AR064134A1 - Derivados de 2-aminoquinolina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo de los receptores 5-ht5a. - Google Patents

Derivados de 2-aminoquinolina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo de los receptores 5-ht5a.

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Publication number
AR064134A1
AR064134A1 ARP070105425A ARP070105425A AR064134A1 AR 064134 A1 AR064134 A1 AR 064134A1 AR P070105425 A ARP070105425 A AR P070105425A AR P070105425 A ARP070105425 A AR P070105425A AR 064134 A1 AR064134 A1 AR 064134A1
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AR
Argentina
Prior art keywords
formula
compound
give
reaction
alkyl
Prior art date
Application number
ARP070105425A
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English (en)
Inventor
Sabine Kolczewski
Claus Riemer
Lucinda Steward
Juergen Wichmann
Thomas Woltering
Original Assignee
Hoffmann La Roche
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Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of AR064134A1 publication Critical patent/AR064134A1/es

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    • 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
    • C07D215/16—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 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
    • C07D215/38—Nitrogen 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/12—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
    • 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
    • C07D405/14—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Nutrition Science (AREA)
  • Hospice & Palliative Care (AREA)
  • Addiction (AREA)
  • Anesthesiology (AREA)
  • Psychology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Derivados de 2-aminoquinolina como receptores antagonistas de 5-HT5a, su fabricacion, las composiciones farmacéuticas que los contienen y su uso como medicamentos. Los compuestos de formula 1 general son utiles en la prevencion y/o tratamiento de depresion, trastornos de ansiedad, esquizofrenia, trastornos de pánico, agorafobia, fobia social, trastornos obsesivo-compulsivos, trastornos de estrés post-traumático, dolor, trastornos de memoria, demencia, trastornos de comportamiento alimentario, disfuncion sexual, trastornos del sueno, retraimiento del abuso de drogas, trastornos motores tales como la enfermedad de Parkinson, trastornos psiquiátricos o trastornos gastrointestinales. Reivindicacion 1: Un compuesto de formula general (1) donde X es un enlace, -NRa-, -O-, -S-, -SO2-, -NRbS(O)2-, -NRcCH2-, -OCH2-, -CH2O-, -SCH2-, -CH2S-, -NRdC(O)-, -CH2NRc-, -CH2CH2-, -CH=CH-, -CH2S(O)2-, -OCH2CH2-, -SCH2CH2-, -NRcCH2CH2-, -CH2NRdC(O)-, -CH2NRcCH2-, -C(NRk)-, -C(O)-, - NRbS(O)2NRb-, -C(N-ORp)-, R1 es un arilo mono- o bicíclico, o un heteroarilo mono- o bicíclico, siendo cada uno opcionalmente sustituido por uno o más halo, alquilo C1-7, opcionalmente sustituido por OH o CN, alcoxi C1-7, -S(O)2-alquilo C1-7, - NReRf, -S(O)2-NRgRh, halo-alquilo C1-7, -CH2-O-alquilo C1-7, -(OCH2CH2)m-ORi, donde m va desde 1 hasta 3, -(OCH2CH2)m-NRqRr, donde m va desde 1 hasta 3, -CH2-(N-morfolino),-CH2-(OCH2CH2)m-ORj, donde m va desde 1 hasta 3, hidroxi, ciano, nitro, o alilo; R2 es un cicloalquilo o heterocicloalquilo de 5 a 7 miembros, o un biciclo[2.2.1]heptilo cada uno opcionalmente hibridado con un carbo- o heterociclo de 5- o 6- miembros aromático, cada uno opcional e independientemente sustituido con un o más alcoxi C1-7, hidroxi, halo, alquilo C1-7, opcionalmente sustituido por OH o CN, -S(O)2-alquilo C1-7, -NReRf, -S(O)2-NRgRh, -CH2-O-alquilo C1-7, -(OCH2CH2)m-ORi, donde m va desde 1 hasta 3, -CH2-(OCH2CH2)m-ORj, donde m va desde 1 hasta 3, ciano, nitro, o alilo; Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, Rp, Rq y Rr es cada uno independientemente hidrogeno, alquilo C1-7 o (CH2)n-cicloalquilo, donde n va desde 0 hasta 3; o sales de adicion ácida del mismo, farmacéuticamente aceptable. Reivindicacion 10: Un proceso para preparar un compuesto de formula (1), el cual comprende, reaccion de un compuesto de formula (2) con una amina de formula R2NH2, para dar un compuesto de formula (1) donde R1 y R2 son como se definen en la reivindicacion 1; o reaccion de un compuesto de formula (3) con una amina de formula R1-Z1-NH2 para dar un compuesto de formula (4) donde Z1 es -CH2- o -CH2CH2- y R1 y R2 son como se definen en la reivindicacion 1; o reaccion de un compuesto de formula (5) con un cloruro de sulfonilo de formula R1SO2Cl, para dar un compuesto de formula (6) donde R1 y R2 son como se definen en la reivindicacion 1; o reaccion de un compuesto de formula (7) con un compuesto de formula R1CHO, para dar un compuesto de formula (8) donde R1 y R2 son como se definen en la reivindicacion 1; o reaccion de un compuesto de formula (7) con un compuesto de formula R1Z2Cl, para dar un compuesto de formula (9) donde Z2 es -CH2- o -CH2CH2-y R1 y R2 son como se definen en la reivindicacion 1; o reaccion de un compuesto de formula (10) con una amina de formula R'NH2, para dar un compuesto de formula (11) donde se selecciona R' a partir de alquilo C1-7 o -(CH2)n-cicloalquilo, donde n va desde 0 hasta 3 y R2 es como se define en la reivindicacion 1; o reaccion de un compuesto de formula (7) con un compuesto de formula R1Br, para dar un compuesto de formula (12) donde R2 es como se define en la reivindicacion 1 y R1 es un arilo opcionalmente sustituido; o h) reaccion de un compuesto de formula (3) con un ácido boronico de formula R1-B(OH)2 para dar un compuesto de formula (13) donde R1 y R2 son como se definen más arriba; o i) reaccion de un compuesto de formula (7) con un cloruro de sulfamaceite de formula R1NSO2Cl para dar un compuesto de formula (14) donde R1 y R2 son como se definen más arriba; o j) reaccion de un compuesto de formula (15) con un compuesto de formula R1COCl para dar un compuesto de formula (16) donde R1 y R2 son como se definen más arriba; o k) reaccion de un compuesto de la formula (15) con un compuesto de formula R1CHO para dar un compuesto de formula (17) donde R1 y R2 son como se definen más arriba; o l) reaccion de un compuesto de formula (18) con un compuesto de formula R1MgHal para dar un compuesto de formula (19) donde R1 y R2 son como se definen más arriba; o m) reaccion de un compuesto de formula (18) con HCl para dar la correspondiente cetona de formula (20) donde R1 y R2 son como se describen más arriba; o n) reaccion de un compuesto de formula (21) con ácido acético para dar un compuesto de formula (22) donde R2 es como se describe más arriba; u o) reaccion de un compuesto de formula (20) con una hidroxilamina de formula NH2OR1 para dar la correspondiente oxima de formula (23) donde R1, R2 y R1 son como se describen más arriba; y, si se desea, conversion de los compuestos obtenidos en sales de adicion ácida farmacéuticamente aceptables.
ARP070105425A 2006-12-07 2007-12-05 Derivados de 2-aminoquinolina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo de los receptores 5-ht5a. AR064134A1 (es)

