211 results about "Androstanes" patented technology

The present invention refers to steroid derivatives for use as medicaments. More specifically, the invention also relates to the use of a steroid derivative of 5-androstene-, 5-pregnenolone or corresponding saturated derivatives (androstane- or pregnane-) in the manufacture of a medicament for the treatment of a benign and/or malignant tumour, which medicament is capable of interrupting disturbances in Wnt-signaling, such as cell-cycle arrest in G1-phase, and/or providing an angiostatic effect. Examples of such steroid derivatives are -5-androstene-17-ol, androstane-17-ol-pregnane-17-ol or pregnane-17-ol derivatives. In a further aspect, the invention relates to a method of producing a medicament for the treatment of a benign and/or malignant tumour and/or an inflammatory condition comprising the steps of contacting 5-androstane-3β,17-diol or androstane-3β-diol, an enzyme and a sulfotransferase to provide 5-androstene-17-ol-3β-sulfate or corresponding andros tane derivative (17-AEDS or 17-AADS); and mixing the 17-AEDS or 17-AADS so produced with a suitable carrier; whereby a medicament which is capable of acting as a ligand to peroxisome proliferators-activated receptor-(PPAR) is produced.

A novel process for preparing (2β,3α,5α,16β,17β)-17-acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane, a known intermediate in the synthesis of the skeletal muscle relaxant rocuronium bromide, is disclosed.

The invention provides a bromide type muscle relaxant, which mainly comprises a method for synthesizing rocuronium bromide, vecuronium bromide, pancuronium bromide and pipecuronium bromide , and is mainly characterized by adopting a ketene as an acylating agent during the process of transforming 5Alpha-androstane -2-alkene-17-alkone to 17-acetoxyl group-5Alpha- androstane-2, and 16-diene, adopting a stress kettle as a reactor when realizing the step of ring-opening and condensation of the 2 Alpha and 3 Alpha-epoxy compound, and adding a solid catalyst and a desiccant in the last step of operation of rocuronium bromide to greatly improve the reaction yield and the quality of products. The technology provided by the invention can shorten the synthesis time of the bromide type muscle relaxant, simplify the operation steps, improve the quality of products and reduce the production cost.

The invention provides a method for preparing (3beta)-17-(3-pyridyl)-androstane-5,16-diene-3-alcohol acetate. According to the method, the traditional Grignard addition reaction is adopted, pyridine groups are introduced in the presence of a catalyst such as cerous chloride, the method is low in raw material cost, available in raw materials, economical, practical, environment-friendly, convenient and simple in post-treatment, the reaction process is easily and continuously operated, the product quality and yield can be improved, and industrial production is promoted.

The invention discloses a synthesis process of vecuronium bromide. The synthesis process comprises the following steps: generating epiandrosterone sulfonyl ester (III) by carrying out esterification reaction between epiandrosterone (II) and paratoluensulfonylchloride; generating 5Alpha-androst-2-alkene-17-ketone (IV) by carrying out elimination and dehydration reaction between the (III) and 2,6-lutidines; generating 17-acetoxyl-5Alpha-androstane-2,16-diene (V) by carrying out enolization and esterification reaction between the (IV) and isopropenyl acetate; generating (2Alpha, 3Alpha, 16Alpha,17Alpha)-diepoxy-17Beta-acetyl-5Alpha-androstane (VI) by epoxy reaction of the (V) under the effect of hydrogen peroxide; generating 2Beta, 16Beta-di(1-piperidyl)-5Alpha-androstane-3Alpha-hydroxyl-17-ketone (VII) by ring-opening and addition reaction of the (VI) under the effect of hexahydropyridine; generating 2Beta, 16Beta-di(1-piperidyl)-5Alpha-androstane-3Alpha,17Beta-diol (VIII) by the (VII)under the reduction of potassium borohydride; generating 2Beta, 16Beta-di(1-piperidyl)-3Alpha, 17Beta- acetoxyl-5Alpha-androstane (IX) by carrying out esterification reaction of the (VIII) under the acetylation of acetic anhydride; and generating vecuronium bromide (I) by carrying out quaternary ammonium salt reaction between the (IX) and bromomethane. The invention has the advantages of low cost,less pollution and high yield.

The invention discloses a synthesis method of finasteride, which comprises the following steps that: taking inexpensive luteosterone and the like as the raw materials to finally prepare finasteride through 6 steps of synthetic reaction, i.e. the synthesis of 3- carbonyl-4- androstene-17beta-carboxylic acid, the synthesis of N-tertiary-butyl-3- carbonyl-4- androstene-17beta-formamide, the synthesis of N-tertiary-butyl-5- carbonyl-17beta- carbamoyl-A-lost carbon-3,5-cracking- androstane-3-acid, the synthesis of N-tertiary-butyl-3-carbonyl-4- aza-5- androstene-17beta-formamide, the synthesis of N-tertiary-butyl-3- carbonyl-4- aza-5alpha- androstane-17beta- formamide, and the synthesis of finasteride. The synthesis process has the advantages of inexpensive and easily available raw materials and stable yield, is applicable to industrial production, and the product quality meets the pharmacopeia standards.

