AU2009269530A1 - Orally active curcuminoid compounds - Google Patents
Orally active curcuminoid compounds Download PDFInfo
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- AU2009269530A1 AU2009269530A1 AU2009269530A AU2009269530A AU2009269530A1 AU 2009269530 A1 AU2009269530 A1 AU 2009269530A1 AU 2009269530 A AU2009269530 A AU 2009269530A AU 2009269530 A AU2009269530 A AU 2009269530A AU 2009269530 A1 AU2009269530 A1 AU 2009269530A1
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- Prior art keywords
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- compound
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- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 85
- 229930153442 Curcuminoid Natural products 0.000 title description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 111
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 25
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910011255 B2O3 Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 6
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 claims description 6
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 229930194542 Keto Natural products 0.000 claims description 3
- 150000002085 enols Chemical class 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
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- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
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- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 description 73
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- DKICPHDTXJUJIZ-UHFFFAOYSA-N [4-[7-(4-hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] icosa-2,4,6,8,10-pentaenoate Chemical compound C1=C(OC)C(OC(=O)C=CC=CC=CC=CC=CCCCCCCCCC)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=C(O)C(OC)=C1 DKICPHDTXJUJIZ-UHFFFAOYSA-N 0.000 description 8
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- UAZHWIXFOFAWEN-UHFFFAOYSA-N [4-[7-(4-icosa-2,4,6,8,10-pentaenoyloxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-methoxyphenyl] icosa-2,4,6,8,10-pentaenoate Chemical compound C1=C(OC)C(OC(=O)C=CC=CC=CC=CC=CCCCCCCCCC)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=C(OC(=O)C=CC=CC=CC=CC=CCCCCCCCCC)C(OC)=C1 UAZHWIXFOFAWEN-UHFFFAOYSA-N 0.000 description 6
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- DKBWSRSXMZEMRO-UHFFFAOYSA-N [2-hydroxy-4-[7-(3-hydroxy-4-icosa-2,4,6,8,10-pentaenoyloxyphenyl)-3,5-dioxohepta-1,6-dienyl]phenyl] docosa-2,4,6,8,10,12-hexaenoate Chemical compound C1=C(O)C(OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=C(OC(=O)C=CC=CC=CC=CC=CCCCCCCCCC)C(O)=C1 DKBWSRSXMZEMRO-UHFFFAOYSA-N 0.000 description 1
- INQBRYGAQFGNPF-UHFFFAOYSA-N [4-[7-(3,4-dihydroxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-hydroxyphenyl] icosa-2,4,6,8,10-pentaenoate Chemical compound C1=C(O)C(OC(=O)C=CC=CC=CC=CC=CCCCCCCCCC)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=C(O)C(O)=C1 INQBRYGAQFGNPF-UHFFFAOYSA-N 0.000 description 1
- XXUKDLQSJSXPNT-UHFFFAOYSA-N [4-[7-(4-docosa-2,4,6,8,10,12-hexaenoyloxy-3-hydroxyphenyl)-3,5-dioxohepta-1,6-dienyl]-2-hydroxyphenyl] docosa-2,4,6,8,10,12-hexaenoate Chemical compound C1=C(O)C(OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=C(OC(=O)C=CC=CC=CC=CC=CC=CCCCCCCCCC)C(O)=C1 XXUKDLQSJSXPNT-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JYTVKRNTTALBBZ-UHFFFAOYSA-N bis demethoxycurcumin Natural products C1=CC(O)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=CC(O)=C1 JYTVKRNTTALBBZ-UHFFFAOYSA-N 0.000 description 1
- PREBVFJICNPEKM-YDWXAUTNSA-N bisdemethoxycurcumin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)CC(=O)\C=C\C1=CC=C(O)C=C1 PREBVFJICNPEKM-YDWXAUTNSA-N 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- NMRUIRRIQNAQEB-UHFFFAOYSA-N demethoxycurcumin Natural products OC(=CC(C=CC1=CC(=C(C=C1)O)OC)=O)C=CC1=CC=C(C=C1)O NMRUIRRIQNAQEB-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- YXAKCQIIROBKOP-UHFFFAOYSA-N di-p-hydroxycinnamoylmethane Natural products C=1C=C(O)C=CC=1C=CC(=O)C=C(O)C=CC1=CC=C(O)C=C1 YXAKCQIIROBKOP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- VEKIZRLWPXYFMW-UHFFFAOYSA-N hepta-1,6-diene-3,5-dione Chemical compound C=CC(=O)CC(=O)C=C VEKIZRLWPXYFMW-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003960 inflammatory cascade Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- SRPSOCQMBCNWFR-UHFFFAOYSA-N iodous acid Chemical compound OI=O SRPSOCQMBCNWFR-UHFFFAOYSA-N 0.000 description 1
- 230000003859 lipid peroxidation Effects 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 230000008789 oxidative DNA damage Effects 0.000 description 1
- UEPVWRDHSPMIAZ-UHFFFAOYSA-N p-hydroxycinnamoyl feruloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(O)=CC(=O)C=CC=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 208000007153 proteostasis deficiencies Diseases 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Psychiatry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1641/CHE/2008 | 2008-07-07 | ||
| IN1641CH2008 | 2008-07-07 | ||
| PCT/IN2009/000382 WO2010004579A2 (en) | 2008-07-07 | 2009-07-06 | Orally active curcuminoid compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009269530A1 true AU2009269530A1 (en) | 2010-01-14 |
Family
ID=41507515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009269530A Abandoned AU2009269530A1 (en) | 2008-07-07 | 2009-07-06 | Orally active curcuminoid compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8680143B2 (https=) |
| EP (1) | EP2294049A4 (https=) |
| JP (1) | JP2011527340A (https=) |
| CN (1) | CN102131765A (https=) |
| AU (1) | AU2009269530A1 (https=) |
| WO (1) | WO2010004579A2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015186144A2 (en) * | 2014-06-07 | 2015-12-10 | Laila Pharmaceuticals Pvt. Ltd. | Method of inhibition of beta-secretase by using bis-o-demethylcurcumin for the prevention, management and treatment of neurodegenerative diseases |
| US10085951B2 (en) | 2014-12-11 | 2018-10-02 | Designs For Health, Inc. | Curcuminoid formulations and related methods of treatment |
| US11135185B2 (en) | 2018-03-23 | 2021-10-05 | Merry Life Biomedical Company, Ltd. | Uses of curcumin derivative |
| CN112315953B (zh) * | 2020-11-06 | 2023-03-07 | 中国海洋大学 | 一种姜黄素酯在改善急性肾损伤制品中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004031122A1 (de) * | 2002-10-01 | 2004-04-15 | Dr. André Rieks - Labor Für Enzymtechnologie Gmbh | Neue curcumin/tetrahydrocurcumin-derivate für den einsatz in kosmetika, pharmazeutika und bei der ernährung |
| EP1876908A1 (en) * | 2005-05-03 | 2008-01-16 | DSMIP Assets B.V. | Aryl derivatives of curcumin, demethoxycurcumin, bisdemethoxycurcumin or curcuminisoxazolide and their use as animal feed additives |
| WO2007103435A2 (en) * | 2006-03-06 | 2007-09-13 | The Regents Of The University Of California | Bioavailable curcuminoid formulations for treating alzheimer's disease and other age-related disorders |
| EP1999097B1 (en) * | 2006-03-29 | 2011-12-21 | DSM IP Assets B.V. | Curcumin synthesis |
| CA2665916C (en) * | 2006-10-12 | 2015-12-08 | The Research Foundation Of The City University Of New York | Novel curcumin and tetrahydrocurcumin derivatives |
-
2009
- 2009-07-06 AU AU2009269530A patent/AU2009269530A1/en not_active Abandoned
- 2009-07-06 WO PCT/IN2009/000382 patent/WO2010004579A2/en not_active Ceased
- 2009-07-06 US US13/002,588 patent/US8680143B2/en not_active Expired - Fee Related
- 2009-07-06 EP EP09794105A patent/EP2294049A4/en not_active Withdrawn
- 2009-07-06 JP JP2011517314A patent/JP2011527340A/ja active Pending
- 2009-07-06 CN CN2009801136580A patent/CN102131765A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010004579A3 (en) | 2011-01-27 |
| US8680143B2 (en) | 2014-03-25 |
| EP2294049A4 (en) | 2011-06-22 |
| EP2294049A2 (en) | 2011-03-16 |
| US20110112190A1 (en) | 2011-05-12 |
| CN102131765A (zh) | 2011-07-20 |
| WO2010004579A2 (en) | 2010-01-14 |
| JP2011527340A (ja) | 2011-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |