CN101962369A - 氨基取代的二芳基[a,d]环庚烯类似物作为毒蕈碱激动剂的用途及神经精神疾病的治疗方法 - Google Patents
氨基取代的二芳基[a,d]环庚烯类似物作为毒蕈碱激动剂的用途及神经精神疾病的治疗方法 Download PDFInfo
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- CN101962369A CN101962369A CN2010102389158A CN201010238915A CN101962369A CN 101962369 A CN101962369 A CN 101962369A CN 2010102389158 A CN2010102389158 A CN 2010102389158A CN 201010238915 A CN201010238915 A CN 201010238915A CN 101962369 A CN101962369 A CN 101962369A
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- compound
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- dibenzo
- replaces
- alkyl
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- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- WPGLRFGDZJSQGI-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(N)C1 WPGLRFGDZJSQGI-UHFFFAOYSA-N 0.000 description 1
- MXMNIQCGKFKLPN-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylamino)carbamate Chemical compound CC(C)(C)OC(=O)NNC1CCNCC1 MXMNIQCGKFKLPN-UHFFFAOYSA-N 0.000 description 1
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- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229960004098 thioridazine hydrochloride Drugs 0.000 description 1
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Classifications
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- 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
- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- 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
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
-
- 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
Landscapes
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- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
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| US53192703P | 2003-12-22 | 2003-12-22 | |
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| US54809004P | 2004-02-24 | 2004-02-24 | |
| US60/548,090 | 2004-02-24 | ||
| US54860404P | 2004-02-27 | 2004-02-27 | |
| US60/548,604 | 2004-02-27 |
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| CN2004800413564A Division CN1913900B (zh) | 2003-12-22 | 2004-12-21 | 作为毒蕈碱激动剂的氨基取代的二芳基[a,d]环庚烯类似物及神经精神疾病的治疗方法 |
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| EP (2) | EP2088147A1 (https=) |
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| BR (1) | BRPI0417749A (https=) |
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| PL (1) | PL1696931T3 (https=) |
| PT (1) | PT1696931E (https=) |
| SG (1) | SG133606A1 (https=) |
| SI (1) | SI1696931T1 (https=) |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104016937A (zh) * | 2014-05-09 | 2014-09-03 | 中科院广州化学有限公司 | 一种n-芳基氧氮杂卓酮类化合物及其制备方法 |
| CN107903244A (zh) * | 2017-11-29 | 2018-04-13 | 河南龙湖生物技术有限公司 | 具有抗肿瘤活性的2‑胺基取代苯并二氮卓化合物及其制备方法 |
| CN110627735A (zh) * | 2018-06-25 | 2019-12-31 | 江阴安博生物医药有限公司 | 一种新的喹硫平类似物及其制备方法和应用 |
| CN111909173A (zh) * | 2015-07-02 | 2020-11-10 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN112358455A (zh) * | 2020-11-16 | 2021-02-12 | 吉林奥来德光电材料股份有限公司 | 一种二苯并七元杂环类化合物及其制备方法与应用 |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2278729T3 (es) | 2000-03-06 | 2007-08-16 | Acadia Pharmaceuticals Inc. | Compuestos azaciclicos para usar en el tratamiento de enfermedades relacionadas con la serotonina. |
