# US 11,027,027 B2 · Pyridazinoindole compounds and methods for PET imaging

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- Number: US 11,027,027 B2
- Document ID: US11027027B2
- Status: Granted
- Kind: B2
- Application number: 15/012,795
- Filed: 2016-02-01
- Published: 2016-08-04
- Granted: 2021-06-08
- Earliest claimed: 2015-01-30
- Assignees: Vanderbilt University
- Applicants: Vanderbilt University
- Inventors: H. Charles Manning; Yiu-Yin Cheung; Jason R. Buck; Jun Li
- Web page: https://patentgrep.com/patent/US11027027B2

## CPC

- A61K 49/0052: {Small organic molecules (oligomers, polymers, dendrimers A61K49/0054)}
- A61K 49/0041: {Xanthene dyes, used in vivo, e.g. administered to a mice, e.g. rhodamines, rose Bengal (in vivo G01N)}
- A61K 51/0459: {having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine}
- C07D 487/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07H 17/04: Heterocyclic radicals containing only oxygen as ring hetero atoms
- A61K 49/0032: {Methine dyes, e.g. cyanine dyes}
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Embodiments of the invention include a novel synthesis of the translocator protein (TSPO) ligands, and methods of imaging a molecular events. Also disclosed are compounds for treatment of diseases, including cancer.

## Claims

### Claim 1

A compound of the following formula:
wherein R1 and R2 are independently ethyl; and n is 8.

### Claim 2 (depends on 1)

A compound of claim 1, wherein the signaling agent is chosen from:
wherein X is the conjugation site.

### Claim 3 (depends on 1)

A compound of claim 1, of the following formula:

### Claim 4

A method of quantifying the progression of a disease state in a subject, comprising:
(a) administering to a first sample of the subject a conjugate, the conjugate comprising a TSPO affinity ligand of the following formula:
wherein R1 and R2 are independently ethyl, and n is 8;
(b) detecting a signal from said conjugate;
(c) after a period of time from step (b), administering to a second sample of the subject a conjugate, the conjugate comprising TSPO affinity ligand of the following formula:
wherein R1 and R2 are independently ethyl, and n is 8;
(d) detecting a second signal; and
(e) comparing the first signal with the second signal to determine the progress of a disease state.

### Claim 5 (depends on 4)

The method of claim 4, wherein the signaling agent is selected from the following formula:
wherein X is the conjugation site.

### Claim 6 (depends on 4)

The method of claim 4, where in the disease state is breast cancer, non-Hodgkin's lymphoma, colon cancer.

### Claim 7 (depends on 4)

The method of claim 4, wherein the period of time between step (b) and the administering to a second sample step, includes a treatment step for said disease state.