# US 11,305,010 B2 · Synthetic opioid vaccine

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- Number: US 11,305,010 B2
- Document ID: US11305010B2
- Status: Granted
- Kind: B2
- Application number: 16/071,199
- Filed: 2017-01-18
- Published: 2021-05-06
- Granted: 2022-04-19
- Earliest claimed: 2016-01-21
- Assignees: The Scripps Research Institute
- Applicants: The Scripps Research Institute
- Inventors: Kim D. Janda
- Web page: https://patentgrep.com/patent/US11305010B2

## CPC

- A61K 39/385: Haptens or antigens, bound to carriers
- C07K 1/00: General methods for the preparation of peptides {, i.e. processes for the organic chemical preparation of peptides or proteins of any length}
- A61K 39/0013: {Therapeutic immunisation against small organic molecules, e.g. cocaine, nicotine}
- A61K 39/395: Antibodies (agglutinins A61K38/36 {; as drug carriers A61K47/50}); Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K 47/643: {Albumins, e.g. HSA, BSA, ovalbumin or a Keyhole Limpet Hemocyanin [KHL]}
- A61K 47/6829: {Bacterial toxins, e.g. diphteria toxins or Pseudomonas exotoxin A}
- A61P 25/30: for treating abuse or dependence
- A61P 37/04: Immunostimulants
- C07K 16/44: against material not provided for elsewhere {, e.g. haptens, metals, DNA, RNA, amino acids}
- A61K 2039/55505: {Inorganic adjuvants}
- A61K 2039/55561: {CpG containing adjuvants; Oligonucleotide containing adjuvants}
- C07K 2317/92: Affinity (KD), association rate (Ka), dissociation rate (Kd) or EC50 value
- 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)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Fentanyl is an addictive prescription opioid that is over 80 times mora potent than morphine. The synthetic nature of fentanyl has enabled the creation of dangerous “designer drug’ analogues that escape toxicology screening, yet display comparable potency to the parent drug. Alarmingly, a large number of fatalities have been linked to overdose of fentanyl derivatives. Herein, we report an effective immunotherapy for reducing the psychoactive effects of fentanyl class drugs. A single conjugate vaccine was created that elicited high levels of antibodies with cross-reactivity for a wide panel of fentanyl analogues, Moreover, vaccinated mice gained significant protection from lethal fentanyl doses. Lastly, a surface plasmon resonance (SPR)-based technique was established enabling drug specificity profiling of antibodies derived directly from serum. Our newly developed fentanyl vaccine and analytical methods may assist in the battle against synthetic opioid abuse.

## Claims

### Claim 1

A hapten conjugate of formula (I):
wherein
R1 is —CH2CH2C(═O)X,
X is a tetanus toxoid; wherein the tetanus toxoid forms an amide bond with the —C(═O)— group of —CH2CH2C(═O)— in R1,
R2 is —H or a (C1-C4)alkyl group,
R3 is —H or a (C1-C4)alkyl group, and
R4 is —H or a (C1-C4)alkyl group.

### Claim 2 (depends on 1)

A vaccine comprising the hapten conjugate of claim 1 and an adjuvant.

### Claim 3 (depends on 2)

The vaccine of claim 2, wherein the vaccine is effective in eliciting an IgG antibody response for a fentanyl class drug.

### Claim 4 (depends on 2)

A method of effectively minimizing a concentration of a fentanyl class drug in a patient in need thereof, comprising administering to the patient an effective dose of the vaccine of claim 2.

### Claim 5 (depends on 4)

The method of claim 4, wherein administering the effective dose of the vaccine imparts protection to the patient from an otherwise lethal dose of a fentanyl class drug.

### Claim 6 (depends on 4)

The method of claim 4, wherein administering the effective does of the vaccine to the patient reduces the addiction liability and overdose potential of the fentanyl class drug.

### Claim 7

A hapten conjugate having the formula: