JP2012532901A - オートタキシン阻害剤としての複素環式化合物 - Google Patents
オートタキシン阻害剤としての複素環式化合物 Download PDFInfo
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- JP2012532901A JP2012532901A JP2012519902A JP2012519902A JP2012532901A JP 2012532901 A JP2012532901 A JP 2012532901A JP 2012519902 A JP2012519902 A JP 2012519902A JP 2012519902 A JP2012519902 A JP 2012519902A JP 2012532901 A JP2012532901 A JP 2012532901A
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- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000875 trofosfamide Drugs 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000005740 tumor formation Effects 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 210000000264 venule Anatomy 0.000 description 1
- 230000007998 vessel formation Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- VLCYCQAOQCDTCN-ZCFIWIBFSA-N α-difluoromethylornithine Chemical compound NCCC[C@@](N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-ZCFIWIBFSA-N 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009033392A DE102009033392A1 (de) | 2009-07-16 | 2009-07-16 | Heterocyclische Verbindungen als Autotaxin-Inhibitoren II |
| DE102009033392.4 | 2009-07-16 | ||
| PCT/EP2010/003661 WO2011006569A1 (de) | 2009-07-16 | 2010-06-17 | Heterocyclische verbindungen als autotaxin-inhibitoren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012532901A true JP2012532901A (ja) | 2012-12-20 |
| JP2012532901A5 JP2012532901A5 (enExample) | 2013-08-08 |
Family
ID=42646326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012519902A Pending JP2012532901A (ja) | 2009-07-16 | 2010-06-17 | オートタキシン阻害剤としての複素環式化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20120115852A1 (enExample) |
| EP (1) | EP2454258A1 (enExample) |
| JP (1) | JP2012532901A (enExample) |
| KR (1) | KR20120090031A (enExample) |
| CN (1) | CN102471343A (enExample) |
| AR (1) | AR077488A1 (enExample) |
| AU (1) | AU2010272922A1 (enExample) |
| BR (1) | BR112012000792A2 (enExample) |
| CA (1) | CA2768095A1 (enExample) |
| DE (1) | DE102009033392A1 (enExample) |
| EA (1) | EA201200119A1 (enExample) |
| IL (1) | IL217466A0 (enExample) |
| MX (1) | MX2012000609A (enExample) |
| SG (1) | SG177522A1 (enExample) |
| WO (1) | WO2011006569A1 (enExample) |
| ZA (1) | ZA201201124B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016510780A (ja) * | 2013-03-12 | 2016-04-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オータキシン阻害剤としての新規オクタヒドロ−ピロロ［３，４−ｃ］−ピロール誘導体及びそのアナログ |
| JP2017510576A (ja) * | 2014-03-26 | 2017-04-13 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オートタキシン（ａｔｘ）及びリゾホスファチジン酸（ｌｐａ）産生の阻害剤としての縮合［１，４］ジアゼピン化合物 |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2861566T1 (sl) | 2012-06-13 | 2017-03-31 | F. Hoffmann-La Roche Ag | Novi diazaspirocikloalkan in azaspirocikloalkan |
| PL2900669T3 (pl) * | 2012-09-25 | 2020-01-31 | F. Hoffmann-La Roche Ag | Pochodne heksahydropirolo[3,4-C]pirolu i związki pokrewne jako inhibitory autotaksyny (ATX) oraz inhibitory produkcji kwasu lizofosfatydowego (LPA) do leczenia np. chorób nerek |
| US9409895B2 (en) | 2012-12-19 | 2016-08-09 | Novartis Ag | Autotaxin inhibitors |
| EP2935249B1 (en) | 2012-12-19 | 2018-12-12 | Novartis AG | Autotaxin inhibitors |
| TW201446768A (zh) * | 2013-03-15 | 2014-12-16 | Biogen Idec Inc | S1p及/或atx調節劑 |
| US9714240B2 (en) | 2013-09-17 | 2017-07-25 | Pharmakea, Inc. | Vinyl autotaxin inhibitor compounds |
| EP3046909A4 (en) | 2013-09-17 | 2017-03-29 | Pharmakea, Inc. | Heterocyclic vinyl autotaxin inhibitor compounds |
