AU2011218391B2 - 10'-fluorinated vinca alkaloids provide enhanced biological activity against MDR cancer cells - Google Patents
10'-fluorinated vinca alkaloids provide enhanced biological activity against MDR cancer cells Download PDFInfo
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- AU2011218391B2 AU2011218391B2 AU2011218391A AU2011218391A AU2011218391B2 AU 2011218391 B2 AU2011218391 B2 AU 2011218391B2 AU 2011218391 A AU2011218391 A AU 2011218391A AU 2011218391 A AU2011218391 A AU 2011218391A AU 2011218391 B2 AU2011218391 B2 AU 2011218391B2
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- fluoro
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- vinca alkaloid
- alkaloid compound
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 150000003858 primary carboxamides Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- FPTVEOPNJVOJBF-UHFFFAOYSA-M sodium;oxolane;hydroxide Chemical compound [OH-].[Na+].C1CCOC1 FPTVEOPNJVOJBF-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 108010072897 transcription factor Brn-2 Proteins 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30678610P | 2010-02-22 | 2010-02-22 | |
| US61/306,786 | 2010-02-22 | ||
| PCT/US2011/024230 WO2011103007A2 (en) | 2010-02-22 | 2011-02-09 | 10'-fluorinated vinca alkaloids provide enhanced biological activity against mdr cancer cells |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2011218391A1 AU2011218391A1 (en) | 2012-09-13 |
| AU2011218391B2 true AU2011218391B2 (en) | 2015-01-22 |
Family
ID=44483528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2011218391A Ceased AU2011218391B2 (en) | 2010-02-22 | 2011-02-09 | 10'-fluorinated vinca alkaloids provide enhanced biological activity against MDR cancer cells |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8940754B2 (https=) |
| EP (1) | EP2539339B1 (https=) |
| JP (1) | JP5542972B2 (https=) |
| AU (1) | AU2011218391B2 (https=) |
| CA (1) | CA2790602C (https=) |
| WO (1) | WO2011103007A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102363622B (zh) * | 2011-11-24 | 2014-01-29 | 四川大学 | 一种化合物及其制备方法和应用 |
| EP2807167A4 (en) * | 2012-01-25 | 2016-01-20 | Demerx Inc | INDOIND AND BENZO FURANKED ISOCHINUCLIDEN DERIVATIVES AND METHOD FOR THE MANUFACTURE THEREOF |
| US9611271B2 (en) | 2012-12-03 | 2017-04-04 | Scripps Research Institute | C20′ urea derivatives of vinca alkaloids |
| HU230462B1 (hu) * | 2013-05-30 | 2016-07-28 | Richter Gedeon Nyrt. | Új bisz-indol alkaloidok mint rákellenes gyógyszerek |
| CA2989550C (en) | 2014-06-18 | 2023-08-08 | Demerx, Inc. | Halogenated indole and benzofuran derivatives of isoquinuclidene and processes for preparing them |
| EP3464289B1 (en) | 2016-05-31 | 2021-04-21 | The Scripps Research Institute | Ultra-potent vinca alkaloids: added molecular complexity further disrupts the tubulin dimer-dimer interface |
| CN106336419B (zh) * | 2016-08-23 | 2018-10-16 | 江苏豪森药业集团有限公司 | 酒石酸长春瑞滨的制备方法 |
| WO2026007326A1 (zh) * | 2024-07-01 | 2026-01-08 | 四川大学 | 长春碱衍生物的制备及其应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998045301A1 (fr) * | 1997-04-10 | 1998-10-15 | Pierre Fabre Medicament | Derives halogenes antimitotiques d'alcaloides de vinca |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU82514A1 (fr) * | 1980-06-10 | 1982-01-20 | Omnium Chimique Sa | Derives n-(vinblastinoyl-23)d'acides amines,leur preparation et leur application therapeutique |
| US6723338B1 (en) | 1999-04-01 | 2004-04-20 | Inex Pharmaceuticals Corporation | Compositions and methods for treating lymphoma |
| WO2005055939A2 (en) * | 2003-12-04 | 2005-06-23 | Amr Technology, Inc. | Vinca derivatives |
| FR2905949B1 (fr) | 2006-09-20 | 2008-11-21 | Pierre Fabre Medicament Sa | Derives fluores de catharanthine, leur preparation et leur utilisation comme precurseurs d'alcaloides dimeres de vinca |
-
2011
- 2011-02-09 WO PCT/US2011/024230 patent/WO2011103007A2/en not_active Ceased
- 2011-02-09 JP JP2012555022A patent/JP5542972B2/ja not_active Expired - Fee Related
- 2011-02-09 CA CA2790602A patent/CA2790602C/en active Active
- 2011-02-09 EP EP11745058.5A patent/EP2539339B1/en active Active
- 2011-02-09 AU AU2011218391A patent/AU2011218391B2/en not_active Ceased
- 2011-02-09 US US13/580,340 patent/US8940754B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998045301A1 (fr) * | 1997-04-10 | 1998-10-15 | Pierre Fabre Medicament | Derives halogenes antimitotiques d'alcaloides de vinca |
Non-Patent Citations (1)
| Title |
|---|
| RUNGUPHAN, W. ET AL., PNAS, 2009, Vol. 106 (33), pages 13673-13678 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013520499A (ja) | 2013-06-06 |
| EP2539339A4 (en) | 2013-08-07 |
| US20120329822A1 (en) | 2012-12-27 |
| AU2011218391A1 (en) | 2012-09-13 |
| CA2790602C (en) | 2016-12-13 |
| JP5542972B2 (ja) | 2014-07-09 |
| US8940754B2 (en) | 2015-01-27 |
| EP2539339A2 (en) | 2013-01-02 |
| WO2011103007A3 (en) | 2012-01-05 |
| CA2790602A1 (en) | 2011-08-25 |
| EP2539339B1 (en) | 2014-05-14 |
| WO2011103007A2 (en) | 2011-08-25 |
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| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |