# US 2017/0283384 A1 · Psma targeted fluorescent agents for image guided surgery

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- Number: US 2017/0283384 A1
- Document ID: US20170283384A1
- Status: Published application
- Kind: A1
- Application number: 15/618,788
- Filed: 2017-06-09
- Published: 2017-10-05
- Earliest claimed: 2009-03-19
- Assignees: The Johns Hopkins University; Intuitive Surgical Operations, Inc.
- Applicants: The Johns Hopkins University; Intuitive Surgical Operations, Inc.
- Inventors: MARTIN G. POMPER; RONNIE C. MEASE; YING CHEN; SANGEETA RAY; JONATHAN SORGER
- Web page: https://patentgrep.com/patent/US20170283384A1

## CPC

- C07D 257/02: not condensed with other rings
- A61K 49/0032: {Methine dyes, e.g. cyanine dyes}
- A61K 49/0052: {Small organic molecules (oligomers, polymers, dendrimers A61K49/0054)}
- A61K 51/0421: {having six-membered rings with one oxygen as the only ring hetero atom}
- A61K 51/044: {having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins (rifampin A61K51/0459)}
- A61K 51/0446: {having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil}
- A61K 51/0453: {having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole}
- A61K 51/0472: {containing heavy metals, e.g. hemin, hematin, melarsoprol}
- C07D 209/12: Radicals substituted by oxygen atoms
- C07D 209/14: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D 209/24: with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
- C07D 213/04: having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D 249/04: 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D 255/02: not condensed with other rings
- C07D 311/14: substituted in position 6 and unsubstituted in position 7
- C07D 311/20: hydrogenated in the hetero ring
- C07D 311/82: Xanthenes
- C07F 5/027: {Organoboranes and organoborohydrides}
- C07F 13/005: {Compounds without a metal-carbon linkage}
- G01N 33/5091: {for testing the pathological state of an organism}
- G01N 2800/342: Prostate diseases, e.g. BPH, prostatitis
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

Compositions and methods for visualizing tissue under illumination with near-infrared radiation, including compounds comprising near-infrared, closed chain, sulfo-cyanine dyes and prostate specific membrane antigen ligands are disclosed.

## Claims

### Claim 1

A compound of the following formula:
or a pharmaceutically acceptable salt thereof.

### Claim 2

A composition comprising compound (3):
or a pharmaceutically acceptable salt thereof;
wherein the composition is adapted for visualization of tissue under illumination with near-infrared radiation.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the composition is adapted for administration to a subject.

### Claim 4 (depends on 3)

The composition of claim 3, wherein the composition comprises a unit dosage form of compound (3).

### Claim 5 (depends on 4)

The composition of claim 4, wherein the unit dosage form delivers to the subject an amount of compound (3) between about 0.01 and about 8 mg/kg.

### Claim 6 (depends on 5)

The composition of claim 5, wherein the unit dosage form delivers to the subject an amount of compound (3) of about 0.01 mg/kg, about 0.05 mg/kg, about 0.10 mg/kg, about 0.20 mg/kg, about 0.3 mg/kg, about 0.35 mg/kg, about 0.40 mg/kg, about 0.45 mg/kg, about 0.50 mg/kg, about 0.55 mg/kg, about 0.60 mg/kg, about 0.65 mg/kg, about 0.70 mg/kg, about 0.75 mg/kg, about 0.80 mg/kg, about 0.90 mg/kg, about 1 mg/kg, about 2, mg/kg, about 4 mg/kg, about 6 mg/kg, or about 8 mg/kg.

### Claim 7 (depends on 2)

The composition of claim 2, wherein the composition is in a single dose form.

### Claim 8 (depends on 2)

The composition of claim 2, wherein the composition is in dry form.

### Claim 9 (depends on 2)

The composition of claim 2, wherein the composition is lyophilized in a sterile container.

### Claim 10 (depends on 2)

The composition of claim 2, wherein the composition is contained within a sterile container.

### Claim 11 (depends on 10)

The composition of claim 10, wherein the sterile container comprises a machine detectable identifier.

### Claim 12 (depends on 2)

The composition of claim 2, further comprising one or more pharmaceutically acceptable excipients in an oral dosage form.

### Claim 13 (depends on 2)

The composition of claim 2, further comprising one or more pharmaceutically acceptable carriers in an injectable dosage form.

### Claim 14 (depends on 2)

The composition of claim 2, further comprising one or more pharmaceutically acceptable excipients in a dosage form for direct delivery to a surgical site.

### Claim 15 (depends on 2)

The use of a composition of claim 2 for administration to a subject to obtain visualization of tissue expressing PSMA under illumination with near-infrared radiation.

### Claim 16 (depends on 15)

The use of claim 15, wherein the subject is a human subject.

### Claim 17

A method for visualization of tissue expressing PSMA, the method comprising administering to a subject a composition comprising compound (3):
or a pharmaceutically acceptable salt thereof;
wherein compound (3) is administered in an amount sufficient for imaging tissue under illumination with near-infrared radiation;
imaging the tissue under illumination with near-infrared radiation; and
obtaining at least one image of tissue from the subject.

### Claim 18 (depends on 17)

The method of claim 17, wherein the composition comprises a unit dosage form of compound (3).

### Claim 19 (depends on 18)

The method of claim 18, wherein the unit dosage form delivers to the subject an amount of compound (3) from about 0.01 mg/kg and about 8 mg/kg.

### Claim 20 (depends on 18)

The method of claim 18, wherein the composition is sterile, non-toxic, and adapted for administration to a subject.

### Claim 21 (depends on 17)

The method of claim 17, further comprising obtaining the image during administration, after administration, or both during and after administration of the composition.

### Claim 22 (depends on 17)

The method of claim 17, further comprising intravenously injecting a composition comprising compound (3) into the subject.

### Claim 23 (depends on 22)

The method of claim 22, wherein the composition is injected into a circulatory system of the subject.

### Claim 24 (depends on 17)

The method of claim 17, further comprising visualizing a subject area on which surgery is or will be performed.

### Claim 25 (depends on 24)

The method of claim 24, further comprising performing a surgical procedure of the subject area based on the visualization of the area.

### Claim 26 (depends on 24)

The method of claim 24, further comprising viewing a subject area on which an ophthalmic, arthroscopic, laparoscopic, cardiothoracic, muscular, or neurological procedure is or will be performed.

### Claim 27 (depends on 17)

The method of claim 17, further comprising diagnosing the subject with a condition or disease based on the visualization of the tissue expressing PSMA.

### Claim 28 (depends on 17)

The method of claim 17, further comprising obtaining ex vivo images of at least a portion of the subject.

### Claim 29 (depends on 17)

The method of claim 17, wherein the tissue being visualized comprises tumor tissue.

### Claim 30 (depends on 17)

The method of claim 17, wherein the tissue being visualized comprises cancerous tissue.

### Claim 31 (depends on 17)

The method of claim 17, wherein the tissue being visualized comprises prostate tissue.

### Claim 32 (depends on 17)

The method of claim 17, wherein the tissue being visualized comprises prostate tumor tissue.

### Claim 33 (depends on 17)

The method of claim 17, wherein the tissue being visualized comprises nerve tissue.

### Claim 34 (depends on 17)

The method of claim 17 wherein the tissue being visualized comprises clear cell renal cell carcinoma.