US 9,403,758 B2Granted

Antibacterial agents

AssigneeAchaogen, Inc.

InventorsBrian D. Patterson, Qing Lu, James Bradley Aggen, Paola Dozzo, Ramesh Annasaheb Kasar, Martin Sheringham Linsell, Timothy Robert Kane, Micah James Gliedt, Darin James Hildebrandt, Glenn A. McEnroe, Frederick Cohen

Life of this patent

Estimating the term…

Abstract

Antibacterial compounds of formula (I) are provided: as well as stereoisomers and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

Claims18

Dependent claims

A compound of formula I:

or a stereoisomer or pharmaceutically acceptable salt thereof, wherein
A is selected from the group consisting of:
(a) substituted C1-C6 alkyl, wherein at least one substituent is hydroxy;
and
(b) substituted C3-C6 cycloalkyl, wherein at least one substituent is selected from hydroxy and hydroxyalkyl;
G is selected from the group consisting of:
(a) —C≡C—;
(b) —CH═CH—C≡C—;
(c) —C≡C—CH═CH—;
(d) —C≡C—C≡C—;
(g) phenyl;
D is selected from the group consisting of:
R1 and R2 are each independently selected from hydrogen and methyl;
and
E is —C(CH3)2SCH3, —C(CH3)2S(O)CH3, —C(CH3)2S(O)2CH3, or —C(O)NHCH3.

12 more elements

A compound selected from the group consisting of:

