JP2010529118A - オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 - Google Patents
オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 Download PDFInfo
- Publication number
- JP2010529118A JP2010529118A JP2010511147A JP2010511147A JP2010529118A JP 2010529118 A JP2010529118 A JP 2010529118A JP 2010511147 A JP2010511147 A JP 2010511147A JP 2010511147 A JP2010511147 A JP 2010511147A JP 2010529118 A JP2010529118 A JP 2010529118A
- Authority
- JP
- Japan
- Prior art keywords
- disorder
- pain
- pharmaceutically acceptable
- compound according
- solvate
- 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.)
- Granted
Links
- 0 CC(C(C(CN1Cc(cc2)ccc2Cl)=C2)C1=O)C=C2C(O)=NC(CC1CCNCCC1)=*I Chemical compound CC(C(C(CN1Cc(cc2)ccc2Cl)=C2)C1=O)C=C2C(O)=NC(CC1CCNCCC1)=*I 0.000 description 1
- DGWACMVUKBKAGU-UHFFFAOYSA-N Cc(cc(cc1CN2Cc(cc3)ccc3Cl)-c3nc(CCl)n[o]3)c1C2=O Chemical compound Cc(cc(cc1CN2Cc(cc3)ccc3Cl)-c3nc(CCl)n[o]3)c1C2=O DGWACMVUKBKAGU-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P25/36—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
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- 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
-
- 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
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
Abstract
Description
Qは
R2は水素またはC1-3アルキルである]
の化合物、またはその薬学的に許容しうる塩、水和物、溶媒和物、光学異性体または混合物を提供する。
本明細書において、特に断りがなければ、本明細書で使用される命名は一般に「Nomenclature of Organic Chemistry、Section A、B、C、D、E、F and H」, Pergamon出版社, オックスフォード(1979年)に記載の例および規則に従い、それは化学構造式の名称および化学構造式を命名する際の規則に関して参照により本明細書に加入される。場合により、化合物名は化学命名プログラム:ACD/ChemSketch, バージョン5.09/2001年9月, Advanced Chemistry Development社(カナダ国トロント)を使用して名付けることができる。
Qは
R2は水素またはC1-3アルキルである]
の化合物、またはその薬学的に許容しうる塩、水和物、溶媒和物、光学異性体または混合物を示す。
式Iの化合物は本明細書で例示されたような様々な合成法により製造することができる。したがって、特定の構造特性および/または置換基の選択は、他の方法に優先して一つの方法を選ぶ際に影響を与える。
(b) MeCN(50mL)中における7−メチル−1−オキソ−2−(置換−ベンジル)−2,3−ジヒドロ−1H−イソインドール−5−カルボニルクロライド(100ミリモル)の溶液に2−クロロ−N−ヒドロキシアセトアミジン(110ミリモル)およびK2CO3(200ミリモル)を加えた。混合物を一晩攪拌し、次に水で希釈し、EtOAcで抽出した。有機相をブラインで洗浄し、乾燥(Na2SO4)し、ろ過し、濃縮した。残留物をDMF(50mL)に溶解し、3.5時間加熱還流した。冷却した溶液を水で希釈し、EtOAcで抽出した。有機相をブラインで洗浄し、乾燥(Na2SO4)し、ろ過し、濃縮した。シリカ上のカラムクロマトグラフィー(10〜35%のEtOAc/ヘキサン)により処理して2−置換−ベンジル−5−(3−クロロメチル−[1,2,4]オキサジアゾール−5−イル)−7−メチル−2,3−ジヒドロ−イソインドール−1−オンを得た。
(c) MeCN中における2−(置換−ベンジル)−5−(3−クロロメチル−[1,2,4]オキサジアゾール−5−イル)−7−メチル−2,3−ジヒドロ−イソインドール−1−オン(100ミリモル)の溶液にK2CO3(200〜300ミリモル)および適当なアミン(QH、150〜200ミリモル)を加えた。混合物を加熱して所望のイソインドロンを得、それをシリカ上のカラムクロマトグラフィー(MeOH/CH2Cl2中の1〜5% 2M NH3)により精製した。
