IP Library Granted Patent US 7,019,003
Granted Patent B2
US 7,019,003 · App. 10/469,433 · Granted Mar 28, 2006

Peptide deformylase inhibitors

Assignee: Smithkline Beecham Corporation
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Quick Facts
Patent No.
US 7,019,003
App. No.
10/469,433
Granted
Mar 28, 2006
Kind
B2
Abstract

Novel PDF inhibitors and novel methods for their use are provided.

Claims (189)

1. A compound according to Formula (1):

wherein:

R represents:

C 2-6 alkyl (optionally substituted by alkoxy, halogen, or C 1-3 alkylsulfanyl), C 2-6 alkenyl (optionally substituted by alkoxy, halogen, or C 1-3 alkylsulfanyl), C 2-6 alkynyl (optionally substituted by alkoxy, halogen, or C 1-3 alkylsulfanyl), (CH 2 ) n —C 3-6 , carbocycle (optionally substituted by alkoxy, halogen, or C 1-3 alkylsulfanyl), (CH 2 ) n —R4 {where R4 is phenyl, furan, benzofuran, thiophene, benzothiophene, tetrahydrofuran, tetrahydropyran, dioxane, 1,4-benzodioxane or benzo[1,3]dioxole; R4 is optionally substituted by one or more Cl, Br, I, C 1-3 alkyl (optionally substituted by one to three F) or C 1-2 alkoxy (optionally substituted by one to three F)};

R1 represents:

hydrogen, C 1-6 alkyl (optionally substituted by hydroxy, halogen, amino, guanidino, phenyl, pyridyl, pyrrolyl, indolyl, imidazolyl, furanyl, benzofuranyl, piperidinyl, morpholinyl, quinolinyl, piperazinyl or dimethylaminophenyl) or (CH 2 ) n —C 3-7 carbocycle;

R2 represents:

hydrogen (provided that X is not O), C 1-3 substituted alkyl, C 2-3 substituted alkenyl, C 2-3 substituted alkynyl, (CH 2 ) n —C 3-6 substituted carbocycle, aryl, heteroaryl, heterocyclic, carboxy (provided that X is not NR3 or O) or aminocarbonyl (provided that X is not NR3 or O);

R3 represents:

hydrogen, C 1-3 substituted alkyl, phenyl, or may be taken together with R2 and the nitrogen atom to which they are attached to form an optionally substituted heterocyclic ring which is optionally fused to an aryl, a heteroaryl, or a second heterocyclic ring;

X represents O, NR3 or a covalent bond;

Y represents O, CH 2 or a covalent bond;

n=0-2;

or a salt, solvate, or physiologically functional derivative thereof.

2. A compound as claimed in claim 1 , with the following absolute configuration:

or a salt, solvate or physiologically functional derivative thereof.

3. A compound as claimed in claim 2 , wherein R1=H; or a salt, solvate or physiologically functional derivative thereof.

4. A compound as claimed in claim 1 , wherein X=O; or a salt, solvate, or physiologically functional derivative thereof.

5. A compound according to claim 4 selected from the group consisting of:

N-Butyl-N-(t-butoxycarbonyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-phenoxycarbonyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Isobutyl-N-(t-butoxycarbonyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Isobutyl-N-phenoxycarbonyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Phenethyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Cyclohexylmethyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Benzyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3-pyridin-3-yl-propyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(2-Morpholin-4-yl-ethyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Hydroxy-butyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Amino-butyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Tetrahydro-pyran-4-yl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Methyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3-Aminopropyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(t-Butoxycarbonyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3-Hydroxypropyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-(t-butoxycarbonyl)-N′-{(2S)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-(phenoxycarbonyl)-N′-{(2S)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[2-(4-Dimethylaminophenyl)ethyl]-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxy amino)methyl]-heptanoyl}-hydrazine;

N-(t-Butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Pentyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[2-(1H-Indol-3-yl)-ethyl]-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Isopentyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Cyclohexyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(1-Ethyl-propyl)-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Isopropyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Propyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Ethyl-N-(t-butoxycarbonyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Methoxycarbonyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[1-(3,5-Dimethoxyphenyl)-1-methyl-ethoxy]carbonyl}-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine.

6. A compound as claimed in claim 1 , wherein X=NR3; or a salt, solvate, or physiologically functional derivative thereof.

7. A compound according to claim 6 selected from the group consisting of:

N-Butyl-N-[(4-methylpiperazin-1-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-diphenylaminocarbonyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-(t-butylamino)carbonyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-[(3,5-dimethyl-4,5-dihydro-isoxazol-4-yl)aminocarbonyl]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-[(1-morpholin-4-yl)carbonyl]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-4-phenyl-butanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-hexanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-3-phenyl-propanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-3-(3,4-dichlorophenyl)-propanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3,4-Dichlorophenylaminocarbonyl)-N′-{2-[(formylhydroxy amino)methyl]-heptanoyl}-hydrazine;

N-Phenylaminocarbonyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3,4-Dichlorophenylaminocarbonyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1-Morpholin-4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Methoxyphenyl)aminocarbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,4-Dichlorophenyl)aminocarbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,6-Dichlorophenyl)aminocarbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(4-Methyl-piperazin-1-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(4-Chloro-3-trifluoromethylphenyl)aminocarbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Methyl-phenyl-amino)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine.

8. A compound as claimed in claim 1 , wherein X is a covalent bond; or a salt, solvate, or physiologically functional derivative thereof.

9. A compound according to claim 8 selected from the group consisting of:

N-[(Phenylaminocarbonyl)-carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-{[1-(t-butoxycarbonyl)-piperidin-4-yl]-carbonyl}-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-{[(1-t-butoxycarbonyl)-pyrrolidin-(2S)-yl]carbonyl}-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-{[(1-t-butylaminocarbonyl)piperidin-4-yl]carbonyl}]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-{[(1-t-butylcarbonyl)piperidin-4-yl]carbonyl}]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Butyl-N-[(1,2,3,4-tetrahydro-quinoxalin-2-yl)carbonyl]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(p-Methoxyphenylacetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Phenoxyacetyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(p-Methoxy-phenoxy)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(2,6-Dichlorophenyl-acetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3,4-Dichlorophenylacetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Ethoxycarbonyl)carbonyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(2,4-Dichlorophenylacetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(2,3-Dichlorophenoxyacetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3,4-Dimethoxyphenylacetyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1H-Indol-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Methyl-pyridin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5-Methoxy-benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,3-Dihydro-benzo[1,4]dioxin-(2S)-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinolin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1,2,3,4-Tetrahydro-quinolin-6-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Tetrahydro-furan-(2S)-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Tetrahydro-furan-(2R)-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3-Methyl-benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Pyridin-2-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{3-[3-(4-Methoxybenzyl)-1H-benzoimidazol-2-yl]-propanoyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Pyrimidin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Methyl-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Isoquinolin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5,6,7,8-Tetrahydro-[1,8]naphthyridin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Phenylacetyl)-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1-Methyl-2,5-dioxo-imidazolidin-4-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Phenylacetyl)-N′-{2-[(formylhydroxyamino)methyl]-3-phenyl-propanoyl}-hydrazine;

N-(Phenylacetyl)-N′-{2-[(formylhydroxyamino)methyl]-3-(3,4-dichloro)phenyl-propanoyl}-hydrazine;

N-[(4-Imidazol-1-yl)benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[1-Methyl-5-oxo-2-S-(pyridin-3-yl)-pyrrolidin-(3S)-yl]carbonyl }-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1,2-Dihydro-cinnolin-4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[4-(4-Acetylpiperazin-1-yl)phenoxyacetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Phenylacetyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[1-Benzyl-5-oxo-pyrrolidin-(2S)-yl]-carbonyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[1-Benzyl-5-oxo-pyrrolidin-(2R)-yl]-carbonyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5S)-Benzyl-3,6-dioxo-piperazin-(2S)-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinolin-4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinolin-8-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1,2,3,4-Tetrahydroquinolin-8-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(N″-Acetyl-L-tyrosyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1-Acetyl-1,2,3,4-tetrahydro-quinolin-6-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1H-Benzoimidazol-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-([1-(2-Hydroxyacetyl)-1,2,3,4-tetrahydro-quinolin-6-yl]carbonyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1H-Indol-5-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{4-[Methyl-(4,6-dimethylpyrimidin-2-yl)-amino]benzoyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine);

