Polycyclic aromatic compounds

Claim 2

A compound of the formula (I): or a monomethyl or monoethyl ether thereof, the compound of formula (I) including its ethers containing not more than 28 carbon atoms in total, or an ester of salt thereof; wherein Ar is selected from the group comprising: optionally substituted by one or two substituents which taken together contain not more than four carbon atoms in total and which are the same or different and are selected from halo; cyano; C 1-3 alkyl or C 1-3 alkoxy each optionally substituted by hydroxy or C 1-2 alkoxy; halo substituted C 1-2 alkyl or C 1-2 alkoxy; a group S(O) n R 5 wherein n is an integer 0,1 or 2 and R is C 1-2 alkyl optionally substituted by hydroxy or C 1-2 alkoxy; or Ar is optionally substituted by a group NR 6 R 7 containing not more than 5 carbon atoms wherein R 6 and R 7 are the same or different and each is a C 1-3 alkyl group or NR 6 R 7 forms a five or six membered heterocyclic ring optionally containing one or two additional hetero atoms; R 1 is C 1-3 alkyl substituted by hydroxy; R 2 is hydrogen, C 1-3 alkyl or hydroxymethyl; R 3 and R 4 are the same or different and each is hydrogen, methyl or ethyl; R 1 , R 2 , R 3 and R 4 taken together containing not more than five carbon atoms; or the group: wherein -C-C- is a five or six membered saturated carbocyclic ring containing two or three hydroxy groups; R 8 is hydrogen, methyl or hydroxymethyl; R 9 and R 10 are the same or different and each is hydrogen or methyl; R 11 is hydrogen, hydroxy, methyl or hydroxymethyl; R 8 , R 9 , R 10 , R 11 and the -C-C- ring taken together containing less than seven carbon atoms.

Claim 3

A compound according to claim 1 wherein Ar is 6-chrysenyl, 7-fluoranthenyl or substituted 1- or 9- anthracenyl.

Claim 4

A compound according to either claim 1 or 2 wherein Ar is substituted by C l-2 alkyl or C l-2 alkoxyl each optionally substituted by chloro, hydroxy or methoxy; or a group S(O) n R 5 or chloro, imidazolyl, morpholino, cyano or bromo. Preferred substitutents are chloro, 2-chloroethyl or OCH 2 CH 2 R 12 wherein R 12 is hydrogen, hydroxy or methoxy or a group S(O) n CH 3 wherein n is the integer 0, 1 or 2.

Claim 5

A compound according to any one of claims 1 to 3 in which wherein R 13 is CH 2 OH, CH(CH 3 )OH or CH 2 CH 2 OH; R 14 is hydrogen, C 1-3 alkyl, or CH 2 OH; R 15 is hydrogen or methyl.

Claim 6

A compound according to any one of claims 1 to 4 in which wherein R 15 is hydrogen or methyl and R 16 is hydrogen, methyl or ethyl.

