TWI301760B - Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors - Google Patents

Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors Download PDF

Info

Publication number
TWI301760B
TWI301760B TW094105679A TW94105679A TWI301760B TW I301760 B TWI301760 B TW I301760B TW 094105679 A TW094105679 A TW 094105679A TW 94105679 A TW94105679 A TW 94105679A TW I301760 B TWI301760 B TW I301760B
Authority
TW
Taiwan
Prior art keywords
dihydro
quinolin
dimethyl
keto
group
Prior art date
Application number
TW094105679A
Other languages
English (en)
Chinese (zh)
Other versions
TW200534857A (en
Inventor
Aigars Jirgensons
Christopher Graham Raphael Parsons
Ieva Jaunzeme
Ivars Kalvinsh
Markus Henrich
Maksims Vanejevs
Tanja Weil
Valerjans Kauss
Wojciech Danysz
Original Assignee
Merz Pharma Gmbh & 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 & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa
Publication of TW200534857A publication Critical patent/TW200534857A/zh
Application granted granted Critical
Publication of TWI301760B publication Critical patent/TWI301760B/zh

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)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Ophthalmology & Optometry (AREA)
  • Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Child & Adolescent Psychology (AREA)
  • Reproductive Health (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Vascular Medicine (AREA)
  • Otolaryngology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
TW094105679A 2004-02-27 2005-02-24 Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors TWI301760B (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number Publication Date
TW200534857A TW200534857A (en) 2005-11-01
TWI301760B true TWI301760B (en) 2008-10-11

Family

ID=34911013

Family Applications (1)

Application Number Title Priority Date Filing Date
TW094105679A TWI301760B (en) 2004-02-27 2005-02-24 Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors

Country Status (23)

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

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
EP1943247A1 (en) * 2005-08-25 2008-07-16 Merz Pharma GmbH & Co.KGaA Tetrahydroquinolinones and their use as modulators of metabotropic glutamate receptors
US7678363B2 (en) 2005-08-26 2010-03-16 Braincells Inc Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs
EP2258359A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis by muscarinic receptor modulation with sabcomelin
CA2620248A1 (en) * 2005-10-21 2007-04-26 Merz Pharma Gmbh & Co. Kgaa Chromenones and their use as modulators of metabotropic glutamate receptors
WO2007047978A2 (en) 2005-10-21 2007-04-26 Braincells, Inc. Modulation of neurogenesis by pde inhibition
AU2006308889A1 (en) 2005-10-31 2007-05-10 Braincells, Inc. GABA receptor mediated modulation of neurogenesis
AR057218A1 (es) * 2005-12-15 2007-11-21 Astra Ab Compuestos de oxazolidinona y su uso como pontenciadores del receptor metabotropico de glutamato
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
CA2651813A1 (en) 2006-05-09 2007-11-22 Braincells, Inc. Neurogenesis by modulating angiotensin
WO2007134077A2 (en) 2006-05-09 2007-11-22 Braincells, Inc. 5 ht receptor mediated neurogenesis
CA2662491A1 (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
KR101450356B1 (ko) 2006-11-24 2014-10-15 에이씨 이뮨 에스.에이. 알츠하이머와 같은 아밀로이드 또는 아밀로이드-유사 단백질과 관련된 질환의 치료를 위한 ｎ-(메틸)-1ｈ-피라졸-3-아민, ｎ-(메틸)-피리딘-2-아민 및 ｎ-(메틸)-티아졸-2-아민 유도체
KR20110082189A (ko) * 2008-11-06 2011-07-18 아스트라제네카 아베 아밀로이드 베타의 조절제
WO2010099217A1 (en) 2009-02-25 2010-09-02 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
WO2011073347A1 (en) 2009-12-18 2011-06-23 Janssen Pharmaceutica Nv Bicyclic thiazoles as allosteric modulators of mglur5 receptors
ES2431302T3 (es) 2009-12-18 2013-11-25 Janssen Pharmaceutica, N.V. Tiazoles bicíclicos como moduladores alostéricos de receptores mGluR5
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
US9040021B2 (en) * 2010-11-16 2015-05-26 Ge Healthcare Limited Heterocyclic compounds as imaging probes of tau pathology
WO2012139876A1 (en) 2011-04-14 2012-10-18 Merz Pharma Gmbh & Co. Kgaa Enteric formulations of metabotropic glutamate receptor modulators
BR112015004284A2 (pt) * 2012-08-30 2017-07-04 Nippon Shinyaku Co Ltd derivado de piridina e medicina
CA2899954A1 (en) * 2013-02-04 2014-08-07 Merck Patent Gmbh 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
JP6684516B2 (ja) 2015-05-15 2020-04-22 オーリジーン ディスカバリー テクノロジーズ リミテッドＡｕｒｉｇｅｎｅ Ｄｉｓｃｏｖｅｒｙ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｌｉｍｉｔｅｄ Ｒｏｒガンマ調節物質としての置換型テトラヒドロキノリン化合物
MX2018005204A (es) 2015-10-29 2018-08-01 Effector Therapeutics Inc Inhibidores de isoindolina, azaisoindolina, dihidroindenona y dihidroazaindenona de cinasas 1 y 2 de interaccion con proteina cinasas activadas por mitogenos (mnk1 y 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
PE20191349A1 (es) 2017-02-14 2019-09-30 Effector Therapeutics Inc Inhibidores de mnk sustituidos con piperidina y metodos relacionados con los mismos
CA3117169A1 (en) 2018-10-24 2020-04-30 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
CA3260514A1 (en) * 2022-06-23 2023-12-28 The Cleveland Clinic Foundation 3.BETA.HSD1 INHIBITORS AND THEIR COMPOSITIONS AND USES

