Conjugate compounds containing aza-macro-cycles and processes for their preparation

A compound selected from the group consisting of (i) a conjugate of a polypeptide bound to a group of the formula:

• ##STR14## in which the polypeptide is bound to said group through L.sup.1 and each of alk.sup.1, alk.sup.2, alk.sup.3, and alk.sup.4, independently of the other, is alkylene of 1 to 4 carbon atoms, unsubstituted or substituted with alkyl of 1 to 6 carbon atoms;
• each of R.sup.1, R.sup.2, and R.sup.3, independently of the other, is hydrogen or --alk--R.sup.5 ;
• alk is straight or branched alkylene of 1 to 6 carbon atoms;
• R.sup.5 is hydrogen, ##STR15## L is selected from the group consisting of a linking group L.sup.1, alkyl of from 1 to 10 carbon atoms, alkenyl of from 2 to 10 carbon atoms, alkynyl of from 2 to 10 carbon atoms, alkoxy of from 1 to 10 carbon atoms, alkylthio of from 1 to 10 carbon atoms, cycloalkyl of from 3 to 8 carbon atoms, cycloalkenyl of from 4 to 8 carbon atoms, aryl of from 6 to 12 carbon atoms, aralkyl of from 6 to 12 aryl and 1 to 6 alkyl carbon atoms, heteroaryl of from 4 to 10 carbon atoms and heteroaralkyl of from 4 to 10 heteroaryl and 1 to 6 alkyl carbon atoms;
• said alkyl, alkenyl, alkynyl, alkoxy or alkylthio group being uninterrupted or interrupted with one or more members selected from the group consisting of --O--, --S-- and --N(R.sup.9)--;
• said alkyl, alkoxy, aryl, aralkyl, heteroaryl or heteroaralkyl group being unsubstituted or substituted with one or more members selected from the group consisting of halo, hydroxy, alkyl of from 1 to 6 carbon atoms, alkoxy of from 1 to 6 carbon atoms, alkylthio of from 1 to 6 carbon atoms, --NR.sup.10 R.sup.11, nitro, cyano, carboxyl, --CONR.sup.12 R.sup.13, --SO.sub.2 NR.sup.12 R.sup.13 and cycloalkyl of from 3 to 8 carbon atoms;
• each of X.sup.1 and X.sup.2, independently of the other, is oxygen or sulfur;
• L.sup.1 is a linking group selected from the group consisting of alkylene of from 1 to 10 carbon atoms, alkenylene of from 2 to 10 carbon atoms, and alkynylene of from 2 to 10 carbon atoms which alkylene, alkenylene, or alkynylene is uninterrupted or interrupted with one or more members selected from the group consisting of --O--, --S--, --N(R.sup.9)--, --CON(R.sup.9)--, or --N(R.sup.9)CO--, a cycloalkane ring of 3 to 8 carbon atoms, an aromatic ring of 6 to 12 carbon atoms, or a pyridine, furane, or thiophene ring,
• said linking group being unsubstituted or substituted with one or more members selected from the group consisting of halo, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, hydroxy, nitro ##STR16## each of R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.12, independently of the other, is hydrogen or alkyl of 1 to 6 carbon atoms;
• each of R.sup.11 and R.sup.13, independently of the other, is alkyl of 1 to 6 carbon atoms;
• and
• d has a value of from 0 to 4;
• (ii) a complex of said conjugate with a di- or tripositive metal;
• and
• (iii) a salt of said conjugate or said complex.