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Claims for Patent: 5,602,162

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Claims for Patent: 5,602,162

Title: Imidazole, triazole and tetrazole derivatives
Abstract:A class of substituted imidazole, triazole and tetrazole derivatives are selective agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.
Inventor(s): Baker; Raymond (Much Hadham, GB2), Matassa; Victor G. (Furneux Pelham, GB2), Street; Leslie J. (Harlow, GB2)
Assignee: Merck, Sharp & Dohme Ltd. (Hoddesdon, GB2)
Application Number:08/438,621
Patent Claims: 1. A compound of formula I, or a pharmaceutically acceptable salt thereof: ##STR36## wherein the broken circle represents two non-adjacent double bonds in any position in the five-membered ring;

two, three or four of V, W, X, Y and Z represent nitrogen and the remainder represent carbon provided that, when two of V, W, X, Y and Z represent nitrogen and the remainder represent carbon, then the said nitrogen atoms are in non-adjacent positions within the five-membered ring;

A.sup.1 represents hydrogen, methyl, ethyl, benzyl or amino;

A.sup.2 represents a non-bonded electron pair when four of V, W, X, Y and Z represent nitrogen and the other represents carbon; or, when two or three of V, W, X, Y and Z represent nitrogen and the remainder represent carbon, A.sup.2 represents hydrogen, methyl, ethyl, benzyl or amino;

E represents a bond or a straight or branched alkylene chain containing from 1 to 4 carbon atoms;

F represents a group of formula ##STR37## U represents or C--R.sup.2 ; B represents N--R.sup.3 ;

R.sup.1 represents --CH.sub.2 .cndot.CHR.sup.4 .cndot.NR.sup.6 R.sup.7 ; and

R.sup.2, R.sup.3, R.sup.4, R.sup.6 and R.sup.7 independently represent hydrogen or C.sub.1-6 alkyl; with the exception of the compound N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and pharmaceutically acceptable salts thereof.

2. A compound as claimed in claim 1 represented by formula IIA, and pharmaceutically acceptable salts thereof: ##STR38## wherein X.sup.1 represents nitrogen or A.sup.12 --C;

n is zero, 1, 2 or 3;

B.sup.1 represents N--R.sup.13 ;

A.sup.11 and A.sup.12 independently represent hydrogen, methyl, ethyl, benzyl or amino; and

R.sup.12, R.sup.13, R.sup.14, R.sup.16 and R.sup.17 independently represent hydrogen or C.sub.1-6 alkyl.

3. A compound as claimed in claim 1 represented by formula lIB, and pharmaceutically acceptable salts thereof: ##STR39## wherein Y.sup.1 represents nitrogen or A.sup.22 --C;

n is zero, 1, 2 or 3;

B.sup.2 represents N--R.sup.23 ;

A.sup.21 and A.sup.22 independently represent hydrogen, methyl, ethyl or benzyl; and

R.sup.22, R.sup.23, R.sup.24, R.sup.26 and R.sup.27 independently represent hydrogen or C.sub.1-6 alkyl.

4. A compound as claimed in claim 1 represented by formula IIC, and pharmaceutically acceptable salts thereof: ##STR40## wherein Y.sup.2 represents nitrogen or A.sup.32 --C;

Z.sup.1 represents nitrogen or CH;

n is zero, 1, 2 or 3;

B.sup.3 represents N--R.sup.33 ;

A.sup.31 and A.sup.32 independently represent hydrogen, methyl or amino;

R.sup.31 represents --CH.sub.2 .cndot.CHR.sup.34 .cndot.NR.sup.36 R.sup.37 ; and

R.sup.32, R.sup.33, R.sup.34, R.sup.36 and R.sup.37 independently represent hydrogen or C.sub.1-6 alkyl;

with the exception of the compound N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine and pharmaceutically acceptable salts thereof.

5. A compound as claimed in claim 1 represented by formula IID, and pharmaceutically acceptable salts thereof: ##STR41## wherein W.sup.1 represents nitrogen or C--A.sup.42;

n is zero, 1, 2 or 3;

B.sup.4 represents N-R.sup.43 ;

A.sup.41 and A.sup.42 independently represent hydrogen or methyl;

R.sup.41 represents --CH.sub.2 .cndot.CHR.sup.44 .cndot.NR.sup.46 R.sup.47 ; and

R.sup.42, R.sup.43, R.sup.44, R.sup.46 and R.sup.47 independently represent hydrogen or C.sub.1-6 alkyl.

6. A compound as claimed in claim 1 selected from:

2-[5-(2-benzyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine;

2-[5-(1-benzyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(1-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine;

N ,N-dimethyl-2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indo-3-yl]ethylamine;

N,N-dimethyl-2-[5-(tetrazol-2-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(tetrazol-1-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(1-methyl-1,2,4-triazol-5-ylmethyl)-1H-indol-3-yl]ethylam ine;

N,N-dimethyl-2-[5-(1-methyl-1,2,4-triazol-3-ylmethyl)-1H-indol-3-yl]ethylam ine;

N,N-dimethyl-2-[5-(1,2,3-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(2-methylimidazol-1-ylmethyl)-1H-indo 1-3-yl ]ethylamine;

N,N-dimethyl-2-[5-(imidazol-1-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(2-methylimidazol-1-yl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(2-ethyltetrazol-5-ylmethyl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(1-ethyltetrazol-5-ylmethyl)-1H-indo -3-yl]ethylamine;

N,N-dimethyl-2-[5-(1,2,4-triazol-1-yl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(2-aminoimidazol-1-yl)-1H-indol-3-yl]ethylamine;

N,N-dimethyl-2-[5-(2-aminoimidazol-1-ylmethyl)-1H-indol-3-yl]ethylamine;

N-methyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethylamine;

and pharmaceutically acceptable salts thereof.

7. A pharmaceutical composition comprising an effective amount of a compound as claimed in claim 1 in association with a pharmaceutically acceptable carrier or excipient.

8. A method for the treatment and/or prevention of migraine and associated conditions, which method comprises administering to a patient in need of such treatment an effective amount of a compound of formula I according to claim 1 or a pharmaceutically acceptable salt thereof.
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