.

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: 4,443,449

« Back to Dashboard

Details for Patent: 4,443,449

Title: Arylcyclobutylalkylamines and anti-depression composition and methods using same
Abstract:Compounds of formula I ##STR1## in which R.sub.1 is H or C.sub.1-3 alkyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, 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, or C.sub.1-3 alkyl (with the proviso that R.sub.5 and R.sub.6 cannot both be H or methyl) or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring and R.sub.7 and/or R.sub.8 are H or C.sub.1-3 alkyl 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), Wilmshurst; Eric C. (Nottingham, GB2)
Assignee: The Boots Company Limited (Nottingham, GB2)
Filing Date:Apr 05, 1982
Application Number:06/365,287
Claims:1. A compound of the formula I ##STR39## in which R.sub.1 is H or an alkyl group containing 1 to 3 carbon atoms; in which R.sub.2 is H or an alkyl group 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, a straight or branched chain alkyl group containing 1 to 4 carbon atoms, and a cycloalkyl group in which the ring contains 3 to 7 carbon atoms,

or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of pyrrolidinyl, piperidinyl and piperazinyl, each optionally substituted by one or more methyl groups, and 1, 2, 3, 6-tetrahydropyridyl;

in which R.sub.5 and R.sub.6 which are the same or different are selected from the group consisting of H, halo, an alkyl group containing 1 to 3 carbon atoms, and trifluoromethyl (with the proviso that one of R.sub.5 and R.sub.6 is halo), or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring;

and in which R.sub.7 and R.sub.8 which are the same or different are H or an alkyl group containing 1 to 3 carbon atoms; and pharmaceutically-acceptable salts thereof.

2. A compound of the formula I as claimed in claim 1 in which R.sub.1 is H or methyl and R.sub.2 is H.

3. A compound of the formula I as claimed in claim 1 in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl and ethyl.

4. A compound of the formula I as claimed in claim 1 in which R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, and methyl (with the proviso that one of R.sub.5 and R.sub.6 is chloro) or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring.

5. A compound of the formula I as claimed in claim 1 in which R.sub.7 is H, methyl or ethyl and R.sub.8 is H.

6. A compound of the formula II ##STR40## in which R.sub.1 is H or an alkyl group containing 1 to 3 carbon atoms; in which R.sub.2 is H or an alkyl group 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, a straight or branched chain alkyl group containing 1 to 4 carbon atoms, and a cycloalkyl group in which the ring contains 3 to 7 carbon atoms,

or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of pyrrolidinyl, piperidinyl and piperazinyl, each optionally substituted by one or more methyl groups, and 1, 2, 3, 6-tetrahydropyridyl;

in which R.sub.5 and R.sub.6 which are the same or different are selected from the group consisting of H, halo, an alkyl group containing 1 to 3 carbon atoms, and trifluoromethyl (with the proviso that one of R.sub.5 and R.sub.6 is halo), or R.sub.5 and R.sub.6, together with the carbon atoms to which they are attached, form a second benzene ring;

and in which R.sub.7 and R.sub.8 which are the same or different are H or an alkyl group containing 1 to 3 carbon atoms; and pharmaceutically-acceptable salts thereof.

7. A compound of the formula II as claimed in claim 6 in which R.sub.1 is H or methyl and R.sub.2 is H.

8. A compound of the formula II as claimed in claim 6 in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl and ethyl.

9. A compound of the formula II as claimed in claim 6 in which R.sub.5 and R.sub.6 are selected from the group consisting of H, fluoro, chloro, bromo, iodo, trifluoromethyl, and methyl (with the proviso that one of R.sub.5 and R.sub.6 is chloro) or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring.

10. A compound of the formula II as claimed in claim 6 in which R.sub.7 is H, methyl or ethyl and R.sub.8 is H.

11. A compound of the formula III ##STR41## in which R.sub.1 is H or an alkyl group containing 1 to 3 carbon atoms; in which R.sub.2 is H or an alkyl group 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, a straight or branched chain alkyl group containing 1 to 4 carbon atoms, and a cycloalkyl group in which the ring contains 3 to 7 carbon atoms,

or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of pyrrolidinyl, piperidinyl and piperazinyl, each optionally substituted by one or more methyl groups, and 1, 2, 3, 6-tetrahydropyridyl;

in which R.sub.5 is selected from the group consisting of halo, trifluoromethyl, and an alkyl group containing 1 to 3 carbon atoms;

in which R.sub.6 is fluoro;

and in which R.sub.7 and R.sub.8 which are the same or different are H or an alkyl group containing 1 to 3 carbon atoms; and pharmaceutically-acceptable salts thereof.

