Method, composition and compounds for treating excess prostaglandins

A novel secondary phosphoric acid ester compound having the general formula ##STR25## wherein M is selected from the group consisting of hydrogen;

• and a pharmaceutically acceptable inorganic and organic cations;
• and wherein A is ##STR26## wherein one and only one of the substituents R.sup.6, R.sup.7, and R.sup.13 always represents a group R, located in any of the ortho, meta and para positions relative to the phosphoric acid ester group, the group R having the formula ##STR27## wherein X is selected from the group consisting of:
• ##STR28## ##STR29## wherein q is selected from the group consisting of zero and one;
• and wherein Z is selected from the group consisting of:
• straight saturated hydrocarbon chains having at most 3 carbon atoms;
• and straight hydrocarbon chains having 2 and 3 carbon atoms and containing one double bond;
• Z above may be substituted by one substituent selected from the group consisting of:
• lower alkyl;
• lower alkenyl;
• cyclopentyl;
• cyclohexyl;
• phenyl;
• phenyl substituted in m- or p-position by one substituent selected from the group consisting of lower alkyl, lower alkoxy, --F, --Cl, --Br, and --CF.sub.3 ;
• benzyl;
• benzyl substituted in m- or p-position by one substituent selected from the group consisting of lower alkyl, lower alkoxy, --F, --Cl, --Br, and --CF.sub.3 ;
• benzylidene;
• benzylidene substituted in m- or p-position by one substituent selected from the group consisting of lower alkyl, lower alkoxy, --F, --Cl, --Br, and --CF.sub.3 ;
• wherein B in the general formula (I) above is selected from the group consisting of:
• alkyl;
• having one to eight carbon atoms, inclusive, being at most di-substituted;
• cycloalkyl, namely cyclopentyl and cyclohexyl, being at most di-substituted;
• 1- and 2-naphthyl, both naphthyls being at most di-substituted;
• 2-, 3- and 4-biphenylyl, any biphenylyl being at most di-substituted;
• and ##STR30## wherein the substituents in B, when B is alkyl, having one to eight carbon atoms, inclusive;
• cycloalkyl;
• naphthyl;
• or biphenylyl, are selected from the group consisting of lower alkyl, lower alkoxy, --F, --Cl, --Br, and --CF.sub.3 ;
• wherein R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.10 , R.sup.11, R.sup.12, and R.sup.13 above are selected from the group consisting of:
• hydrogen;
• lower alkyl;
• lower alkenyl;
• lower alkoxy;
• hydroxy;
• --O--CO--R.sup.14 ;
• --F;
• --Cl;
• --Br;
• --CF.sub.3 ;
• --CO--R.sup.14 ;
• --CONR.sub.2.sup.8 ;
• --CH.sub.2 CONR.sub.2.sup.8 ;
• --OCH.sub.2 CONR.sub.2.sup.8 ;
• --NR.sup.8 --CO--R.sup.14 ;
• and --CH.sub.2 NR.sup.8 --CO--R.sup.14 ;
• where R.sup.8 is selected from the group consisting of hydrogen and lower alkyl;
• and where R.sup.14 is lower alkyl, with the proviso that one of the substituents R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.13 and one of the substituents R.sup.10, R.sup.11, and R.sup.12 is selected from the group consisting of --CONR.sub.2.sup.8 ;
• --CH.sub.2 CONR.sub.2.sup.8 ;
• --OCH.sub.2 CONR.sub.2.sup.8 ;
• --NR.sup.8 --CO--R.sup.14 ;
• and --CH.sub.2 NR.sup.8 --CO--R.sup.14 ;
• R.sup.8, and R.sup.14 having the meaning given above;
• at least one of the substituents R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.13, R.sup.10, R.sup.11, and R.sup.12 being selected from the said latter group.