JP2013522368A5 - - Google Patents
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- JP2013522368A5 JP2013522368A5 JP2013501397A JP2013501397A JP2013522368A5 JP 2013522368 A5 JP2013522368 A5 JP 2013522368A5 JP 2013501397 A JP2013501397 A JP 2013501397A JP 2013501397 A JP2013501397 A JP 2013501397A JP 2013522368 A5 JP2013522368 A5 JP 2013522368A5
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- JP
- Japan
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- Prior art date
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 10
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 206010013663 drug dependence Diseases 0.000 claims description 7
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
- 239000012634 fragment Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- -1 —OH Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 3
- 108090000137 Opioid Receptors Proteins 0.000 claims description 3
- 102000003840 Opioid Receptors Human genes 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 229960003920 cocaine Drugs 0.000 claims description 3
- 229960002069 diamorphine Drugs 0.000 claims description 3
- 229960002715 nicotine Drugs 0.000 claims description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 208000022497 Cocaine-Related disease Diseases 0.000 claims description 2
- 208000003698 Heroin Dependence Diseases 0.000 claims description 2
- 208000004454 Hyperalgesia Diseases 0.000 claims description 2
- 208000035154 Hyperesthesia Diseases 0.000 claims description 2
- 206010057852 Nicotine dependence Diseases 0.000 claims description 2
- 208000003251 Pruritus Diseases 0.000 claims description 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 2
- 201000006145 cocaine dependence Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 claims 1
- 206010038678 Respiratory depression Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 230000007803 itching Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 0 **(C=C(*)C=C1)C=C1c1ccc(*)cc1 Chemical compound **(C=C(*)C=C1)C=C1c1ccc(*)cc1 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 description 1
- 241001535291 Analges Species 0.000 description 1
- DREJORWPJIOPST-UHFFFAOYSA-N CC(C)C1N(C)NNNN1 Chemical compound CC(C)C1N(C)NNNN1 DREJORWPJIOPST-UHFFFAOYSA-N 0.000 description 1
- DRYSRBROYABEJA-UHFFFAOYSA-N CC(NN)NN(C)NC Chemical compound CC(NN)NN(C)NC DRYSRBROYABEJA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000003793 antidiarrheal agent Substances 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000003434 antitussive agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 108700023159 delta Opioid Receptors Proteins 0.000 description 1
- 102000048124 delta Opioid Receptors Human genes 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- INAXVFBXDYWQFN-XHSDSOJGSA-N morphinan Chemical class C1C2=CC=CC=C2[C@]23CCCC[C@H]3[C@@H]1NCC2 INAXVFBXDYWQFN-XHSDSOJGSA-N 0.000 description 1
- 102000051367 mu Opioid Receptors Human genes 0.000 description 1
- 229940127240 opiate Drugs 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 108020001612 μ-opioid receptors Proteins 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31617510P | 2010-03-22 | 2010-03-22 | |
| US61/316,175 | 2010-03-22 | ||
| US39414810P | 2010-10-18 | 2010-10-18 | |
| US61/394,148 | 2010-10-18 | ||
| US42191510P | 2010-12-10 | 2010-12-10 | |
| US61/421,915 | 2010-12-10 | ||
| PCT/US2011/029425 WO2011119605A2 (en) | 2010-03-22 | 2011-03-22 | Carboxamide biosiosteres of opiates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016078368A Division JP2016175910A (ja) | 2010-03-22 | 2016-04-08 | オピオイド受容体リガンドとしてのカルボキサミド基を含有するモルヒネ誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013522368A JP2013522368A (ja) | 2013-06-13 |
| JP2013522368A5 true JP2013522368A5 (enExample) | 2014-05-08 |
| JP5964809B2 JP5964809B2 (ja) | 2016-08-03 |
Family
ID=44072680
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501397A Active JP5964809B2 (ja) | 2010-03-22 | 2011-03-22 | オピオイド受容体リガンドとしてのカルボキサミド基を含有するモルヒネ誘導体 |
