AR044676A1 - Pirrolidinas y piperidinas sustituidas, compuestos relacionados, procedimientos para su preparacion y composiciones farmaceuticas que los contienen. - Google Patents

Pirrolidinas y piperidinas sustituidas, compuestos relacionados, procedimientos para su preparacion y composiciones farmaceuticas que los contienen.

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Publication number
AR044676A1
AR044676A1 ARP040102027A ARP040102027A AR044676A1 AR 044676 A1 AR044676 A1 AR 044676A1 AR P040102027 A ARP040102027 A AR P040102027A AR P040102027 A ARP040102027 A AR P040102027A AR 044676 A1 AR044676 A1 AR 044676A1
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AR
Argentina
Prior art keywords
alkyl
cycloalkyl
independently selected
heteroaryl
alkenyl
Prior art date
Application number
ARP040102027A
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English (en)
Inventor
Mathai Mammen
Adam Hughes
Weijiang Zhang
Yu-Hua Ji
Li Li
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Theravance Inc
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Publication date
Application filed by Theravance Inc filed Critical Theravance Inc
Publication of AR044676A1 publication Critical patent/AR044676A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La presente se refiere a pirrolidinas y piperidinas sustituidas, también tiene como objeto composiciones farmacéuticas que contienen dichos compuestos; procesos e intermediarios de utilidad en la preparación de dichos compuestos, y métodos para tratar estados de enfermedad mediados por receptores muscarínicos utilizando dichos compuestos. Reivindicación 1: Un compuesto de fórmula (1) donde cada R1 y R2 se selecciona en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C3-6 cicloalquilo, ciano, halo, ORa, SRa, S(O)Ra, S(O)2Ra y NRbRc, o dos grupos R1 adyacentes o dos grupos R2 adyacentes se unen para formar C3-6 alquileno, (C2-4 alquilen)O ó O(C1-4 alquilen)O; cada R3 se selecciona en forma independiente entre C1-4 alquilo y F; cada R4 se selecciona en forma independiente entre H, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo, C3-6 heterociclilo, CH2R6 y CH2CH2R7; o ambos grupos R4 se unen junto al átomo de N al cual están unidos para formar C3-6 heterociclilo; R5 se selecciona entre C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, y CH2R8, donde cada grupo alquilo, alquenilo y alquinilo está opcionalmente sustituido con OH o entre 1 y 5 sustituyentes F; cada R6 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo y C3-6 heterociclilo; cada R7 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo, C3-6 heterociclilo, OH, O(C1-6 alquilo), O(C3-6 cicloalquilo), O(C6-10 arilo), O(C2-9 heteroarilo), S(C1-6 alquilo), S(O)(C1-6 alquilo), S(O)2(C1-6 alquilo), S(C3-6 cicloalquilo), S(O)(C3-6 cicloalquilo), S(O)2(C3-6 cicloalquilo), S(C6-10 arilo), S(O)(C6-10 arilo), S(O)2(C6-10 arilo), S(C2-9 heteroarilo), S(O)(C2-9 heteroarilo) y S(O)2(C2-9 heteroarilo); cada R8 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo y C3-6 heterociclilo; cada Ra se selecciona en forma independiente entre H, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo y C3-6 cicloalquilo; cada Rb y Rc se selecciona en forma independiente entre H, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, y C3-6 cicloalquilo; o Rb y Rc se unen junto al átomo de N al cual están unidos para formar C3-6 heterociclilo; a es un entero entre 0 y 3; b es un entero entre 0 y 3; c es un entero entre 0 y 4; d es 1 o 2; e es 8 o 9; donde cada grupo alquilo, alquileno, alquenilo, alquinilo y cicloalquilo en R1, R2, R3, R4, R7, Ra, Rb y Rc está opcionalmente sustituido con entre 1 y 5 sustituyentes F; cada grupo arilo, cicloalquilo, heteroarilo y heterociclilo en R1, R2, R4, R5, R6, R7, R8, Ra, Rb y Rc está opcionalmente sustituido con entre 1 y 3 sustituyentes seleccionados en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, ciano, halo, O(C1-4 alquilo), S(C1-4 alquilo), S(O)(C1-4 alquilo), S(O)2(C1-4 alquilo), NH2, NH(C1-4 alquilo) y N(C1-4 alquilo)2, donde cada grupo