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1. 发明申请

WO2009126737A3 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 审中-公开
标题翻译：三萜皂苷，合成方法及其用途
公开(公告)号：WO2009126737A3
公开(公告)日：2010-01-14
申请号：PCT/US2009039954
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER , GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
IPC分类号： C07H15/24 , A61K31/704 , A61P37/04
CPC分类号： C07H15/256 , A61K31/7024 , A61K31/704 , A61K39/385 , C07H13/08 , C07H15/24
摘要： The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.
摘要翻译：本发明涉及三萜糖苷皂苷衍生的佐剂，其合成，其中间体及其用途。 QS-7是一种有效的免疫佐剂，其毒性明显低于QS-21，这是一种相关的皂苷，目前是抗癌和抗病毒疫苗中有利的佐剂。繁琐的分离和纯化方案阻碍了QS-7的临床发展。提供了一种新的半合成方法，其中使用水解的前配皂素混合物合成QS-7，QS-21及相关类似物，极大地方便了QS-7和QS-21类似物的临床前和临床评估。

2. 发明专利

CA3096084C TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：CA3096084C
公开(公告)日：2022-12-20
申请号：CA3096084
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER RES
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
IPC分类号： C07J63/00 , A61K39/39 , C07H15/256 , C07J53/00
摘要： Abstract The present invention relates to triterpene glycoside saponin-derived adjuvants of formula X: 0 Y~Z Me Me Me 110 11 Me V Me Me X syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development ofQS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

3. 发明专利

AU2015203675A1 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：AU2015203675A1
公开(公告)日：2015-07-23
申请号：AU2015203675
申请日：2015-06-30
申请人： SLOAN KETTERING INST CANCER
发明人： WON ANNIE , GIN DAVID , RAGUPATHI GOVIND , LIVINGSTON PHILIP , ADAMS MICHELLE , PERL NICHOLAS , DENG KAI
IPC分类号： C07H15/24 , A61K31/704 , A61P37/04
摘要： [00361] The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immune-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favoured adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

4. 发明专利

CA2993582C TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：CA2993582C
公开(公告)日：2020-12-15
申请号：CA2993582
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER RES
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
IPC分类号： C07J63/00 , A61K39/39 , C07H15/256 , C07J53/00
摘要： The present invention relates to triterpene glycoside saponin-derived adjuvants of formula X: (see formula X) syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

5. 发明专利

AU2018201645A1 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：AU2018201645A1
公开(公告)日：2018-03-29
申请号：AU2018201645
申请日：2018-03-07
申请人： SLOAN KETTERING INST CANCER RES
发明人： WON ANNIE , GIN DAVID , RAGUPATHI GOVIND , LIVINGSTON PHILIP , ADAMS MICHELLE , PERL NICHOLAS , DENG KAI
IPC分类号： C07H15/24 , A61K31/704 , A61P37/04
摘要： [003611 The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immune-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favoured adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

6. 发明专利

CA2720771C TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：CA2720771C
公开(公告)日：2018-03-20
申请号：CA2720771
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER RES
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
IPC分类号： C07H15/24 , A61K31/704
摘要： The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

7. 发明专利

AU2021266246A1 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：AU2021266246A1
公开(公告)日：2021-12-02
申请号：AU2021266246
申请日：2021-11-10
申请人： SLOAN KETTERING INST CANCER RES
发明人： RAGUPATHI GOVIND , WON ANNIE , GIN DAVID , LIVINGSTON PHILIP , ADAMS MICHELLE , PERL NICHOLAS , DENG KAI
IPC分类号： C07H15/24 , A61K31/704 , A61P37/04
摘要： The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

