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AR056688A1 - DERIVATIVES OF THE 4- AMINO - QUINAZOLINA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS - Google Patents

DERIVATIVES OF THE 4- AMINO - QUINAZOLINA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS

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Publication number
AR056688A1
AR056688A1 ARP060104457A ARP060104457A AR056688A1 AR 056688 A1 AR056688 A1 AR 056688A1 AR P060104457 A ARP060104457 A AR P060104457A AR P060104457 A ARP060104457 A AR P060104457A AR 056688 A1 AR056688 A1 AR 056688A1
Authority
AR
Argentina
Prior art keywords
alkylene
group
alkyl
aryl
nrarb
Prior art date
Application number
ARP060104457A
Other languages
Spanish (es)
Inventor
Jean Michel Augereau
Gilles Courtemanche
Pierre Despeyroux
Michel Geslin
Anne Thomas
Original Assignee
Sanofi Aventis
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=36645639&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR056688(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR056688A1 publication Critical patent/AR056688A1/en

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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
    • C07D401/02—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • A61P25/22—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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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

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

Abstract

utiles para trastornos metabolicos. Reivindicacion 1: Compuesto que responde a la formula general (1) en la que: A representa un grupo alquileno C1-4 opcionalmente sustituido con uno o varios grupos R9 idénticos o diferentes uno de otro; B representa un grupo alquileno C1-4 opcionalmente sustituido con uno o varios grupos R10 idénticos o diferentes uno de otro; R9 y R10 representan cada uno, de manera independiente el uno del otro, un átomo de H o un grupo alquilo C1-5; o bien R9 y R10 forman juntos un enlace sencillo o un grupo alquileno C1-4; L representa un enlace sencillo o un grupo alquileno C1-2, -CH=CH- o -C:::C-, estando los grupos alquileno C1-2 y-CH=CH- opcionalmente sustituidos con uno o varios sustituyentes alquilo C1-2 o bien L representa un grupo cicloprop-1,2-di-ilo; R representa un átomo de H o un grupo alquilo C1-5, fluoroalquilo C1-3, cicloalquilo C3-6, -C(O)-alquilo C1-3, alquileno C1-3-cicloalquilo C3-6, -CH2-C:::CH, alquileno C2-4-NRaRb o alquileno C1- 3-X-alquilo C1-3 en el que X representa O o SO2; R1 representa un arilo o un heteroarilo; estando los grupos arilo y heteroarilo opcionalmente sustituidos con uno o varios radicales Z idénticos o diferentes uno de otro, R2 y R3 representan, de forma independiente el uno del otro, un átomo de H o un grupo alquilo C1-3 o fluoroalquilo C1-3; o bien R2 y R3 forman juntos, con el átomo de C que los soporta, un grupo cicloprop-1,1-di-ilo; R4 representa: un átomo de H o un grupo alquilo C1-5, fluoroalquilo C1-3, alcoxi C1-5, -SF5 o alquileno C1-3-X-alquilo C1-3 en el que X representa O o SO2, un grupo alquileno C1-5-NRaRb, un arilo o un heteroarilo; estando los grupos arilo y heteroarilo opcionalmente sustituidos con uno o varios radicales Z idénticos o diferentes uno de otro; R5 representa un átomo de H o de halogeno o un grupo alquilo C1-5, fluoroalquilo C1-3, alcoxi C1-5, cicloalquilo C3-6, alquileno C1-3-cicloalquilo C3-6, alquileno C1-3-O-alquilo C1-3, alquileno C1-3- (OH) o alquileno C1-3-X-alquilo C1-3 en el que X representa S, SO o SO2, o bien R5 representa un grupo -NRaRb, alquileno C1-3-NRaRb, arilo, alquileno C1-3-arilo, -O-arilo, alquileno C1-3-O-arilo, alquileno C1-3-O-alquileno C1-3-arilo, heteroarilo o alquileno C1-3-heteroarilo; estando los grupos arilo, alquileno C1-3-arilo, -O-arilo, alquileno C1-3-O-arilo, alquileno C1-3-O-alquileno C1-3-arilo, heteroarilo y alquileno C1-3-heteroarilo opcionalmente sustituidos con uno o varios radicales Z idénticos o diferentes uno de otro, o bien R5 representa un grupo heterociclo, estando dicho heterociclo opcionalmente sustituido con un grupo alquilo C1-3, -C(O)-alquilo C1-3, -C(O)-fluoroalquilo C1-3, alquileno C1-3-cicloalquilo C3-6, alquileno C1- 3-arilo o alquileno C1-3-heteroarilo; estando los grupos alquileno C1-3-arilo y alquileno C1-3-heteroarilo opcionalmente sustituidos con uno o varios radicales Z idénticos diferentes uno de otro; R7 representa un átomo de H o de halogeno o un grupo alquilo C1-5, fluoroalquilo C1-3, alcoxi C1-5, -COOH, -C(O)O-alquilo C1-3, fluoroalcoxi C1-3, alquileno C1-3-(OH), -NO2, -CN o -X-alquilo C1-3 en el que X representa S, SO o SO2, o bien R7 representa un grupo -NRaRb, alquileno C1-3-NRaRb, -C(O)- NRaRb, -C(O)-alquilo C1-3, arilo, -O-arilo o heteroarilo; estando los grupos arilo, -O-arilo y heteroarilo opcionalmente sustituidos con uno o varios radicales Z idénticos o diferentes uno de otro; Z representa un átomo de halogeno o un grupo alquilo C1-5, fluoroalquilo C1-3, cicloalquilo C3-6, alquileno C1-3-cicloalquilo C3-6, un fenilo, alcoxi C1-5, fluoroalcoxi C1-3, alquileno C1-3-O-alquilo C1-3, alquileno C1-3-(OH), NO2, -CN, -SO2NRaRb, -X-alquilo C1-3 o alquileno C1-3-X-alquilo C1- 3 en los que X representa S, SO o SO2, o bien Z representa un fenilo opcionalmente sustituido con un átomo de halogeno, un grupo alquilo C1-5, alcoxi C1-5 o fluoroalquilo C1-3, o bien Z representa un radical alquinilo del tipo -C:::C-Rc, en el que Rc representa un átomo de H, un grupo alquilo C1-3, alquileno C1-6-O-Rd o alquileno C1-6-NRaRb, o bien Z representa un grupo -alquileno C4-6-ORd, o bien Z representa un grupo tetrazol sustituido con un grupo alquilo C1-3, o bien Z representa un grupo -NRaRb, alquileno C1-6-NRaRb o -C(O)-NRaRb, -C(O)-alquilo C1-3, -C(O)-O-alquilo C1-4, -C(O)-cicloalquilo C3-6, o bien Z representa un radical oxo, o bien Z representa un grupo -O-alquileno C1-5-NRaRb, o bien dos radicales Z adyacentes forman juntos un grupo alquileno C1-3-dioxi; o bien Z representa un grupo -O-alquileno C0-3-heterociclo, opcionalmente sustituido con uno o varios grupos alquilo C1-3, oxo o -C(O)-alquilo C1-3, o bien Z representa un grupo -O-alquileno C1-5-O-Rd, o bien Z representa un grupo -O-alquileno C0-3-cicloalquilo C5-7 opcionalmente sustituido con un grupo -O-Rd, o bien Z representa un grupo -NRe-alquileno C0-3-heterociclo opcionalmente sustituido con uno o varios grupos alquilo C1-3, oxo o -C(O)-alquilo C1- 3, o bien Z representa un grupo -NRe-alquileno C2-5-O-Rd, o bien Z representa un grupo -O-alquileno C1-3-heteroarilo opcionalmente sustituido con uno o varios grupos alquilo C1-3, o bien Z representa un grupo -CONH-alquileno C1-5-NRaRb, o