β-D-Glc-(1->4)-L-Rha | 96-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-Glc-(1->4)-L-Rha
• 英文别名: Glc(b1-4)Rha；(3R,4S,5R,6S)-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,4-triol
• CAS: 96-85-5
• 化学式: C₁₂H₂₂O₁₀
• 分子量: 326.301
• InChiKey: VFLUXFSSKVKHEL-CHDOAOCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4-三-O-乙酰基-6-脱氧-alpha-L-甘露糖基溴化物 在 甲酸 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 β-D-Glc-(1->4)-L-Rha
  参考文献：
  名称：

  8-羟基-3,6-二氧杂戊醛的糖苷。用于合成寡糖的新型间隔基的合成。

  摘要：

  DOI：

  10.1016/0008-6215(91)84138-5

文献信息

• Pharmaceutical dopamine glycoconjugate compositions and methods of their preparation and use
  申请人：christian T. Samuel

  公开号：US20050250739A1

  公开（公告）日：2005-11-10

  Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use, wherein, Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”; each of X and Y is optional; X, when present is either —C(R 1 ) 2 — or —C(R 1 ) 2 —; Y, when present, is either —CH 2 — or —CH 2 —CH 2 —; z, R 5 and R 5′ . are optional, and when present z, R 5 and R 5′ together form a lower alkyl or a substituted lower alkyl moiety; N is part of either an amine or an amide linkage; E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof; R 1 and R 4 are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl; R 2 and R 3 are hydroxyl; R 5 and R 6 , when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialkylamino-carbonyl; and, R 6 and R 6′ are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carboxyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialylamino-carbonyl, with the proviso that Ring 1 is capable of binding to any of: a dopaminergic receptor selected from the group consisting of a D1 receptor and a D5 receptor; a DAT transporter; a VMAT transporter; and, with the proviso that E is capable of binding to a GLUT transporter selected from the group consisting of a GLUT1 receptor and a GLUT3 receptor.

  根据FORMULA V，水亲性可运输的N-连接糖基的多巴胺前药化合物及其使用方法，其中，环1包括一个芳基或杂环芳基环，其中含有4至8个碳原子，其中原子被计为“X”和“Y”；X和Y各自是可选的；当存在X时，它是- C（R1）2-或-C（R1）2-；当存在Y时，它是-CH2-或-CH2-CH2-；z，R5和R5'是可选的，当存在z，R5和R5'时，它们共同形成较低的烷基或取代较低的烷基基团；N是氨基或酰胺连接的一部分；E是一个糖类，通过其碳或氧原子之一的单键与N形成连接；R1和R4从选组中选择，包括氢，羟基，卤素，卤代较低烷基，烷氧基，烷氧基较低烷基，卤代烷氧基，硫酰胺基，氨基磺酰基，烷氧羰基，羧酰胺，氨基羰基和烷基氨基羰基；R2和R3是羟基；当存在时，R5和R6从选组中选择，包括氢，羟基，烷氧基，羰基，烷氧基羰基，氨基羰基，烷基氨基羰基和二烷基氨基羰基；而R6和R6'从选组中选择，包括氢，羟基，烷氧基，羧基，烷氧基羰基，氨基羰基，烷基氨基羰基和二烷基氨基羰基，但前提是环1能够与以下任何一个结合：从选组中选择的多巴胺能感受器，包括D1受体和D5受体；DAT转运体；VMAT转运体；前提是E能够与以下从选组中选择的GLUT转运体结合：GLUT1受体和GLUT3受体。
• Novel pharmaceutical agents containing carbohydrate moieties and methods of their preparation and use
  申请人：Christian T. Samuel

  公开号：US20060189547A1

  公开（公告）日：2006-08-24

  Hydrophilic N-linked pharmaceutical compositions, methods of their preparation and use in neuraxial drug delivery comprising a glycosyl CNS acting prodrug compound covalently N-linked with a saccharide through an amide or an amine bond and a formulary consisting of an additive, a stabilizer, a carrier, a binder, a buffer, an excipient, an emollient, a disintegrant, a lubricating agent, an antimicrobial agent or a preservative, with the proviso that the saccharide moiety is not a cyclodextrin or a glucuronide.

  亲水性N-连接药物组合物，其制备方法和在神经轴向药物输送中的使用，包括一种糖基中枢神经系统作用前药化合物，通过酰胺或胺键与糖苷共价连接，并且配方包括添加剂、稳定剂、载体、粘合剂、缓冲剂、赋形剂、润肤剂、破碎剂、润滑剂、抗微生物剂或防腐剂，但前提是糖苷基团不是环糊精或葡萄糖醛酸盐。
• Novel pharmaceutical anti-infective agents containing carbohydrate moieties and methods of their preparation and use
  申请人：——

  公开号：US20030130205A1

  公开（公告）日：2003-07-10

  Hydrophilic N-linked pharmaceutical compositions, methods of their preparation and use in neuraxial drug delivery comprising a glycosyl CNS acting anti-infective prodrug compound covalently N-linked with a saccharide through an amide or an amine bond and a formulary consisting of an additive, a stabilizer, a carrier, a binder, a buffer, an excipient, an emollient, a disintegrant, a lubricating agent, with the proviso that the saccharide moiety is not a cyclodextrin or a glucuronide.

