OA12924A - New spirocondensed quinazolinones and their use asphosphodiesterase inhibitors. - Google Patents
New spirocondensed quinazolinones and their use asphosphodiesterase inhibitors. Download PDFInfo
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- OA12924A OA12924A OA1200500073A OA1200500073A OA12924A OA 12924 A OA12924 A OA 12924A OA 1200500073 A OA1200500073 A OA 1200500073A OA 1200500073 A OA1200500073 A OA 1200500073A OA 12924 A OA12924 A OA 12924A
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- OA
- OAPI
- Prior art keywords
- alkyl
- nr7r8
- compound
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- nr4r5
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- 239000003112 inhibitor Substances 0.000 title description 6
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
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- 125000000217 alkyl group Chemical group 0.000 claims description 73
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 13
- 229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 claims description 12
- -1 SO2CH3 Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000002606 phosphodiesterase VII inhibitor Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
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- IMZMUNGROJZNFZ-UHFFFAOYSA-N n-[2-[2-(8-chloro-2-oxospiro[1,3-dihydroquinazoline-4,1'-cyclohexane]-5-yl)oxyethylamino]ethyl]acetamide Chemical compound C1=2C(OCCNCCNC(=O)C)=CC=C(Cl)C=2NC(=O)NC21CCCCC2 IMZMUNGROJZNFZ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20020292275 EP1400244A1 (en) | 2002-09-17 | 2002-09-17 | New spirocondensed quinazolinones and their use as phosphodiesterase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA12924A true OA12924A (en) | 2006-10-13 |
Family
ID=31896987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200500073A OA12924A (en) | 2002-09-17 | 2003-09-08 | New spirocondensed quinazolinones and their use asphosphodiesterase inhibitors. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US7429598B2 (pt) |
| EP (2) | EP1400244A1 (pt) |
| JP (1) | JP2006501277A (pt) |
| KR (1) | KR20050057371A (pt) |
| CN (1) | CN1681507A (pt) |
| AP (1) | AP2005003251A0 (pt) |
| AR (1) | AR041271A1 (pt) |
| AU (1) | AU2003259496A1 (pt) |
| BR (1) | BR0314379A (pt) |
| CA (1) | CA2499330C (pt) |
| CO (1) | CO5540391A2 (pt) |
| CR (1) | CR7728A (pt) |
| EA (1) | EA200500312A1 (pt) |
| EC (1) | ECSP055671A (pt) |
| GT (1) | GT200300201A (pt) |
| HN (1) | HN2003000285A (pt) |
| HR (1) | HRP20050223A2 (pt) |
| IS (1) | IS7700A (pt) |
| MA (1) | MA27439A1 (pt) |
| MX (1) | MXPA05002913A (pt) |
| NO (1) | NO20051695L (pt) |
| OA (1) | OA12924A (pt) |
| PA (1) | PA8582801A1 (pt) |
| PE (1) | PE20050073A1 (pt) |
| PL (1) | PL375977A1 (pt) |
| TN (1) | TNSN05073A1 (pt) |
| TW (1) | TWI251590B (pt) |
| UY (1) | UY27986A1 (pt) |
| WO (1) | WO2004026818A1 (pt) |
| ZA (1) | ZA200501381B (pt) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003106381A2 (en) | 2002-06-12 | 2003-12-24 | Exelixis, Inc. | Human adam-10 inhibitors |
| AU2006219643A1 (en) * | 2005-03-01 | 2006-09-08 | Pfizer Limited | Use of PDE7 inhibitors for the treatment of neuropathic pain |
| WO2006092692A1 (en) * | 2005-03-01 | 2006-09-08 | Pfizer Limited | Use of combinations of pde7 inhibitors and alpha-2-delty ligands for the treatment of neuropathic pain |
| GB0504209D0 (en) * | 2005-03-01 | 2005-04-06 | Pfizer Ltd | New use of PDE7 inhibitors |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| US7678363B2 (en) | 2005-08-26 | 2010-03-16 | Braincells Inc | Methods of treating psychiatric conditions comprising administration of muscarinic agents in combination with SSRIs |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| RS20080233A (en) | 2005-12-02 | 2009-07-15 | Pfizer Limited, | Spirocyclic quinazoline derivatives as pde7 inhibitors |