| US9850203B2 (en) | 2013-09-26 | 2017-12-26 | Pharmakea, Inc. | Autotaxin inhibitor compounds |
| CA2930735A1 (en) | 2013-11-22 | 2015-05-28 | Sabre Therapeutics Llc | Tetracyclic autotaxin inhibitors |
| PE20160654A1 (es) | 2013-11-22 | 2016-07-15 | Pharmakea Inc | Compuestos de inhibidor de autotaxina |
| AU2014356583B2 (en) | 2013-11-26 | 2019-02-28 | F. Hoffmann-La Roche Ag | New octahydro-cyclobuta (1,2-c;3,4-c')dipyrrol-2-yl |
| MA50635A (fr) | 2014-03-26 | 2020-08-12 | Hoffmann La Roche | Nouveaux composés bicycliques comme inhibiteurs de la production d'autotaxin (atx) et de l'acide lysophosphatidique |
| KR20160133004A (ko) | 2014-04-04 | 2016-11-21 | 엑스-알엑스, 인크. | 오토탁신의 치환된 스피로시클릭 억제제 |
| CN107205972A (zh) * | 2014-04-23 | 2017-09-26 | X-Rx股份有限公司 | 自分泌运动因子的取代的n‑(2‑(氨基)‑2‑氧代乙基)苯甲酰胺抑制剂及它们的制备和在治疗lpa‑依赖的或lpa‑介导的疾病中的用途 |
| US9051320B1 (en) | 2014-08-18 | 2015-06-09 | Pharmakea, Inc. | Methods for the treatment of metabolic disorders by a selective small molecule autotaxin inhibitor |
| GB201501870D0 (en) | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
| GB201502020D0 (en) | 2015-02-06 | 2015-03-25 | Cancer Rec Tech Ltd | Autotaxin inhibitory compounds |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| CN116059203A (zh) | 2015-05-27 | 2023-05-05 | 赛博治疗有限责任公司 | 自分泌运动因子抑制剂及其用途 |
| US10118904B2 (en) | 2015-06-05 | 2018-11-06 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of Demyelinating Diseases |
| GB201510010D0 (en) | 2015-06-09 | 2015-07-22 | King S College London | PDD and BPD compounds |
| GB201514928D0 (en) | 2015-08-21 | 2015-10-07 | King S College London | PDD compounds |
| US20180339985A1 (en) | 2015-08-21 | 2018-11-29 | Femtogenix Limited | Pdd compounds |
| EP3344619B1 (en) | 2015-09-04 | 2020-10-28 | H. Hoffnabb-La Roche Ag | Phenoxymethyl derivatives |
| MA42918A (fr) | 2015-09-24 | 2018-08-01 | Hoffmann La Roche | Composés bicycliques utilisés en tant qu'inhibiteurs d'atx |
| BR112018006080A2 (pt) | 2015-09-24 | 2018-10-09 | F. Hoffmann-La Roche Ag | novos compostos bicíclicos como inibidores de dupla ação de atx/ca |
| AU2016328437A1 (en) | 2015-09-24 | 2018-01-25 | F. Hoffmann-La Roche Ag | Bicyclic compounds as ATX inhibitors |
| WO2017050747A1 (en) | 2015-09-24 | 2017-03-30 | F. Hoffmann-La Roche Ag | New bicyclic compounds as dual atx/ca inhibitors |
| WO2018106643A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Heterocyclic azoles for the treatment of demyelinating diseases |
| WO2018106641A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Pyrazoles for the treatment of demyelinating diseases |
| WO2018106646A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Aminotriazoles for the treatment of demyelinating diseases |
| EP3596060B1 (en) | 2017-03-16 | 2023-09-20 | F. Hoffmann-La Roche AG | New bicyclic compounds as atx inhibitors |
| RU2019132254A (ru) | 2017-03-16 | 2021-04-16 | Ф. Хоффманн-Ля Рош Аг | Гетероциклические соединения, пригодные в качестве дуальных ингибиторов atx/ca |
| JP6687816B1 (ja) * | 2018-05-21 | 2020-04-28 | 株式会社アシックス | ブラジャー |
| WO2020040326A1 (ko) * | 2018-08-23 | 2020-02-27 | 가천대학교 산학협력단 | 페닐아세트산 유도체 및 이를 유효성분으로 함유하는 자가면역질환 예방 또는 치료용 조성물 |
| WO2020072456A1 (en) * | 2018-10-02 | 2020-04-09 | Case Western Reserve University | Compounds for treating myelin related disorders |
| CA3243968A1 (en) * | 2022-02-10 | 2023-08-17 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Fused diazepines as insulin-type peptide receptor (INSL3) RXFP2 agonists and their methods of use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020103373A1 (en) * | 1999-01-19 | 2002-08-01 | Hoekstra William J. | Tricyclic benzodiazepines as vasopressin receptor antagonists |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
| GB9904387D0 (en) | 1999-02-25 | 1999-04-21 | Pharmacia & Upjohn Spa | Antitumour synergistic composition |
| EP1187633A4 (en) | 1999-04-08 | 2005-05-11 | Arch Dev Corp | USE OF ANTI-VEGF ANTIBODIES TO ENHANCE RADIATION IN ANTICANCER THERAPY |
| PT1233787E (pt) * | 1999-11-09 | 2005-04-29 | Conseils Rech S Et D Applic Sc | Produto contendo um inibidor da transducao dos sinais das proteinas g heterotrimericas em associacao com um outro agente anticanceroso para utilizacao terapeutica no tratamento do cancro |
-
2009
- 2009-07-16 DE DE102009033392A patent/DE102009033392A1/de not_active Withdrawn
-
2010
- 2010-06-17 AU AU2010272922A patent/AU2010272922A1/en not_active Abandoned
- 2010-06-17 CA CA2768095A patent/CA2768095A1/en not_active Abandoned
- 2010-06-17 BR BR112012000792A patent/BR112012000792A2/pt not_active Application Discontinuation
- 2010-06-17 SG SG2012000774A patent/SG177522A1/en unknown
- 2010-06-17 US US13/383,908 patent/US20120115852A1/en not_active Abandoned
- 2010-06-17 MX MX2012000609A patent/MX2012000609A/es not_active Application Discontinuation
- 2010-06-17 EA EA201200119A patent/EA201200119A1/ru unknown
- 2010-06-17 KR KR1020127004105A patent/KR20120090031A/ko not_active Withdrawn
- 2010-06-17 JP JP2012519902A patent/JP2012532901A/ja active Pending
- 2010-06-17 EP EP10725398A patent/EP2454258A1/de not_active Withdrawn
- 2010-06-17 CN CN2010800318870A patent/CN102471343A/zh active Pending
- 2010-06-17 WO PCT/EP2010/003661 patent/WO2011006569A1/de not_active Ceased
- 2010-07-16 AR ARP100102610A patent/AR077488A1/es unknown
-
2012
- 2012-01-10 IL IL217466A patent/IL217466A0/en unknown
- 2012-02-15 ZA ZA2012/01124A patent/ZA201201124B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020103373A1 (en) * | 1999-01-19 | 2002-08-01 | Hoekstra William J. | Tricyclic benzodiazepines as vasopressin receptor antagonists |
Non-Patent Citations (7)
| Title |
|---|
| JPN7014002234; ＳＴＮ Ｒｅｇｉｓｔｒｙ ［Ｏｎｌｉｎｅ］ , 2008 * |
| JPN7014002235; ＳＴＮ Ｒｅｇｉｓｔｒｙ ［Ｏｎｌｉｎｅ］ , 2008 * |
| JPN7014002236; ＺＩＮＣ１２６０４９５６ ［Ｏｎｌｉｎｅ］ , 2008 * |
| JPN7014002237; ＺＩＮＣ１２６０５１０４ ［Ｏｎｌｉｎｅ］ , 2008 * |
| JPN7014002238; ＺＩＮＣ０４２３５９１７ ［Ｏｎｌｉｎｅ］ , 2005 * |
| JPN7014002239; ＺＩＮＣ０４２３５８５２ ［Ｏｎｌｉｎｅ］ , 2005 * |
| JPN7014002240; ＺＩＮＣ０４２３５８５１ ［Ｏｎｌｉｎｅ］ , 2005 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016510780A (ja) * | 2013-03-12 | 2016-04-11 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オータキシン阻害剤としての新規オクタヒドロ−ピロロ［３，４−ｃ］−ピロール誘導体及びそのアナログ |
| JP2017510576A (ja) * | 2014-03-26 | 2017-04-13 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | オートタキシン（ａｔｘ）及びリゾホスファチジン酸（ｌｐａ）産生の阻害剤としての縮合［１，４］ジアゼピン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2012000609A (es) | 2012-01-27 |
| SG177522A1 (en) | 2012-02-28 |
| CA2768095A1 (en) | 2011-01-20 |
| CN102471343A (zh) | 2012-05-23 |
| DE102009033392A1 (de) | 2011-01-20 |
| IL217466A0 (en) | 2012-02-29 |
| AU2010272922A1 (en) | 2012-03-08 |
| US20120115852A1 (en) | 2012-05-10 |
| AR077488A1 (es) | 2011-08-31 |
| ZA201201124B (en) | 2012-11-28 |
| BR112012000792A2 (pt) | 2016-02-23 |
| KR20120090031A (ko) | 2012-08-16 |
| WO2011006569A1 (de) | 2011-01-20 |
| EP2454258A1 (de) | 2012-05-23 |
| EA201200119A1 (ru) | 2012-07-30 |
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