US4085215A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Certain 5,6,7,8-tetrahydroquinoline-8-thiocarboxamides
Assignee: John Wyeth and Brother Ltd
•
Filing: 1975-07-30
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Granted: 1978-04-18
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Expires: 1995-07-30
Abstract
Abstract The invention relates to novel pyridine derivatives which have a fused 5,6, or 7-membered saturated hydrocarbon ring adjacent to the nitrogen of the pyridine ring, and a group X situated on said hydrocarbon ring and separated by one carbon atom from the pyridine nitrogen atom, said group X is cyano, CONHR 3 , CSNHR 3 or CO 2 R 5 wherein R 3 is selected from hydrogen, lower alkyl and lower aralkyl radicals and R 5 is selected from hydrogen, lower alkyl and lower aralkyl radicals which may be substituted by alkyl, alkoxy, halogen, nitro or trifluoromethyl; other substituents may be present. Compounds wherein X is CSNHR 3 are anti-ulcer agents and the other compounds are intermediates therefor.
Inventors
- 👤 Adrian Charles Ward Curran
- 👤 Roger Crossley
- 👤 David George Hill
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 23:19
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/04; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/72; C07C45/73; C07D215/16; C07D215/20; C07D215/48; C07D219/00; C07D219/02; C07D219/04; C07D221/00; C07D221/02; C07D221/04; C07D221/06; C07D221/16; C07F; C07F3/00; C07F3/003
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
255 words
A compound of the formula ##STR12## or a acid addition salt thereof with a pharmaceutically acceptable acid, wherein R 1 , R 2 and R 6 are the same or different and are selected from hydrogen, trifluoromethyl, alkyl having from 1 to 6 carbon atoms, phenylalkyl wherein the alkyl group has 1 to 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 or from 1 to 3 groups selected from alkyl of 1 to 6 carbon atoms (which may be substituted by alkoxy of 1 to 6 carbon atoms or trifluoromethyl), phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms and phenyl groups, R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and any of the phenyl or the phenyl portion of any phenylalkyl groups R 1 , R 2 , R 6 and R 7 may be substituted by alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen, nitro or trifluoromethyl with the provisos that (1) when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups and (2) when two alkyl R 7 groups are present on the same carbon atom then they are both n-alkyl groups and when two R 7 alkyl groups are present on adjacent carbon atoms they are selected from normal and secondary alkyl groups.
Claim 2
Dependent Claim
255 words
A compound of the formula ##STR12## or a acid addition salt thereof with a pharmaceutically acceptable acid, wherein R 1 , R 2 and R 6 are the same or different and are selected from hydrogen, trifluoromethyl, alkyl having from 1 to 6 carbon atoms, phenylalkyl wherein the alkyl group has 1 to 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 or from 1 to 3 groups selected from alkyl of 1 to 6 carbon atoms (which may be substituted by alkoxy of 1 to 6 carbon atoms or trifluoromethyl), phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms and phenyl groups, R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and any of the phenyl or the phenyl portion of any phenylalkyl groups R 1 , R 2 , R 6 and R 7 may be substituted by alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen, nitro or trifluoromethyl with the provisos that (1) when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups and (2) when two alkyl R 7 groups are present on the same carbon atom then they are both n-alkyl groups and when two R 7 alkyl groups are present on adjacent carbon atoms they are selected from normal and secondary alkyl groups.
Claim 3
Dependent Claim
56 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, and R 3 is hydrogen or methyl.
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
27 words
A compound as claimed in claim 1, wherein R 1 , R 2 and R 6 are selected from hydrogen and t-butyl and R 3 is hydrogen.
Claim 6
Dependent Claim
10 words
A compound as claimed in claim 1, which is 3,4-dimethyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide.
Claim 7
Dependent Claim
10 words
A compound as claimed in claim 2, which is 2-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide.
Claim 8
Dependent Claim
20 words
A compound as claimed in claim 2, which is selected from 3-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide and the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
10 words
A compound as claimed in claim 2, which is 4-methyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide.
Claim 10
Dependent Claim
10 words
A compound as claimed in claim 2, which is 3-methyl-5,6,7,8-tetrahydroquinoline-8-(N-methyl)-thiocarboxamide.
Claim 11
Dependent Claim
10 words
A compound as claimed in claim 3, which is 2-t-butyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide.
