KR101720824B1 - 카테콜 o-메틸 트랜스퍼라제의 억제제 및 정신병적 장애의 치료에서의 그의 용도 - Google Patents
카테콜 o-메틸 트랜스퍼라제의 억제제 및 정신병적 장애의 치료에서의 그의 용도 Download PDFInfo
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- KR101720824B1 KR101720824B1 KR1020127023048A KR20127023048A KR101720824B1 KR 101720824 B1 KR101720824 B1 KR 101720824B1 KR 1020127023048 A KR1020127023048 A KR 1020127023048A KR 20127023048 A KR20127023048 A KR 20127023048A KR 101720824 B1 KR101720824 B1 KR 101720824B1
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- Prior art keywords
- aryl
- pyridine
- alkyl
- phenyl
- pyridin
- Prior art date
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- 0 C*C(N(C=C1OCc2ccccc2)c2cc(-c3ccccc3)ccc2)=CC1=O Chemical compound C*C(N(C=C1OCc2ccccc2)c2cc(-c3ccccc3)ccc2)=CC1=O 0.000 description 2
- OHKNMOCDRUMSJE-UHFFFAOYSA-N CC(N(C=C1O)c2cc(-c3ccccc3)ccc2)=CC1=O Chemical compound CC(N(C=C1O)c2cc(-c3ccccc3)ccc2)=CC1=O OHKNMOCDRUMSJE-UHFFFAOYSA-N 0.000 description 1
- QTCDARUVRYYQMB-UHFFFAOYSA-N CC(OC=C1OCc2ccccc2)=CC1=O Chemical compound CC(OC=C1OCc2ccccc2)=CC1=O QTCDARUVRYYQMB-UHFFFAOYSA-N 0.000 description 1
- NQKIRSCGMQLCBX-UHFFFAOYSA-N CC1C=CC(c2c(CNN3)c3ccc2)NC1N(C=CC1=O)C=C1O Chemical compound CC1C=CC(c2c(CNN3)c3ccc2)NC1N(C=CC1=O)C=C1O NQKIRSCGMQLCBX-UHFFFAOYSA-N 0.000 description 1
- NFKWYFMVGCBACB-UHFFFAOYSA-N CCCCc(cc1)ccc1N(C=C(C1=O)OCc2ccccc2)C=C1Br Chemical compound CCCCc(cc1)ccc1N(C=C(C1=O)OCc2ccccc2)C=C1Br NFKWYFMVGCBACB-UHFFFAOYSA-N 0.000 description 1
- LQBBJTIHARTVTQ-UHFFFAOYSA-N CNC(N(C=C1O)c2cccc(-c3ccccc3)c2)=CC1=O Chemical compound CNC(N(C=C1O)c2cccc(-c3ccccc3)c2)=CC1=O LQBBJTIHARTVTQ-UHFFFAOYSA-N 0.000 description 1
- ARKGRWCHTWQAKE-UHFFFAOYSA-N COc(cc1)ccc1-c1nc2cc(N(C=CC3=O)C=C3O)ccc2[nH]1 Chemical compound COc(cc1)ccc1-c1nc2cc(N(C=CC3=O)C=C3O)ccc2[nH]1 ARKGRWCHTWQAKE-UHFFFAOYSA-N 0.000 description 1
- WCDCAXVNBOLWNO-UHFFFAOYSA-N Fc1ncccc1I Chemical compound Fc1ncccc1I WCDCAXVNBOLWNO-UHFFFAOYSA-N 0.000 description 1
- APNXHQOSBORUQT-UHFFFAOYSA-N O=C1C(OCc2ccccc2)=COC(CCl)=C1 Chemical compound O=C1C(OCc2ccccc2)=COC(CCl)=C1 APNXHQOSBORUQT-UHFFFAOYSA-N 0.000 description 1
- IAMQYYMWXQPFDC-UHFFFAOYSA-N OC(C(C=C1)=O)=CN1c1cc(-c2ccccc2)ccc1 Chemical compound OC(C(C=C1)=O)=CN1c1cc(-c2ccccc2)ccc1 IAMQYYMWXQPFDC-UHFFFAOYSA-N 0.000 description 1
- ISZIHIRAJCSPCS-UHFFFAOYSA-N OC(C(C=C1)=O)=CN1c1cccc2c1nc[n]2Cc(cccc1)c1Cl Chemical compound OC(C(C=C1)=O)=CN1c1cccc2c1nc[n]2Cc(cccc1)c1Cl ISZIHIRAJCSPCS-UHFFFAOYSA-N 0.000 description 1
- VEYIMQVTPXPUHA-UHFFFAOYSA-N OC1=COC=CC1=O Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 1
- BEJNERDRQOWKJM-UHFFFAOYSA-N OCC(OC=C1O)=CC1=O Chemical compound OCC(OC=C1O)=CC1=O BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
- ZGEXYNBHYVEWKT-UHFFFAOYSA-N OCC(OC=C1OCc2ccccc2)=CC1=O Chemical compound OCC(OC=C1OCc2ccccc2)=CC1=O ZGEXYNBHYVEWKT-UHFFFAOYSA-N 0.000 description 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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Applications Claiming Priority (3)
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| US31041010P | 2010-03-04 | 2010-03-04 | |
| US61/310,410 | 2010-03-04 | ||
| PCT/US2011/026399 WO2011109254A1 (en) | 2010-03-04 | 2011-02-28 | Inhibitors of catechol o-methyl transferase and their use in the treatment of psychotic disorders |
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| KR20130044205A KR20130044205A (ko) | 2013-05-02 |
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| US9024032B2 (en) * | 2010-03-04 | 2015-05-05 | Merck Sharp & Dohme Corp. | Inhibitors of catechol O-methyl transferase and their use in the treatment of psychotic disorders |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| PE20141361A1 (es) | 2011-11-15 | 2014-10-13 | Takeda Pharmaceutical | Compuesto heterociclico dihidroxi aromatico |
| TWI638802B (zh) * | 2012-05-24 | 2018-10-21 | 芬蘭商奧利安公司 | 兒茶酚o-甲基轉移酶活性抑制化合物 |
| CN103845317B (zh) * | 2012-11-28 | 2018-05-08 | 北京生命科学研究所 | 恩他卡朋在预防或治疗肥胖等代谢综合征中的应用 |
| GB201222711D0 (en) | 2012-12-17 | 2013-01-30 | Takeda Pharmaceutical | Novel compounds |
| WO2014102233A1 (en) * | 2012-12-27 | 2014-07-03 | F. Hoffmann-La Roche Ag | Comt inhibitors |
| US9067917B2 (en) | 2013-03-15 | 2015-06-30 | Janssen Pharmaceutica Nv | 1,2,5-substituted benzimidazoles as FLAP modulators |
| WO2014151380A1 (en) | 2013-03-15 | 2014-09-25 | Janssen Pharmaceutica Nv | 1,2,6-substituted benzimidazoles as flap modulators |
| CN103588702B (zh) * | 2013-10-26 | 2016-01-06 | 浙江大学 | N-取代苯基吡啶-4-酮衍生物及其制备和应用 |
| JP6422164B2 (ja) | 2013-12-26 | 2018-11-14 | 塩野義製薬株式会社 | 含窒素6員環誘導体およびそれらを含有する医薬組成物 |
| JP6858712B2 (ja) | 2015-01-30 | 2021-04-14 | リーバー インスティテュート フォー ブレイン ディベロップメントLieber Institute For Brain Development | Comt阻害方法及び組成物 |
| ES2905399T3 (es) | 2015-04-24 | 2022-04-08 | Shionogi & Co | Derivados heterocíclicos de seis miembros y composición farmacéutica que los comprende |
| WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| DK3377488T3 (da) | 2015-11-19 | 2022-10-03 | Incyte Corp | Heterocykliske forbindelser som immunomodulatorer |
| PL3380471T3 (pl) * | 2015-11-25 | 2021-12-20 | Lieber Institute Inc. Dba Lieber Institute For Brain Development | Tetrahydro-8h-pirydo[1,2-a]pirazyn-8-ony jako inhibitory comt do leczenia chorób i zaburzeń neurodegeneracyjnych |
| CN105481812B (zh) * | 2015-11-30 | 2020-04-21 | 重庆天奕恒化科技有限公司 | 一种5-苄氧基-4-氧代-4h-吡喃-2-羧酸的制备方法 |
| MY199705A (en) | 2015-12-22 | 2023-11-20 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| TW201808950A (zh) | 2016-05-06 | 2018-03-16 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| SG11201811414TA (en) | 2016-06-20 | 2019-01-30 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| EP3484866B1 (en) | 2016-07-14 | 2022-09-07 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| MA46045A (fr) | 2016-08-29 | 2021-04-28 | Incyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| CN110072862B (zh) | 2016-10-17 | 2022-05-13 | 盐野义制药株式会社 | 二环性含氮杂环衍生物及含有该衍生物的药物组合物 |
| WO2018119266A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Benzooxazole derivatives as immunomodulators |
| US20180179202A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| KR102641030B1 (ko) | 2016-12-22 | 2024-02-29 | 인사이트 코포레이션 | Pd-l1 내재화 유도제로서의 테트라하이드로 이미다조[4,5-c]피리딘 유도체 |
| WO2018119236A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Triazolo[1,5-a]pyridine derivatives as immunomodulators |
| WO2018119221A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Pyridine derivatives as immunomodulators |
| RU2019130519A (ru) | 2017-03-31 | 2021-04-30 | Фуджифилм Корпорэйшн | 4-пиридоновое соединение или его соль, фармацевтическая композиция и содержащий их состав |
| CN108191746B (zh) * | 2018-02-02 | 2020-06-16 | 暨南大学 | 一种羟基吡啶酮类化合物及其制备方法与应用 |
| FI3774791T3 (fi) | 2018-03-30 | 2023-03-21 | Incyte Corp | Heterosyklisiä yhdisteitä immunomodulaattoreina |
| BR112020022936A2 (pt) | 2018-05-11 | 2021-02-02 | Incyte Corporation | derivados de tetra-hidro-imidazo[4,5-c]piridina como imunomoduladores de pd-l1 |
| US12415816B2 (en) | 2018-11-07 | 2025-09-16 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| US11753406B2 (en) | 2019-08-09 | 2023-09-12 | Incyte Corporation | Salts of a PD-1/PD-L1 inhibitor |
| MX2022003578A (es) | 2019-09-30 | 2022-05-30 | Incyte Corp | Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores. |
| BR112022009031A2 (pt) | 2019-11-11 | 2022-10-11 | Incyte Corp | Sais e formas cristalinas de um inibidor de pd-1/pd-l1 |
| CN111170936B (zh) | 2020-01-19 | 2021-01-01 | 杭州泽德医药科技有限公司 | 3,4-二羟基-n-(1’-苄基-2’-羟乙基)-2-甲基吡啶氯化物及制备和应用 |
| EP4146639A1 (en) | 2020-05-06 | 2023-03-15 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| KR102377058B1 (ko) | 2020-11-04 | 2022-03-22 | 경북대학교 산학협력단 | 니아스텔라 코리엔시스에서 유래한 카테콜 o-메틸 트렌스퍼라제 및 이의 변이체 |
| MX2023005362A (es) | 2020-11-06 | 2023-06-22 | Incyte Corp | Proceso para hacer un inhibidor de proteina de muerte programada 1 (pd-1)/ligando de muerte programada 1 (pd-l1) y sales y formas cristalinas del mismo. |
| TW202233615A (zh) | 2020-11-06 | 2022-09-01 | 美商英塞特公司 | Pd—1/pd—l1抑制劑之結晶形式 |
| US11780836B2 (en) | 2020-11-06 | 2023-10-10 | Incyte Corporation | Process of preparing a PD-1/PD-L1 inhibitor |
| TW202241889A (zh) | 2020-12-23 | 2022-11-01 | 美商雅捷可斯治療公司 | 作為jak2抑制劑之6-雜芳基氧基苯并咪唑及氮雜苯并咪唑 |
| EP4373487A4 (en) * | 2021-07-19 | 2025-10-29 | Baylor College Medicine | CORONAVIRUS MAJOR PROTEASE INHIBITORS AND THEIR METHODS OF USE |
| JP7782035B2 (ja) | 2021-11-09 | 2025-12-08 | エイジャックス セラピューティクス, インコーポレイテッド | Jak2阻害剤としての6-ヘテロアリールオキシベンゾイミダゾール及びアザベンゾイミダゾール |
| WO2023086320A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of jak2 |
| CN114716366B (zh) * | 2022-04-13 | 2023-12-26 | 浙江大学 | 3-羟基吡啶-4-酮类衍生物及在抑制肾细胞铁死亡中的应用 |
| CN116947812B (zh) * | 2023-06-30 | 2025-09-02 | 南京红太阳医药研究院有限公司 | 一种艾司奥美拉唑镁降解杂质的制备方法 |