| MXPA04006280A (es) | 2001-12-28 | 2004-09-27 | Acadia Pharm Inc | Compuestos espiroazaciclicos como moduladores de receptor de monoamina. |
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| US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| CN1741803A (zh) * | 2003-01-23 | 2006-03-01 | 阿卡蒂亚药品公司 | N-脱甲基氯氮平在治疗人神经精神疾病中的用途 |
| US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| NZ527142A (en) | 2003-07-23 | 2006-03-31 | Douglas Pharmaceuticals Ltd | A stable suspension formulation |
| SG133606A1 (en) | 2003-12-22 | 2007-07-30 | Acadia Pharm Inc | Amino substituted diaryl [a,d] cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| WO2008021463A2 (en) * | 2006-08-15 | 2008-02-21 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl[a,d]cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US20090239840A1 (en) * | 2003-12-22 | 2009-09-24 | Acadia Pharmaceuticals, Inc. | AMINO SUBSTITUTED DIARYL[a,d]CYCLOHEPTENE ANALOGS AS MUSCARINIC AGONISTS AND METHODS OF TREATMENT OF NEUROPSYCHIATRIC DISORDERS |
| US20050171088A1 (en) * | 2004-01-30 | 2005-08-04 | Astrazeneca Ab | Treatment of psychoses with dibenzothiazepine antipsychotic |
| JP2007536216A (ja) * | 2004-04-01 | 2007-12-13 | 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 | 固体n−デスメチルクロザピンおよびその結晶形を合成および単離する方法 |
| US20050261278A1 (en) * | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US7820695B2 (en) | 2004-05-21 | 2010-10-26 | Acadia Pharmaceuticals, Inc. | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US7786141B2 (en) | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| TW200621244A (en) | 2004-08-19 | 2006-07-01 | Vertex Pharma | Modulators of muscarinic receptors |
| US20060081361A1 (en) * | 2004-09-13 | 2006-04-20 | Gabbey Lawrence W | Oil cooler with integral filter |
| CA2580129A1 (en) * | 2004-09-27 | 2006-04-06 | Acadia Pharmaceuticals Inc. | Salts of n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and their preparation |
| US7790899B2 (en) | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
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| 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 |
| WO2006107948A2 (en) * | 2005-04-04 | 2006-10-12 | Acadia Pharmaceuticals Inc. | Use of n-desmethylclozapine and related compounds as dopamine stabilizing agents |
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| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| US20080090805A1 (en) * | 2005-10-17 | 2008-04-17 | Acadia Pharmaceuticals Inc. | Cb-1 modulating compounds and their use |
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| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| WO2007053618A1 (en) * | 2005-10-31 | 2007-05-10 | Acadia Pharmaceuticals Inc. | Prodrugs of muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20070105835A1 (en) * | 2005-11-07 | 2007-05-10 | Kazantsev Aleksey G | Compositions and methods for modulating poly(ADP-ribose) polymerase activity |
| WO2007062339A2 (en) * | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Liquid formulations |
| WO2007062336A2 (en) * | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Salt forms |
