6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-en-21,17-carbolactone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-en-21,17-carbolactone
• 英文别名: drospirenone；6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-ene-21,17-carbolactone；Pharmakon1600-01503831；(2R,4R,10R,14S,15S,16S,18S)-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-5-ene-15,5'-oxolane]-2',7-dione
• 化学式: C₂₄H₃₀O₃
• 分子量: 366.5
• InChiKey: METQSPRSQINEEU-GGORKCOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5β-DRSP 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-en-21,17-carbolactone
  参考文献：
  名称：

  WO2006/61309

  摘要：

  公开号：

文献信息

• [EN] METHODS FOR THE PREPARATION OF DROSPIRENONE AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉS DE PRÉPARATION DE LA DROSPIRÉNONE ET DE SES INTERMÉDIAIRES
  申请人：NEWCHEM S P A

  公开号：WO2012016860A1

  公开（公告）日：2012-02-09

  The invention relates to a process for the preparation of Drospirenone in high yields and purity starting from a compound of formula (2) wherein R is a hydroxyl protective group as defined in the claims, through a sequence of oxidation, deprotection, lactonization and water elimination steps, and wherein the steps of oxidation and lactonization are performed with 1,3,5-trichloro 1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (trichloroisocyanuric acid, TCCA) or 1,3-dichloro-1,3,5-triazine-2,4,6- (1H,3H,5H)-trione (dichloroisocyanuric acid, DCCA) or an alkaline metal salt thereof such as the sodium salt dihydrate (DCCA sodium salt) or 1-hydroxy - 1,2-benziodoxo1-3(1H)-one 1-oxide (IBX). New synthetic intermediates useful for the synthesis of Drospirenone are disclosed, too.

  该发明涉及一种从式（2）中R为在权利要求中定义的羟基保护基的化合物出发，通过一系列氧化、去保护、内酯化和脱水步骤制备Drospirenone的高产率和纯度的方法，其中氧化和内酯化步骤是使用1,3,5-三氯-1,3,5-三嗪-2,4,6-(1H,3H,5H)-三酮（三氯异氰尿酸，TCCA）或1,3-二氯-1,3,5-三嗪-2,4,6-(1H,3H,5H)-三酮（二氯异氰尿酸，DCCA）或其碱金属盐如二水合物的钠盐（DCCA钠盐）或1-羟基-1,2-苯碘氧1-3(1H)-酮1-氧化物（IBX）来进行的。还公开了用于合成Drospirenone的新合成中间体。
• 18-Methyl-19-norandrost-4-ene 17, 17-spiro ether (18-methyl-19-nor-20-spirox-4-en-3-one), and pharmaceutical products comprising the same
  申请人：BOHLMANN Rolf

  公开号：US20080153787A1

  公开（公告）日：2008-06-26

  The present invention describes the novel 18-methyl-19-norandrost-4-ene 17,17-spiro ethers of the general formula I in which Z is an oxygen atom, two hydrogen atoms, a group ═NOR or ═NNHSO 2 R, where R is a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms, R 4 is a hydrogen atom, a halogen atom or a trifluoromethyl group, and R 6 and/or R 7 may have a or a configuration, and R 6 and R 7 are independently of one another a hydrogen atom or a straight- or branched-chain alkyl group having 1 to 4 or 3 to 4 carbon atoms or a straight- or branched-chain alkenyl group having 2 to 4 or 3 to 4 carbon atoms or a saturated cycloalkyl group having 3 to 5 carbon atoms or together are a methylene group or a double bond. The novel compounds have progestational and antimineralocorticoid activity.

  本发明描述了一种新颖的18-甲基-19-诺尔雄烷-4-烯-17,17-螺环醚，其通式为I，其中Z是氧原子、两个氢原子、一个基团═NOR或═NNHSO2R，其中R是氢原子或具有1至4或3至4个碳原子的直链或支链烷基基团，R4是氢原子、卤素原子或三氟甲基基团，R6和/或R7可能具有α或β构型，且R6和R7彼此独立地是氢原子或具有1至4或3至4个碳原子的直链或支链烷基基团或具有2至4或3至4个碳原子的直链或支链烯基基团或具有3至5个碳原子的饱和环烷基基团，或者一起是亚甲基基团或双键。这些新化合物具有孕酮作用和抗矿皮质激素活性。
• PROCESS FOR THE PREPARATION OF 17-(3-HYDROXYPROPYL)-17-HYDROXYSTEROIDS
  申请人：HAESELHOFF Claus-Christian

  公开号：US20090012286A1

  公开（公告）日：2009-01-08

  The present invention relates to a process for the preparation of 17α-(3-hydroxypropyl)-17β-hydroxysteroids of the formula I starting from 17-ketosteroids of the formula III via the intermediates of the formula V wherein the radicals R 3 , R 5 , R 6 , R 7 , R 10 , R 13 , R 15 , R 16 , R 40 , R 41 and R 42 have the meaning indicated in the description.

  本发明涉及一种从式III的17-酮类固醇出发，经过式V的中间体，制备式I的17α-(3-羟丙基)-17β-羟基类固醇的方法，其中基团R3、R5、R6、R7、R10、R13、R15、R16、R40、R41和R42具有描述中所示的含义。
• C-ring-substituted pregn-4-ene-21,17-carbolactones, and pharmaceutical preparations comprising the same
  申请人：Ring Sven

  公开号：US20110130371A1

  公开（公告）日：2011-06-02

  The present invention relates to C-ring-substituted pregn-4-ene-21,17-carbolactones of the general formula I in which R 6,7 is an α- or β-methylene and R 9 is a hydrogen atom and R 11 is a bromine, chlorine or fluorine atom or R 9 and R 11 together are a bond. The novel compounds are progestational antimineralocorticoids.

  本发明涉及一般式I的C环取代的孕-4-烯-21,17-羧内酯，其中R6,7为α-或β-亚甲基，R9为氢原子，R11为溴、氯或氟原子或R9和R11一起为键。这些新化合物是孕酮类抗矿皮质激素。
• [EN] PROCESS FOR OBTAINING 17-SPIROLACTONES IN STEROIDS<br/>[FR] PROCÉDÉ D'OBTENTION DE 17-SPIROLACTONES DANS DES STÉROÏDES
  申请人：CRYSTAL PHARMA S A

  公开号：WO2010146042A1

  公开（公告）日：2010-12-23

  The invention relates to processes for obtaining steroids with a spirolactone group in position 17, particularly to industrially obtaining 6β,7β; 15β,16β-dimethylene-3-oxo-17α- pregn-4-ene-21,17-carbolactone, commonly known as Drospirenone, as well as to intermediates useful in said process.

  该发明涉及获取17位上具有螺内酯基团的类固醇的过程，特别是工业上获取6β,7β; 15β,16β-二甲烯-3-酮-17α-孕-4-烯-21,17-碳内酯，通常称为Drospirenone，以及在该过程中有用的中间体。