The present invention relates to the production of tri-functional aromatic molecules from diformylfuran, in particular to the production of tri-methyl benzene derivatives such as for example trimellitic acid or 1,2,4-tri(aminomethyl)benzene from diformylfuran and its derivatives.

The invention belongs to the pharmaceutical manufacturing field, which relates to a novel process for the preparation of substituted phenylacetic acids derivatives, especially relates to the preparation of 2-(4-(2-oxocyclopentyl)phenyl)propanoic acid. The process for the preparation of the precursor form of loxoprofen which use 1,4-di-halobenzyl compounds or disubstituted benzyl compounds as starting material, is through the substitution reaction of cyclopentanone groups or its precursor compounds.

##STR00001##

Wherein X is halogen, L.sub.1 is a suitable leaving group selected from halogen, OH, OMs, OTs, OTf and the like; L.sub.2 is a suitable leaving group selected from halogen, CN, OH, CH.sub.2OH, CHO, CH.sub.3NO.sub.2, ester group, NR.sub.4R.sub.5, OTf, OTs, OMs, CCR.sub.6, CCR.sub.7 and the like, wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 are short chain alkyl groups; Z is cyclopentanone group and its precursor form selected from

##STR00002##

and the like; R.sub.3 is short chain alkyl groups. L.sub.3 is a suitable leaving group selected from halogen, OH, OMs, OTs, OT.sub.f and the like, or organometallic groups. The invention also include the detailed procedure to convert the precursor compounds of cyclopentanone group to cyclopentanone, followed by the transformation of the precursor compounds of loxoprofen to loxoprofen.

The invention belongs to the pharmaceutical manufacturing field, which relates to a novel process for the preparation of substituted phenylacetic acids derivatives, especially relates to the preparation of 2-(4-(2-oxocyclopentyl)phenyl)propanoic acid. The process for the preparation of the precursor form of loxoprofen which use 1,4-di-halobenzyl compounds or disubstituted benzyl compounds as starting material, is through the substitution reaction of cyclopentanone groups or its precursor compounds.

##STR00001##

Wherein X is halogen, L.sub.1 is a suitable leaving group selected from halogen, OH, OMs, OTs, OTf and the like; L.sub.2 is a suitable leaving group selected from halogen, CN, OH, CH.sub.2OH, CHO, CH.sub.3NO.sub.2, ester group, NR.sub.4R.sub.5, OTf, OTs, OMs, CCR.sub.6, CCR.sub.7 and the like, wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 are short chain alkyl groups; Z is cyclopentanone group and its precursor form selected from

##STR00002##

and the like; R.sub.3 is short chain alkyl groups. L.sub.3 is a suitable leaving group selected from halogen, OH, OMs, OTs, OT.sub.f and the like, or organometallic groups. The invention also include the detailed procedure to convert the precursor compounds of cyclopentanone group to cyclopentanone, followed by the transformation of the precursor compounds of loxoprofen to loxoprofen.

The invention belongs to the pharmaceutical manufacturing field, which relates to a novel process for the preparation of substituted phenylacetic acids derivatives, especially relates to the preparation of 2-(4-(2-oxocyclopentyl)phenyl)propanoic acid. The process for the preparation of the precursor form of loxoprofen which use 1,4-di-halobenzyl compounds or disubstituted benzyl compounds as starting material, is through the substitution reaction of cyclopentanone groups or its precursor compounds.

##STR00001##

Wherein X is halogen, L.sub.1 is a suitable leaving group selected from halogen, OH, OMs, OTs, OTf and the like; L.sub.2 is a suitable leaving group selected from halogen, CN, OH, CH.sub.2OH, CHO, CH.sub.3NO.sub.2, ester group, NR.sub.4R.sub.5, OTf, OTs, OMs, CCR.sub.6, CCR.sub.7 and the like, wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 are short chain alkyl groups; Z is cyclopentanone group and its precursor form selected from

##STR00002##

and the like; R.sub.3 is short chain alkyl groups. L.sub.3 is a suitable leaving group selected from halogen, OH, OMs, OTs, OT.sub.f and the like, or organometallic groups. The invention also include the detailed procedure to convert the precursor compounds of cyclopentanone group to cyclopentanone, followed by the transformation of the precursor compounds of loxoprofen to loxoprofen.

Provided is a plasticizer composition comprising a cyclohexane polyester-based substance which is a compound of Chemical Formula 1 as a plasticizer:

##STR00001## in combination with a perhydride comprising a compound of Chemical Formula 2 having a smaller number of ester groups than the cyclohexane polyester-based substance:

##STR00002## Also provided are resin compositions containing the plasticizer composition and methods of preparing the plasticizer composition.

Provided is a plasticizer composition comprising a cyclohexane polyester-based substance which is a compound of Chemical Formula 1 as a plasticizer:

##STR00001## in combination with a perhydride comprising a compound of Chemical Formula 2 having a smaller number of ester groups than the cyclohexane polyester-based substance:

##STR00002## Also provided are resin compositions containing the plasticizer composition and methods of preparing the plasticizer composition.

The present disclosure provides solid forms, including a salt or co-crystal, of Compound I:

##STR00001##

which exhibits Acetyl-CoA carboxylase (ACC) inhibitory activity and may be useful in treating ACC mediated diseases. Also provided herein are processes or steps for the preparation of a Compound I and intermediates useful for the processes or steps described herein.

The present disclosure provides solid forms, including a salt or co-crystal, of Compound I:

##STR00001##

which exhibits Acetyl-CoA carboxylase (ACC) inhibitory activity and may be useful in treating ACC mediated diseases. Also provided herein are processes or steps for the preparation of a Compound I and intermediates useful for the processes or steps described herein.

Process for the preparation of a compound of Formula (I):

##STR00001## the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst,

##STR00002## wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro.

Process for the preparation of a compound of Formula (I):

##STR00001## the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst,

##STR00002## wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro.