Derivatives of PPD useful for coloring hair and skin

Patent metadata

Field	Value
Publication number	US-11129782-B2
Application number	US-202016875189-A
Country	US
Kind code	B2
Filing date	May 15, 2020
Priority date	Nov 15, 2017
Publication date	Sep 28, 2021
Grant date	Sep 28, 2021

Abstract

The is provided a compound of formula I or II or physiologically acceptable salts or solvates, or oxidised derivatives thereof:

where R 1 to R 3 , R 13 and R 14 are as defined herein. Also disclosed herein are methods of dyeing hair or (temporarily) tattooing the skin using the compounds of formula I or II (or physiologically acceptable salts or solvates, or oxidised derivatives thereof) in a suitable composition.

First claim

The invention claimed is:

1. A compound of formula I:

wherein:
R 1 and R 2 independently represent H, CH 2 Phenyl or C 5-10 alkyl, which phenyl group is substituted by NO 2 , OCH 3 , CH 3 or OH, and which C 5-15 alkyl group is unsubstituted or substituted with one or more substituents selected from:
C 1-10 alkyl, which group is unsubstituted or substituted by one or more substituents selected from OH, nitro, CN, OR 4a , NR 4b R 4c , aryl and Het 1 ;
Cy 1 , which Cy 1 group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-10 alkyl (which C 1-10 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, C 1-4 alkyl and C 1-4 alkoxy), and OR 5a , S(O) q R 5b , S(O) 2 NR 5c R 5d , NR 5e S(O) 2 R 5f , NR 5g R 5h ;
Het a , which Het a group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, halo, C 1-4 alkyl and C 1-4 alkoxy), OR 6a , S(O) q R 6b , S(O) 2 NR 6c R 6d , NR 6e S(O) 2 R 6f , NR 6g R 6h ; and
OR 7a , S(O) q R 7b , S(O) 2 NR 7c R 7d , NR 7e S(O) 2 R 7f and NR 7g R 7h ,

R 3 represents H, OC 1-10 alkyl, C(O)OC 1-10 alkyl or OC(O)C 1-10 alkyl, which OC 1-10 alkyl, C(O)OC 1-10 alkyl and OC(O)C 1-10 alkyl groups are unsubstituted or substituted with one or more substituents selected from:
C 1-10 alkyl, which group is unsubstituted or substituted by one or more substituents selected from OH, nitro, CN, OR 8a , NR 8b R 8c , aryl and Het 2 ;
Cy 2 , which Cy 2 group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, C 1-4 alkyl and C 1-4 alkoxy), and OR 9a , S(O) q R 9b , S(O) 2 NR 9c R 9d , NR 9e S(O) 2 R 9f , NR 9g R 9h ;
Het b , which Het b group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, halo, C 1-4 alkyl and C 1-4 alkoxy), OR 10a , S(O) q R 10b , S(O) 2 NR 10c R 10d , NR 10e S(O) 2 R 10f , NR 10g R 10h ; and
OR 11a , S(O) q R 11b , S(O) 2 NR 11c R 11d , NR 11e S(O) 2 R 11f and NR 11g R 11h ,

Het 1 and Het 2 represent, independently at each occurrence, a 4- to 14-membered heterocyclic group containing one or more heteroatoms selected from O, S and N, which heterocyclic groups may comprise one, two or three rings and may be substituted by one or more substituents selected from OR 12a and C 1-10 alkyl, which C 1-10 alkyl group is unsubstituted;
Cy 1 and Cy 2 represent, independently at each occurrence, a 3- to 6-membered aromatic, fully saturated or partially unsaturated carbocyclic ring;
R 4a to R 4c , R 5a to R 5h , R 6a to R 6h , R 7a to R 7h , R 8a to R 8c , R 9a to R 9h , R 10a to R 10h , R 11a to R 11h , independently represent, at each occurrence, H, or C 1-10 alkyl (which C 1-10 alkyl group is unsubstituted or substituted by one or more substituents selected from C 1-6 alkyl, OR 12b ), or R 5-7c and R 5-7d , R 9-11c and R 9-11d , R 5-7g and R 5-7h , R 9-11g and R 9-11h represent, together with the nitrogen atom to which they are attached, a 3- to 14-membered heterocyclic ring that may be aromatic, fully saturated or partially unsaturated and which may additionally contain one or more heteroatoms selected from O, S and N, which heterocyclic ring is optionally substituted by one or more substituents selected from halo, nitro, CN, and C 1-6 alkyl;
Het a and Het b independently represent 4- to 14-membered heterocyclic groups containing one or more heteroatoms selected from O, S and N;
R 12a-b independently represents, at each occurrence, H or C 1-4 alkyl, and
n represents 0 to 4,
or a physiologically acceptable salt or solvate, or an oxidised derivative thereof of the compound of formula I,
provided that when R 1 and R 2 are H, and n is 0, 1 or 2, R 3 is not H.

