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药物详细合成路线

Name Mometasone furoate;S-2640;Sch-32088;Asmanex Twisthaler;Asmanex;Nasonex;Altosone;Fulmeta;Ecotone;Ecural;Elocon
Chemical Name 9,21-Dichloro-11beta,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 17-furoate
CAS 83919-23-7
Related CAS
Formula C27H30Cl2O6
Structure
Formula Weight 521.44255
Stage 上市-1987
Company Essex (Originator), Schering-Plough (Originator), Shionogi (Licensee)
Activity/Mechanism Antipsoriatics, Asthma Therapy, Atopic Dermatitis, Agents for, DERMATOLOGIC DRUGS, Drugs for Allergic Rhinitis, RESPIRATORY DRUGS, Treatment of Upper Respiratory Tract Disorders, Antiinflammatory Drugs, Corticosteroids
Syn. Route 3
Route 1
by esterification of mometasone (i) with 2-furoyl chloride (ii) by means of tea in dichloromethane.
List of intermediates No.
methyl (3r,6s,9r,9ar)-6-[(methoxycarbonyl)amino]-9-methyl-5-oxooctahydro[1,3]thiazolo[3,2-a]azepine-3-carboxylate (ii)
5-bromo-1,3-thiazol-2-ylamine; 5-bromo-1,3-thiazol-2-amine (i)
Reference 1:
    heggie, w.; bandarra, j. (hovione sociedade quimica sa); process for the preparation of mometasone furoate. ep 1074558; jp 2001048897 .

Route 2
the reaction of 9beta,11beta-epoxy-17alpha,21-dihydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione (i) with mscl in pyridine gives the corresponding 21-mesylate (ii), which is treated with licl in the same solvent to yield 21-chloro-9beta,11beta-epoxy-17alpha-hydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione (iii). the esterification of (iii) with 2-furoyl chloride (iv) and tea affords the expected ester (iv), which is finally treated with anhydrous hcl in acetic acid in order to open the epoxide ring to provide the target mometasone furoate. a similar reaction sequence can be performed using p-toluenesulfonyl chloride instead of mesyl chloride in the first step of the sequence.
List of intermediates No.
methyl (3r,6s,9r,9ar)-6-[(methoxycarbonyl)amino]-9-methyl-5-oxooctahydro[1,3]thiazolo[3,2-a]azepine-3-carboxylate (iv)
5-({[5-(tert-butyl)-1,3-oxazol-2-yl]methyl}sulfanyl)-1,3-thiazol-2-amine; 5-({[5-(tert-butyl)-1,3-oxazol-2-yl]methyl}sulfanyl)-1,3-thiazol-2-ylamine (i)
2-[4-(bromomethyl)phenyl]acetic acid; 4-(bromomethyl)phenyl acetic acid; 4-carboxymethylbenzyl bromide (ii)
2-[4-(bromomethyl)phenyl]-n-[5-({[5-(tert-butyl)-1,3-oxazol-2-yl]methyl}sulfanyl)-1,3-thiazol-2-yl]acetamide (iii)
5h-dibenzo[a,d]cycloheptene (v)
Reference 1:
    shapiro, e.l. (schering corp.); 3,20-dioxo-1,4-pregnanediene-17alpha-ol 17-aromatic heterocycle carboxylates. ep 0057401; us 4472393 .
Reference 2:
    tann, c.-h.; tsai, d.j.s.; kwok, d.-i.; fu, x. (schering corp.); process for the preparation of 17-esters of 9alpha,21-dihalo-pregnane-11beta,17alpha-diol-20-ones. wo 9800437 .

Route 3
the esterification of 21-chloro-17alpha-hydroxy-16alpha-methyl-1,4,9(11)-pregnatriene-3,20-dione (i) with 2-furoyl chloride (ii) by means of tea gives the corresponding ester (iii), which is then treated with hclo4 and 1,3-dichloro-5,5-dimethylhydantoin (ddh) in thf/water in order to add cl-oh to the 9(11)-double bond of ester (iii).
List of intermediates No.
methyl (3r,6s,9r,9ar)-6-[(methoxycarbonyl)amino]-9-methyl-5-oxooctahydro[1,3]thiazolo[3,2-a]azepine-3-carboxylate (ii)
6,10b-dihydro-1ah-dibenzo[3,4:6,7]cyclohepta[1,2-b]oxirene (i)
(10s,11r)-11-allyl-10,11-dihydro-5h-dibenzo[a,d]cyclohepten-10-ol (iii)
Reference 1:
    shapiro, e.l. (schering corp.); 3,20-dioxo-1,4-pregnanediene-17alpha-ol 17-aromatic heterocycle carboxylates. ep 0057401; us 4472393 .

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糠酸莫美他松;英文名Mometasone furoate;S-2640;Sch-32088;Asmanex Twisthaler;Asmanex;Nasonex;Altosone;Fulmeta;Ecotone;Ecural;Elocon;CAS[83919-23-7]

 
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