| JP2016078368A Pending JP2016175910A (ja) | 2010-03-22 | 2016-04-08 | オピオイド受容体リガンドとしてのカルボキサミド基を含有するモルヒネ誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016078368A Pending JP2016175910A (ja) | 2010-03-22 | 2016-04-08 | オピオイド受容体リガンドとしてのカルボキサミド基を含有するモルヒネ誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (4) | US8436175B2 (enExample) |
| EP (1) | EP2550253B9 (enExample) |
| JP (2) | JP5964809B2 (enExample) |
| AU (1) | AU2011232628B2 (enExample) |
| CA (1) | CA2793725C (enExample) |
| ES (1) | ES2582306T3 (enExample) |
| WO (1) | WO2011119605A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7557119B2 (en) * | 2005-07-21 | 2009-07-07 | Rensselaer Polytechnic Institute | Large substituent, non-phenolic opioids |
| LT2506712T (lt) | 2009-12-04 | 2019-06-25 | Alkermes Pharma Ireland Limited | Morfinano dariniai, skirti narkotinių medžiagų perdozavimo gydymui |
| CA2793725C (en) | 2010-03-22 | 2018-05-01 | Rensselaer Polytechnic Institute | Carboxamide bioisosteres of opiates |
| PL3446565T3 (pl) | 2010-08-23 | 2024-04-02 | Alkermes Pharma Ireland Limited | Sposoby leczenia przyrostu masy ciała wywołanego lekami przeciwpsychotycznymi |
| PT2725908T (pt) * | 2011-06-29 | 2017-08-31 | Alkermes Inc | Compostos opioides de ação periférica |
| US9211293B2 (en) | 2011-12-15 | 2015-12-15 | Alkermes Pharma Ireland Limited | Opioid agonist antagonist combinations |
| US9656961B2 (en) | 2013-05-24 | 2017-05-23 | Alkermes Pharma Ireland Limited | Methods for treating depressive symptoms |
| WO2014190270A1 (en) | 2013-05-24 | 2014-11-27 | Alkermes Pharma Ireland Limited | Morphan and morphinan analogues, and methods of use |
| CN103992272B (zh) * | 2014-06-09 | 2016-05-11 | 安徽省逸欣铭医药科技有限公司 | 一种盐酸喷他佐辛酯、其制备方法及其用途 |
| WO2022101444A1 (en) | 2020-11-12 | 2022-05-19 | Alkermes Pharma Ireland Limited | Immediate release multilayer tablet |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB874217A (en) | 1958-10-30 | 1961-08-02 | Albert Boehringer | Normorphine derivatives |
| CH581624A5 (enExample) | 1970-08-14 | 1976-11-15 | Sumitomo Chemical Co | |
| US3856795A (en) * | 1972-04-25 | 1974-12-24 | American Home Prod | Process for preparation of secondary amines from tertiary amines |
| DE2254298A1 (de) | 1972-11-06 | 1974-05-16 | Boehringer Sohn Ingelheim | Neue (heteroarylmethyl)-normorphine, deren saeureadditionssalze, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| US4032529A (en) * | 1974-09-20 | 1977-06-28 | Sterling Drug Inc. | Aminomethanobenzazocine intermediates |
| US3957793A (en) * | 1974-09-20 | 1976-05-18 | Sterling Drug Inc. | Hydroxyiminobenzazocines |
| US4205171A (en) * | 1976-01-12 | 1980-05-27 | Sterling Drug Inc. | Aminomethanobenzazocines and nitromethanobenzazocines |
| US4176186A (en) * | 1978-07-28 | 1979-11-27 | Boehringer Ingelheim Gmbh | Quaternary derivatives of noroxymorphone which relieve intestinal immobility |
| US4373139A (en) * | 1979-04-30 | 1983-02-08 | Motorola, Inc. | Detectors |
| FR2514644A1 (fr) * | 1981-10-19 | 1983-04-22 | Sanofi Sa | Composition pharmaceutique a action antagoniste peripherique des opiaces |
| US4374139A (en) | 1981-11-09 | 1983-02-15 | Hoffmann-La Roche Inc. | Levorotatory N-substituted acylmorphinans useful as analgesic agents |
| US4649200A (en) * | 1986-05-08 | 1987-03-10 | Regents Of The University Of Minnesota | Substituted pyrroles with opioid receptor activity |
| US4939264A (en) | 1986-07-14 | 1990-07-03 | Abbott Laboratories | Immunoassay for opiate alkaloids and their metabolites; tracers, immunogens and antibodies |
| US4929622A (en) * | 1987-09-24 | 1990-05-29 | Hoechst-Roussel Pharmaceuticals, Inc. | 2,6-Methanopyrrolo-3-benzazocines |
| US5258386A (en) * | 1991-06-05 | 1993-11-02 | The United States Of America As Represented By The Secretary Of The Army | (+)-3-substituted-N alkylmorphinans, synthesis and use as anticonvulsant and neuroprotective agents |
| US5607941A (en) * | 1992-06-26 | 1997-03-04 | Boehringer Ingelheim Kg | Useful for treating neurodegenerative diseases |
| SE9103745D0 (sv) | 1991-12-18 | 1991-12-18 | Wikstroem Haakan | Aryl-triflates and related compounds |
