CA2731909A1 - 5-alkynyl-pyrimidines - Google Patents
5-alkynyl-pyrimidines Download PDFInfo
- Publication number
- CA2731909A1 CA2731909A1 CA2731909A CA2731909A CA2731909A1 CA 2731909 A1 CA2731909 A1 CA 2731909A1 CA 2731909 A CA2731909 A CA 2731909A CA 2731909 A CA2731909 A CA 2731909A CA 2731909 A1 CA2731909 A1 CA 2731909A1
- Authority
- CA
- Canada
- Prior art keywords
- mmol
- membered
- amino
- hzn
- pyrimidin
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 151
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- 238000011282 treatment Methods 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- -1 -NC Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 29
- 206010028980 Neoplasm Diseases 0.000 claims description 28
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- 239000000126 substance Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 238000004007 reversed phase HPLC Methods 0.000 description 15
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- 238000001914 filtration Methods 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
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- 239000012043 crude product Substances 0.000 description 12
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- NTZVQZUJERRVRW-UHFFFAOYSA-N 5-[2-(6-aminopyridin-3-yl)ethynyl]-4-chloro-6-methylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(Cl)=C1C#CC1=CC=C(N)N=C1 NTZVQZUJERRVRW-UHFFFAOYSA-N 0.000 description 11
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- FLHZBTLBILVJOJ-UHFFFAOYSA-N 4-chloro-5-iodo-6-methylpyrimidin-2-amine Chemical compound CC1=NC(N)=NC(Cl)=C1I FLHZBTLBILVJOJ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 10
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- 238000006069 Suzuki reaction reaction Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- ZVGIVKMNLUTRPN-UHFFFAOYSA-N 5-ethynylpyridin-2-amine Chemical compound NC1=CC=C(C#C)C=N1 ZVGIVKMNLUTRPN-UHFFFAOYSA-N 0.000 description 7
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- NPTGVVKPLWFPPX-UHFFFAOYSA-N 2-amino-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(N)=N1 NPTGVVKPLWFPPX-UHFFFAOYSA-N 0.000 description 6
- LIYYESZTBRETLZ-UHFFFAOYSA-N 5-iodo-4-methyl-6-(4-methylsulfonylphenyl)pyrimidin-2-amine Chemical compound CC1=NC(N)=NC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1I LIYYESZTBRETLZ-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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 two hetero rings
- C07D401/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- 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
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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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- A61P37/02—Immunomodulators
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
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- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Laminated Bodies (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08161369 | 2008-07-29 | ||
| EP08161369.7 | 2008-07-29 | ||
| PCT/EP2009/059763 WO2010012740A1 (en) | 2008-07-29 | 2009-07-28 | 5-alkynyl-pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2731909A1 true CA2731909A1 (en) | 2010-02-04 |
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| CA2731909A Abandoned CA2731909A1 (en) | 2008-07-29 | 2009-07-28 | 5-alkynyl-pyrimidines |
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Families Citing this family (14)
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| JP5651110B2 (ja) | 2008-07-29 | 2015-01-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規化合物 |
| CA2731909A1 (en) | 2008-07-29 | 2010-02-04 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyrimidines |
| AR076332A1 (es) * | 2009-04-21 | 2011-06-01 | Boehringer Ingelheim Int | Derivados heterociclicos de 5-alquinil-piridinas, composiciones farmaceuticas que los comprenden y uso de los mismos para el tratamiento y/o prevencion del cancer, procesos inflamatorios, autoinmunes, y/o infecciones. |
| UY33199A (es) | 2010-01-26 | 2011-08-31 | Boehringer Ingelheim Int | 5-alquinil-pirimidinas. |
| US8618111B2 (en) * | 2010-01-26 | 2013-12-31 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyrimidines |
| US8466162B2 (en) * | 2011-01-26 | 2013-06-18 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyridines |
| TW201245176A (en) * | 2011-01-26 | 2012-11-16 | Boehringer Ingelheim Int | New 5-alkynyl-pyridines |
| EP2736514B1 (en) * | 2011-07-28 | 2017-10-18 | Nerviano Medical Sciences S.r.l. | Alkynyl substituted pyrimidinyl-pyrroles active as kinases inhibitors |
| UA110995C2 (uk) * | 2011-10-07 | 2016-03-10 | Ф. Хоффманн-Ля Рош Аг | Етинільні похідні як модулятори метаботропного глутаматного рецептора |
| PL3080100T3 (pl) | 2013-12-11 | 2023-03-06 | Celgene Quanticel Research, Inc. | Inhibitory lizyno-specyficznej demetylazy-1 |
| HUE057895T2 (hu) | 2014-05-01 | 2022-06-28 | Celgene Quanticel Res Inc | Lizinspecifikus demetiláz-1 inhibitorai |
| ES2935114T3 (es) * | 2014-09-05 | 2023-03-01 | Celgene Quanticel Res Inc | Inhibidores de la desmetilasa 1 específica de lisina |
| CN104744376A (zh) * | 2015-03-14 | 2015-07-01 | 长沙深橙生物科技有限公司 | 一种2-异丙基嘧啶衍生物的制备方法 |
| CN104803921A (zh) * | 2015-03-14 | 2015-07-29 | 长沙深橙生物科技有限公司 | 一种苯取代嘧啶衍生物的制备方法 |
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| DE3832570A1 (de) * | 1988-09-24 | 1990-03-29 | Hoechst Ag | 7-substituierte derivate der 3,5-dihydroxyhept-6-insaeure, verfahren zur ihrer herstellung, ihre verwendung als arzneimittel, sowie zwischenprodukte |
| JPH08504798A (ja) | 1992-12-18 | 1996-05-21 | ザ ウエルカム ファウンデーション リミテッド | 酵素阻害薬としての，ピリミジン，ピリジン，プテリジノンおよびインダゾール誘導体 |
| US5622954A (en) | 1994-05-11 | 1997-04-22 | Fmc Corporation | 5[W(substituted aryl)alkenylene and alkynylene]-2,4-diaminopyrimidines as pesticides |
| ATE293962T1 (de) | 2000-02-25 | 2005-05-15 | Hoffmann La Roche | Adenosin-rezeptor modulatoren |
| JP5154728B2 (ja) * | 2000-07-24 | 2013-02-27 | クレニツキー・ファーマシューティカルズ，インコーポレイテッド | 神経栄養活性を有する置換５−アルキニルピリミジン |
| CA2528938A1 (en) * | 2003-06-13 | 2005-02-24 | Zentaris Gmbh | Compounds having inhibitive activity of phosphatidylinositol 3-kinase and methods of use thereof |
| EP1737462B1 (en) | 2003-12-24 | 2008-07-30 | AstraZeneca AB | Pyrimidines with tie2 (tek) activity |
| EP1761540B1 (en) * | 2004-05-13 | 2016-09-28 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
| US7776869B2 (en) | 2004-10-18 | 2010-08-17 | Amgen Inc. | Heteroaryl-substituted alkyne compounds and method of use |
| WO2006082371A1 (en) | 2005-02-01 | 2006-08-10 | Astrazeneca Ab | Pyrimidine compounds having tie2 (tek) inhibitory activity |
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| US20070135437A1 (en) | 2005-03-04 | 2007-06-14 | Alsgen, Inc. | Modulation of neurodegenerative diseases |
