CA2817896A1 - Inhibitors of hiv replication - Google Patents
Inhibitors of hiv replication Download PDFInfo
- Publication number
- CA2817896A1 CA2817896A1 CA2817896A CA2817896A CA2817896A1 CA 2817896 A1 CA2817896 A1 CA 2817896A1 CA 2817896 A CA2817896 A CA 2817896A CA 2817896 A CA2817896 A CA 2817896A CA 2817896 A1 CA2817896 A1 CA 2817896A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- compound
- mmol
- tert
- stirred
- 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
- 239000003112 inhibitor Substances 0.000 title abstract description 22
- 230000010076 replication Effects 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 239000000203 mixture Substances 0.000 claims abstract description 98
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 208000031886 HIV Infections Diseases 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 208000037357 HIV infectious disease Diseases 0.000 claims description 7
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 42
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- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 11
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
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- 229910052786 argon Inorganic materials 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
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- 241001529453 unidentified herpesvirus Species 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
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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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/495—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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Communicable Diseases (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US41361810P | 2010-11-15 | 2010-11-15 | |
| US61/413,618 | 2010-11-15 | ||
| US201161485355P | 2011-05-12 | 2011-05-12 | |
| US61/485,355 | 2011-05-12 | ||
| PCT/IB2011/054852 WO2012066442A1 (en) | 2010-11-15 | 2011-11-01 | Inhibitors of hiv replication |
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| CA2817896A1 true CA2817896A1 (en) | 2012-05-24 |
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| EP (1) | EP2640729B1 (enExample) |
| JP (2) | JP5902704B2 (enExample) |
| CN (2) | CN105330675A (enExample) |
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| AU (2) | AU2011330850B2 (enExample) |
| BR (1) | BR112013011991A2 (enExample) |
| CA (1) | CA2817896A1 (enExample) |
| CL (1) | CL2013001338A1 (enExample) |
| MX (1) | MX343274B (enExample) |
| RU (1) | RU2564445C2 (enExample) |
| TW (1) | TWI445709B (enExample) |
| UY (1) | UY33729A (enExample) |
| WO (1) | WO2012066442A1 (enExample) |
| ZA (1) | ZA201303433B (enExample) |
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| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| EP2588455B1 (en) | 2010-07-02 | 2018-04-04 | Gilead Sciences, Inc. | 2-quinolinyl-acetic acid derivatives as hiv antiviral compounds |
| CN103140474A (zh) | 2010-07-02 | 2013-06-05 | 吉里德科学公司 | 治疗aids的萘-2-基乙酸衍生物 |
| CA2817896A1 (en) * | 2010-11-15 | 2012-05-24 | Viiv Healthcare Uk Limited | Inhibitors of hiv replication |
| KR20140003438A (ko) | 2010-11-15 | 2014-01-09 | 카톨리에케 유니버시테이트 루벤 | 항바이러스성 축합 헤테로사이클릭 화합물 |
| MX2013012266A (es) | 2011-04-21 | 2013-11-22 | Gilead Sciences Inc | Compuestos de benzotiazol y su uso farmaceutico. |
| US9199959B2 (en) | 2011-10-25 | 2015-12-01 | Shionogi & Co., Ltd. | HIV replication inhibitor |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| US9376392B2 (en) | 2012-01-04 | 2016-06-28 | Gilead Sciences, Inc. | 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS |
| ES2571479T3 (es) | 2012-04-20 | 2016-05-25 | Gilead Sciences Inc | Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH |
| US8906929B2 (en) | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| TW201441197A (zh) | 2013-01-31 | 2014-11-01 | Shionogi & Co | Ｈｉｖ複製抑制劑 |
| JP2016516692A (ja) | 2013-03-13 | 2016-06-09 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ヒト免疫不全ウイルス複製の阻害剤 |
| JP2016512511A (ja) | 2013-03-13 | 2016-04-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ヒト免疫不全ウイルス複製の阻害剤 |
| US9655889B2 (en) | 2013-03-13 | 2017-05-23 | VIIV Healthcare UK (No.5) Limited | Inhibitors of human immunodeficiency virus replication |
| EP2970297A1 (en) | 2013-03-14 | 2016-01-20 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| WO2014159959A1 (en) | 2013-03-14 | 2014-10-02 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| KR102345381B1 (ko) | 2013-06-25 | 2021-12-29 | 브리스톨-마이어스 스큅 컴퍼니 | 키나제 억제제로서 유용한 카르바졸 카르복스아미드 화합물 |
| AR096721A1 (es) | 2013-06-25 | 2016-01-27 | Bristol Myers Squibb Co | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos |
| EP2821082A1 (en) | 2013-07-05 | 2015-01-07 | Laboratoire Biodim | Method of producing an inactivated lentivirus, especially HIV, vaccine, kit and method of use |
| WO2015123230A1 (en) | 2014-02-12 | 2015-08-20 | Bristol-Myers Squibb Company | Benzothiazole macrocycles as inhibitors of human immunodeficiency virus replication |
| EP3152215A1 (en) | 2014-02-18 | 2017-04-12 | ViiV Healthcare UK (No.5) Limited | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| WO2015126758A1 (en) | 2014-02-18 | 2015-08-27 | Bristol-Myers Squibb Company | Imidazopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9409922B2 (en) | 2014-02-18 | 2016-08-09 | Bristol-Myers Squibb Company | Imidazopyridine macrocycles as inhibitors of human immunodeficiency virus replication |
| US9273067B2 (en) | 2014-02-19 | 2016-03-01 | Bristol-Myers Squibb Company | Pyrazolopyrimidine macrocycles as inhibitors of human immunodeficiency virus replication |
| ES2687322T3 (es) | 2014-02-19 | 2018-10-24 | VIIV Healthcare UK (No.5) Limited | Inhibidores de la replicación del virus de inmunodeficiencia humana |
| JP6579549B2 (ja) | 2014-05-16 | 2019-09-25 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する３環性複素環誘導体 |
| MX393057B (es) | 2014-10-24 | 2025-03-24 | Bristol Myers Squibb Co | Compuestos de indol carboxamida útiles como inhibidores de cinasas. |
| TWI676618B (zh) | 2014-10-24 | 2019-11-11 | 美商必治妥美雅史谷比公司 | 三環化合物 |
| CN107108555B (zh) | 2014-10-24 | 2020-12-01 | 百时美施贵宝公司 | 三环阻转异构体化合物 |
| US10806734B2 (en) | 2015-05-08 | 2020-10-20 | Katholieke Universiteit Leuven | Functional cure of retroviral infection |
| AU2016271762B2 (en) | 2015-05-29 | 2020-01-23 | Shionogi & Co., Ltd. | Nitrogen-containing tricyclic derivatives having HIV replication inhibitory activity |
| CN111018912A (zh) * | 2019-11-22 | 2020-04-17 | 苏州二叶制药有限公司 | 一种抗病毒药物关键中间体的合成和纯化方法 |
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| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US5489586A (en) * | 1994-03-07 | 1996-02-06 | Warner-Lambert Company | Method for treating inflammatory disease in humans |
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| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| WO2002012189A1 (en) * | 2000-08-09 | 2002-02-14 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| JP2003171381A (ja) | 2001-09-25 | 2003-06-20 | Takeda Chem Ind Ltd | エントリー阻害剤 |
| JP2003119137A (ja) | 2001-10-10 | 2003-04-23 | Japan Tobacco Inc | Ｈｉｖ阻害剤 |
| CA2463975A1 (en) | 2001-10-26 | 2003-05-01 | Maria Emilia Di Francesco | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| AU2002349675A1 (en) | 2001-12-05 | 2003-06-17 | Shionogi And Co., Ltd. | Derivative having hiv integrase inhibitory activity |
| CA2469592C (en) | 2001-12-12 | 2005-08-23 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| US7763641B2 (en) | 2001-12-21 | 2010-07-27 | Tibotec Pharmaceuticals Ltd. | Broadspectrum heterocyclic substituted phenyl containing sulfonamide HIV protease inhibitors |
