AR113910A1 - DERIVATIVES OF O-PHENOXY AND O-BENZYLOXYPROPYLAMINE WITH ACTIVITY AGAINST PAIN - Google Patents

DERIVATIVES OF O-PHENOXY AND O-BENZYLOXYPROPYLAMINE WITH ACTIVITY AGAINST PAIN

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AR113910A1
AR113910A1 ARP180103530A ARP180103530A AR113910A1 AR 113910 A1 AR113910 A1 AR 113910A1 AR P180103530 A ARP180103530 A AR P180103530A AR P180103530 A ARP180103530 A AR P180103530A AR 113910 A1 AR113910 A1 AR 113910A1
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substituted
unsubstituted
hydrogen
alkynyl
alkyl
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ARP180103530A
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Esteve Pharmaceuticals Sa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—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
    • C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D405/04—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

La presente se refiere a derivados de o-fenoxi y o-benciloxipropilamino que tienen actividad farmacológica hacia la subunidad a2d, en particular la subunidad a2d-1, del canal de calcio dependiente del voltaje, a procesos de preparación de tales compuestos, a composiciones farmacéuticas que los comprenden, y a su uso en la terapia, en particular para el tratamiento del dolor. Reivindicación 1: Un compuesto de fórmula general (1), en donde X se selecciona de un enlace, -[C(RᵃRᵇ)]ₚ-, -[CH₂]ₚC(O)[CH₂]q-, -[CH₂]ₚC(O)N(Rᶻ)[CH₂]q-, -[CH₂]ₚN(Rᶻ)C(O)[CH₂]q- y -[CH₂]ₚN(Rᶻ)[CH₂]q-; Rᵃ se selecciona de hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; Rᵇ se selecciona de hidrógeno, halógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, Rᵃ y Rᵇ, tomados junto con el átomo de carbono al cual están unidos, pueden formar un cicloalquilo sustituido o no sustituido; Rᶻ se selecciona de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, cicloalquilo sustituido o no sustituido, alquilcicloalquilo sustituido o no sustituido y -C(O)-alquilo C₁₋₆; p es 0, 1, 2, 3, 4 ó 5; q es 0, 1, 2, 3, 4 ó 5; Y¹ es -C(R¹⁰R¹⁰’)-; en donde R¹⁰ y R¹⁰’ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, R¹⁰ y R¹⁰’ pueden formar, junto con el átomo de carbono al cual están unidos, un cicloalquilo sustituido o no sustituido; Y² es -C(R¹⁰’’R¹⁰’’’)-; en donde R¹⁰’’ y R¹⁰’’’ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; alternativamente, R¹⁰’’ y R¹⁰’’’ pueden formar, junto con el átomo de carbono al cual están unidos, un cicloalquilo sustituido o no sustituido; n es 0 ó 1; R¹ se selecciona de -NR⁵R⁵’ y -NR⁵’C(O)R⁵; R² se selecciona de arilo sustituido o no sustituido y heterociclilo sustituido o no sustituido; R³ se selecciona de alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, alquinilo C₂₋₆ sustituido o no sustituido, cicloalquilo sustituido o no sustituido y alquilcicloalquilo sustituido o no sustituido; R³’ se selecciona de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; R⁴ y R⁴’ se seleccionan independientemente de halógeno, -R⁴¹, -OR⁴¹, -NO₂, -NR⁴¹R⁴¹’, -NR⁴¹C(O)R⁴¹’, -NR⁴¹S(O)₂R⁴¹’, -S(O)₂NR⁴¹R⁴¹’, -NR⁴¹C(O)NR⁴¹’R⁴¹’’, -SR⁴¹, -S(O)R⁴¹, -S(O)₂R⁴¹, -CN, haloalquilo, haloalcoxi, -C(O)OR⁴¹, -C(O)NR⁴¹R⁴¹’, -OCH₂CH₂OR⁴¹, -NR⁴¹S(O)₂NR⁴¹’R⁴¹’’ y -C(CH₃)₂OR⁴¹; en donde R⁴¹, R⁴¹’ y R⁴¹’’ se seleccionan independientemente de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; R⁵ se selecciona de alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido, y alquinilo C₂₋₆ sustituido o no sustituido, cicloalquilo sustituido o no sustituido, arilo sustituido o no sustituido, heteroarilo sustituido o no sustituido, alquilcicloalquilo sustituido o no sustituido, alquilarilo sustituido o no sustituido y alquilheteroarilo sustituido o no sustituido; R⁵’ se selecciona de hidrógeno, alquilo C₁₋₆ sustituido o no sustituido, alquenilo C₂₋₆ sustituido o no sustituido y alquinilo C₂₋₆ sustituido o no sustituido; 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 proporción de mezcla, o una sal correspondiente de los mismos, o un solvato correspondiente de los mismos; los compuestos de fórmula (2) y (3) están adicionalmente excluidos.This refers to derivatives of o-phenoxy and o-benzyloxypropylamino having pharmacological activity towards the a2d subunit, in particular the a2d-1 subunit, of the voltage-gated calcium channel, to processes for the preparation of such compounds, to pharmaceutical compositions who understand them, and their use in therapy, particularly for pain management. Claim 1: A compound of general formula (1), wherein X is selected from a bond, - [C (RᵃRᵇ)] ₚ-, - [CH₂] ₚC (O) [CH₂] q-, - [CH₂] ₚC (O) N (Rᶻ) [CH₂] q-, - [CH₂] ₚN (Rᶻ) C (O) [CH₂] q- and - [CH₂] ₚN (Rᶻ) [CH₂] q-; Rᵃ is selected from hydrogen, halogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; Rᵇ is selected from hydrogen, halogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; alternatively, Rᵃ and Rᵇ, taken together with the carbon atom to which they are attached, may form a substituted or unsubstituted cycloalkyl; Rᶻ is selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, C₂₋₆ substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkylcycloalkyl, and -C (O) -C₁₋₆ alkyl; p is 0, 1, 2, 3, 4, or 5; q is 0, 1, 2, 3, 4, or 5; Y¹ is -C (R¹⁰R¹⁰ ') -; wherein R¹⁰ and R¹⁰ 'are independently selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; alternatively, R¹⁰ and R¹⁰ 'may form, together with the carbon atom to which they are attached, a substituted or unsubstituted cycloalkyl; Y² is -C (R¹⁰’’R¹⁰ ’’ ’) -; wherein R¹⁰ ’’ and R¹⁰ ’’ ’are independently selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; alternatively, R¹⁰ '' and R¹⁰ '' 'may form, together with the carbon atom to which they are attached, a substituted or unsubstituted cycloalkyl; n is 0 or 1; R¹ is selected from -NR⁵R⁵ 'and -NR⁵'C (O) R⁵; R² is selected from substituted or unsubstituted aryl and substituted or unsubstituted heterocyclyl; R³ is selected from C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, C₂₋₆ substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted alkylcycloalkyl; R³ 'is selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; R⁴ and R⁴ 'are independently selected from halogen, -R⁴¹, -OR⁴¹, -NO₂, -NR⁴¹R⁴¹', -NR⁴¹C (O) R⁴¹ ', -NR⁴¹S (O) ₂R⁴¹', -S (O) ₂NR⁴¹R⁴¹ ', -NR⁴¹C ( O) NR⁴¹'R⁴¹ '', -SR⁴¹, -S (O) R⁴¹, -S (O) ₂R⁴¹, -CN, haloalkyl, haloalkoxy, -C (O) OR⁴¹, -C (O) NR⁴¹R⁴¹ ', -OCH₂CH₂OR⁴¹, -NR⁴¹S (O) ₂NR⁴¹'R⁴¹ '' and -C (CH₃) ₂OR⁴¹; wherein R⁴¹, R⁴¹ 'and R⁴¹' 'are independently selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; R⁵ is selected from C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkylcycloalkyl, substituted or unsubstituted alkylaryl, and substituted or unsubstituted alkylheteroaryl; R⁵ 'is selected from hydrogen, C₁₋₆ substituted or unsubstituted alkyl, C₂₋₆ substituted or unsubstituted alkenyl, and C₂₋₆ substituted or unsubstituted alkynyl; optionally in the form of one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or in the form of a mixture of at least two of the stereoisomers, preferably enantiomers and / or diastereomers, in any mixing ratio, or a corresponding salt thereof , or a corresponding solvate thereof; compounds of formula (2) and (3) are further excluded.

ARP180103530A 2017-12-04 2018-12-03 DERIVATIVES OF O-PHENOXY AND O-BENZYLOXYPROPYLAMINE WITH ACTIVITY AGAINST PAIN AR113910A1 (en)

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JP2022551156A (en) * 2019-10-10 2022-12-07 エステベ ファーマシューティカルズ，ソシエダッド アノニマ Homopiperazinyl and homopiperidinylquinazolin-4(3H)-one derivatives with diverse activities against pain

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US5320825A (en) * 1991-05-01 1994-06-14 Trustees Of The University Of Pennsylvania Serotonin reuptake inhibitors for S.P.E.C.T. imaging
SI3452475T1 (en) * 2016-05-06 2020-07-31 Esteve Pharmaceuticals, S.A. Tetrahydropyrimidodiazepine and tetrahydropyridodiazepine compounds for treating pain and pain related conditions

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