170641-06-2

Upstream product

• 288-94-8 1H-tetrazole 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 208122-80-9 (1-Benzyloxymethyl-1H-tetrazol-5-yl)-phenyl-methanol 
• 371143-40-7 1-benzyloxymethyl-5-(phenylacetylglycyl)tetrazole 

Relevant academic research and scientific papers

SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES

The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.

PIPERIDINYL DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present application describes modulators of MIP-1α of formula (I) or stereoisomers or prodrugs or pharmaceutically acceptable salts thereof, wherein m, Q, T, W, Z, R1, R3, R4, R5, R5a and R5b, are as defined herein. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis using the modulators of formula (I) are disclosed.

PIPERIDINE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present application describes modulators of MIP-1 of formula (I) : or stereoisomers or pharmaceutically acceptable salts thereof, wherein m, Q, T, W, Z, R1, R3, R4, R5, R5a and R5b, are as set forth above. In addition, methods of treating and preventing inflammatory diseases such as asthma and allergic diseases, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis using the modulators are disclosed.

Heterocyclic compounds as inhibitors of factor VIIa

The present invention relates generally to compounds that inhibit serine proteases. In particular it is directed to novel heterocyclic compounds, or a stereoisomer or pharmaceutically acceptable salt, solvate, or prodrug form thereof, which are useful as selective inhibitors of serine protease enzymes of the coagulation cascade; for example thrombin, factor VIIa, factor Xa, factor XIa, factor IXa, and/or plasma kallikrein. In particular, it relates to compounds that are factor VIIa inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same.

Design, synthesis, and evaluation of α-ketoheterocycles as class C β-lactamase inhibitors

A series of specific α-ketoheterocycles (benzoxazole, thiazole, imidazole, tetrazole, and thiazole-4-carboxylate) has been synthesized in order to assess their potential as β-lactamase inhibitors. The syntheses were achieved either by construction of the heterocycle (benzoxazole) from an appropriate α-hydroxyimidate, followed by oxidation of the alcohol, or by direct reaction of methyl phenaceturate with a lithiated heterocycle. The properties of these compounds in aqueous solution are described and their inhibitory activity against β-lactamases assessed. They did inhibit the class C β-lactamase of Enterobacter cloacae P99 but not the TEM β-lactamase. The most effective inhibitor of the former enzyme (Ki = 0.11 mM) was 5-(phenylacetylglycyl) tetrazole, probably because it is an anion at neutral pH. Interpretation of the results was aided by computational models of the tetrahedral adducts. Most of the compounds also inhibited α-chymotrypsin but not porcine pancreatic elastase.

2-Benzyloxymethyl-5-(tributylstannyl)tetrazole. A reagent for the preparation of 5-aryl- and 5-heteroaryl-1H-tetrazoles via the Stille reaction

2-Benzyloxymethyl-5-(tributylstannyl)tetrazole (2) is a useful reagent for the conversion of aryl- and heteroarylhalides (bromides and iodides) to 5-aryl- and 5-heteroaryl-1H-tetrazoles. The conversion entails a copper(I) iodide co-catalyzed Stille palladium-catalyzed cross-coupling reaction and a N-benzyloxymethyl deprotection step. Coupling was possible with electron neutral and electron poor substrates in yields ranging from 35-93%. (C) 2000 Elsevier Science Ltd.

Homologation of 1-(benzyloxymethyl)-1H-tetrazole via lithiation

Lithiation of 1-(Benzyloxymethyl)-1H-tetrazoIe, prepared by alkylation of 1H-tetrazole with benzyl chloromethyl ether, followed by treatement with a variety of electrophiles afforded its homologation products. Hydrogenation or acid hydrolysis gave the corresponding free tetrazoles.

Synthesis of tetrazoles bearing a sugar moiety (sugar tetrazoles). X-Ray molecular structure of '(7R,8R,9S,10R)-8,9,10-tribenzyloxy-7-benzyloxymethyl-6-oxa-1,5-pentamethylenetetrazole'

Thermolysis of perbenzylated D-glucopyranosediyl diazide 1 and D-galactopyranosediyl diazide 4 afforded, respectively, the corresponding 6-oxa-1,5-pentamethylenetetrazoles 2 and 5 via the sugar azido nitrenes, while, photolysis of diazides 1 and 4 gave, respectively, compounds 2 and 5 together with the corresponding byproducts, 10-oxa-1,5-pentamethylenetetrazoles 3 and 6.Similarly, 5-(sugar chain)-substituted tetrazole 9 was obtained by the thermolysis of perbenzylated 1,1-diazido acyclic sugar 8, while compound 9 and 1-(sugar chain)-substituted tetrazole 10 were formed by the photolysis of compound 8.Interestingly, the thermolysis and photolysis of 1,1-diazido-2,3-di-O-benzyl-D,L-glyceraldehyde 8f gave both the corresponding 9f and 10f.