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Name Almotriptan;PNU-180638;LAS-31416;Almogran;Axert
Chemical Name 3-[2-(Dimethylamino)ethyl]-5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indole
CAS 154323-57-6
Related CAS
Formula C17H25N3O2S
Structure
Formula Weight 335.4717
Stage 上市-2000
Company Almirall Prodesfarma (Originator), Kwizda (Marketer), Nycomed Pharma (Marketer), Bayer (Licensee), Lundbeck (Licensee), Ortho-McNeil (Licensee), Solvay (Licensee)
Activity/Mechanism ANALGESIC AND ANESTHETIC DRUGS, Antimigraine Drugs, 5-HT1B Agonists, 5-HT1D Agonists
Syn. Route 2
Route 1
almotriptan has been obtained by several related ways:1) the hydrolysis of 4-chlorobutyraldehyde dimethylacetal (i) with hcl gives the corresponding aldehyde (ii), which is condensed with 4-(1-pyrrolidinylsulfonylmethyl)phenylhydrazine (iii) by means of hcl in methanol/water, giving 3-(2-aminoethyl)-5-(1-pyrrolidinylsulfonylmethyl)-1h-indole (iv). finally, this compound is methylated with formaldehyde and nabh4 in methanol.2) the direct condensation of 4-chlorobutyraldehyde dimethylacetal (i) with 4-(1-pyrrolidinylsulfonylmethyl)phenylhydrazine (iii) by means of hcl in water also yields intermediate 3-(2-aminoethyl)-5-(1-pyrrolidinylsulfonylmethyl)-1h-indole (iv).3) the decarboxylation of 3-[2-(dimethylamino)ethyl]-5-(1-pyrrolidinylsulfonylmethyl)-1h-indole-2-carboxylic acid (v) catalyzed by means of cu2o in quinoline at 190 c also gives almotriptan.
List of intermediates No.
(2s)-1-(1,3-benzodioxol-5-yl)-2-propanol (i)
methyl 4-[4-(7-ethyl-4-methyl-1-benzofuran-2-yl)-4-oxobutanoyl]benzoate (ii)
methyl 4-[5-(7-ethyl-4-methyl-1-benzofuran-2-yl)-1h-pyrrol-2-yl]benzoate (iii)
4,7-dimethyl-1-benzofuran-2-carbaldehyde (iv)
methyl 4-[4-(4,7-dimethyl-1-benzofuran-2-yl)-4-oxobutanoyl]benzoate (v)
Reference 1:
    fernandez forner, d.; puig duran, c.; prieto soto, j.; vega noverola, a.; moragues mauri, j. (almirall prodesfarma, sa); indol derivs. for the treatment of migraine. ep 0605697; jp 1994511261; us 5565447; wo 9402460 .
Reference 2:
    fernandez forner, m.d.; puig duran, c.; crespo crespo, m.i.; moragues mauri, j. (almirall prodesfarma, sa); process for the preparation of indole derivs.. es 2084560 .
Reference 3:
    pujol noguera, f.; crespo crespo, m.i.; puig duran, c.; fernandez forner, d.; moragues mauri, j. (almirall prodesfarma, sa); new indole derivs.. es 2056025 .

Route 2
4) the intermediate 4-(1-pyrrolidinylsulfonylmethyl)phenylhydrazine (iii) can be obtained as follows: the condensation of pyrrolidine (vi) with 1-(4-nitrobenzylsulfonyl)chloride (vii) in dichloromethane gives the expected sulfonamide (viii), which is reduced with h2 over rani in dmf, yielding 4-(1-pyrrolidinylsulfonylmethyl)aniline (ix). the diazotation of (ix) with nano2/hcl affords the corresponding diazo compound (x), which is finally reduced to the target intermediate (iii) with sncl2/hcl.
List of intermediates No.
phenyl 2-phenyl-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridin-8-yl sulfide; 2-phenyl-8-(phenylsulfanyl)-2,3,5,6,7,8-hexahydroimidazo[1,2-a]pyridine (vi)
methyl 4-[5-(7-ethyl-4-methyl-1-benzofuran-2-yl)-1h-pyrrol-2-yl]benzoate (iii)
4-chloro-1-(4-fluorophenyl)-1-butanone (vii)
1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]-4-piperidinol (viii)
1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]-4-piperidinone (ix)
n-(4-bromophenyl)(trimethyl)silanamine; n-(4-bromophenyl)-n-(trimethylsilyl)amine (x)
Reference 1:
    fernandez-forner, d.; new aniline derivatives as key intermediates in th. res disclosure 1998, 412, 1088.

全民突击安卓跟苹果系统可以PK吗 www.uxeea.icu 來源:藥化網

作者:藥化小編

摘要:本文合成路線介紹的是藥物中文名阿莫曲普坦;英文名Almotriptan;PNU-180638;LAS-31416;Almogran;Axert;CAS[154323-57-6]

 
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