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AR124008A1 - 1,4-diazepanonas bicíclicas y sus usos terapéuticos - Google Patents

1,4-diazepanonas bicíclicas y sus usos terapéuticos

Info

Publication number
AR124008A1
AR124008A1 ARP210103079A ARP210103079A AR124008A1 AR 124008 A1 AR124008 A1 AR 124008A1 AR P210103079 A ARP210103079 A AR P210103079A AR P210103079 A ARP210103079 A AR P210103079A AR 124008 A1 AR124008 A1 AR 124008A1
Authority
AR
Argentina
Prior art keywords
alkyl
optionally substituted
membered heterocyclyl
12alkyl
cycloalkyl
Prior art date
Application number
ARP210103079A
Other languages
English (en)
Inventor
Bradley P Morgan
Chris Evans
Pu Lu
- Yamasaki Makoto Ping
Wenyue Wang
Scott Collibee
Takuya Makino
Kazuyuki Tsuchiya
Toshio Kurosaki
Susumu Yamaki
Eriko Honjo
Yuka Koizumi
Naoto Katoh
Ryuichi Sekioka
Ikumi Kuriwaki
Denise Andersen
Original Assignee
Cytokinetics Inc
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 Cytokinetics Inc filed Critical Cytokinetics Inc
Publication of AR124008A1 publication Critical patent/AR124008A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • A—HUMAN NECESSITIES
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A—HUMAN NECESSITIES
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen atoms
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    • 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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Abstract

