JP2013522376A5 - - Google Patents
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- JP2013522376A5 JP2013522376A5 JP2013501494A JP2013501494A JP2013522376A5 JP 2013522376 A5 JP2013522376 A5 JP 2013522376A5 JP 2013501494 A JP2013501494 A JP 2013501494A JP 2013501494 A JP2013501494 A JP 2013501494A JP 2013522376 A5 JP2013522376 A5 JP 2013522376A5
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- Prior art keywords
- formula
- compound
- composition
- alkyl
- pharmaceutically acceptable
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 64
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 36
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- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 230000002207 retinal effect Effects 0.000 claims description 18
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 8
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- LAMQVIQMVKWXOC-UHFFFAOYSA-N 4-methyl-n-[2-[3-(morpholin-4-ylmethyl)imidazo[2,1-b][1,3]thiazol-6-yl]phenyl]-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(C=2C=NC=CC=2)SC=1C(=O)NC1=CC=CC=C1C(N=C1SC=2)=CN1C=2CN1CCOCC1 LAMQVIQMVKWXOC-UHFFFAOYSA-N 0.000 claims description 4
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- 230000002401 inhibitory effect Effects 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
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- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 4
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- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 claims description 4
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- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- RPJPZDVUUKWPGT-FOIHOXPVSA-N nim811 Chemical compound CC[C@H](C)[C@@H]1N(C)C(=O)CN(C)C(=O)[C@H](CC)NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC1=O RPJPZDVUUKWPGT-FOIHOXPVSA-N 0.000 claims description 4
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- QBGGPLZEACGASW-TZYHBYERSA-N O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ccc[o]2)c2ccccc12 Chemical compound O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ccc[o]2)c2ccccc12 QBGGPLZEACGASW-TZYHBYERSA-N 0.000 description 1
- DXBSFZHOSDGFLC-TUSQITKMSA-N O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ccccc2)c2c1cccc2 Chemical compound O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ccccc2)c2c1cccc2 DXBSFZHOSDGFLC-TUSQITKMSA-N 0.000 description 1
- NFSJWDWGUGWEGB-XJABCFGWSA-N O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ncc[nH]2)c2c1cccc2 Chemical compound O[C@]1([C@@H](CCc2cnccc2)CC2)N2[C@@H](Cc2ncc[nH]2)c2c1cccc2 NFSJWDWGUGWEGB-XJABCFGWSA-N 0.000 description 1
- ODHANUGBVFWHPA-ZODMCCGTSA-N O[C@]1([C@@H](CCc2cnccc2)CCC2)N2[C@@H](CC2=CC=CC2)c2ccccc12 Chemical compound O[C@]1([C@@H](CCc2cnccc2)CCC2)N2[C@@H](CC2=CC=CC2)c2ccccc12 ODHANUGBVFWHPA-ZODMCCGTSA-N 0.000 description 1
- UWYOTTNSWZZLCG-RZFJZAQRSA-N O[C@]1([C@@H](CCc2cnccc2)CCC2)N2[C@@H](Cc2ccccc2)c2c1cccc2 Chemical compound O[C@]1([C@@H](CCc2cnccc2)CCC2)N2[C@@H](Cc2ccccc2)c2c1cccc2 UWYOTTNSWZZLCG-RZFJZAQRSA-N 0.000 description 1
- XQXXAXMETGZRSO-OYDLWJJNSA-N O[C@]1([C@@H](CCc2cnccc2)COC2)N2[C@@H](CC2=CC=CC2)c2ccccc12 Chemical compound O[C@]1([C@@H](CCc2cnccc2)COC2)N2[C@@H](CC2=CC=CC2)c2ccccc12 XQXXAXMETGZRSO-OYDLWJJNSA-N 0.000 description 1