2. A method of dyeing hair or of applying a temporary tattoo, which method comprises applying a composition comprising a compound of formula I or a physiologically acceptable salt or solvate, or an oxidised derivative thereof, to the hair or skin of a subject, wherein the compound of formula I has the structure:

wherein:
R 1 and R 2 independently represent H, CH 2 Phenyl or C 5-10 alkyl, which phenyl group is substituted by NO 2 , OCH 3 , CH 3 or OH, and which C 5-10 alkyl group is unsubstituted or substituted with one or more substituents selected from:
C 1-10 alkyl, which group is unsubstituted or substituted by one or more substituents selected from OH, nitro, CN, OR 4a , NR 4b R 4c , aryl and Het 1 ;
Cy 1 , which Cy 1 group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, C 1-4 alkyl and C 1-4 alkoxy), and OR 5a , S(O) q R 5b , S(O) 2 NR 5c R 5d , NR 5e S(O) 2 R 5f , NR 5g R 5h ;
Het a , which Het a group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, halo, C 1-4 alkyl and C 1-4 alkoxy), OR 6a , S(O) q R 6b , S(O) 2 NR 6c R 6d , NR 6e S(O) 2 R 6f , NR 6g R 6h ; and
OR 7a , S(O) q R 7b , S(O) 2 NR 7c R 7d , NR 7e S(O) 2 R 7f and NR 7g R 7h ,

R 3 represents H, C 1-10 alkyl, OC 1-10 alkyl, C(O)OC 1-10 alkyl or OC(O)C 1-10 alkyl, which C 1-10 alkyl, OC 1-10 alkyl, C(O)OC 1-10 alkyl or OC(O)C 1-10 alkyl groups are unsubstituted or substituted with one or more substituents selected from:
C 1-10 alkyl, which group is unsubstituted or substituted by one or more substituents selected from OH, nitro, CN, OR 8a , NR 8b R 8c , aryl and Het 2 ;
Cy 2 , which Cy 2 group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, C 1-4 alkyl and C 1-4 alkoxy), and OR 9a , S(O) q R 9b , S(O) 2 NR 9c R 9d , NR 9e S(O) 2 R 9f , NR 9g R 9h ;
Het b , which Het b group is unsubstituted or substituted by one or more substituents selected from nitro, CN, C 1-6 alkyl (which C 1-6 alkyl group is unsubstituted or substituted by one or more substituents selected from OH, ═O, halo, C 1-4 alkyl and C 1-4 alkoxy), OR 10a , S(O) q R 10b , S(O) 2 NR 10c R 10d , NR 10e S(O) 2 R 10f , NR 10g R 10h ; and
OR 11a , S(O) q R 11b , S(O) 2 NR 11c R 11d , NR 11e S(O) 2 R 11f and NR 11g R 11h ,

Het 1 and Het 2 represent, independently at each occurrence, a 4- to 14-membered heterocyclic group containing one or more heteroatoms selected from O, S and N, which heterocyclic groups may comprise one, two or three rings and may be substituted by one or more substituents selected from OR 12a and C 1-10 alkyl, which C 1-10 alkyl group is unsubstituted;
Cy 1 and Cy 2 represent, independently at each occurrence, a 3- to 6-membered aromatic, fully saturated or partially unsaturated carbocyclic ring;
R 4a to R 4c , R 5a to R 5h , R 6a to R 6h , R 7a to R 7h , R 8a to R 8c , R 9a to R 9h , R 10a to R 10h , R 11a to R 11h , independently represent, at each occurrence, H, or C 1-10 alkyl (which C 1-10 alkyl group

Assignees

• Nat Univ Singapore
• Agency Science Tech & Res
• Nat Univ Hospital Singapore Pte Ltd

Inventors

• Pastorin Giorgia
• Bigliardi Paul
• Valiyaveettil Suresh
• Venkatesan Gopalakrishnan
• Sinha Arup
• Herbert Dancik Yuri
• Bigliardi-Qi Mei

Classifications

• C09B55/009

  Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image) · CPC title

• A61Q1/025

  Semi-permanent tattoos, stencils, e.g. "permanent make-up" · CPC title

• A61K8/411

  Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus · CPC title

• A61Q5/10

  Preparations for permanently dyeing the hair · CPC title

• C09B53/02 Primary

  Indamines; Indophenols · CPC title