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澳瑞他系列衍生物及原料
澳瑞他汀: 抗体药物偶联物(antibody-drug conjugate, ADC)是一类用于治疗癌症的新兴靶向疗法, 旨在将小分子化疗直接递送并杀伤肿瘤细胞, 同时保留健康细胞。自2000年MYLOTARG成功获批以来, 抗体药物偶联物(ADC)已成为癌症靶向治疗的关键类别, 它主要包含三部分: 单克隆抗体、连接子和毒素。单克隆抗体是决定ADC疗效的关键; 连接子决定着ADC药物系统毒性及临床疗效; 毒素是决定ADC药物杀伤力大小的关键因素。尽管目前公布的ADC药物中所用毒素种类超过130余种, 但处于临床试验或已上市的ADC药物所用毒素只有6-8个。按作用方式可大致分为三类: 微管蛋白抑制剂、DNA合成抑制剂和拓扑异构酶抑制剂。其中以微管蛋白抑制剂中的MMAE作为毒素分子的ADC药物获批最多。以下是该产品中间体及原材料及工艺构架:
| 化合物名称 | CAS号 | 英文名称/描述 |
|---|---|---|
| KSM-1 | 2019182-02-4 | 2-Pyrrolidinepropanamide, N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]-β-methoxy-α-methyl-, hydrochloride (1:1), (αR,βR,2S) |
| KSM-2 | 863971-44-2 | L-Valinamide, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-[(1S,2S)-1-[(1R)-2-carboxy-1-methoxyethyl]-2-methylbutyl]-N-methyl |
| Intermediate | 177423-00-6 | Heptanoic acid, 4-[[(2S)-2-amino-3-methyl-1-oxobutyl]methylamino]-3-methoxy-5-methyl-, 1,1-dimethylethyl ester, (3R,4S,5S) |
| Intermediate | 84000-11-3 | N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine |
| Intermediate | 120205-50-7 | 2-Pyrrolidinepropanoic acid, 1-[(1,1-dimethylethoxy)carbonyl]-β-methoxy-α-methyl-, (αR,βR,2S) |
| Intermediate | 37577-28-9 | Benzenemethanol, α-[(1R)-1-aminoethyl]-, (αS) |
| Vedotin | 646502-53-6 | Vedotin L-Valinamide, N-[[[4-[[N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-L-ornithyl]amino]phenyl]methoxy]carbonyl]-N-methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl |
| KSM-1 | 159857-81-5 | L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[[[(4-nitrophenoxy)carbonyl]oxy]methyl]phenyl] |
| KSM-2 / MMAE (Mono methyl Auristatin E) | 474645-27-7 | L-Valinamide, N-methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl |
| Intermediate | 159857-80-4 | L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl] |
| Intermediate | 5070-13-3 | Carbonic acid, bis(4-nitrophenyl) ester |
| Intermediate | 2088364-35-4 | Not yet assigned |
| Intermediate | 55750-63-5 | 1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, 2,5-dioxo-1-pyrrolidinyl ester |
| Intermediate | 159858-21-6 | L-Ornithine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-N5-(aminocarbonyl) |
| Intermediate | 623-04-1 | Benzenemethanol, 4-amino |
| Intermediate | 130878-68-1 | L-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2,5-dioxo-1-pyrrolidinyl ester |
| Intermediate | 372-75-8 | Citrulline: L-Ornithine, N5-(aminocarbonyl) |
📚 参考文献
1. Wang Z, Li H, Gou L, Li W, Wang Y. Antibody-drug conjugates: Recent advances in payloads. Acta Pharm Sin B. 2023 Oct;13(10):4025-4059.
2. Dosio, F.; Brusa, P.; Cattel, L. Immunotoxins and Anticancer Drug Conjugate Assemblies: The Role of the Linkage between Components. Toxins 2011, 3, 848-883.
3. Graham P Collins, David Bruce, Toby A Eyre. New Therapies in T-cell Lymphoma [J]. Lymphoma and Chronic Lymphocytic Leukemias. 2014, 1(4):1-8.
4. Kovtun YV, Audette CA, Ye Y, Xie H, Ruberti MF, Phinney SJ, Leece BA, Chittenden T, Blättler WA, Goldmacher VS. Antibody-drug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen. Cancer Res. 2006 Mar 15;66(6):3214-21.
5. O'Connor O.A., Lue J.K., Sawas A., Amengual J.E., Deng C.C., Kalac M., Falchi L., Marchi E., Turenne I., Lichtenstein R., et al. Brentuximab vedotin plus bendamustine in relapsed or refractory Hodgkin's lymphoma: an international, multicentre, single-arm, phase 1-2 trial. Lancet Oncol. 2018;19:257–266.
1. Wang Z, Li H, Gou L, Li W, Wang Y. Antibody-drug conjugates: Recent advances in payloads. Acta Pharm Sin B. 2023 Oct;13(10):4025-4059.
2. Dosio, F.; Brusa, P.; Cattel, L. Immunotoxins and Anticancer Drug Conjugate Assemblies: The Role of the Linkage between Components. Toxins 2011, 3, 848-883.
3. Graham P Collins, David Bruce, Toby A Eyre. New Therapies in T-cell Lymphoma [J]. Lymphoma and Chronic Lymphocytic Leukemias. 2014, 1(4):1-8.
4. Kovtun YV, Audette CA, Ye Y, Xie H, Ruberti MF, Phinney SJ, Leece BA, Chittenden T, Blättler WA, Goldmacher VS. Antibody-drug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen. Cancer Res. 2006 Mar 15;66(6):3214-21.
5. O'Connor O.A., Lue J.K., Sawas A., Amengual J.E., Deng C.C., Kalac M., Falchi L., Marchi E., Turenne I., Lichtenstein R., et al. Brentuximab vedotin plus bendamustine in relapsed or refractory Hodgkin's lymphoma: an international, multicentre, single-arm, phase 1-2 trial. Lancet Oncol. 2018;19:257–266.
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