Sunless tanning compounds and compositions

Patent metadata

Field	Value
Publication number	US-9987211-B2
Application number	US-201414901979-A
Country	US
Kind code	B2
Filing date	Jul 2, 2014
Priority date	Jul 3, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

The invention provides sunless tanning compositions comprising a compounds of formula (I): or a salt thereof as described herein as well as methods for tanning mammalian skin by contacting the skin with the compounds of formula (I) or compositions comprising compounds of formula (I).

First claim

What is claimed is:

1. A method of tanning mammalian skin comprising administering to mammalian skin in need thereof, an effective amount of a sunless tanning composition comprising a compound of formula I:

wherein:
each R 1 is independently H, (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or R a C(═O)—, and the two R 4 groups together form a —(C 3 -C 8 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group; or
each R 4 is independently H, (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or R a C(═O)—, and the two R 1 groups together form a —(C 3 -C 8 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group; or
the two R 4 groups together form a —(C 3 -C 8 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group and the two R 1 groups together form a —(C 3 -C 8 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group;
the dashed bonds labeled “a” are absent and the dashed bonds labeled “b” are double bonds; or all the dashed bonds are single bonds;
R 2 is H, (C 1 -C 6 )alkyl or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
R 3 is H, (C 1 -C 6 )alkyl or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
Y is O, S, NH, NR c , P, P(═O) or POH;
Y′ is Si(R b ) 2 or —Si(R b ) 2 —O—Si(R b ) 2 —;
each R a is independently (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
each R b is independently (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
each R c is independently R g or a C 1 -C 18 saturated or unsaturated carbon chain that is optionally substituted with one or more groups independently selected from oxo (═O), hydroxy, mercapto, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, NR d R e , carboxy, and aryl, wherein any aryl of R c is optionally substituted with one or more R f ;
each R d and R e is independently selected from H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl, phenyl, benzyl, and R g ;
each R f is independently selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, —C(═O)-phenyl, and —C(═O)CH 2 C(═O)-phenyl, wherein any phenyl is optionally substituted with one or more groups independently selected from (C 1 -C 6 )alkyl, —SO 3 H, and (C 1 -C 6 )alkoxy;
each R g is

each Z 1 is independently selected from (C 1 -C 6 )alkyl, halogen, —CN, —OR n1 , —NR q1 R r1 , —NR n1 COR p1 , —NR n1 CO 2 R p1 , NO 2 , —C(O)R n1 , —C(O)OR n1 and —C(O)NR q1 R r1 , wherein any (C 1 -C 6 )alkyl of Z 1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
each R n1 is independently selected from H and (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl of R n1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
each R p1 is independently (C 1 -C 6 )alkyl; and
R q1 and R r1 are each independently selected from H and (C 1 -C 6 )alkyl or R q1 and R r1 together with the nitrogen to which they are attached form a piperidine, pyrrolidine, morpholine, azetidine, thiomorpholine, piperazine or 4-methylpiperazine;
or a salt thereof.

2. The method of claim 1 wherein the wherein the sunless tanning composition comprises a compound of formula I selected from:

or a salt thereof.

3. A method of providing an artificial tan to mammalian skin comprising administering to mammalian skin in need thereof, an effective amount of a sunless tanning composition comprising a compound of formula I:

wherein:
each R 1 is independently H, (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or R a C(═O)—, and the two R 4 groups together form a —(C 3 -C 5 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group; or
each R 4 is independently H, (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or R a C(═O)—, and the two R 1 groups together form a —(C 3 -C 5 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group; or
the two R 4 groups together form a —(C 3 -C 5 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group and the two R 1 groups together form a —(C 3 -C 8 )alkyl- group, a —(C 2 -C 6 )alkyl-Y—(C 2 -C 6 )alkyl- group or a —(C 1 -C 6 )alkyl-Y′—(C 1 -C 6 )alkyl- group;
the dashed bonds labeled “a” are absent and the dashed bonds labeled “b” are double bonds; or all the dashed bonds are single bonds;
R 2 is H, (C 1 -C 6 )alkyl or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
R 3 is H, (C 1 -C 6 )alkyl or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
Y is O, S, NH, NR c , P, P(═O) or POH;
Y′ is Si(R b ) 2 or —Si(R b ) 2 —O—Si(R b ) 2 —;
each R a is independently (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
each R b is independently (C 1 -C 6 )alkyl, (C 3 -C 7 )carbocycle or aryl, wherein aryl is optionally substituted with one or more Z 1 groups;
each R c is independently R g or a C 1 -C 18 saturated or unsaturated carbon chain that is optionally substituted with one or more groups independently selected from oxo (═O), hydroxy, mercapto, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, NR d R e , carboxy, and aryl, wherein any aryl of R c is optionally substituted with one or more R f ;
each R d and R e is independently selected from H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkanoyl, phenyl, benzyl, and R;
each R f is independently selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkoxycarbonyl, (C 1 -C 6 )alkanoyloxy, —C(═O)-phenyl, and —C(═O)CH 2 C(═O)-phenyl, wherein any phenyl is optionally substituted with one or more groups independently selected from (C 1 -C 6 )alkyl, —SO 3 H, and (C 1 -C 6 )alkoxy;
each R g is

each Z 1 is independently selected from (C 1 -C 6 )alkyl, halogen, —CN, —OR n1 , —NR q1 R r1 , —NR n1 COR p1 , —NR n1 CO 2 R p1 , NO 2 , —C(O)R n1 , —C(O)OR n1 and —C(O)NR q1 R r1 , wherein any (C 1 -C 6 )alkyl of Z 1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
each R n1 is independently selected from H and (C 1 -C 6 )alkyl, wherein any (C 1 -C 6 )alkyl of R n1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
each R p1 is independently (C 1 -C 6 )alkyl; and
R q1 and R r1 are each independently selected from H and (C 1 -C 6 )alkyl or R

Assignees

• Univ Minnesota

Inventors

• Vince Robert
• Raza Abbas
• Dreis Christine

Classifications

• C07D239/52

  Two oxygen atoms · CPC title

• C07D487/16

  Peri-condensed systems · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A61P17/00

  Drugs for dermatological disorders · CPC title

• A61Q19/04

  for chemically tanning the skin (topical sun or radiation screening or tanning preparations A61Q17/04) · CPC title