Phosphoantigen prodrug compounds

{
  "publication_number": "US2021171552A1",
  "country": "US",
  "kind": "A1",
  "title": "Phosphoantigen prodrug compounds",
  "abstract": "The invention relates to a compound of General Formula (I): wherein R1, R2, R3, R4 and R5 are as defined herein. Compounds and compositions comprising the same exhibit high serum stability and potent activation of the γδ T-cell immune response, so are suitable for use in immunotherapy. The invention also relates to methods of immunotherapy using the compounds of General Formula (I).",
  "claims": [
    "1. A compound according to General Formula (I) including all tautomers thereof: wherein R1 and R2 each independently represents an amino acid ester radical according to General Formula (II) or an aryloxy radical according to General Formula (III): wherein R6 represents H, or a saturated or unsaturated and optionally substituted hydrocarbon chain; R7 represents a saturated or unsaturated and optionally substituted hydrocarbon chain; and R8 represents an optionally substituted C 5-25 aryl or a 5 to 25 membered heteroaryl group; R3 represents an optionally substituted C 2-20 alkyl, C 4-20 alkenyl or C 2-20 alcohol radical; and each of R4 and R5 independently represent H or halo; or a salt thereof. 2. A compound according to claim 1, wherein said compound is of General Formula (IV), wherein R3, R4, R5, R6, R7 and R8 are as defined in claim 1: 3. A compound according to claim 1, wherein R3 is a radical according to Formula (V), Formula (VI) or Formula (VII), wherein R9 is selected from OH, OR 10, SH, SR 10, NH 2 or NHR 10, and wherein R 10 represents C 1-4 alkyl: 4. A compound according to claim 3, wherein R9 is OH. 5. A compound according to claim 1, wherein one or both, of R4 and R5 represent halo. 6. A compound according to claim 5, wherein said halo substituents is/are fluoro. 7. A compound according to claim 1, wherein R6 is a C 1-4 alkyl chain. 8. A compound according to claim 1, wherein R7 is an unsubstituted C 1-4 alkyl chain or an unsubstituted benzyl group. 9. A compound according to claim 1, selected from: 10. A pharmaceutical composition comprising a compound as defined in claim 1 and a pharmaceutically acceptable excipient or carrier. 11. (canceled) 12. (canceled) 13. (canceled) 14. A method of immunotherapy, the method comprising administering to a subject an effective amount of a compound as defined in claim 1 to activate a γδ T-cell immune response. 15. A method according to claim 14, wherein said compound is administered ex vivo to a sample obtained from an individual in need of treatment to induce proliferation of γδ T cells prior to said sample being returned to the body. 16. A method according to claim 14, wherein said compound is administered to treat an infection, a proliferative disease or osteoporosis. 17. A method according to claim 16, wherein said proliferative disease is a cancer. 18. (canceled) 19. (canceled) 20. (canceled) 21. A method of immunotherapy, the method comprising administering to a subject an effective amount of a pharmaceutical composition as defined in claim 10 to activate a γδ T-cell immune response. 22. A method according to claim 21, wherein said composition is administered to treat an infection, a proliferative disease or osteoporosis. 23. A method according to claim 22, wherein said proliferative disease is a cancer. 24. A method according to claim 21, wherein said composition is administered ex vivo to a sample obtained from an individual in need of treatment to induce proliferation of γδ T cells prior to said sample being returned to the body. 25. A method according to claim 24, wherein said composition is administered to treat an infection, a proliferative disease or osteoporosis. 26. A method according to claim 25, wherein said proliferative disease is a cancer. 27. A method according to claim 15, wherein said compound or composition is administered to treat an infection, a proliferative disease or osteoporosis. 28. A method according to claim 27, wherein said proliferative disease is a cancer."
  ],
  "cpc": [
    "C07F 9/4465",
    "A61K 31/664",
    "A61K 35/17",
    "A61K 40/11",
    "A61K 40/42",
    "A61P 19/00",
    "A61P 35/00",
    "A61P 37/00",
    "A61P 37/04",
    "C12N 2501/999",
    "C12N 5/0636"
  ],
  "assignees": [
    "UNIV COLLEGE CARDIFF CONSULTANTS LTD",
    "UNIV BIRMINGHAM"
  ],
  "filing_date": "2019-07-03",
  "publication_date": "2021-06-10",
  "priority_date": "2018-07-04",
  "application_number": "US-201917256272-A",
  "family_id": "63143832",
  "citations": [
    "WO2019182904A1"
  ]
}