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【结 构 式】 
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【药物名称】HKI-9924154 【化学名称】(2S,5R,6R)-6-[2(R)-[2-[N-(2,3-Diacetoxybenzoyl)-N-[4-(2,3-diacetoxybenzamido)butyl]amino]acetamido]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 【CA登记号】 【 分 子 式 】C44H47N5O15S 【 分 子 量 】917.95369 |
【开发单位】Grünenthal (Originator), Hans Knöll Institute Natural Prod. Res. (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Metal Chelators, Penicillins |
合成路线1
Reductive condensation of 1,4-butanediamine (I) with glyoxylic acid (II) affords 3,8-diazaoctanoic acid (III). Subsequent acylation of diamino acid (III) with 2,3-diacetoxybenzoyl chloride (IV) provides diamide (V). After activation of (V) as the corresponding mixed anhydride with either methyl or isobutyl chloroformate, condensation with ampicillin (VI) yields the title compound.
| 【1】 RF-2691A. Drug Data Rep 1995, 17, 9, 867. |
| 【2】 Berg, A.; Heinisch, L.; Mollmann, U.; Wittmann, S.; Scherlitz-Hofmann, I.; Stoiber, T. (Grunenthal GmbH); Catecholate beta-lactam conjugates, method for producing the same and the use thereof. DE 10111160; WO 0270016 . |
| 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) | 42070 | 1,4-butanediamine; 4-aminobutylamine | 110-60-1 | C4H12N2 | 详情 | 详情 |
| (II) | 15618 | 2-Oxoacetic acid; Glyoxylic Acid | 298-12-4 | C2H2O3 | 详情 | 详情 |
| (III) | 58505 | 2-[(4-aminobutyl)amino]acetic acid | C6H14N2O2 | 详情 | 详情 | |
| (IV) | 58506 | 2-(acetyloxy)-3-(chlorocarbonyl)phenyl acetate | C11H9ClO5 | 详情 | 详情 | |
| (V) | 58507 | 2-[[2,3-bis(acetyloxy)benzoyl](4-{[2,3-bis(acetyloxy)benzoyl]amino}butyl)amino]acetic acid | C28H30N2O12 | 详情 | 详情 | |
| (VI) | 31107 | (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylethanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | 69-53-4 | C16H19N3O4S | 详情 | 详情 |