AU2005207029B2 - Novel sirtuin activating compounds and methods for making the same - Google Patents
Novel sirtuin activating compounds and methods for making the same Download PDFInfo
- Publication number
- AU2005207029B2 AU2005207029B2 AU2005207029A AU2005207029A AU2005207029B2 AU 2005207029 B2 AU2005207029 B2 AU 2005207029B2 AU 2005207029 A AU2005207029 A AU 2005207029A AU 2005207029 A AU2005207029 A AU 2005207029A AU 2005207029 B2 AU2005207029 B2 AU 2005207029B2
- Authority
- AU
- Australia
- Prior art keywords
- stilbene
- dihydroxy
- hydroxy
- compound according
- alkyl
- 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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- 150000001875 compounds Chemical class 0.000 title claims abstract description 138
- 238000000034 method Methods 0.000 title abstract description 41
- 108050002485 Sirtuin Proteins 0.000 title description 15
- 102000011990 Sirtuin Human genes 0.000 title description 15
- 230000003213 activating effect Effects 0.000 title description 2
- 235000021286 stilbenes Nutrition 0.000 claims abstract description 138
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 66
- 125000003118 aryl group Chemical group 0.000 claims abstract description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 239000002537 cosmetic Substances 0.000 claims abstract description 13
- -1 I-butyl Chemical group 0.000 claims description 198
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 148
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 139
- 239000000203 mixture Substances 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 235000015872 dietary supplement Nutrition 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 abstract description 50
- 229940016667 resveratrol Drugs 0.000 abstract description 48
- 239000003446 ligand Substances 0.000 abstract description 47
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 abstract description 46
- 235000021283 resveratrol Nutrition 0.000 abstract description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 41
- 238000005859 coupling reaction Methods 0.000 abstract description 35
- 229910052736 halogen Inorganic materials 0.000 abstract description 32
- 150000002367 halogens Chemical class 0.000 abstract description 32
- 230000008878 coupling Effects 0.000 abstract description 29
- 238000010168 coupling process Methods 0.000 abstract description 29
- 229910052799 carbon Inorganic materials 0.000 abstract description 28
- 230000008569 process Effects 0.000 abstract description 25
- 125000006241 alcohol protecting group Chemical group 0.000 abstract description 24
- 150000001721 carbon Chemical group 0.000 abstract description 23
- 150000004820 halides Chemical class 0.000 abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 7
- 239000007819 coupling partner Substances 0.000 abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 235000013305 food Nutrition 0.000 abstract description 3
- 150000001629 stilbenes Chemical class 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 90
- 239000003795 chemical substances by application Substances 0.000 description 71
- 239000000243 solution Substances 0.000 description 67
- 239000002904 solvent Substances 0.000 description 59
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 56
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 239000002585 base Substances 0.000 description 45
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical class OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 40
- 230000010933 acylation Effects 0.000 description 37
- 238000005917 acylation reaction Methods 0.000 description 37
- 239000003054 catalyst Substances 0.000 description 37
- 239000002253 acid Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- UIAFKZKHHVMJGS-UHFFFAOYSA-N beta-resorcylic acid Natural products OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 33
- 239000000725 suspension Substances 0.000 description 33
- 150000002148 esters Chemical class 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003223 protective agent Substances 0.000 description 26
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 25
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 24
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