Boc−保護中間体をCH2Cl2(15mL)に溶解し、1:1のTFA/CH2Cl2(40mL)を加えた。45分後、反応混合物を濃縮し、NaHCO3水溶液でpH約9〜10に塩基性にした。生成物をCH2Cl2で抽出した。有機相をブラインで洗浄し、乾燥(Na2SO4)し、ろ過し、濃縮した。シリカ上のカラムクロマトグラフィー(MeOH/CH2Cl2中の1〜5% 2M NH3)により処理して7−メチル−5−(5−ピペラジン−1−イルメチル−[1,2,4]オキサジアゾール−3−イル)−2−(4−トリフルオロメトキシベンジル)−2,3−ジヒドロイソインドール−1−オン(3.79g)を無色の泡状物として得た。1H NMR (300MHz, CDCl3)δ8.05 (s, 1H), 8.00 (s, 1H), 7.36 (d, 2H), 7.20 (d, 2H), 4.81 (s, 2H), 4.33 (s, 2H), 3.77 (s, 2H), 2.94−3.05 (m, 4H), 2.84 (s, 3H), 2.61 (br s, 4H)。
本明細書で開示される化合物は一般に式Iの化合物またはその薬学的に許容しうる塩または溶媒和物を薬学的に許容しうる担体または賦形剤と一緒に含有する医薬組成物に製剤化することができる。薬学的に許容しうる担体は固体または液体である。固体形態の製剤には粉末、錠剤、分散性顆粒剤、カプセル剤、カシェ剤および坐剤があるが、それらに限定されない。
本明細書で開示される化合物は代謝型グルタミン酸受容体の調節物質として活性を示し、特にmGluR2受容体の増強剤として活性を示す。本化合物は特に動物、とりわけヒトのグルタミン酸機能障害と関係がある神経疾患および精神疾患を治療するための薬剤として治療において有用であると考えられる。
出発物質は商業的に入手できるか、または文献に記載されている。
Claims (18)
- R1はクロロまたはトリフルオロメトキシルである請求項1記載の化合物またはその薬学的に許容しうる塩、水和物、溶媒和物、光学異性体。
- R1はトリフルオロメトキシルである請求項2記載の化合物またはその薬学的に許容しうる塩、水和物、溶媒和物、光学異性体。
- 7−メチル−5−(3−ピペラジン−1−イルメチル−[1,2,4]オキサジアゾール−5−イル)−2−(4−トリフルオロメトキシベンジル)−2,3−ジヒドロイソインドール−1−オン;
2−(4−クロロ−ベンジル)−5−[3−(2,5−ジアザ−ビシクロ[2.2.1]へプタ−2−イルメチル)−[1,2,4]オキサジアゾール−5−イル]−7−メチル−2,3−ジヒドロ−イソインドール−1−オン;
2−(4−クロロ−ベンジル)−7−メチル−5−[3−(3−メチル−ピペラジン−1−イルメチル)−[1,2,4]オキサジアゾール−5−イル]−2,3−ジヒドロ−イソインドール−1−オン;
2−(4−クロロ−ベンジル)−7−メチル−5−(3−ピペラジン−1−イルメチル−[1,2,4]オキサジアゾール−5−イル)−2,3−ジヒドロ−イソインドール−1−オン;
2−(4−クロロ−ベンジル)−7−メチル−5−[3−(2−メチル−ピペラジン−1−イルメチル)−[1,2,4]オキサジアゾール−5−イル]−2,3−ジヒドロ−イソインドール−1−オンまたは
2−(4−クロロ−ベンジル)−7−メチル−5−[3−(2−メチル−ピペラジン−1−イルメチル)−[1,2,4]オキサジアゾール−5−イル]−2,3−ジヒドロ−イソインドール−1−オンから選択される請求項1記載の化合物。 - 請求項1〜10の何れか1項記載の化合物および薬学的に許容しうる担体または賦形剤を含有する医薬組成物。
- 薬剤として使用される請求項1〜10の何れか1項記載の化合物。
- グルタミン酸機能障害と関係がある神経疾患および精神疾患を治療するための薬剤の製造における請求項1〜10の何れか1項記載の化合物の使用。
- 神経疾患および精神疾患は心臓バイパス手術および移植後の脳傷害、卒中、脳虚血、脊髄損傷、頭部外傷、周生期低酸素症、心停止、低血糖性神経損傷、認知症、AIDSによる認知症、アルツハイマー病、ハンチントン舞踏病、筋萎縮性側索硬化症、眼損傷、網膜症、認知障害、特発性および薬剤性パーキンソン病、筋肉けいれん、振戦を含む筋痙直と関係がある疾患、てんかん、けいれん、長期てんかん重積症後の脳傷害、偏頭痛、片頭痛、尿失禁、薬物耐性、薬物離脱、精神病、統合失調症、不安症、全般性不安障害、パニック障害、対人恐怖症、強迫性障害、外傷後ストレス障害(PTSD)、気分障害、鬱病、躁病、双極性障害、概日リズム障害、時差ぼけ、交代勤務睡眠障害、三叉神経痛、難聴、耳鳴り、眼の黄斑変性症、脳浮腫、疼痛、急性疼痛、慢性疼痛、激痛、難治性疼痛、神経障害性疼痛、炎症性疼痛、外傷後疼痛、遅発性ジスキネジー、睡眠障害、ナルコレプシー、注意欠陥/多動性障害および行為障害から選択される請求項13記載の使用。
- そのような治療が必要な動物に治療的に有効な量の請求項1〜10の何れか1項記載の化合物を投与する段階を含む前記動物のグルタミン酸機能障害と関係がある神経疾患および精神疾患を治療または予防する方法。
- そのような治療が必要な動物に治療的に有効な量の請求項11記載の医薬組成物を投与する段階を含む前記動物のグルタミン酸機能障害と関係がある神経疾患および精神疾患を治療または予防する方法。
- 神経疾患および精神疾患は心臓バイパス手術および移植後の脳傷害、卒中、脳虚血、脊髄損傷、頭部外傷、周生期低酸素症、心停止、低血糖性神経損傷、認知症、AIDSによる認知症、アルツハイマー病、ハンチントン舞踏病、筋萎縮性側索硬化症、眼損傷、網膜症、認知障害、特発性および薬剤性パーキンソン病、筋肉けいれん、振戦を含む筋痙直と関係がある疾患、てんかん、けいれん、長期てんかん重積症後の脳傷害、偏頭痛、片頭痛、尿失禁、薬物耐性、薬物離脱、精神病、統合失調症、不安症、全般性不安障害、パニック障害、対人恐怖症、強迫性障害、外傷後ストレス障害(PTSD)、気分障害、鬱病、躁病、双極性障害、概日リズム障害、時差ぼけ、交代勤務睡眠障害、三叉神経痛、難聴、耳鳴り、眼の黄斑変性症、脳浮腫、疼痛、急性疼痛、慢性疼痛、激痛、難治性疼痛、神経障害性疼痛、炎症性疼痛、外傷後疼痛、遅発性ジスキネジー、睡眠障害、ナルコレプシー、注意欠陥/多動性障害および行為障害から選択される請求項15または16記載の方法。
