Clomifen

Clomifene Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Clomid,Lepetit,Italy,1966

• Verwenden

  Clomifene is used for infertility in order to increase reproductive properties of oligoovulatory women who have three or four ovulatory cycles per year, leading to normal monthly ovulation.

• Verwenden

  Antiestrogen.

• Indications

  Clomifene acts by enhancing follicular growth caused by ovulation. The primary indication for using clomifene is induction of ovulation in non-ovulating women who still have some estrogen production.

• Definition

  ChEBI: Zuclomifene is a stilbenoid.

• Manufacturing Process

  A mixture of 20 g of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol in 200 cc of ethanol containing an excess of hydrogen chloride was refluxed 3 hours. The solvent and excess hydrogen chloride were removed under vacuum, and the residue was dissolved in a mixture of ethyl acetate and methylene chloride. 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethylene hydrochloride was obtained, melting at 148° to 157°C. This hydrochloride salt was treated with N-chlorosuccinimide in dry chloroform under reflux. The product then obtained was converted to the free base and treated with citric acid. The dihydrogen citrate salt of 1-[p-(β-diethylaminoethoxy)phenyl]-1,2- diphenylchloroethylene was obtained, melting at 116.5° to 118°C.
  The intermediate 1-[p-(β-diethylaminoethoxy)phenyl]-1,2-diphenylethanol was obtained by treating 4-(β-diethylaminoethoxy)benzophenone with benzylmagnesium chloride. It melted at 95° to 96°C.

• Trademarks

  Clomid (Sanofi Aventis); Serophene (Serono).

• Therapeutic Function

  Antiestrogen

• Synthese

  Clomifene, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine (28.2.4), is synthesized from 4-hydroxybenzophenone by reacting it with 2-diethylaminoethylchloride in the presence of an alkali, which gives 4-(2-diethylaminoethoxy)benzophenone (28.2.1). This is reacted with benzylmagnesium chloride in a Grignard reaction, forming as a result the corresponding carbinol (28.2.2). Dehydrating this with hydrogen chloride gives 2-[p-(1,2-diphenylvinyl) phenoxy]triethylamine (28.2.4), the vinylic hydrogen atom of which is replaced with a chlorine atom using N-chlorosuccinimide, giving clomifene (28.2.4) .

  

Clomifene Upstream-Materialien And Downstream Produkte

Clomifen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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