6α-fluoro-9α-bromo-11β-hydroxy-16β-methyl-17α,21-diacetoxypregna 1,4-diene-3,20-dione | 62007-59-4

• 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: 6α-fluoro-9α-bromo-11β-hydroxy-16β-methyl-17α,21-diacetoxypregna 1,4-diene-3,20-dione
• 英文别名: 6alpha-Fluoro-9alpha-bromo-11beta-hydroxy-16beta-methyl-17alpha,21-diacetoxypregna-1,4-diene-3,20-dione；[2-[(6S,8S,9R,10S,11S,13S,14S,16S,17R)-17-acetyloxy-9-bromo-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 62007-59-4
• 化学式: C₂₆H₃₂BrFO₇
• 分子量: 555.438
• InChiKey: RGBZVPWBEYSIMF-JOYXJVLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 17,21-dihydroxy-6α-fluoro-16β-methylpregna-1,4,9(11)-triene-3,20-dione 17,21-diacetate 、 、 、 Dibromohydantoin 、 乙酸乙酯 在 水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.17h， 以to give 11.4 g of 6α-fluoro-9α-bromo-11β-hydroxy-16β-methyl-17α,21-diacetoxypregna-1,4-diene-3,20-dione的产率得到6α-fluoro-9α-bromo-11β-hydroxy-16β-methyl-17α,21-diacetoxypregna 1,4-diene-3,20-dione
  参考文献：
  名称：

  4-Halo steroids

  摘要：

  某些4-氟或4-氯取代的孕酮-4-烯-3,20-二酮或孕酮-1,4-烯-3,20-二酮可用作局部抗炎类固醇。这些化合物在9α位取代为氢、氟、氯或溴；在6α位取代为氢、氟或氯；在11位取代为酮、β-羟基或β-氯（只有在存在9α-氯时才有后者）；在16α、17α位取代为异丙亚甲基二氧基或在17α位为羟基（或酯）时在16α位（或16β位）取代为甲基；在21位取代为2-6个碳的单氟、氯、溴、羟基或脂肪酰氧基或二氟、二氯、二羟基或二甲氧基。

  公开号：

  US04273770A1

文献信息

• 17.beta.-thiocarboxylic acid esters of
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04261984A1

  公开（公告）日：1981-04-14

  Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17.beta.-thiocarboxylic acid esters substituted at the 4-position with a fluoro or chloro, optionally substituted at the 6- position with fluoro or chloro and at 16.beta. with methyl are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9.alpha.-chloro); when there is a 17.alpha.-hydroxy (or an ester).

  在4-位置用氟或氯取代的某些3-氧代雄甾-4-烯和3-氧代雄甾-1,4-二烯17.beta.-硫代羧酸酯，可选择在6-位置用氟或氯取代，在16.beta.位置用甲基取代，可用作抗炎类固醇。这些化合物可选择在9.alpha.位置用氟、氯或溴取代；在11位置用酮、β-羟基或β-氯代替（只有在有9.alpha.-氯时才有后者）；当有17.alpha.-羟基（或酯）时。
• 3-Oxo-4-halo-16.beta.-methylandrost-4-ene 17.beta.-carboxylic acids and
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04278669A1

  公开（公告）日：1981-07-14

  Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17.beta.-carboxylic acids (and esters thereof) substituted at the 4-position with a fluoro or chloro, optionally substituted at the 6- position with fluoro or chloro and at 16.beta. with methyl are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9.alpha. position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9.alpha.-chloro); when there is a 17.alpha.-hydroxy (or an ester).

  在4位取代有氟或氯，6位和16.beta.取代有甲基的某些3-氧代雄甾-4-烯和3-氧代雄甾-1,4-二烯-17.beta.-羧酸（及其酯）可用作抗炎类固醇。这些化合物在9.alpha.位置可选地取代有氟、氯或溴；在11位取代有酮基、β-羟基或β-氯基（只有在有9.alpha.-氯基时才有后者）；当存在17.alpha.-羟基（或酯）时。
• 4-Halo etianic acids and derivatives thereof, their pharmaceutical use and preparation
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004772A2

