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【结 构 式】 
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【药物名称】Lotrifen, L-12717, DL-717IT, Privaprol, Canocenta 【化学名称】2-(4-Chlorophenyl)[1,2,4]triazolo[5,1-a]isoquinoline 【CA登记号】66535-86-2 【 分 子 式 】C16H10ClN3 【 分 子 量 】279.7312 |
【开发单位】Altana Pharma (Originator), Lepetit (Originator) 【药理作用】Contraceptives, Disorders of Sexual Function and Reproduction, Treatment of, ENDOCRINE DRUGS |
合成路线1
The cyclization of 2-amino-3,4-dihydro-1(2H)-isoquinolinone (I) with ethyl 4-chlorobenzimidate (II) by heating at 125 C under vacuum gives 2-(4-chloro-phenyl)-5,6-dihydro-s-triazolo[5,1-a]isoquinoline (III), which is dehydrogenated by means of N-bromoacetamide in refluxing CCl4.
| 【1】 Consonni, P.; Lerner, L.; Omodei-Salé, A. (Lepetit SpA); 2-Substd. phenyl-5-triazols[5,1-a]isoquinoline cpds. US 4075341 . |
| 【2】 de Angelis, L.; Castaner, J.; Lotrifen. Drugs Fut 1985, 10, 10, 817. |
合成路线2
By cyclization of isoquinolinone (IV) with 4-chlorobenzonitrile (VI) by means of sodium ethoxide in refluxing ethanol.
| 【1】 Omodei-Sale, A.; Favara, D. (Lepetit SpA); Triazolo[5,1-a]isoquinoline deriv. DE 2942195; FR 2440369 . |
| 【2】 de Angelis, L.; Castaner, J.; Lotrifen. Drugs Fut 1985, 10, 10, 817. |
合成路线3
The condensation of 2-amino-1(2H)-isoquinolinone (IV) with imidate (II) by heating at 125 C as before gives 2-(4-cholorobenzimidoylamino)-1(2H)-isoquinolinone (V), which is cyclized by means of NaH in ethoxyethanol.
| 【1】 Omodai-Sale, A.; Consonni, P.; Lerner, L. (Lepetit SpA); S-triazolo[5,1-a]isochinolin derivate. DE 2707272; NL 7704940 . |
| 【2】 de Angelis, L.; Castaner, J.; Lotrifen. Drugs Fut 1985, 10, 10, 817. |