| EP0632041A1 (en) | 1993-07-01 | 1995-01-04 | Katholieke Universiteit Nijmegen | New morphine derivatives having improved analgesic and narcotic properties |
| ES2188888T3 (es) | 1996-01-10 | 2003-07-01 | Glaxosmithkline Spa | Derivados morfinoides 8ii) con condensados con heterociclos. |
| ES2121553B1 (es) | 1996-12-23 | 1999-06-16 | Univ Santiago Compostela | Nuevos endoperoxidos morfinicos funcionalizados en posiciones c-6 y c-14 del anillo c y procedimiento para su obtencion. |
| GB9709972D0 (en) | 1997-05-19 | 1997-07-09 | Pfizer Ltd | Tetrazoles |
| GB9912411D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| AU6635800A (en) | 1999-08-13 | 2001-03-13 | Southern Research Institute | Pyridomorphinans, thienomoprhinans and use thereof |
| JP2003528819A (ja) | 1999-11-29 | 2003-09-30 | アドラー コーポレーション | オピオイドおよびそのアンタゴニストに関する新規方法および組成物 |
| DE60133584T2 (de) * | 2000-10-31 | 2009-06-04 | Rensselaer Polytechnic Institute | 4-arylpiperidine als opioidrezeptorbindende agenzien |
| US7375082B2 (en) * | 2002-02-22 | 2008-05-20 | Shire Llc | Abuse-resistant hydrocodone compounds |
| WO2003101963A1 (en) | 2002-05-30 | 2003-12-11 | Eli Lilly And Company | Opioid receptor antagonists |
| DE10228103A1 (de) | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE10229842A1 (de) | 2002-07-03 | 2004-02-05 | Helmut Prof. Dr. Schmidhammer | Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung |
| AU2003281060A1 (en) | 2002-07-16 | 2004-02-02 | Rensselaer Polytechnic Institute | Process for conversion of phenols to carboxamides via the succinimide esters |
| AU2003298691A1 (en) | 2002-11-18 | 2004-06-15 | The Mclean Hospital Corporation | Mixed kappa/mu opioids and uses thereof |
| RU2346996C2 (ru) | 2004-06-29 | 2009-02-20 | ЮРОПИЭН НИКЕЛЬ ПиЭлСи | Усовершенствованное выщелачивание основных металлов |
| SI2251330T1 (sl) | 2004-11-05 | 2012-09-28 | Rensselaer Polytech Inst | 4-hidroksibenzomorfani |
| EP1820795A4 (en) * | 2004-12-07 | 2010-10-20 | Toyama Chemical Co Ltd | NEW ANTHRANILIC ACID DERIVATIVE OR SALT FROM IT |
| JP5241484B2 (ja) | 2005-03-07 | 2013-07-17 | ザ ユニヴァーシティー オヴ シカゴ | 内皮細胞増殖及び内皮細胞遊走を減弱するためのオピオイドアンタゴニストの使用 |
| CA2613122C (en) | 2005-06-29 | 2013-01-22 | Compumedics Limited | Sensor assembly with conductive bridge |
| US7557119B2 (en) * | 2005-07-21 | 2009-07-07 | Rensselaer Polytechnic Institute | Large substituent, non-phenolic opioids |
| EP1928881A2 (en) | 2005-08-19 | 2008-06-11 | Pharmacofore, Inc. | Prodrugs of active agents |
| TW200801513A (en) | 2006-06-29 | 2008-01-01 | Fermiscan Australia Pty Ltd | Improved process |
| CA2686851A1 (en) | 2007-05-16 | 2008-11-27 | Rensselaer Polytechnic Institute | Fused-ring heterocycle opioids |
| CN101827819B (zh) * | 2007-08-09 | 2013-06-12 | 伦斯勒理工学院 | 阿片样物质酰胺季铵盐 |
| WO2010000020A1 (en) | 2008-06-30 | 2010-01-07 | Cathrx Ltd | A catheter |
| ES2534055T3 (es) * | 2008-07-21 | 2015-04-16 | Rensselaer Polytechnic Institute | Opioides de amina no fenólicos con sustituyentes de gran tamaño |
| WO2011000020A1 (en) | 2009-06-12 | 2011-01-06 | Sbc Research Pty Ltd | Enhanced method of detection |
| CA2793725C (en) | 2010-03-22 | 2018-05-01 | Rensselaer Polytechnic Institute | Carboxamide bioisosteres of opiates |
-
2011
- 2011-03-22 CA CA2793725A patent/CA2793725C/en active Active
- 2011-03-22 WO PCT/US2011/029425 patent/WO2011119605A2/en not_active Ceased
- 2011-03-22 US US13/069,104 patent/US8436175B2/en active Active
- 2011-03-22 ES ES11715100.1T patent/ES2582306T3/es active Active
- 2011-03-22 EP EP11715100.1A patent/EP2550253B9/en active Active
- 2011-03-22 AU AU2011232628A patent/AU2011232628B2/en active Active
- 2011-03-22 JP JP2013501397A patent/JP5964809B2/ja active Active
-
2013
- 2013-04-05 US US13/857,588 patent/US8716306B2/en active Active
-
2014
- 2014-03-12 US US14/206,170 patent/US8957085B2/en active Active
-
2015
- 2015-01-05 US US14/589,164 patent/US9422301B2/en active Active
-
2016
- 2016-04-08 JP JP2016078368A patent/JP2016175910A/ja active Pending
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