- 神経疾患および精神疾患はアルツハイマー病、長期てんかん重積症後の脳傷害、薬物耐性、薬物離脱、精神病、統合失調症、不安症、全般性不安障害、パニック障害、対人恐怖症、強迫性障害、外傷後ストレス障害(PTSD)、気分障害、鬱病、躁病および双極性障害から選択される請求項17記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US94255307P | 2007-06-07 | 2007-06-07 | |
US60/942,553 | 2007-06-07 | ||
PCT/SE2008/050666 WO2008150233A1 (en) | 2007-06-07 | 2008-06-05 | Oxadiazole derivatives and their use as metabotropic glutamate receptor potentiators - 842 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013235538A Division JP5815644B2 (ja) | 2007-06-07 | 2013-11-14 | オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010529118A true JP2010529118A (ja) | 2010-08-26 |
JP2010529118A5 JP2010529118A5 (ja) | 2011-07-07 |
JP5416696B2 JP5416696B2 (ja) | 2014-02-12 |
Family
ID=40093925
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010511147A Expired - Fee Related JP5416696B2 (ja) | 2007-06-07 | 2008-06-05 | オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 |
JP2013235538A Expired - Fee Related JP5815644B2 (ja) | 2007-06-07 | 2013-11-14 | オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013235538A Expired - Fee Related JP5815644B2 (ja) | 2007-06-07 | 2013-11-14 | オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 |
Country Status (34)
Country | Link |
---|---|
US (2) | US8377940B2 (ja) |
EP (2) | EP2167502B3 (ja) |
JP (2) | JP5416696B2 (ja) |
KR (2) | KR20150116907A (ja) |
CN (2) | CN101679403B (ja) |
AR (1) | AR066882A1 (ja) |
AU (1) | AU2008260717B2 (ja) |
BR (1) | BRPI0812889A2 (ja) |
CA (1) | CA2690856C (ja) |
CL (1) | CL2008001667A1 (ja) |
CO (1) | CO6251287A2 (ja) |
CY (2) | CY1113422T1 (ja) |
DK (2) | DK2444399T3 (ja) |
EC (1) | ECSP109856A (ja) |
ES (2) | ES2531443T3 (ja) |
HK (2) | HK1166978A1 (ja) |
HR (2) | HRP20120909T4 (ja) |
IL (1) | IL202158A (ja) |
ME (1) | ME01488B (ja) |
MX (1) | MX2009013078A (ja) |
MY (1) | MY158066A (ja) |
NZ (1) | NZ582445A (ja) |
PE (1) | PE20090328A1 (ja) |
PL (2) | PL2444399T3 (ja) |
PT (2) | PT2167502E (ja) |
RS (2) | RS53845B1 (ja) |
RU (2) | RU2470931C2 (ja) |
SA (1) | SA08290344B1 (ja) |
SI (2) | SI2167502T1 (ja) |
TW (1) | TWI417100B (ja) |
UA (1) | UA99129C2 (ja) |
UY (1) | UY31124A1 (ja) |
WO (1) | WO2008150233A1 (ja) |
ZA (1) | ZA200908285B (ja) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7807706B2 (en) * | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
US7868008B2 (en) * | 2005-08-12 | 2011-01-11 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
TW200804281A (en) * | 2006-02-16 | 2008-01-16 | Astrazeneca Ab | New metabotropic glutamate receptor-potentiating isoindolones |
AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
PT2203439E (pt) | 2007-09-14 | 2011-02-11 | Ortho Mcneil Janssen Pharm | 4-fenil-3,4,5,6-tetra-hidro-2h,1'h-[1,4']bipiridinil-2'- onas 1',3'-dissubstituídas |
