US4904675A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Phamacologically active 5-carboxy-2-(5-tetrazolyl) pyridines
Assignee: Haleon CH SARL
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Filing: 1988-02-10
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Granted: 1990-02-27
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Expires: 2008-02-10
Abstract
Abstract Compounds of the formula I ##STR1## wherein the groups A, R 1 , R 2 and R 3 are as defined in the specification, exhibit valuable pharmacological properties, especially as antifibrotic agents. They are prepared by methods known per se.
Inventors
- 👤 Eva Winter-Mihaly
- 👤 Christian Borel
- 👤 Andre J. Weith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 02:56
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D213/80; A; A61; A61P; A61P1/00; A61P1/16; A61P11/00; A61P13/00; A61P13/02; A61P15/00; A61P17/00; A61P3/00; A61P9/00; A61P9/10; C07D213/81; C07D217/00; C07D217/22; C07D217/26; C07D401/00; C07D401/02; C07D401/04; C07D413/00; C07D413/02; C07D413/04; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
164 words
A member selected from the group consisting of (a) a compound of formula ##STR6## wherein A represents 5-tetrazolyl which is unsubstituted or is substituted in the 2-position by a member selected from the group consisting of (1) C 1 -C 20 alkyl, (2) amino-lower alkyl, (3) mono-lower alkylamino-lower alkyl, (4) di-lower alkylamino-lower alkyl, (5) carboxy-lower alkyl, (6) lower alkoxycarbonyl-lower alkyl, (7) aryl-lower alkyl, (8) hydroxy-lower alkyl, (9) lower alkanoyloxy-lower alkyl, (10) lower alkoxy-lower alkyl, (11) hydroxy-lower alkoxymethyl, (12) lower alkanoyloxy-lower alkoxymethyl, (13) lower alkoxy-lower alkoxymethyl, (14) 1-alkoxycarbonyl-1-lower alkoxy-methyl, (15) 3-phthalidyl, (16) lower alkyl-3-phthalidyl, (17) lower alkoxy-3-phthalidyl, (18) halogen-3-phthalidyl, (19) lower alkoxycarbonyloxy-lower alkyl and (20) lower alkanoyl; R 1 represents carboxy or a pharmaceutically acceptable ester group thereof; R 2 represents hydrogen or a member selected from the group consisting of lower alkyl, cycloalkyl, aryl-lower alkyl, heteroaryl-lower alkyl and aryl each of which members can be unsubstituted or substituted; and R 3 represents hydrogen; (b) a tautomer thereof and (c) a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
164 words
A member selected from the group consisting of (a) a compound of formula ##STR6## wherein A represents 5-tetrazolyl which is unsubstituted or is substituted in the 2-position by a member selected from the group consisting of (1) C 1 -C 20 alkyl, (2) amino-lower alkyl, (3) mono-lower alkylamino-lower alkyl, (4) di-lower alkylamino-lower alkyl, (5) carboxy-lower alkyl, (6) lower alkoxycarbonyl-lower alkyl, (7) aryl-lower alkyl, (8) hydroxy-lower alkyl, (9) lower alkanoyloxy-lower alkyl, (10) lower alkoxy-lower alkyl, (11) hydroxy-lower alkoxymethyl, (12) lower alkanoyloxy-lower alkoxymethyl, (13) lower alkoxy-lower alkoxymethyl, (14) 1-alkoxycarbonyl-1-lower alkoxy-methyl, (15) 3-phthalidyl, (16) lower alkyl-3-phthalidyl, (17) lower alkoxy-3-phthalidyl, (18) halogen-3-phthalidyl, (19) lower alkoxycarbonyloxy-lower alkyl and (20) lower alkanoyl; R 1 represents carboxy or a pharmaceutically acceptable ester group thereof; R 2 represents hydrogen or a member selected from the group consisting of lower alkyl, cycloalkyl, aryl-lower alkyl, heteroaryl-lower alkyl and aryl each of which members can be unsubstituted or substituted; and R 3 represents hydrogen; (b) a tautomer thereof and (c) a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
97 words
A compound according to claim 1, wherein R 2 represents hydrogen or a member selected from the group consisting of lower alkyl, cycloalkyl, aryl-lower alkyl, heteroaryl-lower alkyl and aryl each of which members can be unsubstituted or substituted by amino, lower alkylamino, di-lower alkylamino, N-piperidino, N-morpholino, N-thiomorpholino, N-piperazino, 4-(lower alkyl or lower alkanoyl)-N-piperazino, lower alkoxy, C 3 -C 14 -alkoxy wherein the alkyl chain is interrupted by 1 to 5 oxy groups, or C 3 -C 14 -alkylamino wherein the alkyl chain is interrupted by 1 to 5 oxy and/or imino groups; and R 3 represents hydrogen.
