AR108535A1 - Derivados de tetrahidropirano y tiopirano que tienen actividad multimodal contra el dolor - Google Patents

Derivados de tetrahidropirano y tiopirano que tienen actividad multimodal contra el dolor

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AR108535A1
AR108535A1 ARP170101361A ARP170101361A AR108535A1 AR 108535 A1 AR108535 A1 AR 108535A1 AR P170101361 A ARP170101361 A AR P170101361A AR P170101361 A ARP170101361 A AR P170101361A AR 108535 A1 AR108535 A1 AR 108535A1
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Esteve Labor Dr
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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
    • C07D405/04—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 directly linked by a ring-member-to-ring-member bond
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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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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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
    • A61K31/495—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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen 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 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen 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
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen 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 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • 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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    • C07D405/14—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 three or more hetero rings
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Pain & Pain Management (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
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  • Nitrogen Condensed Heterocyclic Rings (AREA)
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Abstract

La presente solicitud se refiere a derivados de tetrahidropirano y tiopirano que presentan actividad farmacológica dual contra tanto el receptor sigma (s), como el receptor de opioides m, a procedimientos de preparación de tales compuestos, a composiciones farmacéuticas que los comprenden, y a su uso en terapia, en particular para el tratamiento del dolor. Reivindicación 1: Compuesto de fórmula general (1), donde R¹ es un compuesto de fórmula (2) ó (3); m es 1, 2 ó 3; n es 0, 1 ó 2; p es 0, 1 ó 2; q es 0 ó 1; W es nitrógeno o carbono; X es un enlace, -C(RˣRˣ’)-, C=O u -O-; donde Rˣ se selecciona entre halógeno, -OR⁷, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; Rˣ’ se selecciona entre hidrógeno, halógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; R⁷ se selecciona entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; Y es -S- u -O-; R¹’ se selecciona entre alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido, alquinilo C₂₋₆ no sustituido o sustituido, cicloalquilo no sustituido o sustituido, arilo no sustituido o sustituido y heterociclilo no sustituido o sustituido; donde dicho cicloalquilo, arilo o heterociclilo en R¹’ si está sustituido, está sustituido con uno o más sustituyentes seleccionados entre halógeno, -R¹¹, -OR¹¹, -NO₂, -NR¹¹R¹¹’’’, NR¹¹C(O)R¹¹’, -NR¹¹S(O)₂R¹¹’, -S(O)₂NR¹¹R¹¹’, -NR¹¹C(O)NR¹¹’R¹¹’’, -SR¹¹, -S(O)R¹¹, S(O)₂R¹¹, -CN, haloalquilo, haloalcoxilo, -C(O)OR¹¹, -C(O)NR¹¹R¹¹’, -OCH₂CH₂OH, -NR¹¹S(O)₂NR¹¹’R¹¹’’ y C(CH₃)₂OR¹¹; adicionalmente, el cicloalquilo o heterociclilo no aromático en R¹’, si está sustituido, también puede estar sustituido con un resto de fórmula (4) u =O; donde el alquilo, alquenilo o alquinilo en R¹’, si está sustituido, está sustituido con uno o más sustituyentes seleccionados entre -OR¹¹, halógeno, -CN, haloalquilo, haloalcoxilo, -SR¹¹, -S(O)R¹¹, y -S(O)₂R¹¹; donde R¹¹, R¹¹’ y R¹¹’’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido y alquinilo C₂₋₆ no sustituido; y donde R¹¹’’’ se selecciona entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido, alquinilo C₂₋₆ no sustituido y -Boc; R² se selecciona entre alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido, alquinilo C₂₋₆ no sustituido o