The invention relates to a preparation method for progestin. 4-androstenedione is used as a raw material. The preparation method comprises the following steps: A, etherate is synthetized, wherein the 4-androstenedione and triethyl orthoformate perform an acid catalyzed reaction in organic solvents of dichloromethane, low-carbon alcohol and the like to obtain the etherate 3-ethoxy-androstane-3, 5-diolefin-17-ketone; B, a nitro substance is synthetized, wherein the etherate in the organic solvents and nitroethane perform 17-bit addition under the catalysis of ethylenediamine to obtain the nitro substance 3-ethoxy-20-nitro-pregnane-3, 5, 17 (20)-triene; and C, the progestin is synthetized, wherein the nitro substance is reduced by zinc powder in organic solvents of acetic acids, low-carbon alcohol and the like, acid hydrolysis is performed, so that semi-finished products of the progestin are obtained, the semi-finished products of the progestin are decolored and refined by alcohol and activated carbon to obtain the progestin, the content of HPLC is more than 99.5%, the melting point is 128-131 DEG C, and the total yield of synthetized weight is 83-87%. When the method disclosed by the invention is used for producing the progestin, the yield is high, the degree of purity is good, the quality is stable, the solvent recovering rate is high, and the method is economic and environment-friendly.

The invention provides a method for synthesizing difluprednate from a sterol fermentation product. The sterol fermentation product, namely 9 Alpha-hydroxyl-androstane-1,4-diene-3,17-diketone (9 Alpha-OH-AD) obtained by fermenting phytosterol of which the content in byproducts of the grease industry is very high, serves as a starting raw material. The method comprises the following 15 reaction steps in total: dehydrating steride 9-hydroxyl to form a double-bond; adding 17-carbonyl with acetylene; dehydrating; producing 21-copper carbonyl under an acid condition; epoxidizing 16,17-double bond; oxidizing periodide and introducing 21-hydroxyl; performing ring opening on 16,17 Alpha-epoxy hydrobromate; hydrogenating for removing 16 Beta bromine; forming a ring on orthoester; performing ring opening; esterifying; epoxidizing 9,11-double bond-Beta; enolizing and esterifying; performing ring opening on 6-electrophilic fluoro; and performing ring opening on 9,11-epoxy fluoro. According to the method, steride 17 Alpha and 21-dyhydroxyl are efficiently built by means of periodide oxidization, epoxide ring-opening and debromination and an important intermediate type 11 compound is obtained; in the whole process, a large quantity of heavy metal pollutant chromium which is generated when producing corticoid medicines in the traditional industry is effectively avoided, so that the method is green, environment-friendly and suitable to industrialized production.

A topical formulation of an androstane steroid compound of improved solubility in combinations of the solvents propylene glycol and propylene carbonate.

The invention discloses a preparation method of a compound 19-desmethyl-4-androstene-3,17 diketone, comprises the following step of by taking compounds of 5alpha-chloro-3beta-hydroxy-6beta and 19beta-epoxy-androstane-17-ketone as raw materials, and carrying out oxidation reaction on the compounds of 5alpha-chloro-3beta-hydroxy-6beta and 19beta-epoxy-androstane-17-ketone as well as an intermediate compound 19-hydroxy-4-androstene-3,17-diketone with N-halogenated amide oxidant in a mixed solution of an organic solvent and an alkaline buffer solution in the presence of a catalytic amount of 2,2,6,6-tetramethylpiperidine-N-oxide (TENPO) in the mild condition. In the two steps of oxidation reaction, the catalytic amount of 2,2,6,6-tetramethylpiperidine-N-oxide and the N-halogenated amide oxidant are both adopted to replace a mixed solution of chromium trioxide, sulfuric acid and water. In the oxidation method, without using the chromium trioxide, the use of carcinogenic substances are avoided being used, limitation by environmental protection is avoided and a great amount of wastes containing heavy metals in preparation are avoided being generated and accumulated, thereby no money and labor is consumed for removing the wastes.

The invention relates to a new method of stereo selectivity synthesis drospirenone and main intermediate in the synthesizing method; 15 Beta, 16 Beta-methylene dehydroepiandrosterone (3 Beta-hydroxy-15Beta, 16Beta-methylene -androstane -5-ene-17-ketone, 2) are adopted as starting raw material for the methods and the drospirenone is synthesized via fourteen steps. The invention has the advantages of higher yield and good stereo selectivity.

The invention pertains to the medicinal chemosynthesis field and relates to the preparation method of 1-square bracket 17Beta-acetoxyl-3Alpha-oxhydryl-2Beta-(4-morpholinyl)-androstane-16Beta-group square bracket-1-(2-propenyl) pyrrole bromide (rocuronium). The preparation method adopts 2Alpha, 3Alpha, 16Alpha, 17Alpha-diepoxy-5Alpha-androstane-17Beta-glycol acetate as the raw material from which the rocuronium is obtained after seven reaction steps including hydrolysis, pyrrole reaction, morpholinyl reaction, etherification, reduction, acetylation, hydrolysis and quaterisation. The preparation method of the invention has the advantages that the hydrolysis of 16Alpha, 17Alpha-epoxy-17Beta-acetoxyl takes place at a comparatively low temperature, which can avoid the ring opening of the epoxy and further the inhibition of the formation of 17Alpha-(1-pyrrolidine)-16-ketone; the synthesis avoids the optional acetylation of site 3 and site 17 oxhydryls and clearly simplifies the separation after reaction.

The invention relates to a high-purity (2 beta, 3 alpha, 5 alpha, 16 beta, 17 beta)-2-(4- morpholinyl)-16-(1-pyrrolidinyl)-androstane-3,17-diol or a composition thereof, a preparation method thereof (a compound shown in a formula III) or a composition thereof and application thereof to preparing rocuronium (a compound shown in a formula I). The method has good effect, low cost, high quality and simple and convenient operation and is suitable for large-scale industrial production; and the obtained product has high purity and stable properties.

The invention discloses a preparation method for a 3-carbonyl-4-aza-5alpha-androstane compound. The method comprises the following steps: 1, carrying out the hydrogenation action to a 3-carbonyl-4-aza-5 -androstane alkenyl compound, formic acid and a hydrogen donor agent for 5 to 24hours at 60 to 101 DEG C, then carrying out decompression and concentration to remove the formic acid, flushing the reactants into ice water for separating crystals, and obtaining a crude product after filtration and drying; and 2, adding the crude product into a recrystallization solution for recrystallization and obtaining the product. The hydrogen donor agent can be ammonium formate, potassium formate, sodium formate or triethylammonium formate. The preparation has the moderate reaction and low cost, and is suitable for the industrialized volume production.

A topical formulation including a solvent, an occlusive agent, a surfactant system, an androstane steroid compound of formula (I) wherein R<1 >represents a fluoro-, chloro- or bromo-methyl group or a 2'-fluoroethyl group, R<2 >represents a group COR<6 >where R<6 >is a C1-3 alkyl group or OR<2 >and R<3 >together form a 16alpha, 17alpha-isopropylidenedioxy group; R<3 >represents a hydrogen atom, a methyl group (which may be in either the alpha- or beta-configuration) or a methylene group; R<4 >represents a hydrogen, chlorine or fluorine atom; R<5 >represents a hydrogen or fluorine atom and the symbol --- represents a single or double bond, and the balance being water.

The invention provides a method for preparing androstane-1,4,6-triene-3,17-diketone. The method comprises the following steps: adding a compound (I) into a polar organic solvent, and adding an ester reagent and an acid catalyst into the mixture to preparing a compound (II); adding the compound (II) into the organic solvent, adding a halogen reagent and water into the mixture for halogenating reaction; after the reaction is completed, adding lithium salt for reaction to prepare a compound (III); and carrying out 1,2 position dehydrogenation of the compound (III) by a method for biofermentationby adopting an arthrobacter nicotinovorans to prepare the target product.

There are provided compounds of formula (I)

wherein

• R₁ represents O, S or NH;
• R₂ represents —C(═O)-aryl or —C(═O)-heteroaryl;
• R₃ represents hydrogen, methyl (which may be in either the α or β configuration) or methylene;
• R₄ and R₅ are the same or different and each represents hydrogen or halogen; and
• represents a single or a double bond;
• and salts and solvates thereof;
• process for preparing them, compositions containing them and their use in therapy.

This invention describes compounds of Structures 1, 2, and 3 and their use as allosteric modulators of the GABA receptor chloride ionophore complex to alleviate stress, anxiety, mood disorders, seizures, depression, treatment of drug and alcohol abuse, memory, premenstrual disorders, and neural system damage.

The invention discloses a preparation and detection method of an abiraterone acetate dimer compound, and relates to the of field pharmacy. The dimer compound is 3 beta-acetyl-16-(3 beta-acetyl androstane-5,16-diene-17-base)-17-(3-pyridyl) androsterone-5,16-diene. The method is as follows: adding compounds I and II into a reactor; dissolving the compounds and adding a palladium catalyst and alkali into the reactor; cooling to room temperature; filtering; concentrating; adding water; extracting; concentrating to obtain a compound III crude product; placing the crude product in the reactor; adding pyridine and an acetyl compound; stirring at room temperature till complete reaction; concentrating to remove pyridine and the acetyl compound; adding water, extracting and concentrating to obtain a dimer compound crude; and dissolving the dimer compound crude, washing, drying, filtering, concentrating and recrystallizing to obtain the abiraterone acetate dimer compound. According to high performance liquid chromatography detection and calculation by an area normalization method, the prepared dimer compound has a purity up to 98% and a yield higher than 80%.