US 11,872,298 B2
Cosmetic use of arthrofactin
Luiz Santos, Aulnay-sous-Bois (FR); Lucie Tournier-Couturier, Aulnay-sous-Bois (FR); and Nakako Shibagaki, Aulnay-sous-Bois (FR)
Assigned to L'OREAL, Paris (FR)
Appl. No. 16/471,720
Filed by L'OREAL, Paris (FR)
PCT Filed Dec. 22, 2017, PCT No. PCT/EP2017/084556
§ 371(c)(1), (2) Date Jun. 20, 2019,
PCT Pub. No. WO2018/115522, PCT Pub. Date Jun. 28, 2018.
Claims priority of application No. 16 63253 (FR), filed on Dec. 22, 2016.
Prior Publication US 2020/0022894 A1, Jan. 23, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 8/64 (2006.01); A61K 8/99 (2017.01); A61K 8/06 (2006.01); A61Q 19/00 (2006.01); A61K 47/54 (2017.01); A61K 38/12 (2006.01); A61K 31/20 (2006.01); C07K 7/64 (2006.01); C07K 14/195 (2006.01); C07K 1/107 (2006.01)
CPC A61K 8/64 (2013.01) [A61K 8/062 (2013.01); A61K 8/99 (2013.01); A61K 38/12 (2013.01); A61K 47/542 (2017.08); A61Q 19/007 (2013.01); A61K 31/20 (2013.01); A61K 2800/85 (2013.01); C07K 1/1077 (2013.01); C07K 7/64 (2013.01); C07K 14/195 (2013.01)] 16 Claims
 
1. A cosmetic composition comprising as an active ingredient a mixture of arthrofactins comprising
(i) arthrofactin A of the following formula (I):
R1-D-Leu1-D-Asp2-D-allo-Thr3-D-Leu4-D-Leu5-D-Ser6-L-Leu7-D-Ser8-L-Ile9-L-Ile10-L-Asp11  (I),
wherein
the hydroxyl group of the D-allo-Thr3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp11 amino acid residue, and
R1 represents the group of the following formula (I′):

OG Complex Work Unit Chemistry
wherein R1′ is a saturated alkyl chain with 5 to 8 carbon atoms, and
(ii) at least one derivative of arthrofactin A, said derivative is selected from the group consisting of arthrofactin B, arthrofactin C, arthrofactin D and mixtures thereof,
(a) arthrofactin B being of the following formula (III):
R1-D-Leu1-D-Asp2-D-allo-Thr3-D-Leu4-D-Leu5-D-Ser6-L-Leu7-D-Ser8-L-Ile9-L-Ile10-L-Glu11  (III),
wherein
the hydroxyl group of the D-allo-Thr3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Glu11 amino acid residue, and
R1 represents the group of the following formula (I′):

OG Complex Work Unit Chemistry
wherein R1′ is a saturated alkyl chain with 5 to 8 carbon atoms;
(b) arthrofactin C being of the following (IV):
R2-D-Leu1-D-Asp2-D-allo-Thr3-D-Leu4-D-Leu5-D-Ser6-L-Leu7-D-Ser8-L-Ile9-L-Ile10-L-Asp11  (IV),
wherein
the hydroxyl group of the D-allo-Thr3 amino acid residue forms an ester bond with the carboxyl C-terminal group of the L-Asp11 amino acid residue, and
R2 represents the group of the following formula (IV′):

OG Complex Work Unit Chemistry
wherein R2′ is an alkyl chain with 9 carbon atoms, comprising exactly one unsaturation;
(c) arthrofactin D being of the following formula (V):
R3-D-Leu1-D-Asp2-D-allo-Thr3-D-Leu4-D-Leu5-D-Ser6-L-Leu7-D-Ser8-L-Ile9-L-Ile10-L-Asp11  (V),
wherein
the hydroxyl group of the D-allo-Thr3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp11 amino acid residue, and
R3 represents the group of the following formula (V′):

OG Complex Work Unit Chemistry
wherein R3′ is a saturated alkyl chain with 9 carbon atoms;
the composition further comprising a physiologically acceptable medium; wherein the amount of the mixture of arthrofactins is between 0.01 and 10% by weight based upon the weight of the composition and the composition is in the form of an emulsion, a cream, an ointment, a milk, a lotion, a serum, a paste, a gel, a foam or a stick.