e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

An improved, scalable, and impurity-free process for tolterodine tartrate

…, N Srinivasan, KS Reddy, M Ramakrishna…

Index: Srinivas, Keesari; Srinivasan, Neti; Reddy, Kikkuru Srirami; Ramakrishna, Muddasani; Reddy, Chinta Raveendra; Arunagiri, Muthulingam; Kumari, Routhu Lalitha; Venkataraman, Sundaram; Mathad, Vijayavitthal T. Organic Process Research and Development, 2005 , vol. 9, # 3 p. 314 - 318

Full Text: HTML

Citation Number: 21

Abstract

Tolterodine tartrate is an anticholinergic muscle relaxant used to treat urinary frequency, urinary urgency, and incontinence in people with unstable bladders. An improved, cost- effective, and impurity-free process for tolterodine tartrate suitable for large-scale commercial production is described here by addressing various scale-up and impurity issues.

6-Methyl-4-phenyl-2-chromanone Structure

6-Methyl-4-phen...

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate Structure

methyl 3-(2-ben...

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

Benzenepropanol, 5-methyl-γ-phenyl-2-(phenylmethoxy) Structure

Benzenepropanol...

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate Structure

3-(2-benzyloxy-...

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate Structure

3-(2-benzyloxy-...

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

~79%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

Cinnamic acid Structure

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

p-Cresol Structure

~%

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

4-methyl-2-[3-[[3-(5-methyl-2-phenylmethoxyphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]phenol Structure

4-methyl-2-[3-[...

~73%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

Cinnamic acid Structure

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

p-Cresol Structure

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

6-Methyl-4-phenyl-2-chromanone Structure

6-Methyl-4-phen...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate Structure

methyl 3-(2-ben...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

Benzenepropanol, 5-methyl-γ-phenyl-2-(phenylmethoxy) Structure

Benzenepropanol...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

Benzenepropanamine, 5-methyl-N-(1-methylethyl)-γ-phenyl-2-(phenylmethoxy) Structure

Benzenepropanam...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate Structure

3-(2-benzyloxy-...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate Structure

3-(2-benzyloxy-...

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

~%

2-[3-[[3-(2-hydroxy-5-methylphenyl)-3-phenylpropyl]-propan-2-ylamino]-1-phenylpropyl]-4-methylphenol Structure

2-[3-[[3-(2-hyd...

Benzenepropanamine, 5-methyl-N-(1-methylethyl)-γ-phenyl-2-(phenylmethoxy) Structure

Benzenepropanam...

~87%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

Cinnamic acid Structure

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

p-Cresol Structure

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

6-Methyl-4-phenyl-2-chromanone Structure

6-Methyl-4-phen...

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate Structure

methyl 3-(2-ben...

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

Benzenepropanol, 5-methyl-γ-phenyl-2-(phenylmethoxy) Structure

Benzenepropanol...

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...

3-(2-benzyloxy-5-methylphenyl)-3-phenylpropyl-p-toluene sulphonate Structure

3-(2-benzyloxy-...

~%

rac Desisopropyl Tolterodine Structure

rac Desisopropy...