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药物详细合成路线

Name Dexanabinone;Dexanabinol;PRS-211007;HU-211
Chemical Name (+)-7-Hydroxy-DELTA6-tetrahydrocannabinol dimethylheptyl homolog
      (+)-(S,S)-6,6-Dimethyl-(1,1-dimethylheptyl)-1-hydroxy-9-(hydroxymethyl)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran
CAS 112924-45-5
Related CAS
Formula C25H38O3
Structure
Formula Weight 386.57981
Stage III 期临床
Company Pharmos (Originator)
Activity/Mechanism Cognition Disorders, Treatment of, Extrapyramidal Disorders, Treatment of, Immunologic Neuromuscular Disorders, Treatment of, Multiple Sclerosis, Agents for, NEUROLOGIC DRUGS, Neurologic Drugs (Miscellaneous), Tardive Dyskinesia, Treatment of, Antioxidants, Cannabinoid Receptor Agonists, NMDA Antagonists
Syn. Route 1
Route 1
the grignard reaction of ethyl heptanoate (i) with deuterated methylmagnesium iodide (ii) in ether gives deuterated 2-methyl-2-octanol (iii), which is treated with deuterium oxide to yield heptadeuterated 2-methyl-2-octanol (iv). the condensation of (iv) with monodeuterated 2,6-dimethoxyphenol (v) (obtained by treatment of 2,6-dimethoxyphenol (vi) with deuterium oxide) by means of deuterated trifluoromethylsulfonic acid affords the alkylated phenol (vii), which is phosphorylated with diethyl phosphite and triethylamine giving the phosphate (viii). the reduction of (viii) with li/nh3 yields the deuterated dimethoxybenzene (ix), which is demethylated with boron tribromide in dichloromethane to afford the deuterated resorcinol (x). the condensation of (x) with alpha-pinene-3,10-diol 10-o-pivalic ester (xi) by means of boron trifluoride etherate in methylene chloride gives the deuterated target compound as its monopivalic ester (xii), which is finally treated with lialh4 in thf to eliminate the ester group.
List of intermediates No.
(2s,5r,6r)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (+)-6-aminopenicillanic acid (i)
5-(2-chlorophenyl)-7-nitro-1,3-dihydro-2h-1,4-benzodiazepine-2-thione (ii)
2-[[5-(2-chlorophenyl)-7-nitro-3h-1,4-benzodiazepin-2-yl]amino]acetic acid (iii)
1,4-dihydroestronemethylether; (8r,9s,13s,14s)-3-methoxy-13-methyl-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydro-17h-cyclopenta[a]phenanthren-17-one (iv)
3-methoxyspiro[estra-2,5(10)-diene-17(s),2-oxirane] (vi)
2-[(8r,9s,13s,14s,17r)-17-hydroxy-13-methyl-3-oxo-2,3,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]acetonitrile (v)
4-methyl-4-(n-methylaminoethyl)-6-methoxy-3,4-dihydronaphthalene-1(2h)-one; (4r)-6-methoxy-4-methyl-4-[2-(methylamino)ethyl]-3,4-dihydro-1(2h)-naphthalenone (vii)
1,4-dimethyl-10-methoxy-2,3,4,5,6,7-hexahydro-1,6-methano-1h-4-benzazonine-7(6h)-one; (1r,9r)-4-methoxy-1,11-dimethyl-11-azatricyclo[7.4.1.0(2,7)]tetradeca-2,4,6-trien-8-one (viii)
1,4-dimethyl-10-methoxy-2,3,4,5,6,7-hexahydro-1,6-methano-1h-4-benzazonine-7-ol; (1r,9r)-4-methoxy-1,11-dimethyl-11-azatricyclo[7.4.1.0(2,7)]tetradeca-2,4,6-trien-8-ol (ix)
1-[[(4-hydroxy-6-methyl-3-pyridinyl)carbonyl]oxy]-2,5-pyrrolidinedione (x)
Reference 1:
    pop, e.; et al.; synthesis of deuterated dexanabinol, a nonpsychotropic cannabinoid with neuroprotective properties. j label compd radiopharm 1998, 41, 10, 885.

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地塞米诺;英文名Dexanabinone;Dexanabinol;PRS-211007;HU-211;CAS[112924-45-5]

 
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