RESUMO
Esters of levonorgestrel (13 beta-ethyl-17 alpha-ethynyl-17 beta-hydroxygon-4-en-3-one) with a variety of aliphatic and alicyclic carboxylic acids have been prepared and characterised. In tests for the suppression of estrus in rats, esters with short-chain aliphatic acids and with cyclobutane-carboxylic acid were considerably more active than the standard, norethisterone enanthate (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one). Such esters show great promise for development as long-acting progestogens.
Assuntos
Anticoncepcionais Orais Combinados/síntese química , Anticoncepcionais Orais/síntese química , Norgestrel/síntese química , Ácidos Carboxílicos , Preparações de Ação Retardada , Ésteres , Indicadores e Reagentes , Levanogestrel , Espectrofotometria , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
The synthesis of eighteen esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) is described. These all possess some form of alpha- and/or beta-substitution in the ester side-chain. The work was undertaken in order to evaluate any long-acting fertility control effect intrinsic in such compounds. A pentamethyl disiloxy ether was also included in the group of substances prepared for testing because of its similar substitution pattern.
Assuntos
Noretindrona/análogos & derivados , Ésteres , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Noretindrona/síntese química , Espectrofotometria , Relação Estrutura-AtividadeRESUMO
The chemical synthesis and physical data of several new esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) are reported, which contain either a chloro- or an alkoxy-group as a substituent in the acid side-chain.
Assuntos
Noretindrona/análogos & derivados , Ácidos Carboxílicos , Preparações de Ação Retardada , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Noretindrona/síntese química , Espectrofotometria Infravermelho , Relação Estrutura-AtividadeRESUMO
Several esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) with carboxylic acids containing a cyclopropyl or cyclobutyl ring have been synthesized and the stereochemistries of the side-chains determined.
Assuntos
Noretindrona/análogos & derivados , Preparações de Ação Retardada , Ésteres , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Noretindrona/síntese química , Espectrofotometria , Relação Estrutura-AtividadeRESUMO
The synthesis of esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxy-estr-4-en-3-one) with acids containing a benzene ring is described, two methods of esterification being compared in terms of yield and convenience. The activities of these esters as long-acting contraceptive agents have been evaluated.
