AU2013240007B2 - Schweinfurthin analogues - Google Patents
Schweinfurthin analogues Download PDFInfo
- Publication number
- AU2013240007B2 AU2013240007B2 AU2013240007A AU2013240007A AU2013240007B2 AU 2013240007 B2 AU2013240007 B2 AU 2013240007B2 AU 2013240007 A AU2013240007 A AU 2013240007A AU 2013240007 A AU2013240007 A AU 2013240007A AU 2013240007 B2 AU2013240007 B2 AU 2013240007B2
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- AU
- Australia
- Prior art keywords
- compound
- mmol
- alkyl
- etoac
- formula
- 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.)
- Ceased
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- 229930194335 schweinfurthin Natural products 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
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- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 201000007455 central nervous system cancer Diseases 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 208000016847 malignant urinary system neoplasm Diseases 0.000 claims 1
- 210000005227 renal system Anatomy 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
- 235000019439 ethyl acetate Nutrition 0.000 description 81
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 49
- 238000000746 purification Methods 0.000 description 40
- 239000012267 brine Substances 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 238000005481 NMR spectroscopy Methods 0.000 description 32
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- 239000000706 filtrate Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
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- 150000001299 aldehydes Chemical class 0.000 description 17
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- 230000015572 biosynthetic process Effects 0.000 description 13
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- 210000004027 cell Anatomy 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
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- 230000001093 anti-cancer Effects 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
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- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 238000000134 MTT assay Methods 0.000 description 4
- 231100000002 MTT assay Toxicity 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KYFMPNVFRAVCNN-UHFFFAOYSA-N P(O)(O)=O.N1C=CC2=CC=CC=C12 Chemical compound P(O)(O)=O.N1C=CC2=CC=CC=C12 KYFMPNVFRAVCNN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- 231100000252 nontoxic Toxicity 0.000 description 4
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000006248 tosyl amino group Chemical group [H]N(*)S(=O)(=O)C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261615725P | 2012-03-26 | 2012-03-26 | |
| US61/615,725 | 2012-03-26 | ||
| PCT/US2013/033722 WO2013148584A1 (en) | 2012-03-26 | 2013-03-25 | Schweinfurthin analogues |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2013240007A1 AU2013240007A1 (en) | 2014-10-16 |
| AU2013240007B2 true AU2013240007B2 (en) | 2017-06-29 |
Family
ID=49261149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013240007A Ceased AU2013240007B2 (en) | 2012-03-26 | 2013-03-25 | Schweinfurthin analogues |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9428493B2 (enExample) |
| EP (1) | EP2831063B1 (enExample) |
| JP (1) | JP2015512404A (enExample) |
| CN (1) | CN104583203B (enExample) |
| AU (1) | AU2013240007B2 (enExample) |
| CA (1) | CA2868508A1 (enExample) |
| ES (1) | ES2655027T3 (enExample) |
| WO (1) | WO2013148584A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12427133B2 (en) * | 2018-02-12 | 2025-09-30 | The Penn State Research Foundation | Combination therapies comprising schweinfurthin compounds for treating cancer |
| CN108658949B (zh) * | 2018-06-29 | 2021-05-25 | 云南大学 | 一种用作抗肿瘤药物的化合物及其生产方法 |
| FR3124946B1 (fr) * | 2021-07-06 | 2024-11-08 | Centre Nat Rech Scient | Nouveaux composés dérivés des schweinfurthines G, E, F |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005092878A2 (en) * | 2004-03-29 | 2005-10-06 | University Of Iowa Research Foundation | Schweinfurthin analogues |
| WO2009158516A1 (en) * | 2008-06-27 | 2009-12-30 | University Of Iowa Research Foundation | Schweinfurthin analogues |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| US8686016B2 (en) * | 2009-04-30 | 2014-04-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Schweinfurthins and uses thereof |
-
2013
- 2013-03-25 EP EP13769473.3A patent/EP2831063B1/en not_active Not-in-force
- 2013-03-25 US US14/388,202 patent/US9428493B2/en not_active Expired - Fee Related
- 2013-03-25 CA CA2868508A patent/CA2868508A1/en not_active Abandoned
- 2013-03-25 AU AU2013240007A patent/AU2013240007B2/en not_active Ceased
- 2013-03-25 JP JP2015503434A patent/JP2015512404A/ja not_active Ceased
- 2013-03-25 WO PCT/US2013/033722 patent/WO2013148584A1/en not_active Ceased
- 2013-03-25 ES ES13769473.3T patent/ES2655027T3/es active Active
- 2013-03-25 CN CN201380027722.XA patent/CN104583203B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005092878A2 (en) * | 2004-03-29 | 2005-10-06 | University Of Iowa Research Foundation | Schweinfurthin analogues |
| WO2009158516A1 (en) * | 2008-06-27 | 2009-12-30 | University Of Iowa Research Foundation | Schweinfurthin analogues |
Non-Patent Citations (2)
| Title |
|---|
| KODET, J. G., "Indole containing analogs of the natural schweinfurthins", Abstract for the 236th ACS National Meeting (MEDI 421), Philadelphia, PA, 20 August 2008 * |
| KODET, J. G., "Studies on heteroaromatic schweinfurthin analogues", PhD Thesis, University of Iowa, 2010 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104583203B (zh) | 2017-06-13 |
| EP2831063A4 (en) | 2015-07-29 |
| EP2831063A1 (en) | 2015-02-04 |
| ES2655027T3 (es) | 2018-02-16 |
| US9428493B2 (en) | 2016-08-30 |
| AU2013240007A1 (en) | 2014-10-16 |
| HK1206745A1 (en) | 2016-01-15 |
| JP2015512404A (ja) | 2015-04-27 |
| US20150045404A1 (en) | 2015-02-12 |
| EP2831063B1 (en) | 2017-10-04 |
| CA2868508A1 (en) | 2013-10-03 |
| WO2013148584A1 (en) | 2013-10-03 |
| CN104583203A (zh) | 2015-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |