- A variation of Mattox rearrangement mechanism under alkaline condition
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A variation of the Mattox rearrangement, a key degradation pathway under acidic conditions for corticosteroids possessing the 1,3-dihydroxyacetone side chain, has been found to occur for the 17,21-diesters of these corticosteroids but under the alkaline condition. The mechanism of this variation of the original Mattox rearrangement is proposed.
- Li, Min,Chen, Bin,Lin, Mingxiang,Chan, Tze-Ming,Fu, Xiaoyong,Rustum, Abu
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Read Online
- Method for recycling betamethasone or dexamethasone synthetic mother liquor materials
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The invention relates to a method for recycling betamethasone or dexamethasone synthetic mother liquor materials. The method comprises the following steps: extracting a compound shown as formula 1 from a mother liquor material; carrying out protection reaction of the 20th site hydroxyl group on the compound shown as formula 1 to obtain a compound shown as formula 2; carrying out a reduction reaction of the 21th site aldehyde group on the compound shown as formula 2 to obtain a compound shown as formula 3, and continuously carrying out oxidation reaction and hydrolysis reaction to obtain a compound shown as 4 which is betamethasone or dexamethasone. The above recycling method can convert the betamethasone or dexamethasone mother liquor material into betamethasone or dexamethasone with highmedicinal value and economic benefit, and huge economic benefit is achieved.
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- A 17, 21 - double-hydroxy steroid derivatives of synthetic method
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The invention relates to a method of preparing 17, 21-double-hydroxyl steroid derivatives by using 6, 9-substituted silyl steroid enol ether compound I as an initiator.
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- A novel route for the preparation of betamethasone from 9α-hydroxyandrost-4-ene-3,17-dione (9αOH-AD) by chemical synthesis and fermentation
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A novel and efficient synthesis of betamethasone has been developed from the readily available 9α-hydroxyandrost-4-ene-3,17-dione (9αOH-AD). The 16α-methyl was introduced stereoselectively with CH3Br and converted to the 16β-methyl, the 17-side chain was installed with 2-chlorovinyl ethyl ether in the place of the toxic KCN/HOAc, and a mild fermentation was employed for the 1,2-dehydrogenation, replacing the DDQ oxidation. By adjustments and improvements of the steps, this route produced betamethasone in 11 steps with a 22.9% overall yield, showing its potential for industrial application with relatively low toxicity and cost.
- Tang, Jie,Liu, Xirong,Zeng, Chunlin,Meng, Hao,Tian, Mi,Guo, Cancheng
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p. 266 - 270
(2017/06/19)
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- Ring opening and fluoridation method and device of steroidal epoxy compound
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The invention discloses a method of preparing a compound II, which is as shown as the following reaction formula as shown in the specification. A 9 alpha-fluorine-11 beta -hydroxyl steroidal compound II is prepared via epoxy compound ring opening and fluoridation of a steroidal epoxy compound I by taking hydrogen fluoride as a fluorination reagent in a solvent consisting of arene and water. In the formula, R is CH3, CH2OH or CH2OAc; R1 is OH; R2 is alpha-CH3 or beta-CH3; and R3 is F or H. A continuous reaction device as shown in Figure 1 can be used in the method.
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Paragraph 0038; 0039; 0041
(2017/07/22)
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- Synthesis of betamethasone from the waste of Thai Agave sisalana
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Synthesis of betamethasone from waste of Thai A. sisalana is described. Copyright Taylor & Francis Group, LLC.
- Kongkathip, Ngampong,Kongkathip, Boonsong,Noimai, Naratitt
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p. 865 - 874
(2007/10/03)
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- Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
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- Composition for the topical treatment of poison ivy and other forms of contact dermatitis
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Composition for topical administration comprising (a) a corticosteroid, and (b) a drying agent.
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- Mucosal adhesive device for long-acting delivery of pharmaceutical combinations in oral cavity
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Mucosal adhesive devices are provided for use in the oral cavity for therapy against infections. The devices are dosage units which comprise a combination of antimicrobial agents such as antifungal agents and anti-inflammatory agents, optionally also a local anesthetic. The dosage units yield a gradual and relatively constant release of the pharmaceuticals over at least a 12-hour period.
