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US 2003/0171587 A1Published application
Antimicrobial 2-pyridones, their compositions and uses
AssigneeThe Procter & Gamble Company
InventorsBenoit Ledoussal, Sean M. Flaim
Life of this patent
Estimating the term…
Abstract
Compounds having the general structure: 1 are effective antimicrobial agents.
Claims22
A compound having a structure according to Formula (I)
- 108
- wherein:
- (A) (1) R1 is selected from C3 to about C6 cycloalkyl, C4 to about C6 heterocycloalkyl, C1 to about C6 alkyl, C2 to about C6 alkene, a 6-membered aryl, and a 6-membered heteroaryl;
- (2) R2 is hydrogen;
- (3) R3 is selected from hydrogen and hydroxy;
- (4) R5 is selected from hydrogen, hydroxy, amino, halo, C1 to about C6 alkyl, C2 to about C6 alkene, and C1 to about C6 alkoxy;
- (5) R6 is selected from hydrogen, hydroxy, aminocarbonyl, cyano, C1 to about C4 alkyl, and C2 to about C4 alkene;
- all such alkyl and alkene moieties being unsubstituted or substituted with from 1 to about 3 fluoro, or in the case of methyl or ethyl, optionally substituted with one hydroxy or one amino moiety;
- (6) R7 is selected from
- 109
- wherein
- (a) R9 is (i) amino which is attached to a ring carbon of R7 which is not adjacent to the ring nitrogen of R7, the amino being unsubstituted or substituted with one or two C1 to about C3 alkyl;
- or (ii) aminoalkyl which is attached to any ring carbon of R7 and is C1 to about C3 alkyl substituted with one amino, the amino being unsubstituted or substituted with one or two C1 to about C3 alkyl;
- and
- (b) R10 represents the moieties on R7 other than R9 and each R10 is independently selected from hydrogen, C1 to about C4 alkyl, C2 to about C6 alkene, and a C3 to about C6 fused or spirocycle alkyl ring;
- all alkyl, alkene and cyclic R10 moieties being unsubstituted or substituted with one hydroxy or with from 1 to about 3 fluoro moieties;
- and
- (7) R8 is selected from hydrogen, halo, C1 to about C6 alkoxy, C1 to about C6 alkylthio, C1 to about C6 alkyl and C2 to about C6 alkene;
- or
- (B) R8 and R1 can join to form a 6-membered heterocyclic ring, where R2, R3, R5, R6 and R7 are as described in (A);
- or an optical isomer, diastereomer or enantiomer thereof;
- or a pharmaceutically-acceptable salt, hydrate, or biohydrolyzable ester, amide or imide thereof.
19 more elements
A compound having a structure according to the following Formula (B):
- 111
- wherein
- (1) R2is hydrogen;
- (2) R3 is selected from hydrogen and hydroxy;
- (3) R5 is selected from hydrogen, hydroxy, amino, halo, C1 to about C6 alkyl, C2 to about C6 alkene, and C1 to about C6 alkoxy;
- (4) R6 is selected from hydrogen, hydroxy, aminocarbonyl, cyano, C1 to about C4 alkyl, and C2 to about C4 alkene;
- all such alkyl and alkene moieties being unsubstituted or substituted with from 1 to about 3 fluoro, or in the case of methyl or ethyl, optionally substituted with one hydroxy or one amino moiety;
- (5) R7 is selected from
- 112
- wherein
- (a) R9 is (i) amino which is attached to a ring carbon of R7 which is not adjacent to the ring nitrogen of R7, the amino being unsubstituted or substituted with one or two C1 to about C3 alkyl;
- or (ii) aminoalkyl which is attached to any ring carbon of R7 and is C1 to about C3 alkyl substituted with one amino, the amino being unsubstituted or substituted with one or two C1 to about C3 alkyl;
- and
- (b) R10 represents the moieties on R7 other than R9 and each R10 is independently selected from hydrogen, C1 to about C4 alkyl, C2 to about C6 alkene, and a C3 to about C6 fused or spirocycle alkyl ring;
- all alkyl, alkene, and cyclic R10 moieties being unsubstituted or substituted with one hydroxy or with from 1 to about 3 fluoro moieties;
- (6) Y is selected substituted or unsubstituted —C— or —N—, or Y is —O—;
- (7) Z is selected from —O—, —S—, substituted or unsubstituted —C—, and substituted or unsubstituted —N—;
- and
- (8) R3 and R13′ are independently selected from hydrogen and C1 to about C6 alkyl;
- or an optical isomer, diastereomer or enantiomer thereof;
- a pharmaceutically-acceptable salt, hydrate, or biohydrolyzable ester, amide or imide thereof.
18 more elements
A method of using a compound having a structure according to Formula (C)
- 113
- wherein R14 is selected from methoxy or methyl;
- R15 is selected from ethyl or cyclopropyl;
- in the process of making a compound according to Formula (I)
- 114
2 more elements
Dependencies are inferred from the claim text.