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US 2014/0350036 A1Published application
Agents that prevent or repair skin damage
AssigneeRegents of the University of Minnesota
InventorsRobert Vince, Abbas Raza, Christine Dreis
Life of this patent
Estimating the term…
Abstract
The invention provides compounds of formula I: or a salt thereof as described herein. The invention also provides dermatological compositions comprising a compound of formula I or mixtures of one or more compounds of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for protecting skin or DNA from photodamage or repairing photodamaged skin or DNA.
Claims41
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
Dependencies are inferred from the claim text.