JP2012513380A5 - - Google Patents
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- Publication number
- JP2012513380A5 JP2012513380A5 JP2011541506A JP2011541506A JP2012513380A5 JP 2012513380 A5 JP2012513380 A5 JP 2012513380A5 JP 2011541506 A JP2011541506 A JP 2011541506A JP 2011541506 A JP2011541506 A JP 2011541506A JP 2012513380 A5 JP2012513380 A5 JP 2012513380A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- polyunsaturated fatty
- pharmaceutical composition
- coupling
- 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
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 7
- 239000002537 cosmetic Substances 0.000 claims 5
- 238000005859 coupling reaction Methods 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 4
- -1 hexafluorophosphate Chemical compound 0.000 claims 4
- 150000001735 carboxylic acids Chemical group 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 claims 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims 2
- 235000021292 Docosatetraenoic acid Nutrition 0.000 claims 2
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 229960004488 linolenic acid Drugs 0.000 claims 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims 2
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 claims 2
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 claims 1
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 claims 1
- HPSWUFMMLKGKDS-DNKOKRCQSA-N (2e,4e,6e,8e,10e,12e)-tetracosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O HPSWUFMMLKGKDS-DNKOKRCQSA-N 0.000 claims 1
- FPRKGXIOSIUDSE-SYACGTDESA-N (2z,4z,6z,8z)-docosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C(O)=O FPRKGXIOSIUDSE-SYACGTDESA-N 0.000 claims 1
- KXVFBCSUGDNXQF-DZDBOGACSA-N (2z,4z,6z,8z,10z)-tetracosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C=C/C(O)=O KXVFBCSUGDNXQF-DZDBOGACSA-N 0.000 claims 1
- TWSWSIQAPQLDBP-CGRWFSSPSA-N (7e,10e,13e,16e)-docosa-7,10,13,16-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC(O)=O TWSWSIQAPQLDBP-CGRWFSSPSA-N 0.000 claims 1
- DQGMPXYVZZCNDQ-KBPWROHVSA-N (8E,10E,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C=C/C=C/CCCCCCC(O)=O DQGMPXYVZZCNDQ-KBPWROHVSA-N 0.000 claims 1
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 claims 1
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical compound ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- DQGMPXYVZZCNDQ-UVZPLDOLSA-N Calendinsaeure Natural products CCCCCC=C/C=C/C=C/CCCCCCC(=O)O DQGMPXYVZZCNDQ-UVZPLDOLSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 claims 1
- 235000021297 Eicosadienoic acid Nutrition 0.000 claims 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- TWSWSIQAPQLDBP-UHFFFAOYSA-N adrenic acid Natural products CCCCCC=CCC=CCC=CCC=CCCCCCC(O)=O TWSWSIQAPQLDBP-UHFFFAOYSA-N 0.000 claims 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims 1
- 150000003927 aminopyridines Chemical class 0.000 claims 1
- 235000021342 arachidonic acid Nutrition 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims 1
- 229940090949 docosahexaenoic acid Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims 1
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 claims 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims 1
- 229960002733 gamolenic acid Drugs 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 235000020778 linoleic acid Nutrition 0.000 claims 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- SJSVZAZOZFZHOU-UHFFFAOYSA-N n'-(2-methylbutan-2-yl)-n-propan-2-ylmethanediimine Chemical compound CCC(C)(C)N=C=NC(C)C SJSVZAZOZFZHOU-UHFFFAOYSA-N 0.000 claims 1
- 229940012843 omega-3 fatty acid Drugs 0.000 claims 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 208000008742 seborrheic dermatitis Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0858967 | 2008-12-22 | ||
| FR0858967A FR2940281B1 (fr) | 2008-12-22 | 2008-12-22 | Ester de diol et d'acide gras polyinsature comme agent anti-acne |
| PCT/EP2009/067701 WO2010072738A1 (fr) | 2008-12-22 | 2009-12-21 | Ester de diol et d'acide gras polyinsature comme agent anti-acne |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012513380A JP2012513380A (ja) | 2012-06-14 |
| JP2012513380A5 true JP2012513380A5 (enExample) | 2013-02-14 |
| JP5587333B2 JP5587333B2 (ja) | 2014-09-10 |
Family
ID=40875013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011541506A Active JP5587333B2 (ja) | 2008-12-22 | 2009-12-21 | 抗アクネ剤としての多価不飽和脂肪酸およびジオールエステル |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8623916B2 (enExample) |
| EP (1) | EP2379484B1 (enExample) |
| JP (1) | JP5587333B2 (enExample) |
| KR (1) | KR101676055B1 (enExample) |
| CN (1) | CN102256930B (enExample) |
| AU (1) | AU2009331526B2 (enExample) |
| BR (1) | BRPI0923494B1 (enExample) |
| CA (1) | CA2747681C (enExample) |
| CL (1) | CL2011001539A1 (enExample) |
| CO (1) | CO6390033A2 (enExample) |
| ES (1) | ES2424088T3 (enExample) |
| FR (1) | FR2940281B1 (enExample) |
| GE (1) | GEP20135820B (enExample) |
| IL (1) | IL213646A (enExample) |
| MA (1) | MA32810B1 (enExample) |
| MX (1) | MX2011006659A (enExample) |
| MY (1) | MY151002A (enExample) |
| NZ (1) | NZ593781A (enExample) |
| PL (1) | PL2379484T3 (enExample) |
| PT (1) | PT2379484E (enExample) |
| RU (1) | RU2524779C2 (enExample) |
| SG (1) | SG172342A1 (enExample) |
| TN (1) | TN2011000237A1 (enExample) |
| UA (1) | UA103645C2 (enExample) |
| WO (1) | WO2010072738A1 (enExample) |
| ZA (1) | ZA201103509B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6336902B2 (ja) * | 2011-06-22 | 2018-06-06 | ビョーメ バイオサイエンシズ ピーブイティー．リミテッド | コンジュゲートベースの抗真菌性および抗菌性プロドラッグ |
| FR2983858B1 (fr) * | 2011-12-08 | 2014-01-03 | Fabre Pierre Dermo Cosmetique | Nouveaux composes inhibiteurs de la lipogenese |
| CA2920457A1 (en) * | 2013-08-08 | 2015-02-12 | Galderm Therapeutics Ltd. | Anti-acne compositions comprising bile acid-fatty acid conjugates |
| FR3033135B1 (fr) * | 2015-02-27 | 2018-03-16 | Pierre Fabre Dermo-Cosmetique | Association d'un retinoide et d'un ester de diol et d'acide gras polyinsature |
| FR3053253B1 (fr) * | 2016-07-01 | 2020-01-17 | Pierre Fabre Dermo-Cosmetique | Nouvel extrait d'akenes de silybum marianum et ses utilisations en dermatologie et dermo-cosmetique |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5534762B2 (enExample) | 1975-02-07 | 1980-09-09 | ||
| DE4240674C2 (de) | 1992-11-26 | 1999-06-24 | Schuelke & Mayr Gmbh | Desodorierende Wirkstoffe |
| AU683027B2 (en) * | 1993-01-27 | 1997-10-30 | Scotia Holdings Plc | Triglycerides |
| MY118354A (en) | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| JPH09110818A (ja) * | 1995-10-16 | 1997-04-28 | Sanshin Chem Ind Co Ltd | １−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩の製造方法 |
| ES2176692T3 (es) | 1996-02-21 | 2002-12-01 | Stoa Sa | Composiciones cosmeticas, dermofarmaceuticas o veterinarias para el tratamiento aseptico de la piel humana o animal. |
| GB9620248D0 (en) * | 1996-09-26 | 1996-11-13 | Scotia Holdings Plc | Esters of unsaturated fatty acids |
| GB9622636D0 (en) | 1996-10-30 | 1997-01-08 | Scotia Holdings Plc | Presentation of bioactives |
| GB9710351D0 (en) * | 1997-05-20 | 1997-07-16 | Scotia Holdings Plc | Glucosamine fatty acids |
| WO2001001980A1 (en) * | 1999-07-06 | 2001-01-11 | The Regents Of The University Of California | Methods for the amelioration of neuropsychiatric disorders by inhibiting the inactivating transport of endogenous cannabinoid substances |
| GB9927629D0 (en) * | 1999-11-24 | 2000-01-19 | Croda Int Plc | Compounds |
| ES2208498T3 (es) | 2001-06-22 | 2004-06-16 | SYMRISE GMBH & CO. KG | Uso de 1,2-decanodiol contra germenes causantes de olores corporales desagradables. |
| US20070265352A1 (en) | 2002-02-19 | 2007-11-15 | Joachim Roeding | Synergistic mixtures of at least one 1,2 alkanediol such as 1,2-hexanediol and 1,2-octanediol with a further compound having antimicrobial properties |
| DE10206759A1 (de) | 2002-02-19 | 2003-08-28 | Dragoco Gerberding Co Ag | Synergistische Mischungen von 1,2-Alkandiolen |
| SE0301862D0 (sv) | 2003-06-26 | 2003-06-26 | Jan Faergeman | Sätt att inhibera tillväxten av mot antibiotika resistenta bakterier |
| DE102004031210A1 (de) * | 2004-06-28 | 2006-02-09 | Trommsdorff Gmbh & Co. Kg | MLV-Kosmetikum |
| DE10341179A1 (de) | 2003-09-06 | 2005-03-31 | Beiersdorf Ag | Wirkstoffkombination gegen Akne |
| US7935732B2 (en) | 2004-04-08 | 2011-05-03 | Isp Investments Inc. | Antimicrobial compositions |
| ES2352744T3 (es) * | 2004-04-27 | 2011-02-22 | Akzo Nobel Coatings International Bv | Pintura pigmentada que se desprende a tiras. |
| JP2006056795A (ja) * | 2004-08-18 | 2006-03-02 | Suntory Ltd | ６−ｏ−ｐｕｆａアスコルビン酸エステルを含有する皮膚化粧料並びに飲食品 |
| DE102006044849A1 (de) * | 2006-09-22 | 2008-04-03 | Symrise Gmbh & Co. Kg | Dekonjugierte Alkadiensäureester als Riech- und/oder Aromastoffe |
-
2008
- 2008-12-22 FR FR0858967A patent/FR2940281B1/fr not_active Expired - Fee Related
-
2009
- 2009-12-21 CA CA2747681A patent/CA2747681C/fr active Active
- 2009-12-21 ES ES09797045T patent/ES2424088T3/es active Active
- 2009-12-21 NZ NZ593781A patent/NZ593781A/xx not_active IP Right Cessation
- 2009-12-21 JP JP2011541506A patent/JP5587333B2/ja active Active
- 2009-12-21 CN CN200980151867.4A patent/CN102256930B/zh active Active
- 2009-12-21 UA UAA201108993A patent/UA103645C2/uk unknown
- 2009-12-21 SG SG2011046067A patent/SG172342A1/en unknown
- 2009-12-21 BR BRPI0923494A patent/BRPI0923494B1/pt not_active IP Right Cessation
- 2009-12-21 MY MYPI20112827 patent/MY151002A/en unknown
- 2009-12-21 AU AU2009331526A patent/AU2009331526B2/en not_active Ceased
- 2009-12-21 EP EP09797045.3A patent/EP2379484B1/fr active Active
- 2009-12-21 RU RU2011128264/04A patent/RU2524779C2/ru not_active IP Right Cessation
- 2009-12-21 PT PT97970453T patent/PT2379484E/pt unknown
- 2009-12-21 KR KR1020117013471A patent/KR101676055B1/ko active Active
- 2009-12-21 MX MX2011006659A patent/MX2011006659A/es active IP Right Grant
- 2009-12-21 PL PL09797045T patent/PL2379484T3/pl unknown
- 2009-12-21 GE GEAP200912313A patent/GEP20135820B/en unknown
- 2009-12-21 US US13/130,900 patent/US8623916B2/en active Active
- 2009-12-21 WO PCT/EP2009/067701 patent/WO2010072738A1/fr not_active Ceased
-
2011
- 2011-05-12 TN TN2011000237A patent/TN2011000237A1/fr unknown
- 2011-05-13 ZA ZA2011/03509A patent/ZA201103509B/en unknown
- 2011-05-20 MA MA33865A patent/MA32810B1/fr unknown
- 2011-06-15 CO CO11074814A patent/CO6390033A2/es not_active Application Discontinuation
- 2011-06-19 IL IL213646A patent/IL213646A/en active IP Right Grant
- 2011-06-21 CL CL2011001539A patent/CL2011001539A1/es unknown
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