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药物详细合成路线

Name Enoxacin;PD-107779;CI-919;AT-2266;Almitil;Enoxor;Penetrex;Comprecin;Flumark
Chemical Name 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
CAS 74011-58-8
Related CAS
Formula C15H17FN4O3
Structure
Formula Weight 320.32614
Stage 上市-1986
Company Dainippon Pharmaceutical (Originator)
Activity/Mechanism Antibacterial Drugs, ANTIINFECTIVE THERAPY, Quinolones
Syn. Route 1
Route 1
the reaction of 2,6-dichloro-3-nitropyridine (i) with n-ethoxycarbonylpiperidine (ii) by means of triethylamine in chcl gives 6-chloro-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (iii), which is treated with ethanolic nh3 at 120 c in a sealed tube to afford 6-amino-2-(4-ethoxycarbonyl-1-piperazinyl)-3-nitropyridine (iv). the acetylation of (iv) with acetic anhydride - acetic acid at 90 c yields the corresponding 6-acetamido derivative (v), which is reduced with h2 over pd/c in acetic acid giving 3-amino-6-acetamido-2-(4-ethoxycarbonyl-1-piperazinyl)pyridine (vi). the diazotation of (vi) with isoamyl nitrite (a) and tetrafluoroboric acid in ethanol affords 6-acetylamino-2-(4-ethoxycarbonylpiperazinyl)-3-pyridine diazonium tetrafluoroborate (vii), which by heat treatment at 120 c in toluene is converted into 6-acetylamino-2-(4-ethoxycarbonylpiperazinyl)-3-fluoropyridine (viii). the hydrolysis of (viii) with hcl in methanol yields the corresponding 6-aminopyridine derivative (ix), which is condensed with diethyl ethoxymethylenemalonate (x) by heating at 130 c to afford diethyl n-[2-(4-ethoxycarbonyl-1-piperazinyl)-3-fluoro-6-pyridinyl]aminomethylenemalonate (xi). the cyclization of (xi) by heating at 255 c yields ethyl 7-(4-ethoxycarbonyl-1-piperazinyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (xii), which is n-alkylated by means of ethyl iodide and k2co3 in hot dmf to afford ethyl 7-(4-ethoxycarbonyl-1-piperazinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (xiii). finally, this compound is hydrolyzed by means of naoh in refluxing ethanol.
List of intermediates No.
(4s)-4-hydroxy-4-methyl-1h-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione (i)
5-(benzyloxy)-2,2,4,6,7-pentamethyl-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2,3-dihydro-1-benzofuran (x)
methyl 5-[(3ar,4r,5r,6as)-5-(acetoxy)-4-[(e,3s,4s)-3-(acetoxy)-4-methyl-1-octenyl]hexahydro-2h-cyclopenta[b]furan-2-ylidene]-6-[(chlorosulfonyl)amino]-6-oxohexanoate (ii)
2-bromo-1-phenyl-1-ethanone (iii)
2-[(2-[[3-(hydroxymethyl)-2-pyridinyl]amino]ethyl)(methyl)amino]-1-phenyl-1-ethanone (iv)
8-methyl-6a-phenyl-7,8,9,10-tetrahydro-5h,6ah-pyrazino[2,1-b]pyrido[2,3-d][1,3]oxazine (v)
[2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinyl]methanol (vi)
2-(4-methyl-2-phenyl-1-piperazinyl)nicotinic acid (a)
[2-(4-methyl-2-phenyl-1-piperazinyl)-3-pyridinyl]methanol (vii)
acetyl chloride (viii)
methyl 5-acetyl-2-hydroxybenzoate (ix)
methyl 5-(2-bromoacetyl)-2-hydroxybenzoate (xi)
methyl 5-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]acetyl)-2-hydroxybenzoate (xii)
4-(2-[benzyl[6-(4-phenylbutoxy)hexyl]amino]-1-hydroxyethyl)-2-(hydroxymethyl)phenol (xiii)
Reference 1:
    matsumoto, j.; et al. (aventis pharma sa; dainippon pharmaceutical co., ltd.); novel naphthyridine derivatives, intermediates thereof, processes for preparation thereof and use thereof. ep 0009425; es 483629; us 4359578 .
Reference 2:
    blancafort, p.; serradell, m.n.; mealy, n.e.; castaner, j.; leeson, p.a.; at-2266. drugs fut 1981, 6, 3, 129.

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依诺沙星;英文名Enoxacin;PD-107779;CI-919;AT-2266;Almitil;Enoxor;Penetrex;Comprecin;Flumark;CAS[74011-58-8]

 
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