Patent US1354293A successfully refreshed from Google Patents.
US4419352A
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Pyranoquinolinones and analogs thereof
Assignee: Fisons Ltd
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Filing: 1981-02-20
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Granted: 1983-12-06
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Expires: 2001-02-20
Abstract
Abstract There are described compounds of formula I, <IMAGE> I in which an adjacent pair of R5, R6, R7 and R8 form a chain -CZC(G1)=(G2)-Z-, R4, R9 and the remainder of R5, R6, R7 and R8, which may be the same or different, each represent hydrogen, alkyl, halogen, alkenyl, -NO2, -NR1R2, -OR3, -S(O)nR3; or alkyl substituted by hydroxy, amino, alkoxy or carbonyl oxygen, n is 0, 1 or 2, R1 and R2, which may be the same or different, each represent hydrogen, alkyl, -CONHR3, phenyl or phenyl substituted by alkyl or halogen, or R1 and R2 together with the nitrogen atom to which they are attached form a 5 or 6 membered heterocyclic ring, R3 represents hydrogen, alkyl, alkenyl or phenyl, one of G1 and G2 is hydrogen and the other is a group E, each E, which may be the same or different, is -COOH, a 5-tetrazolyl group, or a carboxamidotetrazole group, each Z, which may be the same or different, is oxygen or sulphur, and one or two of the atoms, a, b, c and d are nitrogen atoms and the remainder are carbon atoms, R9 having no significance when two of a, b, c and d are nitrogen, (with certain exclusions) and pharmaceutically acceptable derivatives thereof. There are also described methods for making the compounds and pharmaceutical, e.g. anti-allergic, compositions and mixtures containing them.
Inventors
- 👤 David Cox
- 👤 Hugh Cairns
- 👤 Nigel Chadwick
- 👤 John L. Suschitzky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 09:26
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; A; A61; A61P; A61P11/00; A61P11/06; A61P37/00; A61P37/08; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/88; C07D239/90; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D311/24; C07D335/00; C07D335/04; C07D335/06; C07D495/00; C07D495/02; C07D495/04
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
394 words
A compound selected from the group having the formulas ##STR24## wherein one of the atoms a and d is nitrogen and the other is carbon, and b and c are carbon, R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , which may be the same or different, each represent hydrogen, alkyl, halogen, alkenyl, --NO 2 , --NR 1 R 2 , --OR 3 , --S(O) n R 3 ; or alkyl substituted by hydroxy, amino, alkoxy or carbonyl oxygen, n is 0, 1 or 2, R 1 and R 2 , which may be the same or different, each represent hydrogen, alkyl, --CONHR 3 , phenyl or phenyl substituted by alkyl or halogen, or R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholine, piperidine or pyrrolidine ring, R 3 represents hydrogen, alkyl, alkenyl or phenyl, one of G 1 and G 2 is hydrogen and the other is a group E, each E, which may be the same or different, is --COOH, a 5-tetrazolyl group, or a group having the formula ##STR25## R 10 and R 11 are the same or different and are hydrogen, alkyl, alkenyl, phenylalkyl, alkanoyl, or alkoxy carbonyl, and R 10 is hydrogen when R 11 is hydrogen, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 , when they contain carbon, each containing up to 8 carbon atoms, provided that when (i) either a or d is a carbon atom, (ii) E is in a position ortho to the N atom and is --COOH, a 5-tetrazolyl group or an unsubstituted (N-tetrazol-5-yl)carboxamido group, (iii) R 9 is hydrogen, (iv) G 1 is hydrogen and G 2 is a group E, and (v) R 5 , R 6 , R 7 and R 8 are selected from hydrogen, hydroxy, alkyl, halogen, alkenyl, alkoxy or --NR 1 R 2 , then R 4 is not an --OH group para to the N atom, and pharmaceutically acceptable salts, and when E is --COOH, pharmaceutically acceptable lower alkyl esters, 2-(diethylamino)esters and lower alkanoyl-lower alkyl esters, and pharmaceutically acceptable unsubstituted or mono- or di-phenyl or C 1 to C 6 alkyl amides, thereof.
