CA2810896A1 - Crystalline oxalate salts of a diamide compound - Google Patents
Crystalline oxalate salts of a diamide compound Download PDFInfo
- Publication number
- CA2810896A1 CA2810896A1 CA2810896A CA2810896A CA2810896A1 CA 2810896 A1 CA2810896 A1 CA 2810896A1 CA 2810896 A CA2810896 A CA 2810896A CA 2810896 A CA2810896 A CA 2810896A CA 2810896 A1 CA2810896 A1 CA 2810896A1
- Authority
- CA
- Canada
- Prior art keywords
- oxalate salt
- crystalline oxalate
- crystalline
- hydroxy
- salt
- 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
- 150000003891 oxalate salts Chemical class 0.000 title claims abstract description 104
- -1 diamide compound Chemical class 0.000 title description 8
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- 239000003814 drug Substances 0.000 claims description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 19
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 14
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- 238000002560 therapeutic procedure Methods 0.000 claims description 4
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- AKYUMGLGSXQSCR-FAIXQHPJSA-N [1-[3-[[5-[4-[[[(2r)-2-hydroxy-2-(8-hydroxy-2-oxo-1h-quinolin-5-yl)ethyl]amino]methyl]anilino]-5-oxopentyl]-methylamino]-3-oxopropyl]piperidin-4-yl] n-(2-phenylphenyl)carbamate Chemical compound C=1C=C(CNC[C@H](O)C=2C=3C=CC(=O)NC=3C(O)=CC=2)C=CC=1NC(=O)CCCCN(C)C(=O)CCN(CC1)CCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 AKYUMGLGSXQSCR-FAIXQHPJSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 59
- QMOVGVNKXUTCQU-UHFFFAOYSA-N (2-phenylphenyl)carbamic acid Chemical class OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-N 0.000 abstract description 33
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 33
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 abstract description 33
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 33
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical class O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 201000010099 disease Diseases 0.000 description 7
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 7
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- 229920006395 saturated elastomer Polymers 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 108060003345 Adrenergic Receptor Proteins 0.000 description 5
- 102000017910 Adrenergic receptor Human genes 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- ROCHZUNCIZLTRQ-UHFFFAOYSA-N oxalic acid;propan-2-ol Chemical compound CC(C)O.OC(=O)C(O)=O ROCHZUNCIZLTRQ-UHFFFAOYSA-N 0.000 description 5
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
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- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 229960002969 oleic acid Drugs 0.000 description 1
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- 239000004006 olive oil Substances 0.000 description 1
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- 230000002611 ovarian Effects 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- 230000001185 psoriatic effect Effects 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 description 1
- 229950004432 rofleponide Drugs 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
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- 229940090585 serevent Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 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
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
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Classifications
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38814810P | 2010-09-30 | 2010-09-30 | |
| US61/388,148 | 2010-09-30 | ||
| PCT/US2011/053997 WO2012044825A1 (en) | 2010-09-30 | 2011-09-29 | Crystalline oxalate salts of a diamide compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2810896A1 true CA2810896A1 (en) | 2012-04-05 |
Family
ID=44903347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2810896A Abandoned CA2810896A1 (en) | 2010-09-30 | 2011-09-29 | Crystalline oxalate salts of a diamide compound |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8697724B2 (enExample) |
| EP (1) | EP2621917A1 (enExample) |
| JP (2) | JP2013538857A (enExample) |
| KR (1) | KR20130139919A (enExample) |
| CN (1) | CN103140485B (enExample) |
| AR (1) | AR083115A1 (enExample) |
| AU (1) | AU2011308770B2 (enExample) |
| BR (1) | BR112013007062A2 (enExample) |
| CA (1) | CA2810896A1 (enExample) |
| CL (1) | CL2013000870A1 (enExample) |
| CO (1) | CO6700846A2 (enExample) |
| EA (1) | EA022018B1 (enExample) |
| IL (1) | IL224985A (enExample) |
| MX (1) | MX2013003558A (enExample) |
| NZ (1) | NZ608721A (enExample) |
| PH (1) | PH12013500567A1 (enExample) |
| SG (1) | SG188390A1 (enExample) |
| TW (1) | TW201217338A (enExample) |
