134575-17-0

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Biochem/physiol Actions

CP-101537 is a MMP inhibitor, candidate drug for myocardial infarction therapy, and antibacterial.

InChI:InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-8-6-4-11-5-7(6)8/h6-8,11H,4-5H2,1-3H3,(H,12,13)/t6-,7+,8?

Upstream product

• 174456-77-0 [(1α,5α,6α)-3-aza-bicyclo[3.1.0]hexane]-6-carboxylic acid ethyl ester 
• 146726-10-5 3-benzyl 6-ethyl (1α,5α,6α)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate 
• 151860-15-0 (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane 
• 151860-16-1 (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane 
• 151860-17-2 (1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane 
• 134575-15-8 (1α,5α,6α)-3-(benzyloxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid 
• 134575-06-7 ethyl (1α,5α,6α)-3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione-6-carboxylate 
• 134575-14-7 benzyl (1α,5α,6α)-6-hydroxymethyl-3-azabicyclo[3.1.0]hexan-3-ylcarboxylate 
• 134575-07-8 (1α,5α,6α)-6-hydroxymethyl-3-benzyl-3-aza-bicyclo[3.1.0]hexane 
• 134575-13-6 (1α,5α,6α)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane 
• 146726-08-1 (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester 
• 185559-52-8 (1α,5α,6α)-3-N-benzyl-6-[t-butoxycarbonylamino]-3-aza-bicyclo[3.1.0]hexane 

Downstream Products

• 256369-34-3 (1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane ditosylate salt 
• 134575-66-9 7-([1α,5α,6α]-6-tert-Butoxycarbonylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid,ethyl ester 
• 1003884-14-7 [(1α,5α,6α)-3-(4-chlorobenzyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester 
• 1003884-20-5 [(1α,5α,6α)-3-(2-fluorobenzoyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester 
• 146836-84-2 trovafloxacin mesylate 
• 146726-08-1 (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester 
• 504438-27-1 4-[(1α,5α,6α)-6-(N-t-butoxycarbonyl)amino-3-azabicyclo[3.1.0]hexan-3-yl]nitrobenzene 
• 504438-19-1 [(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid tert-butyl ester 
• 392660-03-6 Methanesulfonic acid (R)-3-{4-[(1S,5R,6S)-6-(tert-butoxycarbonyl-methyl-amino)-3-aza-bicyclo[3.1.0]hex-3-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-ylmethyl ester 
• 392660-06-9 ((1S,5R,6S)-3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-methyl-carbamic acid tert-butyl ester 
• 392660-04-7 {(1S,5R,6S)-3-[4-((R)-5-Azidomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester 
• 392660-01-4 [(1S,5R,6S)-3-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-yl]-methyl-carbamic acid tert-butyl ester 
• 392660-05-8 {(1S,5R,6S)-3-[4-((S)-5-Aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester 
• 392660-02-5 {(1S,5R,6S)-3-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-3-aza-bicyclo[3.1.0]hex-6-yl}-methyl-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Mechanisms of trovafloxacin hepatotoxicity: Studies of a model cyclopropylamine-containing system

The mechanism for the hepatotoxicity of trovafloxacin remains unresolved. Trovafloxacin contains a cyclopropylamine moiety which has a potential to be oxidized to reactive intermediate(s) although other putative elements may exist. In this study, a drug model of trovafloxacin containing the cyclopropylamine substructure was synthesized. Chemical oxidation of the drug model by K3Fe(CN)6 and NaClO revealed that both oxidants oxidize this drug model to a reactive α,β-unsaturated aldehyde, 11. The structure of 11 was fully elucidated by LC/MS/MS and NMR analysis. These results suggested that P450s with heme-iron center and myeloperoxidase generating hypochlorous acid in the presence of chloride ion are capable of bioactivating the cyclopropylamine moiety of trovafloxacin. This deleterious metabolism may lead to eventual hepatotoxicity.