JP5433579B2 (ja) | 2007-09-14 | 2014-03-05 | ジャンセン ファーマシューティカルズ, インコーポレイテッド. | 1,3−二置換−4−フェニル−1h−ピリジン−2−オン |
NZ584152A (en) | 2007-09-14 | 2011-11-25 | Ortho Mcneil Janssen Pharm | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
MX2010005110A (es) * | 2007-11-14 | 2010-09-09 | Ortho Mcneil Janssen Pharm | Derivados de imidazo[1,2-a]piridina y su uso como moduladores alostericos positivos de los receptores de glutamato metabotropico 2. |
SA109300358B1 (ar) * | 2008-06-06 | 2012-11-03 | استرازينيكا ايه بي | مقويات مستقبل جلوتامات ذي انتحاء أيضي من أيزو إندولون |
MY157518A (en) | 2008-06-20 | 2016-06-15 | Astrazeneca Ab | Dibenzothiazepine derivatives and use thereof |
BRPI0918055A2 (pt) | 2008-09-02 | 2015-12-01 | Addex Pharmaceuticals Sa | derivados de 3-azabiciclo[3,1,0]hexila como moduladores de receptores metabotrópicos de glutamato. |
CA2738849C (en) | 2008-10-16 | 2016-06-28 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
JP5690277B2 (ja) | 2008-11-28 | 2015-03-25 | ジャンセン ファーマシューティカルズ, インコーポレイテッド. | 代謝型グルタミン酸受容体の調節因子としてのインドールおよびベンゾオキサジン誘導体 |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
NZ596078A (en) | 2009-05-12 | 2013-06-28 | Janssen Pharmaceuticals Inc | 1,2,4-TRIAZOLO [4,3-a] PYRIDINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OR PREVENTION OF NEUROLOGICAL AND PSYCHIATRIC DISORDERS |
CN102439015B (zh) | 2009-05-12 | 2015-05-13 | 杨森制药有限公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物和其作为mGluR2受体的正向变构调节剂的用途 |
WO2011084098A1 (en) * | 2010-01-07 | 2011-07-14 | Astrazeneca Ab | Process for making a metabotropic glutamate receptor positive allosteric modulator - 874 |
CA2795218A1 (en) * | 2010-04-30 | 2011-11-03 | Helen Blade | Polymorphs of a metabotropic glutamate receptor positive allosteric modulator |
US8993591B2 (en) | 2010-11-08 | 2015-03-31 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors |
US9271967B2 (en) | 2010-11-08 | 2016-03-01 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
CA2814998C (en) | 2010-11-08 | 2019-10-29 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
CN102180872B (zh) * | 2011-04-01 | 2014-04-02 | 华中科技大学 | [1,3,4]噁二唑类衍生物及其应用 |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
SI3096790T1 (sl) | 2014-01-21 | 2019-11-29 | Janssen Pharmaceutica Nv | Kombinacije, ki vsebujejo pozitivne aleostrične modulatorje ali ortosterične agoniste metabotropnega glutamatergičnega receptorja podtipa 2 in njihova uporaba |
AU2016297362B2 (en) | 2015-07-17 | 2020-04-16 | Takeda Pharmaceutical Company Limited | Oxadiazole derivatives useful as HDAC inhibitors |
EP3327019A4 (en) * | 2015-07-17 | 2019-04-03 | Takeda Pharmaceutical Company Limited | HETEROCYCLIC CONNECTION |
US10406146B2 (en) | 2015-08-25 | 2019-09-10 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
US11161838B2 (en) | 2018-11-13 | 2021-11-02 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
US11078204B2 (en) | 2018-11-13 | 2021-08-03 | Incyte Corporation | Heterocyclic derivatives as PI3K inhibitors |
US11396502B2 (en) | 2018-11-13 | 2022-07-26 | Incyte Corporation | Substituted heterocyclic derivatives as PI3K inhibitors |
BR112022000811A2 (pt) * | 2019-07-18 | 2022-03-29 | Abaxys Therapeutics | Formulação sólida de um derivado de 1,2,4-oxadiazol |
GB2621323A (en) | 2022-08-03 | 2024-02-14 | Sirgartan Holdings Ltd | Treatments for obsessive compulsive disorder |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006020879A1 (en) * | 2004-08-13 | 2006-02-23 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
WO2007021309A1 (en) * | 2005-08-12 | 2007-02-22 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
Family Cites Families (40)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2008803A (en) * | 1932-04-18 | 1935-07-23 | Stephan Engineering Corp | Fuel atomizing and igniting means |
US3993617A (en) * | 1975-10-30 | 1976-11-23 | Morton-Norwich Products, Inc. | Antifungal 2-substituted phthalimidines |
US5175157A (en) * | 1985-11-27 | 1992-12-29 | Boehringer Ingelheim Gmbh | Cyclic amine derivatives, pharmaceutical compositions containing these compounds and methods for preparing them |
WO1992017448A1 (en) | 1991-04-01 | 1992-10-15 | Kyowa Hakko Kogyo Co., Ltd. | 3-methyleneisoindolin-1-one derivative |
TW219935B (ja) | 1991-12-25 | 1994-02-01 | Mitsubishi Chemicals Co Ltd | |
EP0602814A1 (en) | 1992-12-18 | 1994-06-22 | Takeda Chemical Industries, Ltd. | Crystal forms of optically active isoindolines and their use |
US5681954A (en) * | 1993-05-14 | 1997-10-28 | Daiichi Pharmaceutical Co., Ltd. | Piperazine derivatives |
RU2124511C1 (ru) * | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
US6017919A (en) * | 1996-02-06 | 2000-01-25 | Japan Tobacco Inc. | Compounds and pharmaceutical use thereof |
CA2291630A1 (en) | 1997-05-30 | 1998-12-03 | Tetsutaro Niizato | Nitrogen-containing heterocyclic compounds and therapeutic agents for hyperlipidemia comprising the same |
CN1158264C (zh) | 1997-11-21 | 2004-07-21 | Nps药物有限公司 | 用于治疗中枢神经系统疾病的代谢性谷氨酸受体拮抗剂 |
RU2257384C2 (ru) * | 2000-02-29 | 2005-07-27 | Мицубиси Фарма Корпорейшн | Новые производные циклического амида |
KR20030059084A (ko) | 2000-07-31 | 2003-07-07 | 스미스크라인 비참 피.엘.시. | 카르복사미드 화합물 및 이것의 사람 11cby 수용체의길항제로서의 용도 |
JP4251872B2 (ja) * | 2001-04-19 | 2009-04-08 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 2−イミノイミダゾール誘導体(2) |
KR20040022238A (ko) | 2001-08-09 | 2004-03-11 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체 화합물 및 그 화합물을 유효성분으로서 함유하는 약제 |
AU2003226927A1 (en) | 2002-04-09 | 2003-10-27 | 7Tm Pharma A/S | Novel carboxamide compounds for use in mch receptor related disorders |
FR2840302B1 (fr) | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
DE10238865A1 (de) | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
GB0223232D0 (en) | 2002-10-07 | 2002-11-13 | Pfizer Ltd | Chemical compounds |
RU2343145C2 (ru) * | 2002-11-26 | 2009-01-10 | Маруиси Фармасьютикал Ко., Лтд. | Производные изоиндолина |
CN100457731C (zh) | 2003-03-26 | 2009-02-04 | 麦克公司 | 代谢型谷氨酸受体的苯甲酰胺调节剂 |
GB0308025D0 (en) | 2003-04-07 | 2003-05-14 | Glaxo Group Ltd | Compounds |
US7129260B2 (en) * | 2003-06-02 | 2006-10-31 | Abbott Laboratories | Isoindolinone kinase inhibitors |
CA2542220A1 (en) | 2003-10-22 | 2005-05-06 | Eli Lilly And Company | Novel mch receptor antagonists |
JP2007519754A (ja) | 2004-01-30 | 2007-07-19 | スミスクライン ビーチャム コーポレーション | 化合物 |
ES2309718T3 (es) * | 2004-02-18 | 2008-12-16 | Astrazeneca Ab | Compuestos heterociclicos condensados y su uso como antagonistas de los receptores metabotropicos para el tratamiento de trastornos gastrointestinales. |
ES2526614T3 (es) | 2004-03-05 | 2015-01-13 | Nissan Chemical Industries, Ltd. | Compuesto de benzamida sustituida con isoxazolina y agente de control de organismos nocivos |
AU2005219791B2 (en) | 2004-03-05 | 2011-06-09 | Msd K.K. | Diaryl-substituted five-membered heterocycle derivative |
SE0400970D0 (sv) | 2004-04-14 | 2004-04-14 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
CN101048157A (zh) | 2004-10-25 | 2007-10-03 | 默克公司 | 代谢型谷氨酸受体的杂环二氢茚酮增强剂 |
AU2006216917A1 (en) | 2005-02-24 | 2006-08-31 | Merck Sharp & Dohme Corp. | Benzazole potentiators of metabotropic glutamate receptors |
KR20080027463A (ko) | 2005-05-18 | 2008-03-27 | 아덱스 파마 에스에이 | 대사성 글루타메이트 수용체의 양성 알로스테릭조절자로서의 치환된 옥사디아졸 유도체 |
GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
TW200728277A (en) | 2005-06-29 | 2007-08-01 | Palau Pharma Sa | Bicyclic derivatives as P38 inhibitors |
US7868008B2 (en) * | 2005-08-12 | 2011-01-11 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
US7807706B2 (en) * | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
AU2006298829B2 (en) * | 2005-09-27 | 2011-03-03 | F. Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mGluR2 antagonists |
TW200804281A (en) * | 2006-02-16 | 2008-01-16 | Astrazeneca Ab | New metabotropic glutamate receptor-potentiating isoindolones |
