2,3-Dialkoxy-1,4-quinone derivatives; method of producing 1,4-quinone derivatives

Abstract

Abstract A compound of the general formula: wherein m is an integer of 10 to 21; R 1 is lower alkyl having 1 to 4 carbon atoms; B is a -CH 2 - or-CO- group, when B is-CH2-, R 2 is hydrogen, lower alkyl having 1 to 4 carbon atoms or lower acyl having 1 to 8 carbon atoms, and when B is -CO-, R 2 is hydrogen or lower alkyl having 1 to 4 carbon atoms, has pharmaceutical activities such as hypotensive, tissue metabolism stimulating, immunoregulatory, lysosomal membrane stablizing and SRS-A production inhibitory activities and is useful as a heart failure remedy, cerebral circulation disturbance remedy, immunoregulatorand antiallergic drug. A compound of the general formula: [wherein each R 3 is lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, or two R 3 's taken together represent -CH =CH-CH =CH-; n is O or an integer of 1 to 20 and when n is 1 to 20, A is -CH 2 -, or -CO- and Z is CH 2 OH, acyloxymethyl having 2 to 11 carbon atoms, esterified or unesterified carboxyl having 1 to 5 carbon atoms, lower alkoxymethyl having 2 to 5 carbon atoms, silyloxymethyl having 4 to 7 carbon atoms or acetalmethyl having 3 to 8 carbon atoms; when n is O, -A(CH 2 ) n -Z is (wherein - is 0 or an integer of 1 to 12) and Z is H] can be produced with advantage for commercial-scale production by oxidising a compound of the general formula: [wherein X 1 or X 2 is hydroxyl or amino, with the other being H or an esterified hydroxyl group having 1 to 8 carbon atoms or etherified hydroxyl group having 2 to to 8 carbon atoms; the other symbols are as defined above] with oxygen or air in the presence of a transition metal complex compound.

Inventors

• 👤 Okutani Tetsuya
• 👤 Goto Giichi
• 👤 Imada Isuke
• 👤 Watanabe Masazumi

Bibliographic Details