AR122308A1 - NEW HETEROCYCLIC COMPOUNDS - Google Patents

NEW HETEROCYCLIC COMPOUNDS

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Publication number
AR122308A1
AR122308A1 ARP200102618A ARP200102618A AR122308A1 AR 122308 A1 AR122308 A1 AR 122308A1 AR P200102618 A ARP200102618 A AR P200102618A AR P200102618 A ARP200102618 A AR P200102618A AR 122308 A1 AR122308 A1 AR 122308A1
Authority
AR
Argentina
Prior art keywords
halogen
alkyl
hydrogen
formula
cycloalkyl
Prior art date
Application number
ARP200102618A
Other languages
Spanish (es)
Inventor
Joerg Benz
Luca Gobbi
Uwe Grether
Steven Paul Hanlon
Benoit Hornsperger
Carsten Kroll
Bernd Kuhn
Martin Kuratli
Guofo Liu
Fionn Ohara
Hans Richter
Martin Ritter
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR122308A1 publication Critical patent/AR122308A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

La invención proporciona nuevos compuestos heterocíclicos que presentan la fórmula general (1) en la que A, L, Q, U, V, W, X, Z, m, n y R¹ a R⁴ son tal como se indica en la presente memoria, composiciones que incluyen los compuestos, procedimientos de fabricación de los compuestos y métodos de utilización de los compuestos. Reivindicación 1: Compuesto de fórmula (1) o una sal farmacéuticamente aceptable del mismo, en la que: (i) U es CH₂, V es O, W y X son ambos CH, R¹ se selecciona de halógeno y alquilo C₁₋₆, y R² se selecciona de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², junto con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, o (ii) U es CH₂, V es O, W es CRʷ, X es CH, Rʷ se selecciona de halógeno y alquilo C₁₋₆, R¹ y R² se seleccionan independientemente de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², junto con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, o (iii) U es CH₂, V es O, W y X juntos forman un grupo C=C, y R¹ y R² se seleccionan independientemente de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², junto con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, o (iv) U es CH₂, V se selecciona de NH, CH₂, S, S=O, SO₂, CHOH, CHF y CF₂, (a) W es CRʷ y X es CH, o (b) W y X juntos forman un grupo C=C, Rʷ se selecciona de hidrógeno, halógeno y alquilo C₁₋₆, R¹ y R² se seleccionan independientemente de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², junto con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, o (v) U y V juntos forman un grupo C=C, W y X juntos forman un grupo C=C, y R¹ y R² se seleccionan independientemente de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², junto con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, o (vi) U es CH₂, V es O, W es CH, X es C-OH, y R¹ y R² se seleccionan independientemente de hidrógeno, halógeno y alquilo C₁₋₆, o R¹ y R², juntos con el átomo de carbono al que se encuentran unidos, forman un cicloalquilo C₃₋₁₀, m y son ambos 0, o m y n son ambos 1, Z es CH o N, Q es CRq o N, Rq se selecciona de hidrógeno, halógeno, hidroxi, haloalquilo C₁₋₆ y alquilo C₁₋₆, L se selecciona de un enlace covalente, -CHR⁵-, -O-, -OCH₂-, -CH₂O-, -CH₂OCH₂-, -CF₂CH₂- y -CH₂CF₂-, A se selecciona de arilo C₆₋₁₄, heteroarilo de 5 a 14 elementos y heterociclilo de 3 a 14 elementos, R³ y R⁴ se seleccionados independientemente de hidrógeno, halógeno, SF₅, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, haloalquilo C₁₋₆, haloalcoxi C₁₋₆, arilo C₆₋₁₄, cicloalquilo C₃₋₁₀, heteroarilo de 5 a 14 elementos, ariloxi C₆₋₁₄, cicloalquiloxi C₃₋₁₀ y heteroariloxi de 5 a 14 elementos, en el que dicho arilo C₆₋₁₄, cicloalquilo C₃₋₁₀, heteroarilo de 5 a 14 elementos, ariloxi C₆₋₁₄, cicloalquiloxi C₃₋₁₀ y heteroariloxi de 5 a 14 elementos, y opcionalmente sustituido con 1 a 2 sustituyentes seleccionados de halógeno, alquilo C₁₋₆ y haloalquilo C₁₋₆, y R⁵ se selecciona de hidrógeno y arilo C₆₋₁₄. Reivindicación 22: Procedimiento de fabricación de los compuestos de fórmula (1) según cualquiera de las reivindicaciones 1 a 21, o sales farmacéuticamente aceptables de los mismos, que comprende: (a) hacer reaccionar una amina de fórmula (2), en la que m, n, Q, L, A, R³ y R⁴ son tal como se define en cualquiera de las reivindicaciones 1 a 21, con un ácido carboxílico de fórmula (3a), en el que U, V, W, X, R¹ y R² son tal como se define en cualquiera de las reivindicaciones 1 a 21, en presencia de un reactivo de acoplamiento y opcionalmente en presencia de una base, o (b) hacer reaccionar una amina de fórmula (2), en la que m, n, Q, L, A, R³ y R⁴ son tal como se define en cualquiera de las reivindicaciones 1 a 21, con un cloruro de ácido carboxílico de fórmula (3b), en el que U, V, W, X, R¹ y R² son tal como se define en cualquiera de las reivindicaciones 