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Process for preparing telmisartan

A technology of telmisartan and alkyl, which is applied in the field of preparation of telmisartan intermediates, can solve the problems that the final product is difficult to filter, wash and separate

Inactive Publication Date: 2010-06-16
新梅斯托克尔卡托瓦纳兹德拉韦尔公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The end product of the process is difficult to filter, wash and separate
These properties present a barrier to efficient mass production of

Method used

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  • Process for preparing telmisartan
  • Process for preparing telmisartan
  • Process for preparing telmisartan

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preparation example Construction

[0111] Another preferred aspect of the present invention is the following method for preparing intermediates of telmisartan derivatives, the intermediates of said telmisartan derivatives are substituted in 4'-[(2-n-propyl-4- The 2-position of the biphenyl group of methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)-methyl]-biphenyl, these derivatives are represented by formula 3" Representative, the method includes the following steps:

[0112] a) alkylating compound 11" to form compound 10", and

[0113]

[0114] b) condensation to form compound 3"

[0115]

[0116] 10″or R9″(R 4 =H)

[0117] in

[0118] R 1 is C 1 -C 6 alkyl,

[0119] R 2 is C 1 -C 6 alkyl,

[0120] R 3 is C 1 -C 6 alkyl,

[0121] R 4 is CONR 5 , where R 5 is H or C 1 -C 3 alkyl,

[0122] Z is a group capable of being converted into a tetrazolyl or carboxyl, which may be selected from CN and COR 6 , where R 6 Can be N(R) 2 OR 1 , where R is H, C 1 -C 6 alkyl or benzyl, a...

Embodiment 1

[0267] Preparation of N-(2-aminophenyl)-4-(butanylamino)-N,3-dimethyl-5-nitrobenzamide (compound 7):

[0268] To 3.9g (20mmol) N-methylbenzene-1,2-diamine dihydrochloride and 10ml CH 2 Cl 2Add 1.6ml of pyridine (20mmol) to the mixture, and stir at room temperature to obtain a free N-methylbenzene-1,2-diamine solution. The resulting solution was added to a mixture of 2.66 g (10 mmol) of compound 8, 3.24 g (20 mmol) of CDI and 60 ml of THF, stirred for 3 h and filtered. The wet filter cake was dried in an oven to obtain 2.26 g of solid compound 7 (yield: 61%).

[0269] 1 H NMR (300MHz, DMSO-d 6 ): δ8.33(s, 1H), 8.19(s, 1H), 7.11(d, 2H, J=6.9Hz), 6.63(d, 2H, J=7.8Hz), 2.70(s, 3H), 2.30 ~2.36(m, 5H), 1.60(m, 2H), 0.93(t, 3H, J=7.5Hz); ESI-MS: 369[M-1] -

Embodiment 2

[0271] Preparation of N-(2-methyl-4-(1-methyl-1H-benzo[d]imidazol-2-yl)-6-nitrophenyl)butanamide (compound 6):

[0272] A mixture of 370 mg (1 mmol) of compound 7 and 5 ml of pyridine was heated to reflux and stirred for 5 h. The mixture was diluted with ethyl acetate, washed with water, Na 2 SO 4 After drying and filtering, the solvent was removed under vacuum to obtain 0.3 g of compound 6 (yield: 85%).

[0273] ESI-MS: 353[M+1] +

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Abstract

Novel processes for preparing a telmisaitan nitrile intermediate (4'-[{2-n-propyl-4- methyI-6-f l-methyJbenzimidazol-2-yl}-benzimidazol- l -yl}-methyl}-biphenyl-2-nitrile} and further converting it to telmisaitan and / or salts thereof are disclosed.

Description

technical field [0001] The present invention relates to substitution in (4'-[(2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)-methyl ]-biphenyl group) the preparation method of the telmisartan intermediate of the biphenyl group 2, the present invention also relates to the method that this intermediate is converted into telmisartan and / or its salt. The method according to the invention is cost and time efficient and produces telmisartan in high yield and high quality. Background technique [0002] The chemical name of telmisartan is 4'-[(2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)-benzimidazol-1-yl)- Methyl]-biphenyl-2-carboxylic acid, whose structure is shown in formula 1, it is the non-peptide antagonist of angiotensin II receptor subtype 1 (AT 1 - antagonists), for the treatment of hypertension. It can be used alone or in combination with other pharmaceutically active compounds such as hydrochlorothiazide. [0003] [0004] Telmisartan is ...

Claims

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Application Information

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IPC IPC(8): C07D235/08A61K31/4184C07D235/18A61P9/12C07D235/20
CPCC07D235/08C07D235/20C07D235/18A61P9/12
Inventor 罗克·楚佩特蒋翔锐欧洋柳永建陈伟铭吴明军沈敬山西尔沃·祖普契奇格雷戈尔·塞德马克
Owner 新梅斯托克尔卡托瓦纳兹德拉韦尔公司