Claim 2
Dependent Claim
394 words
A compound selected from the group having the formulas ##STR24## wherein one of the atoms a and d is nitrogen and the other is carbon, and b and c are carbon, R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 , which may be the same or different, each represent hydrogen, alkyl, halogen, alkenyl, --NO 2 , --NR 1 R 2 , --OR 3 , --S(O) n R 3 ; or alkyl substituted by hydroxy, amino, alkoxy or carbonyl oxygen, n is 0, 1 or 2, R 1 and R 2 , which may be the same or different, each represent hydrogen, alkyl, --CONHR 3 , phenyl or phenyl substituted by alkyl or halogen, or R 1 and R 2 together with the nitrogen atom to which they are attached form a morpholine, piperidine or pyrrolidine ring, R 3 represents hydrogen, alkyl, alkenyl or phenyl, one of G 1 and G 2 is hydrogen and the other is a group E, each E, which may be the same or different, is --COOH, a 5-tetrazolyl group, or a group having the formula ##STR25## R 10 and R 11 are the same or different and are hydrogen, alkyl, alkenyl, phenylalkyl, alkanoyl, or alkoxy carbonyl, and R 10 is hydrogen when R 11 is hydrogen, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 , when they contain carbon, each containing up to 8 carbon atoms, provided that when (i) either a or d is a carbon atom, (ii) E is in a position ortho to the N atom and is --COOH, a 5-tetrazolyl group or an unsubstituted (N-tetrazol-5-yl)carboxamido group, (iii) R 9 is hydrogen, (iv) G 1 is hydrogen and G 2 is a group E, and (v) R 5 , R 6 , R 7 and R 8 are selected from hydrogen, hydroxy, alkyl, halogen, alkenyl, alkoxy or --NR 1 R 2 , then R 4 is not an --OH group para to the N atom, and pharmaceutically acceptable salts, and when E is --COOH, pharmaceutically acceptable lower alkyl esters, 2-(diethylamino)esters and lower alkanoyl-lower alkyl esters, and pharmaceutically acceptable unsubstituted or mono- or di-phenyl or C 1 to C 6 alkyl amides, thereof.
Claim 3
Dependent Claim
53 words
A compound according to claim 1, wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 , when it contains carbon, has up to 4 carbon atoms.
Claim 4
Dependent Claim
44 words
A compound according to claim 1, wherein R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are selected from hydrogen, methoxy, propyl, allyl, methyl, ethyl chlorine, bromine, amino, methylamino, thioethyl, propenyloxy, allyl, phenoxy, ureido and hydroxy.
Claim 5
Dependent Claim
13 words
A compound according to claim 1, wherein R 3 is hydrogen or alkyl.
Claim 6
Dependent Claim
16 words
A compound according to claim 1, wherein G 1 is hydrogen and G 2 is E.
Claim 7
Dependent Claim
16 words
A compound according to claim 1, wherein R 5 is hydrogen and R 8 is alkyl.
Claim 8
Dependent Claim
11 words
A compound according to claim 6, wherein R 8 is propyl.
Claim 9
Dependent Claim
10 words
A compound according to claim 1, wherein d is nitrogen.
Claim 10
Dependent Claim
19 words
A compound according to claim 1, wherein an E group is in a position adjacent to a ring N-atom.
Claim 11
Dependent Claim
16 words
A compound according to claim 1, wherein both E groups are the same and are --COOH.
Claim 12
Dependent Claim
11 words
A compound according to claim 1, wherein R 9 is hydrogen.
Claim 13
Dependent Claim
17 words
A compound according to claim 1, wherein R 4 is para to an N-atom at position d.
Claim 14
Dependent Claim
23 words
A compound according to claim 1, wherein R 4 is hydrogen, halogen, --OR 3 , --SR 3 or --NR 1 R 2 .
Claim 15
Dependent Claim
13 words
A compound according to claim 1, wherein R 4 is other than --OH.
Claim 16
Dependent Claim
11 words
A compound according to claim 1, wherein R 4 is chlorine.
Claim 17
Dependent Claim
24 words
A compound in accordance with claim 1 having the formula ##STR26## and pharmaceutically acceptable salts, and when E is --COOH, lower alkyl esters thereof.
Claim 18
Dependent Claim
11 words
A compound according to claim 16, which is 6 chloro-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid.
Claim 19
Dependent Claim
10 words
A compound according to claim 16, which is disodium 6-chloro-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylate.