1 a 21, en presencia de una base, o (c) hacer reaccionar una primera amina de fórmula (4), en la que U, V, W, X, R¹ y R² son tal como se define en cualquiera de las reivindicaciones 1 a 21, con una segunda amina de fórmula (2), en la que A, L, m, n, Q, R³ y R⁴ son tal como se define en cualquiera de las reivindicaciones 1 a 21 en presencia de una base y un reactivo formador de urea, para formar dicho compuesto de fórmula (1).The invention provides new heterocyclic compounds having the general formula (1) in which A, L, Q, U, V, W, X, Z, m, n and R¹ to R⁴ are as indicated herein, compositions including the compounds, methods of making the compounds, and methods of using the compounds. Claim 1: Compound of formula (1) or a pharmaceutically acceptable salt thereof, wherein: (i) U is CH₂, V is O, W and X are both CH, R¹ is selected from halogen and C₁₋₆ alkyl, and R² is selected from hydrogen, halogen, and C₁₋₆ alkyl, or R¹ and R², together with the carbon atom to which they are attached, form a C₃₋₁₀ cycloalkyl, or (ii) U is CH₂, V is O, W is CRʷ, X is CH, Rʷ is selected from halogen and C₁₋₆ alkyl, R¹ and R² are independently selected from hydrogen, halogen and C₁₋₆ alkyl, or R¹ and R², together with the carbon atom to which they are located together, they form a C₃₋₁₀ cycloalkyl, or (iii) U is CH₂, V is O, W and X together form a C=C group, and R¹ and R² are independently selected from hydrogen, halogen, and C₁₋₆ alkyl, or R¹ and R², together with the carbon atom to which they are attached, form a C₃₋₁₀ cycloalkyl, or (iv) U is CH₂, V is selected from NH, CH₂, S, S=O, SO₂, CHOH, CHF and CF₂, (a) W is CRʷ and X is CH, or (b) W and X together form a C=C group, Rʷ is selected from hydrogen, halogen, and C₁₋₆ alkyl, R¹ and R² are independently selected from hydrogen, halogen, and C₁₋₆ alkyl, or R¹ and R², together with the carbon atom to which they are attached, form a C₃ cycloalkyl ₋₁₀, or (v) U and V together form a C=C group, W and X together form a C=C group, and R¹ and R² are independently selected from hydrogen, halogen, and C₁₋₆ alkyl, or R¹ and R² , together with the carbon atom to which they are attached, form a C₃₋₁₀ cycloalkyl, or (vi) U is CH₂, V is O, W is CH, X is C-OH, and R¹ and R² are independently selected from hydrogen, halogen, and C₁₋₆ alkyl, or R¹ and R², together with the carbon atom to which they are attached, form a C₃₋₁₀ cycloalkyl, m and are both 0, or m and n are both 1, Z is CH or N, Q is CRq or N, Rq is selected from hydrogen, halogen, hydroxy, C₁₋₆ haloalkyl and C₁₋₆ alkyl, L is selected from a covalent bond, -CHR⁵-, -O-, -OCH₂-, -CH₂O-, - CH₂OCH₂-, -CF₂CH₂- and -CH₂CF₂-, A is selected from C₆₋ aryl ₁₄, 5-14 membered heteroaryl and 3-14 membered heterocyclyl, R³ and R⁴ are independently selected from hydrogen, halogen, SF₅, cyano, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkyl, C₁₋₆ haloalkoxy , C₆₋₁₄-aryl, C₃₋₁₀-cycloalkyl, 5-14 membered heteroaryl, C₆₋₁₄-aryloxy, C₃₋₁₀-cycloalkyloxy and 5-14-membered heteroaryloxy, wherein said C₆₋₁₄ aryl, C₃₋ cycloalkyl, heteroaryl 5 to 14 membered, C₆₋₁₄ aryloxy, C₃₋₁₀ cycloalkyloxy, and 5 to 14 membered heteroaryloxy, and optionally substituted with 1 to 2 substituents selected from halogen, C₁₋₆ alkyl, and C₁₋₆ haloalkyl, and R⁵ is selected from hydrogen and C₆₋₁₄ aryl. Claim 22: Process for manufacturing the compounds of formula (1) according to any of claims 1 to 21, or pharmaceutically acceptable salts thereof, comprising: (a) reacting an amine of formula (2), in which m, n, Q, L, A, R³ and R⁴ are as defined in any of claims 1 to 21, with a carboxylic acid of formula (3a), in which U, V, W, X, R¹ and R² are as defined in any one of claims 1 to 21, in the presence of a coupling reagent and optionally in the presence of a base, or (b) reacting an amine of formula (2), where m, n , Q, L, A, R³ and R⁴ are as defined in any one of claims 1 to 21, with a carboxylic acid chloride of formula (3b), in which U, V, W, X, R¹ and R² are as defined in any one of claims 1 to 21, in the presence of a base, or (c) reacting a first amine of formula (4), wherein U, V, W, X, R¹ and R² are such as or is defined in any of claims 1 to 21, with a second amine of formula (2), in which A, L, m, n, Q, R³ and R⁴ are as defined in any of claims 1 to 21 in the presence of a base and a urea-forming reagent, to form said compound of formula (1).

ARP200102618A 2019-09-23 2020-09-21 NEW HETEROCYCLIC COMPOUNDS AR122308A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19198974 2019-09-23

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AR122308A1 true AR122308A1 (en) 2022-08-31

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