N-acyl derivatives of the LL-E33288 antitumor antibiotics, composition and methods for using the same
AssigneeAmerican Cyanamid Company
InventorMay D. M. Lee
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Abstract
The invention is N-acyl and dihydro-N-acyl analogs of the family of antibacterial and antitumor agents known collectively as the E33288 complex.
Claims18
A compound of the formula ##STR6## wherein R is hydrogen or a branched or unbranched alkyl (C.sub.1 -C.sub.10) optionally substituted by one or more hydroxy, or carboxy;
- R.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH(CH.sub.3).sub.2 ;
- W is ##STR7## wherein R.sub.1 is H or ##STR8## R.sub.4 is OH when R.sub.5 is H or R.sub.4 and R.sub.5 taken together are a carbonyl;
- and X is an iodine or bromine atom.
A process for producing a compound of the formula:
- ##STR21## wherein W is ##STR22## R.sub.1 is H or ##STR23## R.sub.4 is OH when R.sub.5 is H and x is an iodine or bromine atom comprising reacting ##STR24## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR25## wherein W is ##STR26## R.sub.1 is H or ##STR27## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR28## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR29## wherein W is ##STR30## R.sub.1 is H or ##STR31## R.sub.4 is OH or when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR32## wherein w is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR33## wherein W is ##STR34## R.sub.1 is H or ##STR35## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR36## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR37## wherein W is ##STR38## R.sub.1 is H or ##STR39## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR40## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula ##STR41## wherein W is ##STR42## R.sub.1 is H or ##STR43## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR44## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR45## wherein W is ##STR46## R.sub.1 is H or ##STR47## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR48## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR49## wherein W is ##STR50## R.sub.1 is H or ##STR51## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR52## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. from 5 minutes to 5 hours.
A process for producing a compound of the formula:
- ##STR53## wherein W is ##STR54## R.sub.1 is H or ##STR55## R.sub.4 is OH when R.sub.5 is H and X is an iodine or bromine atom comprising reacting ##STR56## wherein W is as defined above except R.sub.4 and R.sub.5 are taken together to form a ketone with sodium borohydride in an alcoholic solution at -5.degree. C. to about +5.degree. C. from 5 minutes to 5 hours.
A method of treating bacterial infections in warm-blooded animals which comprises administering to said animals an antibacterially effective amount of a compound of the formula:
- ##STR57## wherein W is ##STR58## R is hydrogen or a branched or unbranched alkyl (C.sub.1 -C.sub.10) optionally substituted by one or more hydroxy, or carboxy;
- R.sub.1 is H or ##STR59## R.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH(CH.sub.3).sub.2 ;
- R.sub.4 is OH when R.sub.5 is H or R.sub.4 and R.sub.5 taken together are a carbonyl;
- and X is an iodine or bromine atom.
A method of testing the growth of tumors in warm-blooded animals which comprises administering to said animals an oncolytic amount of a compound of the formula:
- ##STR60## wherein W is ##STR61## R is hydrogen or a branched or unbranched alkyl (C.sub.1 -C.sub.10) optionally substituted by one or more hydroxy, or carboxy;
- R.sub.1 is H or ##STR62## R.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH(CH.sub.3).sub.2 ;
- R.sub.4 is OH when R.sub.5 is H or R.sub.4 and R.sub.5 taken together are a carbonyl;
- and X is an iodine or bromine atom.
Dependencies are inferred from the claim text.