Claim 12
Dependent Claim
10 words
A compound as claimed in claim 1, which is 2-phenyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide.
Claim 13
Dependent Claim
81 words
A compound as claimed in claim 1, which is 5,6,7,8-tetrahydroquinoline-8-thiocarboxamide (having the following nmr spectrum in d 6 DMSO (100MH z ): ______________________________________
δ1.5- 2.3
broad multiplet
4 protons CH.sub.2 -6 and 7
δ2.7
multiplet 2 protons CH.sub.2 -5
δ4.15
triplet (j=7Hz)
1 proton CH-8
δ7.08
quartet 1 proton H-3
δ7.44
quartet 1 proton H-4
δ8.29
quartet 1 proton H-2
δ9.25 and 9.45 broad doublet
2 protons NH.sub.2
Coupling constants = J.sub.23 = 5Hz, J.sub.24 = 1.5Hz, J.sub.34 =
______________________________________
8Hz.
Claim 14
Dependent Claim
18 words
A compound as claimed in claim 1, which is 3,6-dimethyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
18 words
A compound as claimed in claim 1, which is 3,5-dimethyl-5,6,7,8-tetrahydroquinoline-8-thiocarboxamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
28 words
A pharmaceutical composition for treating ulcers comprising an effective amount of a compound as claimed in claim 1 and pharmaceutically acceptable salts thereof, and a pharmaceutically acceptable carrier.
Claim 17
Dependent Claim
12 words
A pharmaceutical composition as claimed in claim 15, in unit dosage form.
Claim 18
Independent Claim
271 words
A method of treating ulcers in an afflicted host which method comprises administering to said host a compound of the formula ##STR13## or a acid addition salt thereof with a pharmaceutically acceptable acid, wherein R 1 , R 2 and R 6 are the same or different and are selected from hydrogen, trifluoromethyl, alkyl having from 1 to 6 carbon atoms, phenylalkyl wherein the alkyl group has 1 to 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 or from 1 to 3 groups selected from alkyl of 1 to 6 carbon atoms (which may be substituted by alkoxy of 1 to 5 carbon atoms or trifluoromethyl), phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms and phenyl groups, R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and any of the phenyl or the phenyl portion of any phenylalkyl groups R 1 , R 2 , R 6 and R 7 may be substituted by alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen, nitro or trifluoromethyl with the provisos that (1) when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups and (2) when two alkyl R 7 groups are present on the same carbon atom then they are both n-alkyl groups and when two R 7 alkyl groups are present on adjacent carbon atoms they are selected from normal and secondary alkyl groups.
Claim 19
Independent Claim
271 words
A method of treating ulcers in an afflicted host which method comprises administering to said host a compound of the formula ##STR13## or a acid addition salt thereof with a pharmaceutically acceptable acid, wherein R 1 , R 2 and R 6 are the same or different and are selected from hydrogen, trifluoromethyl, alkyl having from 1 to 6 carbon atoms, phenylalkyl wherein the alkyl group has 1 to 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 or from 1 to 3 groups selected from alkyl of 1 to 6 carbon atoms (which may be substituted by alkoxy of 1 to 5 carbon atoms or trifluoromethyl), phenylalkyl wherein the alkyl group has 1 to 6 carbon atoms and phenyl groups, R 3 is hydrogen or alkyl of 1 to 6 carbon atoms, and any of the phenyl or the phenyl portion of any phenylalkyl groups R 1 , R 2 , R 6 and R 7 may be substituted by alkyl of 1 to 6 carbon atoms, lower alkoxy of 1 to 6 carbon atoms, halogen, nitro or trifluoromethyl with the provisos that (1) when R 1 and R 2 or R 2 and R 6 are both alkyl they are selected from normal and secondary alkyl groups and (2) when two alkyl R 7 groups are present on the same carbon atom then they are both n-alkyl groups and when two R 7 alkyl groups are present on adjacent carbon atoms they are selected from normal and secondary alkyl groups.
Claim 20
Dependent Claim
10 words
A compound as claimed in claim 1 which is 5,6,7,8-tetrahydroquinoline-8-(N-methyl)thiocarboxamide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-17 | 1981-10-17 | 1982-04-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-17 | 1985-10-17 | 1986-04-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-17 | 1989-10-17 | 1990-04-18 | $7700.00 | Window Closed / Lapsed |