| CN101426499A (zh) | 2006-02-22 | 2009-05-06 | 弗特克斯药品有限公司 | 毒蕈碱受体调节剂 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| WO2007134077A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007133802A2 (en) * | 2006-05-15 | 2007-11-22 | Acadia Pharmaceuticals Inc. | Pharmaceutical formulations of pimavanserin |
| DE102006032427A1 (de) * | 2006-07-13 | 2008-01-17 | Neuraxpharm Arzneimittel Gmbh U. Co. Kg | Verwendung von Zusammensetzungen von Clozapin, Quetiapin, schwer oder sehr schwer löslichen Säureadditionssalzen von Quetiapin und/oder Olanzapin zur Herstellung von Lösungen zur oralen Verabreichung |
| DE102006032426A1 (de) * | 2006-07-13 | 2008-01-17 | Neuraxpharm Arzneimittel Gmbh U. Co. Kg | Verwendung von Zusammensetzungen von Clozapin, Quetiapin, schwer oder sehr schwer löslichen Säureadditionssalzen von Quetiapin und/oder Olanzapin zur Herstellung von Lösungen zur oralen Verabreichung |
| WO2008021545A2 (en) * | 2006-08-18 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| EP2068872A1 (en) | 2006-09-08 | 2009-06-17 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| WO2008118141A2 (en) * | 2006-10-17 | 2008-10-02 | Acadia Pharmaceuticals Inc. | Use of cannabinoid modulating compounds in combination with other therapeutic compounds for adjunctive therapy |
| EP2120957A4 (en) * | 2006-12-20 | 2011-05-04 | Astrazeneca Ab | COMPOUNDS AND USES THEREOF |
| US20100016284A1 (en) * | 2006-12-20 | 2010-01-21 | Astrazeneca Ab | Compounds and uses thereof - 151 |
| GB0701970D0 (en) * | 2007-02-01 | 2007-03-14 | Wilson Stuart | Treatment of protein aggregation diseases |
| US8093237B2 (en) * | 2007-03-15 | 2012-01-10 | Aryx Therapeutics, Inc. | Dibenzo[b,f][1,4]oxazapine compounds |
| CA2681506C (en) | 2007-03-19 | 2016-05-24 | Perry Peters | Combinations of 5-ht2a inverse agonists and antagonists with antipsychotics |
| MX2010003373A (es) * | 2007-10-03 | 2010-04-30 | Vertex Pharma | Moduladores de receptores muscarinicos. |
| WO2009149347A1 (en) | 2008-06-05 | 2009-12-10 | President And Fellows Of Harvard College | High-valent palladium fluoride complexes and uses thereof |
| MX2010014203A (es) * | 2008-06-20 | 2011-02-22 | Astrazeneca Ab | Derivados de dibenzotiazepina y sus usos - 424. |
| WO2010062565A1 (en) * | 2008-10-27 | 2010-06-03 | Acadia Pharmaceuticals Inc. | Muscarinic agonists |
| AU2009316478A1 (en) | 2008-11-20 | 2010-05-27 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| EP2385944A4 (en) * | 2009-01-09 | 2013-06-19 | Harvard College | FLUORINARY COMPOUNDS AND METHOD OF USE THEREOF |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| CN101531570B (zh) * | 2009-04-17 | 2012-10-10 | 中国科学院上海有机化学研究所 | 1,2-取代-5-乙炔基-(或10,11-二氢)-5H-二苯基[a,d]环庚烯(烷)-5-醇、合成方法及用途 |
| US10265311B2 (en) | 2009-07-22 | 2019-04-23 | PureTech Health LLC | Methods and compositions for treatment of disorders ameliorated by muscarinic receptor activation |
| PT3061821T (pt) | 2009-07-22 | 2019-09-05 | PureTech Health LLC | Composições para tratamento de distúrbios melhorados por ativação de recetores muscarínicos |
| WO2011025748A1 (en) * | 2009-08-26 | 2011-03-03 | Acadia Pharmaceuticals, Inc. | Amino substituted diaryl [a, d] cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| WO2012142162A2 (en) | 2011-04-12 | 2012-10-18 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| US9273083B2 (en) | 2012-09-26 | 2016-03-01 | President And Fellows Of Harvard College | Nickel fluorinating complexes and uses thereof |