N-[(1-Benzo[1,3]dioxol-5-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[4-(3,5-Dimethyl-pyrazol-1-yl)methyl]benzoyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[4-(Morpholin-4-yl)-benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[4-Hydroxy-3-(morpholin-4-yl)methyl-benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3-Hydroxy-3-methyl-butanoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Methylamino-benzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1-Isopropyl-1H-benzotriazol-5-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1,2,3,4-Tetrahydro-isoquinolin-(3S)-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5-Chloro-benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[1-(Dimethylaminocarbonylmethyl)-3,4-dihydro-2H-quinolin-6-yl]carbonyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,2-Difluoro-benzo[1,3]dioxol-4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5-Amino-benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(4-Oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-5-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(7-Hydroxy-benzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(6-Methoxy-benzofuran-2-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5-Acetamidobenzofuran-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,3-Dihydro-benzo[1,4]dioxin-6-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3-Amino-4,6-dimethyl-furo[2,3-b]pyridin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Methyl-5,6,7,8-tetrahydro-[1,6]naphthyridin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(6-Fluoro-4H-benzo[1,3]dioxin-8-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(7-Amino-1H-indol-2-yl)carbonyl)]N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1-Methyl-1,2,3,4-tetrahydro-quinolin-6-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N′-[(6,7,9,10,12,13,15,16-Octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Benzo[1,3]dioxol-5-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Pentanoyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Benzoyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Trifluoroacetamido-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3-Hydroxy-naphthalen-2-yl)carbonyl]-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-Phenylacetyl-N′-{2-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Furan-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Methoxybenzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1H-Indol-3-yl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Dimethylaminobenzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(2-Hydroxybenzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Piperidin-4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1,2,5,6-Tetrahydro-pyridin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(7-Methoxy-benzofuran-2-yl)carbonyl-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3-Chloro-4-methoxy-phenyl)acetyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(1H-Pyrrol-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinolin-7-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Pyridin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Chloro-3-methoxy-benzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(3-Methoxybenzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinolin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(5-Methyl-2-phenyl-oxazol4-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(Quinoxalin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Phenylacetyl)-N′-{2-[(formylhydroxyamino)methyl]-4-phenylbutanoyl}-hydrazine;

N-[(3-Methoxy-quinoxalin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,6-Dimethoxypyridin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(N″-Methylsulfonyl)-L-tyrosyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-{[5-Oxo-pyrrolidin-(2S)-yl]carbonyl}-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(4-(Pyrrol-1-yl)benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(4-Acetamidobenzoyl)-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(3-Cyclopentyloxy-4-methoxy)benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-(Phenylacetyl)-N′-{2-[(formylhydroxyamino)methyl]-3-cyclopentyl-propanoyl}-hydrazine;

N-[(7-Methoxy-benzofuran-2-yl)carbonyl]-N′-{2-[(formylhydroxyamino)methyl]-3-cyclopentyl-propanoyl}-hydrazine;

N-[3-(Morpholin-4-yl)propanoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2,3-Dihydro-benzofuran-5-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(4,6-Dimethoxy-pyrimidin-2-yl)benzoyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(2-Trifluoromethyl-5,6,7,8-tetrahydro-naphthyridin-2-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine;

N-[(9H-beta-Carbolin-3-yl)carbonyl]-N′-{(2R)-[(formylhydroxyamino)methyl]-heptanoyl}-hydrazine.

10. A method of treating a bacterial infection by administering to a subject in need of treatment a compound according to claim 1 .

Assignments (2)
CHANGE OF NAME Recorded Jan 8, 2010
From: SMITHKLINE BEECHAM CORPORATION
To: GLAXOSMITHKLINE LLC
Reel/Frame 023750/0387 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2005
From: XIANG, JIA-NING; CHRISTENSEN, SIEGFRIED B., IV; LEE, JINHWA; MERCER, DANIEL J.
To: SMITHKLINE BEECHAM CORPORATION
Reel/Frame 015771/0283 →
Continuity (2)
Provisional Application 6027257000 · Mar 1, 2001
Related Publication 20040087585A1 · May 6, 2004