8. 发明专利

ES2827804T3 Métodos de síntesis de prosapogeninas triterpénicas y saponinas triterpénicas 未知
公开(公告)号：ES2827804T3
公开(公告)日：2021-05-24
申请号：ES18161023
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER RES
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , RAGUPATHI GOVIND , LIVINGSTON PHILIP
IPC分类号： C07H15/256 , C07H1/00
摘要： Un metodo que comprende las etapas de: (a) proporcionar una mezcla de prosapogeninas de formula IV-a: **(Ver fórmula)** en la que: es un enlace simple o doble; Y' es hidrogeno, halogeno, alquilo, arilo, OR, ORy, OH, NR2, NHR, NH2, SR o NROR; W es Me, -CHO, **(Ver fórmula)** -CH2ORx o -C(O)Ry; V es hidrogeno u -ORx; Ry es -OH, o un grupo protector de carboxilo, en el que el grupo protector de carboxilo, cuando se toma con su grupo carbonilo unido, es un ester, amida o hidrazida; Rs1 es **(Ver fórmula)** cada aparicion de Rx' es independientemente un grupo opcionalmente sustituido seleccionado entre arilo de 6-10 miembros, alifatico C1-6 o heteroalifatico C1-6 que tiene 1-2 heteroatomos seleccionados independientemente del grupo que consiste en nitrogeno, oxigeno y azufre; o: dos Rx' se toman juntos para formar un anillo heterociclico de 5-7 miembros que tiene 1-2 heteroatomos seleccionados independientemente del grupo que consiste en nitrogeno, oxigeno y azufre; cada aparicion de R es independientemente hidrogeno, un grupo opcionalmente sustituido seleccionado de acilo, arilalquilo, arilo de 6-10 miembros, alifatico C1-12 o heteroalifatico C1-12 que tiene 1-2 heteroatomos seleccionados independientemente del grupo que consiste en nitrogeno, oxigeno y azufre; o: dos R en el mismo atomo de nitrogeno se toman con el nitrogeno para formar un anillo heterociclico de 4-7 miembros que tiene 1-2 heteroatomos seleccionados independientemente del grupo que consiste en nitrogeno, oxigeno y azufre; y cada aparicion de Rx es independientemente hidrogeno o un grupo protector de oxigeno seleccionado del grupo que consiste en eteres de alquilo, eteres de bencilo, eteres de sililo, acetales, cetales, esteres y carbonatos; (b) tratar dicha mezcla de prosapogeninas de formula IV-a en condiciones apropiadas para formar una mezcla de prosapogeninas de formula IV: **(Ver fórmula)** en la que cada uno de , Ry' Y', V, y W es como se define para los compuestos de formula IV-a, y cada aparicion de Rx es independientemente hidrogeno o un grupo protector de oxigeno seleccionado del grupo que consiste en eteres de alquilo, eteres de bencilo, eteres de sililo, acetales, cetales, esteres y carbonatos; Rs es **(Ver fórmula)** con la condicion de que al menos un grupo Rx no sea hidrogeno; y (c) obtener una prosapogenina de formula IV por medios fisicos apropiados.

9. 发明专利

AU2018201645B2 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：AU2018201645B2
公开(公告)日：2020-01-23
申请号：AU2018201645
申请日：2018-03-07
申请人： SLOAN KETTERING INST CANCER RES
发明人： WON ANNIE , GIN DAVID , RAGUPATHI GOVIND , LIVINGSTON PHILIP , ADAMS MICHELLE , PERL NICHOLAS , DENG KAI
IPC分类号： C07H15/24 , A61K31/704 , A61P37/04
摘要： [003611 The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immune-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favoured adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

10. 发明专利

CA3096084A1 TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF 未知
公开(公告)号：CA3096084A1
公开(公告)日：2009-10-15
申请号：CA3096084
申请日：2009-04-08
申请人： SLOAN KETTERING INST CANCER RES
发明人： GIN DAVID , ADAMS MICHELLE , DENG KAI , PERL NICHOLAS , WON ANNIE , LIVINGSTON PHILIP , RAGUPATHI GOVIND
摘要： The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

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