CA2691776C - Substituted imidazoheterocycles - Google Patents
Substituted imidazoheterocycles Download PDFInfo
- Publication number
- CA2691776C CA2691776C CA2691776A CA2691776A CA2691776C CA 2691776 C CA2691776 C CA 2691776C CA 2691776 A CA2691776 A CA 2691776A CA 2691776 A CA2691776 A CA 2691776A CA 2691776 C CA2691776 C CA 2691776C
- Authority
- CA
- Canada
- Prior art keywords
- carboxamide
- methyl
- dimethyl
- methylamino
- oxobutan
- 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.)
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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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- 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
-
- 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
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93675407P | 2007-06-21 | 2007-06-21 | |
| US60/936,754 | 2007-06-21 | ||
| US99442207P | 2007-09-19 | 2007-09-19 | |
| US60/994,422 | 2007-09-19 | ||
| US839507P | 2007-12-19 | 2007-12-19 | |
| US61/008,395 | 2007-12-19 | ||
| PCT/US2008/067632 WO2008157751A2 (en) | 2007-06-21 | 2008-06-20 | Substituted imidazoheterocycles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2691776A1 CA2691776A1 (en) | 2008-12-24 |
| CA2691776C true CA2691776C (en) | 2016-05-10 |
Family
ID=40137137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2691776A Active CA2691776C (en) | 2007-06-21 | 2008-06-20 | Substituted imidazoheterocycles |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US7517874B2 (https=) |
| EP (1) | EP2170350B1 (https=) |
| JP (1) | JP5485148B2 (https=) |
| KR (1) | KR101605210B1 (https=) |
| CN (1) | CN101686989B (https=) |
| AU (1) | AU2008265655B2 (https=) |
| BR (1) | BRPI0812504B8 (https=) |
| CA (1) | CA2691776C (https=) |
| EA (1) | EA201000046A1 (https=) |
| ES (1) | ES2439255T3 (https=) |
| IL (1) | IL202616A0 (https=) |
| MY (1) | MY146924A (https=) |
| NZ (1) | NZ582760A (https=) |
| WO (1) | WO2008157751A2 (https=) |
Families Citing this family (67)
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| US9006175B2 (en) | 1999-06-29 | 2015-04-14 | Mannkind Corporation | Potentiation of glucose elimination |
| WO2003080149A2 (en) | 2002-03-20 | 2003-10-02 | Mannkind Corporation | Inhalation apparatus |
| PL1786784T3 (pl) | 2004-08-20 | 2011-04-29 | Mannkind Corp | Kataliza syntezy diketopiperazyn |
| KR101644250B1 (ko) | 2004-08-23 | 2016-07-29 | 맨카인드 코포레이션 | 약물 전달용 디케토피페라진염, 디케토모르포린염 또는 디케토디옥산염 |
| CN104324362B (zh) | 2005-09-14 | 2018-04-24 | 曼金德公司 | 以提高活性试剂对结晶微粒表面的亲和力为基础的药物配制方法 |
| IN2015DN00888A (https=) | 2006-02-22 | 2015-07-10 | Mannkind Corp | |
| US8859538B2 (en) * | 2007-06-21 | 2014-10-14 | Cara Therapeutics, Inc. | Uses of substituted imidazoheterocycles |
| CN101686989B (zh) * | 2007-06-21 | 2016-10-19 | 卡拉治疗学股份有限公司 | 取代的咪唑并杂环 |
| US20090062253A1 (en) * | 2007-08-31 | 2009-03-05 | Kalypsys, Inc. | Heterocyclodiazepine cannabinoid receptor modulators for treatment of disease |
| CN101468988A (zh) * | 2007-12-26 | 2009-07-01 | 上海恒瑞医药有限公司 | 哌嗪类衍生物,其制备方法及其在医药上的应用 |
| ES2929343T3 (es) | 2008-06-13 | 2022-11-28 | Mannkind Corp | Inhalador de polvo seco accionado por aspiración para la administración de fármacos |
| US8485180B2 (en) | 2008-06-13 | 2013-07-16 | Mannkind Corporation | Dry powder drug delivery system |
| KR101628410B1 (ko) | 2008-06-20 | 2016-06-08 | 맨카인드 코포레이션 | 흡입 활동에 관한 실시간 프로파일링을 위한 대화형 장치 및 방법 |
| TWI614024B (zh) | 2008-08-11 | 2018-02-11 | 曼凱公司 | 超快起作用胰島素之用途 |
| US8314106B2 (en) | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
| TW201030007A (en) * | 2009-02-06 | 2010-08-16 | Gruenenthal Gmbh | Substituted spiro-amides as b1r modulators |
| TW201035102A (en) * | 2009-03-04 | 2010-10-01 | Gruenethal Gmbh | Sulfonylated tetrahydroazolopyrazines and their use as medicinal products |
| DK2405963T3 (da) | 2009-03-11 | 2013-12-16 | Mannkind Corp | Apparat, system og fremgangsmåde til at måle modstand i en inhalator |
| CN101899048B (zh) * | 2009-05-27 | 2013-04-17 | 上海恒瑞医药有限公司 | (R)-7-[3-氨基-4-(2,4,5-三氟-苯基)-丁酰]-3-三氟甲基-5,6,7,8-四氢-咪唑并[1,5-a]吡嗪-1-羧酸甲酯的盐 |
| CN104721825B (zh) | 2009-06-12 | 2019-04-12 | 曼金德公司 | 具有确定比表面积的二酮哌嗪颗粒 |
| US8299103B2 (en) * | 2009-06-15 | 2012-10-30 | Boehringer Ingelheim International Gmbh | Compounds which selectively modulate the CB2 receptor |
| IN2012DN02474A (https=) | 2009-08-28 | 2015-08-21 | Arena Pharm Inc | |
| WO2011056889A1 (en) | 2009-11-03 | 2011-05-12 | Mannkind Corporation | An apparatus and method for simulating inhalation efforts |
| PL2552920T3 (pl) | 2010-04-02 | 2017-08-31 | Ogeda Sa | Nowe wybiórcze związki antagonistów receptora NK-3, farmaceutyczne kompozycje i sposoby do zastosowania w zaburzeniach pośredniczonych przez receptory NK-3 |
| US10065960B2 (en) | 2010-04-02 | 2018-09-04 | Ogeda Sa | NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders |
| IL223742A (en) | 2010-06-21 | 2016-06-30 | Mannkind Corp | A dry powder inhaler and preparation for it |
| CN102464661B (zh) * | 2010-11-16 | 2015-04-01 | 天津药明康德新药开发有限公司 | 一种5,6,7,8-四氢-咪唑并[1,5-a]吡嗪-1-羧酸乙酯的制备方法 |
| HU1000676D0 (en) * | 2010-12-17 | 2011-02-28 | Pharmahungary 2000 Kft | Inhibitors of matrix metalloproteinase, pharmaceutical compositions thereof and use of them for preventing and treating diseases where the activation of mmp is involved |
| EP2678330A1 (en) | 2011-02-25 | 2014-01-01 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of condensed azacycles ( cannabinoid receptor modulators) |
| US9597340B2 (en) | 2011-02-25 | 2017-03-21 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
| AU2012222149B2 (en) | 2011-02-25 | 2017-06-29 | Arena Pharmaceuticals, Inc. | Cannabinoid receptor modulators |
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| WO2012174472A1 (en) | 2011-06-17 | 2012-12-20 | Mannkind Corporation | High capacity diketopiperazine microparticles |
| DK2763992T3 (en) | 2011-10-03 | 2016-04-25 | Euroscreen Sa | NOVEL CHIRAL N-acyl-5,6,7, (8-substituted) -tetrahydro [1,2,4] triazolo [4,3-a] pyrazines as selective NK-3 receptor antagonists, PHARMACEUTICAL COMPOSITION AND METHODS FOR THE use in the NK-3 receptor mediated diseases |
| BR112014009686A2 (pt) | 2011-10-24 | 2018-08-07 | Mannkind Corp | composição analgésica inalável, pó seco e método para tratar dor |
| CN104619369B (zh) | 2012-07-12 | 2018-01-30 | 曼金德公司 | 干粉药物输送系统和方法 |
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| AU2014228415B2 (en) | 2013-03-15 | 2018-08-09 | Mannkind Corporation | Microcrystalline diketopiperazine compositions and methods |
| MX375448B (es) | 2013-07-18 | 2025-03-06 | Mannkind Corp | Composiciones farmacéuticas en polvo seco estables al calor y métodos. |
| US11446127B2 (en) | 2013-08-05 | 2022-09-20 | Mannkind Corporation | Insufflation apparatus and methods |
| SG11201604878XA (en) * | 2013-12-20 | 2016-07-28 | Esteve Labor Dr | Fused imidazolyl derivatives, their preparation and use as medicaments |
| US10307464B2 (en) | 2014-03-28 | 2019-06-04 | Mannkind Corporation | Use of ultrarapid acting insulin |
| US10561806B2 (en) | 2014-10-02 | 2020-02-18 | Mannkind Corporation | Mouthpiece cover for an inhaler |
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| US20200140444A1 (en) * | 2017-07-24 | 2020-05-07 | Isocure Biosciences Inc. | Inhibitors of mutant isocitrate dehydrogenases and compositions and methods thereof |
| JP2020528062A (ja) * | 2017-07-27 | 2020-09-17 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ピペラジンヘテロアリール誘導体、その製造方法、およびその医薬での使用 |
| RU2020131507A (ru) * | 2018-03-29 | 2022-05-04 | Боард Оф Реджентс, Де Юниверсити Оф Техас Систем | Имидазопиперазиновые ингибиторы белков-активаторов транскрипции |
| WO2019195846A1 (en) | 2018-04-06 | 2019-10-10 | Board Of Regents, The University Of Texas System | Imidazopiperazinone inhibitors of transcription activating proteins |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
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| CN111484497B (zh) * | 2019-01-25 | 2021-07-02 | 江苏恒瑞医药股份有限公司 | 咪唑并[1,5-a]吡嗪类衍生物的可药用盐、晶型及其制备方法 |
| CN111484498B (zh) * | 2019-01-25 | 2021-05-14 | 江苏恒瑞医药股份有限公司 | 咪唑并[1,5-a]吡嗪类化合物的晶型及其制备方法 |
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| WO2022166778A1 (zh) * | 2021-02-04 | 2022-08-11 | 江苏恒瑞医药股份有限公司 | 一种衣壳蛋白抑制剂的药物组合物及其制备方法 |
| CN121851016A (zh) * | 2021-04-21 | 2026-04-14 | 长春金赛药业有限责任公司 | 含咪唑稠环类衍生物、其制备方法及其在医药上的应用 |
| CA3261924A1 (en) * | 2022-07-14 | 2024-01-18 | The Scripps Research Institute | SMALL MOLECULE REGULATORS OF TYPE 2 ALVEOLAR CELL PROLIFERATION FOR THE TREATMENT OF LUNG DISEASES |
| CN119855819B (zh) * | 2022-10-19 | 2025-10-28 | 长春金赛药业有限责任公司 | 一种nk3r拮抗剂的晶型及其制备方法和应用 |
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- 2008-06-20 NZ NZ582760A patent/NZ582760A/en unknown
- 2008-06-20 EP EP08771568.6A patent/EP2170350B1/en active Active
- 2008-06-20 US US12/142,846 patent/US7517874B2/en active Active
- 2008-06-20 BR BRPI0812504A patent/BRPI0812504B8/pt not_active IP Right Cessation
- 2008-06-20 EA EA201000046A patent/EA201000046A1/ru unknown
- 2008-06-20 JP JP2010513438A patent/JP5485148B2/ja active Active
- 2008-06-20 MY MYPI20095453A patent/MY146924A/en unknown
- 2008-06-20 WO PCT/US2008/067632 patent/WO2008157751A2/en not_active Ceased
- 2008-06-20 CA CA2691776A patent/CA2691776C/en active Active
- 2008-06-20 AU AU2008265655A patent/AU2008265655B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| US7517874B2 (en) | 2009-04-14 |
| EP2170350B1 (en) | 2013-09-11 |
| EP2170350A4 (en) | 2011-09-28 |
| MY146924A (en) | 2012-10-15 |
| KR20100050459A (ko) | 2010-05-13 |
| KR101605210B1 (ko) | 2016-03-21 |
| EA201000046A1 (ru) | 2011-02-28 |
| NZ582760A (en) | 2011-12-22 |
| WO2008157751A2 (en) | 2008-12-24 |
| IL202616A0 (en) | 2010-06-30 |
| BRPI0812504B8 (pt) | 2021-05-25 |
| JP2010530891A (ja) | 2010-09-16 |
| CA2691776A1 (en) | 2008-12-24 |
| CN101686989A (zh) | 2010-03-31 |
| CN101686989B (zh) | 2016-10-19 |
| JP5485148B2 (ja) | 2014-05-07 |
| BRPI0812504B1 (pt) | 2019-12-03 |
| US8431565B2 (en) | 2013-04-30 |
| US20080318935A1 (en) | 2008-12-25 |
| BRPI0812504A2 (pt) | 2015-06-16 |
| AU2008265655A1 (en) | 2008-12-24 |
| AU2008265655B2 (en) | 2014-02-06 |
| WO2008157751A3 (en) | 2009-03-12 |
| ES2439255T3 (es) | 2014-01-22 |
| EP2170350A2 (en) | 2010-04-07 |
| US20090149450A1 (en) | 2009-06-11 |
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