NITROGEN BRIDGEHEAD COMPOUNDS AND PROCESS FOR THE PREPARATION THEREOF

摘要

Prepns. of the new cpds. of formula (I) are claimed. (R and R1 are each H or 1-4C alkyl or together on adjacent atoms are -CH=CH-CH=CH-. R2=H or 1-4C Alkyl. R3=H, 1-4C alkyl, phenyl, COOH (or its alkali metal salts), 2-5C alkoxycarbonyl, CONH2, CN, CONHCONR14SO2. C6H4CH3 or (CH2)1-3, COOR14. R14=H or 1-4C alkyl. n=0 or 1. (a) is R13=H, and R12=R11 and R9=R10 are together bonds, then Y is 0 or 5 and R7+R8 represent the lone electron pair (l.e.p.) of Y; or y=N, R7 = 1-4C alkyl, opt. substd. 6-10C aryl or 7-12C aralkyl, R8=l,e.p. or 1-4C alkyl (in which case a halide counter anion is present); X(R4R5R6) represents halo or X=0 or 5, R4=H or 1-4C alkyl, R5+R6=l.e.p., or X=N, R4=chloroacetyl, 1-4C alkyl, opt. substd. 6-10C aryl or opt. substd. heteroaryl, R5=H or alkyl and R6=l.e.p.; opr (b) R12+R13= bond, R11=H and R9+R10=bond; other definitions as in (a); or (c) when R10+R11 and R12+R13 each represent bonds then Y=0 or 5, R7, R8+R9=l.e.p. (with associated countercation), or R8+R9=l.e.p. and R7=H or 1-4C alkyl; or Y is N, R7= H, 1-4C alkyl, opt. substd. 6-10C aryl; R8=1-4C alkyl and R9=l.e.p.; X(R5R6R7) may be halo, or X = 0 or 5 and R4,R5,R6=l.e.p. with associated countercation) or R4=H or 1-4C alkyl and R5+R6=l.e.p. or X is N and R5,R6,R7 are as in (a) for X=N. When Y and X = 0 or 5; R5,R6,R7,R8 and R9 are l.e.p., or Y and X = N, R6 and R9 = l.e.p. and R5 and R8=H or 1-4C alkyl, then R4+R7 form together (CH2)s (s=1-4). The methods comprises reacting cpds. (II) with (a) iminium halides R15R16N=CX2A-; (b) CS2 and alkali metal (M); (c) isocyanates R17. N.CV. opt. followed by usual modifications, conversion to salts. resolution of racemates etc. R15 and R16=1-4C alkyl, R15 can also be 6-10 aryl. A is an anion, X= halo. R17=1-4C alkyl, chloroacetyl, opt. substd. 6-10C aryl or opt. substd. heteroaryl, V=0 or 5. Some of (I) are also intermediates e.g. by reaction with aryl diazonium salts for 9-hydrazono cpds. useful as antiallergic agents.