12. A compound of the formula III as claimed in claim 11 in which R.sub.1 is H or methyl and R.sub.2 is H.

13. A compound of the formula III as claimed in claim 11 in which R.sub.3 and R.sub.4 are selected from the group consisting of H, methyl and ethyl.

14. A compound of the formula III as claimed in claim 11 in which R.sub.5 is selected from the group consisting of fluoro, chloro, bromo, iodo, trifluoromethyl and methyl.

15. A compound of the formula III as claimed in claim 11 in which R.sub.7 is H, methyl or ethyl and R.sub.8 is H.

16. A compound of the formula II ##STR42## in which R.sub.1 and R.sub.2 are H, R.sub.3 is H or methyl, R.sub.4 is H or methyl or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a pyrrolidine ring, R.sub.5 is chloro or iodo, R.sub.6 is H or chloro, R.sub.7 is H, methyl or ethyl; R.sub.8 is H and pharmaceutically-acceptable salts thereof.

17. Compound of claim 16 which is N,N-dimethyl-2-[1-(3,4-dichlorophenyl)cyclobutyl]ethylamine and its pharmaceutically acceptable salts.

18. Compound of claim 16 which is N-methyl-2-[1-(4-chlorophenyl)cyclobutyl]-1-methylethylamine and its pharmaceutically acceptable salts.

19. Compound of claim 16 which is N-{2-[1-(4-chlorophenyl)cyclobutyl]-1-methyl}ethylpyrrolidine and its pharmaceutically acceptable salts.

20. Compound of claim 16 which is 1-{[1-(3,4-dichlorophenyl)cyclobutyl]methyl}propylamine and its pharmaceutically acceptable salts.

21. Compound of claim 16 which is N,N-dimethyl-1-{[1-(3,4-dichlorophenyl)cyclobutyl]methyl}propylamine and its pharmaceutically acceptable salts.

22. Compound of claim 16 which is N,N-dimethyl-2-[1-(4-iodophenyl)cyclobutyl]ethylamine and its pharmaceutically acceptable salts.

23. A compound of the formula II ##STR43## in which R.sub.1 and R.sub.2 are both H; R.sub.3 is H or methyl; R.sub.4 is H or methyl or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from the group consisting of pyrrolidinyl, piperidinyl and piperazinyl, each optionally substituted by one or more methyl groups, and 1,2,3,6-tetrahydropyridyl; R.sub.5 is chloro or iodo; R.sub.6 is H or chloro; R.sub.7 is H, methyl or ethyl; and R.sub.8 is H, and pharmaceutically-acceptable salts thereof.

24. A pharmaceutical composition suitable as an antidepressant comprising a therapeutically effective amount of a compound of formula I as claimed in claim 1 and a pharmaceutically-acceptable diluent or carrier.

25. A pharmaceutical composition suitable as an antidepressant comprising a therapeutically effective amount of a compound of formula II as claimed in claim 6 and a pharmaceutically-acceptable diluent or carrier.

26. A pharmaceutical composition suitable as an antidepressant comprising a therapeutically effective amount of a compound of formula III as claimed in claim 11 and a pharmaceutically-acceptable diluent or carrier.

27. A pharmaceutical composition as claimed in claim 24 in unit dosage form.

28. A pharmaceutical composition as claimed in claim 25 in unit dosage form.

29. A pharmaceutical composition as claimed in claim 26 in unit dosage form.

30. A method of treating depression which comprises administering to a patient a therapeutically effective amount of a compound of formula I as defined in claim 1.

31. A method of treating depression which comprises administering to a patient a therapeutically effective amount of a compound of formula II as defined in claim 6.

32. A method of treating depression which comprises administering to a patient a therapeutically effective amount of a compound of formula III as defined in claim 11.
« Back to Dashboard

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

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