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US 2017/0000712 A1Published application
Sunless tanning compounds and compositions
AssigneeRegents of the University of Minnesota
InventorsRobert Vince, Abbas Raza, Christine Dreis
Life of this patent
Estimating the term…
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).
Claims24
A sunless tanning composition comprising a compound of formula I:
- wherein:
- each R1 is independently H, (C1-C6)alkyl, (C3-C7)carbocycle or RaC(═O)—, and the two R4 groups together form a —(C3-C8)alkyl- group, a —(C2-C6)alkyl-Y—(C2-C6)alkyl- group or a —(C1-C6)alkyl-Y′—(C1-C6)alkyl- group;
- or
- each R4 is independently H, (C1-C6)alkyl, (C3-C7)carbocycle or RaC(═O)—, and the two R1 groups together form a —(C3-C8)alkyl- group, a —(C2-C6)alkyl-Y—(C2-C6)alkyl- group or a —(C1-C6)alkyl-Y′—(C1-C6)alkyl- group;
- or
- the two R4 groups together form a —(C3-C8)alkyl- group, a —(C2-C6)alkyl-Y—(C2-C6)alkyl group or a —(C1-C6)alkyl-Y′—(C1-C6)alkyl- group and the two R1 groups together form a —(C3-C8)alkyl- group, a —(C2-C6)alkyl-Y—(C2-C6)alkyl- group or a —(C1-C6)alkyl-Y′—(C1-C6)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;
- R2 is H, (C1-C6)alkyl or aryl, wherein aryl is optionally substituted with one or more Z1 groups;
- R3 is H, (C1-C6)alkyl or aryl, wherein aryl is optionally substituted with one or more Z1 groups;
- Y is O, S, NH, NRc, P, P(═O) or POH;
- Y′ is Si(Rb)2 or —Si(Rb)2—O—Si(Rb)2—;
- each Ra is independently (C1-C6)alkyl, (C3-C7)carbocycle or aryl, wherein aryl is optionally substituted with one or more Z1 groups;
- each Rb is independently (C1-C6)alkyl, (C3-C7)carbocycle or aryl, wherein aryl is optionally substituted with one or more Z1 groups;
- each Rc is independently Rg or a C1-C18 saturated or unsaturated carbon chain that is optionally substituted with one or more groups independently selected from oxo (═O), hydroxy, mercapto, (C1-C6)alkoxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, NRdRe, carboxy, and aryl, wherein any aryl of Rc is optionally substituted with one or more Rf;
- each Rd and Re is independently selected from H, (C1-C6)alkyl, (C1-C6)alkanoyl, phenyl, benzyl, and Rg;
- each Rf is independently selected from (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, —C(═O)-phenyl, and —C(═O)CH2C(═O)-phenyl, wherein any phenyl is optionally substituted with one or more groups independently selected from (C1-C6)alkyl, —SO3H, and (C1-C6)alkoxy;
- each Rg is
- each Z1 is independently selected from (C1-C6)alkyl, halogen, —CN, —ORn1, —NRq1Rr1, —NRn1CORp1, —NRn1CO2Rp1, NO2, —C(O)Rn1, —C(O)ORn1 and —C(O)NRq1Rr1, wherein any (C1-C6)alkyl of Z1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rn1 is independently selected from H and (C1-C6)alkyl, wherein any (C1-C6)alkyl of Rn1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rp1 is independently (C1-C6)alkyl;
- and
- Rq1 and Rr1 are each independently selected from H and (C1-C6)alkyl or Rq1 and Rr1 together with the nitrogen to which they are attached form a piperidine, pyrrolidine, morpholine, azetidine, thiomorpholine, piperazine or 4-methylpiperazine;
- or a salt thereof.
