JP2012522056A5 - - Google Patents
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- Publication number
- JP2012522056A5 JP2012522056A5 JP2012503544A JP2012503544A JP2012522056A5 JP 2012522056 A5 JP2012522056 A5 JP 2012522056A5 JP 2012503544 A JP2012503544 A JP 2012503544A JP 2012503544 A JP2012503544 A JP 2012503544A JP 2012522056 A5 JP2012522056 A5 JP 2012522056A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- imidazol
- pyrrolidinyl
- hydrogen
- methyl
- 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.)
- Granted
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- 125000000217 alkyl group Chemical group 0.000 claims 33
- -1 —NR a R b Chemical group 0.000 claims 30
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000001424 substituent group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 2
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims 2
- 108020005544 Antisense RNA Proteins 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 102000000588 Interleukin-2 Human genes 0.000 claims 2
- 108010002350 Interleukin-2 Proteins 0.000 claims 2
- 102000004889 Interleukin-6 Human genes 0.000 claims 2
- 108090001005 Interleukin-6 Proteins 0.000 claims 2
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000005867 T cell response Effects 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims 2
- 229960003805 amantadine Drugs 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003184 complementary RNA Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 210000002443 helper t lymphocyte Anatomy 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims 2
- 229960002751 imiquimod Drugs 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims 2
- 230000002452 interceptive effect Effects 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 229940100601 interleukin-6 Drugs 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 229960000329 ribavirin Drugs 0.000 claims 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 2
- 229960000888 rimantadine Drugs 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- UMPWFNPLHSVRAN-UHFFFAOYSA-N 2-(diethylamino)-2-phenylacetaldehyde Chemical compound CCN(CC)C(C=O)C1=CC=CC=C1 UMPWFNPLHSVRAN-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 102000013462 Interleukin-12 Human genes 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 102000015696 Interleukins Human genes 0.000 claims 1
- 108010063738 Interleukins Proteins 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 229940117681 interleukin-12 Drugs 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CC(*C1C2)C1N(*)C2C1=NC=C*1 Chemical compound CC(*C1C2)C1N(*)C2C1=NC=C*1 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16457909P | 2009-03-30 | 2009-03-30 | |
| US61/164,579 | 2009-03-30 | ||
| PCT/US2010/028999 WO2010117704A1 (en) | 2009-03-30 | 2010-03-29 | Hepatitis c virus inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012522056A JP2012522056A (ja) | 2012-09-20 |
| JP2012522056A5 true JP2012522056A5 (https=) | 2013-04-25 |
| JP5612661B2 JP5612661B2 (ja) | 2014-10-22 |
Family
ID=42313493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012503544A Expired - Fee Related JP5612661B2 (ja) | 2009-03-30 | 2010-03-29 | Ｃ型肝炎ウイルス阻害剤 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20100249190A1 (https=) |
| EP (1) | EP2414352B1 (https=) |
| JP (1) | JP5612661B2 (https=) |
| KR (1) | KR20110134497A (https=) |
| CN (1) | CN102378762B (https=) |
| AR (1) | AR076170A1 (https=) |
| AU (1) | AU2010234861A1 (https=) |
| BR (1) | BRPI1014084A2 (https=) |
| CA (1) | CA2758047C (https=) |
| CL (1) | CL2011002453A1 (https=) |
| CO (1) | CO6361922A2 (https=) |
| EA (1) | EA021260B1 (https=) |
| ES (1) | ES2524542T3 (https=) |
| IL (1) | IL214939A0 (https=) |
| MX (1) | MX2011009644A (https=) |
| NZ (1) | NZ594981A (https=) |
| PE (1) | PE20120517A1 (https=) |
| TW (1) | TWI476190B (https=) |
| WO (1) | WO2010117704A1 (https=) |
| ZA (1) | ZA201106669B (https=) |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3020187B2 (ja) | 1992-02-19 | 2000-03-15 | 三谷セキサン株式会社 | 埋込み杭工法及びコンクリート杭 |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| CA2740193A1 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| EP2367823A1 (en) | 2008-12-23 | 2011-09-28 | Abbott Laboratories | Anti-viral compounds |
