acetic acid 2R-benzyl-3R,4-dimethylpentyl ester | 313653-69-9

• 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: acetic acid 2R-benzyl-3R,4-dimethylpentyl ester
• 英文别名: Acetic acid (2R,3R)-2-benzyl-3,4-dimethyl-pentyl-ester；[(2R,3R)-2-benzyl-3,4-dimethylpentyl] acetate
• CAS: 313653-69-9
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: PVMPRUGBJOWLKP-CJNGLKHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetic acid 2R-benzyl-3R,4-dimethylpentyl ester 在 ruthenium trichloride 、 sodium periodate 、 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 、 四氯化碳 、 乙腈 为溶剂， 反应 6.0h， 生成 3R-bromomethyl-4R,5-dimethylhexanoic acid ethyl ester
  参考文献：
  名称：

  Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

  摘要：

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

  DOI：

  10.1021/jm049762l
• 作为产物：
  描述：

  布立西坦杂质19 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢溴酸 、 氢气 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、330.95 kPa 条件下， 反应 5.5h， 生成 acetic acid 2R-benzyl-3R,4-dimethylpentyl ester
  参考文献：
  名称：

  Structure−Activity Relationships of Pregabalin and Analogues That Target the α₂-δ Protein

  摘要：

  Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the alpha(2)-delta subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their alpha(2)-delta binding affinity as demonstrated by their ability to inhibit binding of [H-3]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [H-3]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for alpha(2)-delta binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

  DOI：

  10.1021/jm049762l

文献信息

• [EN] PREGABALIN DERIVATIVES FOR THE TREATMENT OF FIBROMYALGIA AND OTHER DISORDERS<br/>[FR] DERIVES DE PREGABALIN POUR LE TRAITEMENT DE LA FIBROMYALGIE ET D'AUTRES TROUBLES
  申请人：WARNER LAMBERT CO

  公开号：WO2004054566A1

  公开（公告）日：2004-07-01

  This invention relates to a method of treating a disorder selected from OCD, agoraphobia, agoraphobia without history of panic disorder, specific phobia, social phobia, PTSD, restless legs syndrome, premenstrual dysphoric disorder, hot flashes, and fibromyalgia by administering a compound of the formula (1), or a pharmaceutically acceptable salt thereof, wherein; a) R1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and b) R2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S, 5R)-3-Aminomethyl-5-methyl-octanoic acid.

  本发明涉及一种通过给予化合物（1）或其药学上可接受的盐来治疗选择自强迫症、广场恐惧症、无惊恐症状的广场恐惧症、特定恐惧症、社交恐惧症、创伤后应激障碍、不宁腿综合症、经前期情感性障碍、潮热和纤维肌痛等疾病的方法；其中：a）R1为氢、1至6个碳原子的直链或支链烷基或苯基；b）R2为4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷基烷氧基、-烷基羟基、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及一种通过给予化合物（3S，5R）-3-氨甲基-5-甲基-辛酸来治疗上述疾病的方法。
• Method of treating tinnitus
  申请人：——

  公开号：US20030176504A1

  公开（公告）日：2003-09-18

  The invention relates to a method of treating tinnitus by administering an alpha2delta ligand such as, for example, a compound of Formula 1 and pharmaceutically acceptable salts thereof, wherein R 1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.

  本发明涉及一种通过给予alpha2delta配体来治疗耳鸣的方法，例如给予式1化合物及其药学上可接受的盐，其中R1是氢基或直链或支链低烷基，n为4至6的整数。
• Mono-and disubstituted 3-propyl gamma-aminobutyric acids
  申请人：——

  公开号：US20030181523A1

  公开（公告）日：2003-09-25

  The instant invention is a series of novel mono- and disubstituted 3-propyl gamma aminobutyric acids of Formula I 1 The compounds are useful as therapeutic agents in the treatment of epilepsy, faintness attacks, hypokinesia, cranial disorders, neurodegenerative disorders, depression, anxiety, panic, pain, neuropathological disorders, arthritis, sleep disorders, IBS, and gastric damage. Methods of preparing the compounds and useful intermediates are also part of the invention.

  本发明涉及一系列新型单取代和双取代的3-丙基-γ-氨基丁酸化合物，其化学式为I。这些化合物可用作治疗癫痫、晕厥发作、低动力症、颅内疾病、神经退行性疾病、抑郁症、焦虑症、惊恐症、疼痛、神经病理性疾病、关节炎、睡眠障碍、肠易激综合征和胃损伤的治疗剂。本发明还涉及制备这些化合物和有用中间体的方法。
• Method of treating cartilage damage
  申请人：——

  公开号：US20040097405A1

  公开（公告）日：2004-05-20

  The invention relates to a method of preventing or treating cartilage damage by administering a GABA analog such as, for example, a compound of Formula 1 and pharmaceutically acceptable salts thereof, wherein R 1 is hydrogen or straight or branched lower alkyl, and n is an integer of from 4 to 6.

  本发明涉及一种通过给予GABA类似物（例如，公式1中的化合物及其药学上可接受的盐），其中R1为氢或直链或支链低烷基，n为4至6的整数，来预防或治疗软骨损伤的方法。
• Alpha2delta ligands for fibromyalgia and other disorders
  申请人：——

  公开号：US20040186177A1

  公开（公告）日：2004-09-23

  This invention relates to a method of treating a disorder selected from OCD, agoraphobia, agoraphobia without history of panic disorder, specific phobia, social phobia, PTSD, restless legs syndrome, premenstrual dysphoric disorder, hot flashes, and fibromyalgia by administering a compound of the formula 1 1 or a pharmaceutically acceptable salt thereof, wherein: R 1 is hydrogen, straight or branched alkyl of from 1 to 6 carbon atoms or phenyl; and R 2 is straight or branched alkyl of from 4 to 8 carbon atoms, straight or branched alkenyl of from 2 to 8 carbon atoms, cycloalkyl of from 3 to 7 carbon atoms, alkoxy of from 1 to 6 carbon atoms, -alkylcycloalkyl, -alkylalkoxy, -alkyl OH, -alkylphenyl, -alkylphenoxy, or -substituted phenyl. The invention also relates to a method of treating the above disorders by administering the compound (3S, 5R)-3-Aminomethyl-5-methyl-octanoic acid

  本发明涉及一种通过给予化合物11或其药学上可接受的盐来治疗选自强迫症(OCD)、广场恐惧症、无惊恐障碍病史的广场恐惧症、特定恐惧症、社交恐惧症、创伤后应激障碍(PTSD)、不安腿综合症、经前期情感障碍、潮热和纤维肌痛的方法，其中：R1是氢、1至6个碳原子的直链或支链烷基或苯基；R2是4至8个碳原子的直链或支链烷基、2至8个碳原子的直链或支链烯基、3至7个碳原子的环烷基、1至6个碳原子的烷氧基、-烷基环烷基、-烷氧基、-烷基OH、-烷基苯基、-烷基苯氧基或-取代苯基。本发明还涉及一种通过给予化合物(3S, 5R)-3-氨甲基-5-甲基-辛酸来治疗上述疾病的方法。