| CA2923835C (en) * | 2013-09-11 | 2022-11-29 | The Administrators Of The Tulane Educational Fund | Novel anthranilic amides and the use thereof |
| WO2015058047A2 (en) | 2013-10-18 | 2015-04-23 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| ES2890492T3 (es) | 2015-07-20 | 2022-01-20 | Acadia Pharm Inc | Métodos para preparar N-(4-fluorobencil)-N-(1-metilpiperidin-4-il)-N'-(4-(2-metilpropiloxi)fenilmetil)carbamida y su sal de tartrato y forma polimórfica C |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| WO2018139471A1 (ja) * | 2017-01-25 | 2018-08-02 | 大日本住友製薬株式会社 | ジベンゾジアゼピン誘導体 |
| WO2018148529A1 (en) | 2017-02-10 | 2018-08-16 | Florida A&M University | Identification of agents displaying functional activation of dopamine d2 and d4 receptors |
| EP3615028A1 (en) | 2017-04-28 | 2020-03-04 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| EP3675827A1 (en) | 2017-08-30 | 2020-07-08 | Acadia Pharmaceuticals Inc. | Formulations of pimavanserin |
| AU2018346358A1 (en) | 2017-10-06 | 2020-04-09 | Leyden Technologies B.V. | Stable solutions of multicyclic antidepressants |
| EP3746126B1 (en) | 2018-01-30 | 2024-07-31 | Apnimed, Inc. (Delaware) | Methods and compositions for treating sleep apnea or simple snoring |
| JP2021104931A (ja) * | 2018-02-22 | 2021-07-26 | 大日本住友製薬株式会社 | 含窒素複素環を有するジベンゾアゼピン誘導体 |
| KR102408292B1 (ko) | 2018-09-28 | 2022-06-10 | 카루나 세러퓨틱스 인코포레이티드 | 무스카린성 수용체 활성화에 의해 개선된 장애의 치료를 위한 조성물 및 방법 |
| JP7696354B2 (ja) | 2019-10-21 | 2025-06-20 | アライリオン インコーポレイテッド | 睡眠障害の治療のためのH1および5-HT2A受容体調節物質としての3-(4-(11H-ジベンゾ[b,e][1,4]アゼピン-6-イル)ピペラジン-1-イル)-プロパン酸誘導体および3-(4-(ジベンゾ[b,f][1,4]オキサゼピン/チアゼピン/ジアゼピン-11-イル)ピペラジン-1-イル)-プロパン酸誘導体 |
| TWI820605B (zh) * | 2022-02-18 | 2023-11-01 | 國立臺灣大學 | 抗菌化合物、其製備方法及其用途 |
Family Cites Families (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR870763A (fr) | 1939-12-19 | 1942-03-24 | Zeiss Ikon Ag | Procédé destiné à faire disparaître les bruits produits par les boucles du film dans les appareils de prise de vues et de reproduction, en particulier pour la priseet la reproduction de films sonores |
| CH240228A (de) | 1944-07-28 | 1945-12-15 | Ciba Geigy | Schaumisoliermasse auf Kunstharzbasis. |
| FR939591A (fr) | 1946-01-09 | 1948-11-18 | Philips Nv | Récepteur de télévision |
| FR939595A (fr) | 1947-01-08 | 1948-11-18 | Perfectionnements apportés aux tuiles à recouvrement en matériaux de toute nature | |
| FR51M (https=) | 1960-06-03 | 1960-11-28 | ||
| CH422793A (de) * | 1961-07-20 | 1966-10-31 | Wander Ag Dr A | Verfahren zur Herstellung 11-basisch substituierter Dibenzo(b,f) (1,4)thiazepine |
| FR1334944A (fr) | 1961-08-11 | 1963-08-16 | Wander Ag Dr A | Procédé de préparation d'amidines de la série des 5-dibenzo-[b,e] [1,4]-diazépines |
| 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. |
| US3389139A (en) * | 1963-06-14 | 1968-06-18 | Wander Ag Dr A | 6-homopiperazino and piperazinomorphanthridines |
| GB1006156A (en) | 1963-06-14 | 1965-09-29 | Wander Ag Dr A | 6-basic substituted morphanthridines |
| 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 |
