JP2010523522A - Ｊａｋ３阻害剤としてのピロロピリミジン誘導体 - Google Patents
Ｊａｋ３阻害剤としてのピロロピリミジン誘導体 Download PDFInfo
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- JP2010523522A JP2010523522A JP2010501495A JP2010501495A JP2010523522A JP 2010523522 A JP2010523522 A JP 2010523522A JP 2010501495 A JP2010501495 A JP 2010501495A JP 2010501495 A JP2010501495 A JP 2010501495A JP 2010523522 A JP2010523522 A JP 2010523522A
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- 229960004919 procaine Drugs 0.000 description 1
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- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
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- 238000006268 reductive amination reaction Methods 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 208000002491 severe combined immunodeficiency Diseases 0.000 description 1
- 230000007781 signaling event Effects 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
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- 229960002167 sodium tartrate Drugs 0.000 description 1
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
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- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WZIWYAUOBGPYLC-UHFFFAOYSA-N tert-butyl 4-(aminomethyl)piperidine-1-carboxylate;piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1.CC(C)(C)OC(=O)N1CCC(CN)CC1 WZIWYAUOBGPYLC-UHFFFAOYSA-N 0.000 description 1
- CTEDVGRUGMPBHE-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)CC1 CTEDVGRUGMPBHE-UHFFFAOYSA-N 0.000 description 1
- BJBIMVUYRLMGTP-UHFFFAOYSA-N tert-butyl 4-(imidazol-1-ylmethyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CN1C=NC=C1 BJBIMVUYRLMGTP-UHFFFAOYSA-N 0.000 description 1
- RXNQBVRCZIYUJK-UHFFFAOYSA-N tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(COS(C)(=O)=O)CC1 RXNQBVRCZIYUJK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- 238000013518 transcription Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QTRZWHHIPMVGPE-UHFFFAOYSA-N trimethyl-[2-[[4-(4-nitrophenyl)pyrazol-1-yl]methoxy]ethyl]silane Chemical compound C1=NN(COCC[Si](C)(C)C)C=C1C1=CC=C([N+]([O-])=O)C=C1 QTRZWHHIPMVGPE-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Classifications
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- 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
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| EP07380088 | 2007-04-02 | ||
| PCT/EP2008/053842 WO2008119792A1 (en) | 2007-04-02 | 2008-03-31 | Pyrrolopyrimidine derivatives as jak3 inhibitors |
Publications (2)
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| JP2010523522A true JP2010523522A (ja) | 2010-07-15 |
| JP2010523522A5 JP2010523522A5 (enExample) | 2011-05-19 |
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Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20110160185A9 (enExample) |
| EP (1) | EP2142550A1 (enExample) |
| JP (1) | JP2010523522A (enExample) |
| KR (1) | KR20100015353A (enExample) |
| CN (1) | CN101679440A (enExample) |
| AR (1) | AR065901A1 (enExample) |
| AU (1) | AU2008234822A1 (enExample) |
| BR (1) | BRPI0809992A2 (enExample) |
| CA (1) | CA2682646A1 (enExample) |
| CL (1) | CL2008000946A1 (enExample) |