alquilo, alquileno, alquenilo y alquinilo está opcionalmente sustituido con entre 1 y 5 sustituyentes F, y cada grupo CH2 en (CH2)e está opcionalmente sustituido con 1 o 2 sustituyentes seleccionados en forma independiente entre C1-2 alquilo, OH y F; o una sal, un solvato o un estereoisómero aceptable para uso farmacéutico del mismo. Reivindicación 34: Un proceso para preparar un compuesto de fórmula (1) donde cada R1 y R2 se selecciona en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, C3-6 cicloalquilo, ciano, halo, ORa, SRa, S(O)Ra, S(O)2Ra y NRbRc, o dos grupos R1 adyacentes o dos grupos R2 adyacentes se unen para formar C3-6 alquileno, (C2-4 alquilen)O ó O(C1-4 alquilen)O; cada R3 se selecciona en forma independiente entre C1-4 alquilo y F; cada R4 se selecciona en forma independiente entre H, C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo, C3-6 heterociclilo, CH2R6 y CH2CH2R7; o ambos grupos R4 se unen junto al átomo de N al cual están unidos para formar C3-6 heterociclilo; R5 se selecciona entre C1-6 alquilo, C2-6 alquenilo, C2-6 alquinilo, C3-6 cicloalquilo, y CH2R8, donde cada grupo alquilo, alquenilo y alquinilo está opcionalmente sustituido con OH o entre 1 y 5 sustituyentes F; cada R6 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo y C3-6 heterociclilo; cada R7 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo, C3-6 heterociclilo, OH, O(C1-6 alquilo), O(C3-6 cicloalquilo), O(C6-10 arilo), O(C2-9 heteroarilo), S(C1-6 alquilo), S(O)(C1-6alquilo), S(O)2(C1-6 alquilo), S(C3-6 cicloalquilo), S(O)(C3-6 cicloalquilo), S(O)2(C3-6 cicloalquilo), S(C6-10 arilo), S(O)(C6-10 arilo), S(O)2(C6-10 arilo), S(C2-9 heteroarilo), S(O)(C2-9 heteroarilo) y S(O)2(C2-9 heteroarilo); cada R8 se selecciona en forma independiente entre C3-6 cicloalquilo, C6-10 arilo, C2-9 heteroarilo y C3-6 heterociclilo; cada Ra se selecciona en forma independiente entre H, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo y C3-6 cicloalquilo; cada Rb y Rc se selecciona en forma independiente entre H, C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, y C3-6 cicloalquilo; o Rb y Rc se unen junto al átomo de N al cual están unidos para formar C3-6 heterociclilo; a es un entero entre 0 y 3; b es un entero entre 0 y 3; c es un entero entre 0 y 4; d es 1 o 2; e es 8 o 9; donde cada grupo alquilo, alquileno, alquenilo, alquinilo y cicloalquilo en R1, R2, R3, R4, R7, Ra, Rb y Rc está opcionalmente sustituido con entre 1 y 5 sustituyentes F; cada grupo arilo, cicloalquilo, heteroarilo y heterociclilo en R1, R2, R4, R5, R6, R7, R8, Ra, Rb y Rc está opcionalmente sustituido con entre 1 y 3 sustituyentes seleccionados en forma independiente entre C1-4 alquilo, C2-4 alquenilo, C2-4 alquinilo, ciano, halo, O(C1-4 alquilo), S(C1-4 alquilo), S(O)(C1-4 alquilo), S(O)2(C1-4 alquilo), NH2, NH(C1-4 alquilo) y N(C1-4 alquilo)2, donde cada grupo alquilo, alquileno, alquenilo y alquinilo está opcionalmente sustituido con entre 1 y 5 sustituyentes F, y cada grupo CH2 en (CH2)e está opcionalmente sustituido con 1 o 2 sustituyentes seleccionados en forma independiente entre C1-2 alquilo, OH y F; o una sal o solvato o estereoisómero del mismo; que comprende: (a) hacer reaccionar un compuesto de fórmula (2) con un compuesto de fórmula (3) donde P1 es un grupo protector de amino, en presencia de un agente reductor; (b) hacer reaccionar un compuesto de fórmula (4) con un compuesto de fórmula (5) donde P2 es un grupo protector de amino, en presencia de un agente reductor; (c) hacer reaccionar un compuesto de fórmula (6) donde L1 es un grupo saliente, con un compuesto de fórmula (3); o (d) hacer reaccionar un compuesto de fórmula (4) con un compuesto de fórmula (7) donde L2 es un grupo saliente y P3 es un grupo protector de amino; y luego (e) eliminar el grupo protector P1, P2 o P3 para dar un compuesto de fórmula (1) o una sal del mismo.
ARP040102027A 2003-06-13 2004-06-11 Pirrolidinas y piperidinas sustituidas, compuestos relacionados, procedimientos para su preparacion y composiciones farmaceuticas que los contienen. AR044676A1 (es)

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US (5) US7183292B2 (es)
EP (1) EP1633707A1 (es)
JP (1) JP2007507496A (es)
KR (1) KR20060017541A (es)
CN (2) CN100406435C (es)
AR (1) AR044676A1 (es)
AU (1) AU2004253869B2 (es)
BR (1) BRPI0411358A (es)
CA (1) CA2525801A1 (es)
CL (1) CL2004001431A1 (es)
CO (1) CO5650231A2 (es)
IS (1) IS8155A (es)
MA (1) MA27852A1 (es)
MX (1) MXPA05013256A (es)
MY (1) MY139290A (es)
NO (1) NO20060191L (es)
NZ (1) NZ543805A (es)
PE (1) PE20050282A1 (es)
RU (1) RU2337095C2 (es)
TW (1) TW200510298A (es)
WO (1) WO2005003090A1 (es)
ZA (1) ZA200509942B (es)

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US20080146649A1 (en) 2008-06-19
ZA200509942B (en) 2006-12-27
CN101108809A (zh) 2008-01-23
US20070135482A1 (en) 2007-06-14
NZ543805A (en) 2009-06-26
US20040254219A1 (en) 2004-12-16
MA27852A1 (fr) 2006-04-03
MXPA05013256A (es) 2006-03-09
CN1805927A (zh) 2006-07-19
EP1633707A1 (en) 2006-03-15
US20070078163A1 (en) 2007-04-05
CA2525801A1 (en) 2005-01-13
MY139290A (en) 2009-09-30
KR20060017541A (ko) 2006-02-23
AU2004253869A1 (en) 2005-01-13
WO2005003090A1 (en) 2005-01-13
US7183292B2 (en) 2007-02-27
IS8155A (is) 2005-11-28
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US7638639B2 (en) 2009-12-29
US7615566B2 (en) 2009-11-10
CL2004001431A1 (es) 2005-03-18
US20080161577A1 (en) 2008-07-03
CN100406435C (zh) 2008-07-30
JP2007507496A (ja) 2007-03-29
NO20060191L (no) 2006-03-10
CO5650231A2 (es) 2006-06-30
AU2004253869B2 (en) 2010-02-18
RU2006101151A (ru) 2006-06-27
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US7351717B2 (en) 2008-04-01
CN101108809B (zh) 2010-07-14
PE20050282A1 (es) 2005-04-29
US7351718B2 (en) 2008-04-01

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