JPWO2019140188A5 - - Google Patents
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- JPWO2019140188A5 JPWO2019140188A5 JP2020538841A JP2020538841A JPWO2019140188A5 JP WO2019140188 A5 JPWO2019140188 A5 JP WO2019140188A5 JP 2020538841 A JP2020538841 A JP 2020538841A JP 2020538841 A JP2020538841 A JP 2020538841A JP WO2019140188 A5 JPWO2019140188 A5 JP WO2019140188A5
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| US11135207B2 (en) * | 2016-12-13 | 2021-10-05 | Centaurus Therapeutics | Inhibitors of dihydroceramide desaturase for treating disease |
| EA201991650A1 (ru) | 2017-01-06 | 2020-01-20 | Юманити Терапьютикс, Инк. | Способы лечения неврологических расстройств |
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| EP3923921B1 (en) | 2019-02-15 | 2023-07-26 | Lysosomal and Rare Disorders Research and Treatment Center, Inc. | Compositions for treating lysosomal storage disorders: ambroxol as treatment agent for mucopolysaccharidoses iii (sanfilippo syndrome) |
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| EP1849773B1 (en) | 2005-02-17 | 2013-10-16 | Astellas Pharma Inc. | Piperazine derivatives for the treatment of urinary incontinence and pain |
| US7790726B2 (en) | 2005-08-16 | 2010-09-07 | Chemocentryx, Inc. | Monocyclic and bicyclic compounds and methods of use |
| US20100048714A1 (en) | 2006-06-19 | 2010-02-25 | University Of Utah Research Foundation | Methods and Compositions Related to Inhibition of Ceramide Synthesis |
| WO2008023720A1 (en) | 2006-08-23 | 2008-02-28 | Astellas Pharma Inc. | Urea compound or salt thereof |
| BRPI0821871A2 (pt) * | 2008-01-03 | 2015-06-16 | Wockhardt Research Center | Suspensão farmacêutica oral compreendendo paracetamol e ibuprofeno |
| WO2010023512A1 (en) * | 2008-08-28 | 2010-03-04 | Matrix Laboratories Ltd. | Novel vanilloid receptor modulators, process for their preparation and pharmaceutical compositions containing them |
| FR2939135B1 (fr) * | 2008-12-02 | 2010-12-03 | Galderma Res & Dev | Nouveaux composes 4-(azacycloalkyl)-benzene-1,3-diol comme inhibiteurs de la tyrosinase, leur procede de preparation et leur utilisation en medecine humaine ainsi qu'en cosmetique |
| SG172974A1 (en) | 2009-01-28 | 2011-08-29 | Rigel Pharmaceuticals Inc | Carboxamide compounds and methods for using the same |
| JP2010195688A (ja) | 2009-02-23 | 2010-09-09 | Shionogi & Co Ltd | Npyy5受容体拮抗作用を有するアミド及びウレア誘導体 |
| WO2011078369A1 (ja) | 2009-12-25 | 2011-06-30 | 持田製薬株式会社 | 新規アリールウレア誘導体 |
| CN103172635B (zh) * | 2011-12-21 | 2016-04-27 | 上海医药工业研究院 | 哌嗪或哌啶类化合物、其盐、中间体、制备方法及应用 |
| EP3043822A1 (en) * | 2013-09-11 | 2016-07-20 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Compositions for preparing cardiomyocytes |
| MX2018015548A (es) * | 2016-06-30 | 2019-04-11 | Basilea Pharm Int Ag | Inhibidores mitocondriales para el tratamiento de trastornos de proliferacion. |
| US11135207B2 (en) * | 2016-12-13 | 2021-10-05 | Centaurus Therapeutics | Inhibitors of dihydroceramide desaturase for treating disease |
| JP7346425B2 (ja) | 2018-01-11 | 2023-09-19 | セントラス セラピューティクス | 疾患を治療するためのジヒドロセラミドデサチュラーゼ阻害剤 |
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