| IL (1) | IL201073A0 (enExample) |
| MX (1) | MX2009010595A (enExample) |
| PE (1) | PE20090996A1 (enExample) |
| RU (1) | RU2009140319A (enExample) |
| TW (1) | TW200904442A (enExample) |
| WO (1) | WO2008119792A1 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012510972A (ja) * | 2008-12-05 | 2012-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピロロピラジニル尿素キナーゼ阻害薬 |
| JP2013537542A (ja) * | 2010-08-20 | 2013-10-03 | ハチソン メディファーマ リミテッド | ピロロピリミジン化合物およびその使用 |
| JP2016505025A (ja) * | 2013-01-18 | 2016-02-18 | シャンハイ ケメックスプローラー カンパニー，リミティド | 五員かつ六員複素環式化合物並びにその製造方法、医薬品組成物及びその使用 |
| JP2016520098A (ja) * | 2013-05-24 | 2016-07-11 | ユーハン・コーポレイションＹＵＨＡＮ Ｃｏｒｐｏｒａｔｉｏｎ | ピリミジン環を含む二環式誘導体及びその製造方法 |
| JP2017019877A (ja) * | 2009-07-31 | 2017-01-26 | 日本たばこ産業株式会社 | 含窒素スピロ環化合物及びその医薬用途 |
| JP2017524022A (ja) * | 2014-08-21 | 2017-08-24 | ファイザー・インク | Ｊａｋ阻害剤としてのアミノピリミジニル化合物 |
| JP2017524703A (ja) * | 2014-07-25 | 2017-08-31 | シャンハイ ハイヤン ファーマシューティカル テクノロジー カンパニー リミテッドＳｈａｎｇｈａｉ Ｈａｉｙａｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | ２，４−二置換７Ｈ−ピロロ［２，３−ｄ］ピリミジン誘導体、その製造方法および医薬における使用 |
| JP2018515581A (ja) * | 2015-05-28 | 2018-06-14 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋキナーゼ阻害剤としてのナフチリジン化合物 |
| JP2022506682A (ja) * | 2018-11-05 | 2022-01-17 | アビスタ ファーマ ソリューションズ，インコーポレーテッド | 化合物 |
| JP2022538493A (ja) * | 2019-07-04 | 2022-09-02 | 沈陽薬科大学 | ２－アミノピリミジン化合物及びその使用 |
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|---|---|---|---|---|
| WO2009026107A1 (en) | 2007-08-17 | 2009-02-26 | Portola Pharmaceuticals, Inc. | Protein kinase inhibitors |
| US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| US8063058B2 (en) | 2008-04-16 | 2011-11-22 | Portola Pharmaceuticals, Inc. | Inhibitors of syk and JAK protein kinases |
| WO2009131687A2 (en) * | 2008-04-22 | 2009-10-29 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
| TW201024298A (en) * | 2008-09-23 | 2010-07-01 | Palau Pharma Sa | (R)-3-(N,N-dimethylamino)pyrrolidine derivatives |
| HRP20150701T1 (hr) * | 2009-06-08 | 2015-08-28 | Takeda Pharmaceutical Company Limited | Spojevi dihidropirolonaftiridinona kao inhibitori jak |
| AU2010311378B2 (en) * | 2009-10-29 | 2014-04-24 | Vectura Limited | N-containing heteroaryl derivatives as JAK3 kinase inhibitors |
| JP2013533868A (ja) * | 2010-07-09 | 2013-08-29 | レオ ファーマ アクティーゼルスカブ | タンパク質チロシンキナーゼ阻害剤としての新規ホモピペラジン誘導体およびそれらの医薬使用 |
| WO2012030924A1 (en) * | 2010-09-01 | 2012-03-08 | Ambit Biosciences Corporation | Azolopyridine and azolopyrimidine compounds and methods of use thereof |
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| CZ20004727A3 (cs) * | 1998-06-19 | 2002-03-13 | Pfizer Products Inc. | Deriváty pyrrolo[2,3-d] pyrimidinu |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| ES2320487T3 (es) * | 2005-02-03 | 2009-05-22 | Vertex Pharmaceuticals, Inc. | Pirrolopirimidinas utiles como inhibidores de proteina quinasas. |
| GB0526246D0 (en) * | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
-
2008
- 2008-03-31 AU AU2008234822A patent/AU2008234822A1/en not_active Abandoned
- 2008-03-31 MX MX2009010595A patent/MX2009010595A/es not_active Application Discontinuation
- 2008-03-31 CA CA002682646A patent/CA2682646A1/en not_active Abandoned