| US8314135B2 (en) | 2009-02-09 | 2012-11-20 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole antivirals |
| TWI438200B (zh) * | 2009-02-17 | 2014-05-21 | 必治妥美雅史谷比公司 | Ｃ型肝炎病毒抑制劑 |
| US8242156B2 (en) | 2009-02-17 | 2012-08-14 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8188132B2 (en) | 2009-02-17 | 2012-05-29 | Enanta Pharmaceuticals, Inc. | Linked dibenzimidazole derivatives |
| US8394968B2 (en) | 2009-02-17 | 2013-03-12 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8101643B2 (en) | 2009-02-27 | 2012-01-24 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US9765087B2 (en) | 2009-02-27 | 2017-09-19 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
| US8673954B2 (en) | 2009-02-27 | 2014-03-18 | Enanta Pharmaceuticals, Inc. | Benzimidazole derivatives |
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| CN102459165B (zh) * | 2009-04-15 | 2015-09-02 | Abbvie公司 | 抗病毒化合物 |
| PT3309157T (pt) | 2009-05-13 | 2019-12-02 | Gilead Pharmasset Llc | Compostos antivirais |
| US8138215B2 (en) | 2009-05-29 | 2012-03-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8211928B2 (en) | 2009-05-29 | 2012-07-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| UA118080C2 (uk) * | 2009-06-11 | 2018-11-26 | Еббві Айрленд Анлімітед Компані | Противірусні сполуки |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8221737B2 (en) | 2009-06-16 | 2012-07-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| US8609648B2 (en) | 2009-07-02 | 2013-12-17 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
| IN2012DN00999A (https=) | 2009-07-16 | 2015-04-10 | Vertex Pharma | |
| EA201290089A1 (ru) | 2009-09-04 | 2012-09-28 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Химические соединения |
| WO2011031904A1 (en) | 2009-09-11 | 2011-03-17 | Enanta Pharmaceuticals, Inc | Hepatitis c virus inhibitors |
| US8815928B2 (en) | 2009-09-11 | 2014-08-26 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
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| US20110269956A1 (en) | 2009-11-11 | 2011-11-03 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
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| MA34013B1 (fr) | 2010-01-25 | 2013-02-01 | Enanta Pharm Inc | Inhibiteurs du virus de l'hépatite c |
| US8933110B2 (en) | 2010-01-25 | 2015-01-13 | Enanta Pharmaceuticals, Inc. | Hepatitis C virus inhibitors |
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| US8178531B2 (en) | 2010-02-23 | 2012-05-15 | Enanta Pharmaceuticals, Inc. | Antiviral agents |
| KR20120124495A (ko) | 2010-03-04 | 2012-11-13 | 이난타 파마슈티칼스, 인코포레이티드 | Ｈｃｖ 복제의 억제제로서의 조합 제약 작용제 |
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| RU2452735C1 (ru) * | 2010-11-30 | 2012-06-10 | Александр Васильевич Иващенко | Замещенные азолы, противовирусный активный компонент, фармацевтическая композиция, способ получения и применения |
| EP2651928A4 (en) * | 2010-12-15 | 2014-06-18 | Abbvie Inc | ANTI-VIRAL COMPOUNDS |
| MX2013006951A (es) * | 2010-12-16 | 2013-10-03 | Abbvie Inc | Compuestos antivirales. |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| US8552047B2 (en) | 2011-02-07 | 2013-10-08 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9546160B2 (en) | 2011-05-12 | 2017-01-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| WO2012158861A2 (en) | 2011-05-18 | 2012-11-22 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 5-azaspiro[2.4]heptane-6-carboxylic acid and its derivatives |
| KR101931311B1 (ko) * | 2011-05-27 | 2018-12-20 | 아칠리온 파르마세우티칼스 인코포레이티드 | Ｈｃｖ 감염 치료에 유용한 치환된 앨리팬, 시클로팬, 헤테라팬, 헤테로팬, 헤테로-헤테라팬 및 메탈로센 |
| WO2013016499A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Methods for preparation of thiophene compounds |
| WO2013016492A1 (en) | 2011-07-26 | 2013-01-31 | Vertex Pharmaceuticals Incorporated | Thiophene compounds |
| PL2709613T5 (pl) | 2011-09-16 | 2020-12-14 | Gilead Pharmasset Llc | Metody leczenia hcv |
| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US9326973B2 (en) | 2012-01-13 | 2016-05-03 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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| MD596Z (ro) * | 2012-10-09 | 2013-09-30 | Национальный Центр Общественного Здоровья Министерства Здравоохранения Республики Молдова | Metodă de tratament al hepatitei virale cronice C la copii |
| PT2950786T (pt) | 2013-01-31 | 2020-03-03 | Gilead Pharmasset Llc | Formulação de combinação de dois compostos antivirais |
| US20150065439A1 (en) | 2013-02-28 | 2015-03-05 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| US9717712B2 (en) | 2013-07-02 | 2017-08-01 | Bristol-Myers Squibb Company | Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus |
| US20150023913A1 (en) | 2013-07-02 | 2015-01-22 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| US9775831B2 (en) | 2013-07-17 | 2017-10-03 | Bristol-Myers Squibb Company | Combinations comprising biphenyl derivatives for use in the treatment of HCV |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
| US10617675B2 (en) | 2015-08-06 | 2020-04-14 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| KR20180115743A (ko) * | 2016-02-26 | 2018-10-23 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 신규 독소, 및 이의 중간체를 제조하는 방법 |
| CN107987083A (zh) * | 2017-11-24 | 2018-05-04 | 江苏亚盛医药开发有限公司 | 用于治疗和/或预防与肝炎病毒相关的疾病或病症的双二氮杂双环化合物 |
| CA3219397A1 (en) | 2021-05-21 | 2022-11-24 | Gilead Sciences, Inc. | Tetracyclic compounds for the treatment of zika virus infection |
| CA3220903A1 (en) | 2021-05-21 | 2022-11-24 | Gilead Sciences, Inc. | Pentacyclic derivatives as zika virus inhibitors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5654451B1 (en) * | 1993-01-14 | 2000-02-22 | Magainin Pharma | Amino acids and peptides having modified c-terminals and modified n-terminals |
| WO2006093867A1 (en) * | 2005-02-28 | 2006-09-08 | The Rockefeller University | Structure of the hepatitits c virus ns5a protein |
| US7659270B2 (en) * | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8329159B2 (en) * | 2006-08-11 | 2012-12-11 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7759495B2 (en) * | 2006-08-11 | 2010-07-20 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US20100158862A1 (en) * | 2006-08-11 | 2010-06-24 | Bristol-Myers Squibb Company | Hepatitis C Virus Inhibitors |
| WO2010065668A1 (en) * | 2008-12-03 | 2010-06-10 | Presidio Pharmaceuticals, Inc. | Inhibitors of hcv ns5a |
| UA118080C2 (uk) * | 2009-06-11 | 2018-11-26 | Еббві Айрленд Анлімітед Компані | Противірусні сполуки |
-
2010
- 2010-03-24 TW TW099108734A patent/TWI476190B/zh not_active IP Right Cessation
- 2010-03-25 US US12/731,935 patent/US20100249190A1/en not_active Abandoned
- 2010-03-29 PE PE2011001733A patent/PE20120517A1/es not_active Application Discontinuation
- 2010-03-29 KR KR1020117025610A patent/KR20110134497A/ko not_active Ceased
- 2010-03-29 JP JP2012503544A patent/JP5612661B2/ja not_active Expired - Fee Related
- 2010-03-29 BR BRPI1014084A patent/BRPI1014084A2/pt not_active IP Right Cessation
- 2010-03-29 CN CN201080015321.9A patent/CN102378762B/zh not_active Expired - Fee Related
- 2010-03-29 MX MX2011009644A patent/MX2011009644A/es active IP Right Grant
- 2010-03-29 NZ NZ594981A patent/NZ594981A/xx not_active IP Right Cessation
- 2010-03-29 EA EA201101240A patent/EA021260B1/ru not_active IP Right Cessation
- 2010-03-29 EP EP10714721.7A patent/EP2414352B1/en not_active Not-in-force
- 2010-03-29 CA CA2758047A patent/CA2758047C/en not_active Expired - Fee Related
- 2010-03-29 ES ES10714721.7T patent/ES2524542T3/es active Active
- 2010-03-29 AU AU2010234861A patent/AU2010234861A1/en not_active Abandoned
- 2010-03-29 WO PCT/US2010/028999 patent/WO2010117704A1/en not_active Ceased
- 2010-03-30 AR ARP100101039A patent/AR076170A1/es unknown
-
2011
- 2011-09-01 IL IL214939A patent/IL214939A0/en unknown
- 2011-09-12 ZA ZA2011/06669A patent/ZA201106669B/en unknown
- 2011-09-27 CO CO11126484A patent/CO6361922A2/es active IP Right Grant
- 2011-09-30 CL CL2011002453A patent/CL2011002453A1/es unknown
-
2012
- 2012-07-13 US US13/548,298 patent/US8822444B2/en active Active
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