79-61-8

Usage

Originator

Diloderm ,Schering,US,1960

Uses

antipruretic

Manufacturing Process

A solution of 1.0 g of 1,4,9(11)-pregnatriene-17α,21-diol-3,20-dione-21- acetate and 5.0 g of lithium chloride in 40 ml of glacial acetic acid is treatedwith 0.410 g of N-chlorosuccinimide, followed by 0.104 g of anhydrous hydrogen chloride dissolved in 2.5 ml of tetrahydrofuran. The reaction mixture is stirred for 2 hours and poured into ice water. The crude product is filtered and washed with water to give 1.12 g of solid material, which is recrystallized from acetone-hexane to give substantially pure 9α,11β-dichloro-1,4- pregnadiene-17α,21-diol-3,20-dione-21-acetate; MP 246°C to 253°C (dec.).

Brand name

Diloderm (Schering).

Therapeutic Function

Antipruritic, Antihistaminic, Appetite stimulant

InChI:InChI=1/C23H28Cl2O5/c1-13(26)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(27)6-8-20(14,2)23(17,25)18(24)11-21(16,22)3/h6,8,10,16-18,29H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20-,21-,22-,23-/m0/s1

Upstream product

• 128-09-6 N-chloro-succinimide 
• 4380-55-6 pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate 
• 84871-33-0 21-acetoxy-9α,11β-dichloro-17α-hydroxy-3-methyliminopregna-1,4-dien-20-one N-oxide 
• 84871-38-5 21-acetoxy-9α,11β-dichloro-17α-hydroxy-20-oxopregna-1,4-diene-3-thione 
• 13913-97-8 9α,11β-Dichlor-17α-hydroxy-21-acetoxy-pregnen-(4)-dion-(3,20) 

Downstream Products

• 7008-26-6 Dichlorisone 

Relevant academic research and scientific papers

Preparation and Reactions of Steroidal Croos-conjugated 3-Nitrones

Treatment of the N-methylnitrone (1b) of dichlorisone acetate (E-Z-mixture) with toluene-p-sulphonyl chloride in pyridine in the presence of water gave dichlorisone acetate (1a) (88percent).In the presence of hydrogen sulphide, however, the nitrone was deoxygenated to give the corresponding imine (1c), which on prolonged reaction with hydrogen sulphide in pyridine afforded the corresponding 1,4-diene-3-thione (1d).Similarly prepared were the unstable imines (2d), (3c), and (4c), which were smoothly converted into the corresponding thiones (2e), (3d), and (4d), respectively.In the absence of strong nucleophiles, dichlorisone acetate nitrone (1b) was treated with toluene-p-sulphonyl chloride in pyridine to give the corresponding trienimine (1g) (45percent).Under similar conditions, however, prednisolone-21-propionate nitrone (3b) gave the 2-p-tolylsulphonyloxy-derivative (3e) as the major product.Separate treatment of both Z- and E-isomers of dehydrotestesterone acetate nitrone afforded, in both cases, the 2-p-tolylsulphonyloxy-derivative (2g) (25percent), whereas betamethasone nitrone (4b) gave a mixture of the 2-p-sulphonyloxy-dienimine (4f) and the trienimine (4h) in low yield.