- ZWCZEBLEOGHBTF-TZYHBYERSA-N O[C@]1([C@@H](CCc2cnccc2)COC2)N2[C@@H](Cc2ccc[o]2)c2ccccc12 Chemical compound O[C@]1([C@@H](CCc2cnccc2)COC2)N2[C@@H](Cc2ccc[o]2)c2ccccc12 ZWCZEBLEOGHBTF-TZYHBYERSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
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| EA027929B1 (ru) | 2012-05-25 | 2017-09-29 | Янссен Сайенсиз Айрлэнд Юси | Нуклеозиды на основе урацила и спирооксетана |
| JP6194003B2 (ja) | 2012-10-09 | 2017-09-06 | ザ プロクター アンド ギャンブル カンパニー | 有益剤及びこれを含む組成物の特定又は評価方法 |
| EP2906197A1 (en) | 2012-10-09 | 2015-08-19 | The Procter & Gamble Company | Method of identifying synergistic cosmetic combinations |
| EA201590943A1 (ru) | 2012-12-21 | 2016-01-29 | Алиос Биофарма, Инк. | Замещенные нуклеозиды, нуклеотиды и их аналоги |
| US9079853B2 (en) * | 2013-02-07 | 2015-07-14 | Musc Foundation For Research Development | Isatin compounds, compositions and methods for treatment of degenerative diseases and disorders |
| US20140275178A1 (en) * | 2013-03-13 | 2014-09-18 | Musc Foundation For Research Development | Thiazole compounds, compositions and methods for treatment of degenerative diseases and disorders |
| US8921401B2 (en) | 2013-02-07 | 2014-12-30 | Musc Foundation For Research Development | Pyrazole compounds, compositions and methods for treatment of degenerative diseases and disorders |
| US20160029919A1 (en) | 2013-03-14 | 2016-02-04 | UNIVERSITé LAVAL | Use of electroretinography (erg) for the assessment of psychiatric disorders |
| DK3180335T3 (da) | 2014-08-11 | 2021-08-09 | Angion Biomedica Corp | Cytokrom-p450-inhibitorer og anvendelser deraf |
| CA2970819A1 (en) | 2014-12-31 | 2016-07-07 | Angion Biomedica Corp. | Methods and agents for treating disease |
| CN104803946A (zh) * | 2015-03-03 | 2015-07-29 | 佛山市赛维斯医药科技有限公司 | 含腈基噻唑和环戊二烯结构的ptp1b抑制剂及其用途 |
| US10370328B2 (en) | 2015-04-30 | 2019-08-06 | Musc Foundation For Research Development | Oxindole compounds and pharmaceutical compositions thereof |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| US20180194769A1 (en) | 2015-07-06 | 2018-07-12 | Rodin Therapeutics, Inc. | Hetero-halo inhibitors of histone deacetylase |
| US10967019B2 (en) | 2015-11-30 | 2021-04-06 | Taiwan Mitochondrion Applied Technology Co., Ltd. | Method for protecting mitochondria in retina cell |
| TWI666023B (zh) * | 2016-09-26 | 2019-07-21 | 台灣粒線體應用技術股份有限公司 | 餘甘子萃取物用於製備保護視網膜中粒線體的醫藥組合物的用途 |
| AU2017231781C1 (en) * | 2016-03-11 | 2021-12-16 | Ac Immune Sa | Bicyclic compounds for diagnosis and therapy |
| JP6756925B2 (ja) | 2017-01-11 | 2020-09-16 | ロダン・セラピューティクス，インコーポレーテッド | ヒストンデアセチラーゼの二環式阻害剤 |
| SMT202200232T1 (it) | 2017-08-07 | 2022-07-21 | Alkermes Inc | Inibitori biciclici di istone deacetilasi |
| KR20220004083A (ko) | 2019-04-11 | 2022-01-11 | 앤지온 바이오메디카 코포레이션 | (e)-3-[2-(2-티에닐)비닐]-1h-피라졸의 고체 형태 |
| TWI874791B (zh) | 2020-02-18 | 2025-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| EP4644394A2 (en) | 2020-02-18 | 2025-11-05 | Gilead Sciences, Inc. | Antiviral compounds |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| KR20230003483A (ko) | 2020-03-26 | 2023-01-06 | 다이아멘티스 인크. | 망막 신호 데이터를 처리하고 병태들을 식별하기 위한 시스템들 및 방법들 |
| KR20230170745A (ko) | 2021-04-16 | 2023-12-19 | 길리애드 사이언시즈, 인코포레이티드 | 아미드를 사용한 카르바뉴클레오시드를 제조하는 방법 |
