CA2735549A1 - Substituted triazolo-pyridazine derivatives - Google Patents
Substituted triazolo-pyridazine derivatives Download PDFInfo
- Publication number
- CA2735549A1 CA2735549A1 CA 2735549 CA2735549A CA2735549A1 CA 2735549 A1 CA2735549 A1 CA 2735549A1 CA 2735549 CA2735549 CA 2735549 CA 2735549 A CA2735549 A CA 2735549A CA 2735549 A1 CA2735549 A1 CA 2735549A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- deuterium
- compounds
- composition
- acid
- 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
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- CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 37
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 36
- 229940124597 therapeutic agent Drugs 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 13
- 230000000155 isotopic effect Effects 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
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- 101710085469 CD2 homolog Chemical group 0.000 claims description 2
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- 238000000034 method Methods 0.000 abstract description 25
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical class CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
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- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
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- 229910001961 silver nitrate Inorganic materials 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229960004793 sucrose Drugs 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9329308P | 2008-08-29 | 2008-08-29 | |
| US61/093,293 | 2008-08-29 | ||
| PCT/US2009/055427 WO2010025407A1 (en) | 2008-08-29 | 2009-08-28 | Substituted triazolo-pyridazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2735549A1 true CA2735549A1 (en) | 2010-03-04 |
Family
ID=41721962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2735549 Abandoned CA2735549A1 (en) | 2008-08-29 | 2009-08-28 | Substituted triazolo-pyridazine derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (4) | US8003646B2 (https=) |
| EP (2) | EP2328414B1 (https=) |
| JP (3) | JP5183808B2 (https=) |
| KR (1) | KR20110063479A (https=) |
| CN (2) | CN104098578A (https=) |
| AU (1) | AU2009285533B2 (https=) |
| BR (1) | BRPI0912928A2 (https=) |
| CA (1) | CA2735549A1 (https=) |
| DK (1) | DK2328414T3 (https=) |
| EA (1) | EA020071B1 (https=) |
| ES (1) | ES2451542T3 (https=) |
| HR (1) | HRP20140195T1 (https=) |
| MX (1) | MX2011002278A (https=) |
| PL (1) | PL2328414T3 (https=) |
| PT (1) | PT2328414E (https=) |
| WO (1) | WO2010025407A1 (https=) |
| ZA (1) | ZA201102123B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2735549A1 (en) | 2008-08-29 | 2010-03-04 | Concert Pharmaceuticals, Inc. | Substituted triazolo-pyridazine derivatives |
| EP2340782A4 (en) | 2008-10-03 | 2014-04-02 | Inst Alberto Luiz Coimbra De Pos Graduacao E Pesquisa De Engenharia Coppe Ufrj | METHOD AND DEVICE FOR REMOVING METAL FRAGMENTS AND METAL ELEMENTS FROM TOOTH ROOT CHANNELS |
| US8501738B2 (en) | 2009-06-23 | 2013-08-06 | Concert Pharmaceuticals, Inc. | Substituted triazolo-pyridazine derivatives |
| RU2014120166A (ru) | 2011-10-20 | 2015-11-27 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Замещенные бициклические аза-гетероциклы и их аналоги в качестве модуляторов сиртуина |
| EP2768834B1 (en) * | 2011-10-20 | 2016-04-27 | Glaxosmithkline LLC | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
| EP2802569B1 (de) | 2012-01-11 | 2016-01-06 | Bayer Intellectual Property GmbH | Tetrazol-5-yl- und triazol-5-yl-arylverbindungen und ihre verwendung als herbizide |
| US20150158870A1 (en) * | 2012-05-11 | 2015-06-11 | Concert Pharmaceuticals Inc. | Polymorphs of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| EP2847195A1 (en) * | 2012-05-11 | 2015-03-18 | Concert Pharmaceuticals Inc. | Form 2 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| US20150099753A1 (en) * | 2012-05-11 | 2015-04-09 | Concert Pharmaceuticals Inc. | Form 5 polymorph of 7-(tert-butyl-d9)-3-(2,5-difluorophenyl)-6-((1-methyl-1h-1,2,4-triazol-5-yl)methoxy)-[1,2,4]triazolo[4,3-b]pyridazine |
| WO2015052173A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | Tetrazole and triazole compounds and their use as herbicides |
| WO2015052178A1 (en) | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
| WO2015095549A1 (en) * | 2013-12-18 | 2015-06-25 | Concert Pharmaceuticals, Inc. | Dosage regimen for gabaa receptor subtype selective drug |
