Patent GB-1406611-A (GB)
Title: Pharmaceutically active secondary phosphoric acid esters
IPC: C07C49/84
Filed: 1972-01-31
Abstract: 1406611 Medicines comprising phosphoric acid esters LEO AB 16 Aug 1972 [17 Aug 1971 (4) 31 Jan 1972 (4)] 38577/71 38578/71 38580/ 71 38579/71 4508/72 4509/72 4510/72 and 4511/ 72 Addition to 1398528 Heading A5B [Also in Division C2] A pharmaceutical composition comprises as active ingredient an ester of formula I where M is hydrogen or a pharmaceutically acceptable inorganic or organic cation, and where A and B, independently, are. where one of the substituents R<SP>6</SP> ,  R<SP>7</SP> and R<SP>13</SP> is a group R which has the formula where X is a covalent bond or a C 1-4  straight hydrocarbon chain which is saturated or contains one double bond and wherein X may be substituted by at most two substituents which are C 1-4  alkyl, C 2-4  alkenyl, oxo, optionally in the form of a ketal of a C 1-4  aliphatic alcohol; OH; C 1-4  alkoxy; -O-CO-R<SP>14</SP>; cyclopentyl; cyclohexyl: phenyl; benzyl; C 1-4  alkylidene; or or benzylidene; with the proviso that not more than one oxo group is present in X, that not more than one of the sulbstituents OH, C 1-4  alkoxy and -O-CO-R<SP>14</SP> is present in X; that not more than one of the substituents cyclopentyl; cyclohexyl; phenyl; benzyl; and benzylidene is present in X; and that the oxo substituent, if present, is always positioned at either end of X if X has more than 1 C atom, among the above substituents of X phenyl, benzyl and benzylidene being optionally substituted in M or P position with one substitutuent which is C 1-4  alkyl or alkoxy; F; Cl: Br or CF 3 ; and wherein B in the formula I may also be C 1-8  alkyl; cyclopentyl; cyclohexyl; 1- or 2-naphthyl; 2-, 3- or 4-biphenylyl; all of which are optionally mono- or disubstituted by C 1-4  alkyl or alkoxy, F, Cl, Br or CF 3 ; or wherein R<SP>3</SP>, R<SP>4</SP>, R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP>, R<SP>10</SP>, R<SP>11</SP>, R<SP>12</SP> and R<SP>13</SP>, except for the one being R, are H, C 1-4  alkyl or alkoxy, C 2-4  alkenyl, OH, OCOR<SP>14</SP>, OP(O)(OM) 2 , F, Cl, Br, CF 3 , CN, NO 2 , COOR<SP>9</SP>, CH 2 COOR<SP>9</SP>, OCH 2 COOR<SP>9</SP>, COR<SP>14</SP>, CONR<SP>8</SP> 2 , CH 2 CONR<SP>8</SP> 2 , OCH 2 CONR<SP>8</SP> 2 , NR<SP>8</SP> 2 , NR<SP>8</SP>COR<SP>14</SP>, CH 2 NR<SP>8</SP> 2  or CH 2 NR<SP>8</SP>COR<SP>14</SP>, where R<SP>8</SP> is H or C 1-4  alkyl; R<SP>9</SP> is C 1-4  alkyl or M and R<SP>14</SP> is C 1-4  alkyl; with the proviso that when B is equal to A and X is a covalent bond, at least 2 of R<SP>3</SP>, R<SP>4</SP>, (R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP> and R<SP>13</SP> are substituents other than H; and that when X of R in A has an oxo substituent and has more than 2 C atoms in the chain, then B is C 1-8  alkyl; cyclopentyl; cyclohexyl; 1- or 2-naphthyl; 2-, 3- or 4-biphenylyl; all of which are optionally mono- or disubstituted with C 1-4  alkyl or alkoxy, F, Cl, Br or CF 3 ; or a group of formula (iii) above. The composition may also contain other active ingredients such as natural or synthetic prostaglandins or analogues thereof, antiseptics, spasmolytics, analgesics, tranquillisers, steroids or hormones. The compounds of formula I and compositions containing them are used (a) to control excess formation and release of endogenous prostaglandins, (b) to counteract unfavourable effects of exogenous prostaglandins, (c) to control excess formation and release of slow reacting substance, (d) to control excess formation and release of cyclo AMP or (e) to produce a smooth muscle stimulatory effect in living non-human animal bodies.