Fluorenecarboxylic acid esters, process for the manufacture thereof, and use thereof as medicaments
View Patent ↗Fluorenecarboxylic acid esters of general formula 1 wherein X − and the groups A, R, R 1 , R 2 , R 3 , R 3′ , R 4 , and R 4′ have the meanings given in the claims and in the specification, processes for the manufacture thereof and the use thereof as medicaments.
1. A process for preparing a compound according to formula 1,
the process comprising in a first step:
reacting a compound of formula 2
with a compound of formula 3
wherein R′ denotes chlorine or a C 1 –C 4 -alkyloxy group,
to produce an intermediate compound of formula 4
and in a second step
reacting the intermediate compound of formula 4 with a compound of the formula R 2 —X,
wherein
A is a group selected from
R is methyl, ethyl, —CF 3 , or —CHF 2 ;
R 1 and R 2 , which are identical or different, are each C 1 –C 3 -alkyl;
R 3 , R 4 , R 3′ and R 4′ which may be identical or different denote hydrogen, —C 1 –C 4 -alkyl, —C 1 –C 4 -alkyloxy, hydroxy, —CF 3 , —CHF 2 , CN, NO 2 or halogen; and
X − is an anion with a single negative charge.
2. The process according to claim 1 , wherein X − is chloride, bromide, 4-toluenesulfonate, or methane-sulfonate, R is methyl, R 3 , R 4 , R 3′ and R 4′ are hydrogen, and R 1 and R 2 , which are identical or different, are each methyl or ethyl.
3. The process according to claim 1 , wherein X − is chloride, bromide, or methane-sulfonate, R is methyl, R 3 , R 4 , R 3′ and R 4′ are hydrogen, and R 1 and R 2 are methyl.
4. The process according to claim 1 , wherein X is bromide, R is methyl, R 3 , R 4 , R 3′ and R 4′ are hydrogen, and R 1 and R 2 , which are identical or different, are each methyl or ethyl.
5. A compound according to formula 1,
wherein
A is a group selected from
R is methyl, ethyl, —CF 3 , or —CHF 2 ;
R 1 and R 2 , which are identical or different, are each —C 1 –C 3 -alkyl;
R 3 , R 4 , R 3′ and R 4′ which may be identical or different denote hydrogen, —C 1 –C 4 -alkyl, —C 1 –C 4 -alkyloxy, hydroxy, —CF 3 , —CHF 2 , CN, NO 2 or halogen; and
X − is an anion with a single negative charge,
the compound produced by a process comprising:
in a first sten reacting a compound of formula 2
with a compound of formula 3
wherein R′ denotes chlorine or a C 1 –C 4 -alkyloxy group,
to produce an intermediate compound of formula 4
and in a second step reacting the intermediate compound of formula 4 with a compound of the formula R 2 —X to form a comnound of formula 1.
6. The compound according to claim 5 , wherein X − is chloride, bromide, 4-toluenesulfonate, or methane-sulfonate, R 3 , R 4 , R 3′ and R 4′ are hydrogen, R is methyl, and R 1 and R 2 , which are identical or different, are each methyl or ethyl.
7. The compound according to claim 5 , wherein X − is chloride, bromide, or methane-sulfonate, R 3 , R 4 , R 3′ and R 4′ are hydrogen, R is methyl, and R 1 and R 2 are methyl.
8. The compound according to claim 5 , wherein X − is bromide, R 3 , R 4, R 3′ and R 4′ are hydrogen, R is methyl, and R 1 and R 2 , which are identical or different, are each methyl or ethyl.