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药物详细合成路线

Name Lansoprazole;AG-1749;ABT-006;CG-4801;A-65006;Ogast;Lanzor;Lanzo;Agopton;Opiren;Bamalite;Takepron;Lansox;Lansox;Ogastro;Monolitum;Prevacid;Zoton
Chemical Name 2-[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethylsulfinyl]-1H-benzimidazole
      2-(2-Benzimidazolylsulfinylmethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine
CAS 103577-45-3
Related CAS
Formula C16H14F3N3O2S
Structure
Formula Weight 369.36808
Stage 上市-1992
Company Takeda (Originator), Almirall Prodesfarma (Licensee), Salvat (Licensee), TAP (Licensee), Wyeth Pharmaceuticals (Licensee)
Activity/Mechanism Agents for Gastritis, Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Esophageal Diseases, Treatment of, Gastric Antisecretory Drugs, Gastroesophageal Reflux Disease, Agents for, GASTROINTESTINAL DRUGS, Non-Ulcer Dyspepsia, Agents for, H+/K+-ATPase Inhibitors
Syn. Route 2
Route 1
the condensation of 2,3-dimethyl-4-nitropyridine n-oxide (i) with 2,2,2-trifluoroethanol (ii) by means of k2co3 in hot hmpt gives 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine n-oxide (iii), which by isomerization in acetic anhydride at 100 c is converted to 2-(hydroxymethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (iv). the reaction of (iv) with socl2 in refluxing chcl3 affords the corresponding chloromethyl derivative (v), which is condensed with 2-mercaptobenzimidazole (vi) by means of sodium methoxide in refluxing methanol to yield 2-(2-benzimidazolylthiomethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin (vii). finally, this compound is oxidized with m-chloroperbenzoic acid in chcl3.
List of intermediates No.
methyl 3,5-bis(benzyloxy)benzoate (vi)
(1s,4r,6r,8s,9s,13s,15r)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-6-(4-methoxyphenyl)-5,7,10,12-tetraoxa-11lambda(6)-thiapentacyclo[13.4.1.0(1,9).0(4,9).0(8,13)]icosane-11,11,20-trione
n-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]propanamide; n-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]propanamide (i)
2-bromoacetonitrile (ii)
2-[[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl](propyl)amino]acetonitrile (iii)
n(1)-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]-n(1)-propyl-1,2-ethanediamine; n-(2-aminoethyl)-n-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]-n-propylamine (iv)
(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenamine; (2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenylamine (v)
ethyl 1-chloro-7-methoxy-9-oxo-9,10-dihydro-4-acridinecarboxylate (vii)
Reference 1:
    makino, t.; tabata, t.; hirai, s.; stabilized pharmaceutical composition comprising a benzimidazole compound, its production and its use as an antiulcer agent.. ep 237200; jp 87277322 .
Reference 2:
    nohara, a.; maki, y. (takeda chemical industries, ltd.); pyridine derivs. and their production. au 8545895; ep 0174726; es 8607288; jp 1986050978; us 4628098; us 4689333 .
Reference 3:
    prous, j.; castaner, j.; lansoprazole < prop inn >. drugs fut 1989, 14, 7, 625.

Route 2
the chlorination of 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine-n-oxide (i) with trichloroisocyanuric acid in hot chloroform gives the 2-chloromethyl derivative (ii), which is condensed with 2-mercapto-1h-benzimidazole (iii) by means of naoh in methanol to yield the adduct (iv). the reaction of (iv) with pcl3 and acetic acid eliminates the n-oxide group, affording the sulfanylmethylpyridine (v). finally, this compound is oxidized with tert-butyl hydroperoxide (vi) in ethanol to provide the target sulfoxide.alternatively, the intermediate adduct (iv) can also be obtained as follows: the chlorination of 2,3-dimethyl-4-nitropyridine-n-oxide (vii) with trichloroisocyanuric acid as before gives the chloromethyl derivative (viii), which is condensed with 2-mercapto-1h-benzimidazole (iii) as before to yield the adduct (ix). finally, this compound is treated with 2,2,2-trifluoroethanol (x), benzyltrimethylammonium chloride and k2co3 in acetonitrile to afford the target intermediate (iv).
List of intermediates No.
methyl 3,5-bis(benzyloxy)benzoate (iii)
n-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]propanamide; n-[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]propanamide (vii)
2-bromoacetonitrile (x)
2-[[(2r)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl](propyl)amino]acetonitrile (i)
ethyl 1-chloro-7-methoxy-9-oxo-9,10-dihydro-4-acridinecarboxylate (v)
(2s)-2-(1,3-dioxo-1,3-dihydro-2h-isoindol-2-yl)-3-[2-(3-methyl-2-butenyl)-1h-indol-3-yl]propionic acid (vi)
2-(4-nitrophenyl)-1h-benzimidazole-5-carboxylic acid (ii)
2-(4-nitrophenyl)-n-(2-pyridinyl)-1h-benzimidazole-5-carboxamide (iv)
2-(4-aminophenyl)-n-(2-pyridinyl)-1h-benzimidazole-5-carboxamide (viii)
tricyclo[3.3.1.1~3,7~]decane-1-carbonyl chloride (ix)
Reference 1:
    montserrat vidal, c.; serra macia, x. (laboratorios salvat sa); intermediate for the synthesis of lansoprazole and process for obtaining it. es 2063705 .

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名兰索拉唑;英文名Lansoprazole;AG-1749;ABT-006;CG-4801;A-65006;Ogast;Lanzor;Lanzo;Agopton;Opiren;Bamalite;Takepron;Lansox;Lansox;Ogastro;Monolitum;Prevacid;Zoton;CAS[103577-45-3]

 
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