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US4009169A Expired / Lapsed US ⏱️ 0.0 years remaining

8-Carboxylester, and 8-carbamyl derivitives of 5,6,7,8-tetrahydroquinoline

Assignee: John Wyeth and Brother Ltd
•
Filing: 1975-10-20
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Granted: 1977-02-22
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Expires: 1995-10-20
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Abstract

Abstract 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 CONHR3, or CO2R5 wherein R3 is hydrogen lower alkyl and R5 is hydrogen, lower alkyl or a lower aralkyl radical.

Inventors

  • 👤 Adrian Charles Ward Curran
  • 👤 Roger Crossley
  • 👤 David George Hill

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 15:01
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/04; C07D215/16; C07D215/20; C07D215/48; C07D219/00; C07D219/04; C07D221/00; C07D221/02; C07D221/04

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 197 words
A compound of formula I l ##STR11## and acid addition salts thereof with pharmaceutically acceptable acids, wherein R 1 , R 2 and R 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 1 and R 2 taken together represent a polymethylene chain of 3 to 5 carbon atoms, R 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 3 or CO 2 R 5 wherein R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and R 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 5 and R 5 is hydrogen with the proviso that when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups
Claim 2
Dependent Claim 197 words
A compound of formula I l ##STR11## and acid addition salts thereof with pharmaceutically acceptable acids, wherein R 1 , R 2 and R 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 1 and R 2 taken together represent a polymethylene chain of 3 to 5 carbon atoms, R 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 3 or CO 2 R 5 wherein R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and R 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 5 and R 5 is hydrogen with the proviso that when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups
Claim 3
Dependent Claim 49 words
A compound as claimed in claim 1, or an acid addition salt thereof with a pharmaceutically acceptable acid wherein R 1 , R 2 , R 6 and R 7 are the same or different and are selected from hydrogen and lower alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim 25 words
A compound as claimed in claim 1 wherein R 1 , R 2 , R 3 and R 6 are selected from hydrogen and methyl.
Claim 5
Dependent Claim 22 words
A compound as claimed in claim 1, wherein R 1 , R 2 and R 6 are selected from hydrogen and t-butyl.
Claim 6
Dependent Claim 30 words
A compound as claimed in claim 1, which has the formula ##STR12## wherein R 1 , R 2 , R 3 and R 6 are selected from hydrogen and methyl.
Claim 7
Dependent Claim 26 words
A compound as claimed in claim 1, which has the formula ##STR13## wherein R 1 , R 7 and X are as defined in claim 1.
Claim 8
Dependent Claim 12 words
A compound as claimed in claim 1, which has the formula: ##STR14##
Claim 9
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylic acid.
Claim 10
Dependent Claim 10 words
The sodium salt of the compound claimed in claim 8.
Claim 11
Dependent Claim 10 words
The methyl ester of the compound claimed in claim 8.
Claim 12
Dependent Claim 10 words
A compound as claimed in claim 1, which is 2-phenyl-5,6,7,8-tetrahydroquinoline-8-carboxamide.
Claim 13
Dependent Claim 10 words
A compound as claimed in claim 1 which is 2-t-butyl-5,6,7,8-tetrahydroquinoline-8-carboxamide.
Claim 14
Dependent Claim 10 words
A compound as claimed in claim 1 which is 5,6,7,8-tetrahydroquinoline-8-carboxamide.

References Cited (Backward Citations)

US2566723A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-02-22 1980-08-23 1981-02-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-02-22 1984-08-23 1985-02-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-02-22 1988-08-23 1989-02-22 $7700.00 Window Closed / Lapsed

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