JP2005505497A5 - - Google Patents
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- Publication number
- JP2005505497A5 JP2005505497A5 JP2002574897A JP2002574897A JP2005505497A5 JP 2005505497 A5 JP2005505497 A5 JP 2005505497A5 JP 2002574897 A JP2002574897 A JP 2002574897A JP 2002574897 A JP2002574897 A JP 2002574897A JP 2005505497 A5 JP2005505497 A5 JP 2005505497A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- proanthocyanidins
- epicatechin
- group
- amyloidosis
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 42
- 239000008194 pharmaceutical composition Substances 0.000 claims 34
- 229920002770 condensed tannin Polymers 0.000 claims 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 22
- 206010002022 amyloidosis Diseases 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 15
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims 12
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 claims 12
- 229920002414 procyanidin Polymers 0.000 claims 12
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 claims 11
- 235000012734 epicatechin Nutrition 0.000 claims 11
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 claims 11
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 claims 10
- 241000196324 Embryophyta Species 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 239000013638 trimer Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims 8
- 235000005487 catechin Nutrition 0.000 claims 8
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 claims 7
- 229920001991 Proanthocyanidin Polymers 0.000 claims 7
- 239000000463 material Substances 0.000 claims 7
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims 6
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 claims 6
- -1 2,3-dihydroxybenzoyl Chemical group 0.000 claims 6
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 claims 6
- 229950001002 cianidanol Drugs 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 5
- 239000000741 silica gel Substances 0.000 claims 5
- 229910002027 silica gel Inorganic materials 0.000 claims 5
- 102000003802 alpha-Synuclein Human genes 0.000 claims 4
- 108090000185 alpha-Synuclein Proteins 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 150000001765 catechin Chemical class 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims 4
- 229920000429 procyanidin dimer Polymers 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000000539 dimer Substances 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 230000001225 therapeutic effect Effects 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims 2
- 229920001505 Procyanidin B4 Polymers 0.000 claims 2
- 229920001554 Procyanidin C1 Polymers 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 125000004403 catechin group Chemical group 0.000 claims 2
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 claims 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 238000004007 reversed phase HPLC Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 claims 1
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 claims 1
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims 1
- PBZMVAYHJDFHIR-UHFFFAOYSA-N 2-phenyl-3,4-dihydrochromene-2,3-diol Chemical class OC1CC2=CC=CC=C2OC1(O)C1=CC=CC=C1 PBZMVAYHJDFHIR-UHFFFAOYSA-N 0.000 claims 1
- 208000023769 AA amyloidosis Diseases 0.000 claims 1
- 208000023761 AL amyloidosis Diseases 0.000 claims 1
- 206010007509 Cardiac amyloidosis Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 claims 1
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 1
- 208000010201 Exanthema Diseases 0.000 claims 1
- 208000034846 Familial Amyloid Neuropathies Diseases 0.000 claims 1
- CITFYDYEWQIEPX-UHFFFAOYSA-N Flavanol Natural products O1C2=CC(OCC=C(C)C)=CC(O)=C2C(=O)C(O)C1C1=CC=C(O)C=C1 CITFYDYEWQIEPX-UHFFFAOYSA-N 0.000 claims 1
- 206010019889 Hereditary neuropathic amyloidosis Diseases 0.000 claims 1
- 208000005531 Immunoglobulin Light-chain Amyloidosis Diseases 0.000 claims 1
- 208000009829 Lewy Body Disease Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000001089 Multiple system atrophy Diseases 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 102000029797 Prion Human genes 0.000 claims 1
- 108091000054 Prion Proteins 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 241000400007 Uncarina Species 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 229930014669 anthocyanidin Natural products 0.000 claims 1
- 235000008758 anthocyanidins Nutrition 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000000120 cytopathologic effect Effects 0.000 claims 1
- 210000004262 dental pulp cavity Anatomy 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000011523 endocrine gland cancer Diseases 0.000 claims 1
- 150000002116 epicatechin Chemical class 0.000 claims 1
- 201000005884 exanthem Diseases 0.000 claims 1
- 150000002206 flavan-3-ols Chemical class 0.000 claims 1
- 235000011987 flavanols Nutrition 0.000 claims 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims 1
- 150000002216 flavonol derivatives Chemical class 0.000 claims 1
- 235000011957 flavonols Nutrition 0.000 claims 1
- NWKFECICNXDNOQ-UHFFFAOYSA-N flavylium Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=[O+]1 NWKFECICNXDNOQ-UHFFFAOYSA-N 0.000 claims 1
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 claims 1
- 208000035474 group of disease Diseases 0.000 claims 1
- 238000001631 haemodialysis Methods 0.000 claims 1
- 230000000322 hemodialysis Effects 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 239000007928 intraperitoneal injection Substances 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 230000036210 malignancy Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 206010037844 rash Diseases 0.000 claims 1
- 208000008864 scrapie Diseases 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 238000010254 subcutaneous injection Methods 0.000 claims 1
- 239000007929 subcutaneous injection Substances 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 201000007905 transthyretin amyloidosis Diseases 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27686601P | 2001-03-15 | 2001-03-15 | |
| US09/938,987 US6607758B2 (en) | 1997-05-15 | 2001-08-24 | Methods for inhibiting and reducing amyloid fibril formation associated with Alzheimer's Disease and other amyloidoses |
| US10/053,625 US6929808B2 (en) | 2000-11-03 | 2001-11-02 | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from Uncaria tomentosa and related plants |
| PCT/US2001/051131 WO2002042429A2 (en) | 2000-11-03 | 2001-11-02 | Methods of isolating amyloid-inhibiting compounds and use of compounds isolated from uncaria tomentosa and related plants |
| US33872101P | 2001-12-04 | 2001-12-04 | |
| US33903301P | 2001-12-10 | 2001-12-10 | |
| US33896901P | 2001-12-10 | 2001-12-10 | |
| PCT/US2002/004764 WO2002076381A2 (en) | 2001-03-15 | 2002-02-15 | Proanthocyanidins for the treatment of amyloid and alpha-synuclein diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005505497A JP2005505497A (ja) | 2005-02-24 |
| JP2005505497A5 true JP2005505497A5 (enExample) | 2005-12-22 |
| JP4380991B2 JP4380991B2 (ja) | 2009-12-09 |
Family
ID=56290250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002574897A Expired - Fee Related JP4380991B2 (ja) | 2001-03-15 | 2002-02-15 | アミロイド及びαシニュクライン疾患の治療のためのプロアントシアニジン |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1377287A4 (enExample) |
| JP (1) | JP4380991B2 (enExample) |
| AU (1) | AU2002250117B2 (enExample) |
| CA (1) | CA2441099C (enExample) |
| NZ (1) | NZ528322A (enExample) |
| WO (1) | WO2002076381A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070208087A1 (en) | 2001-11-02 | 2007-09-06 | Sanders Virginia J | Compounds, compositions and methods for the treatment of inflammatory diseases |
| US7514107B2 (en) | 2002-03-21 | 2009-04-07 | Mars, Incorporated | Treatment of diseases involving defective gap junctional communication |
| PT1511710E (pt) * | 2002-05-31 | 2014-02-26 | Proteotech Inc | Compostos, composições e métodos para o tratamento de doenças da amiloide e sinucleínopatias tais como doença de alzheimer, diabetes do tipo 2, e doença de parkinson |
| CA2499549C (en) * | 2002-10-11 | 2012-01-24 | Proteotech, Inc. | Isolation, purification and synthesis of procyanidin b2 and uses thereof |
| JP2006232670A (ja) * | 2003-05-20 | 2006-09-07 | Ajinomoto Co Inc | 神経障害用薬剤 |
| WO2005082351A1 (ja) * | 2004-03-02 | 2005-09-09 | Eisai R & D Management Co., Ltd. | 神経変性疾患治療剤 |
| DK2004155T3 (en) * | 2006-03-29 | 2018-04-30 | Wista Lab Ltd | PROTEIN AGGREGATION INHIBITORS |
| WO2009104556A1 (ja) * | 2008-02-19 | 2009-08-27 | 株式会社岐阜セラツク製造所 | 組成物 |
| JP5738755B2 (ja) * | 2008-05-09 | 2015-06-24 | アイカーン スクール オブ メディシン アット マウント シナイ | 神経変性疾患を予防および治療するための方法 |
| US20140179774A1 (en) * | 2012-12-26 | 2014-06-26 | Industrial Technology Research Institute | Methods for inhibition of shc-1/p66 to combat aging-related diseases |
| CN107530385A (zh) | 2015-05-11 | 2018-01-02 | 株式会社明治 | 用于促进脑源性神经营养因子产生的组合物 |
| KR102441381B1 (ko) * | 2016-07-18 | 2022-09-07 | (주)아모레퍼시픽 | 3-O-갈로일-3,3',5,5',7-펜타하이드록시플라반(3-O-galloyl-3,3',5,5',7- pentahydroxyflavan)을 포함하는 인지 기능 개선용 조성물 |
| WO2021193703A1 (ja) * | 2020-03-24 | 2021-09-30 | 学校法人 芝浦工業大学 | 中枢神経賦活組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4698360B1 (en) * | 1985-04-09 | 1997-11-04 | D Investigations Pharmacologiq | Plant extract with a proanthocyanidins content as therapeutic agent having radical scavenger effect and use thereof |
| US6346280B1 (en) * | 1997-05-15 | 2002-02-12 | University Of Washington | Composition and methods for inhibiting the formation of brain amyloid deposits |
| WO1998051302A1 (en) * | 1997-05-15 | 1998-11-19 | University Of Washington | Composition and methods for treating alzheimer's disease and other amyloidoses |
| US5922756A (en) * | 1998-02-14 | 1999-07-13 | Chan; Marion Man-Ying | Method of inhibiting nitric oxide synthase |
| CA2322860C (en) * | 1998-03-12 | 2010-10-19 | Mars, Incorporated | Products containing polyphenol(s) and l-arginine to stimulate nitric oxide production |
| AU3886200A (en) * | 1999-03-15 | 2000-10-16 | Proteotech, Inc. | Methods of treating alzheimer's disease and other amyloidoses using hypericum perforatum and derivatives thereof |
| EP1246632A4 (en) * | 1999-12-30 | 2004-08-18 | Proteotech Inc | CATECHINE AND GREEN TEA EXTRACT FOR TREATING AMYLOIDOSES IN GENERAL OR. AT ALZHEIMER |
-
2002
- 2002-02-15 AU AU2002250117A patent/AU2002250117B2/en not_active Ceased
- 2002-02-15 EP EP02719009A patent/EP1377287A4/en not_active Withdrawn
- 2002-02-15 CA CA2441099A patent/CA2441099C/en not_active Expired - Fee Related
- 2002-02-15 WO PCT/US2002/004764 patent/WO2002076381A2/en not_active Ceased
- 2002-02-15 NZ NZ528322A patent/NZ528322A/en not_active IP Right Cessation
- 2002-02-15 JP JP2002574897A patent/JP4380991B2/ja not_active Expired - Fee Related
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