CA2766834C - Compositions containing berberine or analogs thereof for treating rosacea or red face related skin disorders - Google Patents
Compositions containing berberine or analogs thereof for treating rosacea or red face related skin disorders Download PDFInfo
- Publication number
- CA2766834C CA2766834C CA2766834A CA2766834A CA2766834C CA 2766834 C CA2766834 C CA 2766834C CA 2766834 A CA2766834 A CA 2766834A CA 2766834 A CA2766834 A CA 2766834A CA 2766834 C CA2766834 C CA 2766834C
- Authority
- CA
- Canada
- Prior art keywords
- berberine
- rosacea
- dermatitis
- related skin
- red face
- 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.)
- Expired - Fee Related
Links
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 title claims abstract description 94
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 title claims abstract description 94
- 229940093265 berberine Drugs 0.000 title claims abstract description 94
- 201000004700 rosacea Diseases 0.000 title claims abstract description 82
- 241001303601 Rosacea Species 0.000 title claims abstract description 52
- 208000017520 skin disease Diseases 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 title description 26
- 230000000699 topical effect Effects 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 37
- PTPHDVKWAYIFRX-UHFFFAOYSA-N Palmatine Natural products C1C2=C(OC)C(OC)=CC=C2C=C2N1CCC1=C2C=C(OC)C(OC)=C1 PTPHDVKWAYIFRX-UHFFFAOYSA-N 0.000 claims abstract description 20
- QUCQEUCGKKTEBI-UHFFFAOYSA-N palmatine Chemical compound COC1=CC=C2C=C(C3=C(C=C(C(=C3)OC)OC)CC3)[N+]3=CC2=C1OC QUCQEUCGKKTEBI-UHFFFAOYSA-N 0.000 claims abstract description 20
- XDVZNDLANFJOQR-UHFFFAOYSA-N Coptisine Natural products O=Cc1c2OCOc2ccc1C=C3/NCCc4cc5OCOc5cc34 XDVZNDLANFJOQR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 12
- 150000003431 steroids Chemical class 0.000 claims abstract description 11
- 206010015150 Erythema Diseases 0.000 claims description 34
- 206010000496 acne Diseases 0.000 claims description 13
- 150000003836 berberines Chemical class 0.000 claims description 12
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- LUXPUVKJHVUJAV-UHFFFAOYSA-M coptisine, chloride Chemical compound [Cl-].C1=C2C=C(C3=C(C=C4OCOC4=C3)CC3)[N+]3=CC2=C2OCOC2=C1 LUXPUVKJHVUJAV-UHFFFAOYSA-M 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- MXTLAHSTUOXGQF-UHFFFAOYSA-O Jatrorrhizine Chemical group COC1=CC=C2C=C3C(C=C(C(=C4)O)OC)=C4CC[N+]3=CC2=C1OC MXTLAHSTUOXGQF-UHFFFAOYSA-O 0.000 claims description 10
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- GYFSYEVKFOOLFZ-UHFFFAOYSA-N Berberrubine Chemical compound [Cl-].C1=C2CC[N+]3=CC4=C(O)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 GYFSYEVKFOOLFZ-UHFFFAOYSA-N 0.000 claims description 5
- QBUIDYLGKMWNEA-UHFFFAOYSA-O Palmatrubine Natural products COC1=C(OC)C=C2CC[N+]3=CC4=C(O)C(OC)=CC=C4C=C3C2=C1 QBUIDYLGKMWNEA-UHFFFAOYSA-O 0.000 claims description 5
- GLYPKDKODVRYGP-UHFFFAOYSA-O berberrubine Natural products C1=C2CC[N+]3=CC4=C(O)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 GLYPKDKODVRYGP-UHFFFAOYSA-O 0.000 claims description 5
- GLYPKDKODVRYGP-UHFFFAOYSA-N burberrubine Natural products C12=CC=3OCOC=3C=C2CCN2C1=CC1=CC=C(OC)C(=O)C1=C2 GLYPKDKODVRYGP-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