N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 2);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 3);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 4);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methyl sulfonyl)-1-oxobutan-2-yl)-4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 5);
N—((S)-3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl)-6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)-2-naphthamide (Compound 6);
N—((S)-3-amino-1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl)-6-(((trans)-2-(hydroxymethyl)cyclopropyl)ethynyl)benzo[b]thiophene-2-carboxamide (Compound 7);
N1-hydroxy-2-(4-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 8);
N-hydroxy-4-(4-(((trans)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 9);
N-hydroxy-4-(4-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 35);
N-hydroxy-4-(4-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 36);
N-hydroxy-4-(4-(((1R,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 37);
N-hydroxy-4-(4-(((1S,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 38);
N-hydroxy-4-(4-(5-hydroxypenta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 39);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 40);
N-hydroxy-4-(4-(5-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 41);
N-hydroxy-4-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 42);
4-(4-(5,6-dihydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 43);
4-(4-(6,7-dihydroxyhepta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 44);
N-hydroxy-4-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 45);
N-hydroxy-4-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 46);
N-hydroxy-4-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 47);
N-hydroxy-4-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 48);
N-hydroxy-4-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 49);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 50);
N-hydroxy-4-(4-(4-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 51);
N-hydroxy-4-(4-(4-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 52);
N-hydroxy-4-(4-(4-(((1R,2S)-2-(hydroxymethyl)cyclopropyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 53);
N-hydroxy-4-(4-(4-(((1S,2R)-2-(hydroxymethyl)cyclopropyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 54);
N-hydroxy-4-(4-(4-(3-hydroxyprop-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 55);
N-hydroxy-4-(4-(4-(4-hydroxybut-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 56);
N-hydroxy-4-(4-(4-(3-hydroxybut-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 57);
N-hydroxy-4-(4-(4-(4-hydroxy-3-methylbut-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 58);
4-(4-(4-(3,4-dihydroxybut-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 59);
4-(4-(4-(4,5-dihydroxypent-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 60);
N-hydroxy-4-(4-(4-((3-hydroxycyclobutyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 61);
N-hydroxy-4-(4-(4-((3-(hydroxymethyl)cyclobutyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 62);
N-hydroxy-4-(4-(4-((3-(hydroxymethyl)cyclopentyl)ethynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 63);
N-hydroxy-4-(4-(4-(4-hydroxy-3-methoxybut-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 64);
N-hydroxy-4-(4-(4-(5-hydroxy-4-methoxypent-1-ynyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 65);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 66);
N-hydroxy-4-(4-(4-((2S)-2-(hydroxymethyl)cyclopropyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 67);
N-hydroxy-4-(4-(4-((2R)-2-(hydroxymethyl)cyclopropyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 68);
N-hydroxy-4-(4-(4-((2S)-2-(hydroxymethyl)cyclopropyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 69);
N-hydroxy-4-(4-(4-((2R)-2-(hydroxymethyl)cyclopropyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 70);
N-hydroxy-4-(4-(4-(hydroxymethyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 71);
N-hydroxy-4-(4-(4-(2-hydroxyethyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 72);
N-hydroxy-4-(4-(4-(1-hydroxyethyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 73);
N-hydroxy-4-(4-(4-(1-hydroxypropan-2-yl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 74);
4-(4-(4-(1,2-dihydroxyethyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 75);
4-(4-(4-(2,3-dihydroxypropyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 76);
N-hydroxy-4-(4-(4-(3-hydroxycyclobutyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 77);
N-hydroxy-4-(4-(4-(3-(hydroxymethyl)cyclobutyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 78);
N-hydroxy-4-(4-(4-(3-(hydroxymethyl)cyclopentyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 79);
N-hydroxy-4-(4-(4-(2-hydroxy-1-methoxyethyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 80);
N-hydroxy-4-(4-(4-(3-hydroxy-2-methoxypropyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 81);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 82);
N-hydroxy-4-(4-(4-((E)-2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 83);
N-hydroxy-4-(4-(4-((E)-2-((1S,2R)-2-(hydroxymethyl)cyclopropyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 84);
N-hydroxy-4-(4-(4-((E)-2-((1S,2S)-2-(hydroxymethyl)cyclopropyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 85);
N-hydroxy-4-(4-(4-((E)-2-((1R,2R)-2-(hydroxymethyl)cyclopropyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 86);
(E)-N-hydroxy-4-(4-(4-(3-hydroxyprop-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 87);
(E)-N-hydroxy-4-(4-(4-(4-hydroxybut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 88);
(E)-N-hydroxy-4-(4-(4-(3-hydroxybut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 89);
(E)-N-hydroxy-4-(4-(4-(4-hydroxy-3-methylbut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 90);
(E)-4-(4-(4-(3,4-dihydroxybut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 91);
(E)-4-(4-(4-(4,5-dihydroxypent-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 92);
(E)-N-hydroxy-4-(4-(4-(2-(3-hydroxycyclobutyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 93);
(E)-N-hydroxy-4-(4-(4-(2-(3-(hydroxymethyl)cyclobutyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 94);
(E)-N-hydroxy-4-(4-(4-(2-(3-(hydroxymethyl)cyclopentyl)vinyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 95);
(E)-N-hydroxy-4-(4-(4-(4-hydroxy-3-methoxybut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 96);
(E)-N-hydroxy-4-(4-(4-(5-hydroxy-4-methoxypent-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 97);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 98);
N-hydroxy-4-(4-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 99);
N-hydroxy-4-(4-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 100);
N-hydroxy-4-(4-(((1R,2S)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 101);
N-hydroxy-4-(4-(((1S,2R)-2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 102);
N-hydroxy-4-(4-(5-hydroxypenta-1,3-diynyl)phenyl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 103);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 104);
N-hydroxy-4-(4-(5-hydroxyhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 105);
N-hydroxy-4-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 106);
4-(4-(5,6-dihydroxyhexa-1,3-diynyl)phenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 107);
4-(4-(6,7-dihydroxyhepta-1,3-diynyl)phenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 108);
N-hydroxy-4-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 109);
N-hydroxy-4-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 110);
N-hydroxy-4-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 111);
N-hydroxy-4-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 112);
N-hydroxy-4-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 113);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 114);
N-hydroxy-4-(4′-(((1S,2S)-2-(hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 115);
N-hydroxy-4-(4′-(((1R,2R)-2-(hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 116);
N-hydroxy-4-(4′-(((1R,2S)-2-(hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 117);
N-hydroxy-4-(4′-(((1S,2R)-2-(hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 118);
N-hydroxy-4-(4′-(3-hydroxyprop-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 119);
N-hydroxy-4-(4′-(4-hydroxybut-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 120);
N-hydroxy-4-(4′-(3-hydroxybut-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 121);
N-hydroxy-4-(4′-(4-hydroxy-3-methylbut-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 122);
4-(4′-(3,4-dihydroxybut-1-ynyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methyl sulfonyl)butanamide (Compound 123);
4-(4′-(4,5-dihydroxypent-1-ynyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 124);
N-hydroxy-4-(4′-((3-hydroxycyclobutyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 125);
N-hydroxy-4-(4′-((3-(hydroxymethyl)cyclobutyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 126);
N-hydroxy-4-(4′-((3-(hydroxymethyl)cyclopentyl)ethynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 127);
N-hydroxy-4-(4′-(4-hydroxy-3-methoxybut-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 128);
N-hydroxy-4-(4′-(5-hydroxy-4-methoxypent-1-ynyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 129);
N-hydroxy-4-(4-(6-hydroxyhexa-1,3-diynyl)phenyl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 130);
N-hydroxy-4-(4′-((2 S)-2-(hydroxymethyl)cyclopropyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 131);
N-hydroxy-4-(4′-((2R)-2-(hydroxymethyl)cyclopropyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 132);
N-hydroxy-4-(4′-((2 S)-2-(hydroxymethyl)cyclopropyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 133);
N-hydroxy-4-(4′-((2R)-2-(hydroxymethyl)cyclopropyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 134);
N-hydroxy-4-(4′-(hydroxymethyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 135);
N-hydroxy-4-(4′-(2-hydroxyethyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 136);
N-hydroxy-4-(4′-(1-hydroxyethyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 137);
N-hydroxy-4-(4′-(1-hydroxypropan-2-yl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 138);
4-(4′-(1,2-dihydroxyethyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 139);
4-(4′-(2,3-dihydroxypropyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 140);
N-hydroxy-4-(4′-(3-hydroxycyclobutyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 141);
N-hydroxy-4-(4′-(3-(hydroxymethyl)cyclobutyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 142);
N-hydroxy-4-(4′-(3-(hydroxymethyl)cyclopentyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 143);
N-hydroxy-4-(4′-(2-hydroxy-1-methoxyethyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 144);
N-hydroxy-4-(4′-(3-hydroxy-2-methoxypropyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 145);
N-hydroxy-4-(4′-((E)-2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 146);
N-hydroxy-4-(4′-((E)-2-((1S,2R)-2-(hydroxymethyl)cyclopropyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 147);
N-hydroxy-4-(4′-((E)-2-((1S,2S)-2-(hydroxymethyl)cyclopropyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 148);
N-hydroxy-4-(4′-((E)-2-((1R,2R)-2-(hydroxymethyl)cyclopropyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 149);
(E)-N-hydroxy-4-(4′-(3-hydroxyprop-1-enyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 150);
(E)-N-hydroxy-4-(4′-(4-hydroxybut-1-enyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 151);
(E)-N-hydroxy-4-(4′-(3-hydroxybut-1-enyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 152);
(E)-N-hydroxy-4-(4′-(4-hydroxy-3-methylbut-1-enyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 153);
(E)-4-(4′-(3,4-dihydroxybut-1-enyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 154);
(E)-4-(4′-(4,5-dihydroxypent-1-enyl)biphenyl-4-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide (Compound 155);
(E)-N-hydroxy-4-(4′-(2-(3-hydroxycyclobutyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 156);
(E)-N-hydroxy-4-(4′-(2-(3-(hydroxymethyl)cyclobutyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 157);
(E)-N-hydroxy-4-(4′-(2-(3-(hydroxymethyl)cyclopentyl)vinyl)biphenyl-4-yl)-2-methyl-2-(methylsulfonyl)butanamide (Compound 158);
(E)-N-hydroxy-4-(4-(4-(4-hydroxy-3-methoxybut-1-enyl)phenyl)-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methyl sulfonyl)butanamide (Compound 159);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-(5-hydroxypenta-1,3-diynyl)benzamide (Compound 160);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-(6-hydroxyhexa-1,3-diynyl)benzamide (Compound 161);
4-(5,6-dihydroxyhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 162);
4-(6,7-dihydroxyhepta-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 163);
4-(6-hydroxy-5-methylhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 164);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-((3-hydroxycyclobutyl)buta-1,3-diynyl)benzamide (Compound 165);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzamide (Compound 166);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)benzamide (Compound 167);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methyl sulfonyl)-1-oxobutan-2-yl)-4-(5-hydroxyhexa-1,3-diynyl)benzamide (Compound 160);
4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 169);
4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 170);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)-4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 171);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(5-hydroxypenta-1,3-diynyl)benzamide (Compound 172);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(6-hydroxyhexa-1,3-diynyl)benzamide (Compound 173);
4-(5,6-dihydroxyhexa-1,3-diynyl)-N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)benzamide (Compound 174);
4-(6,7-dihydroxyhepta-1,3-diynyl)-N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)benzamide (Compound 175);
4-(6-hydroxy-5-methylhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylsulfonyl)-1-oxobutan-2-yl)benzamide (Compound 176);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-((3-hydroxycyclobutyl)buta-1,3-diynyl)benzamide (Compound 177);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzamide (Compound 178);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)benzamide (Compound 179);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-(5-hydroxyhexa-1,3-diynyl)benzamide (Compound 180);
4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)benzamide (Compound 181);
4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)benzamide (Compound 182);
N-((2R)-1-(hydroxyamino)-3-methyl-3-(methylsulfinyl)-1-oxobutan-2-yl)-4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 183);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 184);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(5-hydroxypenta-1,3-diynyl)benzamide (Compound 185);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(6-hydroxyhexa-1,3-diynyl)benzamide (Compound 186);
4-(5,6-dihydroxyhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)benzamide (Compound 187);
4-(6,7-dihydroxyhepta-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)benzamide (Compound 188);
4-(6-hydroxy-5-methylhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)benzamide (Compound 189);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-((3-hydroxycyclobutyl)buta-1,3-diynyl)benzamide (Compound 190);
(R)—N-(1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzamide (Compound 191);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)benzamide (Compound 192);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-(5-hydroxyhexa-1,3-diynyl)benzamide (Compound 193);
4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)benzamide (Compound 194);
4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)benzamide (Compound 195);
N—((R)-1-(hydroxyamino)-3-methyl-3-(methylthio)-1-oxobutan-2-yl)-4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamide (Compound 196);
N1-hydroxy-2-(4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 197);
N1-hydroxy-2-(4-(5-hydroxypenta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 198);
N1-hydroxy-2-(4-(6-hydroxyhexa-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 199);
N1-hydroxy-2-(4-(5-hydroxyhexa-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 200);
2-(4-(5,6-dihydroxyhexa-1,3-diynyl)benzamido)-N1-hydroxy-N3-methylmalonamide (Compound 201);
2-(4-(6,7-dihydroxyhepta-1,3-diynyl)benzamido)-N1-hydroxy-N3-methylmalonamide (Compound 202);
N1-hydroxy-2-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 203);
N1-hydroxy-2-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 204);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 205);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 206);
N1-hydroxy-2-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 207);
N1-hydroxy-2-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)benzamido)-N3-methylmalonamide (Compound 208);
N1-hydroxy-2-(4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 209);
N1-hydroxy-2-(4-(5-hydroxypenta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 210);
N1-hydroxy-2-(4-(6-hydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 211);
N1-hydroxy-2-(4-(5-hydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 212);
2-(4-(5,6-dihydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N1-hydroxy-N3-methylmalonamide (Compound 213);
2-(4-(6,7-dihydroxyhepta-1,3-diynyl)-N-methylbenzamido)-N1-hydroxy-N3-methylmalonamide (Compound 214);
N1-hydroxy-2-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 215);
N1-hydroxy-2-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 216);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 217);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 218);
N1-hydroxy-2-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 219);
N1-hydroxy-2-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-N-methylbenzamido)-N3-methylmalonamide (Compound 220);
N1-hydroxy-2-(4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 221);
N1-hydroxy-2-(4-(5-hydroxypenta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 222);
N1-hydroxy-2-(4-(6-hydroxyhexa-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 223);
N1-hydroxy-2-(4-(5-hydroxyhexa-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 224);
2-(4-(5,6-dihydroxyhexa-1,3-diynyl)benzamido)-N1-hydroxy-N3,2-dimethylmalonamide (Compound 225);
2-(4-(6,7-dihydroxyhepta-1,3-diynyl)benzamido)-N1-hydroxy-N3,2-dimethylmalonamide (Compound 226);
N1-hydroxy-2-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 227);
N1-hydroxy-2-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 228);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 229);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 230);
N1-hydroxy-2-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 231);
N1-hydroxy-2-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)benzamido)-N3,2-dimethylmalonamide (Compound 232);
N1-hydroxy-2-(4-((2-(hydroxymethyl)cyclopropyl)buta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 233);
N1-hydroxy-2-(4-(5-hydroxypenta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 234);
N1-hydroxy-2-(4-(6-hydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 235);
N1-hydroxy-2-(4-(5-hydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 236);
2-(4-(5,6-dihydroxyhexa-1,3-diynyl)-N-methylbenzamido)-N1-hydroxy-N3,2-dimethylmalonamide (Compound 237);
2-(4-(6,7-dihydroxyhepta-1,3-diynyl)-N-methylbenzamido)-N1-hydroxy-N3,2-dimethylmalonamide (Compound 280);
N1-hydroxy-2-(4-(6-hydroxy-5-methylhexa-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 239);
N1-hydroxy-2-(4-((3-hydroxycyclobutyl)buta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 240);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclobutyl)buta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 241);
N1-hydroxy-2-(4-((3-(hydroxymethyl)cyclopentyl)buta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 242);
N1-hydroxy-2-(4-(6-hydroxy-5-methoxyhexa-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 243);
and
N1-hydroxy-2-(4-(7-hydroxy-6-methoxyhepta-1,3-diynyl)-N-methylbenzamido)-N3,2-dimethylmalonamide (Compound 244).

216 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/537,048Filed 10 Nov 2014 · continuation
Priority: 10 May 2012
Published: US 2016/0016895 A121 Jan 2016
Granted: 2 Aug 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 259/06
Without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids: having carbon atoms of hydroxamic groups bound to…
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07C 313/04
Sulfinic acids; Derivatives thereof: sulfinic acids; Esters thereof
C07C 313/12
Sulfenic acids; Esters thereof: having sulfur atoms of sulfenic groups bound to acyclic carbon atoms

Family

Application61/645,439Us provisional application · filed 10 May 2012
PCT/US2013/040571Parent of this continuation · filed 10 May 2013
US 2016/0016895 A1Pre-grant publication · published 21 Jan 2016
US 9,403,758 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

Facts

Application

14/537,048Filed 10 Nov 2014 · continuation

Priority

10 May 2012

Published

US 2016/0016895 A121 Jan 2016

Granted

2 Aug 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 259/06
Without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids: having carbon atoms of hydroxamic groups bound to…
A61P 31/04
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antibacterial agents
C07C 313/04
Sulfinic acids; Derivatives thereof: sulfinic acids; Esters thereof
C07C 313/12
Sulfenic acids; Esters thereof: having sulfur atoms of sulfenic groups bound to acyclic carbon atoms