JP2012517450A5 - - Google Patents
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- Publication number
- JP2012517450A5 JP2012517450A5 JP2011549394A JP2011549394A JP2012517450A5 JP 2012517450 A5 JP2012517450 A5 JP 2012517450A5 JP 2011549394 A JP2011549394 A JP 2011549394A JP 2011549394 A JP2011549394 A JP 2011549394A JP 2012517450 A5 JP2012517450 A5 JP 2012517450A5
- Authority
- JP
- Japan
- Prior art keywords
- ingenol
- pharmaceutical composition
- optionally substituted
- skin
- compound
- 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
- VEBVPUXQAPLADL-UHFFFAOYSA-N Ingenol Natural products C1=C(CO)C(O)C2(O)C(O)C(C)=CC32C(C)CC2C(C)(C)C2C1C3=O VEBVPUXQAPLADL-UHFFFAOYSA-N 0.000 claims description 23
- -1 ingenol compound Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- VDJHFHXMUKFKET-UHFFFAOYSA-N Ingenol mebutate Natural products CC1CC2C(C)(C)C2C2C=C(CO)C(O)C3(O)C(OC(=O)C(C)=CC)C(C)=CC31C2=O VDJHFHXMUKFKET-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- VDJHFHXMUKFKET-WDUFCVPESA-N ingenol mebutate Chemical compound C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(CO)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O VDJHFHXMUKFKET-WDUFCVPESA-N 0.000 claims description 6
- 229960002993 ingenol mebutate Drugs 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 claims description 5
- 229940099552 hyaluronan Drugs 0.000 claims description 5
- 229920002674 hyaluronan Polymers 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UQOWJJGOQJONCI-UHFFFAOYSA-N 20-deoxyingenol-3-angelate Natural products CC1CC2C(C)(C)C2C2C=C(C)C(O)C3(O)C(OC(=O)C(C)=CC)C(C)=CC31C2=O UQOWJJGOQJONCI-UHFFFAOYSA-N 0.000 claims description 3
- UQOWJJGOQJONCI-MZRDIQIISA-N C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(C)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O Chemical compound C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(C)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O UQOWJJGOQJONCI-MZRDIQIISA-N 0.000 claims description 3
- ZYCAGKYWXRKLSN-KLKWOBOISA-N C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(COC(C)=O)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O Chemical compound C[C@@H]1C[C@H]2C(C)(C)[C@H]2[C@@H]2C=C(COC(C)=O)[C@@H](O)[C@]3(O)[C@@H](OC(=O)C(\C)=C/C)C(C)=C[C@]31C2=O ZYCAGKYWXRKLSN-KLKWOBOISA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005601 angeloyl group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 230000037303 wrinkles Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 claims 1
- VEBVPUXQAPLADL-POYOOMFHSA-N ingenol Chemical class C1=C(CO)[C@@H](O)[C@]2(O)[C@@H](O)C(C)=C[C@]32[C@H](C)C[C@H]2C(C)(C)[C@H]2[C@H]1C3=O VEBVPUXQAPLADL-POYOOMFHSA-N 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15259909P | 2009-02-13 | 2009-02-13 | |
| US61/152,599 | 2009-02-13 | ||
| PCT/AU2010/000152 WO2010091472A1 (en) | 2009-02-13 | 2010-02-12 | Skin treatment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012517450A JP2012517450A (ja) | 2012-08-02 |
| JP2012517450A5 true JP2012517450A5 (https=) | 2013-04-04 |
| JP5638008B2 JP5638008B2 (ja) | 2014-12-10 |
Family
ID=42561329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011549394A Expired - Fee Related JP5638008B2 (ja) | 2009-02-13 | 2010-02-12 | 皮膚治療方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10143638B2 (https=) |
| EP (1) | EP2395993B1 (https=) |
| JP (1) | JP5638008B2 (https=) |
| CN (1) | CN102316866A (https=) |
| AU (1) | AU2010213362B2 (https=) |
| CA (1) | CA2752389C (https=) |
| DK (1) | DK2395993T3 (https=) |
| ES (1) | ES2633755T3 (https=) |
| IL (1) | IL214133A (https=) |
| NZ (1) | NZ594184A (https=) |
| PL (1) | PL2395993T3 (https=) |
| PT (1) | PT2395993T (https=) |
| RU (1) | RU2491050C2 (https=) |
| WO (1) | WO2010091472A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9402823B2 (en) | 2010-12-17 | 2016-08-02 | Leo Laboratories Limited | Ingenols for treating seborrheic keratosis |
| CN103402969A (zh) * | 2010-12-22 | 2013-11-20 | 利奥实验室有限公司 | 3-酰基-巨大戟二萜醇ii |
| JP2014507396A (ja) * | 2010-12-22 | 2014-03-27 | レオ・ラボラトリーズ・リミテッド | イノゲノール−３−アシラートｉ |
| WO2012176015A1 (en) | 2011-06-24 | 2012-12-27 | Leo Pharma A/S | Methods for treating uv-damaged skin and scc tumors and for removing tattoos with topical ingenol mebutate |
| US20140350101A1 (en) * | 2011-12-12 | 2014-11-27 | Leo Laboratories Limited | Gel compositions |
| EP2790670A1 (en) * | 2011-12-12 | 2014-10-22 | Leo Laboratories Limited | Gel compositions |
| US20150366789A1 (en) * | 2013-03-13 | 2015-12-24 | Avon Place, Inc. | Glochidium wallichianum extracts and methods of use |
| US9526714B2 (en) | 2014-03-24 | 2016-12-27 | Leo Laboratories Limited | Method for treating skin lesions with ingenol mebutate |
| AU2014100280B4 (en) * | 2014-03-24 | 2015-01-15 | Leo Pharma A/S | A method of treating skin lesions |
| BR112018074202B1 (pt) * | 2016-05-24 | 2022-08-02 | Natura Cosméticos S.A | Composição cosmética antissinais, kit de composições e método para tratamento cosmético da pele |
| JP7557192B2 (ja) | 2020-08-19 | 2024-09-27 | 日本メナード化粧品株式会社 | 皮膚外用剤及び内用剤 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08176004A (ja) * | 1994-12-21 | 1996-07-09 | Lion Corp | 生体老化防止剤及び皮膚用組成物 |
| JPH0987136A (ja) * | 1995-07-13 | 1997-03-31 | Shiseido Co Ltd | 皮膚外用剤 |
| AUPO864097A0 (en) | 1997-08-19 | 1997-09-11 | Peplin Pty Ltd | Anti-cancer compounds |
| AU750624B2 (en) * | 1997-08-19 | 2002-07-25 | Leo Laboratories Limited | Anti-cancer compounds-I |
| KR20010057776A (ko) * | 1999-12-23 | 2001-07-05 | 성재갑 | 피부미백제 |
| JP4880816B2 (ja) | 2000-12-15 | 2012-02-22 | 株式会社ヤクルト本社 | 皮膚老化防止剤 |
| JP3935360B2 (ja) * | 2002-01-22 | 2007-06-20 | 丸善製薬株式会社 | ヒアルロン酸産生促進剤並びに皮膚化粧料及び美容用飲食品 |
| RU2229293C1 (ru) * | 2003-04-24 | 2004-05-27 | Хазанов Вениамин Абрамович | Лечебно-профилактическое средство для использования в геронтологической практике |
| US20070224150A1 (en) * | 2005-03-24 | 2007-09-27 | Yongji Chung | Growth factor for hair and skin treatment |
| JP2007084448A (ja) * | 2005-09-20 | 2007-04-05 | Shiseido Co Ltd | ヒアルロン酸産生促進剤および皮膚外用剤 |
| BRPI0504797B1 (pt) | 2005-10-27 | 2020-02-04 | Pele Nova Biotecnologia S.A. | formulação tópica, método de tratamento cosmético para rejuvenescimento da pele, método de tratamento cosmético e uso de uma formulação |
| KR20080077625A (ko) * | 2005-11-25 | 2008-08-25 | 페플린 리서치 피티이 리미티드 | 상처 치유 방법 |
| SI2152261T1 (sl) | 2007-04-30 | 2016-05-31 | Leo Laboratories Limited | Zdravljenje viralno induciranih lezij |
| EP2558435B1 (en) * | 2010-04-16 | 2017-06-07 | Leo Pharma A/S | Orthorhombic crystalline ingenol mebutate |
-
2010
- 2010-02-12 JP JP2011549394A patent/JP5638008B2/ja not_active Expired - Fee Related
- 2010-02-12 CA CA2752389A patent/CA2752389C/en not_active Expired - Fee Related
- 2010-02-12 PT PT107408478T patent/PT2395993T/pt unknown
- 2010-02-12 US US13/201,331 patent/US10143638B2/en not_active Expired - Fee Related
- 2010-02-12 WO PCT/AU2010/000152 patent/WO2010091472A1/en not_active Ceased
- 2010-02-12 PL PL10740847T patent/PL2395993T3/pl unknown
- 2010-02-12 RU RU2011137530/15A patent/RU2491050C2/ru not_active IP Right Cessation
- 2010-02-12 EP EP10740847.8A patent/EP2395993B1/en not_active Not-in-force
- 2010-02-12 NZ NZ594184A patent/NZ594184A/en not_active IP Right Cessation
- 2010-02-12 ES ES10740847.8T patent/ES2633755T3/es active Active
- 2010-02-12 CN CN2010800074880A patent/CN102316866A/zh active Pending
- 2010-02-12 AU AU2010213362A patent/AU2010213362B2/en not_active Ceased
- 2010-02-12 DK DK10740847.8T patent/DK2395993T3/en active
-
2011
- 2011-07-18 IL IL214133A patent/IL214133A/en active IP Right Grant
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