AR072199A1 - Derivados de fenilimidazol como inhibidores de la enzima pde10a - Google Patents
Derivados de fenilimidazol como inhibidores de la enzima pde10aInfo
- Publication number
- AR072199A1 AR072199A1 ARP090102239A ARP090102239A AR072199A1 AR 072199 A1 AR072199 A1 AR 072199A1 AR P090102239 A ARP090102239 A AR P090102239A AR P090102239 A ARP090102239 A AR P090102239A AR 072199 A1 AR072199 A1 AR 072199A1
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- Argentina
- Prior art keywords
- compound
- formula
- provides
- present
- subject
- Prior art date
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Classifications
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- 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
- C07D403/12—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 chain containing hetero atoms as chain links
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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
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- 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
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Compuestos que son inhibidores de la enzima PDE10A. Proporciona una composicion farmaceutica que comprende una cantidad terapeuticamente efectiva de un compuesto de la presente y un portador farmaceuticamente aceptable. La presente tambien proporciona procesos para la preparacion de los compuestos de formula 1. La presente proporciona adem s un metodo para tratar un sujeto que sufre un trastorno neurodegenerativo, que comprende administrar al sujeto una cantidad terapeuticamente efectiva de un compuesto de formula 1. La presente asimismo proporciona un metodo para tratar un sujeto que sufre una adiccion a las drogas, que comprende administrar al sujeto una cantidad terapeuticamente efectiva de un compuesto de formula 1. La presente tambien proporciona un metodo para tratar un sujeto que sufre un trastorno psiqui trico, que comprende administrar al sujeto una cantidad terapeuticamente efectiva de un compuesto de formula 1. Reivindicacion 1: Un compuesto que tiene la estructura 1 en donde HET es un grupo heteroarom tico de formula 2 que contiene de 2 a 4 tomos de nitrogeno en donde Y puede ser N o CH, Z puede ser N o C, y en donde HET puede estar opcionalmente sustituido con hasta tres sustituyentes R7-R9 individualmente seleccionados de hidrogeno, alquilo C1-6 halogeno; ciano, haloalquilo C1-6; arilo, alcoxi e hidroxialquilo C1-6, y en donde * denota el punto de union, -L- es un ligador seleccionado de -S-CH2- , -CH2-S- ,-CH2-CH2- o -CH=CH-; R1 se selecciona de H, alquilo C1-6, alquil C1-6-cicloalquilo C3-8; hidroxialquilo C1-6, CH2CN, CH2C(O)NH2, arilalquilo C1-6 y aIquil C1-6-heterocicloalquilo, R2-R6 se seleccionan individualmente de H, alcoxi C1-6 y halogeno, y tautomeros y sales de adicion de cido farmaceuticamente aceptables de dicho compuesto, y formas polimorficas de dicho compuesto, siempre que el compuesto no sea 2-(5-fenil-1H-imidazol-2-ilmetilsulfanil)-1H-benzoimidazol o 2-(5-fenil-1H-imidazol-2-il-sulfanilmetil)-1H-benzoimidazol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200800855 | 2008-06-20 | ||
| DKPA200900402 | 2009-03-24 | ||
| DKPA200900519 | 2009-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR072199A1 true AR072199A1 (es) | 2010-08-11 |
