JP2010538001A5 - - Google Patents
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- Publication number
- JP2010538001A5 JP2010538001A5 JP2010523095A JP2010523095A JP2010538001A5 JP 2010538001 A5 JP2010538001 A5 JP 2010538001A5 JP 2010523095 A JP2010523095 A JP 2010523095A JP 2010523095 A JP2010523095 A JP 2010523095A JP 2010538001 A5 JP2010538001 A5 JP 2010538001A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- independently
- heterocycle
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 217
- 125000003118 aryl group Chemical group 0.000 claims description 142
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 94
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 55
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- 125000002950 monocyclic group Chemical group 0.000 claims description 26
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 26
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 22
- 239000000651 prodrug Substances 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 22
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
- -1 -(CH 2 ) n OH Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 23
- 241001465754 Metazoa Species 0.000 claims 17
- 208000020016 psychiatric disease Diseases 0.000 claims 8
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 208000026106 cerebrovascular disease Diseases 0.000 claims 4
- 208000015114 central nervous system disease Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 208000027061 mild cognitive impairment Diseases 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims 2
- 208000017194 Affective disease Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 102000010909 Monoamine Oxidase Human genes 0.000 claims 2
- 108010062431 Monoamine oxidase Proteins 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000029028 brain injury Diseases 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 208000015238 neurotic disease Diseases 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 0 **c1c(*)c(*)c(C2=[Al]C(*)=NO2)[s]1 Chemical compound **c1c(*)c(*)c(C2=[Al]C(*)=NO2)[s]1 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96820507P | 2007-08-27 | 2007-08-27 | |
| US60/968,205 | 2007-08-27 | ||
| PCT/US2008/074353 WO2009029632A1 (en) | 2007-08-27 | 2008-08-26 | Therapeutic isoxazole compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015050436A Division JP2015110666A (ja) | 2007-08-27 | 2015-03-13 | 治療用イソオキサゾール化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010538001A JP2010538001A (ja) | 2010-12-09 |
| JP2010538001A5 true JP2010538001A5 (enExample) | 2011-09-22 |
| JP5718053B2 JP5718053B2 (ja) | 2015-05-13 |
Family
ID=40387754
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010523095A Expired - Fee Related JP5718053B2 (ja) | 2007-08-27 | 2008-08-26 | 治療用イソオキサゾール化合物 |
| JP2015050436A Withdrawn JP2015110666A (ja) | 2007-08-27 | 2015-03-13 | 治療用イソオキサゾール化合物 |
| JP2016138293A Expired - Fee Related JP6250746B2 (ja) | 2007-08-27 | 2016-07-13 | 治療用イソオキサゾール化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015050436A Withdrawn JP2015110666A (ja) | 2007-08-27 | 2015-03-13 | 治療用イソオキサゾール化合物 |
| JP2016138293A Expired - Fee Related JP6250746B2 (ja) | 2007-08-27 | 2016-07-13 | 治療用イソオキサゾール化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (5) | US8222243B2 (enExample) |
| EP (2) | EP3311813B1 (enExample) |
| JP (3) | JP5718053B2 (enExample) |
| KR (2) | KR101669432B1 (enExample) |
| CN (2) | CN104072489B (enExample) |
| AU (2) | AU2008293542B9 (enExample) |
| CA (2) | CA2696609C (enExample) |
| ES (2) | ES2748599T3 (enExample) |
| IL (3) | IL203910A (enExample) |
| MX (1) | MX2010002258A (enExample) |
| WO (1) | WO2009029632A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007013830A1 (en) | 2005-07-26 | 2007-02-01 | Portela & Ca. S.A. | Nitrocatechol derivatives as comt inhibitors |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| DK2481410T3 (en) | 2007-01-31 | 2016-10-24 | Bial - Portela & Ca S A | Nitrocatecholderivater as COMT inhibitors administered in a specific dosage regimen |
| US8222243B2 (en) * | 2007-08-27 | 2012-07-17 | Dart Neuroscience (Cayman) Ltd | Therapeutic isoxazole compounds |
| BRPI0908731A2 (pt) | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| CN102448444B (zh) | 2009-04-01 | 2016-05-25 | 巴尔-波特拉及康邦亚股份有限公司 | 包括硝基儿茶酚衍生物的药物制剂及其制备方法 |
| WO2011076725A1 (en) * | 2009-12-21 | 2011-06-30 | Bayer Cropscience Ag | Thienylpyri (mi) dinylazole and their use for controlling phytopathogenic fungi |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| CN102229606B (zh) * | 2011-06-03 | 2014-07-02 | 浙江工业大学 | 含异噁唑杂环的2-甲基苯并呋喃类衍生物及制备与应用 |
| CN102229603B (zh) * | 2011-06-03 | 2014-07-02 | 浙江工业大学 | 含三唑杂环的2-甲基苯并呋喃类化合物及其制备与应用 |
| EA201490228A1 (ru) | 2011-07-08 | 2014-08-29 | Новартис Аг | Новые производные трифторметилоксадиазола и их применение для лечения заболевания |
| WO2013066839A2 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| CA2856334A1 (en) | 2011-11-28 | 2013-06-06 | Christina Hebach | Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease |
| US9126988B2 (en) | 2011-12-13 | 2015-09-08 | Bial—Portela & Ca, S.A. | Intermediate for preparing a catechol-O-methyltransferase inhibitor |
| NZ711598A (en) | 2013-03-14 | 2016-09-30 | Dart Neuroscience Cayman Ltd | Substituted naphthyridine and quinoline compounds as mao inhibitors |
| AU2014241430B2 (en) | 2013-03-14 | 2018-04-26 | Dart Neuroscience (Cayman) Ltd. | Substituted pyridine and pyrazine compounds as PDE4 inhibitors |
| CN104016938B (zh) * | 2014-05-28 | 2016-08-17 | 浙江工业大学 | 一种含苯硒基的噁二唑类化合物及其制备与应用 |
| CN104016939B (zh) * | 2014-05-28 | 2016-06-15 | 浙江工业大学 | 一种2-亚乙基-3-乙酰基-1,3,4-噁二唑类化合物及其制备与应用 |
| RU2017112054A (ru) * | 2014-09-17 | 2018-10-17 | Дарт Нюросайенс (Кайман) Лтд. | Ингибиторы mao-b и реабилитация |
| WO2016083863A1 (en) | 2014-11-28 | 2016-06-02 | Bial - Portela & Ca, S.A. | Medicaments for slowing parkinson's disease |
| WO2016179428A2 (en) | 2015-05-05 | 2016-11-10 | Dart Neuroscience, Llc | Cognitive test execution and control |
| UY37623A (es) * | 2017-03-03 | 2018-09-28 | Syngenta Participations Ag | Derivados de oxadiazol tiofeno fungicidas |
| WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
| CN110621669A (zh) | 2017-05-04 | 2019-12-27 | 巴斯夫欧洲公司 | 防除植物病原性真菌的取代5-卤代烷基-5-羟基异噁唑类 |
| CR20200275A (es) * | 2017-12-22 | 2020-11-09 | Bayer Ag | Hidroxiisoxazolinas y derivados de estos |
| US10902558B2 (en) * | 2018-05-18 | 2021-01-26 | Gopro, Inc. | Multiscale denoising of raw images with noise estimation |
| US10853215B2 (en) * | 2018-09-10 | 2020-12-01 | Microsoft Technology Licensing, Llc | Intelligent configuration management of user devices |
| US12528798B2 (en) | 2019-10-29 | 2026-01-20 | Lg Chem, Ltd. | Compound for crop protectant |
| EP4676476A1 (en) * | 2023-03-09 | 2026-01-14 | Aquinnah Pharmaceuticals, Inc. | Inhibitors of tdp-43 and tau aggregation |
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-
2008
- 2008-08-26 US US12/198,686 patent/US8222243B2/en not_active Expired - Fee Related
- 2008-08-26 WO PCT/US2008/074353 patent/WO2009029632A1/en not_active Ceased
- 2008-08-26 EP EP17204892.8A patent/EP3311813B1/en not_active Not-in-force
- 2008-08-26 CA CA2696609A patent/CA2696609C/en not_active Expired - Fee Related
- 2008-08-26 CN CN201410184138.1A patent/CN104072489B/zh not_active Expired - Fee Related
- 2008-08-26 KR KR1020157012712A patent/KR101669432B1/ko not_active Expired - Fee Related
- 2008-08-26 ES ES17204892T patent/ES2748599T3/es active Active
- 2008-08-26 CN CN200880110343.6A patent/CN101820764B/zh not_active Expired - Fee Related
- 2008-08-26 CA CA2974477A patent/CA2974477C/en not_active Expired - Fee Related
- 2008-08-26 EP EP08828742.0A patent/EP2182809B1/en not_active Not-in-force
- 2008-08-26 MX MX2010002258A patent/MX2010002258A/es active IP Right Grant
- 2008-08-26 KR KR1020107006239A patent/KR101567454B1/ko not_active Expired - Fee Related
- 2008-08-26 JP JP2010523095A patent/JP5718053B2/ja not_active Expired - Fee Related
- 2008-08-26 ES ES08828742.0T patent/ES2663517T3/es active Active
- 2008-08-26 AU AU2008293542A patent/AU2008293542B9/en not_active Ceased
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2010
- 2010-02-11 IL IL203910A patent/IL203910A/en active IP Right Review Request
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2012
- 2012-04-16 US US13/448,052 patent/US8921399B2/en not_active Expired - Fee Related
- 2012-07-05 US US13/542,358 patent/US9029397B2/en active Active
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- 2013-06-03 IL IL226702A patent/IL226702A/en active IP Right Grant
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2014
- 2014-05-01 IL IL232406A patent/IL232406A/en active IP Right Grant
- 2014-05-26 AU AU2014202864A patent/AU2014202864B2/en not_active Ceased
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2015
- 2015-03-13 JP JP2015050436A patent/JP2015110666A/ja not_active Withdrawn
- 2015-05-11 US US14/709,206 patent/US9650349B2/en not_active Expired - Fee Related
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2016
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