AR109931A1 - Compuesto inhibidor de la prostaglandina d sintasa hematopoyética (h-pgds), composición farmacéutica que lo comprende y uso del compuesto para fabricar un medicamento - Google Patents

Compuesto inhibidor de la prostaglandina d sintasa hematopoyética (h-pgds), composición farmacéutica que lo comprende y uso del compuesto para fabricar un medicamento

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Publication number
AR109931A1
AR109931A1 ARP170102843A ARP170102843A AR109931A1 AR 109931 A1 AR109931 A1 AR 109931A1 AR P170102843 A ARP170102843 A AR P170102843A AR P170102843 A ARP170102843 A AR P170102843A AR 109931 A1 AR109931 A1 AR 109931A1
Authority
AR
Argentina
Prior art keywords
alkyl
substituted
fluoro
oxo
independently selected
Prior art date
Application number
ARP170102843A
Other languages
English (en)
Inventor
Eugene L Stuart
Smith Emilie Despagnet
Stephen Andrew Thomson
Barry George Shearer
Christie Schulte
Ashley Paul Hancock
Yu Guo
David Norman Deaton
Original Assignee
Glaxosmithkline Ip Dev Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Glaxosmithkline Ip Dev Ltd filed Critical Glaxosmithkline Ip Dev Ltd
Publication of AR109931A1 publication Critical patent/AR109931A1/es

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    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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    • C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
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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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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Un compuesto inhibidor de la prostaglandina D sintasa hematopoyética (H-PGDS) que está representado por la fórmula (1), en donde: X se selecciona de: carbono y nitrógeno; Y se selecciona de: hidrógeno y CH₃; Y¹ está ausente o CH₃; Z es NH u O; a es 0 ó 1; R se selecciona de: O, NH, CH₂ y alquilo C₁ sustituido con halógeno; R¹ se selecciona de: arilo, arilo sustituido de 1 a 4 veces con Rᵃ, heteroarilo, heteroarilo sustituido de 1 a 4 veces con Rᵃ, bicicloheteroarilo, y bicicloheteroarilo sustituido de 1 a 4 veces con Rᵃ; R² se selecciona de: O y S; R³ se selecciona de: arilo, arilo sustituido de 1 a 4 veces con Rᵇ, cicloalquilo, cicloalquilo sustituido de 1 a 4 veces con Rᵇ, heterociclo, heterociclo sustituido de 1 a 4 veces con Rᵇ, heteroarilo, heteroarilo sustituido de 1 a 4 veces con Rᵇ, bicicloheteroarilo, y bicicloheteroarilo sustituido de 1 a 4 veces con Rᵇ; cada Rᵃ se selecciona independientemente de: fluoro, cloro, bromo, yodo, -OH, alquilo C₁₋₆, alquilo C₁₋₆ sustituido con 1 a 5 sustituyentes independientemente seleccionados de: fluoro, cloro, bromo, yodo, alquiloxi C₁₋₄, -OH, alquilo C₁₋₄, oxo, -COOH, -NO₂, -NH₂ y -CN, ciano, -O-alquilo C₁₋₆, -O-alquilo C₁₋₆ sustituido con 1 a 5 sustituyentes independientemente seleccionados de: fluoro, cloro, bromo, yodo, alquiloxi C₁₋₄, -OH, alquilo C₁₋₄, oxo, -COOH, -NO₂, -NH₂ y -CN, -C(O)O-alquilo C₁₋₆, y -C(O)O-alquilo C₁₋₆ sustituido de 1 a 5 veces con fluoro; cada Rᵇ se selecciona independientemente de: ciano, fluoro, cloro, bromo, yodo, alquilo C₁₋₆, Rᵉ, -O-alquilo C₁₋₆, -ORᵉ, oxo, hidroxilo, cicloalquilo, cicloalquilo sustituido de 1 a 4 veces con Rᶠ, amino, -NHRˣ, donde Rˣ se selecciona de arilo, heteroarilo, cicloalquilo, heterocicloalquilo, -O-alquilo C₁₋₆, -O-alquilo C₁₋₆ sustituido con de 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, y -OH, alquilo C₁₋₆, y alquilo C₁₋₆ sustituido con de 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -OC₁₋₆alquilo, -COOH, -NH₂, -NH-cicloalquilo, y -CN, heteroarilo, heteroarilo sustituido de 1 a 4 veces con Rᶠ, heterociclo, heterociclo sustituido de 1 a 4 veces con Rᶠ, -SO₂H, y -SO₂-alquilo C₁₋₆; cada Rᶠ se selecciona independientemente de: fluoro, cloro, bromo, yodo, alquilo C₁₋₆, Rᵉ, oxo, -OH, amino, -NHRˣ¹, donde Rˣ¹ se selecciona de arilo, heteroarilo, cicloalquilo, heterocicloalquilo, alquilo C₁₋₆, y alquilo C₁₋₆ sustituido con de 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -O-alquilo C₁₋₆, -COOH, -NH₂, y -CN, -NRˣ²Rˣ³, donde Rˣ² y Rˣ³ se selecciona uno independientemente de: arilo, heteroarilo, cicloalquilo, heterocicloalquilo, alquilo C₁₋₆, y alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, nitro, y ciano, y cada Rᵉ se selecciona independientemente de: alquilo C₁₋₆ sustituido con 1 a 9 sustituyentes independientemente seleccionados de: fluoro, cloro, bromo, yodo, alquilo C₁₋₆, -O-alquilo C₁₋₆, -O-alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, -CN, y fenilo, oxo, =N, hidroxilo, amino, -NHRˣˣ, o =NRˣˣ, donde Rˣˣ se selecciona de arilo, heteroarilo, cicloalquilo, heterocicloalquilo, ciano, alquilo C₁₋₆, y alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -O-C₁₋₅ alquilo, -O-alquilo C₁₋₅ sustituido de 1 a 6 veces con fluoro, -NRˣˣ¹Rˣˣ², donde Rˣˣ¹ y Rˣˣ² se selecciona cada uno independientemente de: arilo, heteroarilo, cicloalquilo, heterocicloalquilo, alquilo C₁₋₆, y alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, arilo, arilo sustituido de 1 a 4 veces con Rˣˣ³, donde Rˣˣ³ se selecciona de: fluoro, cloro, bromo, yodo, alquilo C₁₋₆, alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, -O-alquilo C₁₋₅, y -O-alquilo C₁₋₆ sustituido con 1 a 6 independientemente sustituyentes seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, cicloalquilo, cicloalquilo sustituido de 1 a 4 veces con Rˣˣ⁴, donde Rˣˣ⁴ se selecciona de: fluoro, cloro, bromo, yodo, alquilo C₁₋₆, alquilo C₁₋₆ sustituido con 1 a 6 sustituyentes independientemente seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, -O-alquilo C₁₋₅, y -O-alquilo C₁₋₆ sustituido con 1 a 6 independientemente sustituyentes seleccionados de: fluoro, oxo, -OH, -COOH, -NH₂, y -CN, nitro, y ciano; o una de sus sales farmacéuticamente aceptables. Los compuestos descritos pueden ser útiles en el tratamiento de la distrofia muscular de Duchenne. Composiciones farmacéuticas que comprenden los compuestos descritos y uso de los compuestos para fabricar un medicamento.
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