bien Z representa un grupo -CONH-alquileno C1-5-O-Rd, o bien Z representa un grupo -O-alquileno C1-3-C(O)-NRaRb, o bien Z representa un heterociclo diaminado bicíclico condensado o espiránico; Ra y Rb representan cada uno, de forma independiente el uno del otro, un átomo de H o un grupo alquilo C1-3 o -C(O)-alquilo C1-3, o bien Ra y Rb forman juntos, con el átomo de N al que están unidos, un heterociclo opcionalmente sustituido con uno o varios grupos alquilo C1-3, oxo, -NRaRb, hidroxi, alcoxi C1-3, alquileno C1-3-(OH) o -C(O)-alquilo C1-3; Rd representa un átomo de H o un grupo alquilo C1-3; Re representa un átomo de H o un grupo alquilo C1-3; en forma de base o de sal de adicion a un ácido, así como en forma de hidrato o de solvato, así como sus enantiomeros, diastereoisomeros y sus mezclas.Useful for metabolic disorders. Claim 1: Compound that responds to the general formula (1) in which: A represents a C1-4 alkylene group optionally substituted with one or more identical or different R9 groups from one another; B represents a C1-4 alkylene group optionally substituted with one or more identical or different R10 groups from one another; R9 and R10 each independently represent each other, an H atom or a C1-5 alkyl group; or R9 and R10 together form a single bond or a C1-4 alkylene group; L represents a single bond or a C1-2 alkylene group, -CH = CH- or -C ::: C-, the C1-2 alkylene groups and -CH = CH- being optionally substituted with one or more C1- alkyl substituents 2 or L represents a cycloprop-1,2-di-yl group; R represents an H atom or a C1-5 alkyl group, C1-3 fluoroalkyl, C3-6 cycloalkyl, -C (O) -C1-3 alkyl, C1-3 alkylene-C3-6 cycloalkyl, -CH2-C: :: CH, C2-4-NRaRb alkylene or C1-3-X-C1-3 alkylene in which X represents O or SO2; R1 represents an aryl or a heteroaryl; the aryl and heteroaryl groups being optionally substituted with one or several Z radicals identical or different from each other, R2 and R3 independently represent each other, an H atom or a C1-3 alkyl or C1-3 fluoroalkyl group ; or R2 and R3 together form, with the C atom that supports them, a cycloprop-1,1-di-yl group; R4 represents: an atom of H or a C1-5 alkyl group, C1-3 fluoroalkyl, C1-5 alkoxy, -SF5 or C1-3-alkylene-C1-3 alkyl in which X represents O or SO2, a group C1-5-NRaRb alkylene, an aryl or a heteroaryl; the aryl and heteroaryl groups being optionally substituted with one or several Z radicals identical or different from each other; R5 represents an H or halogen atom or a C1-5 alkyl group, C1-3 fluoroalkyl, C1-5 alkoxy, C3-6 cycloalkyl, C1-3 alkylene-C3-6 cycloalkyl, C1-3-O-alkyl alkylene C1-3, C1-3- alkylene (OH) or C1-3 alkylene-C1-3 alkyl in which X represents S, SO or SO2, or R5 represents a group -NRaRb, C1-3 alkylene-NRaRb , aryl, C1-3-aryl alkylene, -O-aryl, C1-3-O-aryl alkylene, C1-3-O-C1-3-aryl alkylene, heteroaryl or C1-3-heteroaryl alkylene; the aryl, C1-3-aryl alkylene, -O-aryl, C1-3-O-aryl alkylene, C1-3-O-C1-3-alkylene-aryl, heteroaryl and C1-3-heteroaryl optionally substituted groups being optionally with one or more identical or different Z radicals from each other, or R5 represents a heterocycle group, said heterocycle being optionally substituted with a C1-3 alkyl group, -C (O) -C1-3 alkyl, -C (O) -C1-3 fluoroalkyl, C1-3 alkylene-C3-6 cycloalkyl, C1-3-aryl alkylene or