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8-Carboxylester, and 8-carbamyl derivitives of 5,6,7,8-tetrahydroquinoline
| Details |
|
Inventors: Curran, Adrian Charles Ward; Crossley, Roger; Hill, David George;
Assignee: John Wyeth & Brother Limited (Maidenhead, EN)
Primary Examiner: Daus; Donald G.
Assistant Examiner: Wheeler; David E.
Attorney, Agent or Firm: Wilfond; Arthur E.
The invention relates to novel 5,6,7,8-tetrahydroquinoline derivatives which have a group X situated at the 8-position said group X is CONHR.sup.3, or CO.sub.2 R.sup.5 wherein R.sup.3 is hydrogen lower alkyl and R.sup.5 is hydrogen, lower alkyl or a lower aralkyl radical. The compounds are intermediates for corresponding compounds where X is CSNHR.sup.3 and these are anti-ulcer agents. |
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DETAILED DESCRIPTION We claim: 1.
A compound of formula I l ##STR11## and acid addition salts thereof with pharmaceutically acceptable acids, wherein R.
sup.
1, R.
sup.
2 and R.
sup.
6 are the same or different and are selected from hydrogen, alkyl containing from 1 to 6 carbon atoms, phenylalkyl wherein the alkyl group has 1-6 carbon atoms, or phenyl groups or R.
sup.
1 and R.
sup.
2 taken together represent a polymethylene chain of 3 to 5 carbon atoms, R.
sup.
7 represents hydrogen, alkyl of 1 to 6 carbon atoms or gem di n-alkyl of 1-6 carbon atoms, phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms or phenyl, X is CONHR.
sup.
3 or CO.
sub.
2 R.
sup.
5 wherein R.
sup.
3 is hydrogen or alkyl of 1 to 6 carbon atoms, and R.
sup.
5 is hydrogen, alkyl of 1 to 6 carbon atoms or phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms and metal salts of the compounds wherein X is CO.
sub.
2 R.
sup.
5 and R.
sup.
5 is hydrogen with the proviso that when R.
sup.
1 and R.
sup.
2 or R.
sup.
2 and R.
sup.
6 are both alkyl they are selected from normal and secondary alkyl groups 2.
A compound as claimed in claim 1, or an acid addition salt thereof with a pharmaceutically acceptable acid wherein R.
sup.
1, R.
sup.
2, R.
sup.
6 and R.
sup.
7 are the same or different and are selected from hydrogen and lower alkyl of 1 to 4 carbon atoms.
3.
A compound as claimed in claim 1 wherein R.
sup.
1, R.
sup.
2, R.
sup.
3 and R.
sup.
6 are selected from hydrogen and methyl.
4.
A compound as claimed in claim 1, wherein R.
sup.
1, R.
sup.
2 and R.
sup.
6 are selected from hydrogen and t-butyl.
5.
A compound as claimed in claim 1, which has the formula ##STR12## wherein R.
sup.
1, R.
sup.
2, R.
sup.
3 and R.
sup.
6 are selected from hydrogen and methyl.
6.
A compound as claimed in claim 1, which has the formula ##STR13## wherein R.
sup.
1, R.
sup.
7 and X are as defined in claim 1.
7.
A compound as claimed in claim 1, which has the formula: ##STR14## 8.
A compound as claimed in claim 1, which is 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid.
9.
The sodium salt of the compound claimed in claim 8
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