| US3908010A (en) * | 1967-03-22 | 1975-09-23 | Wander Ag Dr A | Basically substituted heterocycles as anti-emetics |
| AT252925B (de) | 1964-05-27 | 1967-03-10 | Wander Ag Dr A | Verfahren zur Herstellung neuer 11-basisch substituierter Dibenz[b,f][1,4]oxazepine |
| 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 |
| GB1184251A (en) * | 1966-04-15 | 1970-03-11 | American Cyanamid Co | Oxazepines and Thiazepines |
| GB1192812A (en) * | 1966-05-20 | 1970-05-20 | American Cyanamid Co | 2-Chloro-11-(1-Piperazinyl)Dibenz[b,f]-[1,4]Oxazepine, Non-Toxic Acid Addition Salts thereof, and Therapeutic Compositions containing said Oxazepine or Salts |
| NL6715650A (https=) | 1966-12-16 | 1968-06-17 | ||
| GB1177956A (en) | 1966-12-23 | 1970-01-14 | American Cyanamid Co | Production of Oxazepines and Thiazepines |
| CA979441A (en) | 1967-02-27 | 1975-12-09 | American Cyanamid Company | 11-(piperazinyl) dibenz (b,f) (1,4) oxazepines and analogous thiazepines |
| DE1720007A1 (de) | 1967-03-13 | 1971-05-19 | Wander Ag Dr A | Basisch substituierte Heterocyclen |
| CH514612A (de) | 1967-03-13 | 1971-10-31 | Wander Ag Dr A | Verfahren zur Herstellung 11-basisch substituierter Dibenz(b,f)-1,4-oxazepine und Dibenzo(b,e)-1,4-diazepine |
| 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 |
| US3751415A (en) * | 1967-03-22 | 1973-08-07 | Sandoz Ag | 2-nitro-11-(1-piperazinyl)-dibenz(b,f)(1,4)oxazepines |
| CA918659A (en) * | 1969-07-31 | 1973-01-09 | Yoshitomi Pharmaceutical Industries | 11-(4-substituted-1-piperazinyl)-dibenzo (b,f) (1,4) thiazepines |
| NL7110453A (https=) | 1970-08-06 | 1972-02-08 | Wander Ag Dr A | |
| US3660406A (en) * | 1970-10-26 | 1972-05-02 | American Cyanamid Co | 2-chloro-7-hydroxy-11-(1-piperazinyl)dibenz(b f)(1 4)oxazepines |
| CH555856A (de) * | 1971-05-04 | 1974-11-15 | Hoffmann La Roche | Verfahren zur herstellung von tricyclischen verbindungen. |
| US3962248A (en) * | 1972-04-04 | 1976-06-08 | Sandoz, Inc. | Process for making 11-piperazino-diazepines, oxazepines, thiazepines and azepines |
| CH569730A5 (https=) | 1972-04-04 | 1975-11-28 | Wander Ag Dr A | |
| CH585222A5 (en) | 1973-02-14 | 1977-02-28 | Wander Ag Dr A | Prepn. of antipsychotic heterocyclic piperazine derivs. - by reaction of heterocyclic ketones with metal piperazine complexes |
| NL7403657A (https=) | 1973-03-23 | 1974-09-25 | ||
| US3983234A (en) * | 1974-07-04 | 1976-09-28 | Sandoz Ltd. | Treatment of dyskinesias |
| DE2625258A1 (de) | 1975-06-06 | 1976-12-09 | Hoffmann La Roche | Dibenzo eckige klammer auf b,f eckige klammer zu thiepinderivat |
| FI762646A7 (https=) | 1975-09-24 | 1977-03-25 | Sandoz Ag | |
| US4045445A (en) * | 1975-12-14 | 1977-08-30 | American Cyanamid Company | 11-(4-Piperidyl)dibenzo-diazepines |
| CS179793B1 (en) | 1976-02-13 | 1977-11-30 | Miroslav Protiva | Biological derivative of 11-/4-methylpiperazino/-5h-dib)nzo/b,e/-1,4-diazepine |
| CH601288A5 (en) | 1976-06-09 | 1978-07-14 | Sandoz Ag | 11-Piperazino-5H-di:benzodiazepine derivs. |
| US4406900A (en) * | 1976-11-10 | 1983-09-27 | Sandoz Ltd. | Neuroleptic use of morphanthridines |
| CH624682A5 (https=) * | 1976-11-10 | 1981-08-14 | Sandoz Ag | |