- 239000011734 sodium Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 150000001412 amines Chemical class 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000002140 halogenating effect Effects 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 19
- 125000006239 protecting group Chemical group 0.000 description 19
- UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- 239000012442 inert solvent Substances 0.000 description 18
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 17
- 239000006071 cream Substances 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 235000013824 polyphenols Nutrition 0.000 description 17
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 16
- 150000003440 styrenes Chemical class 0.000 description 16
- 239000005711 Benzoic acid Substances 0.000 description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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- 235000010233 benzoic acid Nutrition 0.000 description 15
- AQIHMSVIAGNIDM-UHFFFAOYSA-N benzoyl bromide Chemical compound BrC(=O)C1=CC=CC=C1 AQIHMSVIAGNIDM-UHFFFAOYSA-N 0.000 description 15
- WPCXDBCEDWUSOU-UHFFFAOYSA-N benzoyl iodide Chemical compound IC(=O)C1=CC=CC=C1 WPCXDBCEDWUSOU-UHFFFAOYSA-N 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 15
- 229910052723 transition metal Inorganic materials 0.000 description 15
- 150000003624 transition metals Chemical class 0.000 description 15
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 14
- 238000005658 halogenation reaction Methods 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- UENRXLSRMCSUSN-UHFFFAOYSA-N 3,5-diaminobenzoic acid Chemical compound NC1=CC(N)=CC(C(O)=O)=C1 UENRXLSRMCSUSN-UHFFFAOYSA-N 0.000 description 13
- 238000007341 Heck reaction Methods 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
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- 239000000843 powder Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 230000026030 halogenation Effects 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000010511 deprotection reaction Methods 0.000 description 11
- 238000003818 flash chromatography Methods 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 10
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
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- 239000012190 activator Substances 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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| US53762204P | 2004-01-20 | 2004-01-20 | |
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| US61653704P | 2004-10-06 | 2004-10-06 | |
| US60/616,537 | 2004-10-06 | ||
| PCT/US2005/002229 WO2005069998A2 (en) | 2004-01-20 | 2005-01-19 | Novel sirtuin activating compounds and methods for making the same |
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| AU2005207029A1 AU2005207029A1 (en) | 2005-08-04 |
| AU2005207029B2 true AU2005207029B2 (en) | 2011-09-01 |
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| AU2005207029A Ceased AU2005207029B2 (en) | 2004-01-20 | 2005-01-19 | Novel sirtuin activating compounds and methods for making the same |
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Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2593576C (en) | 2004-01-20 | 2013-04-23 | Brigham Young University | Novel sirtuin activating compounds and methods for making the same |
| JP2009500357A (ja) * | 2005-07-07 | 2009-01-08 | サートリス ファーマシューティカルズ， インコーポレイテッド | 肥満、インスリン抵抗性障害およびミトコンドリア関連障害を処置または予防するための方法および関連する組成物 |
| AU2006278505B2 (en) | 2005-08-04 | 2013-01-17 | Sirtris Pharmaceuticals, Inc. | Benzothiazoles and thiazolopyridines as sirtuin modulators |
| CN101296693B (zh) * | 2005-10-26 | 2012-07-04 | 花王株式会社 | 持久力提高剂 |
| JP2009521408A (ja) * | 2005-12-02 | 2009-06-04 | サートリス ファーマシューティカルズ， インコーポレイテッド | Ｃｄｃ２様キナーゼ（ＣＬＫ）のモジュレータおよびその使用方法 |
| FR2895261B1 (fr) * | 2005-12-22 | 2009-06-05 | Vincience Sa | Utilisation d'un extrait de riz en tant qu'agent actif inducteur de la synthese des proteines sirt dans les cellules de la peau |
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| TW200918542A (en) | 2007-06-20 | 2009-05-01 | Sirtris Pharmaceuticals Inc | Sirtuin modulating compounds |
| US20090035240A1 (en) * | 2007-07-31 | 2009-02-05 | Maes Daniel H | Aqueous Based Cosmetic Compositions Containing Resveratrol Derivatives And An Aqueous Phase Structuring Agent |
