- Methylprednisolone intermediate debrominated product and preparation method thereof
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The invention discloses a methylprednisolone intermediate debrominated product and a preparation method thereof. According to the preparation method, a compound shown as a formula I is used as a raw material, and a dechlorination reaction, a bromination reaction, a debromination reaction and an oxidation reaction are sequentially performed to prepare a compound (debrominated substance) shown as aformula V. The preparation method has the advantages of short synthetic route, high yield, low cost and easily available raw materials, is suitable for industrial production, and has very high industrial value.
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Paragraph 0034; 0039; 0040; 0045
(2020/02/10)
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- Pregnane-4-ene-17alpha-ol-3,11,20-trione preparation method
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The invention relates to a pregnane-4-ene-17alpha-ol-3,11,20-trione preparation method, which comprises: using a compound I as a raw material, adding a bromination reagent, and carrying out a 9,11-site bromo-hydroxyl reaction to obtain a compound II; mixing the compound II and an oxidizing agent, and carrying out an oxidation reaction, wherein the hydroxyl at the 11th position in the compound II is oxidized into a ketone group to obtain a compound III; and carrying out a reduction dehalogenation reaction on the compound III to obtain pregnane-4-ene-17alpha-ol-3,11,20-trione, wherein the structural formulas of the compound I, the compound II and the compound III are represented by the specification. According to the invention, the preparation method is short in synthetic route, high in product yield, low in cost and suitable for industrial production of pregnane-4-ene-17alpha-ol-3,11,20-trione.
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Paragraph 0081; 0087-0089; 0094-0096; 0102-0104; 0109; 0110
(2020/02/07)
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- New steroid 11-ketone group oxidation synthesizing process
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The invention discloses a new steroid 11-ketone group oxidation synthesizing process. The method comprises that in a nonprotic organic solvent, under conditions of dimethyl sulfoxide (DMSO) as an oxidant, an organic alkali, dichlorophenyl phosphate and a piperidine aminoxyl free radical, a steroid 11-alpha hydroxyl compound is subjected to an oxidation reaction to generate a steroid 11-ketone group compound, the reaction temperature is -10 DEG C to a solvent reflux temperature, and the piperidine aminoxyl free radical is selected from the group consisting of a 2,2,6,6-tetramethylpiperidine-1-oxyl free radical or an analogue thereof.
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Paragraph 0133; 0134; 0135
(2016/10/09)
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- Multi-hydroxy pregnane 11 α hydroxy selective oxidation method
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The invention provides a selective oxidation method for selective oxidation method for polyhydroxy-pregna-11alpha-hydroxy. According to the invention, pregna-4-ene-3,20-diketone-11alpha,17alpha-dihydroxy is used as a substrate and reacts with dimethyl sulfoxide and an activator in liquid chloroalkane, and alkali is added after completion of the reaction so as to adjust a pH value to 8.5 to 10, thereby obtaining pregna-4-ene-3,11,20-triketone-17alpha-hydroxy.
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Paragraph 0008; 0019; 0020
(2017/02/17)
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- REDUCTIVE DEHALOGENATION OF 21-IODO DERIVATIVES OF CORTICOSTEROIDS
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In the reactions of 21-iodo derivatives of corticosteroids with hydrogen sulfide and thiol-containing reagents in a medium of dipolar aprotic and amide protogenic solvents at room temperature reductive-deiodination reactions occur with the formation of 21-deoxycorticosteroids in quantitative yield.Reactions of solutions of 21-iodomethyl ketones, heated to 80 deg C, with hydrogen sulfide and thiol-containing reagents give not only reduction products, but also products of nucleophilic substitution at C21 in yields of 20-30percent.
- Mikhal'chuk, A. L.,Pschenichnyi, V. N.
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p. 1479 - 1485
(2007/10/02)
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- Synthesis of 3α,6β,17,20α-Tetrahydroxy-5β-pregnan-11-one 6-Hemisuccinate, a Hapten for Immunoassay of 3α,17,20α-Trihydroxy-5β-pregnan-11-one
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3α,6β,17,20α-Tetrahydroxy-5β-pregnan-11-one 6-hemisuccinate (4) has been synthesised by two distinct routes.In the first of these, introduction of a 6β-hydroxy substituent into 17α-hydroxypregn-4-ene-3,11,20-trione followed by catalytic hydrogenation of the Δ4-olefinic bond gave 6β,17α-dihydroxy-5β-pregnane-3,11,20-trione.The 5β-configuration was confirmed by an X-ray crystallographic analysis of the derived 6-hemisuccinate.Subsequent selective reduction at C-3 and C-20 by sodium borohydride in the presence of cerous chloride gave the required compound (4), although in low overall yield.To avoid the problem of non-specificity in the reduction at C-20, alternative routes were explored from precursors already possessing the essential 17,20α-diol system, protected as the isopropylidene derivative or by acetylation as appropriate.Hydroboration-oxidation of 3,3-ethylenedioxy-17,20α-isopropylidenedioxypregn-5-en-11-one gave the 6β-hydroxy derivative of 5β-configuration, verified by dehydration (POCl3-pyridine) to the 6-ene derivative.Further routine transformations including succinoylation of the 6β-hydroxy derivative, deprotection at C-3 and in the side chain, and reduction of the 3-oxo group, gave the required compound (4).
- Cooley, George,Kirk, David N.
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p. 1205 - 1212
(2007/10/02)
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