TW200911255A (en) * | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
-
2008
- 2008-06-04 TW TW097120762A patent/TWI417100B/zh not_active IP Right Cessation
- 2008-06-05 PT PT08779348T patent/PT2167502E/pt unknown
- 2008-06-05 AU AU2008260717A patent/AU2008260717B2/en not_active Ceased
- 2008-06-05 SI SI200830807T patent/SI2167502T1/sl unknown
- 2008-06-05 BR BRPI0812889A patent/BRPI0812889A2/pt not_active IP Right Cessation
- 2008-06-05 RS RS20150130A patent/RS53845B1/en unknown
- 2008-06-05 PL PL11195016T patent/PL2444399T3/pl unknown
- 2008-06-05 KR KR1020157026785A patent/KR20150116907A/ko not_active Application Discontinuation
- 2008-06-05 MX MX2009013078A patent/MX2009013078A/es active IP Right Grant
- 2008-06-05 PL PL08779348T patent/PL2167502T6/pl unknown
- 2008-06-05 WO PCT/SE2008/050666 patent/WO2008150233A1/en active Application Filing
- 2008-06-05 CN CN2008800191548A patent/CN101679403B/zh not_active Expired - Fee Related
- 2008-06-05 KR KR1020097025404A patent/KR20100017640A/ko active Search and Examination
- 2008-06-05 ME MEP-2012-131A patent/ME01488B/me unknown
- 2008-06-05 MY MYPI20095187A patent/MY158066A/en unknown
- 2008-06-05 CN CN201210486921.4A patent/CN102977086B/zh not_active Expired - Fee Related
- 2008-06-05 ES ES11195016.8T patent/ES2531443T3/es active Active
- 2008-06-05 DK DK11195016T patent/DK2444399T3/en active
- 2008-06-05 RS RS20120507A patent/RS52526B2/sr unknown
- 2008-06-05 CA CA2690856A patent/CA2690856C/en not_active Expired - Fee Related
- 2008-06-05 ES ES08779348T patent/ES2393425T7/es active Active
- 2008-06-05 NZ NZ582445A patent/NZ582445A/en not_active IP Right Cessation
- 2008-06-05 RU RU2009147708/04A patent/RU2470931C2/ru not_active IP Right Cessation
- 2008-06-05 EP EP08779348.5A patent/EP2167502B3/en active Active
- 2008-06-05 JP JP2010511147A patent/JP5416696B2/ja not_active Expired - Fee Related
- 2008-06-05 SI SI200831385T patent/SI2444399T1/sl unknown
- 2008-06-05 AR ARP080102401A patent/AR066882A1/es unknown
- 2008-06-05 EP EP11195016.8A patent/EP2444399B1/en active Active
- 2008-06-05 UA UAA200911794A patent/UA99129C2/ru unknown
- 2008-06-05 DK DK08779348.5T patent/DK2167502T3/da active
- 2008-06-05 US US12/663,371 patent/US8377940B2/en not_active Expired - Fee Related
- 2008-06-05 PT PT11195016T patent/PT2444399E/pt unknown
- 2008-06-06 US US12/134,553 patent/US8377939B2/en not_active Expired - Fee Related
- 2008-06-06 PE PE2008000965A patent/PE20090328A1/es not_active Application Discontinuation
- 2008-06-06 CL CL2008001667A patent/CL2008001667A1/es unknown
- 2008-06-06 UY UY31124A patent/UY31124A1/es not_active Application Discontinuation
