N-(13-cis-retinoyl)-L-cysteic acid methyl ester | 648881-23-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(13-cis-retinoyl)-L-cysteic acid methyl ester
• 英文别名: Methyl N-(13-cis-retinoyl)-L-cysteoate；(2R)-2-[[(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]-3-methoxy-3-oxopropane-1-sulfonic acid
• CAS: 648881-23-6
• 化学式: C₂₄H₃₅NO₆S
• 分子量: 465.611
• InChiKey: MNBLNLUJFNSERO-VQAQWQJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

文献信息

• Therapeutic compounds
  申请人：——

  公开号：US20040048923A1

  公开（公告）日：2004-03-11

  A group of new compounds, N-(all-trans-Retinoyl)-L-cysteic acid, N-(13-cis-Retinoyl)-L-cysteic acid, N-(all-trans-Retinoyl)-L-cysteinesulfinic acid, N-(13-cis-Retinoyl)-L-cysteinesulfinic acid, N-(all-trans-Retinoyl)-L-homocysteic acid, N-(13-cis-Retinoyl)-L-homocysteic acid, and sodium salts of these compounds, including sodium salts of their esters and amides, is shown to exhibit therapeutic effects per se, and which compounds in combination with cytotoxic compounds, such as docetaxel, paclitaxel, doxorubicin and mitoxantrone, exhibit a synergistic effect. These compounds make it possible to manufacture new formulations of poorly soluble pharmaceutical compounds, and the present invention discloses a process of manufacturing water-soluble formulations of such compounds, exemplified by docetaxel, and paclitaxel, exhibiting enhanced pharmacological activity, and formulations of water-soluble pharmaceuticals exemplified by doxorubicin and mitoxantrone, exhibiting improved therapeutic efficacy.

  一组新化合物，N-(全反式视黄醛)-L-半胱氨酸酸，N-(13-顺式视黄醛)-L-半胱氨酸酸，N-(全反式视黄醛)-L-半胱氨酸亚磺酸，N-(13-顺式视黄醛)-L-半胱氨酸亚磺酸，N-(全反式视黄醛)-L-同型半胱氨酸，N-(13-顺式视黄醛)-L-同型半胱氨酸，以及这些化合物的钠盐，包括它们的酯和酰胺的钠盐，被证明本身具有治疗效果，并且这些化合物与细胞毒性化合物（如多西紫杉醇、紫杉醇、阿霉素和米托蒽醌）结合时表现出协同作用。这些化合物使得可以制造新的难溶性药物化合物的制剂，本发明揭示了一种制造这些化合物的水溶性制剂的过程，以多西紫杉醇和紫杉醇为例，表现出增强的药理活性，以阿霉素和米托蒽醌为例的水溶性药物制剂，表现出改善的治疗功效。
• [EN] METHOD FOR PRODUCING N-RETINOYLCYSTEIC ACID ALKYL ESTER<br/>[FR] PROCÉDÉ DE PRODUCTION D'ESTER ALKYLIQUE DE L'ACIDE N-RÉTINOYLCYSTÉIQUE
  申请人：ARDENIA INVESTMENTS LTD

  公开号：WO2017099662A1

  公开（公告）日：2017-06-15

  A method for producing derivatives of N-retinoylaminoalkane sulfonic acid, the method comprising providing retinoic acid, chloroformate, aminoalkanesulfonic acid selected from the group consisting of cysteic acidand alkyl ester thereof, cysteinesulfinic acid and alkyl ester thereof, homocysteic acid and alkyl ester thereof, homocysteinesulfinic acid and alkyl esters thereof, taurine and derivatives thereof, and an organic solvent,and a base, mixing said components under substantial absence of oxidizing compoundsthereby forming a reaction mixture comprising a liquid phase, wherein the liquid phase is one phaseand the derivatives of N-retinoylaminoalkane sulfonic acid are formed in said liquid phase.

  一种生产N-视黄酰氨基烷磺酸衍生物的方法，所述方法包括提供视黄酸、氯甲酸酯、来自半胱氨酸和其烷基酯组成的氨基烷磺酸、半胱氨酸亚磺酸及其烷基酯、同型半胱氨酸及其烷基酯、同型半胱氨酸亚磺酸及其烷基酯、牛磺酸及其衍生物、有机溶剂和一种碱，将所述组分在实质上缺乏氧化物的情况下混合，从而形成包含液相的反应混合物，其中所述液相是一相，且N-视黄酰氨基烷磺酸衍生物在所述液相中形成。
• DRUG DELIVERY SYSTEM FOR ADMINISTRATION OF A WATER SOLUBLE, CATIONIC AND AMPHIPHILIC PHARMACEUTICALLY ACTIVE SUBSTANCE
  申请人：Aleksov Julian

  公开号：US20110123607A1

  公开（公告）日：2011-05-26

  A drug delivery system (DDS) for administration of a water soluble, cationic, and amphiphilic pharmaceutically active substance (API) which DDS comprises poorly water soluble nanoparticles formed by the API together with a Na-salt of N-all-trans-retinoyl cysteic acid methyl ester and/or a Na-salt of N-13-cis-retinoyl cysteic acid methyl ester. A pharmaceutical composition comprising such a DDS. Methods for preparation of such a DDS and such a pharmaceutical composition. Use of such a DDS and pharmaceutical composition for treatment of cancer.

  一种药物输送系统（DDS），用于给予一种水溶性、阳离子和两性亲和性药物活性物质（API）。该DDS包括由API和N-全反式视黄醇半胱氨酸甲酯钠盐和/或N-13-顺式视黄醇半胱氨酸甲酯钠盐形成的难溶性纳米颗粒。一种包括这样的DDS的药物组合物。制备这样的DDS和这样的药物组合物的方法。使用这样的DDS和药物组合物治疗癌症。
• Method for producing N-retinoylcysteic acid alkyl ester
  申请人：ARDENIA INVESTMENTS, LTD.

  公开号：US10138204B2

  公开（公告）日：2018-11-27

  A method for producing derivatives of N-retinoylaminoalkane sulfonic acid, the method comprising providing retinoic acid, chloroformate, aminoalkanesulfonic acid selected from the group consisting of cysteic acid and alkyl ester thereof, cysteinesulfinic acid and alkyl ester thereof, homocysteic acid and alkyl ester thereof, homocysteinesulfinic acid and alkyl esters thereof, taurine and derivatives thereof, and an organic solvent, and a base, mixing said components under substantial absence of oxidizing compounds thereby forming a reaction mixture comprising a liquid phase, wherein the liquid phase is one phase and the derivatives of N-retinoylaminoalkane sulfonic acid are formed in said liquid phase.

  一种生产N-视黄基氨基烷磺酸衍生物的方法，该方法包括提供视黄酸、氯甲酸、选自半胱氨酸及其烷基酯、半胱氨酸亚磺酸及其烷基酯、高半胱氨酸及其烷基酯、高半胱氨酸亚磺酸及其烷基酯组成的氨基烷磺酸、牛磺酸及其衍生物、有机溶剂和碱，在基本上没有氧化性化合物的条件下混合所述组分，从而形成包含液相的反应混合物，其中液相为单相，N-retinoylaminoalkane 磺酸的衍生物在所述液相中形成。
• RETINOL DERIVATIVES, THEIR USE IN THE TREATMENT OF CANCER AND FOR POTENTIATING THE EFFICACY OF OTHER CYTOTOXIC AGENTS
  申请人：Ardenia Investments Ltd.

  公开号：EP1534672B1

  公开（公告）日：2013-05-01