En la presente se proporcionan compuestos de la fórmula (1), o un estereoisómero o tautómero de estos, o una sal farmacéuticamente aceptable de cualquiera de los que anteceden, donde X¹, X², Rʸ, Rᶻ, R¹, R², R³, y R4 son tal como se definen en la presente. También se proporciona en la presente una composición farmacéuticamente aceptable que comprende un compuesto de la fórmula (1), o un estereoisómero o tautómero de este, o una sal farmacéuticamente aceptable de cualquiera de los que anteceden. También se proporcionan en la presente métodos para usar un compuesto de la fórmula (1), o un estereoisómero o tautómero de este, o una sal farmacéuticamente aceptable de cualquiera de los que anteceden, para tratar varias enfermedades, trastornos y afecciones que responden a la modulación de la contractilidad del sarcómero esquelético. Reivindicación 1: Un compuesto de la fórmula (1), o una sal, estereoisómero o tautómero farmacéuticamente aceptable de este, donde: X¹ y X² son cada uno independientemente N o C-Rˣ; cada Rˣ, Rʸ y Rᶻ es independientemente H, halo, cicloalquilo C₃₋₁₀, cicloalquenilo C₃₋₁₀ o arilo C₆₋₂₀; R¹ es alquilo C₃₋₁₂, alquenilo C₂₋₁₂, alquinilo C₂₋₁₂, cicloalquilo C₃₋₁₀, cicloalquenilo C₃₋₁₀ o un resto de fórmula (2), donde Rʷ es alquilo C₁₋₁₂ opcionalmente sustituido; R² es: a) C(O)-Rʰ, donde Rʰ es (i) amino opcionalmente sustituido, alcoxi C₁₋₃ opcionalmente sustituido, -C(O)NH₂ opcionalmente sustituido, cicloalquilo C₃₋₁₀ opcionalmente sustituido, cicloalquenilo C₃₋₁₀ opcionalmente sustituido, arilo C₆₋₂₀ opcionalmente sustituido, heterociclilo de 3 - 15 miembros opcionalmente sustituido, o heteroarilo de 5 - 20 miembros opcionalmente sustituido, o (ii) alquilo C₁₋₁₂, donde el alquilo C₁₋₁₂ está no sustituido o está sustituido con uno o más de Rⁿ, donde Rⁿ es OH, oxo, halo, ciano, -C(O)NH₂, amino opcionalmente sustituido, sulfonilo opcionalmente sustituido, alcoxi C₁₋₁₂ opcionalmente sustituido, ariloxi C₆₋₂₀ opcionalmente sustituido, cicloalquilo C₃₋₁₀ opcionalmente sustituido, cicloalquenilo C₃₋₁₀ opcionalmente sustituido, heterociclilo de 3 - 15 miembros opcionalmente sustituido o heteroarilo de 5 - 20 miembros opcionalmente sustituido, o b) alquilo C₁₋₁₂, donde el alquilo C₁₋₁₂ está no sustituido o está sustituido con uno o más de Rᵐ, donde Rᵐ es OH, halo, ciano, oxo, alquilo C₁₋₁₂, alcoxi C₁₋₁₂, ariloxi C₆₋₂₀, -C(O)NH₂, -C(O)NH(alquilo C₁₋₁₂), -C(O)N(alquilo C₁₋₁₂)₂, -C(O)OH, -C(O)-alcoxi C₁₋₁₂,-C(O)-(heterociclilo de 3 - 15 miembros), NH₂, -NH(alquilo C₁₋₁₂), -N(alquilo C₁₋₁₂)₂, -NHC(O)-alquilo C₁₋₁₂, -NHC(O)-NH₂, -NH-SO₂-alquilo C₁₋₁₂, -S(O)-alquilo C₁₋₁₂, -S(O)₂-alquilo C₁₋₁₂, -S(O)₂-NH₂, cicloalquilo C₃₋₁₀, o heterociclilo de 3 - 15 miembros, donde el alquilo C₁₋₁₂, alcoxi C₁₋₁₂, ariloxi C₆₋₂₀, el alquilo C₁₋₁₂ de -C(O)NH(alquilo C₁₋₁₂), el alquilo C₁₋₁₂ de -C(O)N(alquilo C₁₋₁₂)₂, -C(O)OH, -C(O)-alcoxi C₁₋₁₂, el heterociclilo de 3 - 15 miembros de -C(O)-(heterociclilo de 3 - 15 miembros), NH₂, el alquilo C₁₋₁₂ de -NH(alquilo C₁₋₁₂), el alquilo C₁₋₁₂ de -N(alquilo C₁₋₁₂)₂, el alquilo C₁₋₁₂ de -NHC(O)-alquilo C₁₋₁₂, -NHC(O)-NH₂, el alquilo C₁₋₁₂ de -NH-SO₂-alquilo C₁₋₁₂, el alquilo C₁₋₁₂ de -S(O)-alquilo C₁₋₁₂, el alquilo C₁₋₁₂ de -S(O)₂-alquilo C₁₋₁₂, -S(O)₂-NH₂, cicloalquilo C₃₋₁₀, o heterociclilo de 3 - 15 miembros de Rᵐ está opcionalmente sustituido adicionalmente por uno o más de OH, halo, ciano, oxo, alquilo C₁₋₁₂, alcoxi C₁₋₁₂, -C(O)NH₂, -C(O)NH(alquilo C₁₋₁₂), -C(O)N(alquilo C₁₋₁₂)₂, C(O)OH, NH₂, -NH(alquilo C₁₋₁₂), -N(alquilo C₁₋₁₂)₂, cicloalquilo C₃₋₁₀, arilo C₆₋₂₀, heterociclilo de 3 - 15 miembros o heteroarilo de 5 - 20 miembros, o c) cicloalquenilo C₃₋₁₀ opcionalmente sustituido, o d) heteroarilo de 5 - 20 miembros opcionalmente sustituido, o e) heterociclilo de 3 - 15 miembros opcionalmente sustituido, o f) amidinilo opcionalmente sustituido, o g) sulfonilo opcionalmente sustituido, o h) ciano, y R³ es H, alquilo C₁₋₁₂ opcionalmente sustituido, -C(O)NH₂ opcionalmente sustituido, o alcoxi opcionalmente sustituido -C(O)-C₁₋₁₂; o R² y R³ se toman junto con los átomos a los que están unidos para formar un heterociclilo de 5 ó 6 miembros o heteroarilo de 5 ó 6 miembros, donde el heterociclilo de 5 ó 6 miembros o heteroarilo de 5 ó 6 miembros independientemente comprende dos o más heteroátomos anulares y está opcionalmente sustituido independientemente; y R⁴ está ausente o es H, alquilo C₁₋₁₂ opcionalmente sustituido, -C(O)NH₂ opcionalmente sustituido, o alcoxi opcionalmente sustituido -C(O)-C₁₋₁₂. Reivindicación 39: Un compuesto que se selecciona del grupo que consiste en: grupo de fórmula (3) o una sal farmacéuticamente aceptable de este. Reivindicación 43: Una forma cristalina del Compuesto (10) caracterizada por tener un patrón de XRPD que comprende picos en los ángulos 2-theta de los grados 8,26 ± 0,2, 16,47 ± 0,2, 24,36 ± 0,2 y 24,75 ± 0,2. Reivindicación 47: Una forma cristalina del Compuesto (10) caracterizada por tener un patrón de XRPD que comprende picos en los ángulos 2-theta de los grados 10,16 ± 0,2, 13,86 ± 0,2, 16,60 ± 0,2 y 19,54 ± 0,2.
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