JP5468068B2 - ジベンゾチアゼピン誘導体及びその使用 - Google Patents
ジベンゾチアゼピン誘導体及びその使用 Download PDFInfo
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- JP5468068B2 JP5468068B2 JP2011514540A JP2011514540A JP5468068B2 JP 5468068 B2 JP5468068 B2 JP 5468068B2 JP 2011514540 A JP2011514540 A JP 2011514540A JP 2011514540 A JP2011514540 A JP 2011514540A JP 5468068 B2 JP5468068 B2 JP 5468068B2
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- compound
- fluoro
- formula
- dibenzo
- thiazepine
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- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229950005135 traxoprodil Drugs 0.000 description 1
- 229960003991 trazodone Drugs 0.000 description 1
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
- 229950002464 trepipam Drugs 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
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- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
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- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 description 1
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
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- 230000000007 visual effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
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Classifications
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- 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
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- 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
- A61P25/18—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D281/16—[b, f]-condensed
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
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| US7441708P | 2008-06-20 | 2008-06-20 | |
| US61/074,417 | 2008-06-20 | ||
| PCT/SE2009/050763 WO2009154563A1 (en) | 2008-06-20 | 2009-06-18 | Dibenzothiazepine derivatives and use thereof |
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| JP2014011979A Division JP2014098006A (ja) | 2008-06-20 | 2014-01-27 | ジベンゾチアゼピン誘導体及びその使用 |
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| JP2011524898A JP2011524898A (ja) | 2011-09-08 |
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| JP2011514540A Expired - Fee Related JP5468068B2 (ja) | 2008-06-20 | 2009-06-18 | ジベンゾチアゼピン誘導体及びその使用 |
| JP2014011979A Pending JP2014098006A (ja) | 2008-06-20 | 2014-01-27 | ジベンゾチアゼピン誘導体及びその使用 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2014011979A Pending JP2014098006A (ja) | 2008-06-20 | 2014-01-27 | ジベンゾチアゼピン誘導体及びその使用 |
Country Status (37)
Cited By (1)
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| JP2014098006A (ja) * | 2008-06-20 | 2014-05-29 | Astrazeneca Ab | ジベンゾチアゼピン誘導体及びその使用 |
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| CN105981027A (zh) * | 2013-08-12 | 2016-09-28 | 哥莱菲特软件公司 | 安全认证并切换至加密域 |
| CN103524455A (zh) * | 2013-10-30 | 2014-01-22 | 苏州敬业医药化工有限公司 | 一种制备2-氯-二苯并[b,f][1,4]硫氮杂卓-11-[10H]酮的方法 |
| CA2931289C (en) | 2013-11-21 | 2023-10-17 | Graphite Software Corporation | Managed domains for remote content and configuration control on mobile information devices |
| CN104447615A (zh) * | 2014-02-28 | 2015-03-25 | 广东东阳光药业有限公司 | 喹硫平中间体的制备方法 |
| EP4428132A1 (en) * | 2023-03-08 | 2024-09-11 | Johann-Wolfgang-Goethe-Universität Frankfurt am Main | Slack-activating compounds and their medical use |
| JP2026509430A (ja) * | 2023-03-08 | 2026-03-19 | ヨハン ヴォルフガング ゲーテ－ウニベルジテート フランクフルト アム マイン | Ｓｌａｃｋ活性化化合物及びその医学的用途 |
Family Cites Families (69)
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| DE1620703B2 (de) * | 1960-08-16 | 1976-11-25 | Ausscheidung aus: 12 80 879 Dr. A. Wander AG, Bern | 11-basisch substituierte dibenzo eckige klammer auf b,f eckige klammer zu-eckige klammer auf 1,4 eckige klammer zu-thiazepine |
| CH422793A (de) | 1961-07-20 | 1966-10-31 | Wander Ag Dr A | Verfahren zur Herstellung 11-basisch substituierter Dibenzo(b,f) (1,4)thiazepine |
| CH476753A (de) | 1962-06-08 | 1969-08-15 | Wander Ag Dr A | Verfahren zur Herstellung von 11-basisch substituierter Dibenzo(b,f)(1,4)thiazepine |
| DE1470416A1 (de) | 1962-05-25 | 1969-05-14 | Wander Ag Dr A | Verfahren zur Herstellung ll-basisch substituierter 5 H-Dibenzo[b,e],[1,4] diazepine |
| NL140242B (nl) | 1963-03-01 | 1973-11-15 | Wander Ag Dr A | Werkwijze voor het bereiden van op de 11-plaats door een basische groep gesubstitueerde dibenz (b.f.)(1.4) oxazepinen. |
| NL293210A (https=) | 1963-05-09 | |||
| US3884920A (en) | 1967-07-14 | 1975-05-20 | Sandoz Ag | 11-Basically substituted dibenz {8 b,f{9 {0 {8 1,4{9 {0 oxazepines |
| US3683034A (en) | 1963-09-27 | 1972-08-08 | Upjohn Co | Process for the preparation of substituted hydroquinones |
| US3908010A (en) | 1967-03-22 | 1975-09-23 | Wander Ag Dr A | Basically substituted heterocycles as anti-emetics |
| US3412193A (en) | 1965-12-13 | 1968-11-19 | American Cyanamid Co | 11-(4-methyl-1-piperazinyl)dibenz[b, f][1, 4]oxazepines or thiazepines for controlling fertility |
| AT278805B (de) | 1966-01-17 | 1970-02-10 | American Cyanamid Co | Verfahren zur herstellung von oxazepinen und thiazepinen |
| NL6715650A (https=) | 1966-12-16 | 1968-06-17 | ||
| US3852446A (en) | 1967-03-13 | 1974-12-03 | Sandoz Ag | Organic compounds in treatment of psychotic disturbances |
| US3758479A (en) | 1967-03-22 | 1973-09-11 | Sandoz Ag | Nitro and sulphamoyl substituted dibenzodiazepines |
| US3539573A (en) | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| CH569731A5 (https=) * | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| GB8607684D0 (en) | 1986-03-27 | 1986-04-30 | Ici America Inc | Thiazepine compounds |
| GB8705574D0 (en) | 1987-03-10 | 1987-04-15 | Ici Plc | Preparation of thiazepine compound |
| JPH04211071A (ja) * | 1990-03-05 | 1992-08-03 | Hokuriku Seiyaku Co Ltd | 多環式化合物 |
| JPH0565257A (ja) | 1991-07-05 | 1993-03-19 | Hokuriku Seiyaku Co Ltd | 多環式化合物及びその用途 |
| US5750566A (en) | 1994-08-12 | 1998-05-12 | Eli Lilly And Company | Synthetic excitatory amino acids |
| ATE192157T1 (de) | 1994-08-24 | 2000-05-15 | Astra Ab | Therapeutisch verwendbare spiro-azabicyclische verbindungen |
| US5602121A (en) * | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | Alkyl-substituted compounds having dopamine receptor affinity |
| SE9504661D0 (sv) | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| AR013184A1 (es) | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9702799D0 (sv) | 1997-07-25 | 1997-07-25 | Astra Ab | New compounds |
| WO2000010572A1 (en) | 1998-08-18 | 2000-03-02 | Sepracor Inc. | Use of hydroxyrisperidone for the manufacture of a medicament for the treatment and prevention of psychoses, emesis and symptoms of withdrawal from alcohol and nicotine |
| SE9900100D0 (sv) | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| WO2001008680A1 (de) | 1999-07-28 | 2001-02-08 | Oswald Wiss | Präparate mit sauerstoffsparender wirkung bei körperlicher leistung |
| SE9903760D0 (sv) | 1999-10-18 | 1999-10-18 | Astra Ab | New compounds |
| SE0002729D0 (sv) | 2000-07-20 | 2000-07-20 | Astrazeneca Ab | Novel compound form |
| US6630462B2 (en) | 2000-11-17 | 2003-10-07 | Adolor Corporation | Delta agonist analgesics |
| IL139975A0 (en) | 2000-11-29 | 2002-02-10 | Univ Ramot | Anti proliferative drugs |
| PT1395567E (pt) | 2001-05-18 | 2009-03-26 | Astrazeneca Ab | Derivados de 4(fenil-piperazinil-metil)benzamida e sua utilização para o tratamento da ansiedade da dor ou de distúrbios gastrointestinais |