- 2008-03-31 CN CN200880015843A patent/CN101679440A/zh active Pending
- 2008-03-31 JP JP2010501495A patent/JP2010523522A/ja not_active Withdrawn
- 2008-03-31 US US12/594,228 patent/US20110160185A9/en not_active Abandoned
- 2008-03-31 BR BRPI0809992-8A2A patent/BRPI0809992A2/pt not_active IP Right Cessation
- 2008-03-31 WO PCT/EP2008/053842 patent/WO2008119792A1/en not_active Ceased
- 2008-03-31 PE PE2008000586A patent/PE20090996A1/es not_active Application Discontinuation
- 2008-03-31 KR KR1020097020666A patent/KR20100015353A/ko not_active Withdrawn
- 2008-03-31 RU RU2009140319/04A patent/RU2009140319A/ru not_active Application Discontinuation
- 2008-03-31 EP EP08735625A patent/EP2142550A1/en not_active Withdrawn
- 2008-03-31 AR ARP080101351A patent/AR065901A1/es not_active Application Discontinuation
- 2008-04-01 TW TW097111869A patent/TW200904442A/zh unknown
- 2008-04-01 CL CL200800946A patent/CL2008000946A1/es unknown
-
2009
- 2009-09-21 IL IL201073A patent/IL201073A0/en unknown
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| JP2012510972A (ja) * | 2008-12-05 | 2012-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピロロピラジニル尿素キナーゼ阻害薬 |
| JP2017019877A (ja) * | 2009-07-31 | 2017-01-26 | 日本たばこ産業株式会社 | 含窒素スピロ環化合物及びその医薬用途 |
| JP2018111701A (ja) * | 2009-07-31 | 2018-07-19 | 日本たばこ産業株式会社 | 含窒素スピロ環化合物及びその医薬用途 |
| JP2013537542A (ja) * | 2010-08-20 | 2013-10-03 | ハチソン メディファーマ リミテッド | ピロロピリミジン化合物およびその使用 |
| JP2016505025A (ja) * | 2013-01-18 | 2016-02-18 | シャンハイ ケメックスプローラー カンパニー，リミティド | 五員かつ六員複素環式化合物並びにその製造方法、医薬品組成物及びその使用 |
| JP2016520098A (ja) * | 2013-05-24 | 2016-07-11 | ユーハン・コーポレイションＹＵＨＡＮ Ｃｏｒｐｏｒａｔｉｏｎ | ピリミジン環を含む二環式誘導体及びその製造方法 |
| JP2017524703A (ja) * | 2014-07-25 | 2017-08-31 | シャンハイ ハイヤン ファーマシューティカル テクノロジー カンパニー リミテッドＳｈａｎｇｈａｉ Ｈａｉｙａｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | ２，４−二置換７Ｈ−ピロロ［２，３−ｄ］ピリミジン誘導体、その製造方法および医薬における使用 |
| JP2017524022A (ja) * | 2014-08-21 | 2017-08-24 | ファイザー・インク | Ｊａｋ阻害剤としてのアミノピリミジニル化合物 |
| JP2018515581A (ja) * | 2015-05-28 | 2018-06-14 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋキナーゼ阻害剤としてのナフチリジン化合物 |
| JP2020111593A (ja) * | 2015-05-28 | 2020-07-27 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋキナーゼ阻害剤としてのナフチリジン化合物 |
| JP2021001196A (ja) * | 2015-05-28 | 2021-01-07 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | Ｊａｋキナーゼ阻害剤としてのナフチリジン化合物 |
| JP2022506682A (ja) * | 2018-11-05 | 2022-01-17 | アビスタ ファーマ ソリューションズ，インコーポレーテッド | 化合物 |
| JP2022538493A (ja) * | 2019-07-04 | 2022-09-02 | 沈陽薬科大学 | ２－アミノピリミジン化合物及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110160185A9 (en) | 2011-06-30 |
| AU2008234822A1 (en) | 2008-10-09 |
| US20100113420A1 (en) | 2010-05-06 |
| WO2008119792A1 (en) | 2008-10-09 |
| CN101679440A (zh) | 2010-03-24 |
| CL2008000946A1 (es) | 2008-10-10 |
| CA2682646A1 (en) | 2008-10-09 |
| KR20100015353A (ko) | 2010-02-12 |
| PE20090996A1 (es) | 2009-07-15 |
| EP2142550A1 (en) | 2010-01-13 |
| MX2009010595A (es) | 2009-10-22 |
| IL201073A0 (en) | 2010-05-17 |
| RU2009140319A (ru) | 2011-05-10 |
| AR065901A1 (es) | 2009-07-08 |
| TW200904442A (en) | 2009-02-01 |
| BRPI0809992A2 (pt) | 2014-10-14 |
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