Patent GB-1081588-A (GB)
Title: Diaryl-benzocycloalkanes
IPC: C07C37/055
Filed: 1965-10-04
Abstract: <FORM:1081588/C2/1> <FORM:1081588/C2/2> <FORM:1081588/C2/3> <FORM:1081588/C2/4> <FORM:1081588/C2/5> <FORM:1081588/C2/6> The invention comprises compounds of the Formulae I and III wherein Ph1 represents a 1,2-phenylene radical, -(CnH2n- 2)- and -(Cn-H2n- 4) wherein the letter n represents an integer from 3 to 7, represent alkylene and alkenylene radicals respectively forming together with two adjacent carbon atoms of Ph1 a fiveto seven-membered ring, two carbon atoms of said ring, one of which is adjacent to the 1,2-phenylene radical Ph1, carrying the groups Ar and -Ph2-O-Alk-X, Ph2 represents a phenylene radical, Alk represents an aliphatic radical having up to 7 carbon atoms, X represents a free or functionally converted carboxyl group and Ar represents an aryl radical or a heterocyclic radical of aromatic characteristics and salts of said compounds having a salt-forming group. A compound of the Formula I or III may be prepared by converting, in a compound of the Formula II or IV, respectively, in which Ph0 represents a phenyl radical substituted by at least one substituent Y capable of being converted into the group -O-Alk-X, such a substituent Y into said group; a compound of the Formula I may be prepared by reducing a compound of the Formula III and a compound of the Formula III may be prepared by eliminating the compound Z-H from a compound of the Formula VI where Z represents a hydroxyl group or an esterified hydroxyl group and in a resulting compound converting a free carboxyl group into a functionally converted derivative thereof or vice versa, converting a functionally converted carboxyl group into another functionally converted carboxyl group or converting a free carboxyl group into a salt thereof, in a resulting compound having an acid addition salt-forming group converting said compound into an acid addition salt thereof and in any resulting compound separating mixtures of isomers into their components.  Benzocycloalkanes of the Formula II may be prepared by reducing compounds of the Formula IV or by reacting a compound of the Formula V or a reactive ester thereof with a compound of the formula H-Ph0.  2 - (4 - Chlorophenyl) - 1,2,3,4 - tetrahydronaphthalen - 1 - ol and 2 - (4 - chlorophenyl) - 1 - benzosuberanol may be prepared by reacting 4-chlorophenylacetonitrile with 2-phenylethyl bromide and 3-phenyl-1-chloropropane to give 2 - (4 - chlorophenyl) - 4 - phenylbutyronitrile and a  - (4 - chlorophenyl) - 8 - phenylvaleronitrile, respectively, which on hydrolysis give the corresponding carboxylic acids, cyclizing the latter to give 2-(4-chlorophenyl)-1,2,3,4-tetrahydronaphthalen - 1 - one and 2 - (4 - chlorophenyl) - 1 - benzosuberanone respectively and reducing with sodium borohydride.  7 - Chloro - 2 - phenyl - 1,2,3,4 - tetrahydronaphthalen-1-ol may be prepared by reduction of the corresponding 1-oxo compound.  1 - (4 - Hydroxyphenyl) - 2 - phenyl - 1,2,3,4 - tetrahydronaphthalene may be prepared by reacting 2 - phenyl - 1,2,3,4 - tetrahydronaphthalen-1-one with 4-methoxyphenylmagnesium bromide, reducing the resulting 1-(4-methoxyphenyl) - 2 - phenyl - 3,4 - dihydronaphthalene to give the corresponding 1,2,3,4-tetrahydro-derivative and hydrolysing the latter.  Therapeutic compositions with hypocholesterolemic and liver-protecting properties in forms suitable for enteral or parenteral application comprise compounds of the Formulae I and II and physiologically tolerable salts thereof and a suitable carrier.