ES2315853T3 - Tetrahidroquinolinonas y su uso como antagonistas de receptores de glutamato metabotropico. - Google Patents

Tetrahidroquinolinonas y su uso como antagonistas de receptores de glutamato metabotropico. Download PDF

Info

Publication number
ES2315853T3
ES2315853T3 ES05717798T ES05717798T ES2315853T3 ES 2315853 T3 ES2315853 T3 ES 2315853T3 ES 05717798 T ES05717798 T ES 05717798T ES 05717798 T ES05717798 T ES 05717798T ES 2315853 T3 ES2315853 T3 ES 2315853T3
Authority
ES
Spain
Prior art keywords
aryl
6alkyl
dihydro
heteroaryl
6alkoxy
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
ES05717798T
Other languages
English (en)
Inventor
Christopher Graham Raphael Parsons
Aigars Jirgensons
Ieva Jaunzeme
Ivars Kalvinsh
Markus Henrich
Maksims Vanejevs
Tanja Weil
Valerjans Kauss
Wojciech Danysz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merz Pharma GmbH and Co KGaA
Original Assignee
Merz Pharma GmbH and Co KGaA
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 Merz Pharma GmbH and Co KGaA filed Critical Merz Pharma GmbH and Co KGaA
Application granted granted Critical
Publication of ES2315853T3 publication Critical patent/ES2315853T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • 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
    • A61P1/08—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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • 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
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • 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
    • A61P25/22—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/34—Tobacco-abuse
    • 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
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/16—Otologicals
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D215/20—Oxygen atoms
    • 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
    • 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
    • C07D215/36—Sulfur atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • 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
    • C07D401/04—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
    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
    • 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
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
    • C07D409/04—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
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D417/02—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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D417/02—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
    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Addiction (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Reproductive Health (AREA)
  • Otolaryngology (AREA)
  • Vascular Medicine (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compuesto de la fórmula IA ** ver fórmula** en donde R 2 representa C2-6alquilo, cicloC3-12alquilo, cicloC3-12alquilC1-6alquilo, C2-6alquenilo, C2-6alquinilo, arilo, biarilo, aril-heteroarilo, heteroaril-heteroarilo, heteroaril-arilo, aril-C1-6alquilo, aril-C2-6alquenilo, aril-C2-6alquinilo, heteroarilo, heteroaril-C1-6alquilo, heteroaril-C2-6alquenilo, heteroaril-C2-6alquinilo, 