# US 2014/0154186 A1 · Bacteriochlorin imides

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- Number: US 2014/0154186 A1
- Document ID: US20140154186A1
- Status: Published application
- Kind: A1
- Application number: 14/117,212
- Filed: 2012-05-30
- Published: 2014-06-05
- Earliest claimed: 2011-05-31
- Assignees: North Caroliina State University
- Inventors: Jonathan S. Lindsey; Michael Krayer
- Web page: https://patentgrep.com/patent/US20140154186A1

## CPC

- C07D 487/22: in which the condensed system contains four or more hetero rings
- A61K 41/0071: {PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines}
- A61K 49/0036: {Porphyrins (used in photodynamic therapy A61K41/0071 or A61K41/0076; used as targeting group or modifying agent for targeting a therapeutic compound A61K47/546)}
- A61N 5/062: {Photodynamic therapy, i.e. excitation of an agent}
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C09B 47/00: Porphines; Azaporphines {(non-dyeing compounds C07D487/22)}
- G01N 15/1404: Handling flow, e.g. hydrodynamic focusing
- G01N 33/582: {with fluorescent label}
- 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)
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- 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

Compound of Formula I: are described, along with compositions containing the same and methods of use thereof.

## Claims

### Claim 1

A compound of Formula I:
wherein:
M is a metal or is absent;
each X is independently selected from the group consisting of Se, NH, CH2, O and S;
Z is O, S or a covalent bond;
R and each R1 and R2 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; or R1 and R2 together are ═O or spiroalkyl;
each R3 and R4 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, and arylalkyl;
each R5 is independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; and
R6, R6a and R7a are each independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups; and
R8 is selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, heterocyclo, heterocycloalkyl, heterocycloalkenyl, heterocycloalkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkoxy, halo, mercapto, azido, cyano, formyl, carboxylic acid, hydroxyl, nitro, acyl, aryloxy, alkylthio, amino, alkylamino, arylalkylamino, disubstituted amino, acylamino, acyloxy, ester, amide, sulfoxyl, sulfonyl, sulfonate, sulfonic acid, sulfonamide, phosphate, phosphonate, urea, alkoxylacylamino, aminoacyloxy, linking groups, hydrophilic groups, targeting groups, and surface attachment groups;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein M is present and is selected from the group consisting of Pd, Pt, Mg, Zn, Al, Ga, In, Sn, Cu, Ni, and Au.

### Claim 3 (depends on 1)

The compound of claim 1, wherein each X is NH.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Z is O.

### Claim 5 (depends on 1)

The compound of claim 1, wherein Z is S.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Z is a covalent bond.

### Claim 7 (depends on 1)

A compound of claim 1 wherein said targeting group is selected from the group consisting of proteins, peptides, and nucleic acids.

### Claim 8 (depends on 1)

In a method of detecting cells or particles by flow cytometry, wherein said cells or particles are labelled with a detectable luminescent compound, the improvement comprising utilizing a bacteriochlorin as the luminescent compound, wherein said bacteriochlorin is a compound of claim 1.

### Claim 9 (depends on 1)

A composition consisting of a compound of claim 1, optionally in a solvent, wherein: said composition has a peak molar absorption coefficient in solution of 10,000 to 300,000 M−1cm−1 at a wavelength between 700 and 1000 nanometers; and/or said composition has a loss of not more than 20 percent of said compound when stored in a sealed vessel at room temperature in the absence of ambient light for at least 3 months.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 in a pharmaceutically acceptable carrier.

### Claim 11 (depends on 1)

A method for treating a target in a subject in need thereof, comprising: (i) administering to said subject the compound of claim 1 or a pharmaceutically acceptable conjugate thereof that preferentially associates with the target, and (ii) irradiating the target with light of a wavelength and intensity sufficient to treat said target.

### Claim 12 (depends on 1)

A photodynamic therapy method for treating hyperproliferative tissue in a subject in need thereof, comprising: (i) administering to said subject a compound of claim 1 or a pharmaceutically acceptable conjugate thereof that preferentially associates with the hyperproliferative tissue, and (ii) irradiating the target with light of a wavelength and intensity sufficient to activate the compound, and thereby treat said hyperproliferative tissue.

### Claim 13 (depends on 1)

A method for detecting the presence of a hyperproliferative tissue in a subject, comprising: (i) administering to the subject a compound of claim 1 or a pharmaceutically acceptable conjugate thereof that preferentially associates with the hyperproliferative tissue; and then (ii) visualizing the compound within the patient.

### Claim 14 (depends on 1)

A kit to treat hyperproliferative disorders, comprising the compound of claim 1 or a pharmaceutically acceptable conjugate thereof and instructions teaching a method of photodynamic therapy.

### Claim 15 (depends on 1)

In a light harvesting rod, the improvement comprising utilizing a compound of claim 1 as at least one chromophore therein.

### Claim 16 (depends on 1)

In a solar cell, the improvement comprising utilizing a compound of claim 1 as the chromophore or photosensitizer therein; wherein said compound of claim 1 is in monomeric form or is optionally linked to at least one additional chromophore to form a light harvesting rod.

### Claim 17 (depends on 1)

In an information storage device utilizing a charge storage molecule in monomeric or polymeric form, the improvement comprising utilizing as said charge storage molecule a compound of claim 1.

### Claim 18 (depends on 1)

A method of making a compound of claim 1, comprising:
Reacting a compound of Formula II:
with a compound of the formula R8NH2 and carbon monoxide in an organic solvent in the presence of a base and a transition metal catalyst to produce a compound of claim 1, wherein:
X′ is halo;
R′ is loweralkyl; and
the remaining substituents are as given in claim 1.