)-NR4-; R4 es hidrógeno o alquilo C1 a C6; o, alternativamente, cuando M es -NR4-C(O)-, R4 y uno o más átomos de L, junto con el nitrógeno al que están unidos, forman un anillo heterocíclico de 5 a 8 miembros que está opcionalmente sustituido; y R3 es alquilo C1 a C12, alquilo C1 a C12 sustituido, heterociclilo de 5 a 8 miembros o heterociclilo de 5 a 8 miembros sustituido; en donde, cuando se indica que un grupo está sustituido, el uno o más sustituyentes se seleccionan del grupo que consiste en halo, amino, N-alquilamino, N,N-dialquilamino, hidroxilo, alcoxi, alquilo, arilo, heteroarilo, heterociclilo, carbociclilo, >=O, >=S, >=NRa, >=NORa, -CN, -C(O)Rb, -C(O)ORa, -C(O)NRaRa, -OC(O)OH, -OC(O)ORa, -NRaC(O)Rb, -NRaC(O)ORa y -NRaC(O)NRaRa, en donde cada Ra es independientemente hidrógeno o alquilo incluyendo alquilo lineal, ramificado y cíclico; o, alternativamente, dos Ra, tomados junto con el nitrógeno al que están unidos, forman un anillo heterocíclico; y cada Rb es alquilo incluyendo alquilo lineal, ramificado y cíclico; con la condición de que el compuesto no sea ácido 4-amino-5-(2,2-dimetil-3-oxo-3-(propilamino)propoxi)-2-metil-quinolin-3-carboxílico.

Claims (13)

  1. imagen1
    REIVINDICACIONES
    1. Un compuesto que tiene la Fórmula estructural (I):
    imagen2
    5
    o una sal o solvato del mismo, en donde
    R1 y R2 son independientemente hidrógeno o alquilo C1 a C6;
    L es alquileno C1 a C12 o alquileno C1 a C12 sustituido;
    M es -NR4-C(O)-o -C(O)-NR4-;
    10 R4 es hidrógeno o alquilo C1 a C6; o, alternativamente, cuando M es -NR4-C(O)-, R4 y uno o más átomos de L, junto con el nitrógeno al que están unidos, forman un anillo heterocíclico de 5 a 8 miembros que está opcionalmente sustituido; y
    R3 es alquilo C1 a C12, alquilo C1 a C12 sustituido, heterociclilo de 5 a 8 miembros o heterociclilo de 5 a 8 miembros sustituido;
    15 en donde, cuando se indica que un grupo está sustituido, el uno o más sustituyentes se seleccionan del grupo que consiste en halo, amino, N-alquilamino, N,N-dialquilamino, hidroxilo, alcoxi, alquilo, arilo, heteroarilo, heterociclilo, carbociclilo, =O, =S, =NRa, =NORa, -CN, -C(O)Rb, -C(O)ORa, -C(O)NRaRa, -OC(O)OH, -OC(O)ORa, -NRaC(O)Rb, -NRaC(O)ORa y -NRaC(O)NRaRa, en donde cada Ra es independientemente hidrógeno o alquilo incluyendo alquilo lineal, ramificado y cíclico; o, alternativamente, dos Ra, tomados junto con el nitrógeno al que están unidos, forman
    20 un anillo heterocíclico; y cada Rb es alquilo incluyendo alquilo lineal, ramificado y cíclico; con la condición de que el compuesto no sea ácido 4-amino-5-(2,2-dimetil-3-oxo-3-(propilamino)propoxi)-2-metil-quinolin-3-carboxílico.
  2. 2. El compuesto según la reivindicación 1, en el que R1 y R2 son ambos hidrógeno; y/o en el que el alquileno es
    lineal, ramificado, cíclico o una combinación de los mismos; y/o en el que el alquilo es lineal, ramificado, cíclico o una 25 combinación de los mismos.
  3. 3. El compuesto según la reivindicación 1, que está representado por la Fórmula estructural (Ia):
    imagen3
    30 en donde,
    L es alquileno C1 a C12 o alquileno C1 a C12 sustituido;
    R4 es hidrógeno o alquilo C1 a C6; o, alternativamente, R4 y uno o más átomos de L, junto con el nitrógeno al que están unidos, forman un anillo heterocíclico de 5 a 8 miembros que está opcionalmente sustituido; y
    R3 es alquilo C1 a C12, alquilo C1 a C12 sustituido, heterociclilo de 5 a 8 miembros o heterociclilo de 5 a 8 miembros 35 sustituido;
    en donde, cuando se indica que un grupo está sustituido, el uno o más sustituyentes se seleccionan del grupo que consiste en halo, amino, N-alquilamino, N,N-dialquilamino, hidroxilo, alcoxi, alquilo, arilo, heteroarilo, heterociclilo, carbociclilo, =O, =S, =NRa, =N-ORa, -CN, C(O)Rb, -C(O)ORa, -C(O)NRaRa, -OC(O)OH, -OC(O)ORa, -NRaC(O)Rb, -NRaC(O)ORa y -NRaC(O)NRaRa, en donde cada Ra es independientemente hidrógeno o alquilo incluyendo alquilo lineal, ramificado y cíclico; o, alternativamente, dos Ra, tomados junto con el nitrógeno al que están unidos, forman un anillo heterocíclico; y cada Rb es alquilo incluyendo alquilo lineal, ramificado y cíclico.
    imagen4
    5 4. El compuesto según la reivindicación 3, en el que L es alquileno C3 a C6 ramificado o cíclico; R4 es hidrógeno; y R3 es alquilo C3 a C6 ramificado o alquilo C1 a C6 lineal.
