CN103945852B - 2-位取代的齐墩果酸衍生物、及其制备方法和应用 - Google Patents
2-位取代的齐墩果酸衍生物、及其制备方法和应用 Download PDFInfo
- Publication number
- CN103945852B CN103945852B CN201280056729.XA CN201280056729A CN103945852B CN 103945852 B CN103945852 B CN 103945852B CN 201280056729 A CN201280056729 A CN 201280056729A CN 103945852 B CN103945852 B CN 103945852B
- Authority
- CN
- China
- Prior art keywords
- oleanolic acid
- compound
- cancer
- substituted
- methyl ester
- 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
- MIJYXULNPSFWEK-GTOFXWBISA-N CC(C)(CC1)C[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O Chemical compound CC(C)(CC1)C[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 1
- MDZKJHQSJHYOHJ-LLICELPBSA-N CC(C)(CC1)C[C@H]2C3=CC[C@H]([C@@](C)(C[C@H]4O)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O Chemical compound CC(C)(CC1)C[C@H]2C3=CC[C@H]([C@@](C)(C[C@H]4O)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O MDZKJHQSJHYOHJ-LLICELPBSA-N 0.000 description 1
- RYOSSYYUQCPWCH-NJEFVDHSSA-N CC(C)(CC[C@@]1(CC[C@H]2[C@]3(C)CC4)C(OC)=O)C[C@H]1C2=CC[C@]3(C)[C@@](C)(CC1C(O)=O)[C@@H]4C(C)(C)C1=O Chemical compound CC(C)(CC[C@@]1(CC[C@H]2[C@]3(C)CC4)C(OC)=O)C[C@H]1C2=CC[C@]3(C)[C@@](C)(CC1C(O)=O)[C@@H]4C(C)(C)C1=O RYOSSYYUQCPWCH-NJEFVDHSSA-N 0.000 description 1
- WCGUUGGRBIKTOS-GPOJBZKASA-N C[C@H](CC1)[C@H](C)[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O Chemical compound C[C@H](CC1)[C@H](C)[C@H]2C3=CC[C@H]([C@@](C)(CC4)[C@@H](CC5)C(C)(C)[C@H]4O)[C@]5(C)[C@]3(C)CC[C@@]12C(O)=O WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201280056729.XA CN103945852B (zh) | 2011-12-01 | 2012-11-30 | 2-位取代的齐墩果酸衍生物、及其制备方法和应用 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011083288 | 2011-12-01 | ||
| CNPCT/CN2011/083288 | 2011-12-01 | ||
| PCT/CN2012/085652 WO2013079018A1 (zh) | 2011-12-01 | 2012-11-30 | 2-位取代的齐墩果酸衍生物、及其制备方法和应用 |
| CN201280056729.XA CN103945852B (zh) | 2011-12-01 | 2012-11-30 | 2-位取代的齐墩果酸衍生物、及其制备方法和应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103945852A CN103945852A (zh) | 2014-07-23 |
| CN103945852B true CN103945852B (zh) | 2016-10-19 |
Family
ID=48534679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280056729.XA Expired - Fee Related CN103945852B (zh) | 2011-12-01 | 2012-11-30 | 2-位取代的齐墩果酸衍生物、及其制备方法和应用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9156801B2 (enExample) |
| EP (1) | EP2786757B1 (enExample) |
| JP (1) | JP6211527B2 (enExample) |
| CN (1) | CN103945852B (enExample) |
| DK (1) | DK2786757T3 (enExample) |
| NO (1) | NO2786757T3 (enExample) |
| WO (1) | WO2013079018A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105213531A (zh) * | 2015-10-14 | 2016-01-06 | 三峡大学 | 木瓜总三萜及其组分在制药中的应用 |
| CA3075729A1 (en) | 2017-09-14 | 2019-03-21 | Phoenix Biotechnology, Inc. | Use of oleandrin to treatn viral infection |
| CN111417384A (zh) | 2017-09-14 | 2020-07-14 | 菲尼克斯生物技术公司 | 用于治疗神经系统病况的方法和改进的神经保护性组合物 |
| US9969768B1 (en) * | 2017-11-16 | 2018-05-15 | King Saud University | Oleanolic acid methyl ester derivatives |
| US10137138B1 (en) | 2018-05-29 | 2018-11-27 | King Saud University | Sulfonylurea derivatives of oleanolic acid |
| KR20220151038A (ko) | 2020-03-31 | 2022-11-11 | 피닉스 바이오테크놀러지 인코포레이티드. | 코로나바이러스 감염 예방를 위한 조성물 |
| EP4295854A3 (en) | 2020-03-31 | 2024-04-03 | Phoenix Biotechnology, Inc. | Method and compositions for treating coronavirus infection |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1874765A (zh) * | 2003-09-22 | 2006-12-06 | 应用技术株式会社 | 胰岛素初期分泌促进剂 |
| WO2009129545A1 (en) * | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring |
| WO2009146216A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| CN101974059A (zh) * | 2010-09-10 | 2011-02-16 | 武汉巨惠绿色产业发展有限公司 | 一种齐墩果酸结构类似物的制备及其半合成齐墩果酸的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07583B2 (ja) * | 1990-11-21 | 1995-01-11 | 北海道糖業株式会社 | 水溶性五環性トリテルペン包接化合物及びその製造方法並びにそれを利用した食品、飲料、口腔用組成物 |
| CN1164609C (zh) | 2002-10-24 | 2004-09-01 | 青岛海洋大学 | 一种齐墩果酸乳糖缀合物及其制备方法和用途 |
| CN102133219A (zh) | 2010-09-27 | 2011-07-27 | 林秀坤 | 齐墩果酸的抗宫颈癌作用及其药物制剂 |
| CN102151275A (zh) | 2010-11-07 | 2011-08-17 | 林秀坤 | 齐墩果酸的抗胰腺癌作用及其药物制剂 |
| CN102070697A (zh) | 2010-12-09 | 2011-05-25 | 中国药科大学 | 一种齐墩果酸衍生物、其制备方法及用途 |
-
2012
- 2012-11-30 DK DK12852723.1T patent/DK2786757T3/da active
- 2012-11-30 JP JP2014543761A patent/JP6211527B2/ja not_active Expired - Fee Related
- 2012-11-30 NO NO12852723A patent/NO2786757T3/no unknown
- 2012-11-30 CN CN201280056729.XA patent/CN103945852B/zh not_active Expired - Fee Related
- 2012-11-30 US US14/362,017 patent/US9156801B2/en not_active Expired - Fee Related
- 2012-11-30 EP EP12852723.1A patent/EP2786757B1/en not_active Not-in-force
- 2012-11-30 WO PCT/CN2012/085652 patent/WO2013079018A1/zh not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1874765A (zh) * | 2003-09-22 | 2006-12-06 | 应用技术株式会社 | 胰岛素初期分泌促进剂 |
| WO2009129545A1 (en) * | 2008-04-18 | 2009-10-22 | Reata Pharmaceuticals, Inc. | Antioxidant inflammation modulators: oleanolic acid derivatives with saturation in the c-ring |
| WO2009146216A2 (en) * | 2008-04-18 | 2009-12-03 | Reata Pharmaceuticals. Inc. | Antioxidant inflammation modulators: novel derivatives of oleanolic acid |
| CN101974059A (zh) * | 2010-09-10 | 2011-02-16 | 武汉巨惠绿色产业发展有限公司 | 一种齐墩果酸结构类似物的制备及其半合成齐墩果酸的方法 |
Non-Patent Citations (1)
| Title |
|---|
| Structure-activity relationships of oleanane- and ursanetype triterpenoids;Hua SUN et al.;《Botnical Studies》;20061231;第47卷;339-368 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2786757B1 (en) | 2017-08-16 |
| EP2786757A4 (en) | 2015-08-12 |
| NO2786757T3 (enExample) | 2018-01-13 |
| JP2014534268A (ja) | 2014-12-18 |
| WO2013079018A1 (zh) | 2013-06-06 |
| US9156801B2 (en) | 2015-10-13 |
| US20140343064A1 (en) | 2014-11-20 |
| CN103945852A (zh) | 2014-07-23 |
| JP6211527B2 (ja) | 2017-10-11 |
| DK2786757T3 (da) | 2017-11-20 |
| EP2786757A1 (en) | 2014-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | 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 | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180516 Address after: Room 102, No. 131, Kai Qing Road, Pudong New Area, Shanghai Patentee after: Benson Pharmaceutical (Shanghai) Co.,Ltd. Address before: 310051 4 4, 6 Jiangling Road, Binjiang District, Hangzhou, Zhejiang. Patentee before: HANGZHOU BENSHENG PHARMACEUTICAL Co.,Ltd. |
|
| 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: 20161019 |