Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-09-16
1995-06-06
Ivy, C. Warren
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549510, 549511, A61K 31335, C07D30514
Patent
active
054223644
ABSTRACT:
Alkaline sensitive protaxol is water soluble and is hydrolyzed at physiological (alkaline) pH to render the native taxol structure and the native taxol activity. Protaxol compositions include 2'- and/or 7-O-ester derivatives of taxol and/or 2'- and/or 7-O-carbonate derivatives taxol. Protaxol has a formula as follows: ##STR1## wherein R.sup.1 and R.sup.2 are each H or a radical selected from the group consisting of --CO--(CH.sub.2).sub.m --X--(CH.sub.2).sub.n --COZ and --COO--(CH.sub.2).sub.o --Y--Ar, and wherein m, n, and o are each an integer of 1 to 3; X is O, S, NH, SO, or SO.sub.2 ; Y is S, SO or SO.sub.2 ; Ar is phenyl or substituted phenyl wherein the substituent is halo, amino, nitro or N,N-dialkylamino having 1 to 4 carbons in each of the alkyl groups; and Z is OH, OR.sup.3, SR.sup.3 or NR.sup.4 R.sup.5 wherein R.sup.3 is alkyl containing 1 to 4 carbons and R.sup.4 and R.sup.5 are each alkyl containing 1 to 4 carbons, or taken together with the nitrogen to which they are attached form a saturated heterocyclic ring having 4 or 5 carbons, with the proviso that at least on R.sup.1 and R.sup.2 is not hydrogen; as well as the salts of such compounds with organic/inorganic bases and acids, preferably pharmaceutically acceptable salts.
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Deutsch, et al., "Synthesis of Congeners and Prodrugs. 3. Water-Soluble Prodrug of Taxol with Potent Antitumor Activity", J. Med. Chem., 32: 788-792 (1989).
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Kerr Michael A.
Nicolaou K. C.
Riemer Claus G.
Ivy C. Warren
Lewis Donald G.
The Scripps Research Institute
Trinh Ba K.
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