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EP06125604 2006-12-07

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AR064134A1 true AR064134A1 (es) 2009-03-11

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ARP070105425A AR064134A1 (es) 2006-12-07 2007-12-05 Derivados de 2-aminoquinolina, un proceso para su preparacion, una composicion farmaceutica que los comprende y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por el antagonismo de los receptores 5-ht5a.

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US (1) US7923561B2 (es)
EP (1) EP2099763B1 (es)
JP (1) JP5031846B2 (es)
KR (1) KR101107807B1 (es)
CN (1) CN101541753B (es)
AR (1) AR064134A1 (es)
AT (1) ATE477243T1 (es)
AU (1) AU2007329064C1 (es)
BR (1) BRPI0720078A2 (es)
CA (1) CA2669590A1 (es)
CL (1) CL2007003481A1 (es)
DE (1) DE602007008469D1 (es)
ES (1) ES2348208T3 (es)
IL (1) IL198542A0 (es)
MX (1) MX2009005509A (es)
PE (1) PE20081446A1 (es)
TW (1) TW200845985A (es)
WO (1) WO2008068157A1 (es)

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BRPI0909634A2 (pt) * 2008-03-05 2015-09-22 Hoffmann La Roche 2-aminoquinolinas
CN101959864A (zh) 2008-03-07 2011-01-26 弗·哈夫曼-拉罗切有限公司 2-氨基喹啉衍生物
CA2717453A1 (en) * 2008-03-07 2009-09-11 F. Hoffmann-La Roche Ag 2-aminoquinolines
KR20110038180A (ko) * 2008-09-08 2011-04-13 에프. 호프만-라 로슈 아게 5-치환된 벤즈옥사진
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CA3230380A1 (en) 2021-09-01 2023-03-09 Nicholas MORRA Synthesis of mdma or its optically active (r)- or (s)-mdma isomers
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MX2009005509A (es) 2009-06-03
US7923561B2 (en) 2011-04-12
CA2669590A1 (en) 2008-06-12
PE20081446A1 (es) 2008-10-18
AU2007329064A1 (en) 2008-06-12
EP2099763B1 (en) 2010-08-11
DE602007008469D1 (de) 2010-09-23
US20080146567A1 (en) 2008-06-19
CN101541753B (zh) 2012-06-13
TW200845985A (en) 2008-12-01
BRPI0720078A2 (pt) 2013-12-24
KR101107807B1 (ko) 2012-01-25
ES2348208T3 (es) 2010-12-01
JP2010511653A (ja) 2010-04-15
AU2007329064B2 (en) 2012-08-02
KR20090080545A (ko) 2009-07-24
EP2099763A1 (en) 2009-09-16
AU2007329064C1 (en) 2013-01-17
WO2008068157A1 (en) 2008-06-12
IL198542A0 (en) 2010-02-17
CN101541753A (zh) 2009-09-23
ATE477243T1 (de) 2010-08-15
CL2007003481A1 (es) 2008-07-04
JP5031846B2 (ja) 2012-09-26

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