Synthesis of azabicyclo[3.1.0]amine analogues of anacardic acid as potent antibacterial agents

Azabicyclo[3.1.0]amine analogues of anacardic acid (16a, 16b, 18a, 18b, 19 and 19b) were synthesized from anacardic acid and tested for their antibacterial activity against Gram positive and Gram negative bacteria. Most of the compounds are having potency at par with ampicillin and inferior with other standard drugs.

INDOLE DERIVATIVES USEFUL AS CCR2 ANTAGONISTS

Disclosed are the CCR2 antagonists of Formula I: I or pharmaceutically acceptable salt thereof wherein R7, A, X, B, and n are defined herein. Also disclosed are pharmaceutical compositions containing the compounds, methods of treatment using the compounds

PYRROLE CARBOXYLIC ACID DERIVATIVES AS ANTIBACTERIAL AGENTS

The present invention provides DNA Gyrase and/or Topo IV inhibitors of Formula (I), which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed by gram positive, gram negative and anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Pseudomonus spp., Acenetobacter spp., Mvraxalla spp., Chlamydia spp., Mycoplasma spp., Legionella spp., Mycobacterium spp., Helicobacter, Clostridium spp., Bacteroides spp., Cotynebacterium, Bacillus spp., Enterobactericeae (E. coli, Klebsiella spp., Proteus spp., etc.) or any combination thereof. Also provided, are processes for preparing compounds disclosed herein, pharmaceutical compositions containing compounds disclosed herein, and methods of treating bacterial infections.

PYRROLE CARBOXYLIC ACID DERIVATIVES AS ANTIBACTERIAL AGENTS

The present invention provides DNA Gyrase and/or Topo IV inhibitors of formula I, which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed by gram positive, gram negative and anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Pseudomonus spp., Acenetobacter spp., Muraxalla spp., Chlamydia spp., Mycoplasma spp., Legionella spp., Mycobacterium spp., Helicobacter, Clostridium spp., Bacteroides spp., Cotyne bacterium, Bacillus spp., Enterobactericeae (E.coli, Klebsiella spp., Proteus spp.,etc.) or any combination thereof Also provided, are processes for preparing compounds disclosed herein, pharmaceutical compositions containing compounds disclosed herein, and methods of treating bacterial infections

6-(3-AZA-BICYCLO[3.1.0]HEX-3-YL)-2-PHENYL-PYRIMIDINES

The present invention relates to 6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidine derivatives and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals.

Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base, N, N-diethylacetamidine

The simple and in-expensive amidine base, N.N-diethylacetamidine, has been prepared and utilized in the construction of bicyclic hetero compound, 4 and employed for further reduction of amidic carbonyl groups of 4 by using NaBH 4I2-THF condition which is an efficient and commercially viable method to prepare 5 towards the synthesis of amino moiety I, in Trovafloxacin 2 an antibacterial agent.

Discovery of conformationally rigid 3-azabicyclo[3.1.0]hexane-derived dipeptidyl peptidase-IV inhibitors

The induction of conformationally restricted N-(aryl or heteroaryl)-3-azabicyclo[3.1.0]hexane derivatives at P2 region of compounds of 2-cyanopyrrolidine class was explored to develop novel DPP-IV inhibitors. The synthesis, structure-activity r

AZABICYCLIC MUSCARINIC RECEPTOR ANTAGONISTS

The present invention generally relates to muscarinic receptor antagonists, which are useful for treating various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to processes for preparing compounds described herein, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors.

Synthesis of new fluoroquinolones and evaluation of their in vitro activity on Toxoplasma gondii and Plasmodium spp.

The synthesis of four new computer-designed fluoroquinolones which have been predicted by QSAR analysis to be active against the protozoa Toxoplasma gondii is described. These compounds are inhibitory in vitro for T. gondii. One of these compounds has a remarkably high activity comparable to that of trovafloxacin. It combines the basic cyclopropyl-quinoline structure of gatifloxacin or moxifloxacin with the C-7 6-amino-3-azabicyclo[3.1.0]hexyl side chain of trovafloxacin. The four compounds are also inhibitory for blood stages of Plasmodium falciparum though at high concentration. These results confirm the potential of quinolones as anti-T. gondii and antimalarial drugs but also show that the QSAR models for T. gondii cannot be reliably extended for screening antimalarial activity.