C1-3-heteroaryl alkylene; the C1-3-aryl alkylene and C1-3 alkylene heteroaryl groups being optionally substituted with one or more identical Z radicals different from each other; R7 represents an H or halogen atom or a C1-5 alkyl, C1-3 fluoroalkyl, C1-5 alkoxy, -COOH, -C (O) O-C1-3 alkyl, C1-3 fluoroalkoxy, C1- alkylene 3- (OH), -NO2, -CN or -X-C1-3alkyl in which X represents S, SO or SO2, or R7 represents a group -NRaRb, C1-3 alkylene-NRaRb, -C (O ) - NRaRb, -C (O) -C1-3alkyl, aryl, -O-aryl or heteroaryl; the aryl, -O-aryl and heteroaryl groups being optionally substituted with one or more identical or different Z radicals from each other; Z represents a halogen atom or a C1-5 alkyl group, C1-3 fluoroalkyl, C3-6 cycloalkyl, C1-3 alkylene-C3-6 cycloalkyl, a phenyl, C1-5 alkoxy, C1-3 fluoroalkoxy, C1- alkylene 3-O-C1-3 alkyl, C1-3 alkylene- (OH), NO2, -CN, -SO2NRaRb, -X-C1-3 alkyl or C1-3 alkylene-X-C1-3 alkyl in which X represents S, SO or SO2, or Z represents a phenyl optionally substituted with a halogen atom, a C1-5 alkyl, C1-5 alkoxy or C1-3 fluoroalkyl group, or Z represents an alkynyl radical of the type -C :: : C-Rc, in which Rc represents an atom of H, a C1-3 alkyl group, C1-6-O-Rd alkylene or C1-6-NRaRb alkylene, or Z represents a C4-6 alkylene group ORd, either Z represents a tetrazol group substituted with a C1-3 alkyl group, or Z represents a group -NRaRb, C1-6 alkylene-NRaRb or -C (O) -NRaRb, -C (O) -C1 alkyl -3, -C (O) -O-C1-4alkyl, -C (O) -C3-6cycloalkyl, or Z represents an oxo radical, or Z represents a C1-5-NRaRb -O-alkylene group or either two adjacent Z radicals together form a C1-3-dioxy alkylene group; Either Z represents a -0-C0-3 alkylene-heterocycle group, optionally substituted with one or more C1-3 alkyl, oxo or -C (O) -C1-3alkyl groups, or Z represents a -O- group C1-5-O-Rd alkylene, or Z represents a C0-3 -C-alkylene-C5-7 alkylene group optionally substituted with a -O-Rd group, or Z represents a C0-3 -N-alkylene group -heterocycle optionally substituted with one or several C1-3 alkyl, oxo or -C (O) -C1-3 alkyl groups, or Z represents a C2-5-O-Rd -NRe-alkylene group, or Z represents a -O-C1-3 alkylene-heteroaryl group optionally substituted with one or more C1-3 alkyl groups, or Z represents a -CONH-C1-5-NRaRb group, or Z represents a -CONH-C1-alkylene group 5-O-Rd, or Z represents a group -O-C1-3-C alkylene (O) -NRaRb, or Z represents a condensed or spicylic bicyclic diamine heterocycle; Ra and Rb each independently represent each other, an atom of H or a C1-3 alkyl group or -C (O) -C1-3 alkyl, or Ra and Rb form together, with the atom of N to which they are attached, a heterocycle optionally substituted with one or more C1-3 alkyl groups, oxo, -NRaRb, hydroxy, C1-3 alkoxy, C1-3 alkylene- (OH) or -C (O) -C1 alkyl 3; Rd represents an atom of H or a C1-3 alkyl group; Re represents an H atom or a C1-3 alkyl group; in the form of base or salt of addition to an acid, as well as in the form of hydrate or solvate, as well as its enantiomers, diastereoisomers and mixtures thereof.

ARP060104457A 2005-10-12 2006-10-11 DERIVATIVES OF THE 4- AMINO - QUINAZOLINA ITS PREPARATION AND ITS APPLICATION IN THERAPEUTICS AR056688A1 (en)

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WO (1) WO2007042669A2 (en)

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