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Claims for Patent: 5,863,935

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Claims for Patent: 5,863,935

Title: Therapeutic heterocyclic compounds
Abstract:
Inventor(s): Robertson; Alan D. (Beckenham, GB2), Hill; Alan P. (Beckenham, GB2), Glen; Robert C. (Beckenham, GB2), Martin; Graeme R. (Beckenham, GB2)
Assignee: Zeneca Limited (GB)
Application Number:08/471,229
Patent Claims: 1. A process for the preparation of a compound of formula (I) ##STR37## wherein n is an integer of from 0 to 3;

W is a group of formula (i), (ii), or (iii) ##STR38## wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulphur and the chiral center * in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions; and

Z is a group of the formula (iv)

wherein R.sup.1 and R.sup.2 are independently selected from hydrogen and C.sub.1-4 alkyl;

which process comprises

reacting a compound of formula (II) ##STR39## wherein n and W are as hereinbefore defined, with a compound of formula (III) ##STR40## or a carbonyl-protected form thereof, wherein L is --NR.sup.1 R.sup.2 wherein R.sup.1 and R.sup.2 are as hereinbefore defined or halogen or a protected amino group which can be converted in situ to an amino group;

and optionally converting the compound of formula (I) so formed to a corresponding physiologically acceptable salt or solvate.

2. A process for the preparation of a compound of formula (I) ##STR41## wherein n is an integer of from 0 to 3;

W is a group of formula (i), (ii), or (iii) ##STR42## wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulphur and the chiral center * in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions; and

Z is a group of the formula (vi) ##STR43## wherein R.sup.3 is hydrogen or C.sub.1-4 alkyl, which process comprises

(1) condensing a compound of the formula: ##STR44## where W and n are as defined above with a compound of the formula (XXVIII) ##STR45## wherein R.sup.3 is as defined above, and thereafter (2) reducing the reaction product of step (1) by catalytic hydrogenation to produce a compound of the formula: ##STR46## and optionally converting the compound of formula (I) so formed to a corresponding physiologically acceptable salt or solvate.

3. A process for the preparation of the compound N,N-dimethyl-2-[5-(2-oxo-1,3-oxazolidin-4-ylmethyl)-1H-indol-3-yl]ethylami ne in either its (S) or (R) form or as a mixture thereof in any proportions;

which comprises reacting a compound of formula (II) ##STR47## wherein n is 1 and W is a group ##STR48## and the chiral center * is in its (S) or (R) form or is a mixture thereof with a compound of formula (III) ##STR49## or a carbonyl-protected form thereof, wherein L is --NR.sup.1 R.sup.2 wherein R.sup.1 and R.sup.2 are each methyl or protected amino group which can be converted in situ to a dimethyl amino group

and optionally converting said compound to a corresponding physiologically acceptable salt or solvate.

4. The compound N-methyl-2-[5-(2-oxo-1,3-oxazolidin-4-yl-methyl)-1H-indol-3-yl]ethylamine or a pharmaceutically acceptable salt and/or solvate thereof.

5. The compound (S)-N-methyl-2-[5-(2-oxo-1,3-oxazolidin-4-yl-methyl)-1H-indol-3-yl]ethylam ine or a pharmaceutically acceptable salt and/or solvate thereof.

6. A method of treating or preventing migraine comprising administering to a patient in need of the same an effective amount of a compound of claim 4 or claim 5.

7. A pharmaceutical composition comprising an effective amount of a compound of claim 4 or claim 5 together with a pharmaceutically acceptable carrier.

8. A pharmaceutical composition according to claim 6 which is in the form of a tablet or capsule.

9. A process for the preparation of a compound of formula (I) ##STR50## wherein n is an integer of from 0 to 3;

W is a group of formula (i), (ii) ##STR51## wherein R is hydrogen or C.sub.1-4 alkyl, X is --O--, --S--, --NH--, or --CH.sub.2 --, Y is oxygen or sulfur and the chiral center * in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions; and

Z is a group of the formula (iv) or (vi) ##STR52## wherein R.sup.1 and R.sup.2 are independently selected form hydrogen and C.sub.1-4 alkyl;

and R.sup.3 is hydrogen or C.sub.1-4 alkyl;

which process comprises

reacting a compound of formula (XV) ##STR53## wherein n, R and X are as hereinbefore defined and Z is a group of formula (iv) or (vi), with a compound of formula (VII) ##STR54## wherein Y is as hereinbefore defined and J and K, which may be the same or different, are independently selected from chlorine, ethoxy, trichloromethyl, trichloromethoxy or imidazoyl;

and optionally converting the compound of formula (I) so formed to a corresponding physiologically acceptable salt or solvate.
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