2,3-dihidro-1H-indenilo, C2-6alcoxi, hidroxi-C2-6alcoxi, cicloC3-12alcoxi, cicloC3-12alquilC1-6alcoxi, ariloxi, aril-C1-6alcoxi, C1-6alcoxi-C1-6alquilo, C1-6alquiltio, C4-6alqueniltio, cicloC3-12alquiltio, cicloC3-12alquil-C1-6alquiltio, cicloC3-12alquil-C3-6alqueniltio, C1-6alcoxi-C1-6alquiltio, C1-6alcoxi-C3-6alqueniltio, aril-C3-6alqueniltio, heteroaril-C1-6alquiltio, C1-6alquilsulfonilo, cicloC3-12alquil-C1-6alquilsulfonilo, arilC16alquilsulfonilo, C1-6alquilamino, di-C1- 6alquilamino, cicloC3-12alquilamino, C1-6alcoxi-cicloC3-12alquilamino, cicloC3-12alquil-C16alquilamino, di-C1-6 alquilamino-C1-6alquilo, C1-6alcoxi-C2-6alquilamino, arilamino, aril-lC1-6alquilamino, N-cicloC3-12alquil-N-C1- 6alquilamino, N-aril-N-C1-6alquilamino, N-arilC1-6alquil-N-C1-6alquilamino, 2indanilamino, 1,2,3,4-tetrahidroisoquinolin-2-ilo, tetrahidrofurilo,pirrolidino, piperidino, 4-arilpiperidino, 4-heteroarilpiperidino, morfolino, piperazino, 4-C1-6alquilpiperazino, 4-arilpiperazino, hexametilenimino, benzazepinilo, 1,3-dihidro-2H-isoindol-2-ilo, heteroaril- C1-6alcoxi, heteroarilamino, heteroaril-C1-6alquilamino, NHC(=O)-R 11 , -NHSO2-R 11 , -NHC(=O)OR 11 , -C(=O)NH- R 11 , o -C16alquil-C(=O)NH-R 11 , R 3 representa hidrógeno, ciano, nitro, halógeno, C1-6alquilo,CF3, heteroarilo, 2,3dihidro-1H-indenilo, hidroxi, C1-6alcoxi, pirrolidino, piperidino, o morfolino; R 4 representa hidrógeno, halógeno, nitro, C1-6alcoxi, o hidroxi-C2-6 alcoxi; R 5 y R 6 , los cuales pueden ser los mismos o diferentes, representan cada uno independientemente hidrógeno, hidroxi, C1-6alquilo, cicloC3-12alquilo, C2-6alquenilo, C1-6alcoxi, C1-6alcoxi-C1-6alquilo, C1-6alquiltio, C3-6alqueniltio, C1-6 alquilamino, di-C1-6alquilamino, cicloC3-12alquilamino, di-C1-6 alquilamino-C1-6alquilo, aril-C1- 6alquilamino, arilo, aril-C1-6alquilo, o aril-C2-6alquenilo; R 7 y R 8 , los cuales pueden ser los mismos o diferentes, representan cada uno independientemente hidrógeno, C1-6alquilo, cicloC3-12alquilo, C2-6alquenilo, cicloC3-12 alquil-C1-6alquilo, arilo, aril-C1-6alquilo, heteroarilo, o heteroaril-C1-6alquilo; o pueden representar juntos -(CH2)m- con m siendo 4, ó 6; o uno de R5 y R6 y uno de R7 y R8 juntos representan -(CH2)n- siendo n 3, 4 o 5, mientras que el resto de R5 y R6 así como R7 y R8 son ambos hidrógeno; R 9 y R 10 , los cuales pueden ser los mismos o diferentes, representan cada uno independientemente hidrógeno, C1- 6alquilo, hidroxi, o C1-6alcoxi; R 11 representa hidrógeno, C1-6alquilo, C2-6alquenilo, arilo, aril-C1-6alquilo, aril-C2-6alquenilo, heteroarilo, heteroaril-C1-6alquilo, C16alquilamino, di-C1-6alquilamino, cicloC3-12alquilamino, di-C16alquilamino-C1-6alquilo, arilamino, aril-C1-6alquilamino, aril-C26alquenilamino, N-aril-N-C1-6 alquilamino, pirrolidino, piperidino, morfolino, hexametilenimino, benzazepinilo, 1,3-dihidro-2H-isoindol-2ilo, cicloC3-12alquilo, o cicloC3-12alquilC1-6alquilo, R 12 representa hidrógeno, C1-6alquilo, arilo, heteroarilo, arilC1-6alquilo o heteroaril-C1-6alquilo; Entendiéndose que los grupos alquilo, alquenilo y alquinilo pueden ser rectos o ramificados; los grupos cicloC3- 12alquilo pueden ser monocíclicos, bicíclicos o tricíclicos y en el caso de porciones cicloC3-12alquilo dentro de R2 y R11 pueden ser opcionalmente no saturados y/o tener un átomo de carbono reemplazado por un átomo de oxígeno o una porción NR12; el término "arilo" denota fenilo o naftilo no sustituidos o naftilo o fenilo sustituidos con uno o más sustituyentes R13 seleccionados entre halógeno, trifluorometilo, C1-6alquilo, C2-6alquenilo, C1-6alcoxi, amino, hidroxi, nitro, ciano, cianometilo, C1-6alcoxicarbonilo, C1-6 alquilamino, di-C1-6alquilamino, piperidinilo, morfolinilo y piridilo; el término "biarilo" denota bifenileno donde uno o ambos anillos fenilo pueden opcionalmente portar uno o más R14 donde R14 es como se definió para R13 pero excluye cianometilo; el término "heteroarilo" denota un anillo aromático de ó 6 miembros comprendiendo 1-4 heteroátomos seleccionados entre oxígeno, azufre y nitrógeno el cual está opcionalmente fusionado con un anillo benceno o un anillo de a miembros adicional que comprende de 1-4 heteroátomos seleccionados entre oxígeno, azufre y nitrógeno, y que opcionalmente porta uno o más sustituyentes R donde R es como se definió para R14 pero incluye adicionalmente arilo; y el término "halógeno" denota flúor, cloro, bromo y yodo; siendo entendido que: i) R 2 no puede representar fenilo o naftilo no sustituido; ii) R 2 no puede representar fenilo sustituido que tenga al menos un sustituyente orto que no sea hidrógeno, en relación al anillo de tetrahidroquinolina de la fórmula IA al cual esté unido el fenilo; iii) R 2 no puede representar dimetilamino; iv) si uno de R 5 y R 6 y uno de R 7 y R 8 representan juntos (CH2)n- con n siendo 3, 4 ó 5, mientras que el resto de R 5 y R 6 así como R 7 y R 8 son ambos hidrógeno, entonces R 2 también pueden ser halógeno; v) si R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 y R 10 representan todos hidrógeno al mismo tiempo, entonces R 2 no puede representar C2-6alquilo; vi) si R 3 es ciano, entonces R 2 no puede representar metiltio o etiltio; vii) R 7 y R 8 no pueden representar furilo; y viii) el compuesto de la fórmula IA no puede representar: 2-Benciloxi-7,8-dihidro-6H-quinolin-5-ona, 2-Fenoxi- 7,8dihidro-6H-quinolin-5-ona, 2-(1H-Indol-3-il)-7,8-dihidro-6H-quinolin-5ona, 2-(1H-Indol-3-il)-7,7-dimetil-7,8-dihidro-6H-quinolin-5-ona, 25 Tiofen-2-il-7,8-dihidro-6H-quinolin-5-ona, 2-Etoxi-7,8-dihidro-6Hquinolin-5-ona, 7,7- Dimetil-2-(6-metil-piridin-3-ilmetilsulfanil)-5-oxo5,6,7,8-tetrahidroquinolin-3-carbonitrilo, 2-(1H-Benzoimidazol-2 ilmetilsulfanil)-7,7-dimetil-5-oxo-5,6,7,8-tetrahidroquinolin-3carbonitrilo, 2-(4-Metoxi-fenil)-7,8-dihidro-6H-quinolin-5-ona, 2-(4Cloro-fenil)-7,7-dimetil-7,8-dihidro-6H-quinolin-5-ona, 2-(4-Fluorofenil)-7,8-dihidro-6H-quinolin-5ona, 2-(4-Isopropil-fenil)-5-oxo5,6,7,8-tetrahidroquinolin-3-carbonitrilo, o 2-Ciclohexil-7,8-dihidro-6Hquinolin-5ona, 2-(m-tolil)-7,8-dihidro-6H-quinolin-5-ona, 2-(3-methoxifenil)-7,8-dihidro-6H-quinolin-5-ona, 2-(4-clorofenil)- 7,8-dihidro-6H-quinolin-5-ona, 2-[4-(1-metiletil)fenil]-7,8-dihidro-6H-quinolin-5-ona, 2-piridin-2-il-7,8-dihidro-6Hquinolin-5-ona o 2-etoxi-7,7-dimetil-7,8-dihidro-6H-quinolin-5-ona; e isómeros ópticos, polimorfos y sales de adición ácidas y básicas, hidratos y solvatos farmacéuticamente aceptables de los mismos.
ES05717798T 2004-02-27 2005-02-25 Tetrahidroquinolinonas y su uso como antagonistas de receptores de glutamato metabotropico. Expired - Lifetime ES2315853T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US54878804P 2004-02-27 2004-02-27
US548788P 2004-02-27

