WO2017125093A1 - 对苯二酚类化合物及其制备方法与在抗肿瘤或免疫调节中的应用 - Google Patents
对苯二酚类化合物及其制备方法与在抗肿瘤或免疫调节中的应用 Download PDFInfo
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- WO2017125093A1 WO2017125093A1 PCT/CN2017/074386 CN2017074386W WO2017125093A1 WO 2017125093 A1 WO2017125093 A1 WO 2017125093A1 CN 2017074386 W CN2017074386 W CN 2017074386W WO 2017125093 A1 WO2017125093 A1 WO 2017125093A1
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- 0 CC(C)(C)c(cc(cc1)OC)c1O** Chemical compound CC(C)(C)c(cc(cc1)OC)c1O** 0.000 description 1
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
Description
Claims (9)
- 根据权利要求1所述的化合物、盐、水合物或溶剂合物,其特征在于:R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖。
- 根据权利要求1或2所述的化合物、盐、水合物或溶剂合物,其特征在于:式Ⅰ中,X和Y的选择如下述1)-3)中任一种:1)当X为C=O时,Y为NH;2)当X为CH2时,Y为O;3)X为C=O或CH2,Y不存在。
- 根据权利要求3所述的化合物、盐、水合物或溶剂合物,其特征在于:式Ⅰ所示化合物包括但不限于下述1)-66)化合物中任一种:1)(N-苄基)氨基甲酸-(2-叔丁基-4-甲氧基苯酚)酯,2)(N-正丁基)氨基甲酸(2-叔丁基-4-甲氧基苯酚)酯,3)(N-异丙基)氨基甲酸(2-叔丁基-4-甲氧基苯酚)酯,4)(N-环己基)氨基甲酸(2-叔丁基-4-甲氧基苯酚)酯,5)(N-苯乙基)氨基甲酸(2-叔丁基-4-甲氧基苯酚)酯,6)特戊酰(2-叔丁基-4-甲氧基苯酚氧基)甲基酯,7)苯甲酸-2-叔丁基-4-甲氧基苯酚酯,8)乙酸-2-叔丁基-4-甲氧基苯酚酯,9)烟酸-2-叔丁基-4-甲氧基苯酚酯,10)异烟酸-2-叔丁基-4-甲氧基苯酚酯,11)环己烯甲酸-2-叔丁基-4-甲氧基苯酚酯,12)丙酸-2-叔丁基-4-甲氧基苯酚酯,13)丙烯酸-2-叔丁基-4-甲氧基苯酚酯,14)3,4-二甲氧基苯乙酸(2-叔丁基-4-甲氧基苯酚)-酯,15)丁炔酸-2-叔丁基-4-甲氧基苯酚酯,16)2,2‘-联苯二甲酸双(2-叔丁基-4-甲氧基苯酚)酯,17)2-氯-5-三氟甲基苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,18)3-氟苯乙酸(2-叔丁基-4-甲氧基苯酚)酯,19)(1H-吲哚-3基)乙酸(2-叔丁基-4-甲氧基苯酚)酯,20)3-(4-氟苯基)-丙酸-(2-叔丁基-4-甲氧基苯酚)酯,21)N-叔定氧羰基哌啶-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,22)对苯二甲酸二(2-叔丁基-4-甲氧基苯酚)酯,23)3-(3-硝基苯基)丙酸(2-叔丁基-4-甲氧基苯酚)酯,24)4-苯基苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,25)4-甲基吡啶-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,26)4-甲氧基吡啶-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,27)十六酸-2-叔丁基-4-甲氧基苯酚酯,28)N-叔丁氧羰基甘氨酸(2-叔丁基-4-甲氧基苯酚)酯,29)3-氟-4-氯苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,30)N-叔丁氧羰基四氢吡咯、苯并杂环-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,31)3-氰基苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,32)N-叔丁氧羰基丙氨酸(2-叔丁基-4-甲氧基苯酚)酯,33)2-萘甲酸(2-叔丁基-4-甲氧基苯酚)酯,34)丙二酸二(2-叔丁基-4-甲氧基苯酚)酯,35)3,6-二氯哒嗪-4-甲酸(2-叔丁基-4-甲氧基苯酚)酯,36)1-甲基环丙甲酸(2-叔丁基-4-甲氧基苯酚)酯,37)2-吲哚甲酸(2-叔丁基-4-甲氧基苯酚)酯,38)2-氯-3-吡啶甲酸(2-叔丁基-4-甲氧基苯酚)酯,39)2-噻吩乙酸(2-叔丁基-4-甲氧基苯酚)酯,40)3-(4-甲基苯基)-丙酸(2-叔丁基-4-甲氧基苯酚)酯,41)丙炔酸(2-叔丁基-4-甲氧基苯酚)酯,42)2-苯基丙酸(2-叔丁基-4-甲氧基苯酚)酯,43)2-氟丙酸(2-叔丁基-