| US4191760A (en) * | 1977-02-23 | 1980-03-04 | Abbott Laboratories | Dibenzodiazepines |
| US4097597A (en) * | 1977-02-23 | 1978-06-27 | Abbott Laboratories | Dibenzo b,e! 1,4!diazepines |
| US4096261A (en) * | 1977-02-23 | 1978-06-20 | Abbott Laboratories | Dibenzodiazepines |
| DD133235A1 (de) | 1977-10-10 | 1978-12-20 | Carla Rueger | Verfahren zur herstellung von in 11-stellung basisch substituierten 5h-dibenzo eckige klammer auf b,e eckige klammer zu eckige klammer auf 1,4 eckige klammer zu diazepinen |
| CS196893B1 (en) * | 1977-12-22 | 1980-04-30 | Miroslav Protiva | 3-fluor-10-piperazino-8-substituted 10,11-dihydro-dibenzothiepines |
| US4263207A (en) * | 1978-08-01 | 1981-04-21 | Merck & Co., Inc. | 10,11-Dihydrodibenzo[b,f][1,4]thiazepine carboxylic acids esters and amides thereof |
| US4404137A (en) * | 1979-10-16 | 1983-09-13 | Lilly Industries Limited | Pyrazolo [3,4-b][1,5]benzodiazepine compounds |
| US4764616A (en) | 1983-05-18 | 1988-08-16 | Hoechst-Roussel Pharmaceuticals Inc. | Benzopyrrolobenzodiazepines and quinobenzodiazepines |
| US4663453A (en) * | 1983-05-18 | 1987-05-05 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepines having dopamine receptor activity |
| GB8607684D0 (en) * | 1986-03-27 | 1986-04-30 | Ici America Inc | Thiazepine compounds |
| JPH04211071A (ja) * | 1990-03-05 | 1992-08-03 | Hokuriku Seiyaku Co Ltd | 多環式化合物 |
| BE1004596A4 (fr) | 1990-09-26 | 1992-12-22 | Therabel Res S A N V | Derives de methylpiperazinoazepine, leur preparation et leur utilisation. |
| US5817655A (en) * | 1991-04-23 | 1998-10-06 | Eli Lilly And Company | Methods of treatment using a thieno-benzodiazepine |
| US5300422A (en) * | 1991-12-04 | 1994-04-05 | Case Western Reserve University | Screening method for controlling agranulocytosis |
| US5393752A (en) * | 1992-05-26 | 1995-02-28 | Therabel Research S.A./N.V. | Methylpiperazinoazepine compounds, preparation and use thereof |
| WO1994026107A1 (en) * | 1993-05-13 | 1994-11-24 | New York University | Psychosis protecting nucleic acid, peptides, compositions and method of use |
| US5354747A (en) * | 1993-06-16 | 1994-10-11 | G. D. Searle & Co. | 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9- and/or 10-substituted dibenzoxazepine and dibenzthiazepine compounds, pharmaceutical compositions and methods of use |
| IL110298A (en) * | 1993-07-13 | 1999-04-11 | Brann Mark Robert | Identification of ligands by selective amplification of cells transfected with receptors |
| US5538965A (en) * | 1993-12-23 | 1996-07-23 | Allelix Biopharmaceuticals Inc. | Dopamine receptor ligands |
| US6566065B1 (en) * | 1994-05-26 | 2003-05-20 | Mcgill University | Method of diagnosing schizophrenia by detecting a mutation in the (MTHFR) gene |
| GB2292685A (en) | 1994-07-27 | 1996-03-06 | Sankyo Co | Allosteric effectors at muscarinic receptors |
| US5602120A (en) | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | Benzyl-substituted compounds having dopamine receptor affinity |
| US5602121A (en) | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | Alkyl-substituted compounds having dopamine receptor affinity |
| US5602124A (en) * | 1994-12-12 | 1997-02-11 | Allelix Biopharmaceuticals, Inc. | 5-HT2 receptor ligands |
