JP2014517049A - （ｓ）−ピロリジン−１，２−ジカルボン酸２−アミド１−（｛４−メチル−５−［２−（２，２，２−トリフルオロ−１，１−ジメチル−エチル）−ピリジン−４−イル］−チアゾール−２−イル｝−アミドの多形 - Google Patents
（ｓ）−ピロリジン−１，２−ジカルボン酸２−アミド１−（｛４−メチル−５−［２−（２，２，２−トリフルオロ−１，１−ジメチル−エチル）−ピリジン−４−イル］−チアゾール−２−イル｝−アミドの多形 Download PDFInfo
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
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- 210000003205 muscle Anatomy 0.000 description 1
- 206010028537 myelofibrosis Diseases 0.000 description 1
- DPDJXTANWGNJOE-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)acetamide Chemical compound CC(=O)NC1=NC(C)=CS1 DPDJXTANWGNJOE-UHFFFAOYSA-N 0.000 description 1
- KEGKIKXJRKOGNU-UHFFFAOYSA-N n-[5-(2-tert-butylpyridin-4-yl)-4-methyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1C1=CC=NC(C(C)(C)C)=C1 KEGKIKXJRKOGNU-UHFFFAOYSA-N 0.000 description 1
- OFTAATVRCGTOPI-UHFFFAOYSA-N n-[5-(2-tert-butylpyridin-4-yl)-4-methyl-1,3-thiazol-2-yl]imidazole-1-carboxamide Chemical compound S1C(C=2C=C(N=CC=2)C(C)(C)C)=C(C)N=C1NC(=O)N1C=CN=C1 OFTAATVRCGTOPI-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 229940060184 oil ingredients Drugs 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000012858 packaging process Methods 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 238000011170 pharmaceutical development Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229940100996 sodium bisulfate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940001482 sodium sulfite Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161499222P | 2011-06-21 | 2011-06-21 | |
| US61/499,222 | 2011-06-21 | ||
| PCT/EP2012/061756 WO2012175522A1 (en) | 2011-06-21 | 2012-06-19 | Polymorphs of (s)-pyrrolidine-1,2-dicarboxylic acid 2-amide 1-({4-methyl-5-[2-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-pyridin-4-yl]-thiazol-2-yl}-amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2014517049A true JP2014517049A (ja) | 2014-07-17 |
Family
ID=46319784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014516316A Pending JP2014517049A (ja) | 2011-06-21 | 2012-06-19 | （ｓ）−ピロリジン−１，２−ジカルボン酸２−アミド１−（｛４−メチル−５−［２−（２，２，２−トリフルオロ−１，１−ジメチル−エチル）−ピリジン−４−イル］−チアゾール−２−イル｝−アミドの多形 |
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| US (1) | US9006270B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2723733A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2014517049A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20140033432A (cg-RX-API-DMAC7.html) |
| CN (1) | CN103619840B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112013032687A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2839621A1 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2014DN00145A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2013014887A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2014101626A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2012175522A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011066352A1 (en) | 2009-11-27 | 2011-06-03 | Genzyme Corporation | An amorphous and a crystalline form of genz 112638 hemitartrat as inhibitor of glucosylceramide synthase |
| AU2013239624A1 (en) * | 2012-03-30 | 2014-10-02 | Novartis Ag | Compounds for use in the treatment of neuroblastoma, Ewing's Sarcoma or rhabdomyosarcoma |
| JP2016539149A (ja) * | 2013-12-06 | 2016-12-15 | ノバルティス アーゲー | アルファ−アイソフォーム選択的ホスファチジルイノシトール３−キナーゼ阻害剤の投薬レジメン |
| JP6723229B2 (ja) * | 2014-10-03 | 2020-07-15 | ノバルティス アーゲー | アルペリシブを含む医薬組成物 |
