KR20110019781A - 디벤조티아제핀 유도체 및 그의 용도 - Google Patents
디벤조티아제핀 유도체 및 그의 용도 Download PDFInfo
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- KR20110019781A KR20110019781A KR1020117001427A KR20117001427A KR20110019781A KR 20110019781 A KR20110019781 A KR 20110019781A KR 1020117001427 A KR1020117001427 A KR 1020117001427A KR 20117001427 A KR20117001427 A KR 20117001427A KR 20110019781 A KR20110019781 A KR 20110019781A
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- South Korea
- Prior art keywords
- disorder
- pharmaceutically acceptable
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- DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 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
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
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- 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
- 229960004010 zaleplon Drugs 0.000 description 1
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- 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
- 229960001366 zolazepam Drugs 0.000 description 1
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- 229960001475 zolpidem Drugs 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)
- 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)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7441708P | 2008-06-20 | 2008-06-20 | |
| US61/074,417 | 2008-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110019781A true KR20110019781A (ko) | 2011-02-28 |
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Family Applications (1)
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2307389T3 (pl) * | 2008-06-20 | 2013-05-31 | Astrazeneca Ab | Pochodne dibenzotiazepiny i ich zastosowanie |
| WO2015021548A1 (en) * | 2013-08-12 | 2015-02-19 | Graphite Software Corporation | Secure authentication and switching to encrypted domains |
| 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 |
| EP3072320A4 (en) | 2013-11-21 | 2017-05-24 | 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 |
| 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 |
|---|---|---|---|---|
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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 |
| DE1620711A1 (de) * | 1962-05-25 | 1970-06-04 | Wander Ag Dr A | Verfahren zur Herstellung 11-basisch substituierter 5H-Dibenzo[b,e][1,4]diazepine |
| CH476743A (de) | 1962-06-08 | 1969-08-15 | Wander Ag Dr A | Verfahren zur Herstellung von Amidinen der Dibenzo (b,e) (1,4)-diazepin-Reihe |
| 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. |
| BE632120A (enExample) | 1963-05-09 | |||
| US3908010A (en) * | 1967-03-22 | 1975-09-23 | Wander Ag Dr A | Basically substituted heterocycles as anti-emetics |
| 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 |
| 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 (enExample) | 1966-12-16 | 1968-06-17 | ||
| US3852446A (en) * | 1967-03-13 | 1974-12-03 | Sandoz Ag | Organic compounds in treatment of psychotic disturbances |
| US3539573A (en) | 1967-03-22 | 1970-11-10 | Jean Schmutz | 11-basic substituted dibenzodiazepines and dibenzothiazepines |
| US3758479A (en) * | 1967-03-22 | 1973-09-11 | Sandoz Ag | Nitro and sulphamoyl substituted dibenzodiazepines |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| CH569730A5 (enExample) * | 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 |
| DE69516524T2 (de) | 1994-08-24 | 2001-01-18 | Astrazeneca Ab, Soedertaelje | 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 |
| AU5489299A (en) * | 1998-08-18 | 2000-03-14 | 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 |
| US6703371B1 (en) | 1999-07-28 | 2004-03-09 | Oswald Wiss | Preparations for reducing oxygen consumption during physical efforts |
| 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 |
| WO2002060870A2 (en) | 2000-11-17 | 2002-08-08 | Adolor Corporation | Delta agonist analgesics |
| IL139975A0 (en) | 2000-11-29 | 2002-02-10 | Univ Ramot | Anti proliferative drugs |
| DE60230869D1 (de) | 2001-05-18 | 2009-03-05 | Astrazeneca Ab | 4-(phenylpiperazinylmethyl) benzamidderivate und deren verwendung zur behandlung von schmerzen, angst oder gastrointestinalen störungen |
| EP1397366B1 (en) | 2001-06-01 | 2007-02-07 | AstraZeneca AB | Novel ligand for nicotinic acetylcholine receptors useful in therapy |
| SG152907A1 (en) * | 2001-07-09 | 2009-06-29 | Combinatorx Inc | Combinations for the treatment of inflammatory disorders |
| US7544681B2 (en) | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| KR20090130150A (ko) | 2001-09-27 | 2009-12-17 | 라모트 앳 텔 아비브 유니버시티 리미티드 | 접합된 항-정신병 약물 및 그의 용도 |
| ES2348282T3 (es) | 2002-04-18 | 2010-12-02 | Astrazeneca Ab | Compuestos de tienilo. |
| MXPA04010191A (es) | 2002-04-18 | 2005-02-03 | Astrazeneca Ab | Compuestos de furilo. |
| BR0309345A (pt) | 2002-04-18 | 2005-02-15 | Astrazeneca Ab | Composto ou sais farmaceuticamente aceitáveis do mesmo, composição farmacêutica, uso de um composto, e, métodos de tratamento ou profilaxia de doenças ou condições humanas, de distúrbios psicóticos ou de distúrbios de dano intelectual, e de jetlag, interrupção do hábito de fumar, dependência de nicotina, ânsias, dor e colite ulcerativa |
| SE0202465D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| SE0202430D0 (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 |
| BR0317528A (pt) | 2002-12-20 | 2005-11-22 | Basf Ag | Uso dos compostos, métodos para o controle de insetos, aracnìdeos ou nematodos, e para a proteção de plantas em crescimento contra o ataque ou a infestação por insetos, aracnìdeos ou nematodos, compostos, e, composições |
| EP1589974A2 (en) * | 2003-01-23 | 2005-11-02 | Acadia Pharmaceuticals Inc. | Use of n-desmethylclozapine to treat human neuropsychiatric disease |
| WO2004076431A1 (en) | 2003-02-22 | 2004-09-10 | Teva Pharmaceutical Industries Ltd. | 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 |
| CA2527170A1 (en) | 2003-04-15 | 2004-10-28 | Astrazeneca Ab | Therapeutic compounds |
| 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 |
| PL1696931T3 (pl) | 2003-12-22 | 2009-10-30 | Acadia Pharm Inc | Aminopodstawione analogi diarylo[A,D]cykloheptenowe jako agoniści receptorów muskarynowych i sposoby leczenia chorób neuropsychiatrycznych |
| US20060063754A1 (en) * | 2004-09-21 | 2006-03-23 | Edgar Dale M | Methods of treating a sleep disorder |
| BRPI0517423A (pt) | 2004-12-27 | 2008-10-07 | Astrazeneca Ab | composto, composição farmacêutica, método para o tratamento ou prevenção de distúrbios neurológicos e psiquiátricos associados com disfunção do glutamato em um animal, e, uso em um composto |
| 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 |
| US20070105836A1 (en) * | 2005-10-31 | 2007-05-10 | Lars Pettersson | 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 |
| 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 |
| PL2307389T3 (pl) * | 2008-06-20 | 2013-05-31 | Astrazeneca Ab | Pochodne dibenzotiazepiny i ich zastosowanie |
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