benzyl 5-[[1-(acetyloxy) ethoxy]carbonyl]amino-4-oxopentanoate | 396078-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 5-[[1-(acetyloxy) ethoxy]carbonyl]amino-4-oxopentanoate
• 英文别名: Benzyl 5-(1-acetyloxyethoxycarbonylamino)-4-oxopentanoate
• CAS: 396078-92-5
• 化学式: C₁₇H₂₁NO₇
• 分子量: 351.356
• InChiKey: HUJZXMQJJRAVDN-UHFFFAOYSA-N

物化性质

• 沸点：
  501.3±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-氯乙基氯甲酸酯 、 mercury(II) diacetate 、 5-氨基酮戊酸苄酯盐酸盐 在 吡啶 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 以0.43 g (61%)的产率得到benzyl 5-[[1-(acetyloxy) ethoxy]carbonyl]amino-4-oxopentanoate
  参考文献：
  名称：

  Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy

  摘要：

  该发明提供了用于光化疗或诊断的化合物，所述化合物为5-氨基丙酸的支链烷基酯或取代烷基酯，或其衍生物或药用可接受的盐。具体而言，该发明提供了式(I)的化合物：R2N—CH2COCH2CH2CO—OR1（其中R1代表可选择取代的支链烷基（例如C5-30烷基）基团，或取代烷基基团；R2，每个可能相同或不同，代表氢原子或可选择取代的烷基基团，优选为基团R1；其中所述取代基被选择自羟基、烷氧基、酰氧基、烷氧羰氧基、氨基、芳基、硝基、氧代、氟代、—SR3、—NR32和PR32基团，每个烷基基团可选择地被一个或多个O—、—NR3—、—S—或—PR3—基团中断；R3代表氢原子或C1-6烷基基团）及其盐，用于诊断和治疗身体外部或内部表面的异常或疾病的光化疗，以及执行该发明的产品和工具包。

  公开号：

  US20040106679A1

文献信息

• Acid Addition Salts Of-5-Aminolevulinic Acid Or Its Derivatives
  申请人：Braenden Jon Erik

  公开号：US20080064752A1

  公开（公告）日：2008-03-13

  The present invention provides an acid addition salt of 5-aminolevulinic acid (5-ALA) or of a 5-ALA derivative (e.g. a 5-ALA ester) with an acid which has a pKa of about 5 or less, preferably about 3 or less, with the proviso that the acid is other than hydrochloric acid. Particularly preferred salts are those derived from acids selected from the group comprising sulphonic acid and its derivatives, hydrobromic acid, sulfuric acid, nitric acid and phosphoric acid. The salts in accordance with the invention are particularly suitable for use as photosensitizing agents in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body.

  本发明提供了5-氨基戊酸（5-ALA）或5-ALA衍生物（例如5-ALA酯）与具有pKa约为5或更低的酸（优选约为3或更低），但该酸不是盐酸的酸加成盐。特别优选的盐是由选自磺酸及其衍生物、氢溴酸、硫酸、硝酸和磷酸的酸所衍生的盐。本发明的盐特别适用于作为诊断和光化学治疗身体内部或外部表面的疾病或异常的光敏剂。
• ACID ADDITION SALTS OF 5-AMINOLEVULINIC ACID OR ITS DERIVATIVES
  申请人：BRAENDEN Jon Erik

  公开号：US20110125012A1

  公开（公告）日：2011-05-26

  The present invention provides an acid addition salt of 5-aminolevulinic acid (5-ALA) or of a 5-ALA derivative (e.g. a 5-ALA ester) with an acid which has a pKa of about 5 or less, preferably about 3 or less, with the proviso that the acid is other than hydrochloric acid. Particularly preferred salts are those derived from acids selected from the group comprising sulphonic acid and its derivatives, hydrobromic acid, sulfuric acid, nitric acid and phosphoric acid. The salts in accordance with the invention are particularly suitable for use as photosensitizing agents in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body.

  本发明提供了一种5-氨基戊酸（5-ALA）或5-ALA衍生物（例如5-ALA酯）与pKa约为5或更低（优选约为3或更低）的酸的酸加成盐，但该酸不是盐酸。特别优选的盐是从磺酸及其衍生物、氢溴酸、硫酸、硝酸和磷酸组成的酸中选择的。根据本发明的盐特别适用于作为诊断和光化学治疗身体内外表面的疾病或异常的光敏剂。
• Acid addition salts of 5-aminolevulinic acid or its derivatives
  申请人：Photocure ASA

  公开号：EP2308830A1

  公开（公告）日：2011-04-13

  The present invention provides an acid addition salt of 5-aminolevulinic acid (5-ALA) or of a 5-ALA derivative (e.g. a 5-ALA ester) with an acid which has a pKa of about 5 or less, preferably about 3 or less, with the proviso that the acid is other than hydrochloric acid. Particularly preferred salts are those derived from acids selected from the group comprising sulphonic acid and its derivatives, hydrobromic acid, sulfuric acid, nitric acid and phosphoric acid. The salts in accordance with the invention are particularly suitable for use as photosensitizing agents in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body.

