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              藥物詳細合成路線

              Name CHF-4227
              Chemical Name 3-(4-Methoxyphenyl)-4-[4-[2-(1-piperidinyl)ethoxy]benzyl]-2H-1-benzopyran-7-ol hydrochloride
              CAS 3764-87-2
              Related CAS
              Formula C30H34ClNO4
              Structure
              Formula Weight 508.06278
              Stage I 期臨床
              Company Chiesi (Originator)
              Activity/Mechanism Bone Diseases, Treatment of, ENDOCRINE DRUGS, Gynecological Disorders, Treatment of , METABOLIC DRUGS, Prevention of Osteoporosis, Treatment of Postmenopausal Syndrome , Selective Estrogen Receptor Modulators (SERM)
              Syn. Route 1
              Route 1
              the title compound is synthesized starting from the natural isoflavone formononetin (i). esterification of (i) with pivaloyl chloride (ii) affords pivalate (iii). catalytic hydrogenation of (iii) in the presence of pd/baso4 leads to the chromane derivative (iv). the grignard reagent (vi), prepared from 4-(benzyloxy)benzyl chloride (v), is then condensed with ketone (iv) to furnish the tertiary alcohol (vii). the o-benzyl protecting group of (vii) is then removed by catalytic hydrogenolysis to afford phenol (viii). alkylation of (viii) with n-(2-chloroethyl)piperidine (ix) and k2co3, with simultaneous pivalate ester hydrolysis, leads to the piperidylethyl ether (x). the tertiary alcohol of (x) is finally dehydrated by means of hcl in acetonitrile to provide the target compound (1,2).
              List of intermediates No.
              methyl (2r,3s)-3-[(acetoxy)methyl]-2-oxiranecarboxylate (ix)
              3-sulfanyl-1-propanol (ii)
              Reference 1:
                  ghirardi, s.; armani, e.; amari, g.; delcanale, m.; civelli, m.; caruso, p.; galbiati, e.; synthesis and pharmacological activity of chf 4227, one of the most potent in vitro and in vivo serms till new discovered. drugs fut 2002, 27, suppl. a.
              Reference 2:
                  delcanale, m.; civelli, m.; armani, e.; amari, g.; galbiati, e. (chiesi farmaceutici spa); 2h-1-benzopyran derivs., processes for their preparation and pharmaceutical compsns. thereof. ep 1229036; ep 1281710; ep 1355906; wo 0259113 .

              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曲托龍;英文名CHF-4227;CAS[3764-87-2]

               
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