| US5700445A (en) * | 1994-12-12 | 1997-12-23 | Allelix Biopharmaceuticals, Inc. | N-methyl piperazine compounds having dopamine receptor affinity |
| SE9500998D0 (sv) * | 1995-03-19 | 1995-03-19 | Haakan Wilhelm Wikstroem | New sulfone ester analogues of iso-clozapine and related structures: atypical neuroleptics |
| GB9617305D0 (en) * | 1996-08-17 | 1996-09-25 | Glaxo Wellcome Spa | Heterocyclic compounds |
| NZ525108A (en) | 1998-03-31 | 2005-02-25 | Acadia Pharm Inc | Compounds with activity on muscarinic receptors |
| GB9924962D0 (en) | 1999-10-21 | 1999-12-22 | Mrc Collaborative Centre | Allosteric sites on muscarinic receptors |
| CN1249051C (zh) * | 2000-04-28 | 2006-04-05 | 阿卡蒂亚药品公司 | 毒蕈碱性激动剂 |
| AU2002249885A1 (en) | 2000-11-17 | 2002-08-12 | Adolor Corporation | Delta agonist analgesics |
| US6890919B2 (en) | 2001-06-26 | 2005-05-10 | Shitij Kapur | Atypical antipsychotic agents having low affinity for the D2 receptor |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| DE10206941A1 (de) | 2002-02-19 | 2003-09-25 | Goetz Nowak | Neue Arzneimittel |
| AU2003217936A1 (en) | 2002-03-28 | 2003-10-13 | Eli Lilly And Company | Piperazine substituted aryl benzodiazepines and their use as dopamine receptor antagonists for the treatment of psychotic disorders |
| CN1681388A (zh) | 2002-09-18 | 2005-10-12 | Fmc有限公司 | 三环衍生物杀虫剂 |
| AU2003290079A1 (en) | 2002-12-20 | 2004-07-14 | Basf Aktiengesellschaft | Pesticidal dibenzo(hetero)azepine derivatives |
| DK2009000T3 (da) | 2003-01-16 | 2011-09-05 | Acadia Pharm Inc | Selektive serotonin 2A/2C-receptor invers-agonister som terapeutika for neurodegenerative sygdomme |
| CN1741803A (zh) * | 2003-01-23 | 2006-03-01 | 阿卡蒂亚药品公司 | N-脱甲基氯氮平在治疗人神经精神疾病中的用途 |
| US20050250767A1 (en) * | 2003-01-23 | 2005-11-10 | Weiner David M | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20050085463A1 (en) * | 2003-01-23 | 2005-04-21 | Weiner David M. | Use of N-desmethylclozapine to treat human neuropsychiatric disease |
| US20070275957A1 (en) * | 2003-01-23 | 2007-11-29 | Weiner David M | Use of n-desmethylclozapine to treat human neuropsychiatric disease |
| EP1596867A4 (en) | 2003-02-19 | 2006-03-22 | Merck & Co Inc | TREATMENT OF PSYCHOSIS WITH A MUSCARIN M1 RECEPTOR ECTOPIC ACTIVATOR |
| DE10310196A1 (de) | 2003-03-06 | 2004-09-23 | Rina-Netzwerk Rna Technologien Gmbh | Verwendung eines trizyklischen Antidepressivums zur Förderung der Endozytose |
| ES2349091T3 (es) | 2003-07-02 | 2010-12-27 | Astrazeneca Ab | Metabolito de quetiapina. |
| SG133606A1 (en) * | 2003-12-22 | 2007-07-30 | Acadia Pharm Inc | Amino substituted diaryl [a,d] cycloheptene analogs as muscarinic agonists and methods of treatment of neuropsychiatric disorders |
| JP4847320B2 (ja) | 2004-02-20 | 2011-12-28 | 大日本住友製薬株式会社 | 統合失調症の記憶・学習機能障害治療薬のinvivoスクリーニング方法 |
| JP2007536216A (ja) * | 2004-04-01 | 2007-12-13 | 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 | 固体n−デスメチルクロザピンおよびその結晶形を合成および単離する方法 |
| EP1778244A1 (en) | 2004-08-05 | 2007-05-02 | Acadia Pharmaceuticals Inc. | Use of n-desmethylclozapine to treat human neuropsychiatric disease |
| US20060063754A1 (en) * | 2004-09-21 | 2006-03-23 | Edgar Dale M | Methods of treating a sleep disorder |