| ATE555091T1 (de) | 2006-02-03 | 2012-05-15 | Bionomics Ltd | Substituierte benzofurane, benzothiophene, benzoselenophene und indole und ihre verwendung als tubulinpolymerisationsinhibitoren |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| 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 |
| BRPI0809244A2 (pt) | 2007-03-27 | 2014-09-23 | Omeros Corp | Métodos de tratamento de uma anormalidade de movimento, e para identificação de um agente que inibe a atividade pde7. |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| WO2008142550A2 (en) * | 2007-05-24 | 2008-11-27 | Pfizer Limited | Spirocyclic derivatives |
| CA2694284A1 (en) * | 2007-06-29 | 2009-01-08 | Jennifer Cossrow | Heterocyclic compounds useful as raf kinase inhibitors |
| TWI444379B (zh) | 2007-06-29 | 2014-07-11 | Sunesis Pharmaceuticals Inc | 有用於作為Ｒａｆ激酶抑制劑之化合物 |
| NZ591166A (en) * | 2008-08-06 | 2012-11-30 | Biomarin Pharm Inc | Dihydropyridophthalazinone inhibitors of poly(adp-ribose)polymerase (parp) |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| AU2011212928B2 (en) | 2010-02-03 | 2016-06-23 | Medivation Technologies Llc | Dihydropyridophthalazinone inhibitors of poly(ADP-ribose) polymerase (PARP) for use in treatment of diseases associated with a PTEN deficiency |
| US20110190266A1 (en) * | 2010-02-04 | 2011-08-04 | Daniel Chu | 5,6,6a,7,8,9-HEXAHYDRO-2H-PYRIDOPHTHALAZINONE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE (PARP) |
| MX340319B (es) | 2010-02-08 | 2016-07-06 | Medivation Technologies Inc | Procesos para sintetizar derivados de dihidropiridoftalazinona. |
| BR112013009117A2 (pt) | 2010-10-21 | 2016-07-19 | Biomarin Pharm Inc | sal tosilato de (8s,9r)-5-fluor-8-(4-fluorefenil)-9-(1-metil-1h-1,2,4-triazol-5-il)-8,9-diidro-2h-pirido[4,3,2-de]ftalazin-3(7h)-ona, método para preparar uma forma cristalina e uso do mesmo,composição farmacêutica e método para tratar um câncer ou um sintoma do mesmo. |
| AU2011326173B2 (en) | 2010-11-08 | 2015-08-27 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| EP2804603A1 (en) | 2012-01-10 | 2014-11-26 | President and Fellows of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| WO2019014305A1 (en) | 2017-07-12 | 2019-01-17 | Dart Neuroscience, Llc | SUBSTITUTED BENZOXAZOLE AND BENZOFURAN COMPOUNDS AS PDE7 INHIBITORS |
| CN112574202B (zh) * | 2020-12-11 | 2021-11-09 | 台州学院 | 一种螺喹唑啉-2-酮类衍生物及其制备方法和应用 |
| WO2024038089A1 (en) | 2022-08-18 | 2024-02-22 | Mitodicure Gmbh | Use of a therapeutic agent with phosphodiesterase-7 inhibitory activity for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exertional intolerance |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5959685A (ja) * | 1982-09-28 | 1984-04-05 | Kyowa Hakko Kogyo Co Ltd | 新規なピペリジン誘導体 |
| JPS5959865A (ja) * | 1982-09-30 | 1984-04-05 | Ube Ind Ltd | 耐熱鋳鋼 |
| US4666913A (en) * | 1985-11-22 | 1987-05-19 | William H. Rorer, Inc. | Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses |
| US4906630A (en) * | 1985-11-22 | 1990-03-06 | Rorer Pharmaceutical Corporation | Method of increasing cardiac contractility using pharmaceutical compositions comprising benzodiazinone- pyridazinone or hydroxy-pyrazolyl compounds |
| US4764512A (en) * | 1986-08-27 | 1988-08-16 | Rorer Pharmaceutical Corporation | Benzodiazinone-pyridone compounds, cardiotonic compositions including the same, and their uses |
| US5102886A (en) | 1990-10-12 | 1992-04-07 | American Home Products Corporation | 1'-aminospiro[isoquinoline-4(1H),3'-pyrrolidine]-1,2',3,5'(2H)-tetrones and analogs thereof useful as aldose reductase inhibitors |
| IL102764A0 (en) * | 1991-08-16 | 1993-01-31 | Merck & Co Inc | Quinazoline derivatives,and pharmaceutical compositions containing them |
| WO2000066560A1 (en) | 1999-05-04 | 2000-11-09 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| AP1699A (en) * | 2001-03-21 | 2006-12-26 | Warner Lambert Co | New spirotricyclic derivatives and their use as phosphodiesterase-7 inhibitors |
| US6596167B2 (en) | 2001-03-26 | 2003-07-22 | Koch Membrane Systems, Inc. | Hydrophilic hollow fiber ultrafiltration membranes that include a hydrophobic polymer and a method of making these membranes |
-
2002
- 2002-09-17 EP EP20020292275 patent/EP1400244A1/en not_active Withdrawn
-
2003
- 2003-09-08 KR KR1020057004511A patent/KR20050057371A/ko not_active Application Discontinuation
- 2003-09-08 EP EP20030797455 patent/EP1542694A1/en not_active Withdrawn
- 2003-09-08 AU AU2003259496A patent/AU2003259496A1/en not_active Abandoned
- 2003-09-08 CA CA 2499330 patent/CA2499330C/en not_active Expired - Fee Related
- 2003-09-08 PL PL37597703A patent/PL375977A1/xx not_active Application Discontinuation
- 2003-09-08 MX MXPA05002913A patent/MXPA05002913A/es active IP Right Grant
- 2003-09-08 BR BR0314379A patent/BR0314379A/pt not_active IP Right Cessation
- 2003-09-08 EA EA200500312A patent/EA200500312A1/ru unknown
- 2003-09-08 AP AP2005003251A patent/AP2005003251A0/xx unknown
- 2003-09-08 OA OA1200500073A patent/OA12924A/en unknown
- 2003-09-08 CN CNA038221284A patent/CN1681507A/zh active Pending
- 2003-09-08 JP JP2004537412A patent/JP2006501277A/ja not_active Withdrawn
- 2003-09-08 WO PCT/IB2003/003965 patent/WO2004026818A1/en active Application Filing
- 2003-09-16 PA PA8582801A patent/PA8582801A1/es unknown
- 2003-09-16 TW TW92125477A patent/TWI251590B/zh not_active IP Right Cessation
- 2003-09-16 PE PE2003000943A patent/PE20050073A1/es not_active Application Discontinuation
- 2003-09-16 AR ARP030103355 patent/AR041271A1/es unknown
- 2003-09-17 UY UY27986A patent/UY27986A1/es not_active Application Discontinuation
- 2003-09-17 GT GT200300201A patent/GT200300201A/es unknown
- 2003-09-17 US US10/667,111 patent/US7429598B2/en not_active Expired - Fee Related
- 2003-09-17 HN HN2003000285A patent/HN2003000285A/es unknown
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2005
- 2005-02-16 ZA ZA200501381A patent/ZA200501381B/xx unknown
- 2005-02-17 IS IS7700A patent/IS7700A/is unknown
- 2005-03-08 HR HR20050223A patent/HRP20050223A2/hr not_active Application Discontinuation
- 2005-03-10 CR CR7728A patent/CR7728A/es not_active Application Discontinuation
- 2005-03-11 EC ECSP055671 patent/ECSP055671A/es unknown
- 2005-03-16 CO CO05024530A patent/CO5540391A2/es not_active Application Discontinuation
- 2005-03-17 TN TNP2005000073A patent/TNSN05073A1/fr unknown
- 2005-03-17 MA MA28153A patent/MA27439A1/fr unknown
- 2005-04-05 NO NO20051695A patent/NO20051695L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HRP20050223A2 (en) | 2005-10-31 |
| AR041271A1 (es) | 2005-05-11 |
| PL375977A1 (en) | 2005-12-12 |
| EP1400244A1 (en) | 2004-03-24 |
| HN2003000285A (es) | 2004-11-23 |
| EP1542694A1 (en) | 2005-06-22 |
| KR20050057371A (ko) | 2005-06-16 |
| AP2005003251A0 (en) | 2005-03-31 |
| PE20050073A1 (es) | 2005-02-28 |
| CA2499330C (en) | 2009-04-28 |
| EA200500312A1 (ru) | 2005-08-25 |
| UY27986A1 (es) | 2004-04-30 |
| ECSP055671A (es) | 2005-05-30 |
| TW200413333A (en) | 2004-08-01 |
| TNSN05073A1 (fr) | 2007-05-14 |
| IS7700A (is) | 2005-02-17 |
| ZA200501381B (en) | 2006-11-29 |
| WO2004026818A1 (en) | 2004-04-01 |
| TWI251590B (en) | 2006-03-21 |
| MA27439A1 (fr) | 2005-07-01 |
| CO5540391A2 (es) | 2005-07-29 |
| US20040106631A1 (en) | 2004-06-03 |
| JP2006501277A (ja) | 2006-01-12 |
| CR7728A (es) | 2005-06-08 |
| CN1681507A (zh) | 2005-10-12 |
| CA2499330A1 (en) | 2004-04-01 |
| AU2003259496A1 (en) | 2004-04-08 |
| GT200300201A (es) | 2004-05-18 |
| BR0314379A (pt) | 2005-07-19 |
| US7429598B2 (en) | 2008-09-30 |
| NO20051695L (no) | 2005-04-05 |
| PA8582801A1 (es) | 2004-05-26 |
| MXPA05002913A (es) | 2005-05-27 |
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