| WO (1) | WO2012044825A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| ITRM20110083U1 (it) | 2010-05-13 | 2011-11-14 | De La Cruz Jose Antonio Freire | Piastra per la costruzione di carrelli per aeroplani |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EA201500651A1 (ru) | 2012-12-18 | 2015-11-30 | Альмираль, С.А. | НОВЫЕ ПРОИЗВОДНЫЕ ЦИКЛОГЕКСИЛ- И ХИНУКЛИДИНИЛКАРБАМАТА, ОБЛАДАЮЩИЕ АГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К β2 АДРЕНЕРГИЧЕСКОМУ РЕЦЕПТОРУ И АНТАГОНИСТИЧЕСКОЙ АКТИВНОСТЬЮ ПО ОТНОШЕНИЮ К МУСКАРИНОВОМУ РЕЦЕПТОРУ М3 |
| TWI643853B (zh) | 2013-02-27 | 2018-12-11 | 阿爾米雷爾有限公司 | 同時具有β2腎上腺素受體促效劑和M3毒蕈鹼受體拮抗劑活性之2-氨基-1-羥乙基-8-羥基喹啉-2(1H)-酮衍生物之鹽類 |
| TW201517906A (zh) | 2013-07-25 | 2015-05-16 | Almirall Sa | 含有ｍａｂａ化合物和皮質類固醇之組合 |
| TWI641373B (zh) | 2013-07-25 | 2018-11-21 | 阿爾米雷爾有限公司 | 具有蕈毒鹼受體拮抗劑和β２腎上腺素受體促效劑二者之活性的２－胺基－１－羥乙基－８－羥基喹啉－２（１Ｈ）－酮衍生物之鹽 |
| CN104030933A (zh) * | 2014-05-16 | 2014-09-10 | 烟台恒迪克能源科技有限公司 | 一种β-异烷醇基氨基戊酸环己胺的合成方法 |
| TW201617343A (zh) | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物 |
| CN117924216A (zh) * | 2024-01-12 | 2024-04-26 | 王叔和生物医药(武汉)有限公司 | 一种1-哌啶丙酸的合成方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6759398B2 (en) | 2000-08-05 | 2004-07-06 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative |
| US6750210B2 (en) | 2000-08-05 | 2004-06-15 | Smithkline Beecham Corporation | Formulation containing novel anti-inflammatory androstane derivative |
| US6858596B2 (en) | 2000-08-05 | 2005-02-22 | Smithkline Beecham Corporation | Formulation containing anti-inflammatory androstane derivative |
| AU7649701A (en) | 2000-08-05 | 2002-02-18 | Glaxo Group Ltd | 17.beta.-carbothioate 17.alpha.-arylcarbonyloxyloxy androstane derivative as anti-inflammatory agents |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| PE20040950A1 (es) * | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| US7317102B2 (en) * | 2003-04-01 | 2008-01-08 | Theravance, Inc. | Diarylmethyl and related compounds |
| US7320990B2 (en) | 2004-02-13 | 2008-01-22 | Theravance, Inc. | Crystalline form of a biphenyl compound |
| WO2006023460A2 (en) * | 2004-08-16 | 2006-03-02 | Theravance, Inc. | COMPOUNDS HAVING β2 ADRENERGIC RECEPTOR AGONIST AND MUSCARINIC RECEPTOR ANTAGONIST ACTIVITY |
| TWI374883B (en) | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
| GB0602778D0 (en) * | 2006-02-10 | 2006-03-22 | Glaxo Group Ltd | Novel compound |
| TW200811104A (en) | 2006-04-25 | 2008-03-01 | Theravance Inc | Crystalline forms of a dimethylphenyl compound |
| EP2421849B1 (en) * | 2009-04-23 | 2013-04-03 | Theravance, Inc. | Diamide compounds having muscarinic receptor antagonist and beta2 adrenergic receptor agonist activity |
-
2011
- 2011-09-26 AR ARP110103518A patent/AR083115A1/es unknown
- 2011-09-29 NZ NZ60872111A patent/NZ608721A/en not_active IP Right Cessation
- 2011-09-29 US US13/248,840 patent/US8697724B2/en not_active Expired - Fee Related
- 2011-09-29 PH PH1/2013/500567A patent/PH12013500567A1/en unknown
- 2011-09-29 KR KR1020137009556A patent/KR20130139919A/ko not_active Withdrawn
- 2011-09-29 SG SG2013016043A patent/SG188390A1/en unknown
- 2011-09-29 EA EA201390481A patent/EA022018B1/ru not_active IP Right Cessation
- 2011-09-29 CN CN201180046585.5A patent/CN103140485B/zh not_active Expired - Fee Related
- 2011-09-29 JP JP2013531861A patent/JP2013538857A/ja not_active Ceased
- 2011-09-29 WO PCT/US2011/053997 patent/WO2012044825A1/en not_active Ceased
- 2011-09-29 AU AU2011308770A patent/AU2011308770B2/en not_active Ceased
- 2011-09-29 BR BR112013007062A patent/BR112013007062A2/pt not_active IP Right Cessation
- 2011-09-29 CA CA2810896A patent/CA2810896A1/en not_active Abandoned
- 2011-09-29 MX MX2013003558A patent/MX2013003558A/es not_active Application Discontinuation
- 2011-09-29 EP EP11771325.5A patent/EP2621917A1/en not_active Withdrawn
- 2011-09-30 TW TW100135675A patent/TW201217338A/zh unknown
-
2013
- 2013-02-28 IL IL224985A patent/IL224985A/en not_active IP Right Cessation
- 2013-03-28 CL CL2013000870A patent/CL2013000870A1/es unknown
- 2013-04-02 CO CO13061812A patent/CO6700846A2/es active IP Right Grant
-
2015
- 2015-06-01 JP JP2015111163A patent/JP2015155470A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AR083115A1 (es) | 2013-01-30 |
| AU2011308770A1 (en) | 2013-03-28 |
| AU2011308770B2 (en) | 2015-03-05 |
| TW201217338A (en) | 2012-05-01 |
| NZ608721A (en) | 2015-03-27 |
| BR112013007062A2 (pt) | 2016-06-14 |
| KR20130139919A (ko) | 2013-12-23 |
| CO6700846A2 (es) | 2013-06-28 |
| CL2013000870A1 (es) | 2013-07-12 |
| CN103140485A (zh) | 2013-06-05 |
| EP2621917A1 (en) | 2013-08-07 |
| PH12013500567A1 (en) | 2013-05-06 |
| EA201390481A1 (ru) | 2013-08-30 |
| SG188390A1 (en) | 2013-04-30 |
| US8697724B2 (en) | 2014-04-15 |
| CN103140485B (zh) | 2014-10-22 |
| MX2013003558A (es) | 2013-05-01 |
| IL224985A (en) | 2015-08-31 |
| WO2012044825A1 (en) | 2012-04-05 |
| JP2015155470A (ja) | 2015-08-27 |
| JP2013538857A (ja) | 2013-10-17 |
| EA022018B1 (ru) | 2015-10-30 |
| US20120083478A1 (en) | 2012-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20170929 |