US 11,911,447 B2
Peptide pharmaceuticals for insulin resistance
John J. Nestor, Sugar Land, TX (US)
Assigned to Mederis Diabetes LLC, Sugar Land, TX (US)
Filed by Mederis Diabetes LLC, Sugar Land, TX (US)
Filed on Jun. 16, 2021, as Appl. No. 17/349,195.
Application 17/349,195 is a division of application No. 14/646,264, granted, now 11,065,304, previously published as PCT/US2013/071077, filed on Nov. 20, 2013.
Claims priority of provisional application 61/728,649, filed on Nov. 20, 2012.
Prior Publication US 2022/0362345 A1, Nov. 17, 2022
Int. Cl. A61K 38/26 (2006.01); C07K 14/605 (2006.01); A61K 47/54 (2017.01); A61K 38/00 (2006.01)
CPC A61K 38/26 (2013.01) [A61K 47/549 (2017.08); C07K 14/605 (2013.01); A61K 38/00 (2013.01)] 18 Claims
 
1. A peptide selected from Formula II:
 
 Formula II
 
 (SEQ. ID. NO. 1)
 
 aa1-aa2-aa3-aa4-aa5-aa6-aa7-aa8-aa9-aa10-aa11-
 
 
 
 aa12-aa13-aa14-aa15-aa16-aa17-aa18-aa19-aa20-aa21-
 
 
 
 aa22-aa23-aa24-aa25-aa26-aa27-aa28-aa29-aa30-aa31-
 
 
 
 aa32-aa33-aa34-aa35-aa36-aa37-Z
wherein:
Z is OH, N-R4—His, or —NH-R3,
wherein
R3 is H, substituted or unsubstituted C1-C12 alkyl;
R4 is a C2-C10 acyl group, for example Ac or Bz;
aa1 is His, N-R4-His, pGlu-His, or N-R3-His;
aa2 is Aib;
aa3 is Gln or Cit;
aa4 is Gly or D-Ala;
aa5 is Thr or Ser;
aa6 is Phe, Trp, 2FPhe, MePhe, 2FMePhe, or Nal2;
aa7 is Thr or Ser;
aa8 is Ser or Asp;
aa9 is Asp or Glu;
aa10 is Tyr, Leu, Met, Nal2, Bip, or Bip2EtMeO;
aa11 is Ser, Asn, or Bip;
aa12 is Lys, Glu, Ser, or Arg;
aa13 is Tyr, Gln, or Cit;
aa14 is Leu, Met, or Nle;
aa15 is Asp, or Glu;
aa16 is Ser, Gly, Glu, Ala, Aib, Ac5c, Lys, or Arg;
aa17 is Lys;
aa18 is Arg, hArg, Ala, Aib, Ac4c, or Ac5c;
aa19 is Ala, Val, Aib, Ac4c, or Ac5c;
aa20 is Gln, Lys, Arg, Cit, Glu, Aib, Ac4c, or Ac5c;
aa21 is Asp, Glu, Leu, Aib, Ac4c, or Ac5c;
aa22 is Phe, Trp, Nal2, Aib, Ac4c, or Ac5c;
aa23 is Val, Ile, Aib, Ac4c, or Ac5c;
aa24 is Gln, Ala, Glu, or Cit;
aa25 is Trp, or Nal2;
aa26 is Leu;
aa27 is Leu;
aa28 is Gln;
aa29 is Thr, Gly, Aib, Ac4c, or Ac5c;
aa30 is absent or Lys, Aib, Ac4c, Ac5c, or Arg;
aa31 is absent or Arg, Aib, Ac4c, or Ac5c;
aa32 is absent or Asn, Aib, Ac4c, or Ac5c;
aa33 is absent or Arg, Aib, Ac4c, or Ac5c;
aa34 is absent or Asn, Aib, Ac4c, or Ac5c;
aa35 is absent or Asn, Aib, Ac4c, or Ac5c;
aa36 is absent or Ile, Aib, Ac4c, or Ac5C;
aa36 is absent or Ala, Aib, Ac4c, or Ac5C;
aa37 is absent;
wherein any two of aa1-aa36 are optionally cyclized through their side chains to form a lactam linkage.