Novel compounds, compositions containing such compounds, processes for their preparation and methods of treatment
AssigneeAktiebolaget Leo
InventorsBertil Hogberg, Hans Fex, Torsten Perklev, Sten Veige, Bo Fredholm
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Abstract
This invention relates to novel secondary phosphoric acid esters and salts thereof, having valuable pharmacological properties, and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds, and methods of treatment therewith. The esters are i.a. useful as selective inhibitors of prostaglandins and of Slow Reacting Substances (SRS). They also inhibit the formation of adenosine 3',5'-monophosphate (cyclic AMP). In addition the esters of this invention also exert intrinsic smooth muscle stimulatory activity.
Claims20
A novel secondary phosphoric acid ester compound having the general formula ##STR24## wherein M is selected from the group consisting of hydrogen and a pharmaceutically acceptable inorganic and organic cation, and wherein A and B, independent of each other, are ##STR25## 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 ##STR26## wherein q is selected from the group consisting of zero and one, and wherein X is selected from the group consisting of:
- straight saturated hydrocarbon chains having at most 4 carbon atoms;
- and straight hydrocarbon chains having 2 to 4 carbon atoms and containing one double bond;
- wherein X above may be substituted by at most two substituents selected from the group consisting of;
- lower alkyl;
- cyclopentyl, cyclohexyl;
- phenyl;
- phenyl substituted in m- or p- position by one substituent selected from the group consisting of lower alkyl, --F, --Cl, and --Br;
- benzyl;
- and benzyl substituted in m- or p-position by one substituent selected from the group consisting of lower alkyl, --F, --Cl, and --Br, with the proviso that not more than one substituent selected from the group consisting of:
- cyclopentyl;
- cyclohexyl;
- phenyl;
- substituted phenyl;
- benzyl;
- and substituted benzyl is present in X;
- wherein B in the general formula (I) above also may be selected from the group consisting of:
- 1- and 2- naphthyl, both naphthyls being at most di-substituted;
- and ##STR27## wherein the substituents in B, when B is naphthyl, are selected from the group consisting of lower alkyl, -F, -Cl, and -Br;
- 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;
- --F;
- -Cl;
- and -Br;
- with the proviso that when B = A, resulting in symmetric secondary phosphoric acid esters, and q is zero, at least two of R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.13 are substituents other than hydrogen.
Dependencies are inferred from the claim text.