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AR046793A1 - Derivados de pirazol, antagonistas del receptor de la orexina - Google Patents

Derivados de pirazol, antagonistas del receptor de la orexina

Info

Publication number
AR046793A1
AR046793A1 ARP040104839A ARP040104839A AR046793A1 AR 046793 A1 AR046793 A1 AR 046793A1 AR P040104839 A ARP040104839 A AR P040104839A AR P040104839 A ARP040104839 A AR P040104839A AR 046793 A1 AR046793 A1 AR 046793A1
Authority
AR
Argentina
Prior art keywords
group
alkyl
atom
general formula
partially
Prior art date
Application number
ARP040104839A
Other languages
English (en)
Inventor
Michel Aletru
Peter Aranyi
Maria Balogh
Sandor Batori
Judit Bence
Philippe Bovy
Zoltan Kapui
Endre Mikus
Claudie Namane
Christophe Philippo
Tibor Szabo
Katalin Urban-Szabo
Zsuzsanna Toemoeskoezi
Original Assignee
Sanofi Aventis
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 Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR046793A1 publication Critical patent/AR046793A1/es

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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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • 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
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/20—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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A—HUMAN NECESSITIES
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/16—Halogen atoms or nitro radicals
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    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • 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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    • 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
    • C07D401/14—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 three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • 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
    • 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
    • C07D417/14—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 three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Emergency Medicine (AREA)
  • Cardiology (AREA)
  • Psychiatry (AREA)
  • Anesthesiology (AREA)
  • Rheumatology (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Reproductive Health (AREA)
  • Nutrition Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Compuestos antagonistas del receptor de la orexina de la fórmula general (1), Ar representa un grupo fenilo o un anillo heteroaromático de 5 o 6 miembros que contiene 1-3 heteroátomos, preferiblemente un átomo de N, un átomo de O o un átomo de S, donde cualquiera de estos anillos puede estar opcionalmente mono o polisustituidos con un átomo de halógeno, un grupo alquilo C1-4, un grupo alcoxilo C1-4, un grupo hidroxilo, un grupo ciano, un grupo trihalógenometilo, un grupo amino o un grupo amino sustituido con uno o dos grupos alquilo C1-4; Y representa un grupo -CH2-; X representa un átomo de S, un átomo de O, un grupo -NH-, un grupo -N(alquilo C1-4), un grupo -CH2-, un grupo -(S=O)- o un grupo -SO2-; o X e Y representan juntos un grupo -CH=CH- con geometría cis o trans, A representa una porción con un anillo heteroaromático de 5 o 6 miembros que contiene, en la posición orto, meta o para, dos valencias libres, que está opcionalmente mono o polisustituido con un átomo de halógeno, un grupo alquilo C1-4 o un grupo alcoxilo C1-4; o con un anillo de cicloalquilo de 5 o 6 miembros parcial o completamente saturado, opcionalmente mono o polisustituido con un átomo de halógeno, un grupo alquilo C1-4 o un grupo alcoxilo C1- 4; o con un anillo heteroaromático o heterocíclico parcial o completamente saturado que contiene 1-3 heteroátomos, preferiblemente un átomo de N, O o S, que está opcionalmente mono o polisustituido con un átomo de halógeno, un grupo alquilo C1-4 o un grupo alcoxilo C1-4; R1 representa un grupo bencilo, alquilo C1-4, hidroxialquilo C1-4, alcoxicarbonilalquilo C3-8,alquilcarbonilo C2-7, carboxialquilo C2-7, aminocarbonil-C1-4-alquilo, C1-3-alquilaminocarbonil-C1-4-alquilo, amino-C1-4-alquilo, C1-3-alquilamino-C1-4-alquilo, morfolino C1-4-alquilo, o morfolinocarbonil-C1-4-alquilo, o un grupo fenilo opcionalmente sustituido con uno o más átomos de halógenos; R2 representa uno de los siguientes grupos, que está opcionalmente sustituido con uno o más átomos de halógenos; un grupo hidroxilo, un grupo alquilo C1-4, un grupo trihalógenometilo, un grupo tio-C1-4-alquilo, un grupo amino, un grupo -(C=O)-NH-C1-4-alquilo o cicloalquilo; un grupo fenilo, un grupo feniletilo, un grupo naftilo, un grupo indanilo o indenilo, un grupo cíclico de 5 o 6 miembros, heteroaromático o parcial o completamente saturado que contiene 1-3 heteroátomos idénticos o diferentes, preferiblemente un átomo de N, O o S, un grupo que contiene una porción heteroaromática bicíclica o un heteroanillo bicíclico parcial o completamente saturado con 1, 2 o 3 heteroátomos idénticos o diferentes, preferiblemente un átomo de N, O o S; R3 representa un átomo de H o un grupo alquilo C1-4, R2 y R3, junto con el átomo de N al que están unidos, representan un anillo de 6 miembros parcial o completamente saturado opcionalmente sustituido con un grupo fenilo o bencilo sustituido; R5 representa un átomo de halógeno, un átomo de H, un grupo alquilo C1-4, un grupo tioalquilo C1-4, un grupo alcoxilo C1-4, y sus sales, isómeros y solvatos, las composiciones farmacéuticas que los contienen y la aplicación terapéutica de los mismos. Un proceso para preparar los compuestos de fórmula general (1), y sus sales, isómeros y solvatos, donde a) se transforma el ácido de fórmula general (2) en su derivado activo, y se lo hace reaccionar con la amina de fórmula general (3) NHR2R3 o b) se hace reaccionar un derivado de clorometilo de fórmula general (4) con una amida de fórmula general (5) y, si se lo desea, se libera el compuesto resultante de su sal, o se lo transforma en una sal.
ARP040104839A 2003-12-22 2004-12-22 Derivados de pirazol, antagonistas del receptor de la orexina AR046793A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU0304101A HUP0304101A3 (en) 2003-12-22 2003-12-22 Pyrazole derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates

Publications (1)

Publication Number Publication Date
AR046793A1 true AR046793A1 (es) 2005-12-21

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ID=89981868

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ARP040104839A AR046793A1 (es) 2003-12-22 2004-12-22 Derivados de pirazol, antagonistas del receptor de la orexina

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Country Link
US (2) US7659298B2 (es)
EP (1) EP1699454B1 (es)
JP (1) JP4861829B2 (es)
AR (1) AR046793A1 (es)
AT (1) ATE438395T1 (es)
DE (1) DE602004022458D1 (es)
HU (1) HUP0304101A3 (es)
TW (1) TWI289558B (es)
WO (1) WO2005060959A1 (es)

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PA8535601A1 (es) * 2000-12-21 2002-11-28 Pfizer Derivados benzimidazol y piridilimidazol como ligandos para gabaa
HUP0304101A3 (en) * 2003-12-22 2008-10-28 Sanofi Aventis Pyrazole derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates

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ATE438395T1 (de) 2009-08-15
DE602004022458D1 (de) 2009-09-17
HUP0304101A2 (hu) 2005-09-28
WO2005060959A1 (en) 2005-07-07
EP1699454B1 (en) 2009-08-05
TWI289558B (en) 2007-11-11
US7659298B2 (en) 2010-02-09
US20110059964A1 (en) 2011-03-10
HUP0304101A3 (en) 2008-10-28
EP1699454A1 (en) 2006-09-13
TW200526632A (en) 2005-08-16
JP2007519630A (ja) 2007-07-19
US20070021459A1 (en) 2007-01-25
HU0304101D0 (en) 2004-03-29
WO2005060959A8 (en) 2006-01-12
JP4861829B2 (ja) 2012-01-25

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