sustituido, cicloalquilo no sustituido o sustituido, arilo no sustituido o sustituido y heterociclilo no sustituido o sustituido; donde dicho cicloalquilo, arilo o heterociclilo aromático en R², si está sustituido, se sustituye con uno o más sustituyentes seleccionados entre halógeno, -R¹², -OR¹², -NO₂, -NR¹²R¹²’’’, NR¹²C(O)R¹²’, -NR¹²S(O)₂R¹²’, -S(O)₂NR¹²R¹²’, -NR¹²C(O)NR¹²’R¹²’’, -SR¹², -S(O)R¹², -S(O)₂R¹², -CN, haloalquilo, haloalcoxilo, -C(O)OR¹², -C(O)NR¹²R¹²’, -OCH₂CH₂OH, -NR¹²S(O)₂NR¹²’R¹²’’ y C(CH₃)₂OR¹²; adicionalmente, el cicloalquilo o heterociclilo no aromático en R², si está sustituido, también puede estar sustituido con un resto de fórmula (4) u =O; donde el alquilo, alquenilo o alquinilo en R², si está sustituido, está sustituido con uno o más sustituyentes seleccionados entre -OR¹², halógeno, -CN, haloalquilo, haloalcoxilo, -SR¹², -S(O)R¹² y -S(O)₂R¹²; donde R¹², R¹²’ y R¹²’’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido y alquinilo C₂₋₆ no sustituido; y donde R¹²’’’ se selecciona entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido, alquinilo C₂₋₆ no sustituido y -Boc; R³ y R³’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; R⁴ y R⁴’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido, alternativamente, R⁴ y R⁴’, pueden formar junto con el átomo de carbono al que están unidos un cicloalquilo sustituido o no sustituido; R⁴’’ y R⁴’’’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido, alternativamente, R⁴’’ y R⁴’’’, pueden formar junto con el átomo de carbono al que están unidos un cicloalquilo no sustituido o sustituido; R⁵ y R⁵’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido, alquinilo C₂₋₆ no sustituido o sustituido, -CHOR⁸ y -C(O)OR⁸; donde R⁸ se selecciona entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; R⁶ y R⁶’ se seleccionan independientemente entre hidrógeno, -OR⁹, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; donde R⁹ y R⁹’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido o sustituido, alquenilo C₂₋₆ no sustituido o sustituido y alquinilo C₂₋₆ no sustituido o sustituido; y donde el resto de fórmula (5) se selecciona entre los compuestos del grupo de fórmulas (6), donde Rⁿ se selecciona entre alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido y alquinilo C₂₋₆ no sustituido; el alquilo, alquenilo o alquinilo, distintos de los definidos en R¹’ o R², si está sustituido, está sustituido con uno o más sustituyentes seleccionados entre -OR¹³, halógeno, -CN, haloalquilo, haloalcoxilo, -SR¹³, -S(O)R¹³ y -S(O)₂R¹³; donde R¹³ y R¹³’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido y alquinilo C₂₋₆ no sustituido; el arilo, heterociclilo o cicloalquilo distintos de los definidos en R¹’ o R², si está sustituido, está sustituido con uno o más sustituyentes seleccionados entre halógeno, -R¹⁴, -OR¹⁴, -NO₂, -NR¹⁴R¹⁴’’’, NR¹⁴C(O)R¹⁴’, -NR¹⁴S(O)₂R¹⁴’, -S(O)₂NR¹⁴R¹⁴’, -NR¹⁴C(O)NR¹⁴’R¹⁴’’, -SR¹⁴, -S(O)R¹⁴, S(O)₂R¹⁴, -CN, haloalquilo, haloalcoxilo, -C(O)OR¹⁴, -C(O)NR¹⁴R¹⁴’, -OCH₂CH₂OH, -NR¹⁴S(O)₂NR¹⁴’R¹⁴’’ y C(CH₃)₂OR¹⁴; adicionalmente, donde el cicloalquilo o heterociclilo no aromático, distintos de los definidos en R¹’ o R², si está sustituido, también puede estar sustituido con un resto de fórmula (4) u =O; donde R¹⁴, R¹⁴’ y R¹⁴’’ se seleccionan independientemente entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido, alquinilo C₂₋₆ no sustituido, arilo no sustituido, cicloalquilo no sustituido y heterociclilo no sustituido; y donde R¹⁴’’’ se selecciona entre hidrógeno, alquilo C₁₋₆ no sustituido, alquenilo C₂₋₆ no sustituido, alquinilo C₂₋₆ no sustituido y -Boc; opcionalmente en forma de uno de los estereoisómeros, preferiblemente enantiómeros o diastereómeros, un racemato o en forma de una mezcla de al menos dos de los estereoisómeros, preferiblemente enantiómeros y/o diastereómeros, en cualquier razón de mezclado, o una de sus sales correspondientes, o uno de sus solvatos correspondientes; se excluye el compuesto de fórmula (7); y se excluye el compuesto de fórmula (8).
ARP170101361A 2016-05-20 2017-05-19 Derivados de tetrahidropirano y tiopirano que tienen actividad multimodal contra el dolor AR108535A1 (es)

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