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CO5140073A1 - Derivados de 2,3,4,5-tetrahidro-1h-3-benzapina - Google Patents

Derivados de 2,3,4,5-tetrahidro-1h-3-benzapina

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Publication number
CO5140073A1
CO5140073A1 CO99063348A CO99063348A CO5140073A1 CO 5140073 A1 CO5140073 A1 CO 5140073A1 CO 99063348 A CO99063348 A CO 99063348A CO 99063348 A CO99063348 A CO 99063348A CO 5140073 A1 CO5140073 A1 CO 5140073A1
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compound
formula
alkyl
jpeg
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CO99063348A
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English (en)
Inventor
Michael Stewart Hadley
Geoffrey Stemp
Christopher Norbert Johnson
Keong Vong Antonio Kuok
Gregor James Macdonald
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Smithkline Beecham Plc
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Priority claimed from GBGB9821976.9A external-priority patent/GB9821976D0/en
Priority claimed from GBGB9824340.5A external-priority patent/GB9824340D0/en
Priority claimed from GBGB9910711.2A external-priority patent/GB9910711D0/en
Priority claimed from GBGB9918032.5A external-priority patent/GB9918032D0/en
Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc
Publication of CO5140073A1 publication Critical patent/CO5140073A1/es

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    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/16—Benzazepines; Hydrogenated benzazepines
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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    • 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
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • 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
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    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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    • A61P25/20—Hypnotics; Sedatives
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    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • 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
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    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A61P25/34—Tobacco-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
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    • 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
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
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    • 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
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
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  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Un compuesto de fórmula (I)<EMI FILE="99063348_1" ID="1" IMF=JPEG >en la que:R1 representa un sustituyente seleccionado entre: un átomo de hidrógeno o de halógeno; un grupo hidroxi, ciano, nitro, trifluorometilo, trifluorometoxi, trifluorometanosul- foniloxi, pentafluoroetilo, alquilo de C1-4, alcoxi de C1-4, aril-alcoxi de C1-4, alquil(C1-4)-tio, alcoxi de C1-4-alquilo de C1-4, cicloalquilo de C3-6-alcoxi de C1-4, alcanoilo de C1-4, alcoxi de C1-4-carbonilo, alquil(C1-4)sulfonilo, alquil(C1-4)sulfoniloxi, alquil(C1-4)sulfonilo-alquilo de C1-4, arilsulfonilo, arilsulfoniloxi, arilsulfonil-alquilo de C1-4, alquil(C1-4)sulfonamido, alquil(C1-4)amido, alquil (C1-4)sulfonamido-alquilo de C1-4, alquil (C1-4)amido-alquilo de C1-4, arilsulfonamido, arilcarboxamido, arilsulfonamido- alquilo de C1-4, arilcarboxamido-alquilo de C1-4, aroilo, aroil-alquilo de C1-4, o aril-alcanoilo de C1-4; un grupo R3OCO(CH2)p, R3CON(R4)(CH2)p, R3R4NCO(CH2)p ó R3R4NSO2(CH2)p, en cada una de cuyas fórmulas R3 y R4, independientemente, representa un átomo de hidrógeno o un grupo alquilo de C1-4 ó R3R4 forma parte de un anillo de azacicloalcano de C3-6 o (2-oxo)azacicloalcano de C3-6 y p representa cero o un número entero desde 1 a 4; o un grupo Ar3-Z, en el que Ar3 representa un anillo de fenilo opcionalmente sustituido o un anillo heterocíclico aromáticos de 5 o 6 miembros opcionalmente sustituido, y Z representa un enlace, O, S ó CH2; R2 representa un átomo de hidrógeno o un grupo alquilo de C1-4; q es 1 ó 2; A representa un grupo de la fórmula (a), (b) (c) o (d):-Ar -Ar1-Y-Ar2 <EMI FILE="99063348_2" ID="2" IMF=JPEG > (CH2)r-V-(CH2)sSr(a) (b) (c) (d) en las que: Ar representa un anillo de fenilo opcionalmente sustituido o un anillo heterocíclico aromático de 5 ó 6 miembros opcionalmente sustituido; o un sistema de anillos bicíclico opcionalmente sustituido; Ar1 y Ar2, cada uno independientemente, representan un anillo de fenilo opcionalmente sustituido o un anillo heterocíclico aromático de 5 ó 6 miembros opcionalmente sustituido; e Y representa un enlace, -NHCO-, -CONH-, -CH2- o -(CH2)mY1(CH2)n-, en cuyas fórmulas Y1 representa O, S, S02 o CO, y m y n representan cada uno cero ó 1, de tal modo que Ia suma de m+n es cero ó 1; con tal que cuando A representa un grupo de fórmula (a), cualquier sustituyente presente en Ar en posición orto respecto al resto de carboxamida es necesariamente un grupo hidrógeno o un grupo metoxi; r y s independientemente, representan un número entero desde cero a 3, de tal modo que la suma de r y s es igual a un número entero desde 1 a 4; V representa un enlace, 0 o S; y sus sales. - 2 -Un procedimiento de preparación de compuestos defórmula (I) cuyo procedimiento comprende:(a) hacer reaccionar un compuesto de fórmula (II)<EMI FILE="99063348_3" ID="3" IMF=JPEG >en la que R1, R2 y q son como se ha definido anteriormente, con un compuesto de fórmula (III):<EMI FILE="99063348_4" ID="4" IMF=JPEG >en la que A es como se ha definido anteriormente y X es un átomo de halógeno o el resto de un éster activado;(b) preparar un compuesto de fórmula (I) haciendo reaccionar un compuesto de fórmula (II) con un compuesto A-Br, o A-l, o A-OSO2CF3 en presencia de monóxido de carbono y un catalizador tal como bromuro de trans-bis-trifenilfosfinapaladio (II); (c) preparar un compuesto de fórmula (I) en la que R1 es Ar3-Z y Z es un enlace, haciendo reaccionar un compuesto de fórmula (IV);<EMI FILE="99063348_5" ID="5" IMF=JPEG >en la que R2 y A son como se ha definido anteriormente y un R1a representa un grupo W, en el que W es un átomo de halógeno o un grupo trifluorometilsulfoniloxi, o W es un grupo M seleccionado entre un derivado de boro, por ejemplo una función de ácido borónico B(OH)2 o una función metálica tal como trialquilestannilo, por ejemplo, SnBu3, haluro de cinc o haluro de magnesio, y cuando q es 2 el otro R1a es R1; con un compuesto Ar3-W1, en el que W1 es un átomo de halógeno o un grupo trifluorometilsulfoniloxi cuando W es un grupo M o W1 es un grupo M cuando W es un átomo de halógeno o un grupo trifluorometilsulfoniloxi;(d) preparar un compuesto de fórmula (I) en la que R1 es Ar3-Z y Z es O ó S, haciendo reaccionar un compuesto de fórmula (V):<EMI FILE="99063348_6" ID="6" IMF=JPEG >en la que R2 y A son como se ha definido anteriormente, y un R1b representa un grupo ZH, y cuando q es 2 el otro R1brepresenta R1; con un reactivo que sirve para introducir elgrupo Ar3;(e) preparar un compuesto de fórmula (I) en la que Y es un enlace, haciendo reaccionar un compuesto de fórmula (VI):<EMI FILE="99063348_7" ID="7" IMF=JPEG >en la que R1, R2, Ar1, W y q son como se ha definido anteriormente, con un compuesto Ar2-W1, en el que W1 es un átomo de halógeno o un grupo trifluorometilsulfoniloxi cuando W es un grupo M, o W1 es un grupo M cuando W es un átomo de halógeno o un grupo trifluorometilsulfoniloxi. (f) interconversión de un compuesto de fórmula (I) en un compuesto diferente de fórmula (I), por ejemplo, (i) alquilación de un compuesto (I) en el que R2 representa hidrógeno, (ii) conversión de un R1 desde alcoxi (por ejemplo, metoxi) a hidroxi, o (iii) conversión de R1 desde hidroxi a sulfoniloxi, por ejemplo, alquilsulfoniloxi o trifluorometanosulfoniloxi; (iv) conversión de un compuesto en el que Y representa S, en un compuesto en el que Y es S02 o (v) conversión de Y desde CO a CH2;(g) separación de los isómeros cis y trans de compuestos de fórmula (I) mediante métodos convencionales, por ejemplo, cromatografía o recristalización;y opcionalmente, después de esto, formar una sal de fórmula (I) .
CO99063348A 1998-10-08 1999-10-06 Derivados de 2,3,4,5-tetrahidro-1h-3-benzapina CO5140073A1 (es)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9821976.9A GB9821976D0 (en) 1998-10-08 1998-10-08 Compounds
GBGB9824340.5A GB9824340D0 (en) 1998-11-06 1998-11-06 Compounds
GBGB9910711.2A GB9910711D0 (en) 1999-05-07 1999-05-07 Compounds
GBGB9918032.5A GB9918032D0 (en) 1999-07-30 1999-07-30 Compounds

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CO5140073A1 true CO5140073A1 (es) 2002-03-22

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US (1) US6605607B1 (es)
EP (1) EP1119563B1 (es)
JP (1) JP2002527433A (es)
KR (1) KR20010085898A (es)
CN (1) CN1329609A (es)
AP (1) AP2001002114A0 (es)
AR (1) AR023681A1 (es)
AT (1) ATE316969T1 (es)
AU (1) AU761018B2 (es)
BG (1) BG105467A (es)
BR (1) BR9914370A (es)
CA (1) CA2346689A1 (es)
CO (1) CO5140073A1 (es)
CZ (1) CZ20011270A3 (es)
DE (1) DE69929704T2 (es)
EA (1) EA200100428A1 (es)
ES (1) ES2255311T3 (es)
HK (1) HK1038745A1 (es)
HU (1) HUP0104280A3 (es)
ID (1) ID28385A (es)
IL (1) IL142388A0 (es)
MA (1) MA26696A1 (es)
NO (1) NO20011745L (es)
NZ (1) NZ511018A (es)
OA (1) OA11663A (es)
PE (1) PE20001088A1 (es)
PL (1) PL347237A1 (es)
SK (1) SK4782001A3 (es)
TR (1) TR200101025T2 (es)
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