US2022152229A1PendingUtilityA1
Conjugates and their use as imaging agents
Assignee: CENTENARY INST OF CANCER MEDICINE AND CELL BIOLOGYPriority: Apr 12, 2019Filed: Apr 9, 2020Published: May 19, 2022
Est. expiryApr 12, 2039(~12.7 yrs left)· nominal 20-yr term from priority
A61K 51/0497C07F 9/78A61P 35/00A61K 51/04C07B 59/004A61K 49/04A61K 49/101A61K 51/088C07D 255/02
51
PatentIndex Score
0
Cited by
0
References
0
Claims
Abstract
The invention relates to compounds according to Formula (I) wherein A is —As(OH)2 or an arsenoxide equivalent group; each of R1, R2, R3 and R4 is independently selected from H, X, OH, NH2, CO, SCN, —CH2NH, —NHCOCH3, —NHCOCH2X or NO, and X is a halogen; R5 is —NHCH2COOH, OH or OR6, wherein R6 is a C1-5 straight or branched alkyl group; and Z is a radioisotope with a half-life of less than 4 days, or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof, uses of said compounds, and methods of preparing said compounds. The invention also relates to diagnostic methods utilizing said compounds.
Claims
exact text as granted — not AI-modified1 . A compound according to Formula (I)
wherein A is —As(OH) 2 or an arsenoxide equivalent group;
each of R 1 , R 2 , R 3 and R 4 is independently selected from H, X, OH, NH 2 , CO, SCN, —CH 2 NH, —NHCOCH 3 , —NHCOCH 2 X or NO, and X is a halogen;
R 5 is —NHCH 2 COOH, OH or OR 6 , wherein R 6 is a C 1-5 straight or branched alkyl group;
and Z is a radioisotope with a half-life of less than 4 days,
or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof.
2 . The compound according to claim 1 , wherein each of R 1 , R 2 , R 3 and R 4 are H.
3 . The compound according to claim 1 or claim 2 , wherein R 5 is —NHCH 2 COOH.
4 . The compound according to any one of claims 1 to 3 , which is a compound according to Formula (Ia)
wherein A and Z are as defined in claim 1 ,
or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof.
5 . The compound according to any one of claims 1 to 4 , wherein Z has a half-life of less than 1 day.
6 . The compound according to any one of claims 1 to 5 , wherein Z has a half-life of less than 4 hours.
7 . The compound according to any one of claims 1 to 6 , wherein Z has a half-life of less than 2 hours.
8 . The compound according to claim 7 , wherein Z is 68 Ga.
9 . The compound according to any one of claims 1 to 8 , for use as an imaging agent.
10 . The compound according to claim 9 for use as an imaging agent in positron emission tomography.
11 . The compound according to claim 9 or 10 for use in visualising cell death.
12 . A pharmaceutical composition comprising the compound of any one of claims 1 to 11 together with a pharmaceutically acceptable carrier, excipient, diluent, vehicle and/or adjuvant.
13 . A compound according to Formula (II)
wherein A is —As(OH) 2 or an arsenoxide equivalent group;
each of R 1 , R 2 , R 3 and R 4 is independently selected from H, X, OH, NH 2 , CO, SCN, —CH 2 NH, —NHCOCH 3 , —NHCOCH 2 X or NO, and X is a halogen;
R 5 is —NHCH 2 COOH, OH or OR 6 , wherein R 6 is a C 1-5 straight or branched alkyl group;
or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof.
14 . The compound according to claim 13 , wherein each of R 1 , R 2 , R 3 and R 4 are H.
15 . The compound according to claim 13 or claim 14 , wherein R 5 is —NHCH 2 COOH.
16 . The compound according to any one of claims 13 to 15 , which is a compound according to Formula (IIa)
wherein A is as defined in claim 13 ,
or a pharmaceutically acceptable salt, ester, prodrug or solvate thereof.
17 . Use of a compound according to any one of claims 1 to 11 as an imaging agent.
18 . Use according to claim 17 , wherein the imaging agent is used in positron emission tomography.
19 . Use according to claim 17 or 18 , wherein the imaging agent is used to visualise cell death.
20 . The compound according to any one of claims 1 to 11 for use in therapy.
21 . The compound according to any one of claims 1 to 11 for use in in vivo diagnostics
22 . The compound for use according to claim 20 or 21 for use in the diagnosis or treatment of a condition associated with changes in cell death and/or treatment of which results in a change in cell death.
23 . The compound for use according to claim 22 for use in the treatment or diagnosis of a neoplastic condition or an autoimmune condition.
24 . The compound for use according to claim 23 , wherein the neoplastic condition is a tumour.
25 . The compound for use according to claim 23 or 24 , wherein the neoplastic condition is cancer.
26 . A method of diagnosing or treating a condition in a subject wherein the condition is associated with changes in cell death and/or treatment of the condition results in a change in cell death, or visualising cell death in a subject comprising administering an effective amount of a compound according to any one of claims 1 to 11 to said subject.
27 . The method according to claim 26 wherein the condition is a neoplastic condition or an autoimmune condition.
28 . A method according to claim 26 or 27 , further comprising conducting positron-emission tomography on the subject following administration of the compound according to any one of claims 1 to 11 .
29 . A method according to any one of claims 26 to 28 , wherein multiple positron-emission tomography images are collected following administration of a compound according to any one of claims 1 to 11 .
30 . The method according to any one of claims 26 to 29 wherein the compound according to any one of claims 1 to 11 is administered intravenously.
31 . A method according to any one of claims 26 to 30 wherein the neoplastic condition is a tumour.
32 . A method according to any one of claims 26 to 31 , wherein the neoplastic condition is cancer.
33 . A method of assessing response of a subject to a therapy intended to cause a change in level of cell death, comprising:
administering the therapy; administering a compound according to any one of claims 1 to 11 ; and visualising cell death.
34 . A method according to claim 33 , wherein cell death is visualised by conducting positron emission tomography on the subject.
35 . A method according to claim 34 , wherein the therapy is chemotherapy, radiotherapy, targeted therapy or immunotherapy, or a combination thereof.
36 . A process for preparing a compound according to claim 8 , comprising eluting 68 Ga onto a strong cation exchange column; and eluting the strong cation exchange column into a mixture comprising a compound according to any one of claims 13 to 16 and a buffer, wherein the buffer has a pH of about 4.5.Join the waitlist — get patent alerts
Track US2022152229A1 — get alerts on status changes and closely related new filings.
We store only your email — no account needed. See our privacy policy.