209809-20-1

Upstream product

• 66955-75-7 2-(4-amino-3-bromophenyl)acetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 39552-81-3 methyl p-aminophenylacetate 
• 7439-89-6 iron 
• 185200-33-3 methyl (3-bromo-4-nitrophenyl)acetate 
• 150529-73-0 methyl 2-(3-bromophenyl)acetatee 
• 1878-67-7 3-Bromophenylacetic acid 

Downstream Products

• 317356-78-8 methyl 3-bromo-4-[N'-(2-chlorophenyl)ureido] phenylacetate 
• 317356-81-3 methyl 3-bromo-4-[N'-(2-bromophenyl)ureido] phenylacetate 
• 317356-75-5 methyl 3-bromo-4-[N'-(2-methylphenyl)ureido] phenylacetate 
• 34298-84-5 5-indoleacetic acid 
• 317356-82-4 (3-bromo-4-[N'-(2-bromophenyl)ureido]phenyl)acetic acid 
• 317356-79-9 (3-bromo-4-[N'-(2-chlorophenyl)ureido]phenyl)acetic acid 
• 317356-76-6 (3-bromo-4-[N'-(2-methylphenyl)ureido]phenyl)acetic acid 
• 317356-83-5 C₂₈H₂₆Br₂FN₃O₅ 
• 317356-80-2 C₂₈H₂₆BrClFN₃O₅ 
• 317356-77-7 C₂₉H₂₉BrFN₃O₅ 

Relevant academic research and scientific papers

SUBSTITUTED 2-AZA-BICYCLO[2.2.1]HEPTANE-3-CARBOXYLIC ACID (BENZYL-CYANO-METHYL)-AMIDES INHIBITORS OF CATHEPSIN C

This invention relates to 2-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid (benzyl-cyano-methyl)- amides of formula (1) and their use as inhibitors of Cathepsin C, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of diseases connected with dipeptidyl peptidase I activity, e.g. respiratory diseases.

Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3- methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with Ki (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6′-iodononivamide.

Synthesis and biological evaluation of benzoic acid derivatives as potent, orally active VLA-4 antagonists

A series of benzoic acid derivatives was synthesized as VLA-4 antagonists. Introduction of chlorine or bromine into the 3-position on the central benzene of the diphenylurea portion as in lead compound 2 led to improvement in the pharmacokinetic properties. In particular, 12l demonstrated an acceptable plasma clearance and bioavailability in mice and rats as well as dogs (mice, CL = 18.5 ml/min/kg, F = 28 %; rats, CL = 5.2 ml/min/kg, F = 36 %; dogs, CL = 3.6 ml/min/kg, F = 55 %). Additionally, 12l exhibited potent activity with an IC50 value of 0.51 nM and efficacy by oral administration at a dosage of 10 mg/kg in a rat pleurisy model.

VLA-4 inhibitor compounds

Compounds that selectively inhibit the binding of ligands to alpha4beta1 integrin (VLA-4) and methods for their preparation are disclosed. In one embodiment, compounds of the invention are represented by Formula I: As selective inhibitors of VLA-4 mediated cell adhesion, compounds of the present invention are useful in the treatment of conditions associated with such adhesion, including, but not limited to, such conditions as inflammatory and autoimmune responses, diabetes, asthma, psoriasis, inflammatory bowel disease, transplantation rejection, and tumor metastasis. Also disclosed are pharmaceutical compositions, methods of inhibiting VLA-4 mediated cell adhesion and methods of treating conditions associated with LA-4 mediated cell adhesion, which involve compounds of Formula I.

Antidiabetic agents

The instant invention is concerned with aryl and heteroaryl oxyacetic acid type compounds which are useful antidiabetic compounds. Compositions and methods for the use of the compounds in the treatment of diabetes and related diseases and for lowering triglyceride levels are also disclosed.