Browse Prior Art Database

Crystalline form of 1-methyl-5-amino-2-benzimidazolebutyric acid ethyl ester

IP.com Disclosure Number: IPCOM000200259D
Publication Date: 2010-Oct-03
Document File: 3 page(s) / 82K

Publishing Venue

The IP.com Prior Art Database

This text was extracted from a PDF file.
This is the abbreviated version, containing approximately 57% of the total text.

Page 01 of 3

Crystalline form of 1-methyl-5-amino-2-benzimidazolebutyric acid ethyl ester

1-methyl-5-amino-2-benzimidazolebutyric acid ethyl ester (referred as "BBN") having the following formula;

N

N

is an intermediate of the synthesis of 5-[bis(2-chloroethyl)amino]-1-methyl-1H- benzimidazole-2-butanoic acid hydrochloride (referred as "BNT HCl"), having the following formula;

O

    which belongs to the family of drugs called alkylating agents. BNT HCl is the substance in the treatment of leukemia, chronic lymphocytic leukemia (CLL) and also being studied for the treatment of sarcoma.

A crystalline form of BBN was found and is described herein below.

BBN crystalline form

The crystalline form of BBN, described herein has diffraction peaks at about 8.9,
12.1, 13.1, 13.7, 18.0, 18.5, 19.0, 19.3, 22.0 and 24.8 deg 2-theta ± 0.2 deg 2-theta. In addition above crystalline form can be further characterized by XRPD pattern and peak list described on Figure 1 and Table 1.

O

H2N

OEt

Cl

OH

HCl

N

N

N

Cl


Page 02 of 3

Figure 1: A powder XRD pattern and peak list of crystalline BBN

Intensity (cps)

600

500

400

300

200

100

0

5 10 15 20 25 30 35

2Theta (°)

Table 1: A powder XRD peaks list of crystalline BBN

  Peak Position

[°2Th.]

Relative Intensity

[%]

Relative Intensity

[%]

8.9 47 27.0 8
12.1 28 27.6 6
13.1 11 28.1 4
13.7 52 28.4 9
18.0 31 29.0 2
18.5 21 29.7 2
19.0 26 30.7 1
19.3 15 31.6 3
21.7 5 32.2 3
22.0 18 33.3 2
22.4 1 34.5 1
23.1 1 35.6 1
24.3 5 36.1 2
24.8 100 36.9 1
25.2 6 37.5 1
25.6 2 38.1 1
26.3...