| US20090035236A1 (en) * | 2007-07-31 | 2009-02-05 | Maes Daniel H | Emulsion Cosmetic Compositions Containing Resveratrol Derivatives And An Oil Phase Structuring Agent |
| EP2185128B1 (en) * | 2007-07-31 | 2018-08-08 | ELC Management LLC | Cosmetic compositions containing resveratrol derivatives |
| US8080583B2 (en) * | 2007-07-31 | 2011-12-20 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and linear or branched silicone |
| US9295621B2 (en) | 2007-07-31 | 2016-03-29 | Elc Management Llc | Emulsion cosmetic compositions containing resveratrol derivatives and silicone surfactant |
| US8344024B2 (en) | 2007-07-31 | 2013-01-01 | Elc Management Llc | Anhydrous cosmetic compositions containing resveratrol derivatives |
| US20090068132A1 (en) * | 2007-09-08 | 2009-03-12 | Daniela Bratescu | Resveratrol Ferulate Compounds, Compositions Containing The Compounds, And Methods Of Using The Same |
| FR2921921B1 (fr) | 2007-10-03 | 2011-08-19 | Clariant Specialty Fine Chem F | Procede de synthese de composes polyhydroxystilbeniques. |
| WO2009099643A1 (en) * | 2008-02-07 | 2009-08-13 | The J. David Gladstone Institutes | Use of sirt1 activators or inhibitors to modulate an immune response |
| US8024504B2 (en) * | 2008-06-26 | 2011-09-20 | Microsoft Corporation | Processor interrupt determination |
| AU2009333588A1 (en) | 2008-12-08 | 2011-07-21 | Northwestern University | Method of modulating HSF-1 |
| US20130123357A1 (en) * | 2010-04-13 | 2013-05-16 | Brigham Young University | Methods for Providing Enhanced Resveratrol Activity Using 4-Acetoxy-Resveratrol |
| CN102050705B (zh) * | 2010-11-02 | 2013-07-31 | 华润赛科药业有限责任公司 | 一种脱羰基heck反应制备白藜芦醇的方法 |
| AU2012275841A1 (en) | 2011-06-27 | 2014-01-16 | The Jackson Laboratory | Methods and compositions for treatment of cancer and autoimmune disease |
| FR2977891A1 (fr) * | 2011-07-11 | 2013-01-18 | Centre Nat Rech Scient | Procede de preparation du trans-resveratrol et de ses analogues |
| RU2594281C2 (ru) * | 2013-04-03 | 2016-08-10 | Чайна Медикал Юнивёсити | Стильбеноидные соединения в качестве ингибиторов плоскоклеточной карциномы и гепатомы и их применения |
| US10301248B2 (en) | 2014-02-06 | 2019-05-28 | Biocogent, Llc | Compositions and methods comprising resveratrol |
| EP3134421B1 (en) | 2014-04-24 | 2022-04-20 | Institut National de la Santé et de la Recherche Médicale (INSERM) | New lipophenol compounds and uses thereof |
| TW201702218A (zh) | 2014-12-12 | 2017-01-16 | 美國杰克森實驗室 | 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法 |
| KR101845203B1 (ko) | 2017-09-22 | 2018-04-05 | 동아대학교 산학협력단 | 라우르산 유도체, 이의 제조방법 및 이를 포함하는 항암제 |
| EP3482758A1 (en) | 2017-11-10 | 2019-05-15 | Universite De Montpellier | New uses of lipophenolic compounds |
| AU2019360206A1 (en) * | 2018-10-16 | 2021-05-27 | President And Fellows Of Harvard College | SIRT1 activating compounds |
| KR102144628B1 (ko) * | 2019-01-11 | 2020-08-13 | 동아대학교 산학협력단 | 라우르산 유도체를 포함하는 방광암의 예방, 개선 또는 치료용 조성물 |
| KR102381035B1 (ko) * | 2020-04-14 | 2022-03-31 | 서울대학교산학협력단 | 게일루사신 유도체의 신규한 합성방법 |
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-
2005
- 2005-01-19 CA CA2593576A patent/CA2593576C/en not_active Expired - Fee Related
- 2005-01-19 EP EP05711939.8A patent/EP1753708B1/en not_active Not-in-force
- 2005-01-19 WO PCT/US2005/002229 patent/WO2005069998A2/en active Application Filing
- 2005-01-19 CA CA2805795A patent/CA2805795C/en not_active Expired - Fee Related
- 2005-01-19 AU AU2005207029A patent/AU2005207029B2/en not_active Ceased
- 2005-01-19 US US10/597,335 patent/US7714161B2/en not_active Expired - Fee Related
-
2009
- 2009-07-15 US US12/503,239 patent/US8841477B2/en not_active Expired - Fee Related
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| EP1336602A1 (en) * | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1753708A4 (en) | 2007-12-26 |
| EP1753708A2 (en) | 2007-02-21 |
| US20080255382A1 (en) | 2008-10-16 |
| WO2005069998A3 (en) | 2006-01-05 |
| US7714161B2 (en) | 2010-05-11 |
| CA2805795C (en) | 2016-11-08 |
| AU2005207029A1 (en) | 2005-08-04 |
| EP1753708B1 (en) | 2018-02-21 |
| WO2005069998A2 (en) | 2005-08-04 |
| US20100185006A1 (en) | 2010-07-22 |
| CA2593576A1 (en) | 2006-08-04 |
| CA2805795A1 (en) | 2006-08-04 |
| CA2593576C (en) | 2013-04-23 |
| US8841477B2 (en) | 2014-09-23 |
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