(R)-3-(5-chloro-2-thienyl)-2-propyl benzoate | 143355-36-6

• 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: (R)-3-(5-chloro-2-thienyl)-2-propyl benzoate
• 英文别名: [(2R)-1-(5-chlorothiophen-2-yl)propan-2-yl] benzoate
• CAS: 143355-36-6
• 化学式: C₁₄H₁₃ClO₂S
• 分子量: 280.775
• InChiKey: OKHIDCSJBSCVGN-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1(S)-2-(5-chloro-2-thienyl)-1-hydroxy-1-methylethane 、 偶氮二甲酸二乙酯 在 三苯基膦 、 苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-3-(5-chloro-2-thienyl)-2-propyl benzoate
  参考文献：
  名称：

  Compounds having antihypertensive and anti-ischemic properties

  摘要：

  本发明涉及腺苷类似物和衍生物，具有腺苷受体激动剂活性，可用作降压和抗缺血剂，包括这些化合物的制药组合物，以及它们在治疗高血压和心肌缺血中的应用，以及用于制备这些化合物的方法和中间体。

  公开号：

  US05364862A1

文献信息

• Compounds having antihypertensive, cardioprotective, anti-ischemic and
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05561134A1

  公开（公告）日：1996-10-01

  Compounds of the Formula ##STR1## wherein: K is N or N.fwdarw.O; Q is CH.sub.2 or O; T is ##STR2## or R.sub.3 O--CH.sub.2 ; X is a straight or branched chain alkylene, cycloalkylene or cycloalkenylene group, each of which is optionally substituted by at least one CH.sub.3, CH.sub.3 CH.sub.2, Cl, F, CF.sub.3 or CH.sub.3 O; Y is NR.sub.4, O or S; a=0 or 1; Z is of the formula ##STR3## Z.sub.1 is N, CR.sub.5, (CH).sub.m --CR.sub.5 or (CH).sub.m --N, m being 1 or 2; Z.sub.2 is N, NR.sub.6, O or S, n being 0 or 1; R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently H, alkyl, aryl or heterocyclyl; R.sub.a and R.sub.b are independently H, OH, alkyl, hydroxyalkyl, alkyl mercaptyl, thioalkyl, alkoxy, alkyoxyalkyl, amino, alkyl amino, carboxyl, acyl, halogen, carbamoyl, alkyl carbamoyl, aryl or heterocyclyl; and R' and R" are independently hydrogen, alkyl, aralkyl, carbamoyl, alkyl carbamoyl, dialkylcarbamoyl, acyl, alkoxycarbonyl aralkoxycarbonyl, aryloxycarbonyl, or R' and R" together may form ##STR4## where R.sub.c is hydrogen or alkyl, ##STR5## where R.sub.d and R.sub.e are independently hydrogen, alkyl, or together with the carbon atom to which they are attached may form a 1,1-cycloalkyl group; provided that when X is straight chain alkylene and Q is oxygen, then Z represents a heterocyclyl including at least two heteroatoms, which are adenosine agonists useful as antihypertensive, cardioprotective, antiischemic, and antilipolytic agents, pharmaceutical compositions including such compounds, and their use in treating hypertension, myocardial ischemia, ameliorating ischemic injury and myocardial infarct size consequent to myocardial ischemia, hyperlipidemia and hypercholesterolemia are claimed.

  该公式的化合物为##STR1##，其中：K为N或N.fwdarw.O; Q为CH.sub.2或O; T为##STR2##或R.sub.3 O--CH.sub.2; X为直链或支链烷基、环烷基或环烯基，每个基团可以选择性地被至少一个CH.sub.3、CH.sub.3 CH.sub.2、Cl、F、CF.sub.3或CH.sub.3 O取代; Y为NR.sub.4、O或S; a=0或1; Z的化学式为##STR3##Z.sub.1为N、CR.sub.5、(CH).sub.m --CR.sub.5或(CH).sub.m --N，其中m为1或2; Z.sub.2为N、NR.sub.6、O或S，其中n为0或1; R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5和R.sub.6独立地为H、烷基、芳基或杂环基; R.sub.a和R.sub.b独立地为H、OH、烷基、羟基烷基、烷基硫醇基、硫代烷基、烷氧基、烷氧烷基、氨基、烷基氨基、羧基、酰基、卤素、氨基甲酰基、芳基或杂环基; R'和R"独立地为氢、烷基、芳基烷基、氨基甲酰基、烷基氨基甲酰基、二烷基氨基甲酰基、酰基、烷氧羰基、芳基氧羰基，或R'和R"在一起可以形成##STR4##其中R.sub.c为氢或烷基，##STR5##其中R.sub.d和R.sub.e独立地为氢、烷基，或者与它们连接的碳原子一起可以形成1,1-环烷基; 前提是当X为直链烷基且Q为氧时，Z表示至少包含两个杂原子的杂环基，这些化合物是腺苷受体激动剂，可用作降压、心脏保护、抗缺血和抗脂解剂，包括这些化合物的制药组合物，以及它们用于治疗高血压、心肌缺血、改善因心肌缺血引起的缺血性损伤和心肌梗死大小、高脂血症和高胆固醇血症的用途。
• DI (1R)-(-)camphosulfonic acid) salt, preparation thereof and use thereof
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05652366A1

  公开（公告）日：1997-07-29

  This invention relates to di[(1 R)-(-)-camphosulfonic acid) salt of [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl )-1-ethylethyl]amino]3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide , and a process for preparing the compound, comprising reacting a reaction mixture of (-)-1.beta.-N-ethyl-2.alpha.,3.alpha.-isopropylidenedioxy-4.beta.-[3-amino -4-[2-(5-chloro-2-thienyl)-(1R)-1-ethylethyl]amino-2-pyridyl]aminocyclopent anecarboxamide and formamidine acetate, and then treating the reaction mixture with (1 R)-(-)-10-camphorsulfonic acid. The salt is useful in purifying [1 S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl)- 1-ethylethyl]amino]-3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide which possesses adenosine agonist activity and is useful as an anti-hypertensive, cardioprotective, anti-ischemic, and antilipolytic agent.

  这项发明涉及[-（1R）-（-）-樟脑磺酸）盐的[1S-[1.alpha.，2.beta.，3.beta.，4.alpha.，（S*）]]-4-[7-[[2-(3-氯-2-噻吩基)-1-乙基乙基]氨基]3 H-咪唑[4,5-b]吡啶-3-基]-N-乙基-2,3-二羟基环戊烷羧酰胺，以及一种制备该化合物的方法，包括将（-）-1.beta.-N-乙基-2.alpha.，3.alpha.-异丙烯基二氧基-4.beta.-[3-氨基-4-[2-(5-氯-2-噻吩基)-(1R)-1-乙基乙基]氨基-2-吡啉基]氨基环戊烷羧酰胺和甲酰胺乙酸盐的反应混合物，然后用（1R）-（-）-樟脑磺酸处理反应混合物。该盐在纯化[1 S-[1.alpha.，2.beta.，3.beta.，4.alpha.，（S*）]]-4-[7-[[2-(3-氯-2-噻吩基)-1-乙基乙基]氨基]-3 H-咪唑[4,5-b]吡啶-3-基]-N-乙基-2,3-二羟基环戊烷羧酰胺方面具有用途，该化合物具有腺苷激动剂活性，并且可用作抗高血压、心脏保护、抗缺血和抗脂解作用剂。
• [EN] COMPOUNDS HAVING ANTIHYPERTENSIVE, CARDIOPROTECTIVE, ANTI-ISCHEMIC AND ANTILIPOLYTIC PROPERTIES<br/>[FR] COMPOSES PRESENTANT DES PROPRIETES ANTI-HYPERTENSIVES, CARDIOPROTECTRICES, ANTI-ISCHEMIQUES ET ANTILIPOLYTIQUES
  申请人：RHONE-POULENC RORER PHARMACEUTICALS INC.

