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US4556709A Expired / Lapsed US ⏱️ 0.0 years remaining

2-Amino-8-cyclopropyl-5-oxo-5,8-dihydro-pyrido[2,3-d]-pyrimidine-6-carboxylic acid compounds

Assignee: Bayer AG
•
Filing: 1982-07-26
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Granted: 1985-12-03
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Expires: 2002-07-26
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Abstract

Abstract The invention relates to 2-amino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid compounds, processes for their preparation and their use as antibacterial agents, and also as feed additives.

Inventors

  • 👤 Klaus Grohe
  • 👤 Hans-Joachim Zeiler
  • 👤 Karl G. Metzger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 13:30
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; A; A61; A61P; A61P31/00; A61P31/04; C07D239/46; C07D239/47; C07D471/00; C07D471/02; C07D471/04

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 276 words
A compound of the formula ##STR45## or a therapeutically useful acid-addition salt thereof, in which R 1 is alkyl having 1 to 12 carbon atoms, optionally substituted by alkoxy having 1 to 4 carbon atoms or dialkylamino having 1 to 3 carbon atoms per alkyl radical; or alkenyl having 2 to 12 carbon atoms, R 2 is hydrogen; alkyl having 1 to 12 carbon atoms or hydroxyalkyl having 1 to 12 carbon atoms; R 1 and R 2 taken together with the nitrogen atom on which they are substituents and, optionally, with a further hetero atom selected from oxygen, sulphur or NR 4 , form a 5- to 7-membered ring which is optionally substituted on a carbon atom by 1 to 4 C 1 -C 2 -alkyl groups, R 4 is hydrogen; C 1 to C 6 alkyl, optionally substituted by hydroxy, alkoxy, alkylmercapto or dialkylamino group with 1 to 3 carbon atoms per alkyl radical or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy moiety; cycloalkyl with 3 to 7 carbon atoms; phenylalkyl which has up to 4 carbon atoms in the aliphatic part and is unsubstituted or substituted in the phenyl part by halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkylmercapto, phenoxy, phenylmercapto, trifluoromethyl, nitro, cyano or carboxylic acid ester with 1 to 4 carbon atoms in the alcohol part; phenyl or pyridyl, pyrimidyl, thiazolyl or benzthiazolyl or alkoxycarbonyl which has 1 to 4 carbon atoms in the alkoxy moiety; or alkanoyl with 1 to 6 carbon atoms; phenyl-carbonyl; or aminosulphonyl; and R 3 is hydrogen or alkyl having up to 3 carbon atoms.
Claim 2
Dependent Claim 276 words
A compound of the formula ##STR45## or a therapeutically useful acid-addition salt thereof, in which R 1 is alkyl having 1 to 12 carbon atoms, optionally substituted by alkoxy having 1 to 4 carbon atoms or dialkylamino having 1 to 3 carbon atoms per alkyl radical; or alkenyl having 2 to 12 carbon atoms, R 2 is hydrogen; alkyl having 1 to 12 carbon atoms or hydroxyalkyl having 1 to 12 carbon atoms; R 1 and R 2 taken together with the nitrogen atom on which they are substituents and, optionally, with a further hetero atom selected from oxygen, sulphur or NR 4 , form a 5- to 7-membered ring which is optionally substituted on a carbon atom by 1 to 4 C 1 -C 2 -alkyl groups, R 4 is hydrogen; C 1 to C 6 alkyl, optionally substituted by hydroxy, alkoxy, alkylmercapto or dialkylamino group with 1 to 3 carbon atoms per alkyl radical or alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy moiety; cycloalkyl with 3 to 7 carbon atoms; phenylalkyl which has up to 4 carbon atoms in the aliphatic part and is unsubstituted or substituted in the phenyl part by halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -alkylmercapto, phenoxy, phenylmercapto, trifluoromethyl, nitro, cyano or carboxylic acid ester with 1 to 4 carbon atoms in the alcohol part; phenyl or pyridyl, pyrimidyl, thiazolyl or benzthiazolyl or alkoxycarbonyl which has 1 to 4 carbon atoms in the alkoxy moiety; or alkanoyl with 1 to 6 carbon atoms; phenyl-carbonyl; or aminosulphonyl; and R 3 is hydrogen or alkyl having up to 3 carbon atoms.
Claim 3
Dependent Claim 52 words
A compound according to claim 1 in which the 5-membered to 7-membered ring formed by R 1 and R 2 together with the nitrogen atom on which they are substituents includes as a ring member, oxygen, sulphur, or NR 4 in which R 4 has the same meaning as in claim 1.
Claim 4
Dependent Claim 20 words
A compound according to claim 1 or 2 in which R 4 denotes a pyridine, pyrimidine, thiazole or benzthiazole radical.
Claim 5
Dependent Claim 10 words
A compound according to claim 1 which is 2-(4-methylpiperazino)-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 6
Dependent Claim 10 words
A compound according to claim 1 which is 2-pyrrolidino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 7
Dependent Claim 10 words
A compound according to claim 1 which is 2-morpholino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 8
Dependent Claim 10 words
A compound according to claim 1 which is 2-piperidino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 9
Dependent Claim 10 words
A compound according to claim 1 which is 2-piperazino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 10
Dependent Claim 11 words
A compound according to claim 1 which is 2-(4-β-hydroxyethyl-piperazino)-8-cyclopropyl-5-oxo-5,8-dihydropyrido [2,3-d]pyrimidine-6-carboxylic acid.
Claim 11
Dependent Claim 10 words
A compound according to claim 1 which is 2-dimethylamino-8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.
Claim 12
Dependent Claim 11 words
A compound according to claim 1 which is 2-4-formyl-piperazino 8-cyclopropyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.

References Cited (Backward Citations)

US3770742A Cited
US3673184A Cited
US3950338A Cited
US3887557A Cited
US4017622A Cited
US3992380A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-12-02 1989-06-03 1989-12-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-12-02 1993-06-03 1993-12-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-12-02 1997-06-03 1997-12-03 $7700.00 Window Closed / Lapsed

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