Publications (1)

Publication Number Publication Date
ES2315853T3 true ES2315853T3 (es) 2009-04-01

Family

ID=34911013

Family Applications (1)

Application Number Title Priority Date Filing Date
ES05717798T Expired - Lifetime ES2315853T3 (es) 2004-02-27 2005-02-25 Tetrahidroquinolinonas y su uso como antagonistas de receptores de glutamato metabotropico.

Country Status (23)

Country Link
US (1) US7598384B2 (es)
EP (1) EP1723116B1 (es)
JP (1) JP4712027B2 (es)
KR (1) KR100846347B1 (es)
CN (1) CN1922146A (es)
AR (1) AR049006A1 (es)
AT (1) ATE409182T1 (es)
AU (1) AU2005217199B2 (es)
BR (1) BRPI0508225A (es)
CA (1) CA2556653C (es)
DE (1) DE602005009929D1 (es)
DK (1) DK1723116T3 (es)
EA (1) EA010656B1 (es)
ES (1) ES2315853T3 (es)
IL (1) IL177524A (es)
PL (1) PL1723116T3 (es)
PT (1) PT1723116E (es)
SI (1) SI1723116T1 (es)
TW (1) TWI301760B (es)
UA (1) UA83549C2 (es)
UY (1) UY28775A1 (es)
WO (1) WO2005082856A2 (es)
ZA (1) ZA200606686B (es)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007023242A1 (en) * 2005-08-24 2007-03-01 Merz Pharma Gmbh & Co. Kgaa Tetrahydroquinolinones and their use as modulators of metabotropic glutamate receptors
WO2007023245A1 (en) * 2005-08-25 2007-03-01 Merz Pharma Gmbh & Co. Kgaa Tetrahydroquinolinones and their use as modulators of metabotropic glutamate receptors
JP2009506069A (ja) 2005-08-26 2009-02-12 ブレインセルス，インコーポレイティド ムスカリン性受容体調節による神経発生
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009512711A (ja) 2005-10-21 2009-03-26 ブレインセルス，インコーポレイティド Ｐｄｅ阻害による神経新生の調節
AU2006303037A1 (en) * 2005-10-21 2007-04-26 Merz Pharma Gmbh & Co Kgaa Chromenones and their use as modulators of metabotropic glutamate receptors
EP2314289A1 (en) 2005-10-31 2011-04-27 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
TW200732313A (en) * 2005-12-15 2007-09-01 Astrazeneca Ab Oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
CA2651862A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. 5 ht receptor mediated neurogenesis
AU2007249399A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
WO2008030651A1 (en) 2006-09-08 2008-03-13 Braincells, Inc. Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
EP2102165A2 (en) * 2006-11-24 2009-09-23 AC Immune S.A. N-(methyl)-1h-pyrazol-3-amine, n-(methyl)-pyridin-2-amine and n-(methyl)-thiazol-2-amine derivatives for the treatment of diseases associated with amyloid or amyloid-like proteins, like e.g. alzheimer's
MX2011004680A (es) * 2008-11-06 2011-05-25 Astrazeneca Ab Moduladores de beta amiloide.
US20100216805A1 (en) 2009-02-25 2010-08-26 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
UY32622A (es) * 2009-05-12 2010-12-31 Astrazeneca Ab Nuevos compuestos para el tratamiento de patologías relacionadas con ab(beta)
EP2311823A1 (en) 2009-10-15 2011-04-20 AC Immune S.A. 2,6-Diaminopyridine compounds for treating diseases associated with amyloid proteins or for treating ocular diseases
EA019980B1 (ru) 2009-12-18 2014-07-30 Янссен Фармацевтика Нв БИЦИКЛИЧЕСКИЕ ТИАЗОЛЫ В КАЧЕСТВЕ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR5
CN102666551B (zh) 2009-12-18 2014-12-10 詹森药业有限公司 作为mglur5受体的变构调节剂的双环噻唑
GB0922589D0 (en) * 2009-12-23 2010-02-10 Almac Discovery Ltd Pharmaceutical compounds
