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US 2007/0191394 A1Published application
Antibacterial agents
AssigneeWarner-Lambert Company
InventorsRichard John Sciotti, Jeremy Tyson Starr, Christopher Richardson, Gordon William Rewcastle, Huifen Chen, Brian Desmond Palmer, Hamish Scott Sutherland, Julie Ann Spicer
Life of this patent
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Abstract
Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.
Claims13
A compound of the formula
- or a pharmaceutically acceptable salt thereof, wherein:
- X1 is CH2, NH, or O;
- X2 is absent, or is
- (CH2)x′, NH, O,
- wherein are points of attachment, or
- is a tether 2, 3 or 4 atoms in length, selected from
- wherein R is H or (C1-C6)alkyl, and
- wherein are points of attachment and x′ is an integer from 1 to 3;
- Y is N, C—H, C—F, or C—OMe;
- Ris H or halo;
- R2 is (C3-C6)cycloalkyl,
- (CH2)x-aryl,
- (CH2)x-heterocyclo, or
- (CH2)x-heteroaryl,
- wherein x is 0, 1, or 2;
- R3is H,
- (C1-C6)alkyl,
- (C3-C6)cycloalkyl,
- aryl,
- heterocyclo,
- heteroaryl,
- C(O)NRaRb,
- C(O)Ra,
- CO2Ra,
- C(O)C(O)NRaRb,
- NO2,
- SO2Ra,
- SO2NRaRb,
- C(Rc)═NORa,
- C(Rc)═NRa,
- wherein indicates the point of attachment,
- wherein indicates the point of attachment, and wherein
- Ra is H,
- (C1-C6)alkyl,
- (C3-C6)cycloalkyl,
- (CH2)y-aryl,
- (CH2)y-heterocyclo, or
- (CH2)y-heteroaryl,
- wherein y is 0, 1, or 2;
- Rb is H,
- (C1-C6)alkyl,
- (C3-C6)cycloalkyl,
- aryl,
- heterocyclo, or
- heteroaryl;
- Rc is H,
- (C1-C6)alkyl,
- (C3-C6)cycloalkyl,
- aryl,
- heterocyclo, or
- heteroaryl;
- and
- R4 is (C1-C6)alkyl, (C1-C6alkyl)-O—(C1-C6alkyl), cyclopropyl, CH2-cyclopropyl, or cyclobutyl.
50 more elements
A compound selected from the group consisting of:
- (7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-carbamic acid ethyl ester;
- 1-ethyl-3-(7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- [7-(2-dimethylamino-pyrimidin-5-yl)-imidazo[1,2-a]pyridin-2-yl]-carbamic acid ethyl ester;
- 1-[7-(2-dimethylamino-pyrimidin-5-yl)-imidazo[1 ,2-a]pyridin-2-yl]-3-ethyl-urea;
- [7-(6-methoxy-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-carbamic acid ethyl ester;
- 1-ethyl-3-[7-(6-methoxy-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(2-methoxy-pyrimidin-5-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- (7-pyridin-3-yl-imidazo[1,2-c]pyrimidin-2-yl)-carbamic acid ethyl esters;
- 1-ethyl-3-{7-[6-(2-morpholin-4-yl-ethoxy)-pyridin-3-yl]-imidazo[1,2-a]pyridin-2-yl}-urea;
- 1-ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-(5-formyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 2-(3-ethyl-ureido)-7-pyridin-3-yl-imidazo[1,2-a]pyridine-5-carboxylic acid methyl ester;
- 1-ethyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-[7-(3,5-dimethyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-[7-(1-benzyl-1H-pyrazol-4-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-ethyl-3-{7-[6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-imidazo[1,2-a]pyridin-2yl}-urea;
- 1-ethyl-3-[7-(1-methyl-1H-pyrazol-4-yl)-imidazo[1 ,2-a]pyridin-2-yl]-urea;
- 1-[7-(2,4-dimethoxy-pyrimidin-5-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 4-[2-(3-ethyl-ureido)-imidazo[1,2-a]pyridin-7-yl]-3,5-dimethyl-pyrazole-1-carboxylic acid tert-butyl ester;
- 1-ethyl-3-[7-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-(3-chloro-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-3-ethyl-urea;
- 1-[3-chloro-7-(2-dimethylamino-pyrimidin-5-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 2-(3-ethyl-ureido)-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester;
- 2-(3-ethyl-ureido)-imidazo[1,2-a]pyridine-7-carboxylic acid amide;