  亲水性N-连接的制药组合物，其制备方法和在神经轴药物输送中的使用，包括一种糖基CNS作用的抗感染前药化合物，通过酰胺或胺键与糖苷共价连接，并且配方由添加剂、稳定剂、载体、粘合剂、缓冲剂、赋形剂、润肤剂、分散剂、润滑剂组成，但前提是糖苷基团不是环糊精或葡萄糖醛酸盐。
• PHARMACEUTICAL DOPAMINE GLYCOCONJUGATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE
  申请人：Christian Samuel T.

  公开号：US20080194802A1

  公开（公告）日：2008-08-14

  Hydrophilic transportable N-linked glycosyl dopaminergic prodrug compounds according to FORMULA V and methods of their use, wherein, Ring 1 comprises an aryl or heteroaryl ring having 4 to 8 carbon atoms, among which atoms are counted “X” and “Y”; each of X and Y is optional; X, when present is either —C(R 1 ) 2 — or —C(R) 2 —; Y, when present, is either —CH 2 — or —CH 2 —CH 2 —; z, R 5 and R 5′ are optional, and when present z, R 5 and R 5′ together form a lower alkyl or a substituted lower alkyl moiety; N is part of either an amine or an amide linkage; E is a saccharide which forms a linkage with N through a single bond from a carbon or oxygen atom thereof; R 1 and R 4 are selected form the group consisting of hydrogen, hydroxyl, halogen, halo-lower alkyl, alkoxyl, alkoxyl-lower alkyl, halo-alkoxy, thioamido, amidosulfonyl, alkoxylcarbonyl, carboxamide, aminocarbonyl, and alkylamino-carbonyl; R 2 and R 3 are hydroxyl; R 5 and R 6 , when present, are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carbonyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialkylamino-carbonyl; and, R 6 and R 6′ are selected from the group consisting of hydrogen, hydroxyl, alkoxyl, carboxyl, alkoxylcarbonyl, aminocarbonyl, alkylamino-carbonyl and dialylamino-carbonyl, with the proviso that Ring 1 is capable of binding to any of: a dopaminergic receptor selected from the group consisting of a D1 receptor and a D5 receptor; a DAT transporter; a VMAT transporter; and, with the proviso that E is capable of binding to a GLUT transporter selected from the group consisting of a GLUT1 receptor and a GLUT3 receptor.

  根据公式V及其使用方法，水亲和性可转运的N-连接糖基多巴胺前药化合物，其中，环1包括4至8个碳原子的芳基或杂芳基环，其中原子计算为“X”和“Y”；X和Y各自是可选的；当存在X时，它是—C（R1）2—或—C（R）2—；当存在Y时，它是—CH2—或—CH2—CH2—；z，R5和R5'是可选的，当存在时，z，R5和R5'共同形成较低的烷基或取代较低的烷基基团；N是胺或酰胺连接的一部分；E是一种糖，通过其碳或氧原子中的单键与N形成连接；R1和R4从氢、羟基、卤素、卤素较低烷基、烷氧基、烷氧基较低烷基、卤素烷氧基、硫酰胺、氨基磺酰、烷氧基羰基、羧酰胺、氨基羰基和烷基氨基羰基中选择；R2和R3是羟基；当存在R5和R6时，它们从氢、羟基、烷氧基、羰基、烷氧基羰基、氨基羰基、烷基氨基羰基和二烷基氨基羰基中选择；R6和R6'从氢、羟基、烷氧基、羧基、烷氧基羰基、氨基羰基、烷基氨基羰基和二烷基氨基羰基中选择，但环1能够与以下任意一种结合：D1受体和D5受体中选择的多巴胺能受体；DAT转运体；VMAT转运体；并且，E能够与GLUT1受体和GLUT3受体中选择的GLUT转运体结合。
• COMBINED USE OF DIPEPTIDYL PEPTIDASE 4 INHIBITOR AND SWEETENER
  申请人：Shiotani Masaharu

  公开号：US20100113382A1

  公开（公告）日：2010-05-06

  The present invention provides a novel therapeutic or preventive method, a pharmaceutical composition and use thereof, that exhibit superior anti-obesity effects (body weight-reducing (losing) effects and/or body fat mass-reducing effects). Specifically, the present invention provides a pharmaceutical composition comprising the combination of a dipeptidyl peptidase 4 inhibitor and a sweetener having a GLP-1 secretion-stimulating action, as well as use thereof for the manufacture of a medicament. The present invention also provides a method for treating or preventing obesity, comprising administering an effective amount of (a) a dipeptidyl peptidase 4 inhibitor and (b) a sweetener having a GLP-1 secretion-stimulating action to a patient suffering from symptoms of obesity.

  本发明提供了一种新的治疗或预防方法、一种药物组成物及其使用，具有优越的抗肥胖效果（减轻体重和/或减少体脂肪质量）。具体而言，本发明提供了一种药物组成物，包括二肽基肽酶4抑制剂和一种具有GLP-1分泌刺激作用的甜味剂的组合，以及用于制造药物的使用。本发明还提供了一种治疗或预防肥胖的方法，包括向患有肥胖症状的患者投与有效量的（a）二肽基肽酶4抑制剂和（b）一种具有GLP-1分泌刺激作用的甜味剂。