.

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

Claims for Patent: 4,695,578

« Back to Dashboard

Claims for Patent: 4,695,578

Title: 1,2,3,9-tetrahydro-3-imidazol-1-ylmethyl-4H-carbazol-4-ones, composition containing them, and method of using them to treat neuronal 5HT function disturbances
Abstract:The invention relates to compounds of formula (I). ##STR1## wherein R.sub.1 represents a hydrogen atom or a C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-6 alkenyl, C.sub.3-7 cycloalkyl-(C.sub.1-4) alkyl, C.sub.3-10 alkynyl, phenyl or phenyl-C.sub.1-3 alkyl group, and one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or phenyl-(C.sub.1-3) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; and physiologically acceptable salts and solvates, e.g. hydrates thereof. The compounds are potent selective antagonists at "neuronal" 5-hydroxytryptamine receptors and are useful in the treatment of migraine and psychotic disorders such as schizophrenia.
Inventor(s): Coates; Ian H. (Hertfordshire, GB2), Bell; James A. (Royston, GB2), Humber; David C. (Ealing, GB2), Ewan; George B. (Gerrard's Cross, GB2)
Assignee: Glaxo Group Limited (London, GB2)
Application Number:06/931,032
Patent Claims: 1. A compound of formula (I) ##STR20## wherein R.sup.1 represents a hydrogen atom or a C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-6 alkenyl, C.sub.3-7 cycloalkyl-(C.sub.1-4)alkyl, C.sub.3-10 alkynyl, phenyl or phenyl-C.sub.1-3 alkyl group, and one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or phenyl-(C.sub.1-3) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; or a physiologically acceptable salt or solvate thereof.

2. A compound according to claim 1 in which one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 represents a C.sub.1-3 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 alkenyl group and each of the other two groups, which may be the same or different represents a hydrogen atom or a C.sub.1-3 alkyl group.

3. A compound according to claim 1 in which R.sup.1 represents a hydrogen atom or a C.sub.1-6 alkyl, C.sub.5-6 cycloalkyl or C.sub.3-4 alkenyl group and either R.sup.2 represents a hydrogen atom and R.sup.3 and/or R.sup.4 represents a C.sub.1-3 alkyl group or R.sup.2 represents a C.sub.1-3 alkyl group and both R.sup.3 and R.sup.4 represent hydrogen atoms.

4. A compound of formula (I) ##STR21## wherein R.sup.1 represents a hydrogen atom or a C.sub.1-10 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-6 alkenyl, phenyl or phenyl-C.sub.1-3 alkyl group; and one of the groups represented by R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.2-6 alkenyl or phenyl(C.sub.1-3) alkyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-6 alkyl group; or a physiologically acceptable salt or solvate thereof.

5. A compound according to claim 4 in which R.sup.1 represents a hydrogen atom or a C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 alkenyl group.

6. A compound according to claim 4 in which one of the groups represented R.sup.2, R.sup.3 and R.sup.4 represents a C.sub.1-3 alkyl, C.sub.3-6 cycloalkyl or C.sub.3-6 alkenyl group and each of the other two groups, which may be the same or different, represents a hydrogen atom or a C.sub.1-3 alkyl group.

7. A compound according to claim 4 in which R.sup.1 represents a hydrogen atom or a C.sub.1-6 alkyl, C.sub.5-6 cycloalkyl or C.sub.3-4 alkenyl group and either R.sup.2 represents a hydrogen atom and R.sup.3 and/or R.sup.4 represents a C.sub.1-3 alkyl group or R.sup.2 represents a C.sub.1-4 3 alkyl group and R.sup.3 and R.sup.4 both represent hydrogen atoms.

8. A compound of formula (Ia) ##STR22## wherein R.sup.1a represents a hydrogen atom or a methyl, ethyl, propyl, prop-2-yl, prop-2-enyl or cyclopentyl group; R.sup.3a represents a hydrogen atom; and either R.sup.2a represents a methyl, ethyl, propyl or prop-2-yl group and R.sup.4a represents a hydrogen atom or R.sup.2a represents a hydrogen atom and R.sup.4a represents a methyl or ethyl group; or a physiologically acceptable salt or solvate thereof.

9. 1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)met hyl]-4H-carbazol-4-one or a physiologically acceptable salt or solvate thereof.

10. 1,2,3 ,9-Tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)-methyl]-9-(prop-2-enyl)-4H-car bazol-4-one; 9-Cyclopentyl-1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H- carbazol-4-one; 1,2,3,9-Tetrahydro-3-[2-methyl-1H-imidazol-1-yl)methyl]-9-(prop-2-yl)-4H-c arbazol-4-one; or a physiologically acceptable salt or solvate thereof.

11. A pharmaceutical composition for the treatment of a condition caused by disturbance of "neuronal" 5HT function comprising at least one compound of formula (I) as defined in claim 1 or a physiologically acceptable salt or solvate thereof in an amount effective to relieve said condition together with at least one physiologically acceptable carrier or exipient.

12. A method of treating a condition caused by disturbance of "neuronal" 5HT function which comprises administering to a patient an effective amount of a compound of formula (I) as defined in claim 1 or a physiologically acceptable salt or solvate thereof to relieve said condition.

13. The compound of claim 9 in the form of a hydrochloride salt.

14. The compound of claim 9 in the form of the hydrochloride dihydrate.

15. A pharmaceutical composition according to claim 11 in which said compound of formula (I) is 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4-H-carb azol-4-one or a physiologically acceptable salt or solvate thereof.

16. A pharmaceutical composition according to claim 15 in which said compound is present as a hydrochloride salt.

17. A pharmaceutical composition according to claim 15 in which said compound is present as the hydrochloride dihydrate.

18. A method according to claim 12 in which said compound of formula (I) is 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1yl)methyl]-4H-carbaz ol-4-one or a physiologically acceptable salt or solvate thereof.

19. A method according to claim 18 in which said compound is used as a hydrochloride salt.

20. A method according to claim 18 in which said compound is used as the hydrochloride dihydrate.
« 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