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Generated: June 24, 2017

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Claims for Patent: 5,827,871

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Claims for Patent: 5,827,871

Title: Medicaments 1,2,3,4-tetrahydrocarbazoles and 5-HT.sub.1 agonist use thereof
Abstract:Use of a compound of general formula (I): ##STR1## wherein R.sup.1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, arylC.sub.1-6 alkoxy, --CO.sub.2 R.sup.4, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, C.sub.1-6 alkanoylamino(CH.sub.2).sub.n, or C.sub.1-6 alkylsulphonylamino(CH.sub.2).sub.n ; R.sup.4 represents hydrogen, C.sub.1-6 alkyl or arylC.sub.1-6 alkyl; R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a ring; n represents 0, 1 or 2; and R.sup.2 and R.sup.3 each independently represent hydrogen, C.sub.1-6 alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring; or a physiologically acceptable salt thereof, in the manufacture of a medicament for the treatment of a condition where a 5-HT.sub.1 -like agonist is indicated, for example migraine. Novel compounds of formula (I), processes for preparing them and pharmaceutical compositions containing them are also described.
Inventor(s): King; Francis David (Harlow, GB2), Gaster; Laramie Mary (Harlow, GB2), Kaumann; Alberto Julio (Trumpington, GB2), Young; Rodney Christopher (Hertford, GB2)
Assignee: Smithkline Beecham plc (GB2)
Application Number:08/442,720
Patent Claims: 1. A method of treatment of a condition wherein a 5-HT.sub.1 -like agonist is indicated, which comprises administering to a subject in need thereof an effective amount of a compound of general formula (I): ##STR9## wherein R.sup.1 represents hydrogen, halogen, trifluoromethyl, nitro, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, arylC.sub.1-6 alkoxy, --CO.sub.2 R.sup.4, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, C.sub.1-6 alkanoylamino(CH.sub.2).sub.n, or C.sub.1-6 alkylsulphonylamino(CH.sub.2).sub.n ;

R.sup.4 represents hydrogen, C.sub.1-6 alkyl or arylC.sub.1-6 alkyl;

R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring, which may optionally contain a further heteroatom selected from oxygen, sulphur or nitrogen;

n represents 0, 1 or 2; and

R.sup.2 and R.sup.3 each independently represent hydrogen, C.sub.1-6 alkyl or benzyl or together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or hexahydroazepino ring;

or a physiologically acceptable salt, solvate or hydrate thereof.

2. The method according to claim 1 wherein the condition is migraine.

3. The method according to claim 1 wherein in the compound of formula (I) R.sup.1 represents halogen, CF.sub.3, C.sub.1-6 alkoxy, --(CH.sub.2).sub.n CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 RN.sup.5 R.sup.6 or C.sub.1-6 alkanoylamino, and R.sup.5 and R.sup.6 are as hereinbefore defined.

4. The method according to claim 1 wherein in the compound of formula (I) R.sup.1 is a group --(CH.sub.2).sub.n CONR.sup.5 R.sup.6 wherein n is zero and R.sup.5 and R.sup.6 each independently represent hydrogen, methyl, ethyl or propyl; and R.sup.2 and R.sup.3 each independently represent hydrogen, methyl or ethyl.

5. The method according to claim 2 wherein in the compound of formula (I) R.sup.1 is a group --(CH.sub.2).sub.n CONR.sup.5 R.sup.6 wherein n is zero and R.sup.5 and R.sup.6 each independently represent hydrogen, methyl, ethyl or propyl; and R.sup.2 and R.sup.3 each independently represent hydrogen, methyl or ethyl.

6. The method according to claim 4 wherein in the compound of formula (I) R.sup.5 and R.sup.6 each independently represent hydrogen or methyl.

7. The method according to claim 5 wherein in the compound of formula (I) R.sup.5 and R.sup.6 each independently represent hydrogen or methyl.

8. A compound of formula (IA): ##STR10## wherein R.sup.1 represents nitro, --CO.sub.2 R.sup.4, CN, --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, --(CH.sub.2).sub.n SO.sub.2 NR.sup.5 R.sup.6, or C.sub.1-6 alkylsulphonylamino(CH.sub.2).sub.n ;

R.sup.4 represents arylC.sub.1-6 alkyl;

R.sup.5 and R.sup.6 each independently represent hydrogen or C.sub.1-6 alkyl, or R.sup.5 and R.sup.6 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring, which may optionally contain a further heteroatom selected from oxygen, sulphur or nitrogen; and

n represents 0, 1 or 2;

or a physiologically acceptable salt, solvate or hydrate thereof.

9. A compound of formula (IA) according to claim 8 wherein R.sup.1 represents --(CH.sub.2).sub.n CONR.sup.5 R.sup.6, wherein n represents 0 and R.sup.5 and R.sup.6 each independently represent hydrogen, methyl, ethyl or propyl.

10. A compound of formula (IA) according to claim 9 wherein R.sup.5 and R.sup.6 each independently represent hydrogen or methyl.

11. A compound of formula (I) according to claim 8, which is selected from:

3-Amino-6-cyano-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(N-methylsulphonamidomethyl)-1,2,3,4-tetrahydrocarbazole;

3-amino-6-sulphonamido-1,2,3,4-tetrahydrocarbazole;

3-amino-6-nitro-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(piperidin-1-ylcarbonyl)-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(pyrrolidin-1-ylcarbonyl)-1,2,3,4-tetrahydrocarbazole;

3-amino-6-methanesulphonamido-1,2,3,4-tetrahydrocarbazole;

or a physiologically acceptable salt, solvate or hydrate thereof.

12. A compound of formula (I) according to claim 8, which is selected from:

3-amino-6-(N-methylcarboxamido)-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(N,N-dimethylcarboxamido)-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(N,N-diethylcarboxamido)-1,2,3,4-tetrahydrocarbazole;

or a physiologically acceptable salt, solvate or hydrate thereof.

13. A compound of formula (I) according to claim 8, which is selected from:

3-amino-6-carboxamidomethyl-1,2,3,4-tetrahydrocarbazole;

3-amino-6-(2-carboxamidoethyl)-1,2,3,4-tetrahydrocarbazole;

or a physiologically acceptable salt, solvate or hydrate thereof.

14. A compound of formula (I) according to claim 8, which is (+)-3-amino-6-carboxamido-1,2,3,4-tetrahydrocarbazole or a physiologically acceptable salt, solvate or hydrate thereof.

15. A compound of formula (I) according to claim 8, which is (-)-3-amino-6-carboxamido-1,2,3,4-tetrahydrocarbazole or a physiologically acceptable salt, solvate or hydrate thereof.

16. A compound of formula (I) according to claim 8 wherein the said physiologically acceptable salt is formed from hydrochloric, sulphuric, phosphoric, succinic, maleic, acetic or fumaric acid.

17. A pharmaceutical composition comprising a compound of formula (I) according to claim 8, or a physiologically acceptable salt, solvate or hydrate thereof and a physiologically acceptable carrier.
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