CN103635475B - 5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 - Google Patents
5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 Download PDFInfo
- Publication number
- CN103635475B CN103635475B CN201280027456.6A CN201280027456A CN103635475B CN 103635475 B CN103635475 B CN 103635475B CN 201280027456 A CN201280027456 A CN 201280027456A CN 103635475 B CN103635475 B CN 103635475B
- Authority
- CN
- China
- Prior art keywords
- group
- tetrandrine
- nitrogen
- heteroaryl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 CN(CCc1c2)C(Cc(cc3Oc4ccc(C[C@@]5N(C)CCc6c5c(O5)c(*)c(OC)c6OC)cc4)ccc3OC)c1cc5c2OC Chemical compound CN(CCc1c2)C(Cc(cc3Oc4ccc(C[C@@]5N(C)CCc6c5c(O5)c(*)c(OC)c6OC)cc4)ccc3OC)c1cc5c2OC 0.000 description 4
- VNBSKOLSTYLJBG-CONSDPRKSA-N CCOc(c(Oc1cc([C@H](Cc(cc2)ccc2Oc2cc(C[C@@H]3N(C)CC4)ccc2OC)N(C)CC2)c2cc1OC)c3c4c1)c1OC Chemical compound CCOc(c(Oc1cc([C@H](Cc(cc2)ccc2Oc2cc(C[C@@H]3N(C)CC4)ccc2OC)N(C)CC2)c2cc1OC)c3c4c1)c1OC VNBSKOLSTYLJBG-CONSDPRKSA-N 0.000 description 1
- TWZLRAUWJDELTD-AIJWEMPKSA-N CC[C@](Cc(cc1Oc2ccc(C[C@@H]3N(C)CCc(cc4OC)c33)cc2)ccc1O)(c1c2)N(C)CCc1cc1c2Oc3c4O1 Chemical compound CC[C@](Cc(cc1Oc2ccc(C[C@@H]3N(C)CCc(cc4OC)c33)cc2)ccc1O)(c1c2)N(C)CCc1cc1c2Oc3c4O1 TWZLRAUWJDELTD-AIJWEMPKSA-N 0.000 description 1
- BDRAVEKLUCOCTG-CONSDPRKSA-N CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2c(CCl)c(OC)c3OC)cc2)c2OC)c5c1cc4OC Chemical compound CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2c(CCl)c(OC)c3OC)cc2)c2OC)c5c1cc4OC BDRAVEKLUCOCTG-CONSDPRKSA-N 0.000 description 1
- ASKPHAFUGZXWNY-ZPGRZCPFSA-N CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2c(COCC[n]2cncc2)c(OC)c3OC)cc2)c2OC)c5c1cc4OC Chemical compound CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2c(COCC[n]2cncc2)c(OC)c3OC)cc2)c2OC)c5c1cc4OC ASKPHAFUGZXWNY-ZPGRZCPFSA-N 0.000 description 1
- WVTKBKWTSCPRNU-KYJUHHDHSA-N CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2cc(OC)c3OC)cc2)c2OC)c5c1cc4OC Chemical compound CN(CC1)[C@@H](Cc(cc2)ccc2Oc(cc(C[C@@H](c2c3Oc4c5)N(C)CCc2cc(OC)c3OC)cc2)c2OC)c5c1cc4OC WVTKBKWTSCPRNU-KYJUHHDHSA-N 0.000 description 1
- ANJMFZGRGHQXMA-VMPREFPWSA-N CN(CC1)[C@@H](Cc(cc2)ccc2Oc2cc(C[C@@H](c3c(c(OC)c4OC)Oc5c6)N(C)CCc3c4Br)ccc2OC)c6c1cc5OC Chemical compound CN(CC1)[C@@H](Cc(cc2)ccc2Oc2cc(C[C@@H](c3c(c(OC)c4OC)Oc5c6)N(C)CCc3c4Br)ccc2OC)c6c1cc5OC ANJMFZGRGHQXMA-VMPREFPWSA-N 0.000 description 1
- FUZMQNZACIFDBL-KYJUHHDHSA-N CN(CC1)[C@@H](Cc(cc2)ccc2Oc2cc(C[C@@H]3N(C)CCc(c(OC)c4OC)c3c(Oc3c5)c4OC)ccc2OC)c5c1cc3OC Chemical compound CN(CC1)[C@@H](Cc(cc2)ccc2Oc2cc(C[C@@H]3N(C)CCc(c(OC)c4OC)c3c(Oc3c5)c4OC)ccc2OC)c5c1cc3OC FUZMQNZACIFDBL-KYJUHHDHSA-N 0.000 description 1
- HGNHIFJNOKGSKI-XLTVJXRZSA-N CN(CC1)[C@@H](Cc(cc2Oc3ccc(CC(c4c5Oc6c7)N(C)CCc4cc(OC)c5OC)cc3)ccc2O)c7c1cc6OC Chemical compound CN(CC1)[C@@H](Cc(cc2Oc3ccc(CC(c4c5Oc6c7)N(C)CCc4cc(OC)c5OC)cc3)ccc2O)c7c1cc6OC HGNHIFJNOKGSKI-XLTVJXRZSA-N 0.000 description 1
- ANOXEUSGZWSCQL-LOYHVIPDSA-N CN(CC1)[C@H](Cc(cc2)ccc2Oc(c([C@@H](Cc(cc2)ccc2Oc2c3OC)N(C)CC4)c4cc4OC)c4OC)c2c1cc3OC Chemical compound CN(CC1)[C@H](Cc(cc2)ccc2Oc(c([C@@H](Cc(cc2)ccc2Oc2c3OC)N(C)CC4)c4cc4OC)c4OC)c2c1cc3OC ANOXEUSGZWSCQL-LOYHVIPDSA-N 0.000 description 1
- PUAVTDKYTXNVBU-PXLJZGITSA-N CN(CCc1c2)[C@@H](Cc(cc3)ccc3Oc(cc(C[C@@H](c3c4O5)N(C)CCc3cc(OC)c4OC)cc3)c3OC(c(cc3)ccc3[N+]([O-])=O)=O)c1cc5c2OC Chemical compound CN(CCc1c2)[C@@H](Cc(cc3)ccc3Oc(cc(C[C@@H](c3c4O5)N(C)CCc3cc(OC)c4OC)cc3)c3OC(c(cc3)ccc3[N+]([O-])=O)=O)c1cc5c2OC PUAVTDKYTXNVBU-PXLJZGITSA-N 0.000 description 1
- GOYCVNCWKXBQBF-SVBPBHIXSA-N CN(CCc1c2)[C@@H](Cc(cc3Oc4ccc(C[C@@H]5N(C)CCc(cc6OC)c55)cc4)ccc3O)c1cc1c2Oc6c5O1 Chemical compound CN(CCc1c2)[C@@H](Cc(cc3Oc4ccc(C[C@@H]5N(C)CCc(cc6OC)c55)cc4)ccc3O)c1cc1c2Oc6c5O1 GOYCVNCWKXBQBF-SVBPBHIXSA-N 0.000 description 1
- HSVFYEXGVUYSRN-WDYNHAJCSA-N CN(CCc1c2)[C@H](Cc(cc3)cc(Oc4cc(C[C@@H](c5c6O7)N(C)CCc5cc5c6OCO5)ccc4)c3OC)c1cc7c2OC Chemical compound CN(CCc1c2)[C@H](Cc(cc3)cc(Oc4cc(C[C@@H](c5c6O7)N(C)CCc5cc5c6OCO5)ccc4)c3OC)c1cc7c2OC HSVFYEXGVUYSRN-WDYNHAJCSA-N 0.000 description 1
- HRVVNEBJOYBLDB-ZPGRZCPFSA-N CN1CCN(Cc(c(CCN(C)[C@H]2Cc(cc3Oc4ccc(C[C@@H]5N(C)CCc(cc6OC)c5cc6O5)cc4)ccc3OC)c2c5c2OC)c2OC)CC1 Chemical compound CN1CCN(Cc(c(CCN(C)[C@H]2Cc(cc3Oc4ccc(C[C@@H]5N(C)CCc(cc6OC)c5cc6O5)cc4)ccc3OC)c2c5c2OC)c2OC)CC1 HRVVNEBJOYBLDB-ZPGRZCPFSA-N 0.000 description 1
- FCTKIMAFGLNYOF-UWXQCODUSA-N Cc(cc1Oc2ccc(C[C@@H](c3c4)N(C)CCc3cc(OC)c4Oc(c([C@H](C#C)N(C)CC3)c3c(COCc3c[s]cc3)c3OC)c3OC)cc2)ccc1OC Chemical compound Cc(cc1Oc2ccc(C[C@@H](c3c4)N(C)CCc3cc(OC)c4Oc(c([C@H](C#C)N(C)CC3)c3c(COCc3c[s]cc3)c3OC)c3OC)cc2)ccc1OC FCTKIMAFGLNYOF-UWXQCODUSA-N 0.000 description 1
- AMSDWLOANMAILF-UHFFFAOYSA-N OCC[n]1cncc1 Chemical compound OCC[n]1cncc1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201280027456.6A CN103635475B (zh) | 2011-08-19 | 2012-08-20 | 5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2011/078622 | 2011-08-19 | ||
| CN2011078622 | 2011-08-19 | ||
| PCT/CN2012/080384 WO2013026383A1 (zh) | 2011-08-19 | 2012-08-20 | 5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 |
| CN201280027456.6A CN103635475B (zh) | 2011-08-19 | 2012-08-20 | 5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103635475A CN103635475A (zh) | 2014-03-12 |
| CN103635475B true CN103635475B (zh) | 2016-06-08 |
Family
ID=47745944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280027456.6A Expired - Fee Related CN103635475B (zh) | 2011-08-19 | 2012-08-20 | 5-位碳取代的汉防己甲素衍生物、及其制备方法和应用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9133207B2 (enExample) |
| EP (1) | EP2767538B1 (enExample) |
| JP (1) | JP5976810B2 (enExample) |
| CN (1) | CN103635475B (enExample) |
| DK (1) | DK2767538T3 (enExample) |
| WO (1) | WO2013026383A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112480140A (zh) * | 2020-12-28 | 2021-03-12 | 杭州医学院 | C5-位取代汉防己甲素衍生物及其制备方法和应用 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016023404A1 (zh) * | 2014-08-15 | 2016-02-18 | 贵州省中国科学院天然产物化学重点实验室 | 双苄基异喹啉衍生物、其制备方法及其在肝病的治疗与预防中的用途 |
| CN107033157B (zh) * | 2016-02-03 | 2020-05-05 | 贵州省中国科学院天然产物化学重点实验室 | 双苄基异喹啉衍生物及其在制备用于治疗或预防肿瘤的药物中的用途 |
| CN108904500A (zh) * | 2018-08-13 | 2018-11-30 | 河北工业大学 | 双醚键型BBI在抑制Kv10.1离子通道活性中的应用和药物 |
| WO2020150638A1 (en) * | 2019-01-18 | 2020-07-23 | City Of Hope | Berbamine derivatives and methods of use thereof |
| CN112125914B (zh) * | 2019-06-25 | 2024-02-13 | 杭州卫本药业有限公司 | 5-取代的小檗胺衍生物，其制备方法和应用 |
| CN114031623B (zh) * | 2021-11-12 | 2023-04-11 | 山西医科大学 | 一种c14位氨基取代粉防己碱衍生物及其制备和应用 |
| CN116731031A (zh) * | 2023-06-16 | 2023-09-12 | 贵州药法自然医药科技有限公司 | 芬氏唐松草碱衍生物及其应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1810247A (zh) * | 2005-01-28 | 2006-08-02 | 中国医学科学院血液学研究所 | 小檗胺衍生物ebb在抑制人体肿瘤细胞侵袭转移的药物应用 |
| CN101273989A (zh) * | 2008-04-09 | 2008-10-01 | 浙江大学 | 一类小檗胺衍生物及其盐的应用 |
| CN101780082A (zh) * | 2009-01-20 | 2010-07-21 | 张宏 | 双苄基异喹啉类生物碱作为抗感染药物增效剂的用途及其药物组合物 |
| US20100298369A1 (en) * | 2009-05-19 | 2010-11-25 | David Horne | Berbamine derivatives |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134382A (ja) * | 1988-11-14 | 1990-05-23 | Kaken Shiyouyaku Kk | ビスベンジルイソキノリン誘導体 |
| JP2627666B2 (ja) * | 1989-07-13 | 1997-07-09 | 花王株式会社 | 抗アレルギー剤 |
| US5025020A (en) | 1989-09-28 | 1991-06-18 | Cancer Biologics Of America, Inc. | Use of tetrandrine and its derivatives to treat malaria |
| CN1111160C (zh) * | 2000-09-08 | 2003-06-11 | 成都康弘制药有限公司 | 双苄基异喹啉类生物碱和药物组合物及用途 |
| US6617335B1 (en) * | 2002-05-02 | 2003-09-09 | Kanghong Usa, Inc. | Preparation and drug composition of bis-benzyl-isoquinoline class alkaloids |
| CN101423519A (zh) * | 2008-11-28 | 2009-05-06 | 浙江大学 | 粉防己碱有机酸盐及制备方法和应用 |
