US4659718A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antihypertensive 3-tetrazoyl-4-quinolones
Assignee: Boots Co PLC
•
Filing: 1985-06-26
•
Granted: 1987-04-21
•
Expires: 2005-06-26
Abstract
Abstract Novel quinolones of formula I <IMAGE> I and pharmaceutically acceptable acid addition salts thereof in which the dotted line between positions 2 and 3 of the quinolone ring represents an optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R1 is lower alkyl; R2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group -NR4R5 or the N-oxide thereof wherein R4 and R5, which may be the same or different, are lower alkyl or, together with the nitrogen atom to which they are attached form a pyrrolidino, piperidino or morpholino radical; and R3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R3 is lower alkoxy, R2 is other than lower alkoxy have utility as antihypertensive agents. Processes for preparing the quinolones and pharmaceutical compositions containing them are disclosed.
Inventors
- 👤 Roy V. Davies
- 👤 Richard D. Green
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:55
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D265/00; C07D265/04; C07D265/12; C07D265/14; C07D265/24; C07D265/26; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
101 words
A quinolone of the formula I ##STR12## in which the dotted lines between positions 2 and 3 of the quinolone ring represents an optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy.
Claim 2
Dependent Claim
101 words
A quinolone of the formula I ##STR12## in which the dotted lines between positions 2 and 3 of the quinolone ring represents an optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy.
Claim 3
Dependent Claim
11 words
A quinolone according to claim 1 in which R is hydrogen.
Claim 4
Dependent Claim
11 words
A quinolone according to claim 1 in which R is 1-methyl.
Claim 5
Dependent Claim
56 words
A quinolone according to claim 1 of formula IX ##STR13## in which R 1 is lower alkyl, R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano or difluoromethoxy and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy, provided that when R 3 is lower alkoxy, R 2 is other than lower alkoxy.
Claim 6
Dependent Claim
20 words
A quinolone according to claim 4 in which the lower alkyl and lower alkoxy moieties are of one carbon atom.
Claim 7
Dependent Claim
12 words
A quinolone according to claim 5 in which R 3 is fluoro.
Claim 8
Dependent Claim
12 words
A quinolone according to claim 5 in which R 3 is hydrogen.
Claim 9
Dependent Claim
21 words
A quinolone according to claim 1 of formula X ##STR14## in which R 2 is hydrogen, halo, methyl, methoxy or trifluoromethyl.
Claim 10
Dependent Claim
22 words
A quinolone according to claim 1 of formula XI ##STR15## in which R 2 is hydrogen, halo, methyl, ethyl, methoxy or trifluoromethyl.
Claim 11
Dependent Claim
12 words
The quinolone according to claim 9 in which R 2 is hydrogen.
Claim 12
Dependent Claim
12 words
The quinolone according to claim 9 in which R 2 is methyl.
Claim 13
Dependent Claim
134 words
A pharmaceutical composition useful for effecting antihypertensive activity and vasodilation in mammals including humans which comprises an antihypertensively effective amount or a vasodilating effective amount of a quinolone of the formula I ##STR16## in which the dotted lines between positions 2 and 3 of the quinolone ring represents and optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy, in combination with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
134 words
A pharmaceutical composition useful for effecting antihypertensive activity and vasodilation in mammals including humans which comprises an antihypertensively effective amount or a vasodilating effective amount of a quinolone of the formula I ##STR16## in which the dotted lines between positions 2 and 3 of the quinolone ring represents and optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethoxy, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy, in combination with a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
63 words
A pharmaceutical composition according to claim 12 in which the quinolone is of the formula IX ##STR17## in which R 1 is lower alkyl, R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano or difluoromethoxy and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy, provided that when R 3 is lower alkoxy, R 2 is other than lower alkoxy.
Claim 16
Dependent Claim
21 words
A pharmaceutical composition according to claim 13 in which the lower alkyl and lower alkoxy moieties are of one carbon atom.
