ES403542A1 - Substituted phenylimidazolidinones the acid addition salts thereof and processes for their preparation - Google Patents

Abstract

Procedure for the preparation of compounds of the formula **(See formula)** wherein R is hydrogen, an alcohol or lower alkoxy group, or a halogen atom; R'means one of the groups, in the target positions or for -CHR1-Q-A, -CHR2-A and -O-CHR2-CHR1-Q-A, where A represents radicals **(See formula)** Q means a branched or unbranched alcoholic chain with 1 to 4 carbon atoms, R1 means the hydrogen atom, the hydroxy group, a lower alkoxy group or the group -Q-CO-R5, R2 means the hydrogen atom or the methyl group, R3 and R4, which may be the same or different, represent the hydrogen atom, an alcohol or lower alkoxy group, a halogen atom or the trifluoromethyl group, or together also a 5- or 6-membered ring, aliphatic or aromatic, adjacent condensed, R5 signifies a lower alcohol group, which may be substituted by halogen, hydroxy or alkoxy, the amino group or a monoalkoxylamino or dialcoylamino group, Z means an aromatic ring with 1 to 2 heteroatoms, with which it can also be adjacently fused a benzene ring, and in which R'' designates the hydrogen atom or an alcoholic, alkenyl, alkynyl, hydroxyalkoxy, dialkoylaminoalkoxy or lower aralkoxy radical, branched or unbranched, as well as the corresponding acid addition salts, characterized in that a) an amine of the formula is reacted H-A (II) with a compound of the formula **(See formula)** where Ra represents one of the groups, in the meta positions or for -CHR2-X, -CHR1-Q-X and -O-CHR2-CHR1-Q-X in which X means a radical capable of being separated with the hydrogen from the compound HA in the form of HX, in the presence of an HX fixing agent; or because b) for the preparation of the compounds according to the invention in which R1 signifies the hydrogen atom, the hydroxy group or a lower alkoxy group, a ring closure is carried out in a corresponding compound of the formula **(See formula)** or because c) for the preparation of the compounds of formula I, in which R'' does not represent a hydroxyalkyl radical, R1 does not represent the hydroxy group and R5 does not represent a hydroxyalkyl radical, the amino group or a monoalkoxy amino group, a ring closure is performed on ethylene diamine derivatives of the formula **(See formula)** with appropriate carbonic acid derivatives or with metal cyanates in the presence of acids; or because d) for the preparation of the compounds according to the invention in which A designates the radical **(See formula)** a compound of the formula is subjected to reductive amination **(See formula)** where Rb means one of the groups, in the target positions or for -CHO, -CHR1-CnH2n-1O and -O-CHR2-CHR1-CnH2n-1O (n equal to 1, 2, 3 or 4), with an amine of the formula HA; or because e) for the preparation of the compounds of the formula I, in which R'means the radical -CHOH-Q-A, ketones of the formula are reduced **(See formula)** or because f) for the preparation of the compounds of the formula I, in which it means hydrogen and R'' means a radical R''1, the OH group is removed from a compound of the formula **(See formula)** in which R''1 signifies an alcoholic, alkoxyalkoyl or lower aralkoyl radical and R0 represents one of the radicals, in the meta or para positions of the formula -CR2OH-A, -CHOH-Q-A or -O-CHR2-CHOH-Q-A or because, g) for the preparation of the compounds of the general formula I, in which R1 signifies the hydroxy group, a compound of the formula is reacted **(See formula)** where Rd means one of the radicals, in the meta or para positions, of the formulas **(See formula)** wherein R6 and R7 signify hydrogen or alcohol radicals having together up to 3 carbon atoms, with an amine of the formula H-A; or because h) for the preparation of the compounds of the formula I, in which R1 represents the hydrogen atom, a lower alkoxy group or the group -O-CO-R5, in which R5 is an alcoholic or alkoxyalcoyl group or a dialkoxylamino group, a compound of the formula is reacted **(See formula)** where R'has the preceding meanings, limited as regards R1, and Me + signifies an alkali metal cation, with a corresponding compound R''X; or why i) for the preparation of compounds of formula I, in which R'represents the radical -O-CHR2-CH2-Q-A a phenol of the formula is reacted **(See formula)** wherein the phenolic OH group is in the meta or para positions, with a compound of the formula X-CHR2-CH2-Q-A in the presence of an acid binding agent; or because k) for the preparation of compounds of the formula I, in which R1 signifies an alkoxy group or a group -O-CO-R5 and R'' does not signify the hydroxyalkyl group, a compound of the formula is reacted **(See formula)** where Re represents one of the radicals in meta positions or for -CHOH-Q-A or -O-CHR2-CHOH-Q-A with an agent to replace the hydrogen of the OH by means of an alcoholic group or with a group -CO-R5; and because eventually the bases, obtained primarily according to the process modes a) to k), are transformed into acid addition salts, the acid addition salts, obtained primarily in said procedures, are transformed into free bases, and/or eventually a doubling is carried out into diastereoisomers or optical antipodes. (Machine-translation by Google Translate, not legally binding)