WO2012052451A1 (en) 2010-10-18 2012-04-26 Merz Pharma Gmbh & Co. Kgaa Metabotropic glutamate receptor modulators
MX2013005545A (es) * 2010-11-16 2013-08-01 Ge Healthcare Ltd Compuestos heterociclicos como sodas de imagenologia de la patologia tau.
WO2012139876A1 (en) 2011-04-14 2012-10-18 Merz Pharma Gmbh & Co. Kgaa Enteric formulations of metabotropic glutamate receptor modulators
KR20150047609A (ko) * 2012-08-30 2015-05-04 니뽄 신야쿠 가부시키가이샤 피리딘 유도체 및 의약
AU2014211727B2 (en) 2013-02-04 2018-07-26 Prexton Therapeutics Sa Positive allosteric modulators of mGluR3
CN104513200B (zh) * 2013-09-26 2017-05-03 江苏苏中药业集团股份有限公司 取代丁烯酰胺的马来酸盐及其晶型
TWI713455B (zh) 2014-06-25 2020-12-21 美商伊凡克特治療公司 ＭｎＫ抑制劑及其相關方法
DK3294713T5 (da) 2015-05-15 2021-05-31 Aurigene Discovery Tech Ltd Substituerede tetrahydroquinolinonforbindelser som ror-gamma-modulatorer
SG11201803242TA (en) * 2015-10-29 2018-05-30 Effector Therapeutics Inc Isoindoline, azaisoindoline, dihydroindenone and dihydroazaindenone inhibitors of mnk1 and mnk2
WO2017087808A1 (en) 2015-11-20 2017-05-26 Effector Therapeutics, Inc. Heterocyclic compounds that inhibit the kinase activity of mnk useful for treating various cancers
WO2017189553A1 (en) * 2016-04-25 2017-11-02 Everon Biosciences, Inc. Removal of senescence-associated macrophages
WO2018152117A1 (en) 2017-02-14 2018-08-23 Effector Therapeutics, Inc. Piperidine-substituted mnk inhibitors and methods related thereto
US11130757B2 (en) 2018-10-24 2021-09-28 Effector Therapeutics Inc. Crystalline forms of MNK inhibitors
GB2600384A (en) 2020-09-30 2022-05-04 Vaderis Therapeutics Ag Allosteric AKT inhibitors for use in the treatment of hereditary hemorrhagic telangiectasia
IL317852A (en) * 2022-06-23 2025-02-01 Cleveland Clinic Found 3-βHSD1 inhibitors and compositions and uses thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3501479A (en) * 1967-05-19 1970-03-17 American Cyanamid Co Dihydroquinolines and substituted dihydroquinolines and method of preparing the same
DE2001572A1 (de) 1970-01-15 1971-07-22 Agfa Gevaert Ag Spektral sensibilisiertes lichtempfindliches Material
DE2449030A1 (de) 1974-10-11 1976-05-20 Schering Ag Neue pyridin-derivate
WO1988002251A1 (en) 1986-09-26 1988-04-07 Ici Australia Operations Proprietary Limited Sunscreen compositions and compounds for use therein
US5216164A (en) * 1990-12-03 1993-06-01 Hoechst-Roussel Pharmaceuticals Incorporated 5-amino-5,6,7,8-tetrahydroquinolines and related compounds
US5110815A (en) * 1990-12-03 1992-05-05 Hoechst-Roussel Pharmaceuticals Inc. 5-amino-5,6,7,8-tetrahydroquinolines and related compounds and pharmaceutical use
AU4481899A (en) * 1998-02-20 1999-09-06 Takeda Chemical Industries Ltd. Aminoguanidine hydrazone derivatives, process for producing the same and drugs thereof
GB0003632D0 (en) 2000-02-16 2000-04-05 Univ Hong Kong Science & Techn Dimeric compounds
SK5212003A3 (en) * 2000-10-02 2004-03-02 Janssen Pharmaceutica Nv Metabotropic glutamate receptor antagonists
MXPA04009435A (es) 2002-03-29 2005-01-25 Janssen Pharmaceutica Nv Derivados de quinolina y quinolinona radiomarcados y su uso como ligandos de receptor de glutamato metabotropico.