21 more elements
5-7. (canceled)
(canceled)
A sunless tanning composition comprising a compound of formula II:
- or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier,
- wherein:
- R1 is H, (C1-C6)alkyl, (C3-C7)carbocycle or RaC(═O)—;
- R2 is H, (C1-C6)alkyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- R4 is H, (C1-C10)alkyl, (C3-C7)carbocycle or RaC(═O)—;
- Ra is or (C1-C6)alkyl, (C3-C7)carbocycle or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- each Z1 is independently selected from (C1-C6)alkyl, halogen, —CN, —ORn1, —NRq1Rr1, —NRn1CORp1, —NRn1CO2Rp1, NO2, —C(O)Rn1, —C(O)ORn1 and —C(O)NRq1Rr1, wherein any (C1-C6)alkyl of Z1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rn1 is independently selected from H and (C1-C6)alkyl, wherein any (C1-C6)alkyl of Rn1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rp1 is independently (C1-C6)alkyl;
- and
- Rq1 and Rn1 are each independently selected from H and (C1-C6)alkyl or Rq1 and Rr1 together with the nitrogen to which they are attached form a piperidine, pyrrolidine, morpholine, azetidine, thiomorpholine, piperazine or 4-methylpiperazine
- or a salt thereof.
9 more elements
A sunless tanning composition comprising a compound of formula III:
- wherein:
- each R1 is independently H, (C1-C6)alkyl, (C3-C7)carbocycle or RaC(═O;
- or the two R1 groups together form a —(C3-C5)alkyl- group, a —(C2-C6)alkyl-Y—(C2-C6)alkyl- group or a —(C1-C6)alkyl-Y′—(C1-C6)alkyl- group;
- or
- the dashed bonds labeled “a” are absent and the dashed bonds labeled “b” are double bonds;
- or all the dashed bonds are single bonds;
- R2 is H, (C1-C6)alkyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- R3 is H, (C1-C6)alkyl or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- R4 is hydroxy, carboxy, (C1-C6)alkoxycarbonyl, —OPO3H2, —ORc, or —NRdRe;
- and R5 is H;
- or R4 and R5 taken together are oxo;
- Y is O, S, NH, P, P(═O) or POH;
- Y′ is Si(Rb)2 or —Si(Rb)2—O—Si(Rb)2—;
- each Ra is independently (C1-C6)alkyl, (C3-C7)carbocycle or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- each Rb is independently (C1-C6)alkyl, (C3-C7)carbocycle or aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- Rc is Rf or a C1-C20 saturated or C2-C20 unsaturated carbon chain that is optionally substituted with one or more groups independently selected from oxo (═O), hydroxy, mercapto, (C1-C6)alkoxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, NRdRe, carboxy, and aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- Rd is H, (C1-C6)alkyl, or (C1-C6)alkanoyl;
- Re is H or a C1-C20 saturated or C2-C20 unsaturated carbon chain that is optionally substituted with one or more groups independently selected from oxo (═O), hydroxy, mercapto, (C1-C6)alkoxy, (C1-C6)alkoxycarbonyl, (C1-C6)alkanoyloxy, NRdRe, carboxy, and aryl, wherein aryl is optionally substituted with one or more (e.g. 1, 2, 3, 4 or 5) Z1 groups;
- each Rf, is:
- each Z1 is independently selected from (C1-C6)alkyl, halogen, —CN, —ORn1, —NRq1Rr1, —NRl1CORp1, —NRn1CO2Rp1, NO2, —C(O)Rn1, —C(O)ORn1 and —C(O)NRq1Rr1, wherein any (C1-C6)alkyl of Z1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rn1 is independently selected from H and (C1-C6)alkyl, wherein any (C1-C6)alkyl of Rn1 is optionally substituted with one or more (e.g. 1, 2, 3, 4, 5 or 6) halogen;
- each Rp1 is independently (C1-C6)alkyl;
- and
- Rq1 and Rr1 are each independently selected from H and (C1-C6)alkyl or Rq1 and Rr1 together with the nitrogen to which they are attached form a piperidine, pyrrolidine, morpholine, azetidine, thiomorpholine, piperazine or 4-methylpiperazine;
- or a salt thereof.
22 more elements
21-22. (canceled)
24-26. (canceled)
Dependencies are inferred from the claim text.