Claim 7

A compound of the formula (I) according to claim 1 selected from the group comprising: 2-((6-Chrysenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((9-Anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((1-Anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-Chloro-9-anthracenylmethyl)-amino)-2-methyl-1,3-propanediol, 2-((10-Bromo-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-Methyl-2-((10-methyl-9-anthracenylmethyl)amino)-1,3-propanediol, 2-Methyl-2-((10-methylthio-9-anthracenylmethyl)amino)-1,3-propanediol, 2-((10-(2-Chloroethyl)-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-Hydroxymethyl)-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 10-((1,1-Bis)hydroxymethyl)ethylamino)methyl-9-anthracene-carbonitrile, 2-Methyl-2-((10-methylsulfinyl-9-anthracenylmethyl)amino)-1,3-propanediol, 2-((10-Methoxy-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-Bromo-1-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((4,10-Dichloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanedioi, 2-((4,5-Dichloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((2,10-Dichloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((3,10-Dichloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((3-Fluoranthrylmethyl)amino)-2-methyl-1,3-propanediol, 2-Methyl-2-((2-triphenylenylmethyl)amino)-1,3-propanediol, 2-((4-Chloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((2-Chloro-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-Ethylthio-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-(2-Hydroxyethylthio)-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-Chloro-9-anthracenylmethyl)amino)-2-hydroxymethyl-1,3-propanediol, 2-((7-Fluoranthenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((10-(Z-Hydroxyethyloxy)-9-anthracenylmethyl)amino-2-methyl-1,3-propanediol, 2-((10-Ethoxy-9-anthracenylmethyl)amino)-2-methyl-1,3-propanediol, 2-((6-Chrysenylmethyl)amino)-2-hydroxymethyl-1,3-propanediol, 2-((6-Chrysenylmethyl)amino)-2-ethyl-1,3-propanediol, 2-Hydroxymethyl-2-((3-fluoranthenylmethyl)amino)-1,3-propanediol, 2-Ethyl-2-((3-fluoranthenylmethyl)amino-1,3-propanediol, Z-((10-chloro-9-anthracenylmethyl)amino)-Z-ethyl-1,3-propanediol 2-((3-chloro-9-anthracenylmethyl)amino-2-methyl-1,3-propanediol, (+-) (2R * , 3S*)-2-((6-chrysenylmethyl)amino)-2-methyl-1,3-butanediol, 2-((2-ethyl-9-anthracenlyrnethyl)amino)-2-methyl-1,3-propanediol and Z-((3-ethyl-9-anthracenlymethyl)amino)-2-methyl-1,3-propanediol, (+-)(2R*, 3S*)-2-((9-anthracenylmethyl)amino)-2-methyl-1,3-butanediol, (+-)(2R*, 3R * )-2-(((6-chrysenyl)methyl)amino)-2-methyl-1,3-butanediol, 2-(((6-chrysenyl)methyl)amino)-2-ethoxymethyl-1,3-propanediol, 3-methoxy-2-(((6-chrysenyl)methyl)amino)-2-methyl-1-propanol, 3-methoxy-2(((3-fluoranthenyl)methyl)amino)-2-methyl-1-propanol, (+-)(2R*, 2S*)-2-(((3-fluoranthenyl)methyl)amino)-2-methyl-1,3-butanediol, 2-ethoxymethyl-2-(((3-fluoranthenyl)methyl)amino)-1,3-propanediol, 2-(((9-anthracenyl)methyl)amino)-2-ethoxymethyl-1,3-propanediol, 2-β-((6-chrysenylmethyl)amino)-1-α,3-α-cyclohexanediol 2-β-((3-fluoranthenylmethyl)amino)-1-α,3-α-cyclohexanediol 2-((6-chrysenylmethyl)amino)-2-isopropyl-1,3-propanediol 2-((3-fluoranthrenylmethyl)amino)-2-isopropyl-1,3-propanediol 2-((6-chrysenylmethyl)ammo)-2-methyl-1,4-butanediol 2-((3-fluoranthenylmethyl)amino)-2-methyl-1,4-butanediol 2-(((10-chloro-I-anthracenyl)methyl)amino)-3-methyl-2,5-pentanediol 2-(((10-chloro-1-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol Meso-3-((6-chrysenylmethyl)amino)-2,4-pentanediol 2-((6-chrysenylmethyl)amino) - 1,3-propanediol 2-(((12-ethyl-6-chrysenyl)methyl)amino)-2-methyl-1,3-propanediol 2-(((10-(2-methoxyethoxy)-9-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol 2-methyl-2-(((10-morpholino-9-anthracenyl)methyl)amino)-1,3-propanediol 2-((9-anthracenylmethyi)amino)-3-methoxy-2-methyl-1-propanol 2-(((12-chloro-6-chrysenyl)methyl)amino)-2-methyl-1,3-propanediol 2-((9-anthracenylmethyl)amino)-2-isopropyl-1,3-propanediol 2-((9-anthracenylmethyl)amino)-2-methyl-1,4-butanediol 2-(((10-(1H-imidazol-1-yl)-9-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol 2-(4-ethyl-3-fluoranthenyl)methyl)amino)-2-methyl-,3-propanediol 2-(((12-ethoxy-6-chrysenyl)methyl)amino)-2-methyl-1,3-propanediol (la, 2β, 3a)-2-(9-anthracenylmethyl)amino-l,3-cyclohexanediol 2-(((4-chloro-10-hydroxyethoxy)-9-anthracenyl)methyl)amino)-2-methyl-1,3-propanediol (+-)(2R + ,/RS + , 4R + )-3-(6-chrysenylmethyl)amino)-3-methyl-2,5-pentanediol, 2-methyl-2-(((10-methylsulphonyl-1-9-anthracenyl)methyl)amino)-1,3-propanediol and salts and esters thereof.

Claim 8

2-((6-chrysenylmethyl)amino)2--2-methyl-1,3-propanediol or a salt or ester thereof.

Claim 9

2-((6-chrysenylmethyl)amino)2--2-methyl-1,3-propanediol or a salt or ester thereof.

Claim 10

Hydrochloride, methanesulfonate, ethanesulfonate, lactate, citrate or isethionate salt of a compound of the formula (I) according to any of claims 1 to 8.

Claim 11

A pharmaceutical formulation comprising a compound of the formula (I) or an ether, ester or salt thereof according to any one of claims 1 to 8together with a pharmaceutically acceptable carrier therefor.

Claim 12

A pharmaceutical composition according to claim 11, that comprises a sterile aqueous solution of a pharmaceutically and pharmacologically acceptable acid addition salt of a compound of the formula (I) according to any one of claims 1 to 6, that is isotonic with the blood of the recipient.

Claim 15

A novel chemical intermediate utilised in a process according to claims 1 to 9 herein. A method for the preparation of a compound of the formula (I) according to any one of claims 1 to 7, which comprises: (i) the reduction of a compound of formula (II): wherein R 1 to R 4 are as hereinbefore defined, or an appropriately protected derivative thereof, followed by deprotection where appropriate; (ii) the reduction of a compound of the formula (V): wherein R to R 4 are as hereinbefore defined and the hydroxy groups are optionally protected, followed by deprotection of the hydroxy groups where appropriate, or (iii) the reaction of a compound Ar CH 2 L, wherein Ar is as hereinbefore defined and L is a leaving group, with a compound of the formula (IV): wherein R to R 4 are as hereinbefore defined.

Claim 16

.4. A novel chemical intermediate of the formula (II), (IV), (V) as hereinbefore defined or of the formula ArCH 2 CHO wherein Ar is as hereinbefore defined.

Claim 17

.4. A novel chemical intermediate of the formula (II), (IV), (V) as hereinbefore defined or of the formula ArCH 2 CHO wherein Ar is as hereinbefore defined.