| WO2025257687A1 (en) * | 2024-06-11 | 2025-12-18 | Universidade Do Porto | Hydroxypyridinone compounds as inhibitors of catechol-o-methyltransferase |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2001319486A (ja) | 2000-05-12 | 2001-11-16 | Mitsubishi Electric Corp | 不揮発性半導体記憶装置 |
| US20070232663A1 (en) | 2006-03-29 | 2007-10-04 | Pirrung Michael C | Small molecule insulin mimetics absent quinones |
| US20070293464A1 (en) | 2003-11-10 | 2007-12-20 | X-Ceptor Therapeutics, Inc. | Substituted Pyrimidine Compositions and Methods of Use |
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| GB8811055D0 (en) * | 1988-05-10 | 1988-06-15 | Ici Plc | Antibiotic compounds |
| US5336482A (en) * | 1991-12-05 | 1994-08-09 | The Du Pont Merck Pharmaceutical Company | Technetium-99m complexes with N-substituted 3-hydroxy-4-pyridinones |
| FR2687674B1 (fr) * | 1992-02-07 | 1995-05-19 | Roussel Uclaf | Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant. |
| SE0004053D0 (sv) * | 2000-11-06 | 2000-11-06 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
| EP1441735B1 (en) | 2001-10-26 | 2006-02-22 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti S.P.A. | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
| JP2007126716A (ja) * | 2005-11-04 | 2007-05-24 | Miyazaki Tlo:Kk | カドミウムに対する亜鉛の高選択的抽出剤及び亜鉛の回収 |
| JP2009234959A (ja) * | 2008-03-26 | 2009-10-15 | Pias Arise Kk | 3−ヒドロキシ−2−メチル−1−フェニル−4−ピリジノン又はその誘導体からなる美白剤、並びにその美白剤を含有する美白用皮膚外用剤、化粧料 |
| US9024032B2 (en) * | 2010-03-04 | 2015-05-05 | Merck Sharp & Dohme Corp. | Inhibitors of catechol O-methyl transferase and their use in the treatment of psychotic disorders |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001319486A (ja) | 2000-05-12 | 2001-11-16 | Mitsubishi Electric Corp | 不揮発性半導体記憶装置 |
| US20070293464A1 (en) | 2003-11-10 | 2007-12-20 | X-Ceptor Therapeutics, Inc. | Substituted Pyrimidine Compositions and Methods of Use |
| US20070232663A1 (en) | 2006-03-29 | 2007-10-04 | Pirrung Michael C | Small molecule insulin mimetics absent quinones |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5995728B2 (ja) | 2016-09-21 |
| US20150299227A1 (en) | 2015-10-22 |
| CN102869256A (zh) | 2013-01-09 |
| US9399651B2 (en) | 2016-07-26 |
| ES2862931T3 (es) | 2021-10-08 |
| AU2011223969B2 (en) | 2015-06-11 |
| RU2586974C2 (ru) | 2016-06-10 |
| EP2542076A1 (en) | 2013-01-09 |
| CA2789471C (en) | 2018-01-02 |
| US9024032B2 (en) | 2015-05-05 |
| CN102869256B (zh) | 2016-06-22 |
| US20130084346A1 (en) | 2013-04-04 |
| WO2011109254A1 (en) | 2011-09-09 |
| EP2542076B1 (en) | 2021-01-13 |
| AU2011223969A1 (en) | 2012-08-16 |
| EP2542076A4 (en) | 2015-01-14 |
| KR20130044205A (ko) | 2013-05-02 |
| BR112012021652A2 (pt) | 2016-06-21 |
| MX2012010187A (es) | 2012-10-03 |
| JP2013521285A (ja) | 2013-06-10 |
| RU2012142194A (ru) | 2014-04-10 |
| CA2789471A1 (en) | 2011-09-09 |
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