DK2786990T3 - 2-AMINED METHYLE OR 2-ESTERIFIED METHYLENE-TANSHINON DERIVATIVES, AND METHOD OF PREPARING AND USING THEREOF - Google Patents
2-AMINED METHYLE OR 2-ESTERIFIED METHYLENE-TANSHINON DERIVATIVES, AND METHOD OF PREPARING AND USING THEREOF Download PDFInfo
- Publication number
- DK2786990T3 DK2786990T3 DK12854507.6T DK12854507T DK2786990T3 DK 2786990 T3 DK2786990 T3 DK 2786990T3 DK 12854507 T DK12854507 T DK 12854507T DK 2786990 T3 DK2786990 T3 DK 2786990T3
- Authority
- DK
- Denmark
- Prior art keywords
- tanshinone
- methyl
- formula
- compound
- pharmaceutically acceptable
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 36
- AIGAZQPHXLWMOJ-UHFFFAOYSA-N Tanshinone I Chemical class C1=CC2=C(C)C=CC=C2C(C(=O)C2=O)=C1C1=C2C(C)=CO1 AIGAZQPHXLWMOJ-UHFFFAOYSA-N 0.000 claims description 153
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy Chemical group 0.000 claims description 70
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 208000032839 leukemia Diseases 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- 229910052760 oxygen Chemical group 0.000 claims description 10
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- 125000006413 ring segment Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
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- 208000034578 Multiple myelomas Diseases 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 claims description 5
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 5
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- 150000001412 amines Chemical class 0.000 claims description 5
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 150000001263 acyl chlorides Chemical class 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 206010017758 gastric cancer Diseases 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000007031 hydroxymethylation reaction Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- YOLQOHRXBGFZED-UHFFFAOYSA-N 7-methoxy-7-oxoheptanoic acid Chemical group COC(=O)CCCCCC(O)=O YOLQOHRXBGFZED-UHFFFAOYSA-N 0.000 claims 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical group COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 9
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011083261 | 2011-11-30 | ||
| PCT/CN2012/085660 WO2013079022A1 (zh) | 2011-11-30 | 2012-11-30 | 2-位胺化亚甲基或2-位酯化亚甲基丹参酮衍生物、及其制备方法和应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2786990T3 true DK2786990T3 (en) | 2018-11-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12854507.6T DK2786990T3 (en) | 2011-11-30 | 2012-11-30 | 2-AMINED METHYLE OR 2-ESTERIFIED METHYLENE-TANSHINON DERIVATIVES, AND METHOD OF PREPARING AND USING THEREOF |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9328083B2 (enExample) |
| EP (1) | EP2786990B1 (enExample) |
| JP (1) | JP6149043B2 (enExample) |
| DK (1) | DK2786990T3 (enExample) |
| WO (1) | WO2013079022A1 (enExample) |
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|---|---|---|---|---|
| JP6059734B2 (ja) * | 2011-11-30 | 2017-01-11 | ハンジョウ ベンシェン ファーマシューティカル シーオー．， エルティーディー．Ｈａｎｇｚｈｏｕ Ｂｅｎｓｈｅｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｃｏ．， Ｌｔｄ． | 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 |
| CN105884723B (zh) * | 2014-12-25 | 2019-08-02 | 上海三帆生物医药科技有限公司 | 丹参酮衍生物、其制备方法及其应用 |
| CN105884857B (zh) * | 2015-01-23 | 2018-10-12 | 上海三帆生物医药科技有限公司 | 丹参酮衍生物、其制备方法及其应用 |
| CN106831934B (zh) * | 2016-12-26 | 2018-09-21 | 郑州大学 | 一种丹参酮类化合物15位酰胺类衍生物及其制备工艺和应用 |
| CN106810593B (zh) * | 2016-12-26 | 2018-12-04 | 郑州大学 | 一种丹参酮类化合物17位酯化衍生物及其制备工艺和应用 |
| CN111000851B (zh) * | 2019-12-31 | 2021-09-07 | 扬州大学 | 丹参酮i在制备肿瘤细胞自噬诱导剂药物中的应用 |
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| CN1837200A (zh) | 2006-04-26 | 2006-09-27 | 秦引林 | 丹参酮ⅰ衍生物及其在制药中的应用 |
| CN100387585C (zh) | 2006-04-26 | 2008-05-14 | 秦引林 | 丹参酮ⅰ衍生物及其在制药中的应用 |
| KR20080047956A (ko) * | 2006-11-27 | 2008-05-30 | 주식회사 엠디바이오알파 | 발기부전의 치료 및 예방을 위한 약제 조성물 |
| CN101012270A (zh) | 2007-01-26 | 2007-08-08 | 广东工业大学 | 丹参酮衍生物及在制备醛糖还原酶抑制剂药物中的应用 |
| CN101274925A (zh) * | 2007-03-29 | 2008-10-01 | 中国科学院上海药物研究所 | 一类萘并呋喃邻醌化合物及其制备方法和用途 |
| JP2011500557A (ja) * | 2007-10-11 | 2011-01-06 | マゼンス インコーポレイテッド | ナフトキノン系化合物の微粒化粒子を含有する医薬組成物 |
| KR20090073381A (ko) * | 2007-12-31 | 2009-07-03 | 주식회사 머젠스 | 심장질환의 치료 및 예방을 위한 약제 조성물 |
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- 2012-11-30 US US14/361,548 patent/US9328083B2/en not_active Expired - Fee Related
- 2012-11-30 JP JP2014543762A patent/JP6149043B2/ja not_active Expired - Fee Related
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| WO2013079022A1 (zh) | 2013-06-06 |
| EP2786990A4 (en) | 2015-07-15 |
| EP2786990A1 (en) | 2014-10-08 |
| JP2015500801A (ja) | 2015-01-08 |
| JP6149043B2 (ja) | 2017-06-14 |
| US20150126552A1 (en) | 2015-05-07 |
| US9328083B2 (en) | 2016-05-03 |
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