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AR064937A1 - Derivados de n-(heteroaril)-1-heteroaril-1h-indol-2-carboxamidas, su preparacion y su aplicacion en terapeutica - Google Patents

Derivados de n-(heteroaril)-1-heteroaril-1h-indol-2-carboxamidas, su preparacion y su aplicacion en terapeutica

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Publication number
AR064937A1
AR064937A1 ARP080100206A ARP080100206A AR064937A1 AR 064937 A1 AR064937 A1 AR 064937A1 AR P080100206 A ARP080100206 A AR P080100206A AR P080100206 A ARP080100206 A AR P080100206A AR 064937 A1 AR064937 A1 AR 064937A1
Authority
AR
Argentina
Prior art keywords
cycloalkyl
aryl
alkylene
alkyl
group
Prior art date
Application number
ARP080100206A
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English (en)
Inventor
Laurent Dubois
Yannick Evanno
Andre Malanda
Christian Maloizel
Original Assignee
Sanofi Aventis Us Llc
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 Us Llc filed Critical Sanofi Aventis Us Llc
Publication of AR064937A1 publication Critical patent/AR064937A1/es

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    • 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
    • C07D401/14—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
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    • A—HUMAN NECESSITIES
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    • A—HUMAN NECESSITIES
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    • A61P11/14—Antitussive agents
    • A—HUMAN NECESSITIES
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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Cardiology (AREA)
  • Biotechnology (AREA)
  • Ophthalmology & Optometry (AREA)
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  • Emergency Medicine (AREA)
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Abstract

Procedimiento de preparacion y aplicacion en terapéutica. Los compuestos presentan actividad antagonista in vivo e in vitro para los receptores de tipo TRPV1 o (VR1). Reivindicacion 1: Compuesto que responde a la formula general (1): en la que: X1, X2, X3, X4 representan, independientemente uno de otro, un átomo de hidrogeno o de halogeno o un grupo: alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, ciano, C(O)NR1R2, nitro, NR1R2, tioalquilo C1-6, -S(O)-alquilo C1-6, -S(O)2-alquilo C1-6, SO2NR1R2, NR3COR4, NR3SO2R5 o arilo, estando el arilo eventualmente sustituido por uno o varios sustituyentes elegidos entre: un halogeno, un grupo alquilo C1-6, cicloalquilo C3- 7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; W representa un grupo bicíclico condensado de formula (2) unido al átomo de nitrogeno por las posiciones 1, 2, 3 o 4; A representa un heterociclo de 5 a 7 eslabones que comprende de uno a tres heteroátomos elegidos entre O, S o N; estando el o los átomos de carbono de A eventualmente sustituidos por uno o varios grupos elegidos entre: un átomo de hidrogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquilo C3-7-alquileno C1-3, fluoroalquilo C1-6, alcoxilo C1-6, cicloalcoxilo C3-7, cicloalquil C3-7-alquilen C1-3-oxi, arilo, aril-alquileno C1-6, oxo o tio; estando el o los átomos de nitrogeno de A eventualmente sustituidos por R6 cuando el nitrogeno es adyacente a un átomo de carbono sustituido por un grupo oxo o por R7 en los otros casos; Y representa un heteroarilo eventualmente sustituido por uno o varios grupos elegidos entre: un átomo de halogeno o un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, hidroxilo, alcoxilo C1-6, fluoroalcoxilo C1-6, tiofluoroalquilo C1-6, ciano, C(O)NR1R2, nitro, NR1R2, tioalquilo C1-6, SH, -S(O)-alquilo C1-6, -S(O)2-alquilo C1-6, -S(O)-cicloalquilo C3-7, -S(O)2-cicloalquilo C3-7; SO2NR1R2, NR3COR4, NR3SO2R5, aril-alquileno C1-6 o arilo, estando el arilo y el aril-alquileno C1-6 eventualmente sustituidos por uno o varios sustituyentes elegidos entre: un halogeno, un grupo alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, alcoxilo C1-6, fluoroalcoxilo C1-6, nitro o ciano; R1 y R2, representan, independientemente uno de otro, un átomo de hidrogeno o un grupo: alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, aril-alquileno C1-6 o arilo o R1 y R2 forman conjuntamente, con el átomo de nitrogeno que los lleva, un grupo: azetidinilo, pirrolidinilo, piperidinilo, azepinilo, morfolinilo, tiomorfolinilo, piperazinilo, homopiperazinilo, estando este grupo eventualmente sustituido por un grupo: alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, aril-alquileno C1-6 o arilo; R3 y R4 representan, independientemente uno de otro, un átomo de hidrogeno o un grupo: alquilo C1-6, aril-alquileno C1-6 o arilo; R5 representa un grupo alquilo C1-6, aril-alquileno C1-6 o arilo; R6 representa un átomo de hidrogeno o un grupo: alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, aril-alquileno C1-6 o arilo; R7 representa un átomo de hidrogeno o un grupo: alquilo C1-6, cicloalquilo C3-7, cicloalquil C3-7-alquileno C1-3, fluoroalquilo C1-6, aril-alquileno C1-6, alquil C1-6-C(O)-, cicloalquil C3-7-alquilen C1-3-(CO)-, fluoroalquil C1-6-C(O)-, cicloalquil C3-7-C(O)-, aril-C(O)-, aril-alquilen C1-6-C(O)-, alquil C1-6-S(O)2-, fluoroalquil C1-6-S(O)2-, cicloalquil C3-7-S(O)2-, cicloalquil C3-7-alquilen C1-3-S(O)2-, aril-S(O)2- o aril-alquilen C1-6-S(O)2- o arilo, pudiendo estar el o los átomos de azufre del heterociclo A o del heteroarilo Y en forma oxidada; pudiendo estar el o los átomos de nitrogeno del heterociclo A o del heteroarilo Y en forma oxidada; en el estado de base o de sal de adicion de ácido, así como en el estado de hidrato o de solvato.
ARP080100206A 2007-01-19 2008-01-17 Derivados de n-(heteroaril)-1-heteroaril-1h-indol-2-carboxamidas, su preparacion y su aplicacion en terapeutica AR064937A1 (es)

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FR0700357A FR2911604B1 (fr) 2007-01-19 2007-01-19 Derives de n-(heteroaryl-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique

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US (1) US7868024B2 (es)
EP (1) EP2125787B1 (es)
JP (1) JP5264773B2 (es)
AR (1) AR064937A1 (es)
CL (1) CL2008000127A1 (es)
ES (1) ES2624795T3 (es)
FR (1) FR2911604B1 (es)
PE (1) PE20081689A1 (es)
TW (1) TW200900058A (es)
UY (1) UY30874A1 (es)
WO (1) WO2008107544A1 (es)

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MXPA04005427A (es) 2001-12-10 2005-04-19 Amgen Inc Ligandos de receptor vainilloide y su uso en tratamientos.
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FR2888847B1 (fr) * 2005-07-22 2007-08-31 Sanofi Aventis Sa Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique
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FR2911604A1 (fr) 2008-07-25
TW200900058A (en) 2009-01-01
EP2125787A1 (fr) 2009-12-02
US20090306143A1 (en) 2009-12-10
FR2911604B1 (fr) 2009-04-17
PE20081689A1 (es) 2008-12-31
ES2624795T3 (es) 2017-07-17
CL2008000127A1 (es) 2008-05-23
WO2008107544A1 (fr) 2008-09-12
JP5264773B2 (ja) 2013-08-14
US7868024B2 (en) 2011-01-11
UY30874A1 (es) 2008-09-02
JP2010516662A (ja) 2010-05-20
EP2125787B1 (fr) 2017-03-01

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