# US 2014/0155362 A1 · Bhq-conjugates, and related compounds, methods of making the same, and methods of use thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2014/0155362 A1
- Document ID: US20140155362A1
- Status: Published application
- Kind: A1
- Application number: 14/117,058
- Filed: 2012-06-28
- Published: 2014-06-05
- Earliest claimed: 2011-06-28
- Inventors: Timothy M. Dore; James D. Lauderdale; Adam C. Rea; Adna Muliawan; Duncan McLain
- Web page: https://patentgrep.com/patent/US20140155362A1

## CPC

- A61K 47/545: {Heterocyclic compounds (A61K47/558 takes precedence)}
- A61K 31/138: Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine (atenolol A61K31/165; pindolol A61K31/404; timolol A61K31/5377)
- A61K 31/165: having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- A61K 31/58: containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin (digitoxin {A61K31/7048})
- A61N 5/062: {Photodynamic therapy, i.e. excitation of an agent}
- 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)

## Abstract

Embodiments of the present disclosure provide for BHQ-conjugates and protected BHQ-conjugate precursor compounds, methods of making BHQ-conjugates and protected BHQ-conjugate precursor compounds, methods of using BHQ-conjugates and protected BHQ-conjugate precursor compounds, and the like.

## Claims

### Claim 1

A composition, comprising:
a BHQ-conjugate or a protected BHQ-conjugate precursor compound.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the conjugate is selection from the group consisting of: a serotonin (5HT), a capsaicinoid, and a catechol.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the BHQ-conjugate is selected from the group consisting of: BHQ-O-5HT, BHQ-N-5HT, BHQ-capsaicin, BHQ-VNA (vanillyamide of n-nonanoic acid), BHQ-VAA, BHQ-dopamine, BHQ-epinephrine, BHQ-noreepinephrine, BHQ-tyrosine, BHQ-tyrosine(Fmoc), BHQ-hydroxytamoxifen, BHQ-morphine, BHQ-oripavine, BHQ-estriol, BHQ-estrone, and BHQ-estradiol.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the BHQ-conjugate has the following structure:
wherein R1 is selected from the group consisting of: H, Br, F, Cl, I, and CN; and wherein R2 is selected from the group consisting of: H, F, Cl, Br, I, OH, OR, NRR′, CH3, CN, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl, wherein R and R′ are each independently selected from the group consisting of: H, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the protected BHQ-conjugate precursor compound has the following structure:
wherein R1 is selected from the group consisting of: H, Br, F, Cl, I, and CN; wherein R2 is selected from the group consisting of: H, F, Cl, Br, I, OH, OR, NRR′, CH3, CN, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl, wherein R and R′ are each independently selected from the group consisting of: H, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl; wherein the Prot group is selected from the group consisting of: a methoxymethyl ether (MOM) group, a β-methoxyethoxymethyl ether (MEM) group, a methyl group (Me), a methyl thiomethyl (MTM) group, a benzyloxymethyl (BOM) group, a tetrahydropyranyl (THP) group, an ethoxyethyl (EE) group, a trityl (Tr) group, a methoxytrityl group, a benzene sulfonyl (Bs) group, a toluenesulfonyl (Ts) group, and a silicon-based protecting group.

### Claim 6

A method of treating a condition, comprising administering a pharmaceutically effective amount of BHQ-conjugate to a subject in need of treatment.

### Claim 7 (depends on 6)

The method of claim 6, wherein the conjugate is selection from the group consisting of: a serotonin (5HT), a capsaicinoid, and a catechol.

### Claim 8 (depends on 6)

The method of claim 6, wherein the BHQ-conjugate has the following structure:
wherein R1 is selected from the group consisting of: H, Br, F, Cl, I, and CN; and wherein R2 is selected from the group consisting of: H, F, Cl, Br, I, OH, OR, NRR′, CH3, CN, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl, wherein R and R′ are each independently selected from the group consisting of: H, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl.

### Claim 9

A method of releasing a conjugate, comprising:
exposing a BHQ-conjugate to a light energy, wherein the light energy interacts with the BHQ-conjugate and causes the conjugate to be released from the BHQ-conjugate.

### Claim 10 (depends on 9)

The method of claim 9, wherein the light energy is about 300 to 425 nm or 690-850 nm.

### Claim 11 (depends on 9)

The method of claim 9, wherein the BHQ-conjugate has the following structure:
wherein R1 is selected from the group consisting of: H, Br, F, Cl, I, and CN; and wherein R2 is selected from the group consisting of: H, F, Cl, Br, I, OH, OR, NRR′, CH3, CN, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl, wherein R and R′ are each independently selected from the group consisting of: H, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl.

### Claim 12

A pharmaceutical composition, comprising:
a pharmaceutically effective amount of a BHQ-conjugate.

### Claim 13 (depends on 12)

The pharmaceutical composition of claim 12, wherein the conjugate is selection from the group consisting of: a serotonin (5HT), a capsaicinoid, and a catechol.

### Claim 14 (depends on 12)

The pharmaceutical composition of claim 12, wherein the BHQ-conjugate is selected from the group consisting of: BHQ-O-5HT, BHQ-N-5HT, BHQ-capsaicin, BHQ-VNA (vanillyamide of n-nonanoic acid), BHQ-VAA, BHQ-dopamine, BHQ-epinephrine, BHQ-noreepinephrine, BHQ-tyrosine, BHQ-tyrosine(Fmoc), BHQ-hydroxytamoxifen, BHQ-morphine, BHQ-oripavine, BHQ-estriol, BHQ-estrone, and BHQ-estradiol.

### Claim 15 (depends on 12)

The pharmaceutical composition of claim 12, wherein the BHQ-conjugate has the following structure:
wherein R1 is selected from the group consisting of: H, Br, F, Cl, I, and CN; and wherein R2 is selected from the group consisting of: H, F, Cl, Br, I, OH, OR, NRR′, CH3, CN, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl, wherein R and R′ are each independently selected from the group consisting of: H, an unsubstituted or substituted alkyl, and unsubstituted or substituted aryl.