.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Details for Patent: 4,522,828

« Back to Dashboard

Details for Patent: 4,522,828

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, GB2), Kozlik; Antonin (Nottingham, GB2), Wilmshurst; Eric C. (Nottingham, GB2)
Assignee: The Boots Company plc (Nottingham, GB2)
Filing Date:Apr 05, 1982
Application Number:06/365,285
Claims:1. A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I ##STR36## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl group contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms and groups of formula II ##STR37## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which 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 ad 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 carbons atoms, cycloalkyl groups in which the ring contains 3 to 7 carbon atoms, and a group of formula CHO or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;

in which 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 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;

or a pharmaceutically acceptable salt thereof.

2. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 4 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylmethyl groups in which the cyclo alkyl ring contains 3 to 6 carbon atoms and groups of formula II in which R.sub.9 and R.sub.10 are selected from the group consisting of H, fluoro or methoxy and in which R.sub.2 is H or methyl.

3. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I in which R.sub.1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and phenyl.

4. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl.

5. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I in which R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring containing one nitrogen atom and 4 or 5 carbon atoms which is optionally substituted by one or more alkyl groups or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring containing a second nitrogen atom which is optionally alkylated or a heterocyclic ring including one or more double bonds.

6. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula I in which 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.

7. A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III ##STR38## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl groups contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms, and groups of formula II ##STR39## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which 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 or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;

in which 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 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;

or a pharmaceutically acceptable salt thereof.

8. A method of treating depression as claimed in claim 7 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 4 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylmethyl groups in which the cycloalkyl ring contains 3 to 6 carbon atoms and groups of formula II in which R.sub.9 and R.sub.10 are selected from the group consisting of H, fluoro or methoxy and in which R.sub.2 is H or methyl.

9. A method of treating depression as claimed in claim 7 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III in which R.sub.1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and phenyl.

10. A method of treating depression as claimed in claim 7 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl.

11. A method of treating depression as claimed in claim 7 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III in which R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring containing one nitrogen atom and 4 or 5 carbon atoms which is optionally substituted by one or more alkyl groups or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring containing a second nitrogen atom which is optionally alkylated or a heterocyclic ring including one or more double bonds.

12. A method of treating depression as claimed in claim 7 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III in which 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.

13. A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV ##STR40## in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 6 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylalkyl groups in which the cycloalkyl group contains 3 to 6 carbon atoms and the alkyl group contains 1 to 3 carbon atoms, alkenyl groups containing 2 to 6 carbon atoms, alkynyl groups containing 2 to 6 carbon atoms and groups of formula II ##STR41## in which R.sub.9 and R.sub.10, which are the same or different are selected from the group consisting of H, halo and alkoxy groups containing 1 to 3 carbon atoms;

in which 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 or R.sub.3 and R.sub.4 together with the nitrogen atom form an optionally substituted heterocyclic ring having 5 or 6 atoms in the ring optionally containing further hetero atoms in addition to the nitrogen atom;

in which R.sub.5 is selected from the group consisting of 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 and phenyl;

in which R.sub.6 is fluoro or methyl;

or a pharmaceutically acceptable salt thereof.

14. A method of treating depression as claimed in claim 13 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV in which R.sub.1 is selected from the group consisting of straight or branched chain alkyl groups containing 1 to 4 carbon atoms, cycloalkyl groups containing 3 to 7 carbon atoms, cycloalkylmethyl groups in which the cycloalkyl ring contains 3 to 6 carbon atoms and groups of formula II in which R.sub.9 and R.sub.10 are selected from the group consisting of H, fluoro or methoxy and in which R.sub.2 is H or methyl.

15. A method of treating depression as claimed in claim 13 which comprises administering to a depressed patient or a therapeutically active amount of a compound of formula IV in which R.sub.1 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, secondary butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl and phenyl.

16. A method of treating depression as claimed in claim 13 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl, ethyl and formyl.

17. A method of treating depression as claimed in claim 13 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV in which R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring containing one nitrogen atom and 4 or 5 carbon atoms which is optionally substituted by one or more alkyl groups or R.sub.3 and R.sub.4 together with the nitrogen atom to which tehy are attached form a heterocyclic ring containing a second nitrogen atom which is optionally alkylated or a heterocyclic ring including one or more double bonds.

18. A method of treating depression as claimed in claim 13 which comprises administering to a depressed patient a therapeutically active amount of a compound of formula IV in which R.sub.5 is selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy and phenyl.

19. A method of treating depression which comprises administering to a depressed patient a therapeutically active amount of a compound of formula III ##STR42## in which R.sub.1 is selected from the group consisting of methyl, propyl, isobutyl and phenyl; 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 and their pharmaceutically acceptable salts.

20. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of 1-[1-(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

21. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

22. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N-methyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

23. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]butylamine or a pharmaceutically acceptable salt thereof.

24. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N-methyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine or a pharmaceutically acceptable salt thereof.

25. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine or a pharmaceutically acceptable salt thereof.

26. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cyclobutyl]-3-methylbutylamine or a pharmaceutically acceptable salt thereof.

27. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

28. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of N,N-dimethyl-1-[1-(3,4-dichlorophenyl)cylobutyl]ethylamine or a pharmaceutically acceptable salt thereof.

29. A method of treating depression as claimed in claim 1 which comprises administering to a depressed patient a therapeutically active amount of .alpha.-[1-(4-chlorophenyl)cyclobutyl]benzylamine or a pharmaceutically acceptable salt thereof.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

How are People Using DrugPatentWatch?

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

`abc