  公开号：WO1995028160A1

  公开（公告）日：1995-10-26

  (EN) This invention relates to adenosine derivatives and analogs which possess adenosine agonist activity and are useful as anti-hypertensive, cardioprotective, anti-ischemic, and antilipolytic agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension, myocardial ischemia, ameliorating ischemic injury and myocardial infarct size consequent to myocardial ischemia, and treating hyperlipidemia and hypercholesterolemia, and to methods and intermediates used in the preparation of such compounds.(FR) La présente invention concerne des dérivés de l'adénosine et analogues qui présentent une activité antagoniste de l'adénosine. Ces composés interviennent dans des compositions pharmaceutiques comme principes anti-hypertenseurs, cardioprotecteurs, anti-ischémiants, et antilipolytiques. Ils permettent de traiter l'hypertension, l'ischémie du myocarde, une évolution favorable des lésions ischémiques et de l'infarctus du myocarde consécutifs à une ischémie du myocarde, et de traiter l'hyperlipidémie et l'hypercholestérolémie. L'invention concerne également des procédés et des intermédiaires utilisés dans la préparation de tels composés.

  该发明涉及腺苷衍生物和类似物，具有腺苷受体激动剂活性，并可用作抗高血压、心脏保护、抗缺血和抗脂肪分解剂，包括这些化合物的制药组合物，以及它们在治疗高血压、心肌缺血、改善心肌缺血所致的缺血性损伤和心肌梗死大小，以及治疗高脂血症和高胆固醇血症方面的应用，以及用于制备这些化合物的方法和中间体。
• Process for preparing 2,4- dihydroxypyridine and 2,4- dihydroxy-3-nitropyridine
  申请人：Aventis Pharmaceuticals Products Inc.

  公开号：US06307054B1

  公开（公告）日：2001-10-23

  The present invention is directed to a process for preparing 2,4-dihydroxy-pyridine comprising heating a compound of the formula A wherein R is H, alkyl or aralkyl and phosphoric acid where the ratio of phosphoric acid to water is not less than about 27 to 1 weight %. The invention is also directed to a process for preparing 2,4-dihydroxy-3-nitropyridine comprising reacting 2,4-dihydroxypyridine with nitric acid. The processes of the present invention prepare intermediates which are useful in preparing compounds which are useful for treating cardiovascular disease marked by hypertension or myocardial ischemia, ameliorating ischenic injury or myocardial infarct size, or treating hyperlipidemia or hypercholesterolemia.

  本发明涉及一种制备2,4-二羟基吡啶的方法，包括加热化合物A，其中R为H、烷基或芳基烷基，以及磷酸，其中磷酸与水的比例不少于27:1重量%。本发明还涉及一种制备2,4-二羟基-3-硝基吡啶的方法，包括将2,4-二羟基吡啶与硝酸反应。本发明的过程制备的中间体可用于制备用于治疗高血压或心肌缺血的心血管疾病，改善缺血性损伤或心肌梗死大小，或治疗高脂血症或高胆固醇血症的化合物。
• Imidazopyridines having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
  申请人：RHONE-POULENC RORER PHARMACEUTICALS, INC.

  公开号：EP1006115A2

  公开（公告）日：2000-06-07

  This invention relates to adenosine derivatives and analogs which possess adenosine agonist activity and are useful as anti-hypertensive and anti-ischemic agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension and myocardial ischemia, and to methods and intermediates used in the preparation of such compounds.

  本发明涉及具有腺苷激动剂活性并可用作抗高血压和抗心肌缺血药物的腺苷衍生物和类似物，涉及包括此类化合物的药物组合物，涉及它们在治疗高血压和心肌缺血中的用途，还涉及用于制备此类化合物的方法和中间体。