- 1-ethyl-3-[7-(5-methyl-2H-[1,2,4]triazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-[7-(1,5-dimethyl-1H-[1,2,4]triazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea and 1-[7-(2,5-dimethyl-2H-[1,2,4]triazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-ethyl-3-[7-(5-methyl-[1,2,4]oxadiazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[5-(1-methyl-1H-pyrazol-4-yl)-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl]-urea;
- 2-(3-ethyl-ureido)-imidazo[1,2-a]pyridine-7-carboxylic acid;
- 1-[7-(3,5-dimethyl-1H-pyrazol-4-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-ethyl-3-[7-(piperidine-1-carbonyl)-imidazo[1 ,2-a]pyridin-2-yl]-urea;
- 1-cyclopropyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-cyclopropylmethyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-propyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-isopropyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-3-(2,2,2-trifluoro-ethyl)-urea;
- 1-(2-methoxy-ethyl)-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-cyclobutyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-[7-(6-amino-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- N-(7-acetylimidazo[1,2-a]pyridin-2-yl)-N-ethylurea;
- 1-ethyl-3-[7-(5-methyl-[1,3,4]oxadiazol-2-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- {4-[2-(3-ethyl-ureido)-imidazo[1,2-a]pyridin-7-yl]-pyridin-2-yl}-carbamic acid tert-butyl ester;
- 1-ethyl-3-[7-(2H-pyrazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-(7-[1,2,3]thiadiazol-4-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-[7-(5-isopropyl-[1,2,4]oxadiazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- {4-[2-(3-ethyl-ureido)-imidazo[1,2-a]pyridin-7-yl]-pyridin-2-yl}-carbamic acid
- tert-butyl ester;
- compound with 1-[7-(2-amino-pyridin-4-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-ethyl-3-[7-(morpholine-4-carbonyl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[5-(3-methyl-[1,2,4]oxadiazol-5-yl)-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(6-fluoro-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(6-methyl-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 7-(2-dimethylamino-pyrimidin-5-yl)-2-(3-ethyl-ureido)-imidazo[1,2-a]pyridine-5-carboxylic acid ethylamide, and
- 1-[7-(2-dimethylamino-pyrimidin-5-yl)-5-pyrimidin-2-yl-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea.
55 more elements
A compound selected from the group consisting of:
- 1-ethyl-3-(7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-[7-(6-methoxy-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(2-methoxy-pyrimidin-5-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-(5-hydroxymethyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-(5-formyl-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 2-(3-ethyl-ureido)-7-pyridin-3-yl-imidazo[1,2-a]pyridine-5-carboxylic acid methyl ester;
- 1-ethyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-[5-( 1-methyl-1H-pyrazol-4-yl)-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-propyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-cyclobutyl-3-(7-pyrimidin-5-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-[7-(6-amino-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea;
- 1-ethyl-3-[7-(2H-pyrazol-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-(7-[1,2,3]thiadiazol-4-yl-imidazo[1,2-a]pyridin-2-yl)-urea;
- 1-ethyl-3-[7-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[5-(3-methyl-[1,2,4]oxadiazol-5-yl)-7-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl]-urea;
- 1-ethyl-3-[7-(6-fluoro-pyridin-3-yl)-imidazo[1,2-a]pyridin-2-yl]-urea;
- 7-(2-dimethylamino-pyrimidin-5-yl)-2-(3-ethyl-ureido)-imidazo[1,2-a]pyridine-5-carboxylic acid ethylamide, and;
- 1-[7-(2-dimethylamino-pyrimidin-5-yl)-5-pyrimidin-2-yl-imidazo[1,2-a]pyridin-2-yl]-3-ethyl-urea.
15 more elements
Dependencies are inferred from the claim text.