【结 构 式】 |
【药物名称】Ipamorelin, NSAC, NNC-26-0161 【化学名称】2-Methyl-alanyl-L-histidyl-3-(2-naphthyl)-D-alanyl-D-phenyalanyl-L-lysinamide 【CA登记号】170851-70-4 【 分 子 式 】C38H49N9O5 【 分 子 量 】711.87153 |
【开发单位】Novo Nordisk (Originator) 【药理作用】ENDOCRINE DRUGS, Pituitary Disorder Therapy, Treatment of Growth Hormone Deficiency, Treatment of Growth Hormone Secretion Disorders |
合成路线1
The successive condensations of fluorenylmethoxycarbonyl-Rink amide resin (I) with Nalpha-FMOC-Nepsilon-Boc-L-lysine (II), FMOC-D-phenylalanine (IV), FMOC-D-2-naphthylalanine (VI), FMOC-Npi-trityl-L-histidine (VIII), and finally 2-(tert-butoxycarbonylamino)isobutyric acid (X), using the solid phase peptide technique synthesis yielded resins (III), (V), (VII), (IX) and finally (XI). This last resin was then treated with trifluoroacetic acid in order to eliminate the Boc protecting groups and the solid phase resin and isolate the target compound.
【1】 Muller, L.; et al.; C-14-labelling of ipamorelin, a growth hormone secretagogue. J Label Compd Radiopharm 1998, 41, 12, 1093. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 18854 | (2S)-6-[(tert-butoxycarbonyl)amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid | C26H32N2O6 | 详情 | 详情 | |
(II) | 28722 | 9H-fluoren-9-ylmethyl carbamate | 84418-43-9 | C15H13NO2 | 详情 | 详情 |
(III) | 28723 | 9H-fluoren-9-ylmethyl (1S)-1-(aminocarbonyl)-5-[(tert-butoxycarbonyl)amino]pentylcarbamate | C26H33N3O5 | 详情 | 详情 | |
(IV) | 28730 | (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropionic acid | C24H21NO4 | 详情 | 详情 | |
(V) | 28724 | 9H-fluoren-9-ylmethyl (1R)-2-([(1S)-1-(aminocarbonyl)-5-[(tert-butoxycarbonyl)amino]pentyl]amino)-1-benzyl-2-oxoethylcarbamate | C35H42N4O6 | 详情 | 详情 | |
(VI) | 28725 | (2R)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(2-naphthyl)propionic acid | C28H23NO4 | 详情 | 详情 | |
(VII) | 28726 | 9H-fluoren-9-ylmethyl (1R,4R,7S)-7-(aminocarbonyl)-4-benzyl-15,15-dimethyl-1-(2-naphthylmethyl)-2,5,13-trioxo-14-oxa-3,6,12-triazahexadec-1-ylcarbamate | C48H53N5O7 | 详情 | 详情 | |
(VIII) | 28727 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-(1-trityl-1H-imidazol-5-yl)propionic acid | C40H33N3O4 | 详情 | 详情 | |
(IX) | 28728 | 9H-fluoren-9-ylmethyl (1S,4R,7R,10S)-10-(aminocarbonyl)-7-benzyl-18,18-dimethyl-4-(2-naphthylmethyl)-2,5,8,16-tetraoxo-1-[(1-trityl-1H-imidazol-5-yl)methyl]-17-oxa-3,6,9,15-tetraazanonadec-1-ylcarbamate | C73H74N8O8 | 详情 | 详情 | |
(X) | 18471 | N-(tert-butoxycarbonyl)-2-methylalanine | 30992-29-1 | C9H17NO4 | 详情 | 详情 |
(XI) | 28729 | tert-butyl (4S,7R,10R,13S)-13-(aminocarbonyl)-10-benzyl-1,1,21,21-tetramethyl-7-(2-naphthylmethyl)-2,5,8,11,19-pentaoxo-4-[(1-trityl-1H-imidazol-5-yl)methyl]-20-oxa-3,6,9,12,18-pentaazadocos-1-ylcarbamate | C67H79N9O9 | 详情 | 详情 |