JP2014514308A5 - - Google Patents
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- JP2014514308A5 JP2014514308A5 JP2014505381A JP2014505381A JP2014514308A5 JP 2014514308 A5 JP2014514308 A5 JP 2014514308A5 JP 2014505381 A JP2014505381 A JP 2014505381A JP 2014505381 A JP2014505381 A JP 2014505381A JP 2014514308 A5 JP2014514308 A5 JP 2014514308A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently
- alkynyl
- alkenyl
- substituted
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 31
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 29
- 150000001721 carbon Chemical group 0.000 claims description 28
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 24
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 24
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 24
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 18
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
- 229940035893 uracil Drugs 0.000 claims description 12
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 229940104302 cytosine Drugs 0.000 claims description 10
- 239000002777 nucleoside Substances 0.000 claims description 10
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 8
- 230000003612 virological effect Effects 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- -1 R 8 is H Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 5
- 229940122806 Cyclophilin inhibitor Drugs 0.000 claims description 5
- 241000711549 Hepacivirus C Species 0.000 claims description 5
- 102000014150 Interferons Human genes 0.000 claims description 5
- 108010050904 Interferons Proteins 0.000 claims description 5
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 5
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 5
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class 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 description 5
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 5
- 239000000134 cyclophilin inhibitor Substances 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 229940079322 interferon Drugs 0.000 claims description 5
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- DKSVBVKHUICELN-UHFFFAOYSA-N 3-ethoxy-6-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]-1,2-benzoxazole Chemical compound C=1C=C2C(OCC)=NOC2=CC=1OCCC(CC1)CCN1C1=CC=C(C)N=N1 DKSVBVKHUICELN-UHFFFAOYSA-N 0.000 claims description 4
- 229940123424 Neuraminidase inhibitor Drugs 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 229940125400 channel inhibitor Drugs 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- KQOXLKOJHVFTRN-UHFFFAOYSA-N pleconaril Chemical compound O1N=C(C)C=C1CCCOC1=C(C)C=C(C=2N=C(ON=2)C(F)(F)F)C=C1C KQOXLKOJHVFTRN-UHFFFAOYSA-N 0.000 claims description 4
- 229960000471 pleconaril Drugs 0.000 claims description 4
- 239000002911 sialidase inhibitor Substances 0.000 claims description 4
- 229940113082 thymine Drugs 0.000 claims description 4
- 241000710780 Bovine viral diarrhea virus 1 Species 0.000 claims description 3
- 241000725619 Dengue virus Species 0.000 claims description 3
- 241000710781 Flaviviridae Species 0.000 claims description 3
- 241000710842 Japanese encephalitis virus Species 0.000 claims description 3
- 241000710912 Kunjin virus Species 0.000 claims description 3
- 241000710908 Murray Valley encephalitis virus Species 0.000 claims description 3
- 241000725177 Omsk hemorrhagic fever virus Species 0.000 claims description 3
- 241000710888 St. Louis encephalitis virus Species 0.000 claims description 3
- 241000710771 Tick-borne encephalitis virus Species 0.000 claims description 3
- 241000710886 West Nile virus Species 0.000 claims description 3
- 241000710772 Yellow fever virus Species 0.000 claims description 3
- 208000020329 Zika virus infectious disease Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 229940051021 yellow-fever virus Drugs 0.000 claims description 3
- UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 claims description 2
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical compound IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-N 0.000 claims description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 2
- QNRRHYPPQFELSF-CNYIRLTGSA-N Laninamivir Chemical compound OC[C@@H](O)[C@@H](OC)[C@@H]1OC(C(O)=O)=C[C@H](N=C(N)N)[C@H]1NC(C)=O QNRRHYPPQFELSF-CNYIRLTGSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003805 amantadine Drugs 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229950004244 laninamivir Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical group CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 claims description 2
- 229960003752 oseltamivir Drugs 0.000 claims description 2
- XRQDFNLINLXZLB-CKIKVBCHSA-N peramivir Chemical compound CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N XRQDFNLINLXZLB-CKIKVBCHSA-N 0.000 claims description 2
- 229960001084 peramivir Drugs 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229960000888 rimantadine Drugs 0.000 claims description 2
- 229960001028 zanamivir Drugs 0.000 claims description 2
- ARAIBEBZBOPLMB-UFGQHTETSA-N zanamivir Chemical compound CC(=O)N[C@@H]1[C@@H](N=C(N)N)C=C(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO ARAIBEBZBOPLMB-UFGQHTETSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 241000124008 Mammalia Species 0.000 description 3
- 229910019946 S-S Inorganic materials 0.000 description 3
- 229910019939 S—S Inorganic materials 0.000 description 3
- 241000711557 Hepacivirus Species 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161474848P | 2011-04-13 | 2011-04-13 | |
| US61/474,848 | 2011-04-13 | ||
| PCT/US2012/033675 WO2012142523A2 (en) | 2011-04-13 | 2012-04-13 | 1'-substituted pyrimidine n-nucleoside analogs for antiviral treatment |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014514308A JP2014514308A (ja) | 2014-06-19 |
| JP2014514308A5 true JP2014514308A5 (https=) | 2015-05-28 |
| JP6043338B2 JP6043338B2 (ja) | 2016-12-14 |
Family
ID=46001834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014505381A Expired - Fee Related JP6043338B2 (ja) | 2011-04-13 | 2012-04-13 | 抗ウイルス治療用の１’−置換ピリミジンｎ−ヌクレオシド類似体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8877733B2 (https=) |
| EP (1) | EP2697241B1 (https=) |
| JP (1) | JP6043338B2 (https=) |
| KR (1) | KR20140019832A (https=) |
| CN (1) | CN103476783A (https=) |
| AU (1) | AU2012242517B2 (https=) |
| BR (1) | BR112013026219A2 (https=) |
| CA (1) | CA2830689A1 (https=) |
| EA (1) | EA201391264A1 (https=) |
| ES (1) | ES2744587T3 (https=) |
| IL (1) | IL228680A0 (https=) |
| MX (1) | MX2013011915A (https=) |
| WO (1) | WO2012142523A2 (https=) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| LT1576138T (lt) | 2002-11-15 | 2017-06-26 | Idenix Pharmaceuticals Llc | 2`-šakoti nukleozidai derinyje su interferonu ir flaviviridae mutacija |
| MX2012003126A (es) | 2009-09-21 | 2012-06-19 | Gilead Sciences Inc | Procesos e intermedios para la preparacion de analogos de 1'-carbonucleosidos sustituidos. |
| ES2524356T3 (es) | 2010-07-22 | 2014-12-05 | Gilead Sciences, Inc. | Métodos y compuestos para tratar infecciones provocadas por virus Paramyxoviridae |
| AR088441A1 (es) | 2011-09-12 | 2014-06-11 | Idenix Pharmaceuticals Inc | Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales |
| US8507460B2 (en) | 2011-10-14 | 2013-08-13 | Idenix Pharmaceuticals, Inc. | Substituted 3′,5′-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| JP6165848B2 (ja) | 2012-05-22 | 2017-07-19 | イデニク ファーマシューティカルズ エルエルシー | 肝疾患のためのｄ−アミノ酸化合物 |
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| ES2671478T3 (es) | 2012-08-31 | 2018-06-06 | Novartis Ag | Derivados de 2'-etinil nucleósidos para el tratamiento de infecciones virales |