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- High molecular weight prodrug derivatives of antiinflammatory drugs
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Compounds of the formula 1, PS - O - A - (CH2)n- B - D (1), wherein PS-O represents an alkoxide residue of any of the free hydroxy groups of a polysaccharide (PS-OH) compound with molecular weight (Mw) of from 40,000 to 5,000,000 selected from dextran, carboxymethyl dextran, diethylaminoethyl dextran, starch, hydroxyet-hyl starch, alginates, glycogen, pullullan, agarose, cellulose, chitosan, chitin and carrageenan,A is a carbonyl group or absent,n is zero or a positive integer from 1 to 14,B is oxygen, a carbonyl group, NR wherein R is hydrogen or lower alkyl, or B is absent, and, D is (i) a group of the formula:, R1 - CO - (11), wherein R1-CO- represents the acyl residue of a carboxylic acid drug (R1-COOH) used in the treatment of inflammatory disorders; or (ii) a group of the formula:, R2 - O - (12), wherein R2-O- refers to the C-21 alkoxide residue of a known antiinflammatory steroid (R2-OH) or an alkoxide residue of any other drug or medicament containing a hydroxy functional group used in the treatment of inflammatory disorders; with the proviso that when A is absent, n is 0, and B is absent, then R1-CO- is different from the acyl residue of acetylsalicylic acid;, and non-toxic pharmaceutically acceptable acid addition salts thereof;, and non-toxic pharmaceutically acceptable cation salts thereof. Such compounds are biolabile prodrugs providing controlled release and prolonged duration of action of the parent active antiinflamma-tory agents locally at the administration site after intra-articular, intra-muscular, subcutaneous or extra-dural application while at the same time being highly stable in aqueous solution in the pH range 3--5. After oral administration of such prodrugs the parent drug is liberated selectively in the terminal ileum and the colon over an extended period of time.
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- Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid
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This invention discloses an improved process for the production of corticoids from 17α-hydroxy steroids utilizing peroxymonosulfate.
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- Amine containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1
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- Amine containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1
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- Sulfonate containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1 and their salts.
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- Sulfonate containing ester prodrugs of corticosteroids
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Novel solution stable ester prodrugs of corticosteroids of the formula STR1 and their salts.
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- CORRELATION BETWEEN METABOLISM OF BETAMETHASONE 17,21-DIPROPIONATE AND ADRENAL HYPERTROPHY IN RAT FETUSES
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The effects of metabolites of betamethasone 17,21-dipropionate (BMDP) on the hypothalamo-pituitary-adrenocortical axis were assessed by measurements of adrenal weights, after studying the metabolism of BMDP in vivo and in vitro in pregnant rats and mice.After BMDP was injected intravenously at a dose of 5mg/kg into rats and mice in late stages of pregnancy, it disappeared rapidly from the plasma and brain in both mothers and fetuses while betamethasone 17-propionate (BMP) was detected as the main metabolite followed by betamethasone (BM).In vitro studies demonstrated that BMDP was metabolized to BMP in maternal and fetal tissues (plasma, liver, brain and placenta) of both species.The subcutaneous administration of BMP to rats in the late stages of pregnancy induced adrenal hypertrophy in fetuses, though the adrenals of the mothers became atrophic.In the case of mice, both maternal and fetal adrenals became atrophic.Administration of BM produced adrenal atrophy in mothers and fetuses of both species.The subcutaneous administration of 6β-hydroxybetamethasone 17-propionate (6β-OH-BMP) to rat fetuses in utero produced adrenal hypertrophy and 6β-hydroxybetamethasone (6β-OH-BM) showed no effect.These data suggest that BMP is transferred across the placental barrier to produce marked adrenal hypertrophy in rat fetuses.
- Nakano, Masayuki,Nishiuchi, Masanori,Takeuchi, Masaharu,Yamada, Hideo
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p. 511 - 526
(2007/10/02)
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- Cytotoxic nucleoside-corticosteroid phosphodiesters
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Nucleotides of nucleosides or bases having known cytotoxic activity are reacted with steroids, preferably corticosteroids, to form corresponding cytotoxic nucleoside-corticosteroid phosphodiester analogues of the formula: STR1 wherein: steroid is the residue formed by removal of a hydroxyl hydrogen atom from a natural or synthetic adrenal corticosteroid containing the characteristic cyclopentanophenanthrene nucleus which is esterified to the phosphate moiety at the 21-position; sugar is a naturally occurring pentose or deoxypentose in the furanose form, preferably ribose, deoxyribose, lyxose, xylose or arabinose and especially ribose, deoxyribose or arabinose, which is esterified to the phosphate moiety at the 5'-position and covalently bonded to the heterocycle moiety at the 1'-position to form a nucleoside; and heterocycle is a purine, pyrimidine, hydrogenated pyrimidine, triazolopurine or similar nucleoside base. The conjugates exhibit an enhanced therapeutic index as compared to the parent nucleoside or base compounds, and are thus useful cytotoxic, antiviral and antineoplastic agents.
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