US 11,040,987 B2Granted

Penam derivatives for treating bacterial infections

AssigneeTenNor Therapeutics Limited

InventorsHuibing Ai, Jun Ding, Shijie He, Yu Liu, Dawei Wan, Huan Wang, Ying Yuan, Qian Zhang, Zhijun Zhuang, Zhenkun Ma

Life of this patent

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Abstract

Novel iron chelating group conjugated penam derivatives described herein show antibacterial activity, and could be used as antibacterial agents or beta-lactamase inhibitors (BLIs) which are of value for application in combination with other antibacterial agents.

Claims14

Dependent claims

A compound having a formula of:

or a stereoisomer, pharmaceutically acceptable salt, solvate, prodrug, or deuterium-exchanged compound thereof,
wherein R1 is hydrogen, a pharmaceutically acceptable salt forming agent, or an ester residue;
Y is independently selected from —S—, —SO—, and —SO2—;
L is one or a combination of groups selected from:
(C1-C8)alkylene, (C3-C8)cycloalkylene containing one to three heteroatoms, arylene, heteroarylene, (C3-C8)heterocycloalkylene, —C(═O)—, —O—, —S(O)n—, wherein n is 0, 1, or 2, —N(R2)—, —C(R3)═C(R4)—, and —C═N—,
wherein R2, R3 and R4 are selected from hydrogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C1-C8)alkyloxyl, aryl, heteroaryl, and (C3-C8)heterocycloalkyl, or R3 and R4 join together to form a bond;
and
Z is an iron chelating moiety selected from
wherein R5, R6 and R7 are independently hydrogen, hydroxyl, halogen, nitrile, nitro, amino, CF3, OCF3, alkyl, alkylamino, alkoxy, aryl, or heteroaryl, or wherein two of R5, R6 and R7 join together to form a 5-8 membered ring.

6 more elements

A compound selected from:

(2S,3R,5R)-3-((E)-(2-(2-chloro-4,5-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-methyl-7-oxo-3-((E)-(2-(2,3,4-trihydroxybenzoyl)hydrazono)methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-chloro-3,4-dihydroxybenzoyl)-2-methylhydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2,5-dichloro-3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-methyl-7-oxo-3-((E)-(2-(3,4,5-trihydroxybenzoyl)hydrazono)methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3,4-dihydroxybenzoyl)-2-methylhydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-bromo-3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-methyl-7-oxo-3-((E)-(2-(2,3,6-trichloro-4,5-dihydroxybenzoyl)hydrazono)methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2,6-dichloro-3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-fluoro-3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3,4-dihydroxy-2-methylbenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(3,4-dihydroxyphenyl)acetyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-((R)-2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-chloro-4,5-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-chloro-3,4-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(3,4-dihydroxyphenyl)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2,5-dihydroxy-3,6-dimethylbenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2,3-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzoyl)pyrrolidine-3-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzoyl)azetidine-3-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzoyl)pyrrolidine-2-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(5-(3,4-dihydroxybenzamido)picolinoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzoyl)piperidine-4-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(2-chloro-3,4-dihydroxybenzamido)-3-hydroxypropanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(2-chloro-3,4-dihydroxybenzamido)-3-phenylpropanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-((2-chloro-3,4-dihydroxybenzamido)methyl)benzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-((3,4-dihydroxybenzamido)methyl)benzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
((2S,3R,5R)-3-((E)-(2-(2-(3,4-dihydroxybenzamido)-3-methylbutanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(2-chloro-3,4-dihydroxybenzamido)-3-methylbutanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzoyl)piperidine-3-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(3,4-dihydroxybenzamido)-3-hydroxypropanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(3,4-dihydroxybenzamido)-3-phenylpropanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(3,4-dihydroxybenzamido)cyclopropanecarbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(1-(2-chloro-3,4-dihydroxybenzamido)cyclopropanecarbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-((3,4-dihydroxybenzoyl)oxy)benzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-((tert-butoxycarbonyl)amino)-3-((2-chloro-3,4-dihydroxybenzoyl)oxy)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3′,4′-dihydroxy-[1,1′-biphenyl]-4-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-((2-chloro-3,4-dihydroxybenzoyl)oxy)benzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(5-(2-chloro-3,4-dihydroxybenzamido)picolinoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(2-chloro-3,4-dihydroxybenzamido)acetyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(2-chloro-3,4-dihydroxybenzamido)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(6-(2-chloro-3,4-dihydroxybenzamido)hexanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-((S)-2-(2-chloro-3,4-dihydroxybenzamido)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-(2-chloro-3,4-dihydroxybenzamido)butanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-(3,4-dihydroxybenzamido)acetyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-((S)-2-(3,4-dihydroxybenzamido)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(4-(3,4-dihydroxybenzamido)butanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(3,4-dihydroxybenzamido)propanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(6-(3,4-dihydroxybenzamido)hexanoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3,4-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-chloro-3,4-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-(3,4-dihydroxyphenyl)-2-oxoethyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2,3-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-methyl-7-oxo-3-(((2-(3,4,5-trihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3,4-dihydroxybenzoyl)-1-methylhydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-chloro-4,5-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-chloro-3,4-dihydroxybenzoyl)-1-methylhydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3,4-dihydroxybenzoyl)-2-methylhydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-methyl-7-oxo-3-(((2-(2,3,4-trihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2,6-dichloro-3,4-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2,5-dichloro-3,4-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-fluoro-3,4-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-(3,4-dihydroxyphenyl)-3-oxopropyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-chloro-4,5-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((((E)-2-(3,4-dihydroxybenzylidene)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-chloro-4,5-dihydroxybenzoyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-(3,4-dihydroxybenzamido)acetyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((3-(3,4-dihydroxybenzamido)pyrrolidine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((4-(3,4-dihydroxybenzoyl)piperazine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(2-(2-chloro-3,4-dihydroxybenzamido)acetyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((((2-(2-chloro-3,4-dihydroxybenzamido)ethyl)carbamoyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((4-(3,4-dihydroxybenzamido)piperidine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((((1-(3,4-dihydroxybenzoyl)pyrrolidin-3-yl)carbamoyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((3-(3,4-dihydroxybenzamido)azetidine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-(2-chloro-3,4-dihydroxyphenyl)-2-oxoethyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-(3,4-dihydroxyphenyl)-2-oxoethyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-chloro-3,4-dihydroxyphenyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-(2,5-dichloro-3,4-dihydroxyphenyl)-2-oxoethyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(3,4-dihydroxyphenyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-((2-chloro-3,4-dihydroxybenzoyl)oxy)ethyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2,5-dichloro-3,4-dihydroxyphenyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-((3,4-dihydroxybenzoyl)oxy)ethyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-((2-chloro-3,4-dihydroxybenzoyl)oxy)ethyl)-4,5-dihydroisoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-chloro-3,4-dihydroxyphenyl)-4,5-dihydroisoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-((2,5-dichloro-3,4-dihydroxybenzamido)methyl)-4,5-dihydroisoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-((3,4-dihydroxybenzoyl)oxy)ethyl)-4,5-dihydroisoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-((2-chloro-3,4-dihydroxybenzamido)methyl)-4,5-dihydroisoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(3,4-dihydroxybenzoyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((3,4-dihydroxybenzoyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-chloro-3,4-dihydroxybenzoyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3S,5R)-3-(((3,4-dihydroxyphenyl)amino)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-((2-(2-chloro-3,4-dihydroxybenzamido)ethoxy)imino)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-((4-(2-chloro-3,4-dihydroxybenzamido)phenoxy)imino)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(2-chloro-3,4-dihydroxybenzoyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(2-bromo-4,5-dihydroxybenzoyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(3,4-dihydroxyphenyl)-5-methylisoxazole-4-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(2-chloro-3,4-dihydroxyphenyl)isoxazole-5-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-(3-(3,4-dihydroxyphenyl)isoxazole-5-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-((4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(2-((4S,5R)-2-(3,4-dihydroxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonyl)hydrazono)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-(2,3-dihydroxyphenyl)isoxazole-5-carbonyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-(2,3-dihydroxyphenyl)-4,5-dihydroisoxazole-5-carbonyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((4-(2-chloro-3,4-dihydroxybenzoyl)piperazine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((3-(2-chloro-3,4-dihydroxybenzamido)azetidine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-(2-chloro-3,4-dihydroxyphenyl)-4,5-dihydroisoxazole-5-carbonyl)hydrazine-1-carbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-(3-(2-chloro-3,4-dihydroxyphenyl)-4,5-dihydroisoxazole-5-carbonyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(((2-((4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonyl)hydrazinecarbonyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((((3,4-dihydroxyphenethyl)carbamoyl)oxy)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-(5-(3,4-dihydroxybenzoyl)isoxazol-3-yl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3S,5R)-3-((4-((E)-(2-(2-chloro-3,4-dihydroxybenzoyl)hydrazono)methyl)-1H-imidazol-1-yl)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
(2S,3R,5R)-3-((E)-(((1-(2-chloro-3,4-dihydroxybenzoyl)piperidin-4-yl)oxy)imino)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide;
and
(2S,3R,5R)-3-((E)-(((1-(2-chloro-3,4-dihydroxybenzoyl)azetidin-3-yl)oxy)imino)methyl)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide.

111 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/001,764Filed 25 Aug 2020 · us provisional application
Priority: 11 Sep 2019
Published: US 2021/0070774 A111 Mar 2021
Granted: 22 Jun 2021
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 499/87
Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:…
A61K 31/43
Condensed with heterocyclic ring systems: compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring…
A61K 31/431
Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula [IMAGE…: containing…
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole

Family

Application62/898,598Us provisional application · filed 11 Sep 2019
US 2021/0070774 A1Pre-grant publication · published 11 Mar 2021
US 11,040,987 B2This patent

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

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Abstract

Facts

Application

17/001,764Filed 25 Aug 2020 · us provisional application

Priority

11 Sep 2019

Published

US 2021/0070774 A111 Mar 2021

Granted

22 Jun 2021

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 499/87
Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:…
A61K 31/43
Condensed with heterocyclic ring systems: compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring…
A61K 31/431
Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula [IMAGE…: containing…
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole