Patent GB-1066613-A (GB)
Title: Naphthalene derivatives
Inventor: BOND PETER ANTHONY
IPC: C07D263/06
Filed: 1965-03-03
Abstract: Compounds of the general Formula (I) <FORM:1066613/C2/1> (wherein R1 stands for a hydrogen atom, an alkyl radical optionally substituted by one or more hydroxy, alkoxy or aryloxy radicals, a cycloalkyl radical or an aralkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms, and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents), their esters (other than those wherein the naphthalene nucleus bears a hydroxy radical) and the acid addition salts of the alcohols and esters are prepared by (a)-in the case of those alcohols wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals-reacting a compound of the formula <FORM:1066613/C2/2> (wherein A stands for the group <FORM:1066613/C2/3> or <FORM:1066613/C2/4> wherein X stands for a halogen atom, and wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with R1NH2 (when R1 stands for a hydrogen atom the ammonia may be replaced by phthalimide, the phthalic acid residue being subsequently removed), (b)-in the case of those alcohols wherein the naphthalene nucleus bears at least one hydroxy radical-reacting a compound of the Formula (I) wherein the naphthalene nucleus bears at least one alkoxy substituent and may optionally bear one or more alkyl substituents, or an acid addition salt thereof, with a dealkylating agent, (c)-in the case of those alcohols wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals -reacting a compound of the formula <FORM:1066613/C2/5> (wherein the naphthalene nucleus bears at least one substituent selected from alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with a compound of the formula <FORM:1066613/C2/6> or <FORM:1066613/C2/7> (d)-in the case of those alcohols wherein R1 stands for a radical of the formula -CHR3R4, wherein R3 stands for a hydrogen atom or an alkyl radical and R4 stands for an alkyl radical optionally substituted by one or more hydroxy, alkoxy or aryloxy radicals, or an aryl or aralkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms, or R3 and R4 are joined together with the adjacent carbon atom to form a cycloalkyl radical-reacting a compound (which may be generated in situ) of the formula <FORM:1066613/C2/8> (wherein the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) with R3COR4 under reducing conditions, (e)-in the case of those alcohols wherein R1 is as defined above except that it is not an a -aryl-alkyl radical optionally substituted by one or more alkoxy radicals or halogen atoms-hydrogenolysing a compound of the formula <FORM:1066613/C2/9> (wherein R5 stands for a hydrogenolysable radical and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) or an acid addition salt thereof, or (f)-in the case of the esters-acylating an acid addition salt of a corresponding alcohol (when the ester bears an acyloxy radical on the naphthalene nucleus, the term "corresponding alcohol" includes the alcohol wherein the naphthalene nucleus bears a hydroxy radical), optionally followed in each case by acid addition salt formation or conversion to the free base. Oxazolidine derivatives of the general formula <FORM:1066613/C2/10> (wherein R6 stands for a hydrogen atom or an alkyl radical and the naphthalene nucleus bears at least one substituent selected from hydroxy, alkoxy and acyloxy radicals and may optionally bear one or more alkyl substituents) and their acid addition salts are prepared by reacting a compound of the Formula (I) with R6CHO, optionally followed by acid addition salt formation.  The preparation of 1,2-epoxy-3-(4-methoxy-1-naphthoxy)propane, 1 - chloro - 3 - (6,7 - dimethoxy - 1 - naphthoxy) - 2 - propanol, 1 - (N - benzyl - N - isopropylamino) - 3 - (4 - methoxy - 1 - naphthoxy) - 2 - propanol hydrochloride, 1 - phthalimido - 3 - (4 - methoxy - 1 - naphthoxy) - 2 - propanol, 1,2 - epoxy - 3 - (5 - methoxy - 1 - naphthoxy) - propane, 1 - chloro - 3 - (6 - methoxy - 1 - naphthoxy) - 2 - propanol, 1 - (4 - acetoxy - 3 - methyl - 1 - naphthoxy) - 3 - chloro - 2 - propanol, 4 - acetoxy - 3 - methyl - 1 - naphthol and 1,2 - epoxy - 3 - (4 - isopropoxy - 1 - naphthoxy)propane is described.  Compounds (I), their esters and oxazolidine derivatives and the acid addition salts of the alcohols, esters and oxazolidine derivatives, are useful in the treatment or prophylaxis of heart diseases and in the treatment of hypertension, myocardial infraction and phaeochromocytoma. They may be administered in the form of pharmaceutical preparations containing them together with a diluent or carrier.