KR102453184B1 - 트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 - Google Patents
트리테르펜 사포닌, 그의 합성 방법, 및 그의 용도 Download PDFInfo
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- KR102453184B1 KR102453184B1 KR1020217015136A KR20217015136A KR102453184B1 KR 102453184 B1 KR102453184 B1 KR 102453184B1 KR 1020217015136 A KR1020217015136 A KR 1020217015136A KR 20217015136 A KR20217015136 A KR 20217015136A KR 102453184 B1 KR102453184 B1 KR 102453184B1
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- oxygen
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- adjuvant
- sulfur
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| US10517936B2 (en) | 2013-01-04 | 2019-12-31 | OBI Pharma., Inc. | Vaccines with higher carbohydrate antigen density and novel saponin adjuvant |
| US10806119B2 (en) | 2013-06-05 | 2020-10-20 | Yeda Research And Development Co. Ltd. | Plant with altered content of steroidal alkaloids |
| SG11201510740YA (en) | 2013-09-17 | 2016-01-28 | Obi Pharma Inc | Compositions of a carbohydrate vaccine for inducing immune responses and uses thereof in cancer treatment |
| IL290897B2 (en) * | 2014-05-30 | 2023-10-01 | Memorial Sloan Kettering Cancer Center | Minimal saponin analogues, their synthesis and use |
| US10676723B2 (en) | 2015-05-11 | 2020-06-09 | David Gordon Bermudes | Chimeric protein toxins for expression by therapeutic bacteria |
| EP3344806A4 (en) | 2015-09-04 | 2019-03-20 | OBI Pharma, Inc. | GLYCAN NETWORKS AND METHODS OF USE |
| AU2016349693B2 (en) | 2015-11-06 | 2022-08-11 | Adjuvance Technologies, Inc. | Triterpene saponin analogues |
| US11041017B2 (en) | 2016-03-29 | 2021-06-22 | Obi Pharma, Inc. | Antibodies, pharmaceutical compositions and methods |
| US10980894B2 (en) | 2016-03-29 | 2021-04-20 | Obi Pharma, Inc. | Antibodies, pharmaceutical compositions and methods |
| IL262296B2 (en) | 2016-04-22 | 2024-09-01 | Obi Pharma Inc | Cancer immunotherapy by immune activation or immune modulation via globo series antigens |
| CN110072545A (zh) | 2016-07-27 | 2019-07-30 | 台湾浩鼎生技股份有限公司 | 免疫原性/治疗性聚糖组合物及其用途 |
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| AU2017361549B2 (en) | 2016-11-21 | 2023-12-21 | Obi Pharma, Inc. | Conjugated biological molecules, pharmaceutical compositions and methods |
| US11129906B1 (en) | 2016-12-07 | 2021-09-28 | David Gordon Bermudes | Chimeric protein toxins for expression by therapeutic bacteria |
| KR20190137808A (ko) * | 2017-04-13 | 2019-12-11 | 아쥬반스 테크놀로지스 인코포레이티드 | 트리테르펜 사포닌, 중간체 및 보조제 배합물 |
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| CN110730666A (zh) * | 2017-04-25 | 2020-01-24 | 佐剂技术公司 | 三萜皂苷类似物 |
| CA3075822A1 (en) * | 2017-10-16 | 2019-04-25 | Adjuvance Technologies, Inc. | Triterpene saponin analogues |
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| WO2019183159A1 (en) * | 2018-03-20 | 2019-09-26 | The Uab Research Foundation | Saponin-based vaccine adjuvants |
| TWI853822B (zh) | 2018-06-27 | 2024-09-01 | 台灣浩鼎生技股份有限公司 | 用於糖蛋白工程的糖苷合成酶變體及其使用方法 |
| CA3111386A1 (en) | 2018-09-06 | 2020-03-12 | Yeda Research And Development Co. Ltd. | Cellulose-synthase-like enzymes and uses thereof |
| EP3849521A1 (en) | 2018-09-14 | 2021-07-21 | Massachusetts Institute Of Technology | Nanoparticle vaccine adjuvant and methods of use thereof |
| WO2020139960A1 (en) | 2018-12-27 | 2020-07-02 | Glycomimetics, Inc | Galectin-3 inhibiting c-glycosides |
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| CN114630671A (zh) * | 2019-11-05 | 2022-06-14 | 佐剂技术公司 | 水痘带状疱疹 |
| US20230128815A1 (en) * | 2020-03-23 | 2023-04-27 | Adjuvance Technologies, Inc. | Adjuvant compounds, salt forms, and formulations |
| WO2023052829A1 (en) * | 2021-10-02 | 2023-04-06 | Desert King Chile S.A | A 3-o-monodesmosidic saponins extract, stable at physiological ph, method for preparing it from a quillaja plant extract cultured with a microbial consortium, uses and such microbial consortium |
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| US20230190920A1 (en) | 2021-12-19 | 2023-06-22 | Massachusetts Institute Of Technology | Compositions and methods for long-lasting germinal center responses to a priming immunization |
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| JPS6112695A (ja) * | 1984-06-28 | 1986-01-21 | Rikagaku Kenkyusho | シアル酸誘導体 |
| US5583112A (en) | 1987-05-29 | 1996-12-10 | Cambridge Biotech Corporation | Saponin-antigen conjugates and the use thereof |
| US5057540A (en) * | 1987-05-29 | 1991-10-15 | Cambridge Biotech Corporation | Saponin adjuvant |
| JPH09169648A (ja) * | 1995-12-22 | 1997-06-30 | Nippon Shinyaku Co Ltd | 医薬組成物 |
| US6231859B1 (en) | 1996-12-02 | 2001-05-15 | Aquila Biopharmaceuticals, Inc. | Saponin adjuvant compositions |
| DE69637435T2 (de) * | 1996-12-02 | 2009-02-19 | Antigenics Inc. | Saponin-zusammensetzungen und deren verwendung |
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| WO1998052573A1 (en) | 1997-05-20 | 1998-11-26 | Galenica Pharmaceuticals, Inc. | Triterpene saponin analogs having adjuvant and immunostimulatory activity |
| WO1998056415A1 (en) * | 1997-06-11 | 1998-12-17 | Aquila Biopharmaceuticals, Inc. | Purified saponins as oral adjuvants |
| AU5565599A (en) | 1998-08-14 | 2000-03-06 | Dante J. Marciani | Chemically modified saponins and the use thereof as adjuvants |
| US7457415B2 (en) | 1998-08-20 | 2008-11-25 | Akikaze Technologies, Llc | Secure information distribution system utilizing information segment scrambling |
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| CN101322734B (zh) | 2008-07-22 | 2013-05-29 | 沈阳药科大学 | 具有抗炎免疫作用的轮叶党参总皂苷及其制备方法 |
| IL290897B2 (en) * | 2014-05-30 | 2023-10-01 | Memorial Sloan Kettering Cancer Center | Minimal saponin analogues, their synthesis and use |
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Non-Patent Citations (1)
| Title |
|---|
| Yong-Jae Kim et.al., Synthetic Studies of complex Immunostimulants from Quillajasaponaria~, J.AM.CHEM.SOC., Vol.128, pp.11906-11915(2006.) 1부.* |
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