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Details for Patent: 4,806,570

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Details for Patent: 4,806,570

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 activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.
Inventor(s): Jeffery; James E. (Nottingham, GB), Kozlik; Antonin (Nottingham, GB), Wilmhurst; Eric C. (Nottingham, GB)
Assignee: The Boots Company plc (GB2)
Filing Date:Dec 23, 1985
Application Number:06/812,730
Claims:1. A compound of the formula I: ##STR34## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different, are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different, are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring.

2. A compound of formula I according to claim 1 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, and R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluromethyl, methyl, methoxy and phenyl or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

3. A compound according to claim 1 of the formula III: ##STR35## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different, are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring.

4. A compound according to claim 3 in which R.sub.1 is propyl or butyl, R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, and R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy and phenyl or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

5. A compound according to claim 1 of the formula IV: ##STR36## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different, are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; R.sub.5 is H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms or phenyl and R.sub.6, is fluoro or methyl.

6. A compound according to claim 5 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, R.sub.5 is H, fluoro, chloro, bromo, iodo, trifluormethyl, methyl, methoxy or pheny; and R.sub.6 is fluoro or methyl.

7. A compound according to claim 1 of the formula III: ##STR37## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; 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.

8. A pharmaceutical composition useful for treating depression in humans which comprises an anti-depressantly effective amount of a compound of the formula I: ##STR38## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring, in combination with a phrmaceutically acceptable carrier.

9. A composition of formula I according to claim 8 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, and R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy and phenyl or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

10. A composition according to claim 8 of the formula III: ##STR39## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring.

11. A composition according to claim 10 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, and R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy and phenyl or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

12. A composition according to claim 8 of the formula IV: ##STR40## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups consisting 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; R.sub.5 is H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms or phenyl and R.sub.6, is fluoro or methyl.

13. A composition according to claim 12 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, R.sub.5 is H, fluoro, chloro, bromo, iodo, trifluormethyl, methyl, methoxy or pheny; and R.sub.6 is fluoro or methyl.

14. A composition according to claim 8 of the formula III: ##STR41## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; 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 method of treating depression in humans which comprises administering to a human in need thereof an anti-depressantly effective amount of a compound of the formula I: ##STR42## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring in combination with a pharmaceutically acceptable carrier.

16. A method of formula I according to claim 15 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy and phenyl or and R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

17. A method according to claim 15 of the formula III: ##STR43## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; and R.sub.5 and R.sub.6, which are the same or different are selected from the group consisting of H, halo, trifluormethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring optionally substituted by at least one halo, alkyl or alkoxy group containing 1 to 4 carbon atoms or the substituents of the second benzene ring together with the two carbon atoms to which they are attached form a further benzene ring.

18. A method according to claim 17 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, and R.sub.5 and R.sub.6, which are the same or different, are selected from the group consisting of H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms, and phenyl or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring optionally substituted by halo.

19. A method according to claim 15 of the formula IV: ##STR44## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; R.sub.2 is selected from the group consisting of H and alkyl groups containing 1 to 3 carbon atoms; in which R.sub.3 and R.sub.4, which are the same or different are selected from the group consisting of H, straight or branched chain alkyl groups containing 1 to 4 carbon atoms, alkenyl groups having 3 to 6 carbon atoms, alkynyl groups having 3 to 6 carbon atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO; R.sub.5 is H, halo, trifluoromethyl, alkyl groups containing 1 to 3 carbon atoms, alkoxy groups containing 1 to 3 carbon atoms, alkylthio groups containing 1 to 3 carbon atoms or phenyl and R.sub.6, is fluoro or methyl.

20. A method according to claim 19 in which R.sub.1 is propyl or butyl; R.sub.2 is H or methyl, R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl, R.sub.5 is H, fluoro, chloro, bromo, iodo, trifluormethyl, methyl, methoxy or pheny; and R.sub.6 is fluoro or methyl.

21. A method according to claim 15 of the formula III: ##STR45## or a pharmaceutically acceptable salt thereof in which R.sub.1 is propyl or butyl; 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.

22. A compound of claim 1 which is 1-[1-(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

23. A compound of claim 1 which is N,N-dimethyl-1-[1(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

24. A compound of claim 1 which is N-methyl-1-[1-(4-dichlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

25. A compound of claim 1 which is N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

26. A composition according to claim 8 wherein the compound is 1-[1-(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

27. A composition according to claim 8 wherein the compound is N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

28. A composition according to claim 8 wherein the compound is N-methyl-1-[1-(4-dichlorophenyl)cyclo-butyl]butylamine or a pharmaceutically acceptable salt thereof.

29. A composition according to claim 8 wherein the compound is N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.
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