  4. 5. El compuesto según la reivindicación 1, que está representado por la Fórmula estructural (Ib): 10
    imagen5
    en el que: L es alquileno C1 a C12 o alquileno C1 a C12 sustituido; R4 es hidrógeno o alquilo C1 a C6; y
    15 R3 es alquilo C1 a C12, alquilo C1 a C12 sustituido, heterociclilo de 5 a 8 miembros, heterociclilo de 5 a 8 miembros sustituido.
  5. 6. El compuesto según la reivindicación 5, en el que L es alquileno C1 a C6 lineal o alquileno C3 a C6 ramificado; R4 es hidrógeno; y
    20 R3 es alquilo C1 a C6 lineal o alquilo C3 a C6 ramificado o cíclico.
  6. 7.
    El compuesto según la reivindicación 1, que se selecciona del grupo que consiste en
  7. 8.
    El compuesto según una cualquiera de las reivindicaciones 1 a 7, que potencia el dulzor de un edulcorante a un pH de 2,5 a 8,5.
    imagen6
    imagen7
    imagen8
    imagen9
    10
    15 9. Una composición ingerible que comprende un compuesto según una cualquiera de las reivindicaciones 1 a 8; y opcionalmente un excipiente ingeriblemente aceptable.
  8. 10. La composición ingerible según la reivindicación 9, que comprende además uno o más edulcorantes, en donde opcionalmente el edulcorante se selecciona del grupo que consiste en sacarosa, fructosa, glucosa, galactosa, 20 manosa, lactosa, tagatosa, maltosa, jarabe de maíz (incluyendo jarabe de maíz con alto contenido de fructosa), Dtriptófano, glicina, eritritol, isomalt, lactitol, manitol, sorbitol, xilitol, maltodextrina, maltitol, isomalt, jarabe de glucosa hidrogenado (HGS), hidrolizado de almidón hidrogenado (HSH), esteviósido, rebaudiósido A, otros glucósidos basados en Stevia, carrelamo, otros edulcorantes basados en guanidina, sacarina, acesulfamo-K, ciclamato, sucralosa, alitamo, mogrósido, neotamo, aspartamo, otros derivados de aspartamo, y combinaciones de los mismos; 25 o que tiene un sabor dulce incrementado en comparación con la composición ingerible que no contiene el compuesto de una cualquiera de las reivindicaciones 1 a 8; o que está en la forma de una composición farmacéutica, un producto nutricional, un complemento dietético, un medicamento de venta libre, un producto de cuidado oral, o en la forma de un producto alimenticio o de bebida, en donde el producto alimenticio o de bebida se selecciona opcionalmente del grupo que consiste en la categoría de las sopas; la categoría de los alimentos procesados 30 desecados; la categoría de las bebidas; la categoría de las comidas preparadas; la categoría de los alimentos enlatados o conservados; la categoría de los alimentos procesados congelados; la categoría de los alimentos procesados refrigerados; la categoría de los alimentos de aperitivo; la categoría de los artículos horneados; la categoría de la repostería; la categoría de los productos lácteos; la categoría de los helados; la categoría de las comidas de sustitución; la categoría de la pasta y los tallarines; la categoría de las salsas, los aderezos y los
    35 condimentos; la categoría de los alimentos infantiles; la categoría de los untes; revestimientos dulces, almíbares o glaseados; y combinaciones de los mismos, en donde opcionalmente el producto alimenticio o de bebida es para consumo humano o animal.
  9. 11. La composición ingerible según la reivindicación 9, que está en la forma de un producto alimenticio o de bebida, una composición farmacéutica, un producto nutricional, un complemento dietético, un medicamento de venta libre o un producto de cuidado oral.
    5 12. Un método para incrementar el sabor dulce de una composición, que comprende poner en contacto la composición del mismo con un compuesto según una cualquiera de las reivindicaciones 1 a 8 para formar una composición modificada.
  10. 13. Un método para impartir un perfil temporal y/o un perfil de sabor más similar al azúcar a una composición
    10 edulcorante, que comprende combinar un compuesto según una cualquiera de las reivindicaciones 1 a 8 y uno o más edulcorantes en la composición edulcorante.
  11. 14. Una composición potenciadora del dulce, que comprende un compuesto según una cualquiera de las reivindicaciones 1 a 8 en una cantidad eficaz para proporcionar dulzor en combinación con una primera cantidad de
    15 edulcorante, en donde el dulzor es mayor que el dulzor proporcionado por la primera cantidad de edulcorante sin el compuesto.
  12. 15. Una formulación de concentrado saborizante que comprende
    i) como ingrediente modificador del sabor, un compuesto según una cualquiera de las reivindicaciones 1 a 8;
    20 ii) un portador; y
    iii) opcionalmente al menos un adyuvante.
  13. 16. La formulación de concentrado saborizante según la reivindicación 15, en la que el al menos un adyuvante comprende uno o más agentes saborizantes; y/o en la que el al menos un adyuvante comprende uno o más edulcorantes; o en la que el al menos un adyuvante comprende uno o más ingredientes seleccionados del grupo que 25 consiste en un emulsionante, un estabilizante, un conservante antimicrobiano, un antioxidante, vitaminas, minerales, grasas, almidones, concentrados y aislados proteínicos, sales, un reductor del punto de congelación, un agente de nucleación, y combinaciones de los mismos; y/o que está en una forma seleccionada del grupo que consiste en un líquido, un sólido, un semisólido, un material espumoso, una pasta, un gel, una crema, una loción, y combinaciones de los mismos; y/o en la que el compuesto de una cualquiera de las reivindicaciones 1 a 8 está en una
    30 concentración que es al menos 2 veces la concentración en una composición lista para usar.
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