# US 9,434,756 B2 · Crystalline 4′-epidaunorubicin hydrochloride and use thereof

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- Number: US 9,434,756 B2
- Document ID: US9434756B2
- Status: Granted
- Kind: B2
- Application number: 14/459,850
- Filed: 2014-08-14
- Published: 2014-12-04
- Granted: 2016-09-06
- Earliest claimed: 2009-09-08
- Assignees: Medac Gesellschaft FüR Klinische SpezialpräParate Mbh
- Applicants: Heraeus Precious Metals GmbH & Co. KG
- Inventors: Tero Kunnari; Holger Bindernagel; Sascha Weiser; Andrew Lupton; Stefan Wallert
- Web page: https://patentgrep.com/patent/US9434756B2

## CPC

- C07H 15/252: Naphthacene radicals, e.g. daunomycins, adriamycins
- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

4′-epidaunorubicin hydrochloride is provided in a crystalline form which is stable and readily soluble. A process of producing the crystalline form includes crystallizing 4′-epidaunorubicin hydrochloride in a solvent system including (a) solvent A selected from C1 and C2 halogenated solvents and mixtures thereof, (b) solvent B selected from C1-C5 straight and branched alcohols and mixtures thereof, and (c) solvent C selected from C1-C5 straight and branched alcohols and mixtures thereof, wherein solvent C is selected to provide lower solubility to 4′-epidaunorubicin hydrochloride than solvent B. A method of producing an anthracycline using crystalline 4′-epidaunorubicin hydrochloride is also provided.

## Claims

### Claim 1

A method of producing an anthracycline, the method comprising using crystalline 4′-epidaunorubicin hydrochloride as an intermediate, wherein the crystalline 4′-epidaunorubicin hydrochloride is characterized by its powder X-ray diffraction pattern comprising the following characteristic peaks:
Diffraction Angle 2(theta)
5.13
7.64
12.18
16.77
17.00
19.86
21.82
22.58
23.03.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the crystalline 4′-epidaunorubicin hydrochloride is further characterized by its powder X-ray diffraction pattern comprising the following peaks:
Diffraction Angle
Relative intensity
2(theta)
P(%)
5.13
40.00-46.00
7.64
29.00-33.50
12.18
23.50-26.00
16.77
18.90-20.70
17.00
24.50-26.90
19.86
54.00-62.00
21.82
25.80-28.25
22.58
100
23.03
30.00-32.00.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the anthracycline is epirubicin.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the method comprises a step of dissolving the crystalline 4′-epidaunorubicin hydrochloride in methanol.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the method comprises a step of dissolving the crystalline 4′-epidaunorubicin hydrochloride in methanol.