Detail of "57781-14-3"

Reference

Synthesis and topical antiinflammatory properties of 17,21-bis(acetyloxy)-6

Synthesis and topical antiinflammatory properties of 17,21-bis(acetyloxy)-6.beta.,9-difluoro-11.beta.Several substances are used for example 57781-12-1 and 60864-55-3 which are their cas registry numbers.-hydroxypregna-1,4-die ne-3,20-dione and related 2-halogenated compounds. Toscano, Luciano; Grisanti, Giampiero; Fioriello, Giuseppe; Barlotti, Luigi; Bianchetti, Alberto; Riva, Mario (Dep. Synth. Chem. Res., Pierrel S.p.A. Res. Lab., Milan, Italy). J. Med. Chem., 20(2), 213-20 (English) 1977. CODEN: JMCMAR. DOCUMENT TYPE: Journal CA Section: 2 (Hormone Pharmacology) Section cross-reference(s): 32 Introduction of a halogen atom at C-2 of steroid 3-ketofluorohydrins, obtained from corresponding 5.alpha.,6.alpha.-epoxides by trans-diaxial opening with hydrofluoric acid, prevents the 6.beta.-fluorine atom from undergoing rearrangement to the more stable 6.alpha. configuration when the 5-tert-hydroxyl is split off to yield a conjugated double bond. Two processes were investigated for the synthesis of 17,21-bis(acetyloxy)-6.beta.-fluoropregna-1,4,9(11)-triene-3,20-dione (I) [60864-38-2] and its 2-bromo analog [57808-78-3] starting from the known 21-(acetyloxy)-6.beta.-fluoro-5.alpha.,11.alpha.,17-trihydroxyprenane-3, 20-dione [57781-09-6]. Successive reaction with hypobromous acid, epoxidn., and fluorination converted I and its 2-bromo analog into 17,21-bis(acetyloxy)-6.beta.,9-difluoro-11.beta.-hydroxypregna-1,4-die ne-3,20-dione (II) [60864-46-2] and its 2-bromo analog [57781-14-3]. In addn., a synthesis of 17,21-bis(acetyloxy)-2-chloro-6.beta.,9-difluoro-11.beta.-hydroxypregna -1,4-diene-3,20-dione [59047-08-4] is described. The antiinflammatory activity of II and its 2-chloro and 2-bromo analogs was compared with the corresponding 6.alpha.,9-difluoro epimers. Some 6.beta.-fluoro compds. displayed high topical antiinflammatory activity without systemic effects. .

New esters of halopredone for topical antiinflammatory use

New esters of halopredone for topical antiinflammatory use. Toscano, L.; Grisanti, G.; Bianchetti, A.; Bossoni, G. (Chem. Dep., Pierrel S.p.A., Milan, Italy). Arzneim.-Forsch., 27(9), 1634-5 (English) 1977. CODEN: ARZNAD. DOCUMENT TYPE: Journal CA Section: 2 (Hormone Pharmacology) Section cross-reference(s): 32 Esters of halopredone (I) [57781-15-4] were synthesized and tested in rats, for local and systemic antiinflammatory activities. The greatest topical antiinflammatory activity was shown by the 17,21-diacetate [57781-14-3], 17-benzoate [57781-28-9], and 21-benzoate [57781-35-8], and the greatest systemic activity was shown by I itself and by the 17-acetate [57781-23-4] and 21-acetate [57781-32-5]. Esterification of I generally resulted in a shift from oral to topical activity, and the local antiinflammatory activities of short chain esters were lower than those of esters with longer C chains. The esters of I had little or no effect on thymus or body wt.