- 2008-06-07 SA SA08290344A patent/SA08290344B1/ar unknown
-
2009
- 2009-11-16 IL IL202158A patent/IL202158A/en not_active IP Right Cessation
- 2009-11-23 ZA ZA200908285A patent/ZA200908285B/xx unknown
- 2009-12-04 CO CO09139153A patent/CO6251287A2/es not_active Application Discontinuation
-
2010
- 2010-01-06 EC EC2010009856A patent/ECSP109856A/es unknown
- 2010-09-15 HK HK12106999.4A patent/HK1166978A1/xx not_active IP Right Cessation
- 2010-09-15 HK HK10108742.2A patent/HK1142318A1/xx not_active IP Right Cessation
-
2012
- 2012-09-25 RU RU2012141706/04A patent/RU2012141706A/ru not_active Application Discontinuation
- 2012-11-13 HR HRP20120909AT patent/HRP20120909T4/hr unknown
- 2012-11-22 CY CY20121101132T patent/CY1113422T1/el unknown
-
2013
- 2013-11-14 JP JP2013235538A patent/JP5815644B2/ja not_active Expired - Fee Related
-
2015
- 2015-02-24 HR HRP20150210TT patent/HRP20150210T1/hr unknown
- 2015-02-26 CY CY20151100204T patent/CY1116150T1/el unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006020879A1 (en) * | 2004-08-13 | 2006-02-23 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
WO2007021309A1 (en) * | 2005-08-12 | 2007-02-22 | Astrazeneca Ab | Substituted isoindolones and their use as metabotropic glutamate receptor potentiators |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5815644B2 (ja) | オキサジアゾール誘導体およびそれらの代謝型グルタミン酸受容体増強剤としての使用 | |
JP2010529117A (ja) | 代謝型グルタミン酸受容体オキサジアゾールリガンドおよびそれらの増強剤としての使用 | |
JP5815765B2 (ja) | イソオキサゾール誘導体及び代謝型グルタミン酸受容体ポテンシエーターとしてのその使用 | |
JP2009532381A (ja) | 二環式ベンズイミダゾール化合物、および代謝型グルタミン酸受容体増強剤としての該化合物の使用 | |
WO2008032191A2 (en) | Spiro-oxazolidinone compounds and their use as metabotropic glutamate receptor potentiators | |
JP2008534543A (ja) | オキサゾール部分又はチアゾリン部分を含む化合物、それらの製造方法及びそれらの使用 | |
JP2010518104A (ja) | アザ−イソインドロンおよび代謝型グルタミン酸レセプター増強剤−613としてのそれらの使用 | |
JP2009509921A (ja) | 置換イソインドロン類及び代謝調節型グルタミン酸受容体増強剤としてのその使用 | |
US20080227794A1 (en) | Metabotropic Glutamate-Receptor-Potentiating Isoindolones |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110523 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110523 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130226 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130520 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130527 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130823 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130917 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131017 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131023 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131115 |
|
LAPS | Cancellation because of no payment of annual fees |