US2019328834A1PendingUtilityA1
Arthrofactin for the treatment of acne
Est. expiryDec 22, 2036(~10.4 yrs left)· nominal 20-yr term from priority
Inventors:Lucie Tournier-Couturier
A61P 17/10A61K 38/12A61K 9/0014
33
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Claims
Abstract
The present invention relates to a mixture of arthrofactin or of a composition containing it and to the use thereof for the treatment of acneic skin.
Claims
exact text as granted — not AI-modified1 . An arthrofactin mixture comprising
(i) arthrofactin A of formula (I) below:
R 1 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Asp 11 (I),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp 11 amino acid residue, and
R 1 represents the group of formula (I′) below:
where R 1 ′ is a saturated alkyl chain of 5 to 8 carbon atoms; and
(ii) at least one derivative of arthrofactin A, said derivative being of formula (II) below:
R-Xaa 1 -Xaa 2 -Xaa 3 -Xaa 4 -Xaa 5 -Xaa 6 -Xaa 7 -Xaa 8 -Xaa 9 -Xaa 10 -Xaa 11 (II)
in which
Xaa 1 , Xaa 4 , Xaa 5 , Xaa 7 , Xaa 9 and Xaa 10 each represent, independently, D-Leu, L-Leu, D-Ile or L-Ile,
Xaa 2 and Xaa 11 each represent, independently, D-Asp, L-Asp, D-Glu or L-Glu,
Xaa 3 represents D-Thr, L-Thr, D-allo-Thr or L-allo-Thr,
Xaa 6 and Xaa 8 each represent, independently, D-Ser, L-Ser, D-Gln or L-Gln,
the hydroxyl group of the Xaa 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the Xaa 11 amino acid residue, and
R represents the group of formula (II′) below:
where R′ is an alkyl chain of 5 to 9 carbon atoms, optionally comprising at least one unsaturation;
for the treatment of acneic skin.
2 . The mixture according to claim 1 , in which said acneic skin has imperfections related to Propionibacterium acnes.
3 . The mixture according to claim 1 , for inhibiting the growth of Propionibacterium acnes.
4 . The mixture according to claim 1 , in which R 1 ′ is a saturated alkyl chain of 7 carbon atoms.
5 . The mixture according to claim 1 , in which said at least one derivative of arthrofactin A is chosen from the group consisting of arthrofactin B, arthrofactin C, arthrofactin D and mixtures thereof,
arthrofactin B being of formula (III) below:
R 1 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Glu 11 (III),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Glu 11 amino acid residue, and
arthrofactin C being of formula (IV) below:
R 2 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Asp 11 (IV),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp 11 amino acid residue, and
R 2 represents the group of formula (IV′) below:
where R 2 ′ is an alkyl chain of 9 carbon atoms comprising exactly one unsaturation;
arthrofactin D being of formula (V) below:
R 3 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Asp 11 (V),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp 11 amino acid residue, and
R 3 represents the group of formula (V′) below:
where R 3 ′ is a saturated alkyl chain of 9 carbon atoms.
6 . The mixture according to claim 1 , in which said arthrofactin mixture comprises
(iii) arthrofactin A of formula (IA) below:
(iv) at least one derivative of arthrofactin A chosen from the compounds of formula (IIA), (IIB) and/or (IIC) of formula(e) below:
7 . The mixture according to claim 1 , in which said at least one derivative of arthrofactin A is a mixture of said compounds of formula (IIA), (IIB) and (IIC).
8 . The mixture according to claim 1 , in which the arthrofactin mixture predominantly comprises arthrofactin A.
9 . The mixture according to claim 1 , in which said arthrofactin mixture is capable of being obtained by fermentation with the Pseudomonas sp. MIS38 strain.
10 . A composition comprising the arthrofactin mixture as defined in claim 1 , for the treatment of acneic skin.
11 . The composition according to claim 10 , said composition being a dermatological composition.
12 . The composition according to claim 10 , in which said acneic skin has imperfections related to P. acnes.
13 . The composition according to claim 10 , for inhibiting the growth of Propionibacterium acnes.
14 . The mixture according to claim 3 , in which said at least one derivative of arthrofactin A is chosen from the group consisting of arthrofactin B, arthrofactin C, arthrofactin D and mixtures thereof,
arthrofactin B being of formula (III) below:
R 1 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Glu 11 (III),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Glu 11 amino acid residue, and
R 1 is as defined in claim 1 ;
arthrofactin C being of formula (IV) below:
R 2 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Asp 11 (IV),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp 11 amino acid residue, and
R 2 represents the group of formula (IV′) below:
where R 2 ′ is an alkyl chain of 9 carbon atoms comprising exactly one unsaturation;
arthrofactin D being of formula (V) below:
R 3 -D-Leu 1 -D-Asp 2 -D-allo-Thr 3 -D-Leu 4 -D-Leu 5 -D-Ser 6 -L-Leu 7 -D-Ser 8 -L-Ile 9 -L-Ile 10 -L-Asp 11 (V),
in which
the hydroxyl group of the D-allo-Thr 3 amino acid residue forms an ester bond with the C-terminal carboxyl group of the L-Asp 11 amino acid residue, and
R 3 represents the group of formula (V′) below:
where R 3 ′ is a saturated alkyl chain of 9 carbon atoms.
15 . The mixture according to claim 4 , in which said arthrofactin mixture comprises
(iii) arthrofactin A of formula (IA) below:
(iv) at least one derivative of arthrofactin A chosen from the compounds of formula (IIA), (IIB) and/or (IIC) of formula(e) below:
16 . The mixture according to claim 4 , in which said arthrofactin mixture comprises
(iii) arthrofactin A of formula (IA) below:
(iv) at least one derivative of arthrofactin A chosen from the compounds of formula (IIA), (IIB) and/or (IIC) of formula(e) below:
17 . The mixture according to claim 4 , in which said at least one derivative of arthrofactin A is a mixture of said compounds of formula (IIA), (IIB) and (IIC).
18 . The mixture according to claim 5 , in which said at least one derivative of arthrofactin A is a mixture of said compounds of formula (IIA), (IIB) and (IIC).
19 . The mixture according to claim 6 , in which said at least one derivative of arthrofactin A is a mixture of said compounds of formula (IIA), (IIB) and (IIC).
20 . The mixture according to claim 4 , in which the arthrofactin mixture predominantly comprises arthrofactin A.Join the waitlist — get patent alerts
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