Process for the preparation of enantiomerically pure cycloalkano-indol -and azaindol -and pyrimido ›1,2a! indolcarboxcyclic acids and their activated derivatives

A process for preparing a compound of the formula (I):

• ##STR40## in which A represents a radical of the formula:
• ##STR41## in which J, D, E, G, L and M independently represent hydrogen, halogen, trifluoromethyl, carboxyl, hydroxyl, linear or branched alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, or linear or branched alkyl having up to 6 carbon atoms, which alkyl is optionally substituted by hydroxyl or by linear or branched alkoxy having up to 4 carbon atoms;
• R.sup.1 and R.sup.2, together with the carbon atoms to which they are attached, form a phenyl ring, a pyridyl ring or a ring of the formula:
• ##STR42## in which R.sup.5 represents hydrogen, or linear or branched alkyl having up to 4 carbon atoms;
• and
• wherein the ring formed by R.sup.1 and R.sup.2 together with the carbon atoms to which they are attached is optionally monosubstituted to trisubstituted by substituents independently selected from the group consisting of halogen, trifluoromethyl, carboxyl, hydroxyl, linear or branched alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, or linear or branched alkyl having up to 6 carbon atoms, which alkyl is optionally substituted by hydroxyl or by linear or branched alkoxy having up to 4 carbon atoms;
• R.sup.3 and R.sup.4, together with the carbon atoms to which they are attached, form a phenyl ring or a 4- to 8-membered cycloalkene or oxocycloalkene ring;
• wherein the ring formed by R.sup.3 and R.sup.4 together with the carbon atoms to which they are attached is optionally monosubstituted to trisubstituted by substituents independently selected from the group consisting of halogen, trifluoromethyl, carboxyl, hydroxyl, linear or branched alkoxy or alkoxycarbonyl each having up to 6 carbon atoms, or linear or branched alkyl having up to 6 carbon atoms, which alkyl is optionally substituted by hydroxyl or by linear or branched alkoxy having up to 4 carbon atoms;
• T represents cycloalkyl having 4 to 12 carbon atoms, or linear or branched alkyl having up to 12 carbon atoms;
• Q represents hydroxyl or an activating radical;
• or a salt of said compound;
• said process comprising:
• a) diastereoselectively alkylating a compound of the formula (II):
• ##STR43## in which R.sup.6, together with the oxygen atom to which it is attached, represents a chiral alcohol radical;
• by reaction of said compound of the formula (II) with a compound of the formula (III):
• T-Z (III)
• in which
• T has the meaning indicated above;
• and
• Z represents a leaving group;
• in an inert solvent and in the presence of a base to yield the enantiomerically pure compound of the formula (IV):
• ##STR44## in which T and R.sup.6 have the meanings indicated above;
• b) halogenating the compound of formula (IV) to yield the enantiomerically pure compound of formula (V):
• ##STR45## in which T and R.sup.6 have the meanings indicated above;
• and
• R.sup.7 represents halogen;
• c) reacting the compound of formula (V) with the compound of formula (VI):
• A-H (VI)
• in which
• A has the meaning indicated above;
• to yield the enantiomerically pure compound of formula (VII):
• ##STR46## in which A, T and R.sup.6 have the meanings indicated above;
• d) hydrolyzing the compound of formula (VII) to yield the compound of formula (I) wherein Q represents hydroxyl;
• and
• e) optionally reacting the compound of formula (I) wherein Q represents hydroxyl with an activating reagent to yield the compound of formula (I) wherein Q represents an activating radical.