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US4539326A
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5-Oxo-5H-(1)benzopyrano(2,3-b)pyridine derivatives, their production and use as anti-inflammatory agents
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1983-07-05
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Granted: 1985-09-03
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Expires: 2003-07-05
Abstract
Abstract The present invention relates to novel 5-oxo-5H-[1]benzopyrano[2,3-b]pyridine derivatives useful for effective medicines for the treatment of various connective tissue diseases such as chronic rheumatoid arthritis and varieties of inflammatory diseases caused by immunoreaction, which have the following formula: ##STR1## wherein R is the same or different and represents hydrogen, alkyl, alkoxy, nitro, hydroxyl, acyl, hydroxyalkyl, halogen with the proviso that m is 1,2 or 3, or a tetramethylene (--(CH 2 ) 4 --) or butadienylene (--CH═CH--CH═CH--) group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring with the proviso that m is 1; n is 1 or 2, or a physiologically acceptable salt or ester thereof.
Inventors
- 👤 Akira Nohara
- 👤 Seiji Kuzuna
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 09:28
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
82 words
A compound of the formula: ##STR6## wherein R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl-CO, C 1-4 -hydroxyalkyl or halogen where m is 1,2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof.
Claim 2
Dependent Claim
82 words
A compound of the formula: ##STR6## wherein R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl-CO, C 1-4 -hydroxyalkyl or halogen where m is 1,2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof.
Claim 3
Dependent Claim
143 words
A process for producing a compound of the formula: ##STR7## where R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl-CO, C 1-4 -hydroxyalkyl or halogen where m is 1,2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof, which comprises reacting a compound of the formula: ##STR8## wherein R and m have the same meaning as defined above, with a compound of the formula: R.sub.1 OOC--(CH.sub.2).sub.n --COCH.sub.2 COOR.sub.1 wherein R 1 is alkyl and n has the same meaning as defined above, followed by subjecting the resultant reaction product to a hydrolysis reaction, if necessary.
Claim 4
Dependent Claim
143 words
A process for producing a compound of the formula: ##STR7## where R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl-CO, C 1-4 -hydroxyalkyl or halogen where m is 1,2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof, which comprises reacting a compound of the formula: ##STR8## wherein R and m have the same meaning as defined above, with a compound of the formula: R.sub.1 OOC--(CH.sub.2).sub.n --COCH.sub.2 COOR.sub.1 wherein R 1 is alkyl and n has the same meaning as defined above, followed by subjecting the resultant reaction product to a hydrolysis reaction, if necessary.
Claim 5
Dependent Claim
110 words
A pharmaceutical composition for the treatment of connective tissue and inflammatory diseases which contains an amount effective for such treatment of a compound of the formula: ##STR9## wherein R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl CO, C 1-4 -hydroxyalkyl or halogen where m is 1, 2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof and a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
110 words
A pharmaceutical composition for the treatment of connective tissue and inflammatory diseases which contains an amount effective for such treatment of a compound of the formula: ##STR9## wherein R is the same or different and represents hydrogen, C 1-6 -alkyl, C 1-4 -alkoxy, nitro, hydroxyl, C 1-3 -alkyl CO, C 1-4 -hydroxyalkyl or halogen where m is 1, 2 or 3, or a --(CH 2 ) 4 -- or --CH═CH--CH═CH-- group which, in conjunction with two adjacent carbon atoms on the ring, forms a six-membered ring where m is 1; and wherein n is 1 or 2, or a physiologically acceptable salt or ester thereof and a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
11 words
A compound as claimed in claim 1, wherein m is 1.
Claim 8
Dependent Claim
11 words
A compound as claimed in claim 1, wherein m is 2.
Claim 9
Dependent Claim
11 words
A compound as claimed in claim 1, wherein n is 1.
Claim 10
Dependent Claim
13 words
A compound as claimed in claim 1, wherein R is C 1-6 -alkyl.
Claim 11
Dependent Claim
13 words
A compound as claimed in claim 1, wherein R is C 1-4 -hydroxyalkyl.
Claim 12
Dependent Claim
11 words
A compound as claimed in claim 1, wherein R is halogen.
Claim 13
Dependent Claim
20 words
A compound as claimed in claim 1, wherein R is C 1-6 -alkyl, m is 1 and n is 1.
Claim 14
Dependent Claim
20 words
A compound as claimed in claim 1, wherein R is C 1-4 -hydroxyalkyl, m is 1 and n is 1.
Claim 15
Dependent Claim
18 words
A compound as claimed in claim 1, wherein R is halogen, m is 1 and n is 1.
Claim 16
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-ethyl-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 17
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is ethyl(7-ethy-3-ethoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 18
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is disodium(7-ethyl-3-carboxylato-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 19
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 20
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-chlor-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 21
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is ethyl(7-chlor-3-ethoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 22
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is disodium(7-chlor-3-carboxylato-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl]acetate.
Claim 23
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-isopropyl-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 24
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7,9-dimethyl-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 25
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is ethyl(7-nitro-3-ethoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 26
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is ethyl(7-(1-hydroxyethyl)-3-ethoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 27
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-t-butyl-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 28
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-methoxy-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 29
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is methyl(7-hydroxy-3-methoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
Claim 30
Dependent Claim
12 words
A compound as claimed in claim 1, wherein the compound is ethyl(7-acetyl-3-ethoxycarbonyl-5-oxo-5H-[1]benzopyrano[2,3-b]pyridin-2-yl)acetate.
References Cited (Backward Citations)
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US3931199A
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US4143042A
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US4255576A
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US4299963A
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US4302463A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-02 | 1989-03-04 | 1989-09-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-02 | 1993-03-04 | 1993-09-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-02 | 1997-03-04 | 1997-09-03 | $7700.00 | Window Closed / Lapsed |