| US10166183B2 (en) | 2014-02-07 | 2019-01-01 | Auspex Pharmaceuticals, Inc. | Pharmaceutical formulations |
| CN104353078B (zh) * | 2014-11-24 | 2017-10-24 | 王寿世 | 一种麻醉用药物组合物 |
| CN104474549A (zh) * | 2014-11-24 | 2015-04-01 | 王寿世 | 异丙酚和gabaa受体拮抗剂在制备麻醉药物中的用途 |
| US10026332B1 (en) | 2017-04-10 | 2018-07-17 | Jasmine Gupta | Method to deliver contextual educational information utilizing smart wearables |
| SG11202109526PA (en) * | 2019-03-18 | 2021-10-28 | Neurocycle Therapeutics Inc | Use of gabaa receptor modulators for treatment of pain |
| WO2023205722A1 (en) * | 2022-04-20 | 2023-10-26 | Engrail Therapeutics, Inc. | Gabaa receptor modulator salts, particles, and uses thereof |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9321162D0 (en) | 1993-10-13 | 1993-12-01 | Boots Co Plc | Therapeutic agents |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| CN1087725C (zh) | 1994-03-25 | 2002-07-17 | 同位素技术有限公司 | 用氘代方法增强药物效果 |
| ES2194205T3 (es) * | 1996-07-25 | 2003-11-16 | Merck Sharp & Dohme | Derivados de triazolo-piridazina sustituidos como ligandos para los receptores gaba. |
| YU43800A (sh) * | 1998-01-21 | 2002-12-10 | Merck Sharp & Dohme Limited | Triazolo-piridazin derivati kao ligandi za gaba receptore |
| US6440710B1 (en) | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| JP2002535407A (ja) * | 1999-01-27 | 2002-10-22 | メルク シャープ エンド ドーム リミテッド | Ｇａｂａ受容体のリガンドとしてのトリアゾロピリダジン誘導体 |
| PT1104760E (pt) | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
| US20020165217A1 (en) * | 2001-05-01 | 2002-11-07 | Pfizer Inc. | Combination treatment for anxiety and depression |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| DE60315876T2 (de) * | 2002-11-28 | 2008-05-21 | Neurosearch A/S | Verfahren zum screening für verbindungen mit sedativer oder anxiolytischer potenz |
| WO2006061428A2 (en) | 2004-12-10 | 2006-06-15 | Universität Zürich | Gaba-a alpha 2 and alpha 3 receptor agonists for treating neuropathic, inflammatory and migraine associated pain |
| CN101309917B (zh) | 2005-10-06 | 2013-09-11 | 奥斯拜客斯制药有限公司 | 具有增强治疗性质的胃h+，k+-atp酶氘代抑制剂 |
| US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| US20080051422A1 (en) * | 2006-08-22 | 2008-02-28 | Concert Pharmaceuticals Inc. | 4-Aminoquinazoline derivatives and methods of use thereof |
| WO2008030382A1 (en) | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| US20080242687A1 (en) * | 2007-04-02 | 2008-10-02 | Auspex Pharmaceuticals, Inc. | Substituted pyrimidines |
| CA2735549A1 (en) | 2008-08-29 | 2010-03-04 | Concert Pharmaceuticals, Inc. | Substituted triazolo-pyridazine derivatives |
-
2009
- 2009-08-28 CA CA 2735549 patent/CA2735549A1/en not_active Abandoned
- 2009-08-28 MX MX2011002278A patent/MX2011002278A/es active IP Right Grant
- 2009-08-28 HR HRP20140195AT patent/HRP20140195T1/hr unknown
- 2009-08-28 US US12/550,346 patent/US8003646B2/en active Active
- 2009-08-28 PT PT98106859T patent/PT2328414E/pt unknown
- 2009-08-28 AU AU2009285533A patent/AU2009285533B2/en not_active Ceased
- 2009-08-28 DK DK09810685.9T patent/DK2328414T3/en active
- 2009-08-28 BR BRPI0912928-6A patent/BRPI0912928A2/pt not_active IP Right Cessation
- 2009-08-28 CN CN201410346402.7A patent/CN104098578A/zh active Pending
- 2009-08-28 KR KR20117006632A patent/KR20110063479A/ko not_active Ceased
- 2009-08-28 EP EP20090810685 patent/EP2328414B1/en active Active
- 2009-08-28 EA EA201100409A patent/EA020071B1/ru not_active IP Right Cessation
- 2009-08-28 WO PCT/US2009/055427 patent/WO2010025407A1/en not_active Ceased
- 2009-08-28 CN CN200980140350.5A patent/CN102176826B/zh not_active Expired - Fee Related
- 2009-08-28 PL PL09810685T patent/PL2328414T3/pl unknown
- 2009-08-28 JP JP2011525250A patent/JP5183808B2/ja not_active Expired - Fee Related
- 2009-08-28 ES ES09810685T patent/ES2451542T3/es active Active
- 2009-08-28 EP EP20130196185 patent/EP2716158A1/en not_active Withdrawn
-
2011
- 2011-03-22 ZA ZA2011/02123A patent/ZA201102123B/en unknown
- 2011-06-30 US US13/174,662 patent/US8399467B2/en active Active
-
2013
- 2013-01-15 JP JP2013004449A patent/JP5373982B2/ja not_active Expired - Fee Related
- 2013-03-18 US US13/846,119 patent/US8921366B2/en active Active
- 2013-09-19 JP JP2013194060A patent/JP2014058518A/ja active Pending
-
2014
- 2014-12-23 US US14/581,843 patent/US20150111895A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140827 |
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| FZDE | Discontinued |
Effective date: 20170104 |