# US 10,502,729 B2 · Diagnostic methods, therapeutic agents and uses thereof

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- Number: US 10,502,729 B2
- Document ID: US10502729B2
- Status: Granted
- Kind: B2
- Application number: 15/548,854
- Filed: 2016-02-04
- Published: 2018-02-01
- Granted: 2019-12-10
- Earliest claimed: 2015-02-06
- Assignees: Metabolon, Inc.
- Applicants: Metabolon, Inc.
- Inventors: Luke Miller; Klaus Peter Adam; Michael V. Milburn; Jeffery E. Cobb; Anne M. Evans; Qibo Zhang
- Web page: https://patentgrep.com/patent/US10502729B2

## CPC

- G01N 33/50: Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing (measuring or testing processes involving enzymes or microorganisms, compositions or test papers therefor; processes for forming such compositions, condition responsive control in microbiological or enzymological processes C12Q)
- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- A61K 31/155: Amidines ([IMAGE cpc-sch-A61K-1029.gif]), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
- A61K 31/341: not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/485: Morphinan derivatives, e.g. morphine, codeine
- A61K 31/7048: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin {, digitoxin or digoxin}
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/50: for increasing or potentiating the activity of insulin
- C07D 307/33: in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C07K 16/44: against material not provided for elsewhere {, e.g. haptens, metals, DNA, RNA, amino acids}
- G01N 33/5008: {for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics}
- G01N 33/507: {Pancreatic cells}
- G01N 33/6893: {related to diseases not provided for elsewhere}
- C07K 2317/56: variable (Fv) region, i.e. VH and/or VL
- C07K 2319/00: Fusion polypeptide
- G01N 2800/042: Disorders of carbohydrate metabolism, e.g. diabetes, glucose metabolism
- G01N 2800/52: Predicting or monitoring the response to treatment, e.g. for selection of therapy based on assay results in personalised medicine; Prognosis
- 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)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)

## Abstract

The present invention provides a method for diagnosing a disease or disorder selected from the group consisting of insulin resistance, a metabolic disorder, diabetes and pre-diabetes in a subject. The method comprises the step of determining the level of a compound represented by structural formula (VI): or a salt thereof. Compositions and method of making thereof are also described.

## Claims

### Claim 1

A method of preparing a compound represented by the following formula:
or a salt thereof, comprising the steps of:
(1) isolating a compound of formula 3 from Ailanthus triphysa
(2) reacting the compound of formula 3 with an oxidizing reagent to give a compound of formula 4:
(3) reacting the compound of formula 4 with a reducing reagent to give a compound of formula 5:
(4) reacting the compound of formula 5 with sulfuric acid to give the compound of formula (VII).

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound of formula 3 is isolated by extracting the resins of Ailanthus triphysa with an organic solvent.

### Claim 3 (depends on 2)

The method of claim 2, wherein the organic solvent is hexane.

### Claim 4 (depends on 1)

The method of claim 1, wherein the oxidizing reagent is PCC.

### Claim 5 (depends on 1)

The method of claim 1, wherein the reducing reagent is LiAlH4 or NaBH4.

### Claim 6 (depends on 1)

The method of claim 1, wherein the compound of formula (VII) is labeled.