Also Published As

Publication number Publication date
UA83549C2 (uk) 2008-07-25
CA2556653C (en) 2011-08-16
ZA200606686B (en) 2008-01-30
PT1723116E (pt) 2009-01-02
BRPI0508225A (pt) 2007-07-17
IL177524A (en) 2012-02-29
WO2005082856A2 (en) 2005-09-09
DK1723116T3 (da) 2009-02-02
EA200601556A1 (ru) 2007-02-27
UY28775A1 (es) 2005-04-29
PL1723116T3 (pl) 2009-04-30
TWI301760B (en) 2008-10-11
AU2005217199B2 (en) 2008-06-26
CA2556653A1 (en) 2005-09-09
IL177524A0 (en) 2006-12-10
ATE409182T1 (de) 2008-10-15
WO2005082856A3 (en) 2005-11-24
EP1723116B1 (en) 2008-09-24
AR049006A1 (es) 2006-06-21
EP1723116A2 (en) 2006-11-22
JP4712027B2 (ja) 2011-06-29
US7598384B2 (en) 2009-10-06
KR20070001975A (ko) 2007-01-04
SI1723116T1 (sl) 2009-04-30
CN1922146A (zh) 2007-02-28
US20050197361A1 (en) 2005-09-08
EA010656B1 (ru) 2008-10-30
AU2005217199A1 (en) 2005-09-09
TW200534857A (en) 2005-11-01
KR100846347B1 (ko) 2008-07-15
DE602005009929D1 (de) 2008-11-06
JP2007524710A (ja) 2007-08-30

Similar Documents

Publication Publication Date Title
ES2315853T3 (es) Tetrahidroquinolinonas y su uso como antagonistas de receptores de glutamato metabotropico.
AR052902A1 (es) Derivados de piridazina, composicion farmaceutica que los contiene y su uso como agentes terapeuticos para enfermedades mediadas por la estearoil-coa desaturasa
CO5570668A2 (es) Derivados triciclicos sustituidos de himbacina que son antagonistas del receptor de trombina y composiciones farmaceuticas que los contienen
AR042206A1 (es) Acidos fenilaceticos y derivados
AR037682A1 (es) Derivados de acetileno que tienen actividad antagonista para receptores glutamato metabotropico humanos, composicion farmaceutica, una combinacion y el uso de dichos derivados para la fabricacion de composiciones farmaceuticas
CO4650033A1 (es) Derivados de lactama con actividad selectiva agonista y antagonista de receptores de serotonina 1 (5ht) y composiciones farmaceuticas que los contienen .
AR040694A1 (es) Derivados de benzodioxol como antagonistas de los receptores cb1
AR048289A1 (es) Eteres de anillos imidazo sulfona sustituidos.
PE20020508A1 (es) DERIVADOS DE PIRIDINA COMO INHIBIDORES DE LA ACTIVIDAD DE LA QUINASA IkB ß
AR034009A1 (es) Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos
CR10145A (es) Derivados de tropano útiles en terapia (divisional exp. 6800)
AR053301A1 (es) Derivados de pirazina y su uso farmaceutico
PE20021094A1 (es) Derivados de ciclohexano-1,4-diamina sustituidos
AR025975A1 (es) Compuestos quimicos.
AR015712A1 (es) Derivados de 3,4-dihidro-tieno[2,3-d]pirimidina-3-sustituidos y su uso para la preparacion de composiciones farmaceuticas
AR054021A1 (es) Derivados de ciclopentapiridina y tetrahidroquinolina
ES2195933T3 (es) Nuevos derivados de flavonas, xantonas y cumarinas.
AR046745A1 (es) Uso de derivados de amidrazonas para combatir pestes
AR027744A1 (es) Compuestos de eter difenilico utiles en terapia
AR061835A1 (es) Derivados tetraciclicos, su procedimiento de preparacion y las composiciones farmaceuticas que los contienen
PE20242216A1 (es) Compuestos de heteroaril-urea novedosos como inhibidores de kv7.2
AR034206A1 (es) Un procedimiento para la preparacion de mesilatos de derivados de piperazina y dichos mesilatos
PE20061127A1 (es) Derivados de propanosulfonamida que potencian el receptor de glutamato
AR046106A1 (es) Derivados de 2-(4-sulfonilamino) -3-hidroxi-3,4-dihidro-2h-cromen-6-ilosustituidos con amidometilo procedimiento y productos intermedios para su preparacion y medicamentos que contienen a estos compuestos
AR044470A1 (es) Derivados de pirrol sustituidos