Claim 4
Dependent Claim
81 words
A compound according to claim 1, wherein A represents 5-tetrazolyl, 2-lower alkanoyl-5-tetrazolyl or 2-(1-lower alkoxycarbonyl-1-lower alkoxy-methyl)-5-tetrazolyl; R 1 represents carboxy, C 1 -C 20 -alkoxycarbonyl or 1-lower alkoxycarbonyl-1-lower alkoxy-methoxycarbonyl; R 2 represents hydrogen, lower alkyl, C 5 -C 7 -cycloalkyl, phenyl-lower alkyl or phenyl, wherein in the latter two radicals, phenyl is unsubstituted or substituted by lower alkyl, hydroxy, lower alkoxy and/or halogen; and R 3 represents hydrogen; a tautomer of said compound or a pharmaceutically acceptable salt of said compound.
Claim 5
Dependent Claim
60 words
A compound according to claim 1, wherein A represents 5-tetrazolyl, 2-lower alkanoyl-5-tetrazolyl or 2-(1-lower alkoxycarbonyl-1-lower alkoxy-methyl)-5-tetrazolyl; R 1 represents carboxy, C 1 -C 20 -alkoxycarbonyl or 1-lower alkoxycarbonyl-1-lower alkoxy-methoxycarbonyl; R 2 represents hydrogen, lower alkyl, C 5 -C 7 -cycloalkyl or phenyl; and R 3 represents hydrogen; a tautomer of said compound or a pharmaceutically acceptable salt of said compound.
Claim 6
Dependent Claim
20 words
A compound according to claim 1, wherein R 2 and R 3 represent hydrogen; or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
65 words
A compound according to claim 1, wherein A represents 5-tetrazolyl, R 1 represents carboxy or lower alkoxycarbonyl, R 2 is hydrogen, lower alkyl, cycloalkyl, phenyl-lower alkyl or phenyl, wherein in the latter two radicals, phenyl is unsubstituted or substituted by lower alkyl, hydroxy, lower alkoxy and/or halogen, and R 3 represents hydrogen; a tautomer of said compound or a pharmaceutically acceptable salt of said compound.
Claim 8
Dependent Claim
35 words
A compound according to claim 1, wherein A represents 5-tetrazolyl, R 1 is carboxy or lower alkoxycarbonyl, R 2 is hydrogen or lower alkyl and R 3 represents hydrogen; or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
10 words
A compound according to claim 1, said compound being 5-carboxy-2-(5-tetrazolyl)-pyridine.
Claim 10
Dependent Claim
11 words
A compound according to claim 1, said compound being hexadecyl 2-(5-tetrazolyl)pyridine-5-carboxylate.
Claim 11
Dependent Claim
39 words
A pharmaceutical composition comprising an amount of a compound, a tautomer or a salt according to claim 1 effective for the treatment of diseases responsive to collagen proline-4-hydroxylase inhibition in mammals together with at least one pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
37 words
A method of treating diseases responsive to collagen proline-4-hydroxylase inhibition in mammals comprising the administration to a mammal in need thereof of a therapeutically effective amount of a compound, a tautomer or salt according to claim 1.
Claim 13
Dependent Claim
30 words
A method of decreasing collagen synthesis in a mammal comprising the administration to said mammal of an effective amount of a compound, a tautomer or salt according to claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-02-26 | 1993-08-28 | 1994-02-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-26 | 1997-08-28 | 1998-02-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-26 | 2001-08-28 | 2002-02-27 | $7700.00 | Window Closed / Lapsed |