# US 8,148,540 B2 · Heterocyclic compounds, their preparation and their use as medicaments, in particular as anti-bacterial agents

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- Number: US 8,148,540 B2
- Document ID: US8148540B2
- Status: Granted
- Kind: B2
- Application number: 11/810,981
- Filed: 2007-06-07
- Published: 2007-12-27
- Granted: 2012-04-03
- Earliest claimed: 2001-06-08
- Assignees: AstraZeneca AB
- Inventors: Joseph Aszodi; Maxime Lampilas; Branislav Musicki; David Alan Rowlands; Pascal Colette
- Web page: https://patentgrep.com/patent/US8148540B2

## CPC

- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- A61P 31/04: Antibacterial agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 217/22: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D 217/26: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 471/04: Ortho-condensed systems
- C07D 471/08: Bridged systems
- C07D 491/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to new heterocyclic compounds of general formula (I), and their salts with a base or an acid: The invention also relates to a process for the preparation of these compounds as well as their use as medicaments, in particular as anti-bacterial agents.

## Claims

### Claim 1

A compound having a formula selected from the group consisting of:
wherein
a) R′1 is selected from the group consisting of hydrogen, —CN, protected —COOH, —COOR″, —(CH2)n′—R′5, —CONR6R7 and —C(═NR6)NHR7, R″ is selected from the group consisting of alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl, —CH2-alkenyl of 3 to 9 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms, the aryl and aralkyl optionally substituted on the aromatic ring by at least one member of the group consisting of —NO2, protected OH, protected —NH2, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms and halogen;
R′5 is selected from the group consisting of protected —OH, —CN, protected —NH2, —CO —NR6R7, protected —COOH, —COO′R″, —OR″, —OCOH, —OCOR″, OCOOR″, OCONH2, OCONHR″, protected NHR″, NHCOR″, NHSO2R″, —NHCOOR″, —NH—CO—NHR″ and —NH—CONH2;
n′ is 1 or 2,
R6 and R7 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, optionally substituted by pyridyl, aryl of 6 to 10 carbon atoms and aralkyl of 7 to 11 carbon atoms;
R′4 and R3 together form heterocyclic aromatic of 5 to 6 vertices with 1 to 4 heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen optionally substituted by at least one R′;
R′ is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms optionally substituted by at least one oxo, halo, nitro, cyano, alkenyl of 2 to 6 carbon atoms, halogen, amino, —OH, protected —OH, —OR, —NHCOH, —NHCOR″, —NHCOOR″, —COOH, —COOR″, —C(C6H5)3 and —CH2—CH2—S(O)m—R″;
m is 0, 1 or 2;
R′2 is selected from the group consisting of hydrogen, halogen, R″, —S(O)mR″, —OR″, —NHCOH, —NHCOR″, —NHCOOR″ and —NHSO2R″;
m is 0, 1 or 2;
n is 1 or 2;
—ZH is selected from the group consisting of —(CH2)n″—OH, —NHR′8—(CH2)n″— and —O—NHR8;
n″ is 0 or 1,
R′8 is selected from the group consisting of hydrogen, R″, protected —OH, —OR″, —Y′, —OY′, —Y′1, —OY1′, —Y′2, —OY′2, —Y′3, —OCH2—CH2—S(O)m—R″, —SiRaRbRc and —OSiRaRbRc; Ra, Rb and Rc are individually alkyl of 1 to 6 carbon atoms or aryl 6 to 10 carbon atoms;
m is defined above with the proviso that ZH is not —(CH2)n″—OH when R′1 is —(CH2)n′—R′5;
Y′ is selected from the group consisting of —COH, —COR″, —COOR″, —CONH2, —CONHR″, —CONHSO2R″, —CH2COOR″, protected —CH2tetrazol, —CH2SO2R″, —CH2PO(OR″)2, protected —CONHOH, protected CH2COOH, protected CH2CONHOH, protected CH2SO3H, protected —CH2PO(OR), protected
—CH2PO(R)(OH) and protected —CH2PO(OH)2;
Y′1 is selected from the group consisting of —SO2R″, —SO2NHCOH,
—SO2NHCOR″, —SO2NHCOOR″, —SO2NHCONH2, —SO2NHCONHR″ and protected —SO3H;
Y′2 is selected from the group consisting of —PO(OR″)2, protected —PO(OH)2, protected —PO(OH)(OR) and protected —PO(OH)(R);
Y′3 is selected from the group consisting of protected tetrazol, tetrazol substituted by R″, protected squarate, protected —NH-tetrazole, protected —NR″-tetrazol, protected —NH—, —NR″-tetrazole substituted by R″, —NHSO2R″ and —NSO2R″;
A is hydrogen or a nitrogen protective group,
and R9 is a leaving group and their acid addition salts.

### Claim 2 (depends on 1)

A compound of the formula
wherein R′1, R′2, R′4, n, A and R′8 have the definition of claim 1 and their acid addition salts.

### Claim 3 (depends on 1)

A compound of the formula
wherein —ZH, R′1, R′2, R′4 and n have the definition of claim 1.

### Claim 4 (depends on 1)

A compound of a formula selected from the group consisting of
wherein R′1, R′2, R′4, A and n are as defined in claim 1 and their acid addition salts.