Roussel Uclaf

Pierre Fabre Dermo-cosmetique

Diverchim

Jean-Louis Brayer

Jean-Pierre Demoute

Gilles Mourioux

Marc D Benoit

Laurent Taliani

Natacha Frison

Benoit Folleas

Sylvain Laugraud

Jean Tessier

Pascal Bordat

Jean-Hilaire Saurat

Sylvie Daunes-Marion

Roger Tarroux

Olivier Sorg

Janine Cossy

Nicole Reinier

Marie Charveron

Yannick Le Stanc

Daniel Calvo

Francois Ottello

Christophe Meyer

Benoit De Carne Carnavalet

Rukiye Pamuk

Emmanuel Thomas

Peter Oosting

Benoït De Carne Carnavalet

Benoît Folleas

Cyclopropylboronic compounds, the preparation process thereof and the use thereof.

Cyclopropylboronic compounds, preparation process thereof and use thereof

The invention concerns novel polyunsaturated compounds of formula (I) wherein: Rrepresents a R', -A-R&#x2032;group, R&#x2032;being selected from &#x2014;COOH, &#x2014;COOR, &#x2014;CONH, &#x2014;CONHR, &#x2014;CONRR, &#x2014;CHO, &#x2014;CHOH, &#x2014;CHOR, and A represents a C-Calkylene, alkenylene or alkynylene; Rrepresents: an optionally substituted aryl group or an optionally substituted heteroaryl group; a sugar residue or, a fatty acid residue optionally branched and/or substituted preferably at the chain terminus and particularly by hydroxy, acetoxy radical or by an optionally protected amino radical; a &#x2014;OC &#x2014;(CH)n CO-tocopheryl (alpha, beta or gamma or delta) group, with 2 $m(F) n $m(F) 10; a &#x2014;R&#x2032;&#x2014;O&#x2014;Rgroup, wherein R&#x2032;is an optionally substituted arylene group or an optionally substituted heteroarylene group, and Rrepresents a hydrogen atom, a straight or branched optionally substituted C-Calkyl, a straight or branched optionally substituted C-Calkenyl, or a straight or branched C-Calkynyl group, an optionally substituted tocopheryl radical or the like, an amino acid residue, or a sugar residue. The invention also concerns the compositions, in particular cosmetic and/or dermatological compositions containing at least one compound of formula (I) as well as their use as whitening and/or depigmenting agent, and the cosmetic method using said compositions.

Polyunsaturated compounds, method for preparing same and compositions containing the same

The invention concerns a method for preparing a compound of formula (I), wherein: Rand Rrepresent in particular H and n is greater than 4, said preparation method including performing a Wittig-Horner reaction with a phosphonate on a lactol, so as to obtain a hydroxyester and, optionally a saponification reaction of said hydroxyester.

Method for preparing unsaturated fatty hydroxyacids

A compound of the formula ##STR1## wherein Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, methylenedioxy, phenyl, phenoxy, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, chlorine, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are individually alkyl of 1 to 6 carbon atoms and the exocyclic double bonds independently have (E) or (Z) geometry having fungicidal activity and a process for their preparation.

.alpha.-methylene-5-thiazolacetic acid esters

7-ethynyl -alpha- (methoxymethylene) -1- naphthalene acetic acid

.alpha.- methylene-5-thiazolacetic acid esters

7-ethylene-.alpha.-(methoxymethylene)-1-naphthalene-acetic acid

All possible stereoisomer forms and mixtures of a compound of the formula ##STR1## wherein X is a halogen, R.sub.2 and R.sub.3 are individually selected from the group consisting of alkyl and cycloalkyl of up to 8 carbon atoms optionally substituted with at least one halogen, R.sub.1 is selected from the group consisting of alkyl, alkenyl, alkynyl and cycloalkyl of up to 12 carbon atoms optionally substituted with at least one halogen, aryl and heteroaryl of 5 to 6 ring members optionally substituted with at least one member of the group consisting of halogen, alkyl, alkenyl, alkynyl and cycloalkyl of up to 8 carbon atoms optionally substituted with at least one member of the group consisting of --NO.sub.2, --NH.sub.2, --CN, --OR', --SR', --SOR', --SO.sub.2 R', --NR''.sub.2, --Ar, OAr.sub.1 and SAr.sub.2, R', R' and R'' are individually selected from the group consisting of alkyl, alkenyl, alkynyl and cycloalkyl of up to 12 carbon atoms optionally substituted by at least one halogen, Ar, Ar.sub.1 and Ar.sub.2 are aryl or heteroaryl of up to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen and alkyl, alkenyl, alkynyl and cycloalkyl of up to 8 carbon atoms optionally substituted by at least one member of the group consisting of halogen, --NO.sub.2, --NH.sub.2, --CN, --OR', --SR', --SOR', --SO.sub.2 R' and --NR''.sub.2 and R', R' and R'' have the above definitions and their preparations and novel intermediates useful as pesticides.

Alpha-methylene-6-styryl-acrylic acid derivatives

Alpha-methylene-5-thiazolacetic acid esters

A region-specific monofunctionalization of a phenolic hydroxy onto a polyphenol for the preparation of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --CN, formyl, carboxy, alkoxy carbonyl of up to 9 carbon atoms, aralkoxy carbonyl or up to 12 carbon atoms and halogen and R' is a hydroxy protective group comprising reacting a polyphenol of the formula ##STR2## wherein R has the above definition with a base to form the corresponding dianion, reacting the latter with a trialkyl borate of the formula

Monofunctionalization of phenolic hydroxy onto a polyphenol

A process for the preparation of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --SO.sub.2 alk and alk is alkyl of 1 to 8 carbon atoms, optionally substituted aryl, aryloxy and arylthio of 6 to 18 carbon atoms and optionally substituted heteroaryl, heteroaryloxy and heterocyclic of 5 to 6 ring members, R.sub.3 is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 18 carbon atoms and alkoxyalkoxyalkyl of 3 to 14 carbon atoms, X is selected from the group consisting of --O--, --S-- and --NR.sub.4 --, R.sub.4 is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 8 carbon atoms, --SO.sub.2 alkyl, --SO.sub.2 alkenyl and --SO.sub.2 alkynyl of up to 8 carbon atoms and optionally substituted aryl and --SO.sub.2 aryl of 6 to 18 carbon atoms, the double bond between the heterocycle of 5 member ring and the aromatic nucleus is of E and/or Z geometry comprising reacting a halide of the formula ##STR2## wherein R.sub.3 is as defined above and Hal is hydrogen with a compound of the formula ##STR3## wherein X, R.sub.1 and R.sub.2 have the above definitions in the presence of a base to obtain the corresponding product of formula I in the form of a mixture of isomers and optionally separating the isomers and novel intermediates of formula II.

Process for preparation of thiazolylalkoxy acrylates

A compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, optionally substituted alkyl, alkenyl and alkynyl of up to 8 carbon atoms, optionally substituted cycloalkyl or cycloalkenyl of up to 8 carbon atoms, optionally substituted aryl of 6 to 18 carbon atoms, optionally substituted aralkyl of 7 to 24 carbon atoms, optionally substituted benzoyl and optionally substituted heterocycle, the optional substituents being at least one member of the group consisting of halogen, phenoxy, thiazolyl, alkyl and alkoxy of 1 to 6 carbon atoms and haloalkyl, Alk.sub.1 and Alk.sub.2 are individually optionally substituted alkyl of 1 to 8 carbon atoms, X is --O-- or --S-- and R' is hydrogen or halogen in any position on the phenyl and the geometry of the double bond is E or Z or a mixture of E and Z and having useful pesticidal properties.

Insecticidal benzofuran derivatives

A compound of the formula ##STR1## wherein Ar is phenyl optionally substituted with at least one member of the group consisting of halogen, methylenedioxy, phenoxy, phenyl, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, Z is selected from the group consisting of hydrogen, chlorine, --CF.sub.3 and alkyl, alkoxy and alkylthio of 1 to 6 carbon atoms, R.sub.1 and R.sub.2 are individually alkyl of 1 to 6 carbon atoms and the exocyclic double bond has (Z) or (E) configuration having fungicidal activity.

.alpha.-Methylene-4-(phenoxymethyl)-5-thiazolacetate

A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of Ar-O- and aryl, polyaryl and condensed polyaryl unsubstituted or substituted and heterocycle unsubstituted or substituted, Ar is aryl of 6 to 14 carbon atoms unsubstituted or substituted, heteroaryl unsubstituted or substituted and heterocyclic unsubstituted or substituted, W is selected from the group comsisting of --(CH.sub.2).sub.n.sbsb.1 --or --(CH.sub.2).sub.n.sbsb.2 --NY--(CH.sub.2).sub.n.sbsb.3, n.sub.1, n.sub.2 and n.sub.3 are individually integers from 2 to 6, Y is selected from the group consisting of hydrogen, alkyl of 1 to 12 carbon atoms, aryl of 6 to 12 carbon atoms and aralkyl of 7 to 14 carbon atoms unsubstituted or substituted, --COOAlk and --COR.sub.2, Alk is alkyl of 1 to 12 carbon atoms, R.sub.2 is selected from the group consisting of alkyl of 1 to 12 carbon atoms, alkenyl and alkynyl of 2 to 12 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms unsubstituted or substituted and heterocyclic unsubstituted or substituted, Z is selected from the group consisting of hydrogen, ##STR2## R.sub.2 is alkyl of 1 to 12 carbon atoms or aralkyl of 7 to 18 carbon atoms, Alk' is alkyl of 1 to 12 carbon atoms, ArAlk is aralkyl of 7 to 18 carbon atoms, R.sub.2 ' is R.sub.2, R.sub.3 and R.sub.3 ' are selected from the group consisting of aryl substituted or unsubstituted, heteroaryl substituted or unsubstituted, heterocyclic unsubstituted or substituted and R.sub.1 with the proviso that Z is not hydrogen when W is --(CH.sub.2).sub.3 --and R.sub.1 is 2,4-dichlorophenoxy and their non-toxic, pharmaceutically acceptable acid addition salts having fungicidal activity.

Acylated amine compounds which are useful fungicigal agents

Growing community of inventors

Nanteuil le Haudoin, France

Jean-Louis Brayer