| WO2023023527A1 (en) | 2021-08-18 | 2023-02-23 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| AU2023211364A1 (en) * | 2022-01-26 | 2024-08-15 | Suzhou Genhouse Bio Co., Ltd. | Methionine adenosyltransferase 2a inhibitor for treating mtap deletion-type cancer |
| KR20240051860A (ko) * | 2022-10-13 | 2024-04-22 | 한미약품 주식회사 | 신규한 트리사이클 유도체 화합물 및 이의 용도 |
| WO2024127350A1 (en) | 2022-12-16 | 2024-06-20 | Astrazeneca Ab | 2,6,9-trisubstituted purines |
Family Cites Families (15)
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| CA962269A (en) * | 1971-05-05 | 1975-02-04 | Robert E. Grahame (Jr.) | Thiazoles, and their use as insecticides |
| US3852293A (en) * | 1972-06-21 | 1974-12-03 | Uniroyal Inc | 4-phenyl-2-(3-pyridyl)-thiazole carboxamides |
| JPS57183768A (en) * | 1981-05-06 | 1982-11-12 | Kanto Ishi Pharma Co Ltd | 4-methyl-5-(o-carboxyphenyl)carbamoylthiazole derivative and its preparation |
| US4788207A (en) * | 1988-02-29 | 1988-11-29 | Fmc Corporation | Photoactivated miticidal and insecticidal ethynylthiazoles |
| DE19845402B4 (de) * | 1998-10-02 | 2005-04-07 | Aventis Pharma Deutschland Gmbh | Mit Heterocyclen substituierte Propanolaminderivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
| TWI243164B (en) * | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
| CA2450400A1 (en) * | 2001-06-11 | 2002-12-19 | Takeda Chemical Industries, Ltd. | Medicinal compositions |
| JP2005528346A (ja) * | 2002-02-25 | 2005-09-22 | イーライ・リリー・アンド・カンパニー | ペルオキシソーム増殖因子活性化受容体調節物質 |
| WO2003101927A1 (en) * | 2002-05-31 | 2003-12-11 | Proteotech, Inc. | Compounds, compositions and methods for the treatment of amyloid diseases and synucleinopathies such as alzheimer's disease, type 2 diabetes, and parkinson's disease |
| AU2006218405A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Acridine and quinoline derivatives as sirtuin modulators |
| AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| GB0701426D0 (en) * | 2007-01-25 | 2007-03-07 | Univ Sheffield | Compounds and their use |
| CL2008001822A1 (es) * | 2007-06-20 | 2009-03-13 | Sirtris Pharmaceuticals Inc | Compuestos derivados de tiazolo[5,4-b]piridina; composicion farmaceutica que comprende a dichos compuestos; y uso del compuesto en el tratamiento de la resistencia a la insulina, sindrome metabolico, diabetes, entre otras. |
| RU2007139634A (ru) * | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| US20110124649A1 (en) * | 2007-11-09 | 2011-05-26 | The Johns Hopkins University | Inhibitors of human methionine aminopeptidase 1 and methods of treating disorders |
-
2011
- 2011-03-24 AU AU2011232347A patent/AU2011232347B2/en not_active Ceased
- 2011-03-24 US US13/636,754 patent/US20130137728A1/en not_active Abandoned
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- 2011-03-24 WO PCT/US2011/029846 patent/WO2011119869A1/en not_active Ceased
- 2011-03-24 JP JP2013501494A patent/JP2013522376A/ja active Pending
- 2011-03-24 EP EP11715106A patent/EP2550260A1/en not_active Withdrawn
-
2015
- 2015-09-28 JP JP2015189524A patent/JP2015232051A/ja active Pending
-
2016
- 2016-01-15 US US14/996,662 patent/US20160237074A1/en not_active Abandoned
- 2016-08-09 JP JP2016156126A patent/JP2016188257A/ja active Pending
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