  公开（公告）日：1979-10-17

  4-Halo-etianic acids and derivations of the formula: wherein X1 is fluoro or chloro; X2 is fluoro, chloro or hydrogen; X3 is fluoro, chloro, bromo or hydrogen; X4 is =C=O or of may be when X3 is chloro; R is hydrogen, alkyl of one to six carbon atoms optionally substituted with one halo, or phenyl or benzyl optionally substituted on the phenyl ring with a substituent selected from alkyl of one to four carbon atoms, alkoxy of one to four atoms and halo; R' is hydrogen or alkanoyl of 2 to 6 carbon atoms; R2 is hydrogen, a-methyl or β-methyl; and the solid and broken lines between C-1 and C-2 represent a double or a single bond. The compounds wherein R is other than hydrogen are useful as anti-inflammatory agents. They can be prepared by esterifying the corresponding acid. The 17a-esters can be prepared by esterifying the corresponding 17a-hydroxy compounds. The 17β-carboxylic group can be introduced by oxidising the corresponding 20-oxo-21-hydroxy (or alkanoyloxy) compound. The double bond at the 4,5 position is produced by contacting the corresponding Δ5 compound with a base.

  4-Halo-etianic acids 及其衍生物式： 其中 X1 是氟或氯 X2 是氟、氯或氢 X3 是氟、氯、溴或氢； X4 是 =C=O 或 的可以是 当 X3 为氯时； R 是氢、1 至 6 个碳原子的烷基，可选择被 1 个卤素取代，或苯基或苄基， 在苯基环上可选择被选自 1 至 4 个碳原子的烷基、1 至 4 个原子的烷氧基和卤素的取代基取代； R' 是氢或 2 至 6 个碳原子的烷酰基； R2 是氢、a-甲基或 β-甲基；以及 C-1 和 C-2 之间的实线和断线代表双键或单键。其中 R 为氢以外的化合物可用作抗炎剂。它们可以通过酯化相应的酸来制备。17a-酯可通过酯化相应的 17a- 羟基化合物制备。17β-羧基可以通过氧化相应的 20-氧代-21-羟基（或烷酰氧基）化合物来引入。4,5 位的双键是通过相应的 Δ5 化合物与碱接触产生的。
• 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。
• 4-Halo-pregn-4-enes, their preparation and pharmaceutical use
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0004766A2

  公开（公告）日：1979-10-17

  4-Halo-pregn-4-enee of the formula: wherein X' is fluoro or chloro; X2 is hydrogen, fluoro or chloro; X3 is hydrogen, fluoro, chloro or bromo; X4 is =C=O or or may be when X3 is chloro; R' is hydrogen, fluoro, chloro, bromo, hydroxy or methoxy; R2 is fluoro, chloro, hydroxy or alkanoyloxy of 2 to 6 carbon atoms when R' is hydrogen or R2 is the same as R1 when R' is fluoro, chloro, hydroxy or methoxy; R3 is hydroxy or alkanoyloxy of 2 to 6 carbon atoms when R4 is a-methyl or β-methyl or R3 and R4 together are and the solid and broken lines between the 1- and 2-positions in the A ring of the steroid nucleus represents a single or a double bond; have topical anti-inflammatory activity in mammals. They can be prepared by contacting the corresponding A5 compound with a base. The 17a-alkanoyloxy compound can be prepared by esterifying the corresponding 17a-hydroxy compound.

  式中的 4-卤代-4-孕烯： 其中 X'是氟或氯 X2 是氢、氟或氯 X3 是氢、氟、氯或溴； X4 是 =C=O 或 或可以是 当 X3 为氯时； R' 是氢、氟、氯、溴、羟基或甲氧基； R2 是氟代、氯代、羟基或 2 至 6 个碳原子的烷酰氧基。 当 R' 为氢或 R2 与 R1 相同时，R2 为氟、氯、羟基或 2 至 6 个碳原子的烷酰氧基 当 R' 为氟、氯、羟基或甲氧基时； 当 R4 为 a-甲基或 β-甲基时，R3 为羟基或 2 至 6 个碳原子的烷酰氧基，或 R3 和 R4 合在一起为 和 类固醇核 A 环上 1 位和 2 位之间的实线和断线代表单键或双键；对哺乳动物具有局部抗炎活性。它们可以通过将相应的 A5 化合物与碱接触来制备。17a-alkanoyloxy 化合物可通过酯化相应的 17a-hydroxy 化合物制备。