US5152986A
Expired / Lapsed
US
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Preparation and use of ion exchange resins loaded with quinolonecarboxylic acid derivatives
Assignee: Elanco Animal Health GmbH
•
Filing: 1989-10-24
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Granted: 1992-10-06
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Expires: 2009-10-24
Abstract
Abstract Known antibacterial quinolonecarboxylic acid derivatives such as ciprofloxacin are administered to animals in their food in the form of weak cation exchangers loaded therewith. The taste is much improved and the animals accept the material more readily.
Inventors
- 👤 Peter M. Lange
- 👤 Alfred Mitschker
- 👤 Arundev H. Naik
- 👤 Hubert Rast
- 👤 Martin Scheer
- 👤 Herbert Voege
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 03:55
CPC Classifications
C; C08; C08J; C08J5/00; C08J5/20; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/535; A23; A23K; A23K20/00; A23K20/10; A23K20/116; A61K31/435; A61K31/44; A61K31/47; A61K31/495; A61K31/496; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/58; A61K47/585; A61K9/00; A61K9/0012; A61K9/0053; A61K9/14; A61K9/16; C08J7/00; C08J7/04; C08J7/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
161 words
A weak carboxyl-containing cation exchange resin loaded to the extent of about 10 to 150% of its dry weight with a quinolonecarboxylic acid derivative of the formula ##STR8## in which R 1 represents methyl, ethyl, propyl, isopropyl, cyclopropyl or phenyl; R 2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, R 3 represents a cyclic amino group of the formula ##STR9## wherein R 4 represents hydrogen, alkyl having 1 to 4 carbon atoms, 2-hydroxyethyl, allyl, propargyl, 2-oxopropyl, 3-oxobutyl, phenacyl, formyl, CFCl 2 -S-, CFCl 2 -SO 2 -, CH 3 O-CO-S-, benzyl, 4-aminobenzyl or a radical of the formula ##STR10## R 5 represents hydrogen or methyl, R 6 represents hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyloxymethyl, X represents fluorine, chlorine or nitro and A represents N or C-R 9 , wherein R 9 represents hydrogen, halogen, methyl or nitro or also, together with R 1 , can form a bridge of the structure ##STR11##
Claim 2
Dependent Claim
161 words
A weak carboxyl-containing cation exchange resin loaded to the extent of about 10 to 150% of its dry weight with a quinolonecarboxylic acid derivative of the formula ##STR8## in which R 1 represents methyl, ethyl, propyl, isopropyl, cyclopropyl or phenyl; R 2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, R 3 represents a cyclic amino group of the formula ##STR9## wherein R 4 represents hydrogen, alkyl having 1 to 4 carbon atoms, 2-hydroxyethyl, allyl, propargyl, 2-oxopropyl, 3-oxobutyl, phenacyl, formyl, CFCl 2 -S-, CFCl 2 -SO 2 -, CH 3 O-CO-S-, benzyl, 4-aminobenzyl or a radical of the formula ##STR10## R 5 represents hydrogen or methyl, R 6 represents hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyloxymethyl, X represents fluorine, chlorine or nitro and A represents N or C-R 9 , wherein R 9 represents hydrogen, halogen, methyl or nitro or also, together with R 1 , can form a bridge of the structure ##STR11##
Claim 3
Dependent Claim
35 words
A weak cation exchange resin according to claim 1, in which R 3 represents ##STR12## R 4 represents hydrogen, methyl or ethyl, R 5 represents hydrogen or methyl, and R 6 represents hydrogen or methyl.
Claim 4
Dependent Claim
18 words
A weak cation exchange resin according to claim 2, in which R 5 and R 6 represent hydrogen.
Claim 5
Dependent Claim
17 words
A weak cation exchange resin according to claim 1, in which the quinolone-carboxylic acid derivative is ciprofloxacin.
Claim 6
Dependent Claim
17 words
A weak cation exchange resin according to claim 1, in which the quinolone-carboxylic acid derivative is enrofloxacin.
Claim 7
Dependent Claim
18 words
An animal feed comprising an edible material and a loaded weak cation exchange resin according to claim 1.
Claim 8
Dependent Claim
181 words
In the administration to an animal of a quinolone-carboxylic acid derivative of the formula ##STR13## in which R 1 represents methyl, ethyl, propyl, isopropyl, cyclopropyl or phenyl; R 2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, R 3 represents a cyclic amino group of the formula ##STR14## wherein R 4 represents hydrogen, alkyl having 1 to 4 carbon atoms, 2-hydroxyethyl, allyl, propargyl, 2-oxopropyl, 3-oxobutyl, phenacyl, formyl, CFCl 2 -S-, CFCl 2 -SO 2 -, CH 3 O-CO-S-, benzyl, 4-aminobenzyl or a radical of the formula ##STR15## R 5 represents hydrogen or methyl, R 6 represents hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyloxymethyl, X represents fluorine, chlorine or nitro and A represents N or C-R 9 , wherein R 9 represents hydrogen, halogen, methyl or nitro or also, together with R 1 , can form a bridge of the structure ##STR16## the improvement which comprises administering such derivative loaded to the extent of about 10 to 150% of its dry weight onto a weak carboxylic-containing cation exchange resin and admixed with the animal's feed.
Claim 9
Dependent Claim
181 words
In the administration to an animal of a quinolone-carboxylic acid derivative of the formula ##STR13## in which R 1 represents methyl, ethyl, propyl, isopropyl, cyclopropyl or phenyl; R 2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl, R 3 represents a cyclic amino group of the formula ##STR14## wherein R 4 represents hydrogen, alkyl having 1 to 4 carbon atoms, 2-hydroxyethyl, allyl, propargyl, 2-oxopropyl, 3-oxobutyl, phenacyl, formyl, CFCl 2 -S-, CFCl 2 -SO 2 -, CH 3 O-CO-S-, benzyl, 4-aminobenzyl or a radical of the formula ##STR15## R 5 represents hydrogen or methyl, R 6 represents hydrogen, alkyl having 1 to 4 carbon atoms, phenyl or benzyloxymethyl, X represents fluorine, chlorine or nitro and A represents N or C-R 9 , wherein R 9 represents hydrogen, halogen, methyl or nitro or also, together with R 1 , can form a bridge of the structure ##STR16## the improvement which comprises administering such derivative loaded to the extent of about 10 to 150% of its dry weight onto a weak carboxylic-containing cation exchange resin and admixed with the animal's feed.
Claim 10
Dependent Claim
32 words
The method according to claim 7, in which R 3 represents ##STR17## R 4 represents hydrogen, methyl or ethyl, R 5 represents hydrogen or methyl, and R 6 represents hydrogen or methyl.
Claim 11
Dependent Claim
15 words
The method according to claim 7, in which R 5 and R 6 represent hydrogen.
Claim 12
Dependent Claim
14 words
The method according to claim 7, in which the quinolone-carboxylic acid derivative is ciprofloxacin.
Claim 13
Dependent Claim
14 words
The method according to claim 7, in which the quinolone-carboxylic acid derivative is enrofloxacin.
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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) | 1995-10-06 | 1996-04-06 | 1996-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-10-06 | 2000-04-06 | 2000-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-10-06 | 2004-04-06 | 2004-10-06 | $7700.00 | Window Closed / Lapsed |