| JP4993205B2 (ja) | 2005-03-30 | 2012-08-08 | 塩野義製薬株式会社 | チロシンキナーゼ阻害作用を有するピリミジン誘導体 |
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| AU2006302179C1 (en) * | 2005-10-07 | 2013-06-20 | Exelixis, Inc. | N- (3-amino-quinoxalin-2-yl) -sulfonamide derivatives and their use as phosphatidylinositol 3-kinase inhibitors |
| JO2660B1 (en) * | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| JP2010501537A (ja) | 2006-08-24 | 2010-01-21 | アストラゼネカ アクチボラグ | 増殖性障害の治療に有用なモルホリノピリミジン誘導体 |
| CN106045965A (zh) | 2006-12-29 | 2016-10-26 | 爱尔兰詹森科学公司 | 抑制hiv的5,6‑取代的嘧啶类化合物 |
| EP2022785A1 (en) | 2007-06-20 | 2009-02-11 | Bayer Schering Pharma Aktiengesellschaft | Alkynylpyrimidines as Tie2 kinase inhibitors |
| CA2731909A1 (en) | 2008-07-29 | 2010-02-04 | Boehringer Ingelheim International Gmbh | 5-alkynyl-pyrimidines |
| UY33199A (es) | 2010-01-26 | 2011-08-31 | Boehringer Ingelheim Int | 5-alquinil-pirimidinas. |
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- 2009-07-28 JP JP2011520491A patent/JP5599791B2/ja active Active
- 2009-07-28 KR KR1020117003951A patent/KR20110041536A/ko not_active Withdrawn
- 2009-07-28 DK DK09781207.7T patent/DK2323992T3/en active
- 2009-07-28 PL PL09781207T patent/PL2323992T3/pl unknown
- 2009-07-28 BR BRPI0916679A patent/BRPI0916679A2/pt not_active IP Right Cessation
- 2009-07-28 US US13/055,949 patent/US8916548B2/en active Active
- 2009-07-28 AR ARP090102873A patent/AR072845A1/es unknown
- 2009-07-28 MX MX2011000729A patent/MX2011000729A/es unknown
- 2009-07-28 CN CN2009801301499A patent/CN102112450A/zh active Pending
- 2009-07-28 UY UY0001032009A patent/UY32009A/es not_active Application Discontinuation
- 2009-07-28 EP EP09781207.7A patent/EP2323992B1/en active Active
- 2009-07-28 HU HUE09781207A patent/HUE029837T2/en unknown
- 2009-07-28 PE PE2011000088A patent/PE20110196A1/es not_active Application Discontinuation
- 2009-07-28 EA EA201100255A patent/EA201100255A1/ru unknown
- 2009-07-28 TW TW098125388A patent/TW201010984A/zh unknown
- 2009-07-28 AU AU2009275957A patent/AU2009275957A1/en not_active Abandoned
-
2010
- 2010-12-29 IL IL210343A patent/IL210343A0/en unknown
-
2011
- 2011-01-26 MA MA33560A patent/MA32505B1/fr unknown
- 2011-01-27 CO CO11009242A patent/CO6341617A2/es not_active Application Discontinuation
- 2011-01-27 EC EC2011010786A patent/ECSP11010786A/es unknown
- 2011-01-28 CL CL2011000195A patent/CL2011000195A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8916548B2 (en) | 2014-12-23 |
| BRPI0916679A2 (pt) | 2015-11-17 |
| DK2323992T3 (en) | 2016-10-31 |
| PE20110196A1 (es) | 2011-04-03 |
| ES2597903T3 (es) | 2017-01-24 |
| UY32009A (es) | 2010-02-26 |
| AU2009275957A1 (en) | 2010-02-04 |
| WO2010012740A1 (en) | 2010-02-04 |
| ECSP11010786A (es) | 2011-02-28 |
| PL2323992T3 (pl) | 2017-01-31 |
| KR20110041536A (ko) | 2011-04-21 |
| MX2011000729A (es) | 2011-03-15 |
| MA32505B1 (fr) | 2011-07-03 |
| HUE029837T2 (en) | 2017-04-28 |
| US20110281838A1 (en) | 2011-11-17 |
| CL2011000195A1 (es) | 2011-07-08 |
| NZ590558A (en) | 2012-12-21 |
| EP2323992B1 (en) | 2016-07-20 |
| JP2011529468A (ja) | 2011-12-08 |
| CO6341617A2 (es) | 2011-11-21 |
| AR072845A1 (es) | 2010-09-22 |
| EP2323992A1 (en) | 2011-05-25 |
| TW201010984A (en) | 2010-03-16 |
| JP5599791B2 (ja) | 2014-10-01 |
| EA201100255A1 (ru) | 2011-08-30 |
| IL210343A0 (en) | 2011-03-31 |
| CN102112450A (zh) | 2011-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20150728 |