| EP1467970B1 (en) | 2002-01-17 | 2007-08-22 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as hiv integrase inhibitors |
| TW200306192A (en) | 2002-01-18 | 2003-11-16 | Bristol Myers Squibb Co | Tricyclic 2-pyrimidone compounds useful as HIV reverse transcriptase inhibitors |
| CA2555132A1 (en) * | 2004-02-04 | 2005-08-25 | University Of Virginia Patent Foundation | Compounds that inhibit hiv particle formation |
| ES2324231T3 (es) * | 2004-12-17 | 2009-08-03 | F. Hoffmann-La Roche Ag | Derivados de tieno-piridina como intensificadores alostericos de gaba-b. |
| KR20100108337A (ko) * | 2007-11-15 | 2010-10-06 | 베링거 인겔하임 인터내셔날 게엠베하 | 사람 면역결핍 바이러스 복제의 억제제 |
| RU2402531C2 (ru) * | 2008-09-24 | 2010-10-27 | Александр Леонидович Гинцбург | Биологически активные вещества, подавляющие патогенные бактерии |
| GB0908394D0 (en) * | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| WO2011076765A1 (en) | 2009-12-23 | 2011-06-30 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| CA2817896A1 (en) * | 2010-11-15 | 2012-05-24 | Viiv Healthcare Uk Limited | Inhibitors of hiv replication |
| KR20140003438A (ko) | 2010-11-15 | 2014-01-09 | 카톨리에케 유니버시테이트 루벤 | 항바이러스성 축합 헤테로사이클릭 화합물 |
| US9029391B2 (en) | 2011-01-24 | 2015-05-12 | Viiv Healthcare Uk Limited | Isoquinoline compounds and methods for treating HIV |
| JP6055468B2 (ja) | 2011-07-15 | 2016-12-27 | ヴィーブ ヘルスケア ユーケー リミテッド | アザインドール化合物及びｈｉｖを治療するための方法 |
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2011
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- 2011-11-01 RU RU2013121788/04A patent/RU2564445C2/ru not_active IP Right Cessation
- 2011-11-01 AU AU2011330850A patent/AU2011330850B2/en not_active Ceased
- 2011-11-01 WO PCT/IB2011/054852 patent/WO2012066442A1/en not_active Ceased
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- 2011-11-01 JP JP2013538301A patent/JP5902704B2/ja not_active Expired - Fee Related
- 2011-11-01 CN CN201180065030.5A patent/CN103429595B/zh not_active Expired - Fee Related
- 2011-11-01 BR BR112013011991A patent/BR112013011991A2/pt not_active IP Right Cessation
- 2011-11-10 TW TW100141049A patent/TWI445709B/zh not_active IP Right Cessation
- 2011-11-14 UY UY0001033729A patent/UY33729A/es not_active Application Discontinuation
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- 2011-11-14 US US13/295,167 patent/US8809363B2/en not_active Expired - Fee Related
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2013
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2014
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2016
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- 2016-04-22 AU AU2016202565A patent/AU2016202565A1/en not_active Abandoned
- 2016-08-19 US US15/241,520 patent/US20160355528A1/en not_active Abandoned
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| RU2013121788A (ru) | 2014-12-27 |
| JP2013542247A (ja) | 2013-11-21 |
| CL2013001338A1 (es) | 2014-03-28 |
| AU2011330850B2 (en) | 2016-01-28 |
| CN103429595A (zh) | 2013-12-04 |
| AU2016202565A1 (en) | 2016-05-19 |
| TWI445709B (zh) | 2014-07-21 |
| US8809363B2 (en) | 2014-08-19 |
| RU2564445C2 (ru) | 2015-10-10 |
| EP2640729A1 (en) | 2013-09-25 |
| UY33729A (es) | 2012-06-29 |
| CN103429595B (zh) | 2015-10-21 |
| JP2016164163A (ja) | 2016-09-08 |
| BR112013011991A2 (pt) | 2016-08-30 |
| MX2013005486A (es) | 2013-12-12 |
| JP5902704B2 (ja) | 2016-04-13 |
| TW201300395A (zh) | 2013-01-01 |
| AU2011330850A1 (en) | 2013-06-27 |
| US20120136023A1 (en) | 2012-05-31 |
| ZA201303433B (en) | 2014-12-23 |
| US20160355528A1 (en) | 2016-12-08 |
| WO2012066442A1 (en) | 2012-05-24 |
| AR083870A1 (es) | 2013-03-27 |
| US9447116B2 (en) | 2016-09-20 |
| US20140315927A1 (en) | 2014-10-23 |
| CN105330675A (zh) | 2016-02-17 |
| MX343274B (es) | 2016-10-31 |
| EP2640729B1 (en) | 2016-12-21 |
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