Method for producing pyrazoles, novel pyrazoles and applications thereof

Patent metadata

Field	Value
Publication number	US-9802980-B2
Application number	US-201414766048-A
Country	US
Kind code	B2
Filing date	Feb 7, 2014
Priority date	Feb 11, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

A method for preparing a pyrazole of formula (I) in which R,R′ and R″ have different meanings, characterised in that it involves reacting a sydnone of formula (II) in which R and R′ have the meanings already indicated, with an alkyne of formula (III) in which R″ has the meaning already indicated, in the presence of copper, to obtain a pyrazole compound of formula (I) that is then isolated and salified if desired.

First claim

The invention claimed is:

1. A process for preparing a pyrazole of formula I

in which
R represents a hydrogen atom; a halogen atom; a thio or -thioalkyl group; a hydroxyl or alkoxy group; an amino or -aminoalkyl group; an alkyl radical containing from 1 to 8 carbon atoms which is unsubstituted or substituted one or more times with F, Cl, Br, I , CN, OH, NH2, NH—(C1-C8 alkyl), N—(C1-C8 alkyl)2, SH; an aryl radical containing 6 to 10 carbon atoms which is unsubstituted or substituted one or more times with an alkyl or alkoxy radical containing 1 to 8 carbon atoms; a heterocycle; an amino acid; a polypeptide; a protein; a nucleic acid; a DNA molecule; a polysaccharide; a polymer; a nanoparticle; a dendrimer;
R′ represents a hydrogen atom; a halogen atom; a thio or -thioalkyl group; a hydroxyl or, alkoxy group; an amino or -aminoalkyl group; an alkyl radical containing from 1 to 8 carbon atoms which is unsubstituted or substituted one or more times with F, Cl, Br, I, CN, OH, NH2, NH—(C1-C8 alkyl), N—(C1-C8 alkyl) 2, SH; an aryl radical containing 6 to 10 carbon atoms which is unsubstituted or substituted one or more times with an alkyl or alkoxy radical containing 1 to 8 carbon atoms; a heterocycle;
R″ represents a hydrogen atom; a halogen atom; a thio group; a hydroxyl group; an amino group; a hydrocarbon-based group or a hydrocarbon-based group containing from 1 to 100 heteroatoms;

wherein a sydnone of formula II

in which R and R′ have be meanings already indicated, is reacted with an alkyne of formula III

in which R″ has the meaning already indicated, in the presence of copper salt complexed with a nitrogenous ligand used as a catalyst metal, so as to obtain a pyrazole compound of formula I which is isolated and salified if desired.

2. A process as claimed in claim 1 , wherein R represents an unsubstituted or substituted aryl or heteroaryl radical.

3. A process as claimed in claim 1 , wherein R′ represents a hydrogen atom.

4. A process as claimed in claim 1 , wherein R″ represents a hydrogen atom; a halogen atom; a thio or -thioalkyl group; a hydroxyl or alkoxy group; an amino or -aminoalkyl group; an alkyl radical containing from 1 to 8 carbon atoms which is unsubstituted or substituted one or more times with F, Cl, Br, I, CN, OH, —O-heterocycle which is substituted or unsubstituted, NH2, —NH—(C1-C8 alkyl), —N—(C1-C8 alkyl)2, —NH—R′″ or —(C1-C3 alkyl)—NH—R″′ where R″′ represents a sulfonated group, SH; an aryl radical containing 6 to 10 carbon atoms which is unsubstituted or substituted one or more times with an alkyl or alkoxy radical containing 1 to 8 carbon atoms; a heterocycle; an amino acid; a. polypeptide; a protein; a nucleic acid; a DNA molecule; a polysaccharide; a polymer; a nanoparticle; a dendrimer.

5. A process as claimed in claim 4 , wherein R″ represents a heteroaryl radical or an aryl radical or an alkyl radical containing from 1 to 8 carbon atoms.

6. A process as claimed in claim 1 , wherein the nitrogenous ligand is chosen from phenanthrolines, triazoles, pyridines, imidazoles and benzimidazoles.

Assignees

• Commissariat Energie Atomique

Inventors

• Taran Frederic
• Chaumontet Manon
• Kolodych Sergii
• Rasolofonjatovo Andovola Evelia

Classifications

• C07D405/14

  containing three or more hetero rings · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title