| CN102875560B (zh) * | 2011-07-15 | 2014-12-03 | 复旦大学 | 5-取代粉防己碱类化合物及其在制备抗癌药增敏剂中的用途 |
-
2012
- 2012-08-20 EP EP12825975.1A patent/EP2767538B1/en not_active Not-in-force
- 2012-08-20 DK DK12825975.1T patent/DK2767538T3/en active
- 2012-08-20 WO PCT/CN2012/080384 patent/WO2013026383A1/zh not_active Ceased
- 2012-08-20 CN CN201280027456.6A patent/CN103635475B/zh not_active Expired - Fee Related
- 2012-08-20 JP JP2014526373A patent/JP5976810B2/ja not_active Expired - Fee Related
- 2012-08-20 US US14/239,759 patent/US9133207B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1810247A (zh) * | 2005-01-28 | 2006-08-02 | 中国医学科学院血液学研究所 | 小檗胺衍生物ebb在抑制人体肿瘤细胞侵袭转移的药物应用 |
| CN101273989A (zh) * | 2008-04-09 | 2008-10-01 | 浙江大学 | 一类小檗胺衍生物及其盐的应用 |
| CN101780082A (zh) * | 2009-01-20 | 2010-07-21 | 张宏 | 双苄基异喹啉类生物碱作为抗感染药物增效剂的用途及其药物组合物 |
| US20100298369A1 (en) * | 2009-05-19 | 2010-11-25 | David Horne | Berbamine derivatives |
Non-Patent Citations (2)
| Title |
|---|
| 吲哚啉-2-酮和小檗胺衍生物的设计、合成及其生物活性研究;谢进文;《浙江大学博士学位论文》;20091015;全文，尤其57-114页 * |
| 四种小檗胺衍生物对钙调素诱导的肌球蛋白轻链激酶的抑制作用;贡岳松，等;《中国药科大学学报》;19911231;第22卷(第2期);93-95 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112480140A (zh) * | 2020-12-28 | 2021-03-12 | 杭州医学院 | C5-位取代汉防己甲素衍生物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2767538B1 (en) | 2016-07-13 |
| WO2013026383A1 (zh) | 2013-02-28 |
| US20140343047A1 (en) | 2014-11-20 |
| JP5976810B2 (ja) | 2016-08-24 |
| US9133207B2 (en) | 2015-09-15 |
| DK2767538T3 (en) | 2016-12-12 |
| JP2014524449A (ja) | 2014-09-22 |
| EP2767538A1 (en) | 2014-08-20 |
| CN103635475A (zh) | 2014-03-12 |
| EP2767538A4 (en) | 2015-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2767538T3 (en) | TETRANDRINDERIVATER with substituted 5-CARBON, PRODUCTION PROCESS AND USE THEREOF | |
| JP6286365B2 (ja) | １−オキソ／アシル化−１４−アシル化オリドニン誘導体、その調製方法及び適用 | |
| CN104039794B (zh) | 7‑位取代的汉防己乙素衍生物、及其制备方法和应用 | |
| CN103946231B (zh) | 齐墩果酸酰胺化衍生物、及其制备方法和应用 | |
| CN102234259A (zh) | 含笑内酯衍生物,其药物组合物及其制备方法和用途 | |
| WO2012031563A1 (zh) | 杂环氨基小檗胺衍生物、其制备方法和应用 | |
| DK2862869T3 (en) | ACYLATED DERIVATIVES OF POLYPHYLLINE I, METHOD OF PREPARING IT AND USING THEREOF | |
| CN104804016B (zh) | 四并环类间变性淋巴瘤激酶抑制剂 | |
| JP6068472B2 (ja) | アミノ化ホモハリントニン誘導体、その調製方法及び使用 | |
| JP6059734B2 (ja) | ２−アルキル−又は２−アリール−置換タンシノン誘導体、その調製方法及び適用 | |
| CN102712655B (zh) | 小檗胺的二酰亚胺化衍生物、其制备方法和应用 | |
| CN109896986B (zh) | 木脂素类天然产物4-o-甲基三白草醇的结构简化物，其制法和其药物组合物与用途 | |
| CN103635476B (zh) | 高三尖杉酯碱的酰化衍生物、及其制备方法和应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20160608 |