4-甲氧基苯酚)酯,44)环己乙酸(2-叔丁基-4-甲氧基苯酚)酯,45)环戊甲酸(2-叔丁基-4-甲氧基苯酚)酯,46)金刚烷乙酸(2-叔丁基-4-甲氧基苯酚)酯,47)环丙基乙酸(2-叔丁基-4-甲氧基苯酚)酯,48)N-叔丁氧羰基哌啶-4-甲酸(2-叔丁基-4-甲氧基苯酚)酯,49)辛酸(2-叔丁基-4-甲氧基苯酚)酯,50)7-氧代辛酸(2-叔丁基-4-甲氧基苯酚)酯,51)环己-2-烯甲酸(2-叔丁基-4-甲氧基苯酚)酯,52)2,4,5-三氟苯乙酸(2-叔丁基-4-甲氧基苯酚)酯,53)2-溴-5-碘苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,54)2-氟-4-硝基苯甲酸(2-叔丁基-4-甲氧基苯酚)酯,55)N-叔丁氧羰基哌啶-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,56)对苯二乙酸二(2-叔丁基-4-甲氧基苯酚)酯,57)4-苯甲酰丁酸(2-叔丁基-4-甲氧基苯酚)酯,58)3,5-二甲氧基苯并烯酸(2-叔丁基-4-甲氧基苯酚)酯,59)4-氯吡啶-2-甲酸(2-叔丁基-4-甲氧基苯酚)酯,60)N-甲基哌啶-3-甲酸(2-叔丁基-4-甲氧基苯酚)酯,61)N-叔丁氧羰基-6-氨基戊酸(2-叔丁基-4-甲氧基苯酚)酯,62)3,3,3-三氟丙酸(2-叔丁基-4-甲氧基苯酚)酯,63)吗啉-4-基乙酸(2-叔丁基-4-甲氧基苯酚)酯,64)3-(3,5-二叔丁基-4-羟基-苯基)丙酸-(2-叔丁基-4-甲氧基苯酚)酯,65)己二酸二(2-叔丁基-4-甲氧基苯酚)酯;66)2-(2-叔丁基-4-甲氧基苯氧基)乙酸乙酯。
- 式Ⅰ所示化合物的制备方法,包括如下(1)、(2)、(3)或(4)的步骤:(1)当X为C=O时,Y为NH时,包括如下步骤:RCH2与三光气进行反应得到R-N=C=O;R-N=C=O与2-叔丁基-4-甲氧基苯酚经缩合反应即得式Ⅰ所示化合物;式Ⅰ、RCH2和R-N=C=O中,R选自下述基团中任一种:至少1个碳原子的取代或未取代的烷基、至少3个碳原子的取代或未取代的环烷基、至少2个碳原子的取代或未取代的烯基或炔基和取代或未取代的芳基或杂芳基,R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖;式Ⅰ中,X为C=O,Y为NH;(2)当X为CH2时,Y为O时,包括如下步骤:2-叔丁基-4-甲氧基苯酚钠与式1所示化合物经缩合反应即得式Ⅰ所示化合物;式Ⅰ和式1中,R选自下述基团中任一种:至少1个碳原子的取代或未取代的烷基、至少3个碳原子的取代或未取代的环烷基、至少2个碳原子的取代或未 取代的烯基或炔基和取代或未取代的芳基或杂芳基;R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖;式Ⅰ中,X为CH2,Y为O;(3)X为C=O,Y不存在时,即为式Ⅱ所示化合物,包括如下1)或2)的步骤:1)2-叔丁基-4-甲氧基苯酚钠与式2所示酰氯经缩合即得式Ⅱ所示化合物;式Ⅱ和式2中,R选自下述基团中任一种:至少1个碳原子的取代或未取代的烷基、至少3个碳原子的取代或未取代的环烷基、至少2个碳原子的取代或未取代的烯基或炔基和取代或未取代的芳基或杂芳基;R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖;式Ⅱ中,X为C=O;2)2-叔丁基-4-甲氧基苯酚钠与式3所示羧酸经缩合即得式Ⅱ所示化合物;式Ⅱ和式3中,R选自下述基团中任一种:至少1个碳原子的取代或未取代的烷基、至少3个碳原子的取代或未取代的环烷基、至少2个碳原子的取代或未取代的烯基或炔基和取代或未取代的芳基或杂芳基;R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖;式Ⅱ中,X为C=O;(4)当X为CH2,Y不存在时,即为式Ⅱ所示化合物,包括如下步骤:2-叔丁基-4-甲氧基苯酚钠与式4所示化合物经缩合反应即得式Ⅱ所示化合物;式Ⅱ和式4中,R选自下述基团中任一种:至少1个碳原子的取代或未取代 的烷基、至少3个碳原子的取代或未取代的环烷基、至少2个碳原子的取代或未取代的烯基或炔基和取代或未取代的芳基或杂芳基;R中取代基为卤素、氨基、硝基、酯基、羰基、氨基酸衍生物、天然黄酮、天然生物碱、聚乙二醇、多聚谷氨酸或多糖;X为CH2。
- 式Ⅰ所示化合物、其药学上可接受的盐、其水合物或其溶剂合物在制备抗肿瘤或免疫调节的药物中的应用。
- 根据权利要求6所述的应用,其特征在于:式Ⅰ所示化合物释放2-叔丁基-4-甲氧基苯酚。
- 式Ⅰ所示化合物、其药学上可接受的盐、其水合物或其溶剂合物在制备释放2-叔丁基-4-甲氧基苯酚的前药中的应用。
- 一种抗肿瘤药物或免疫调节药物,其活性成分为式Ⅰ所示化合物、其药学上可接受的盐、其水合物、其溶剂合物或者药物组合物。
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US11738000B2 (en) | 2023-08-29 |
AU2017209362A1 (en) | 2018-02-22 |
AU2017209362B2 (en) | 2021-01-28 |
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