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Details for Patent: 4,767,790

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Details for Patent: 4,767,790

Title: Therapeutic agents
Abstract:Compounds of formula I ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, cycloalkylalkyl or optionally substituted phenyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, formyl, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring show therapeutic acitivity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.
Inventor(s): Jeffery; James E. (Nottingham, GB3), Kozlik; Antonin (Nottingham, GB3), Wilmshurst; Eric C. (Nottingham, GB3)
Assignee: The Boots Company plc (GB2)
Filing Date:Apr 19, 1985
Application Number:06/725,129
Claims:1. A compound of formula III ##STR34## or a pharmaceutically acceptable salt thereof in which R.sub.1 is methyl or ethyl, R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are each selected from the group consisting of H, methyl and ethyl, or R.sub.3 is a cycloalkyl group containing 3 to 6 carbon atoms and R.sub.4 is H, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a pyrrolidinyl ring, and R.sub.5 and R.sub.6 together with the phenyl ring to which they are attached form a 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 3-chlorophenyl, 3-bromophenyl, 3,4-dichlorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-3-trifluoromethylphenyl, 4-biphenylyl, 2-naphthyl or 2-phenanthryl group.

2. A compound according to claim 1 which is N-methyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 which is 1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 1 which is N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

5. A compound according to claim 1 which is N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

6. A compound according to claim 1 or a pharmaceutically acceptable salt thereof in which R.sub.1 is methyl; R.sub.2 is H; R.sub.3 is H, methyl or ethyl; R.sub.4 is H, methyl or ethyl; R.sub.5 is chloro; R.sub.6 is H or chloro.

7. A compound according to claim 6 which is 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

8. A compound according to claim 6 which is N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]-ethylamine or a pharmaceutically acceptable salt thereof.

9. A pharmaceutical composition useful for treating depression in humans which comprises an antidepressently effective amount of a compound of the formula III ##STR35## or a pharmaceutically acceptable salt thereof in which R.sub.1 is methyl or ethyl, R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are each selected from the group consisting of H, methyl and ethyl, or R.sub.3 is a cycloalkyl group containing 3 to 6 carbon atoms and R.sub.4 is H, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a pyrrolidinyl ring, and R.sub.5 and R.sub.6 together with the phenyl ring to which they are attached form a 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 3-chlorophenyl, 3-bromophenyl, 3,4-dichlorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-3-trifluoromethylphenyl, 4-biphenylyl, 2-naphthyl or 2-phenanthryl group, in combination with a pharmaceutically acceptable carrier.

10. A composition according to claim 9 in which N-methyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

11. A composition according to claim 9 which is 1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

12. A composition according to claim 9 which is N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

13. A composition according to claim 9 which is N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

14. A composition according to claim 9 wherein R.sub.1 is methyl, R.sub.2 is H, R.sub.3 is H, methyl or ethyl, R.sub.4 is H, methyl or ethyl, R.sub.5 is chloro and R.sub.6 is H or chloro.

15. A composition according to claim 14 wherein the compund is 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

16. A composition according to claim 14 wherein the compound is N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]-ethylamine or a pharmaceutically acceptable salt thereof.

17. A method of treating depression in humans which comprises administering to a human or animal in need thereof an antidepressently effective amount of a compound of the formula III ##STR36## or a pharmaceutically acceptaable salt thereof in which R.sub.1 is methyl or ethyl, R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are each selected from the group consisting of H, methyl and ethyl, or R.sub.3 is a cycloalkyl group containing 3 to 6 carbon atoms and R.sub.4 is H, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a pyrrolidinyl ring, and R.sub.5 and R.sub.6 together with the phenyl ring to which they are attached form a 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 3-chlorophenyl, 3-bromophenyl, 3,4-dichlorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-3-trifluoromethylphenyl, 4-biphenylyl, 2-naphthyl or 2-phenanthryl group, in combination with a pharmaceutically acceptable carrier.

18. A method according to claim 17 wherein R.sub.1 is methyl, R.sub.2 is H, R.sub.3 is H, methyl or ethyl, R.sub.4 is H, methyl or ethyl, R.sub.5 is chloro and R.sub.6 is H or chloro.

19. A method according to claim 17 in which N-methyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

20. A method according to claim 17 which is 1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

21. A method according to claim 17 which is N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

22. A method according to claim 17 which is N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.
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