| AU2020257301B2 (en) | 2019-04-18 | 2025-10-23 | The Johns Hopkins University | Substituted 2-amino-pyrazolyl-(1,2,4)triazolo(1,5a) pyridine derivatives and use thereof |
| CN112961090A (zh) * | 2019-12-13 | 2021-06-15 | 武汉九州钰民医药科技有限公司 | 合成Alpelisib的关键中间体及其制备方法 |
| CN110964005A (zh) * | 2019-12-16 | 2020-04-07 | 武汉九州钰民医药科技有限公司 | 一种Alpelisib的制备工艺 |
| CN111057051A (zh) * | 2019-12-16 | 2020-04-24 | 武汉九州钰民医药科技有限公司 | PI3K抑制剂Alpelisib的新合成方法 |
| JP7649637B2 (ja) | 2020-10-06 | 2025-03-21 | エルジー ディスプレイ カンパニー リミテッド | 伝送装置及び表示システム |
| CA3217167A1 (en) * | 2021-05-03 | 2022-11-10 | Novartis Ag | Alpelisib formulation |
| CN116925023B (zh) * | 2023-07-18 | 2025-11-21 | 江苏桐孚高新材料有限公司 | 2-全氟烷基-4h-吡喃-4-酮衍生物的改进合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010029082A1 (en) * | 2008-09-10 | 2010-03-18 | Novartis Ag | Organic compounds |
| WO2012016970A1 (en) * | 2010-08-02 | 2012-02-09 | Novartis Ag | A crystalline form of (s)-pyrrolidine-1,2-dicarboxylic acid 2-amide 1-(4 -methyl-5-[2-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-pyridin-4-yl]-thiazol-2-yl)-amide and its use as pi3k inhibitor |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY29149A1 (es) * | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| CN101484452A (zh) * | 2006-05-03 | 2009-07-15 | 阿斯利康(瑞典)有限公司 | 噻唑衍生物及其作为抗肿瘤药物的用途 |
-
2012
- 2012-06-19 MX MX2013014887A patent/MX2013014887A/es not_active Application Discontinuation
- 2012-06-19 JP JP2014516316A patent/JP2014517049A/ja active Pending
- 2012-06-19 IN IN145DEN2014 patent/IN2014DN00145A/en unknown
- 2012-06-19 BR BR112013032687A patent/BR112013032687A2/pt not_active IP Right Cessation
- 2012-06-19 CN CN201280030432.6A patent/CN103619840B/zh not_active Expired - Fee Related
- 2012-06-19 KR KR1020137033590A patent/KR20140033432A/ko not_active Withdrawn
- 2012-06-19 RU RU2014101626/04A patent/RU2014101626A/ru not_active Application Discontinuation
- 2012-06-19 EP EP12728285.3A patent/EP2723733A1/en not_active Withdrawn
- 2012-06-19 CA CA2839621A patent/CA2839621A1/en not_active Abandoned
- 2012-06-19 WO PCT/EP2012/061756 patent/WO2012175522A1/en not_active Ceased
- 2012-06-19 US US14/127,027 patent/US9006270B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010029082A1 (en) * | 2008-09-10 | 2010-03-18 | Novartis Ag | Organic compounds |
| WO2012016970A1 (en) * | 2010-08-02 | 2012-02-09 | Novartis Ag | A crystalline form of (s)-pyrrolidine-1,2-dicarboxylic acid 2-amide 1-(4 -methyl-5-[2-(2,2,2-trifluoro-1,1-dimethyl-ethyl)-pyridin-4-yl]-thiazol-2-yl)-amide and its use as pi3k inhibitor |
Non-Patent Citations (3)
| Title |
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| 塩路雄作著, 固形製剤の製造技術, vol. 普及版, JPN6011023134, 27 January 2003 (2003-01-27), pages 9 - 12, ISSN: 0003241132 * |
| 有機化合物結晶作製ハンドブック −原理とノウハウ−, JPN6011053065, 25 July 2008 (2008-07-25), pages 57 - 84, ISSN: 0003241134 * |
| 芹澤一英, 医薬品の多形現象と晶析の化学, JPN6015027444, 2002, pages 273 - 278, ISSN: 0003241133 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2839621A1 (en) | 2012-12-27 |
| CN103619840A (zh) | 2014-03-05 |
| US9006270B2 (en) | 2015-04-14 |
| RU2014101626A (ru) | 2015-07-27 |
| WO2012175522A1 (en) | 2012-12-27 |
| AU2012274141B2 (en) | 2015-12-24 |
| BR112013032687A2 (pt) | 2016-08-30 |
| KR20140033432A (ko) | 2014-03-18 |
| US20140171470A1 (en) | 2014-06-19 |
| IN2014DN00145A (cg-RX-API-DMAC7.html) | 2015-05-22 |
| AU2012274141A1 (en) | 2013-12-12 |
| MX2013014887A (es) | 2014-02-17 |
| EP2723733A1 (en) | 2014-04-30 |
| CN103619840B (zh) | 2016-01-20 |
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