Homotropanes with central nervous system activity
View Patent ↗Disclosed are novel homotropane compounds with CNS activity. These compounds can be used for alleviating symptoms of CNS disorders.
1. A compound having the following structure:
or its enantiomer or racemic mixtures thereof,
wherein the compound is selected from the group of a compound wherein R1, R2 and R4 and R6 are hydrogen, R3 is 2-naphthyl, R5 is —COEt, and R7 is methyl; a compound wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-i-PrPh, R5 is —COEt, and R7 is methyl; a compound wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-ClPh, R5 is —COEt, and R7 is methyl; a compound wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-(C 6 H 4 )CH═CH 2 , R5 is —COEt, and R7 is methyl; a compound wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-(C 6 H 4 )C(Me)=CH 2 , R5 is —COEt, and R7 is methyl; a compound wherein R1 is hydrogen, R2 is methyl, R4 and R6 are hydrogen, R3 is p-tolyl, R5 is —COEt, and R7 is methyl; a compound wherein R1 is hydrogen, R2 is phenyl, R4 and R6 are hydrogen, R3 is p-tolyl, R5 is —COEt, and R7 is methyl; a compound wherein R1, R2 and R7 are methyl, R3 is p-tolyl, R4 and R6 are hydrogen, and R5 is —COEt; a compound wherein R1 and R7 are methyl, R2 is phenyl, R3 is p-tolyl, R4 is hydrogen, R5 is —COEt, and R6 is hydrogen; a compound wherein R1, R2, R4 and R5 are hydrogen, R3 is 2-naphthyl, R6 is —COEt, and R7 is methyl; and, a compound wherein R1, R2, R4, R6 and R7 are hydrogen, R3 is p-tolyl, and R5 is —COEt.
2. A compound as in claim 1 , wherein R1, R2 and R4 and R6 are hydrogen, R3 is 2-naphthyl, R5 is —COEt, and R7 is methyl.
3. A compound as in claim 1 , wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-i-PrPh, R5 is —COEt, and R7 is methyl.
4. A compound as in claim 1 , wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-ClPh, R5 is —COEt, and R7 is methyl.
5. A compound as in claim 1 , wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-(C 6 H 4 )CH═CH 2 , R5 is —COEt, and R7 is methyl.
6. A compound as in claim 1 , wherein R1, R2, R4 and R6 are hydrogen, R3 is 4-(C6H4)C(Me)=CH 2 , R5 is —COEt, and R7 is methyl.
7. A compound as in claim 1 , wherein R1 is hydrogen, R2 is methyl, R4 and R6 are hydrogen, R3 is p-tolyl, R5 is —COEt, R7 is methyl.
8. A compound as in claim 1 , wherein R1 is hydrogen, R2 is phenyl, R4 and R6 are hydrogen, R3 is p-tolyl, R5 is —COEt, R7 is methyl.
9. A compound as in claim 1 , wherein R1, R2 and R7 are methyl, R3 is p-tolyl, R4 and R6 are hydrogen, R5 is —COEt.
10. A compound as in claim 1 , wherein R1 and R7 are methyl, R2 is phenyl, R3 is p-tolyl, R4 is hydrogen, R5 is —COEt, R6 is hydrogen.
11. A compound as in claim 1 , wherein R1, R2, R4 and R5 are hydrogen, R3 is 2-naphthyl, R6 is —COEt, R7 is methyl.
12. A compound as in claim 1 , wherein R1, R2, R4, R6 and R7 are hydrogen, R3 is p-tolyl, R5 is —COEt.
13. A compound having the following structure:
or its enantiomer or racemic mixtures thereof,
wherein R1, R2, R3, R6 and R7 are hydrogen, R4 is 4-(C 6 H 4 )C(Me)=CH 2 , R5 is —COEt.
14. A compound having the following structure:
or its enantiomer or racemic mixtures thereof, where Ar is a substituted or unsubstituted phenyl group, wherein the ring substituents, if present, are present as mono-, di- or tri-substitutions comprised of substituents selected from the group consisting of alkyl, alkenyl, alkoxy, halo, nitro, cyano, keto, amino, carboxylate or a combination thereof.
15. A compound as in claim 14 , wherein Ar is selected from the group consisting of p-tolyl, 2-naphthyl, 4-i-PrPh, 4-ClPh, 4-(C 6 H 4 )CH═CH 2 , or 4-(C 6 H 4 )C(Me)=CH 2 .
16. A compound having the following structure:
or its enantiomer or racemic mixtures thereof, where Ar is selected from the group consisting of 2-naphthyl, 4-i-PrPh, 4-ClPh, 4-(C 6 H 4 )CH═CH 2 , or 4-(C 6 H 4 )C(Me)=CH 2 .