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Impurities of 5-[[4-[(2, 3-Dimethyl-2H-indazol-6-yl) methylamino]-2-pyrimidinyl] amino]-2-methyl-benzolsulfonamide

IP.com Disclosure Number: IPCOM000193371D
Publication Date: 2010-Feb-21
Document File: 6 page(s) / 36K

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The IP.com Prior Art Database

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This is the abbreviated version, containing approximately 36% of the total text.

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Impurities of 5-[[4-[(2, 3-Dimethyl-2H-indazol-6-yl) methylamino]-2- pyrimidinyl] amino]-2-methyl-benzolsulfonamide

    5-[[4-[(2, 3-Dimethyl-2H-indazol-6-yl) methylamino]-2-pyrimidinyl] amino]- 2-methyl-benzolsulfonamide ("PPB") of the following chemical structure:

N

N

N

  N
N N

H S

O O

NH2

is a tyrosine kinase inhibitor, indicated for the treatment of patients with advanced renal cell carcinoma and is administered as an HCl salt.

    Herein will be described different impurities which are formed during the preparation of PPB.

3-methyl-2H-indazol-6-amine:

    3-methyl-2H-indazol-6-amine("Des-Me-DMAD"), having the following formula:

NNH

H2N

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 147.18.

2,3-dimethyl-6-nitro-2H-indazole :

2,3-dimethyl-6-nitro-2H-indazole ("DMND"), having the following formula:

N

O2N

N

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 191.19.

N-(4-chloropyrimidin-2-yl)-2, 3-dimethyl-2H-indazol-6-amine:

    N-(4-chloropyrimidin-2-yl)-2, 3-dimethyl-2H-indazol-6-amine ("4-CPDMI"), having the following formula:

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N

N

C

H

N

N

N

l

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 273.72.

N2,N4-bis(2,3-dimethyl-2H-indazol-6-yl)pyrimidine-2,4-diamine:

    N2,N4-bis(2,3-dimethyl-2H-indazol-6-yl)pyrimidine-2,4-diamine("bis- PDMI"), having the following formula:

NNH

N

N

H

N

N

N

HN

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 398.46. N2-(2-chloropyrimidin-4-yl)-N2,N4-bis(2,3-dimethyl-2H-indazol-6-yl)-N4- methylpyrimidine-2,4-diamine:

    N2-(2-chloropyrimidin-4-yl)-N2,N4-bis(2,3-dimethyl-2H-indazol-6-yl)-N4- methylpyrimidine-2,4-diamine ("PMI-CPDMI"), having the following formula:

N

N

N

N

N N

N

N

N N

C

l

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 525.01. N-(4-chloropyrimidin-2-yl)-N,2,3-trimethyl-2H-indazol-6-amine:

    N-(4-chloropyrimidin-2-yl)-N,2,3-trimethyl-2H-indazol-6-amine ("4-CPMI"), having the following formula:

N

N

N

C

N

N

l

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 287.75. 5-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)(4-(2,3- dimethyl-2H-indazol-6-ylamino)pyrimidin-2-yl)amino)-2- methylbenzenesulfonamide:

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    5-((4-((2,3-dimethyl-2H-indazol-6-yl)(methyl)amino)pyrimidin-2-yl)(4-(2,3- dimethyl-2H-indazol-6-ylamino)pyrimidin-2-yl)amino)-2-methylbenzenesulfonamide ("PPB-PDMI"), having the following formula:

N

N

N

H2N

N N N

S

O

O

N N

N

N

N

H

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 674.78 . 2-methyl-5-benzenesulfonamide:

2-methyl-5-benzenesulfonamide("NMBS"), having the following formula:

NO2

H2N

O

O

S

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 216.21. 5-(4-(2,3-dimethyl-2H-indazol-6-ylamino)pyrimidin-2-ylamino)-2- methylbenzenesulfonamide:

    5-(4-(2,3-dimethyl-2H-indazol-6-ylamino)pyrimidin-2-ylamino)-2- methylbenzenesulfonamide("Des-Me-PPB"), having the following formula:

N

H

N

N

H2N

N N NH

S

O

O

is characterized by a mass spectrum of MS-ESI [M+H]+ = m/z 423.49.

Examples:

Preparation of PPB HCl:

...