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| EP2906579B1 (en) | 2012-10-08 | 2018-04-18 | Idenix Pharmaceuticals LLC. | 2'-chloro nucleoside analogs for hcv infection |
| EP2935304A1 (en) * | 2012-12-19 | 2015-10-28 | IDENIX Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| BR112015014457A2 (pt) | 2012-12-21 | 2017-11-21 | Alios Biopharma Inc | composto ou sal farmaceuticamente aceitável do mesmo e composição farmacêutica e respectivos usos e processos para melhorar ou tratar infecção de hcv, para inibir a atividade da ns5b polimerase do vírus da hepatite c e a replicação de vírus da hepatite c |
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| EP2981542B1 (en) | 2013-04-01 | 2021-09-15 | Idenix Pharmaceuticals LLC | 2',4'-fluoro nucleosides for the treatment of hcv |
| US9447132B2 (en) | 2013-04-12 | 2016-09-20 | Achillion Pharmaceuticals, Inc. | Highly active nucleoside derivative for the treatment of HCV |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 1′,4′-thio nucleosides for the treatment of HCV |
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| WO2015054465A1 (en) * | 2013-10-11 | 2015-04-16 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| WO2015061683A1 (en) * | 2013-10-25 | 2015-04-30 | Idenix Pharmaceuticals, Inc. | D-amino acid phosphoramidate and d-alanine thiophosphoramidate pronucleotides of nucleoside compounds useful for the treatment of hcv |
| US10202411B2 (en) | 2014-04-16 | 2019-02-12 | Idenix Pharmaceuticals Llc | 3′-substituted methyl or alkynyl nucleosides nucleotides for the treatment of HCV |
| TWI687432B (zh) | 2014-10-29 | 2020-03-11 | 美商基利科學股份有限公司 | 絲狀病毒科病毒感染之治療 |
| JP7381190B2 (ja) | 2014-12-26 | 2023-11-15 | エモリー・ユニバーシテイ | Ｎ４－ヒドロキシシチジン及び誘導体並びにそれに関連する抗ウイルス用途 |
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| BR112019012057A2 (pt) * | 2016-12-15 | 2019-11-12 | Meharry Medical College | agente antiviral, composição farmacêutica para a administração do mesmo e métodos de redução na replicação do vírus zika (zikv) e tratamento de doença mediada pelo vírus zika (zikv) |
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| WO2020072931A2 (en) * | 2018-10-04 | 2020-04-09 | Octagon Therapeutics Inc. | Pre-activated nucleoside impdh inhibitors as anti-infective drugs |
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| KR20250133471A (ko) | 2020-02-18 | 2025-09-05 | 길리애드 사이언시즈, 인코포레이티드 | 항바이러스 화합물 |
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| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
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| KR20220153619A (ko) | 2020-03-12 | 2022-11-18 | 길리애드 사이언시즈, 인코포레이티드 | 1'-시아노 뉴클레오사이드의 제조 방법 |
| CN111548384B (zh) * | 2020-03-29 | 2021-04-27 | 常州安蒂卫生物科技有限公司 | 用于抗病毒治疗的被取代的n4-羟基胞苷衍生物及其前药 |
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-
2012
- 2012-04-13 US US13/447,017 patent/US8877733B2/en active Active
- 2012-04-13 JP JP2014505381A patent/JP6043338B2/ja not_active Expired - Fee Related
- 2012-04-13 MX MX2013011915A patent/MX2013011915A/es not_active Application Discontinuation
- 2012-04-13 WO PCT/US2012/033675 patent/WO2012142523A2/en not_active Ceased
- 2012-04-13 CN CN2012800181025A patent/CN103476783A/zh active Pending
- 2012-04-13 AU AU2012242517A patent/AU2012242517B2/en not_active Ceased
- 2012-04-13 KR KR1020137029678A patent/KR20140019832A/ko not_active Withdrawn
- 2012-04-13 EP EP12716969.6A patent/EP2697241B1/en active Active
- 2012-04-13 EA EA201391264A patent/EA201391264A1/ru unknown
- 2012-04-13 BR BR112013026219A patent/BR112013026219A2/pt not_active IP Right Cessation
- 2012-04-13 ES ES12716969T patent/ES2744587T3/es active Active
- 2012-04-13 CA CA2830689A patent/CA2830689A1/en not_active Abandoned
-
2013
- 2013-10-02 IL IL228680A patent/IL228680A0/en unknown
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