14-de(hydroxymethyl)-mycaminosyltylonolide derivatives

Details 14-de(hydroxymethyl)-mycaminosyltylonolide derivatives 14-de(hydroxymethyl)-mycaminosyltylonolide derivatives

1984-11-30

1986-04-01

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C07H 1708

Patent

active

045799407

ABSTRACT:
A compound of the formula ##STR1## wherein R.sub.1 is hydrogen, --COOR.sub.11 or ##STR2## R.sub.11 is optionally substituted lower alkyl, R.sub.12 is optionally substituted hydrocarbon, heterocyclic or heterocyclic-lower alkyl, R.sub.13 is hydrogen or lower alkyl, or R.sub.12 and R.sub.13 together constitute a heterocyclic ring together with the attached nitrogen atom, and R.sub.2 is hydrogen or hydroxyl, or a pharmaceutically-acceptable salt thereof, has stronger antibacterial activity against Gram-positive bacteria than does tylosin. It is produced by deformylation, or by oxidizing a formyl at position-14, or by amidating the latter compound.

REFERENCES:
patent: 4463171 (1984-07-01), Umezawa et al.
patent: 4490524 (1984-12-01), Fujiwara et al.
Migrdichian Organic Synthesis pp. 332, 311 and 257, 1957.
Morrison et al. Organic Chemistry 3rd ed. p. 631, 1973.
"Synthesis of 4'-Deoxymycaminosyl Tylonolide" The Journal of Antibiotics, Oct. 1981, pp. 1374-1376.
"The Structure of Tylosin.sup.1,2 ", Tetrahedron Letters, No. 54, 1970, Pergamon Press, Great Britain, pp. 4737-4741.

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