# US 10,501,496 B2 · Chemical synthesis and screening of bicyclic peptide libraries > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,501,496 B2 - Document ID: US10501496B2 - Status: Granted - Kind: B2 - Application number: 15/672,617 - Filed: 2017-08-09 - Published: 2018-02-01 - Granted: 2019-12-10 - Earliest claimed: 2013-05-23 - Assignees: Ohio State Innovation Foundation - Applicants: Ohio State Innovation Foundation - Inventors: Dehua Pei; Punit Upadhyaya; Wenlong Lian; Thi Trinh - Web page: https://patentgrep.com/patent/US10501496B2 ## CPC - C07K 7/64: Cyclic peptides containing only normal peptide links - C07K 5/0202: {containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids} - C07K 5/06156: {and Trp-amino acid; Derivatives thereof} - C07K 5/0817: {the first amino acid being Arg} - A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00) - C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract Disclosed herein are bicyclic peptide compounds, compositions comprising same, methods for making same, and libraries comprising same. The disclosed compounds, in various aspects, are useful for treating a variety of disorders, including inflammatory disorders, autoimmune disorders, and disorders of uncontrolled cellular proliferation. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention. ## Claims ### Claim 1 A compound of Formula I: wherein: A is benzene; p, q, and r are independently selected from 0, 1, and 2; B1, B2, and B3 are independently selected from O and NR1; wherein R1 is H, or substituted or unsubstituted C1-C5 alkyl; L1 is selected from substituted or unsubstituted C1-C6 alkyl, amino acid, and a linker to a solid phase support; L2 is selected from hydrogen, substituted or unsubstituted C1-C6 alkyl, amino acid, and a linker to a solid phase support; D is selected from substituted or unsubstituted C1-C6 alkyl, or amino acid residue; and Xm and Xn independently comprise a sequence of 1-10 amino acids. ### Claim 2 (depends on 1) The compound of claim 1, wherein one or more of p, q, and r is 1. ### Claim 3 (depends on 1) The compound of claim 1, wherein L1 and L2 are independently selected from an amino acid. ### Claim 4 (depends on 1) The compound of claim 1, wherein L1 is lysine. ### Claim 5 (depends on 1) The compound of claim 1, wherein D is an amino acid residue. ### Claim 6 (depends on 1) The compound of claim 1, wherein one or more of B1, B2, and B3 is NR1, and R1 is H. ### Claim 7 (depends on 1) The compound of claim 1, wherein each of p, q, and r is 0; L1 is lysine; each of B1, B2, and B3 is NR1, wherein R1 is H; and D-L2 is —CH2—CH(NH)—C(O)—NH—R0. ### Claim 8 (depends on 7) The compound of claim 7, wherein the compound is of Formula I-A: wherein: Xm and Xn are as defined in Formula I; R0 is selected from hydrogen, substituted or unsubstituted C1-C6 alkyl; and K has a structure represented by a formula: ### Claim 9 (depends on 1) The compound of claim 1, wherein Xm and Xn comprise different amino acid sequences. ### Claim 10 (depends on 1) The compound of claim 1, wherein Xm comprises 3-7 residues. ### Claim 11 (depends on 1) The compound of claim 1, wherein Xm comprises 4-6 residues. ### Claim 12 (depends on 1) The compound of claim 1, wherein Xn comprises 2-6 residues. ### Claim 13 (depends on 1) The compound of claim 1, wherein Xn comprises 3-5 residues. ### Claim 14 (depends on 1) The compound of claim 1, wherein the compound has a molecular weight of 500-5000. ### Claim 15 (depends on 1) The compound of claim 1, wherein Xm and Xn are selected from SEQ ID NO: 1-4 and 6-63. ### Claim 16 (depends on 1) The compound of claim 1, wherein Xm and Xn are selected from SEQ ID NO: 1-4 and 6-25.