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- HFEKMQAJWLENMF-UHFFFAOYSA-M chembl2270070 Chemical compound [Cl-].C12=CC=3OCOC=3C=C2CC[N+]2=C1C=C1C=CC(OC)=C(OCC)C1=C2 HFEKMQAJWLENMF-UHFFFAOYSA-M 0.000 claims 3
- PSXYWKIWNLYYQJ-UHFFFAOYSA-M chembl2270071 Chemical compound [Cl-].C12=CC=3OCOC=3C=C2CC[N+]2=C1C(CC)=C1C=CC(OC)=C(OCC)C1=C2 PSXYWKIWNLYYQJ-UHFFFAOYSA-M 0.000 claims 3
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- XYHOBCMEDLZUMP-UHFFFAOYSA-N coptisine Chemical compound C1=C2C=C(C3=C(C=C4OCOC4=C3)CC3)[N+]3=CC2=C2OCOC2=C1 XYHOBCMEDLZUMP-UHFFFAOYSA-N 0.000 abstract 1
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| US61/221,725 | 2009-06-30 | ||
| PCT/CN2010/000983 WO2011000218A1 (en) | 2009-06-30 | 2010-06-30 | Compositions containing berberine or analogs thereof for treating rosacea or red face related skin disorders |
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| CA2766834A1 CA2766834A1 (en) | 2011-01-06 |
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| CA2766834A Expired - Fee Related CA2766834C (en) | 2009-06-30 | 2010-06-30 | Compositions containing berberine or analogs thereof for treating rosacea or red face related skin disorders |
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| US (1) | US9486402B2 (enExample) |
| EP (1) | EP2448577B1 (enExample) |
| JP (2) | JP6159084B2 (enExample) |
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| US20160263092A1 (en) | 2013-12-19 | 2016-09-15 | Twi Biotechnology, Inc. | Therapeutic uses of berberine formulations |
| TW201538156A (zh) * | 2013-12-19 | 2015-10-16 | Twi Biotechnology Inc | 小蘗鹼配方及其用途 |
| AU2016282800A1 (en) * | 2015-06-24 | 2018-02-01 | Twi Biotechnology, Inc. | Therapeutic uses of berberine formulations |
| US10293005B2 (en) | 2016-04-19 | 2019-05-21 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Use of gram negative species to treat atopic dermatitis |
| EP3445330B1 (en) | 2016-04-19 | 2022-07-06 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Use of gram negative species to treat atopic dermatitis |
| EP3570835B1 (en) * | 2017-01-19 | 2023-08-09 | TWI Biotechnology, Inc. | Diacerein for preventing or treating immunoinflammatory dermal disorders |
| EP3398448A1 (en) | 2017-05-05 | 2018-11-07 | Vall Garraf, S.L. | Fattening additive for animal nutritional composition |
| CN111601617A (zh) | 2017-12-13 | 2020-08-28 | 上海岸阔医药科技有限公司 | 一种用于预防或治疗与egfr 被抑制相关疾病的方法 |
| JP7520366B2 (ja) | 2018-04-16 | 2024-07-23 | オンクオリティー ファーマシューティカルズ チャイナ リミテッド | 腫瘍療法の副作用の予防または治療方法 |
| EP3784260A4 (en) * | 2018-04-18 | 2022-03-09 | Forte Subsidiary, Inc. | Compositions for the treatment of skin conditions |
| CN108329310A (zh) * | 2018-05-07 | 2018-07-27 | 深圳市迪克曼科技开发有限公司 | 黄藤素的制备方法 |
| KR20210013080A (ko) | 2018-05-11 | 2021-02-03 | 포르테 서브시디어리, 인크. | 피부 병태의 치료를 위한 조성물 |
| CN110882246B (zh) * | 2018-09-08 | 2022-12-23 | 西南大学 | 不同生物活性的黄连生物碱的提取方法及应用 |
| JP2020045338A (ja) * | 2018-09-12 | 2020-03-26 | 大正製薬株式会社 | 外用組成物 |
| IL281761B2 (en) | 2018-09-25 | 2025-09-01 | Ponce De Leon Health Designated Activity Company | Process for preparing calcium alpha-ketoglutarate |
| JP6535146B1 (ja) * | 2019-03-08 | 2019-06-26 | 佐藤製薬株式会社 | 皮膚バリア機能改善剤 |
| RU2697854C1 (ru) * | 2019-05-14 | 2019-08-21 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Сибирский государственный медицинский университет" Министерства здравоохранения Российской Федерации | Способ комбинированной наружной терапии эритематозно-папулезной розацеа |
| CN113440613A (zh) * | 2020-03-26 | 2021-09-28 | 轶诺(浙江)药业有限公司 | 小檗碱类似物与jak抑制剂在胃肠道炎症性疾病治疗中的用途 |
| CN116370469A (zh) * | 2023-04-27 | 2023-07-04 | 常州大学 | 四氢小檗碱类化合物对trpv3的抑制应用 |
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| JPS6150920A (ja) * | 1984-08-20 | 1986-03-13 | Ichimaru Fuarukosu Kk | 黄柏抽出エキス含有液の製造法 |
| JPS63179812A (ja) * | 1987-01-22 | 1988-07-23 | Shiseido Co Ltd | 皮膚外用剤 |
| JP2609564B2 (ja) * | 1991-05-31 | 1997-05-14 | 政夫 斎藤 | アレルギー性皮膚炎用クリーム及びその製造方法 |
| CN1085600A (zh) * | 1993-07-07 | 1994-04-20 | 南宁市迪生新技术研究所 | 防治性病、传染病的杀菌保健香皂和浴液 |
| CN1182788A (zh) * | 1997-02-03 | 1998-05-27 | 熊光明 | 一种防治性病传染病的保健洗涤用品 |
| US6482839B1 (en) | 1997-06-02 | 2002-11-19 | Cellegy Pharmaceuticals, Inc. | Pyridine-thiols for treatment of a follicular dermatosis |
| US6440465B1 (en) * | 2000-05-01 | 2002-08-27 | Bioderm, Inc. | Topical composition for the treatment of psoriasis and related skin disorders |
| JP2001335485A (ja) * | 2000-05-31 | 2001-12-04 | Pola Chem Ind Inc | メラノサイトのデンドライトの伸長抑制剤及びそれを含有する化粧料 |
| KR20030082200A (ko) * | 2002-04-17 | 2003-10-22 | 주식회사 엘지생활건강 | 베르베린을 함유하는 아토피성 피부염 예방 및 완화용조성물 |
| US20040146539A1 (en) | 2003-01-24 | 2004-07-29 | Gupta Shyam K. | Topical Nutraceutical Compositions with Selective Body Slimming and Tone Firming Antiaging Benefits |
| WO2004093876A2 (en) * | 2003-04-03 | 2004-11-04 | The Board Of Trustees Of The University Of Illinois | Composition containing berberine or a derivative thereof and an antimicrobial agent or an antibiotic agent, and their use for treating oral pathogens and other disorders |
| US7205006B2 (en) * | 2003-09-25 | 2007-04-17 | Prime Pharmaceutical Corporation | Mahonia aquifolium extract, extraction process and pharmaceutical composition containing the same |
| KR101045658B1 (ko) | 2003-11-17 | 2011-07-01 | 쎄데르마 | 테트라펩티드 및 트리펩티드 혼합물을 포함하는 조성물 |
| US20050158404A1 (en) | 2003-11-18 | 2005-07-21 | Goodless Dean R. | Composition and method for treatment of acne |
| EP1591125A1 (de) * | 2004-04-19 | 2005-11-02 | Universitätsklinikum Freiburg | Pharmazeutische Zusammensetzung enthaltend Extrakte aus Flechten und Johanniskraut |
| US20060286054A1 (en) * | 2005-06-15 | 2006-12-21 | Apollo Pharmaceutical, Inc. | Pharmaceutical compositions for the treatment of psoriasis |
| CN100441183C (zh) * | 2005-08-29 | 2008-12-10 | 中国医学科学院皮肤病研究所 | 盐酸13-己基小檗碱和盐酸13-己基巴马汀制备治疗湿疹、皮炎和银屑病的药物用途 |
| DE202010004750U1 (de) * | 2010-04-09 | 2011-10-11 | Biofrontera Bioscience Gmbh | Pharmazeutische oder/und kosmetische Zusammensetzung zur Behandlung der Haut |
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| JP6159084B2 (ja) | 2017-07-05 |
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| JP2012531448A (ja) | 2012-12-10 |
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| KR101699572B1 (ko) | 2017-01-24 |
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| NZ597645A (en) | 2014-03-28 |
| CN102481290A (zh) | 2012-05-30 |
| HK1224206A1 (zh) | 2017-08-18 |
| IL217264A (en) | 2017-01-31 |
| KR20170010442A (ko) | 2017-01-31 |
| IL217264A0 (en) | 2012-02-29 |
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| EP2448577B1 (en) | 2016-09-14 |
| RU2671492C2 (ru) | 2018-11-01 |
| AU2010268647A1 (en) | 2012-02-09 |
| KR20120047240A (ko) | 2012-05-11 |
| RU2012102898A (ru) | 2013-08-10 |
| JP2017082019A (ja) | 2017-05-18 |
| BRPI1012128A2 (pt) | 2016-03-29 |
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