Amidine substituted beta - lactam compounds, their preparation and use as antibacterial agents

A compound and substituent technology, applied in the field of new β-lactam compounds, can solve problems that endanger the mid-term availability of existing compounds

Inactive Publication Date: 2014-12-10
AICURIS GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a continuously updated list of a wide range of over 1000 β-lactamases can be found at http: / / www.lahey.org / Studies / ) and other resistance mechanisms seriously jeopardize the mid-term availability of existing compounds in these subclasses

Method used

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  • Amidine substituted beta - lactam compounds, their preparation and use as antibacterial agents
  • Amidine substituted beta - lactam compounds, their preparation and use as antibacterial agents
  • Amidine substituted beta - lactam compounds, their preparation and use as antibacterial agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[1103] (2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-{[2-(4-carbamimidino-3-hydroxyphenoxy)ethoxy]imino}- N-[(3S)-2,2-Dimethyl-4-oxo-1-(sulfoxy)azetidin-3-yl]acetamide

[1104] 1 H NMR (400MHz, DMSO-d 6 ):δ=1.23(s,3H),1.40(s,3H),4.19(m,2H),4.38(m,2H),4.59(d,J=8.0Hz,1H),6.49(s,1H) ,6.57(d,J=8.8Hz,1H,),6.76(s,1H),7.21(br s,2H),7.57(d,J=8.8Hz,1H),9.49(d,J=8.0Hz, 1H).

[1105] MS (ES + ) m / z: C 19 h 24 N 7 o 9 S 2 [M+H] of + Calculated value: 558.11. Experimental value: 558.14.

[1106] HPLC: 98.63%

Embodiment 2

[1108] (2S,3S)-3-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-{[2-(4-formamido-3-hydroxyphenoxy base)ethoxy]imino}acetyl]amino}-2-methyl-4-oxazetidine-1-sulfonic acid

[1109] 1 H NMR (400MHz, DMSO-d 6 ):δ=1.33(d,J=6.2Hz,3H),3.67(m.,1H),4.22(m,2H),4.35(m,2H),4.41(m,1H),6.45(br.s , 1H,), 6.52 (m, 1H), 6.79 (s, 1H), 7.22 (m, 2H), 7.56 (d, J=8.8Hz, 1H), 9.32 (m, 1H).

[1110] MS (ES - ) m / z: C 18 h 20 N 7 o 8 S 2 [M-H] - Calculated value: 526.08. Experimental value: 526.13.

[1111] HPLC: 91.43%

Embodiment 3

[1113] (2S,3S)-3-{[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-({2-[(6-carbamidinopyridin-3-yl )oxy]ethoxy}imino)acetyl]amino}-2-methyl-4-oxazetidine-1-sulfonic acid

[1114] 1 H NMR (400MHz, DMSO-d 6 ):δ=1.35(d,J=6.2Hz,3H),3.66(dd,J=6.0 and 2.5Hz,1H),4.26-4.57(m,5H),6.78(s,1H),7.76(dd, J=8.9 and 2.7Hz, 1H), 8.26(d, J=8.9Hz, 1H), 8.52(d, J=2.3Hz, 1H), 8.95(s, 2H), 9.21-9.49(m, 3H).

[1115] MS (ES - ) m / z: C 17 h 20 N 8 o 7 S 2 [M-H] - Calculated value: 512.09. Experimental value: 512.53.

[1116] HPLC: 96.60%

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Abstract

The present invention relates to novel beta-lactam compounds of formula (I), their preparation and use. In particular, this invention relates to novel beta-lactam compounds which are amidine substituted monobactam derivatives useful as antimicrobial agents and their preparation.

Description

technical field [0001] The present invention relates to novel beta-lactam compounds, their preparation and use. In particular, the present invention relates to novel β-lactam compounds which are amidine substituted monobactam derivatives and their preparation as antimicrobial agents. Background technique [0002] Public health experts and officials consider the emergence and spread of antibiotic-resistant bacteria to be one of the major public health problems of the 21st century. While not a new phenomenon per se, the spread of antibiotic-resistant bacteria has reached unprecedented proportions. Despite the continued emergence of the most resistant isolates in hospital settings, physicians and epidemiologists encounter increased numbers of resistant bacteria in community populations with no previous healthcare exposure. The number of patients dying from untreatable nosocomial infections continues to grow. Treatment options are especially limited for infections due to mult...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/427C07D417/12C07D417/14A61P31/04
CPCC07D417/14C07D417/12A61K31/427A61K31/4178A61K31/433A61K31/4439A61K31/454A61K31/496A61K31/497A61K31/501A61K31/506A61P31/00A61P31/04A61P43/00Y02A50/30A61K45/06
Inventor 布克哈德·克伦克伊瑞斯·维甘德圭多·斯切夫海克·布勒茨-厄斯特黑尔特萨马尔恩德拉·N·迈蒂杰汉吉尔·克汗安德河·雷迪志祥·杨穆斯塔法·赫纳国锋·贾欧·立功宏·梁朱迪·叶川军·高萨比韩·塔贾姆拉希姆·穆罕默德甘谷丽·比斯瓦吉特
Owner AICURIS GMBH & CO KG
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