3-oxoandrost-4-ene-17β-carbothioic acid | 146175-30-6

• 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: 3-oxoandrost-4-ene-17β-carbothioic acid
• 英文别名: (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carbothioic S-acid
• CAS: 146175-30-6
• 化学式: C₂₀H₂₈O₂S
• 分子量: 332.507
• InChiKey: VVZYSYAECBQTSG-UDCWSGSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.1
• 氢给体数：
  1
• 氢受体数：
  3

文献信息

• 17-Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes, their pharmaceutical use and processes for their preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004773A2

  公开（公告）日：1979-10-17

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula: wherein X' is fluoro, chloro or bromo; X2 is fluoro, chloro or hydrogen; X3 is fluoro, chloro, bromo or hydrogen; X4 is =C=O or or may also be when X3 is chloro; R is alkyl or 1 to 6 carbon atoms or phenyl or benzyl optionally substituted with one substituent on the phenyl ring chosen from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms and halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl, or OR' and R2 together are isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or a single bond; are useful as anti-inflammatory agents. They can be prepared by treating the corresponding 17β-carboxylic acid with a suitable base salt of RSH. The 17β-hydroxy compounds can be esterified to produce the 17β-alkanoyloxy compound. The double bond at the 4,5 position can be produced by contacting the corresponding Δ5 compound with a base.

  17β-Thiocarboxylic acid esters of 4-halo-3-oxoandrost-4- enes of the formula： 其中 X' 是氟、氯或溴； X2 是氟、氯或氢 X3 是氟、氯、溴或氢； X4 是 =C=O 或 或也可以是 当 X3 为氯时； R 是 1 至 6 个碳原子的烷基或苯基或苄基，可选择被苯基环上的一个取代基取代，该取代基可从 1 至 4 个碳原子的烷基、1 至 4 个碳原子的烷氧基和卤素组成的组中选择； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR' 和 R2 合在一起为异亚丙基二氧基；以及 C-1 和 C-2 之间的实线和断线代表双键或单键； 可用作抗炎剂。它们可以通过将相应的 17β- 羧酸与合适的 RSH 碱盐进行处理来制备。17β-hydroxy 化合物经酯化后可生成 17β-alkanoyloxy 化合物。4,5 位的双键可通过将相应的 Δ5 化合物与碱接触而生成。
• Thio etianic acid derivatives, their preparation and pharmaceutical use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004741A2

  公开（公告）日：1979-10-17

  Thio etianic acid derivatives of the formula wherein X' is hydrogen, fluoro, or chloro; X2 is hydrogen, fluoro, chloro or bromo; X3 is =C=O Cl may also be =C when X2 is chloro; H R is alkyl of 1 to 6 carbon atoms, or phenyl or benzyl optionally substituted with a substituent on the phenyl ring which is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon _ atoms or halo; R1 is hydrogen or alkanoyl of 2 to 6 carbon atoms when R2 is hydrogen, a-methyl or β-methyl or OR1 and R2 together are 16a, 17a-isopropylidenedioxy; and the solid and broken lines between C-1 and C-2 represent a double or single bond; are useful an anti-inflammatory steroids. They can be prepared by reacting the corresponding 17β-carboxylic acid or a reactive derivative thereof with an alkali metal salt of RSH.

  式中的硫代乙酸衍生物 式中 X'是氢、氟或氯 X2 是氢、氟、氯或溴 X3 是 =C=O Cl 当 X2 为氯时，也可以是 =C；H R 是 1 至 6 个碳原子的烷基，或苯基或苄基，可选择被苯基环上的 1 至 4 个碳原子的烷基、1 至 4 个碳 _ 原子的烷氧基或卤素取代； 当 R2 为氢、a-甲基或 β-甲基时，R1 为氢或 2 至 6 个碳原子的烷酰基，或 OR1 和 R2 一起为 16a、17a-异亚丙基二氧基；C-1 和 C-2 之间的实线和断线代表双键或单键。它们可以通过相应的 17β 羧酸或其活性衍生物与 RSH 的碱金属盐反应来制备。
• Unsaturated 17beta-substituted 3-carboxy steroids
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0517047A1