| EP1804804B1 (en) | 2004-09-21 | 2012-01-25 | Hypnion, Inc. | 3-[4-(DIBENZO[b,f][1,4]OXAZEPIN-11-YL)-PIPERAZIN-1-YL]-2,2-DIMETHYL PROPANOIC ACID FOR USE IN THE TREATMENT OF SLEEP DISORDERS |
| US7563785B2 (en) | 2004-10-29 | 2009-07-21 | Hypnion, Inc. | Quetiapine analogs and methods of use thereof |
| WO2006081327A2 (en) | 2005-01-25 | 2006-08-03 | University Of Vermont And State Agricultural College | Small molecules that reduce fungal growth |
| MX2007009797A (es) | 2005-02-14 | 2007-11-06 | Combinatorx Inc | Compuestos y sus usos. |
| WO2006107948A2 (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 |
| US20090215744A1 (en) | 2005-11-18 | 2009-08-27 | Astrazeneca Ab | Solid Formulations |
| WO2007062339A2 (en) | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Liquid formulations |
| WO2007062336A2 (en) | 2005-11-18 | 2007-05-31 | Astrazeneca Ab | Salt forms |
| EP1951257A4 (en) | 2005-11-18 | 2008-11-05 | Astrazeneca Ab | CRYSTALLINE FORMS |
| WO2008002602A1 (en) | 2006-06-27 | 2008-01-03 | Acadia Pharmaceuticals Inc. | Use of n-desmethylclozapine to treat psychosis |
| WO2008066620A2 (en) | 2006-10-20 | 2008-06-05 | Concert Pharmaceuticals Inc. | Dibenzothiazepine derivatives |
-
2004
- 2004-12-21 SG SG200704645-1A patent/SG133606A1/en unknown
- 2004-12-21 CA CA002550735A patent/CA2550735A1/en not_active Abandoned
- 2004-12-21 AU AU2004308955A patent/AU2004308955B2/en not_active Ceased
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- 2004-12-21 PT PT04815318T patent/PT1696931E/pt unknown
- 2004-12-21 JP JP2006547344A patent/JP2007534656A/ja not_active Withdrawn
- 2004-12-21 US US11/019,555 patent/US7550454B2/en not_active Expired - Fee Related
- 2004-12-21 PL PL04815318T patent/PL1696931T3/pl unknown
- 2004-12-21 CN CN2010102389158A patent/CN101962369A/zh active Pending
- 2004-12-21 ES ES04815318T patent/ES2324713T3/es not_active Expired - Lifetime
-
2006
- 2006-05-03 US US11/417,859 patent/US7517871B2/en not_active Expired - Fee Related
- 2006-05-03 US US11/417,441 patent/US7491715B2/en not_active Expired - Fee Related
- 2006-06-20 IL IL176447A patent/IL176447A0/en unknown
- 2006-07-20 NO NO20063371A patent/NO20063371L/no not_active Application Discontinuation
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- 2007-04-10 US US11/733,476 patent/US7622461B2/en not_active Expired - Fee Related
-
2009
- 2009-06-25 CY CY20091100666T patent/CY1109171T1/el unknown
- 2009-11-18 US US12/621,435 patent/US20100129473A1/en not_active Abandoned
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| CN111909173A (zh) * | 2015-07-02 | 2020-11-10 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN112062778A (zh) * | 2015-07-02 | 2020-12-11 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN112062778B (zh) * | 2015-07-02 | 2024-04-19 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂䓬噁唑烷酮化合物及其使用方法 |
| CN107903244A (zh) * | 2017-11-29 | 2018-04-13 | 河南龙湖生物技术有限公司 | 具有抗肿瘤活性的2‑胺基取代苯并二氮卓化合物及其制备方法 |
| CN107903244B (zh) * | 2017-11-29 | 2019-06-14 | 武汉珈创生物技术股份有限公司 | 具有抗肿瘤活性的2-胺基取代苯并二氮卓化合物及其制备方法 |
| CN110627735A (zh) * | 2018-06-25 | 2019-12-31 | 江阴安博生物医药有限公司 | 一种新的喹硫平类似物及其制备方法和应用 |
| CN112358455A (zh) * | 2020-11-16 | 2021-02-12 | 吉林奥来德光电材料股份有限公司 | 一种二苯并七元杂环类化合物及其制备方法与应用 |
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