JP2015500801A5 - - Google Patents
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- Publication number
- JP2015500801A5 JP2015500801A5 JP2014543762A JP2014543762A JP2015500801A5 JP 2015500801 A5 JP2015500801 A5 JP 2015500801A5 JP 2014543762 A JP2014543762 A JP 2014543762A JP 2014543762 A JP2014543762 A JP 2014543762A JP 2015500801 A5 JP2015500801 A5 JP 2015500801A5
- Authority
- JP
- Japan
- Prior art keywords
- tanshinone
- cancer
- methyl
- acceptable salt
- pharmaceutically acceptable
- 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.)
- Granted
Links
- AIGAZQPHXLWMOJ-UHFFFAOYSA-N tanshinone IIA Natural products C1=CC2=C(C)C=CC=C2C(C(=O)C2=O)=C1C1=C2C(C)=CO1 AIGAZQPHXLWMOJ-UHFFFAOYSA-N 0.000 claims 24
- -1 methylene tanshinone I derivatives Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 3
- 208000032612 Glial tumor Diseases 0.000 claims 3
- 206010018338 Glioma Diseases 0.000 claims 3
- 206010023825 Laryngeal cancer Diseases 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010025323 Lymphomas Diseases 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- 208000034578 Multiple myelomas Diseases 0.000 claims 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 201000010881 cervical cancer Diseases 0.000 claims 3
- 208000006990 cholangiocarcinoma Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 201000004101 esophageal cancer Diseases 0.000 claims 3
- 206010017758 gastric cancer Diseases 0.000 claims 3
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 201000007270 liver cancer Diseases 0.000 claims 3
- 208000014018 liver neoplasm Diseases 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 208000018026 neoplasm of middle ear Diseases 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 201000008968 osteosarcoma Diseases 0.000 claims 3
- 229910052760 oxygen Chemical group 0.000 claims 3
- 239000001301 oxygen Chemical group 0.000 claims 3
- 201000002528 pancreatic cancer Diseases 0.000 claims 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 3
- 201000011549 stomach cancer Diseases 0.000 claims 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 210000001989 nasopharynx Anatomy 0.000 claims 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- RCWJMKCTHJPXJV-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-1,4-benzoquinone Chemical class O=C1C=C(N2CC2)C(=O)C=C1N1CC1 RCWJMKCTHJPXJV-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 1
- 229930195712 glutamate Natural products 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000007031 hydroxymethylation reaction Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2011/083261 | 2011-11-30 | ||
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2015500801A JP2015500801A (ja) | 2015-01-08 |
| JP2015500801A5 true JP2015500801A5 (enExample) | 2016-01-14 |
| JP6149043B2 JP6149043B2 (ja) | 2017-06-14 |
Family
ID=48534682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014543762A Expired - Fee Related JP6149043B2 (ja) | 2011-11-30 | 2012-11-30 | ２−アミノ化メチレン又は２−エステル化メチレンタンシノン誘導体、並びにその調製方法及び使用 |
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) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2012
- 2012-11-30 DK DK12854507.6T patent/DK2786990T3/en active
- 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
- 2012-11-30 WO PCT/CN2012/085660 patent/WO2013079022A1/zh not_active Ceased
- 2012-11-30 EP EP12854507.6A patent/EP2786990B1/en not_active Not-in-force