  公开（公告）日：1992-12-09

  The present invention concerns steroidic 5α-reductase inhibitors having the following formula (I) wherein Y is oxygen or sulphur; R is a group: a) -OR₄, wherein R₄ is hydrogen or a C₁-C₆ alkyl group; b) wherein each of R₅ and R₆, independently, is hydrogen or a C₁-C₆ alkyl group; c) wherein R₇ is hydrogen or a C₁-C₆ alkyl group and W is a group: (i) wherein R₈ is a C₁-C₆ alkyl group, a C₅-C₆ cycloalkyl group, a C₆-C₉ cycloalkylalkyl group, a phenyl group or a benzyl group; or (ii) wherein R₉ is a C₁-C₆ alkyl group or a C₅-C₆ cycloalkyl group; or (iii) wherein R₅ and R₆ are as defined above; d) wherein each of R₁₀ and R₁₁ is, independently, hydrogen or a C₁-C₆ alkyl group or taken together with the nitrogen atom to which they are linked form a pentatomic or hexatomic saturated heteromonocyclic ring, optionally containing at least one additional heteroatom selected from oxygen and nitrogen, and n is an integer of 2 to 4; R₁ is hydrogen, a C₁-C₆ alkyl group, a C₅-C₆ cycloalkyl group, a C₆-C₉ cycloalkyalkyl group or an aryl group; each of R₂ and R₃ is, independently, selected from the group consisting of hydrogen, C₁-C₆ alkyl, C₅-C₆ cycloalkyl, C₆-C₉ cycloalkylalkyl and aryl or R₂ and R₃, taken together with the nitrogen atom to which they are linked, form a pentatomic or hexatomic saturated heteromonocyclic ring, optionally containing at least one additional heteroatom selected from oxygen and nitrogen; and the symbol (----) represents a single or a double bond provided that when it is a double bond the hydrogen in the 5α position doesn't exist and the pharmaceutically acceptable salts thereof. In view of their 5-α reductase inhibiting activity the compounds of the invention can be useful for the treatment of androgen dependent conditions.

  本发明涉及具有下式（I）的类固醇 5α 还原酶抑制剂 其中 Y 是氧或硫； R 是一个基团： a) -OR₄，其中 R₄ 是氢或 C₁-C₆ 烷基； b) 其中 R₅ 和 R₆ 各自独立地为氢或 C₁-C₆ 烷基； c) 其中 R₇ 是氢或 C₁-C₆ 烷基，W 是一个基团： (i) 其中 R₈ 是 C₁-C₆ 烷基、C₅-C₆ 环烷基、C₆-C₉ 环烷基、苯基或苄基；或 (ii) 其中 R𠢙 是 C₁-C₆ 烷基或 C₅-C₆ 环烷基；或 (iii) 其中 R₅ 和 R₆ 如上文所定义； d) 其中 R₁₀和 R₁₁ 各自独立为氢或 C₁-C₆ 烷基，或与它们相连的氮原子一起形成五原子或六原子饱和杂环，可选地含有至少一个选自氧和氮的额外杂原子，且 n 为 2 至 4 的整数； R₁ 是氢、C₁-C₆ 烷基、C₅-C₆ 环烷基、C₆-C₉ 环烷基或芳基； R₂ 和 R₃ 各自独立地选自氢、C₁-C₆ 烷基、C₅-C₆ 环烷基、C₆-C₉ 环烷基和芳基或 R₂ 和 R₃ 所组成的组、与它们相连的氮原子一起形成五原子或六原子饱和杂环，可选择含有至少一个选自氧和氮的额外杂原子；符号(----)代表单键或双键，条件是当它是双键时，5α 位的氢不存在，以及它们的药学上可接受的盐。 鉴于其 5-α 还原酶抑制活性，本发明化合物可用于治疗雄激素依赖性疾病。
• Steroid derivatives for the treatment of prostatic hypertrophy, their preparation and uses
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0567271A2

  公开（公告）日：1993-10-27

  Compounds of formula (I): [wherein : R1 is hydrogen, alkyl, aryl-substituted alkyl or aromatic heterocyclic-substituted alkyl ; R2 is: aryl-substituted alkyl, aromatic heterocyclic-substituted alkyl or diarylamino; and R3 is carboxy or a group of formula -CONHS02 R4 wherein R4 is alkyl] ; and pharmaceutically acceptable salts and esters thereof have valuable 5α-reductase inhibitory activity and can thus be used for the treatment and prophylaxis of, inter alia, prostatic hypertrophy as well as other disorders arising from excess levels of 5α-dihydro-testosterone.

  式(I)化合物： [其中 ：R1 是氢、烷基、芳基取代的烷基或芳香杂环取代的烷基；R2 是：芳基取代的烷基、芳香杂环取代的烷基或二芳基氨基；以及 R3 是羧基或式 -CONHS02 R4 的基团，其中 R4 是烷基]；及其药学上可接受的盐类和酯类具有重要的 5α 还原酶抑制活性，因此可用于治疗和预防前列腺肥大以及因 5α 二氢睾酮水平过高而引起的其他疾病。
• Compounds suitable for use as intermediates in the preparation of Androst-3,5-dien-3-carboxy derivatives
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0725074A2

  公开（公告）日：1996-08-07

  A compound of formula (IV) and a process for the preparation of a compound of the following formula: in which R10 is a hydroxy group, a group -OR5, in which R5 is a carboxy protecting group, a group -NR1R2, in which R1 is hydrogen, alkyl, aryl-substituted alkyl or aromatic heterocyclic-substituted alkyl and R2 is aryl-substituted alkyl, aromatic heterocyclic-substituted alkyl or diarylamino, or a group -NRR', in which R and R' are hydrogen or alkyl.

  式(IV)化合物 以及制备下式化合物的工艺： 其中 R10 是羟基、基团-OR5（其中 R5 是羧基保护基）、基团-NR1R2（其中 R1 是氢、烷基、芳基取代的烷基或芳香杂环取代的烷基，R2 是芳基取代的烷基、芳香杂环取代的烷基或二芳基氨基）或基团-NRR'（其中 R 和 R' 是氢或烷基）。