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
CA2316944A1 (en) * 1998-02-20 1999-08-26 Mitsuru Shiraishi Aminoguanidinehydrazone derivative, production and use 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
BR0308945A (pt) * 2002-03-29 2005-01-04 Janssen Pharmaceutica Nv Derivados radiomarcados de quinolina e quinolinona e uso dos mesmos como ligantes para receptores de glutamato metabotrópicos

Also Published As

Publication number Publication date
KR100846347B1 (ko) 2008-07-15
EA010656B1 (ru) 2008-10-30
IL177524A (en) 2012-02-29
JP4712027B2 (ja) 2011-06-29
PL1723116T3 (pl) 2009-04-30
WO2005082856A2 (en) 2005-09-09
KR20070001975A (ko) 2007-01-04
AR049006A1 (es) 2006-06-21
US20050197361A1 (en) 2005-09-08
DE602005009929D1 (de) 2008-11-06
ATE409182T1 (de) 2008-10-15
AU2005217199A1 (en) 2005-09-09
EP1723116A2 (en) 2006-11-22
EA200601556A1 (ru) 2007-02-27
UY28775A1 (es) 2005-04-29
BRPI0508225A (pt) 2007-07-17
SI1723116T1 (sl) 2009-04-30
TW200534857A (en) 2005-11-01
CN1922146A (zh) 2007-02-28
JP2007524710A (ja) 2007-08-30
EP1723116B1 (en) 2008-09-24
CA2556653A1 (en) 2005-09-09
WO2005082856A3 (en) 2005-11-24
IL177524A0 (en) 2006-12-10
UA83549C2 (uk) 2008-07-25
ZA200606686B (en) 2008-01-30
CA2556653C (en) 2011-08-16
PT1723116E (pt) 2009-01-02
AU2005217199B2 (en) 2008-06-26
ES2315853T3 (es) 2009-04-01
US7598384B2 (en) 2009-10-06
DK1723116T3 (da) 2009-02-02

Similar Documents

Publication Publication Date Title
TWI301760B (en) Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors
TWI399376B (zh) 經取代之吡唑並嘧啶類，製備彼等之方法及彼等作為藥物之用途
JP2863629B2 (ja) 置換ベンゾ〔５，６〕シクロヘプタピリジンの複素環式ｎ―オキシド誘導体、組成物およびその使用法
TWI329635B (en) Tetrahydroquinolinones and their use as modulators of metabotropic glutamate receptors
JP2013501013A (ja) 代謝調節型グルタミン酸受容体モジュレーター
TW201100428A (en) Substituted indolo-piperidine compounds
TW201035055A (en) Substituted 5,6-dihydro-6-phenylbenzo[f]isoquinolin-2-amine compounds
TW200819458A (en) Metabotropic glutamate receptor modulators
TW201201813A (en) Substituted benzo-pyrido-triazolo-diazepine compounds
TW200845985A (en) Quinolines
TW201100398A (en) Substituted indolo-pyridinone compounds
TW201124381A (en) Novel hydroxy-6-heteroarylphenanthridines
TW200902006A (en) Fast dissociating dopamine 2 receptor antagonists
WO2006033318A1 (ja) 環状アミン誘導体又はその塩
MX2007015678A (es) Antagonistas y agonistas de piperazina-piperidina del receptor 5-ht-1a.
NL2000336C2 (nl) Spirocyclische derivaten.
JPH037257A (ja) ピリジン誘導体及びそれを有効成分とする向精神剤
TW200808730A (en) Process for synthesizing piperazine-piperidine compounds
CN111343978A (zh) 新型盐
US7550482B2 (en) Tetrahydroquinolones and their use as modulators of metabotropic glutamate receptors
MXPA06009564A (en) Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors
TW201307301A (zh) 趨代謝性麩胺酸受體調節劑
JP2004231514A (ja) ５−ｈｔ７受容体結合能を有し、かつ代謝的に安定なテトラヒドロベンズインドール誘導体
HU204256B (en) Process for producing quinoline-2,5-dions and pharmaceutical compositions containing them
TW201305110A (zh) 促代謝性麩胺酸受體調節劑

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees