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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- 229960002784 thioridazine Drugs 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
- 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
- 229960004045 tolterodine Drugs 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 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
- 229960001147 triclofos Drugs 0.000 description 1
- 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
- 229960002324 trifluoperazine Drugs 0.000 description 1
- 229960002431 trimipramine Drugs 0.000 description 1
- 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
- 229960002004 valdecoxib Drugs 0.000 description 1
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229960004010 zaleplon Drugs 0.000 description 1
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
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- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
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- HDOZVRUNCMBHFH-UHFFFAOYSA-N zotepine Chemical compound CN(C)CCOC1=CC2=CC=CC=C2SC2=CC=C(Cl)C=C12 HDOZVRUNCMBHFH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (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)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011524898A JP2011524898A (ja) | 2011-09-08 |
| JP2011524898A5 JP2011524898A5 (enExample) | 2012-07-19 |
| JP5468068B2 true JP5468068B2 (ja) | 2014-04-09 |
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106134230A (zh) | 2013-11-21 | 2016-11-16 | 哥莱菲特软件公司 | 用于移动信息设备上的远程内容和配置控制的管理域 |
| 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 |
| CN120981447A (zh) * | 2023-03-08 | 2025-11-18 | 法兰克福大学 | Slack激活化合物及其医学用途 |
| EP4428132A1 (en) * | 2023-03-08 | 2024-09-11 | Johann-Wolfgang-Goethe-Universität Frankfurt am Main | Slack-activating compounds and their medical use |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL293201A (enExample) | ||||
| NL294355A (enExample) | ||||
| 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 |
| DE1620713A1 (de) * | 1962-05-25 | 1970-07-02 | Wander Ag Dr A | Verfahren zur Herstellung von 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 |
| 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 (enExample) | 1963-05-09 | |||
| US3908010A (en) | 1967-03-22 | 1975-09-23 | Wander Ag Dr A | Basically substituted heterocycles as anti-emetics |
| US3683034A (en) | 1963-09-27 | 1972-08-08 | Upjohn Co | Process for the preparation of substituted hydroquinones |
| 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 |
| 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 |
| US3444169A (en) | 1966-01-17 | 1969-05-13 | American Cyanamid Co | Process for 11 - aminodibenz(b,f)(1,4)oxazepines and analogous thiazepines |
| NL6715650A (enExample) | 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 |
| CH569731A5 (enExample) * | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| 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 |
| US5661184A (en) | 1994-08-12 | 1997-08-26 | Eli Lilly And Company | Psychiatric agents |
| CZ289512B6 (cs) | 1994-08-24 | 2002-02-13 | Astra Aktiebolag | Spiro-azabicyklické sloučeniny pouľitelné při terapii |
| 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 |
| US6342488B1 (en) | 1998-08-18 | 2002-01-29 | Sepracor, Inc. | Phosphonorisperidone and sulforisperidone compositions and methods |
| 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 |
| AU2002249885A1 (en) | 2000-11-17 | 2002-08-12 | Adolor Corporation | Delta agonist analgesics |
| IL139975A0 (en) | 2000-11-29 | 2002-02-10 | Univ Ramot | Anti proliferative drugs |
| ES2319876T3 (es) | 2001-05-18 | 2009-05-14 | Astrazeneca Ab | Derivados de 4 (fenil-piperazinil-metil) benzamida y su uso para el tratamiento de la ansiedad o trastornos gastrointestinales. |
| SI1397366T1 (sl) | 2001-06-01 | 2007-06-30 | Astrazeneca Ab | Nov ligand za nikotinske acetilholinske receptorje, koristen v terapiji |
| ES2330837T3 (es) | 2001-07-09 | 2009-12-16 | Combinatorx, Incorporated | Combinaciones para el tratamiento de trastornos inflamatorios. |
| US7544681B2 (en) | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| KR100996239B1 (ko) | 2001-09-27 | 2010-11-23 | 바-일란 유니버시티 | 접합된 항-정신병 약물 및 그의 용도 |
| US7417049B2 (en) | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
| EP1499616B1 (en) | 2002-04-18 | 2009-06-17 | AstraZeneca AB | Heterocyclic compounds |
| DE60333746D1 (de) | 2002-04-18 | 2010-09-23 | Astrazeneca Ab | Thienylverbindungen |
| 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 |
| CN1681388A (zh) | 2002-09-18 | 2005-10-12 | Fmc有限公司 | 三环衍生物杀虫剂 |
| EP1578198A1 (en) | 2002-12-20 | 2005-09-28 | Basf Aktiengesellschaft | Pesticidal dibenzo(hetero)azepine derivatives |
| MXPA05007784A (es) | 2003-01-23 | 2005-09-30 | Acadia Pharm Inc | Empleo de la n-desmetilclozapina para tratar las enfermedades neuropsiquiatricas humanas. |
| EP1495008A1 (en) | 2003-02-22 | 2005-01-12 | Teva Pharmaceutical Industries Limited | Synthesis of quetiapine and pharmaceutically acceptable salts thereof |
| DE10310196A1 (de) | 2003-03-06 | 2004-09-23 | Rina-Netzwerk Rna Technologien Gmbh | Verwendung eines trizyklischen Antidepressivums zur Förderung der Endozytose |
| JP2006523707A (ja) | 2003-04-15 | 2006-10-19 | アストラゼネカ アクツィエボラーグ | 治療化合物 |
| 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 |
| WO2006071730A1 (en) | 2004-12-27 | 2006-07-06 | Astrazeneca Ab | Pyrazolone compounds as metabotropic glutamate receptor agonists for the treatment of neurological and psychiatric disorders |
| WO2006073360A1 (en) * | 2005-01-07 | 2006-07-13 | Astrazeneca Ab | NEW USE OF 11-PIPERAZIN-1-YLDIBENZO [b,f] [1,4] THIAZEPINE OR ITS PHARMACEUTICALLY ACCEPTABLE SALT AND TO ORAL PHARMACEUTICAL COMPOSITIONS |
| EP1865962A2 (en) * | 2005-04-04 | 2007-12-19 | Arcadia 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 |
| WO2008079847A1 (en) | 2006-12-20 | 2008-07-03 | Astrazeneca Ab (Se/Se) | Compounds and uses thereof |
| WO2008100715A1 (en) | 2007-02-09 | 2008-08-21 | 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 |
| TWI488854B (zh) * | 2008-06-20 | 2015-06-21 | Astrazeneca Ab | 二苯并噻氮呯衍生物及其用途 |
-
2009
- 2009-06-18 TW TW098120494A patent/TWI488854B/zh not_active IP Right Cessation
- 2009-06-18 ME MEP-2013-27A patent/ME01516B/me unknown
- 2009-06-18 PT PT97669535T patent/PT2307389E/pt unknown
- 2009-06-18 KR KR1020117001427A patent/KR20110019781A/ko not_active Ceased
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| Publication number | Priority date | Publication date | Assignee | Title |
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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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