Claim 17
Dependent Claim
13 words
A pharmaceutical composition according to claim 14 in which R 3 is fluoro.
Claim 18
Dependent Claim
13 words
A pharmaceutical composition according to claim 14 in which R 3 is hydrogen.
Claim 19
Dependent Claim
28 words
A pharmaceutical composition according to claim 12 in which the quinolone is of the formula X ##STR18## in which R 2 is hydrogen, halo, methyl, methoxy or trifluoromethyl.
Claim 20
Dependent Claim
28 words
A pharmaceutical composition according to claim 12 in which quinoline is of the formula XI ##STR19## in which R 2 is hydrogen, halo, methyl, ethyl, methoxy or trifluoromethyl.
Claim 21
Dependent Claim
13 words
A pharmaceutical composition according to claim 18 in which R 2 is hydrogen.
Claim 22
Dependent Claim
13 words
A pharmaceutical composition according to claim 18 in which R 2 is methyl.
Claim 23
Independent Claim
135 words
A method of treating hypertension and effecting vasodilation in mammals including humans which comprises administering to such a mammal in need thereof a therapeutically effective amount of a quinolone of the formula I ##STR20## in which the dotted lines between positions 2 and 3 of the quinolone ring represents and optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethyl, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy, in combination with a pharmaceutically acceptable carrier.
Claim 24
Independent Claim
135 words
A method of treating hypertension and effecting vasodilation in mammals including humans which comprises administering to such a mammal in need thereof a therapeutically effective amount of a quinolone of the formula I ##STR20## in which the dotted lines between positions 2 and 3 of the quinolone ring represents and optional bond, R is hydrogen, 1-methyl or 2-lower alkyl; R 1 is lower alkyl; R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano, difluoromethyl, methylsulphinyl, phenylsulphinyl or the group --NR 4 R 5 or the N-oxide thereof wherein R 4 and R 5 are the same or different lower alkyl; and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy provided that, when R 3 is lower alkoxy, R 2 is other than lower alkoxy, in combination with a pharmaceutically acceptable carrier.
Claim 25
Dependent Claim
62 words
A method according to claim 21 in which the quinolone is of the formula IX ##STR21## in which R 1 is lower alkyl, R 2 is hydrogen, halo, lower alkyl, lower alkoxy, trifluoromethyl, cyano or difluoromethoxy and R 3 is hydrogen, fluoro, lower alkyl or lower alkoxy, provided that when R 3 is lower alkoxy, R 2 is other than lower alkoxy.
Claim 26
Dependent Claim
20 words
A method according to claim 22 in which the lower alkyl and lower alkoxy moieties are of one carbon atom.
Claim 27
Dependent Claim
12 words
A method according to claim 23 in which R 3 is fluoro.
Claim 28
Dependent Claim
12 words
A method according to claim 23 in which R 3 is hydrogen.
Claim 29
Dependent Claim
27 words
A method according to claim 21 in which the quinolone is of the formula X ##STR22## in which R 2 is hydrogen, halo, methyl, methoxy or trifluoromethyl.
Claim 30
Dependent Claim
28 words
A method according to claim 21 in which the quinolone is of the formula XI ##STR23## in which R 2 is hydrogen, halo, methyl, ethyl, methoxy or trifluoromethyl.
Claim 31
Dependent Claim
12 words
A method according to claim 27 in which R 2 is hydrogen.
Claim 32
Dependent Claim
12 words
A method according to claim 27 in which R 2 is methyl.
References Cited (Backward Citations)
JPS50106975A
Cited
US4035368A
Cited
US4474787A
Cited
US4259437A
Cited
US4302460A
Cited
US4442109A
Cited
EP0104018A2
Cited
EP0120483A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-04-20 | 1990-10-20 | 1991-04-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-20 | 1994-10-20 | 1995-04-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-20 | 1998-10-20 | 1999-04-21 | $7700.00 | Window Closed / Lapsed |