  本发明提供了5-氨基乙酰丙酸（5-ALA）或5-ALA衍生物（如5-ALA酯）与pKa约为5或更小，最好约为3或更小的酸的酸加成盐，但条件是该酸不是盐酸。特别优选的盐是从磺酸及其衍生物、氢溴酸、硫酸、硝酸和磷酸中选出的酸衍生而来的盐。符合本发明的盐类特别适合用作光敏剂，用于诊断和光化学疗法，治疗身体外部或内部表面的疾病或异常。
• Use of 5-aminolevulinic acid and derivatives in a solid form for photodynamic treatment and diagnosis
  申请人：Photocure ASA

  公开号：EP2684573A2

  公开（公告）日：2014-01-15

  The present invention relates to a solid pharmaceutical product provided in the form of a suppository which comprises a photosensitiser which is a 5-ALA ester of general formula I, or a pharmaceutically acceptable salt thereof:         R22N-CH2COCH2-CH2CO-OR1     (I) (wherein R1 represents a substituted or unsubstituted, straight-chained, branched or cyclic alkyl group; and each R2 independently represents a hydrogen atom); and at least one pharmaceutically acceptable carrier or excipient which is a hard fat or a mixture of hard fat and additives. The pharmaceutical product may be used in the photodynamic treatment of cancer, and infections associated with cancer, and in the treatment of non-cancerous conditions, in particular in treating cancerous or non-cancerous conditions in the female reproductive system, for example cervical cancer and infections caused by the human papillomavirus.

  本发明涉及一种以栓剂形式提供的固体药品，它包含一种光敏剂，该光敏剂是通式 I 的 5-ALA 酯或其药学上可接受的盐： R22N-CH2COCH2-CH2CO-OR1 (I) 其中 R1 代表取代或未取代的直链、支链或环状烷基；及 每个 R2 独立地代表一个氢原子）； 以及至少一种药学上可接受的载体或赋形剂，它是一种硬脂或硬脂与添加剂的混合物。 该药品可用于光动力治疗癌症、与癌症相关的感染以及非癌症疾病的治疗，尤其是治疗女性生殖系统的癌症或非癌症疾病，例如宫颈癌和由人类乳头瘤病毒引起的感染。
• Use of aminolevulinic acid and derivatives thereof
  申请人：Photocure ASA

  公开号：US10543272B2

  公开（公告）日：2020-01-28

  The invention provides the use of a photosensitiser which is a derivative (e.g. an ester) of 5-aminolevulinic acid (5-ALA), or a pharmaceutically acceptable salt thereof, in the manufacture of a composition for use in methods of photodynamic therapy (PDT) on an animal, wherein said PDT comprises: (a) administering to said animal a composition comprising said photosensitiser; and (b) photoactivating said photosensitiser, and side-effects (e.g. pain and/or erythema) of said PDT are prevented or reduced by use of one or more of (i)-(iv): (i) said composition comprises said photosensitiser in a concentration of less than 10% wt (e.g. 0.5 to 8% wt), (ii) said composition is administered for less than 2 hours (e.g. 30 minutes to 90 minutes) prior to said photoactivation, (iii) said photoactivation is carried out with a light source having a fluence rate of less than 50 mW/cm2 (e.g. 5 to 40 mW/cm2), (iv) said photoactivation is carried out with sunlight. Preferably, side effects of PDT are prevented or reduced by using (ii) or (iv) in combination with (i) and/or (ii).

  本发明提供了一种光敏剂的用途，该光敏剂是5-氨基乙酰丙酸（5-ALA）的衍生物（如酯类）或其药学上可接受的盐，可用于制造一种组合物，用于对动物进行光动力疗法（PDT），其中所述PDT包括： (a) 向所述动物施用包含所述光敏剂的组合物；以及 (b) 光活化所述光敏剂、 通过使用(i)-(iv)中的一种或多种方法，防止或减少所述光热效应的副作用（如疼痛和/或红斑）： (i) 组合物中光敏剂的浓度低于 10%（例如 0.5%至 8%）、 (ii) 在所述光激活之前，所述组合物的给药时间少于 2 小时（例如 30 分钟至 90 分钟）、 (iii) 所述光激活使用的光源的通量低于 50 mW/cm2（例如 5 至 40 mW/cm2）、 (iv) 利用阳光进行光激活。 最好是将(ii)或(iv)与(i)和/或(ii)结合使用，以防止或减少光动力疗法的副作用。