Claim 20
Dependent Claim
21 words
A compound according to claim 16, and selected from 6-methoxy-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylthio-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-bromo-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-methyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4,6-dioxo-10-propyl-4H,6H-pyrano[3,2-g]quinoline-3,8-dicarboxylic acid, 4-oxo-6-(prop-2-enyloxy)-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid,
Claim 21
Dependent Claim
42 words
6-dioxo-7-(2-propenyl)-10-propyl-4H,6H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4,6-dioxo-7,10-dipropyl-4H,6H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-chloro-4-oxo-7,10-dipropyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 7-chloro-5-methoxy-4-oxo-4H-pyrano[3,2-g]quinoline-2,9-dicarboxylic acid, 6-chloro-4-oxo-10-(prop-2-enyl)-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylsulphinyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylsulphonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenoxy-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-10-propyl-6-(1-pyrrolidino)-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, N,N'-di-5-tetrazolyl-6-chloro-4-oxo-10-propyl-4H-[3,2-g]pyranoquinoline-2,8-dicarboxamide, 6-chloro-10-methyl-4-oxo-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-dimethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenylamino-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenylthio-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ureido-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-chloro-4-oxo-10-propyl-8-tetrazolyl-4H-pyran[3,2-g]quinoline-2-carboxylic acid, 6-ethoxy-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, and pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
42 words
6-dioxo-7-(2-propenyl)-10-propyl-4H,6H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4,6-dioxo-7,10-dipropyl-4H,6H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-chloro-4-oxo-7,10-dipropyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 7-chloro-5-methoxy-4-oxo-4H-pyrano[3,2-g]quinoline-2,9-dicarboxylic acid, 6-chloro-4-oxo-10-(prop-2-enyl)-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylsulphinyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylsulphonyl-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenoxy-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-10-propyl-6-(1-pyrrolidino)-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, N,N'-di-5-tetrazolyl-6-chloro-4-oxo-10-propyl-4H-[3,2-g]pyranoquinoline-2,8-dicarboxamide, 6-chloro-10-methyl-4-oxo-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-dimethylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenylamino-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 4-oxo-6-phenylthio-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-ureido-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, 6-chloro-4-oxo-10-propyl-8-tetrazolyl-4H-pyran[3,2-g]quinoline-2-carboxylic acid, 6-ethoxy-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, and pharmaceutically acceptable salts thereof.
Claim 23
Dependent Claim
16 words
A compound according to claim 16, which is 6-methylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
24 words
A compound in accordance with claim 1 having the formula ##STR27## and pharmaceutically acceptable salts, and when E is --COOH, lower alkyl esters thereof.
Claim 25
Dependent Claim
16 words
A compound according to claim 21, which is 10-chloro-4-oxo-4H-pyrano[2,3-f]quinoline-2,8-dicarboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
24 words
A compound in accordance with claim 1, having the formula ##STR28## and pharmaceutically acceptable salts, and when E is --COOH, lower alkyl esters thereof.
Claim 27
Dependent Claim
18 words
A compound according to claim 23 and selected from 4-chloro-10-oxo-10H-pyrano[2,3-h]quinoline-2,8-dicarboxylic acid, 10-chloro-1-oxo-1H-pyrano[3,2-f]quinoline-3,8-dicarboxylic acid, and pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim
42 words
A pharmaceutical composition for treatment of a condition involving an antigen-antibody reaction or excess mucous secretion comprising a therapeutically effective amount of a compound according to claim 1, as active ingredient, in combination with a pharmaceutically acceptable inert adjuvant, diluent or carrier.
Claim 29
Dependent Claim
12 words
A composition according to claim 25 in a form suitable for inhalation.
Claim 30
Dependent Claim
19 words
A composition according to claim 25 comprising from 0.001 to 200 mg of active ingredient in unit dosage form.
Claim 31
Dependent Claim
36 words
A method of treatment of a condition involving an antigen-antibody reaction or excess mucous secretion, which comprises administering an effective amount of a compound according to claim 1 to a patient suffering from such a condition.
Claim 32
Dependent Claim
14 words
A method according to claim 28, wherein the condition to be treated is asthma.
Claim 33
Dependent Claim
22 words
A composition in accordance with claims 25, 26 or 27 wherein said compound is 6-methylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, or a pharmaceutically acceptable salt thereof.
Claim 34
Independent Claim
21 words
A method in accordance with claims 28 or 29 wherein said compound is 6-methylamino-4-oxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid, or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1986-12-05 | 1987-06-06 | 1987-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-05 | 1991-06-06 | 1991-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-05 | 1995-06-06 | 1995-12-06 | $7700.00 | Window Closed / Lapsed |