| BR0210075A (pt) | 2001-06-01 | 2004-08-17 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos de tratamento ou profilaxia de doenças ou condições humanas, de distúrbios psicóticos ou distúrbios da debilitação intelectual e de fadiga de vÈo, cessamento de fumar, dependência de nicotina, dores, e para a colite ulcerativa |
| HRP20040102A2 (en) | 2001-07-09 | 2004-10-31 | Combinatorx | Combinations for the treatment of inflammatory disorders |
| ES2379544T3 (es) | 2001-09-27 | 2012-04-27 | Ramot At Tel Aviv University Ltd. | Conjugado de perfenazina y GABA y usos del mismo |
| US7544681B2 (en) | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| ES2348282T3 (es) | 2002-04-18 | 2010-12-02 | Astrazeneca Ab | Compuestos de tienilo. |
| US7417049B2 (en) | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
| NZ561993A (en) | 2002-04-18 | 2008-09-26 | Astrazeneca Ab | Spiroazabicyclic heterocyclic amines as potent ligands for nicotinic acetylcholine receptors |
| SE0202430D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| SE0202465D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| SE0202598D0 (sv) | 2002-09-02 | 2002-09-02 | Astrazeneca Ab | Alpha-7 Nicotinic receptor agonists and statins in combination |
| EP1538906A2 (en) | 2002-09-18 | 2005-06-15 | Fmc Corporation | Insecticidal tricyclic derivatives |
| JP2006510697A (ja) * | 2002-12-20 | 2006-03-30 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺虫性ジベンゾ（ヘテロ）アゼピン誘導体 |
| JP2006515628A (ja) | 2003-01-23 | 2006-06-01 | アカディア ファーマシューティカルズ，インコーポレーテッド | ヒト神経精神疾患を処置するためのｎ−デスメチルクロザピンの使用 |
| CN1777594A (zh) | 2003-02-22 | 2006-05-24 | 特瓦制药工业有限公司 | 喹迪平及其可药用盐的合成 |
| DE10310196A1 (de) | 2003-03-06 | 2004-09-23 | Rina-Netzwerk Rna Technologien Gmbh | Verwendung eines trizyklischen Antidepressivums zur Förderung der Endozytose |
| DE602004012083T2 (de) | 2003-04-15 | 2009-04-23 | Astrazeneca Ab | Neue Verbindungen, die als Verstärker von Glutamatrezeptoren dienen |
| US20060217366A1 (en) * | 2003-07-02 | 2006-09-28 | Astrazeneca Ab | Method of treating schizophrenia and other disorders |
| PL195728B1 (pl) | 2003-07-18 | 2007-10-31 | Helm Ag | Sposób wytwarzania 11-(1-piperazynylo)dibenzo[b,f][1,4]tiazepiny |
| RU2394030C2 (ru) * | 2003-12-22 | 2010-07-10 | Акадиа Фармасьютикалз Инк. | АМИНОЗАМЕЩЕННЫЕ АНАЛОГИ ДИАРИЛ [a,d] ЦИКЛОГЕПТЕНА В КАЧЕСТВЕ МУСКАРИНОВЫХ АГОНИСТОВ И СПОСОБЫ ЛЕЧЕНИЯ ПСИХОНЕВРОЛОГИЧЕСКИХ РАССТРОЙСТВ |
| PT1696931E (pt) * | 2003-12-22 | 2009-06-12 | Acadia Pharm Inc | Análogos diaril[a,d]ciclo-hepteno substituídos com amino utilizados como agonistas muscarínicos e métodos de tratamento de perturbações neuropsiquiátricas |
| US20060063754A1 (en) * | 2004-09-21 | 2006-03-23 | Edgar Dale M | Methods of treating a sleep disorder |
| JP2008525478A (ja) | 2004-12-27 | 2008-07-17 | アストラゼネカ アクチボラグ | 神経系及び精神医学系障害の治療のための代謝共役型グルタミン酸受容体アゴニストとしてのピラゾロン化合物 |
| JP2008526839A (ja) * | 2005-01-07 | 2008-07-24 | アストラゼネカ・アクチエボラーグ | １１−ピペラジン−１−イルジベンゾ［ｂ，ｆ］［１，４］チアゼピン又はその薬学的に許容される塩の新規な使用及び経口医薬組成物への新規な使用 |
| AU2006231497A1 (en) * | 2005-04-04 | 2006-10-12 | Acadia Pharmaceuticals Inc. | Use of N-desmethylclozapine and related compounds as dopamine stabilizing agents |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| EP2099459A4 (en) | 2006-12-20 | 2011-04-27 | Astrazeneca Ab | COMPOUNDS AND USES THEREOF |
| EP2114940A1 (en) | 2007-02-09 | 2009-11-11 | AstraZeneca AB | Aza-isoindolones and their use as metabotropic glutamate receptor potentiators - 613 |
| US7491871B2 (en) | 2007-04-25 | 2009-02-17 | Stine Seed Farm, Inc. | Soybean cultivar S060299 |
| 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 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
| CN102131791B (zh) * | 2008-06-20 | 2014-12-24 | 阿斯利康(瑞典)有限公司 | 二苯并硫杂氮杂*衍生物及其用途 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014098006A (ja) * | 2008-06-20 | 2014-05-29 | Astrazeneca Ab | ジベンゾチアゼピン誘導体及びその使用 |
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