Family
ID=40902594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090102239A AR072199A1 (es) | 2008-06-20 | 2009-06-19 | Derivados de fenilimidazol como inhibidores de la enzima pde10a |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US8841297B2 (es) |
| EP (1) | EP2318394B1 (es) |
| JP (1) | JP5930714B2 (es) |
| KR (3) | KR20170016523A (es) |
| CN (2) | CN102124002B (es) |
| AR (1) | AR072199A1 (es) |
| AU (1) | AU2009259209B2 (es) |
| BR (1) | BRPI0915383B8 (es) |
| CA (1) | CA2728335C (es) |
| CL (2) | CL2010001467A1 (es) |
| CO (1) | CO6321263A2 (es) |
| CY (1) | CY1115001T1 (es) |
| DK (1) | DK2318394T3 (es) |
| EA (2) | EA018880B1 (es) |
| ES (1) | ES2456349T3 (es) |
| HR (1) | HRP20140232T1 (es) |
| IL (1) | IL209834A (es) |
| MX (1) | MX2010014136A (es) |
| MY (1) | MY152949A (es) |
| NZ (1) | NZ589926A (es) |
| PL (1) | PL2318394T3 (es) |
| PT (1) | PT2318394E (es) |
| RS (2) | RS53226B (es) |
| SI (1) | SI2318394T1 (es) |
| TW (1) | TWI501965B (es) |
| WO (1) | WO2009152825A1 (es) |
| ZA (1) | ZA201100109B (es) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| UA102693C2 (ru) | 2008-06-20 | 2013-08-12 | Х. Луннбек А/С | Производные фенилимидазола как ингибиторы фермента pde10a |
| TWI501965B (zh) * | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
| TWI485151B (zh) | 2009-12-17 | 2015-05-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之雜芳香族苯基咪唑衍生物 |
| TWI481607B (zh) | 2009-12-17 | 2015-04-21 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑的２－芳基咪唑衍生物 |
| CA2792844C (en) * | 2010-03-12 | 2014-12-09 | Omeros Corporation | Pde10 inhibitors and related compositions and methods |
| US8410117B2 (en) * | 2010-03-26 | 2013-04-02 | Hoffmann-La Roche Inc. | Imidazopyrimidine derivatives |
| US8969349B2 (en) * | 2010-05-26 | 2015-03-03 | Sunovion Pharmaceuticals Inc. | Substituted quinoxalines and quinoxalinones as PDE-10 inhibitors |
| TW201215607A (en) | 2010-07-02 | 2012-04-16 | Lundbeck & Co As H | Aryl-and heteroarylamid derivatives as PDE10A enzyme inhibitor |
| TW201206935A (en) | 2010-07-16 | 2012-02-16 | Lundbeck & Co As H | Triazolo-and pyrazoloquinazoline derivatives as PDE10A enzyme inhibitor |
| WO2012018058A1 (ja) * | 2010-08-04 | 2012-02-09 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| US9029536B2 (en) * | 2010-08-04 | 2015-05-12 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| SI2637704T1 (sl) | 2010-11-10 | 2015-07-31 | H. Lundbeck A/S | Ligandi na osnovi radioaktivno označenega fenilimidazola |
| US8552045B2 (en) | 2010-11-19 | 2013-10-08 | H. Lundbeck A/S | Tricyclic imidazole compounds as PDE10 inhibitors |
| JO3089B1 (ar) | 2010-11-19 | 2017-03-15 | H Lundbeck As | مشتقات ايميدازول كمثبطات لانزيمات pde10a |
| US8349824B2 (en) * | 2010-12-07 | 2013-01-08 | Hoffmann-La Roche Inc. | Triazolopyridine compounds |
| WO2012096929A2 (en) | 2011-01-11 | 2012-07-19 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| US9540379B2 (en) * | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| US8772316B2 (en) | 2011-02-18 | 2014-07-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinolinol derivatives as inhibitors of phosphodiesterase 10 (PDE10A) |
| WO2013005798A1 (ja) * | 2011-07-06 | 2013-01-10 | 持田製薬株式会社 | 新規含窒素複素環誘導体 |
| WO2013045607A1 (en) | 2011-09-30 | 2013-04-04 | H. Lundbeck A/S | Quinazoline linked heteroaromatic tricycle derivatives as pde10a enzyme inhibitors |
| WO2013050527A1 (en) | 2011-10-05 | 2013-04-11 | H. Lundbeck A/S | Quinazoline derivatives as pde10a enzyme inhibitors |
| TWI570124B (zh) * | 2011-12-21 | 2017-02-11 | Ｈ 朗德貝克公司 | 作為ｐｄｅ１０ａ酵素抑制劑的喹啉衍生物 |
| WO2013127817A1 (en) | 2012-02-27 | 2013-09-06 | H. Lundbeck A/S | Imidazole derivatives as pde10a enzyme inhibitors |
| SG11201406890YA (en) | 2012-05-30 | 2014-11-27 | Hoffmann La Roche | Triazolo compounds as pde10 inhibitors |
| US9505751B2 (en) * | 2012-06-19 | 2016-11-29 | Sunovion Pharmaceuticals Inc. | Substituted [1,2,4]triazolo[1,5-a]pyrazines as phosphodiesterase inhibitors |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US9556179B2 (en) | 2012-12-21 | 2017-01-31 | Bristol-Myers Squibb Company | Substituted imidazoles as casein kinase 1 D/E inhibitors |
| CA2902781C (en) * | 2013-02-27 | 2020-12-29 | Mochida Pharmaceutical Co., Ltd. | Novel pyrazole derivative |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| PL3597649T3 (pl) | 2014-04-23 | 2022-04-04 | Dart Neuroscience Llc | Kompozycje zawierające podstawione związki [1,2,4]triazolo[1,5-a]pirymidyn-7-ylowe jako inhibitory pde2 |
| NZ630810A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ630803A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| PL408251A1 (pl) * | 2014-05-19 | 2015-11-23 | Celon Pharma Spółka Z Ograniczoną Odpowiedzialnością | Skondensowane pochodne triazolu jako inhibitory fosfodiesterazy 10A |
| WO2016073424A1 (en) * | 2014-11-05 | 2016-05-12 | Dart Neuroscience, Llc | Substituted 5-methyl-[1, 2, 4] triazolo [1,5-a) pyrimidin-2-amine compounds as pde2 inhibitors |
| US9879002B2 (en) | 2015-04-24 | 2018-01-30 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| JP2018535969A (ja) | 2015-11-04 | 2018-12-06 | オメロス コーポレーション | Ｐｄｅ１０阻害剤の固体状態形態 |
| WO2020094590A1 (en) | 2018-11-06 | 2020-05-14 | H. Lundbeck A/S | 5,8-dimethyl-2-[2-(1-methyl-4-phenyl-1h-imidazol-2-yl)-ethyl]-[1,2,4]triazolo[1,5-a]pyrazine hemiadipate |
| TW202031250A (zh) | 2018-11-06 | 2020-09-01 | 丹麥商Ｈ 朗德貝克公司 | 用於治療負性症狀和認知損傷之pde10a抑制劑 |
| WO2020094592A1 (en) | 2018-11-06 | 2020-05-14 | H. Lundbeck A/S | Compounds for treating negative symptoms and cognitive impairments |
| CN111100071A (zh) * | 2019-12-19 | 2020-05-05 | 西安近代化学研究所 | 一种合成2-氰基-5-芳基-1h-咪唑类化合物的方法 |
| CN110981813A (zh) * | 2019-12-19 | 2020-04-10 | 西安近代化学研究所 | 一种2-氰基-5-芳基-1h-咪唑类化合物的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036840A (en) | 1972-06-07 | 1977-07-19 | Icn Pharmaceuticals | 2-Substituted-s-triazolo[1,5a]pyrimidines |
| DE10230605A1 (de) | 2002-07-08 | 2004-01-29 | Bayer Ag | Substituierte Imidazotriazine |
| WO2005003129A1 (en) * | 2003-06-30 | 2005-01-13 | Altana Pharma Ag | Pyrrolodihydroisoquinolines as pde10 inhibitors |
| EP1723134A2 (en) * | 2004-02-18 | 2006-11-22 | Pfizer Products Incorporated | Tetrahydroisoquinolinyl derivatives of quinazoline and isoquinoline |
| WO2005086895A2 (en) | 2004-03-08 | 2005-09-22 | Wyeth | Ion channel modulators |
| US20060183763A1 (en) * | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| NL2000397C2 (nl) | 2006-01-05 | 2007-10-30 | Pfizer Prod Inc | Bicyclische heteroarylverbindingen als PDE10 inhibitoren. |
| JP2009527560A (ja) * | 2006-02-21 | 2009-07-30 | アムゲン インコーポレイティッド | ホスホジエステラーゼ１０阻害剤としてのシンノリン誘導体 |
| WO2008001182A1 (en) | 2006-06-26 | 2008-01-03 | Pfizer Products Inc. | Tricyclic heteroaryl compounds as pde10 inhibitors |
| JP2010533715A (ja) | 2007-07-17 | 2010-10-28 | アムジエン・インコーポレーテツド | 複素環系ｐｋｂ調節剤 |
| BRPI0814939A2 (pt) | 2007-08-10 | 2015-01-27 | Glaxosmithkline Llc | Entidade química, composição farmacêutica, e, método para tratar uma infecção viral em um mamífero. |
| UA102693C2 (ru) | 2008-06-20 | 2013-08-12 | Х. Луннбек А/С | Производные фенилимидазола как ингибиторы фермента pde10a |
| US8133897B2 (en) | 2008-06-20 | 2012-03-13 | H. Lundbeck A/S | Phenylimidazole derivatives as PDE10A enzyme inhibitors |
| TWI501965B (zh) * | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物 |
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2009
- 2009-06-15 TW TW098119876A patent/TWI501965B/zh not_active IP Right Cessation
- 2009-06-19 CN CN200980132027.3A patent/CN102124002B/zh not_active Expired - Fee Related
- 2009-06-19 PT PT97654610T patent/PT2318394E/pt unknown
- 2009-06-19 KR KR1020177002859A patent/KR20170016523A/ko not_active Ceased
- 2009-06-19 JP JP2011513878A patent/JP5930714B2/ja not_active Expired - Fee Related
- 2009-06-19 EP EP09765461.0A patent/EP2318394B1/en active Active
- 2009-06-19 KR KR1020177034302A patent/KR102025487B1/ko not_active Expired - Fee Related
- 2009-06-19 DK DK09765461.0T patent/DK2318394T3/en active
- 2009-06-19 CA CA2728335A patent/CA2728335C/en not_active Expired - Fee Related
- 2009-06-19 WO PCT/DK2009/050134 patent/WO2009152825A1/en not_active Ceased
- 2009-06-19 BR BRPI0915383A patent/BRPI0915383B8/pt not_active IP Right Cessation
- 2009-06-19 KR KR1020107028654A patent/KR101703938B1/ko not_active Expired - Fee Related
- 2009-06-19 NZ NZ589926A patent/NZ589926A/en not_active IP Right Cessation
- 2009-06-19 PL PL09765461T patent/PL2318394T3/pl unknown
- 2009-06-19 RS RS20140135A patent/RS53226B/sr unknown
- 2009-06-19 AU AU2009259209A patent/AU2009259209B2/en not_active Ceased
- 2009-06-19 ES ES09765461.0T patent/ES2456349T3/es active Active
- 2009-06-19 MY MYPI20106011 patent/MY152949A/en unknown
- 2009-06-19 AR ARP090102239A patent/AR072199A1/es active IP Right Grant
- 2009-06-19 EA EA201170061A patent/EA018880B1/ru not_active IP Right Cessation
- 2009-06-19 MX MX2010014136A patent/MX2010014136A/es active IP Right Grant
- 2009-06-19 HR HRP20140232AT patent/HRP20140232T1/hr unknown
- 2009-06-19 SI SI200930879T patent/SI2318394T1/sl unknown
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2010
- 2010-06-17 EA EA201270046A patent/EA021410B1/ru not_active IP Right Cessation
- 2010-06-17 US US13/378,405 patent/US8841297B2/en not_active Expired - Fee Related
- 2010-06-17 RS RS20140700A patent/RS53704B1/sr unknown
- 2010-06-17 CN CN201080037331.2A patent/CN102482262B/zh not_active Expired - Fee Related
- 2010-12-07 IL IL209834A patent/IL209834A/en active IP Right Grant
- 2010-12-17 CL CL2010001467A patent/CL2010001467A1/es unknown
- 2010-12-20 CO CO10159483A patent/CO6321263A2/es active IP Right Grant
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2011
- 2011-01-04 ZA ZA2011/00109A patent/ZA201100109B/en unknown
- 2011-12-16 CL CL2011003205A patent/CL2011003205A1/es unknown
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2014
- 2014-03-28 CY CY20141100233T patent/CY1115001T1/el unknown
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