# US 8,771,964 B2 · Compositions and methods for detection of methadone metabolite

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- Number: US 8,771,964 B2
- Document ID: US8771964B2
- Status: Granted
- Kind: B2
- Application number: 13/364,718
- Filed: 2012-02-02
- Published: 2013-08-08
- Granted: 2014-07-08
- Earliest claimed: 2012-02-02
- Assignees: Siemens Healthcare Diagnostics Inc.
- Applicants: Bhalchandra Lele
- Inventors: Bhalchandra Lele
- Web page: https://patentgrep.com/patent/US8771964B2

## CPC

- C07K 16/40: against enzymes
- C07K 16/44: against material not provided for elsewhere {, e.g. haptens, metals, DNA, RNA, amino acids}
- G01N 33/9486: {Analgesics, e.g. opiates, aspirine}
- 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)
- 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

Methods and reagents are disclosed for conducting assays for EDDP. The reagents include a moiety selected from the group consisting of poly(amino acid) label moieties, non-poly (amino acid) label moieties, poly(amino acid) immunogenic carriers, non-poly(amino acid) immunogenic carriers, non-label poly(amino acid) moieties, and non-immunogenic carrier poly(amino acid) moieties linked to 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine at the 3-position of one of the phenyl rings. Antibodies produced from immunogenic EDDP conjugates and labeled EDDP conjugates are employed in assays for determining the presence and/or amount of EDDP in samples suspected of containing EDDP.

## Claims

### Claim 1

A compound comprising a moiety, selected from the group consisting of a poly(amino acid) label moiety, a non-poly(amino acid) label moiety, a poly(amino acid) immunogenic carrier moiety, a non-poly(amino acid) immunogenic carrier moiety, a non-label poly(amino acid) moiety and a non-immunogenic carrier poly(amino acid) moiety, linked to 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine at the 3-position of one of the phenyl rings by means of the terminal oxygen atom of the linking group —(CH2)C(O)NH(CH2)(CH2)NHC(O)(CH2)O—.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein the moiety is the poly(amino acid) label moiety that is an enzyme or the non-poly(amino acid) label moiety selected from the group consisting of polynucleotides coding for a catalyst, promoters, dyes, fluorescent molecules, chemiluminescent molecules, coenzymes, enzyme substrates, radioactive groups, small organic molecules, amplifiable polynucleotide sequences and particles.

### Claim 3

A compound of the formula:
wherein:
E is L−Q wherein L is —(CH2)C(O)NH(CH2)(CH2)NHC(O)(CH2)—, and wherein E is linked through the terminal oxygen atom of L, and Q is a halogen, a poly(amino acid) label moiety, a non-poly(amino acid) label moiety, a poly(amino acid) immunogenic carrier moiety, a non-poly(amino acid) immunogenic carrier moiety, a non-label poly(amino acid) moiety and a non-immunogenic carrier poly(amino acid) moiety; and
J and G are taken together to form a spiro linked pyrrolidine ring.

### Claim 4 (depends on 3)

The compound according to claim 3 wherein the poly(amino acid) label moiety is an enzyme.

### Claim 5 (depends on 3)

A method for determining 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine in a sample suspected of containing 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, the method comprising:
(a) providing in combination in a medium:
(i) the sample,
(ii) an antibody for 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, and
(iii) the compound according to claim 3 wherein Q is the poly(amino acid) label moiety or the non-poly(amino acid) label moiety, and
(b) examining the medium for one or both of the presence and amount of a complex comprising 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine and the antibody for 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine, the presence and/or the amount thereof indicating the presence and/or amount of 2-ethylidene-1,5-dimethyl- 3,3-diphenylpyrrolidine in the sample.

### Claim 6 (depends on 3)

A kit comprising an antibody for 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine and the compound according to claim 3.