JP2015515465A5 - - Google Patents
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- Publication number
- JP2015515465A5 JP2015515465A5 JP2015503346A JP2015503346A JP2015515465A5 JP 2015515465 A5 JP2015515465 A5 JP 2015515465A5 JP 2015503346 A JP2015503346 A JP 2015503346A JP 2015503346 A JP2015503346 A JP 2015503346A JP 2015515465 A5 JP2015515465 A5 JP 2015515465A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- indol
- urea
- methylpiperazin
- 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
- 150000001875 compounds Chemical class 0.000 claims description 44
- -1 1H-benzimidazolyl Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 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 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- RBYNETHHEMQMNK-UHFFFAOYSA-N 1-(2-aminoethyl)-3-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]urea Chemical compound CCC1=CC(NC(=O)NCCN)=CC=C1CC1=CNC2=CC=CC=C12 RBYNETHHEMQMNK-UHFFFAOYSA-N 0.000 claims description 2
- YKQHEDNVQMHJLH-UHFFFAOYSA-N 1-[3-(1h-indol-2-ylmethoxy)-5-propoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]thiourea Chemical compound C=1C(OCC=2NC3=CC=CC=C3C=2)=CC(OCCC)=CC=1NC(=S)NCCN1CCN(C)CC1 YKQHEDNVQMHJLH-UHFFFAOYSA-N 0.000 claims description 2
- QYOKBBSVTMCTLM-UHFFFAOYSA-N 1-[3-(1h-indol-2-ylmethoxy)-5-propoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OCC=2NC3=CC=CC=C3C=2)=CC(OCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 QYOKBBSVTMCTLM-UHFFFAOYSA-N 0.000 claims description 2
- WDNBIPQDFNRSFG-UHFFFAOYSA-N 1-[3-(1h-indol-3-ylmethoxy)-5-propoxyphenyl]-3-(2-piperazin-1-ylethyl)urea Chemical compound C=1C(OCC=2C3=CC=CC=C3NC=2)=CC(OCCC)=CC=1NC(=O)NCCN1CCNCC1 WDNBIPQDFNRSFG-UHFFFAOYSA-N 0.000 claims description 2
- HOGDGYRAWLHIGX-UHFFFAOYSA-N 1-[3-(1h-indol-3-ylmethoxy)-5-propoxyphenyl]-3-(2-piperidin-4-ylethyl)urea Chemical compound C=1C(OCC=2C3=CC=CC=C3NC=2)=CC(OCCC)=CC=1NC(=O)NCCC1CCNCC1 HOGDGYRAWLHIGX-UHFFFAOYSA-N 0.000 claims description 2
- CVGWWSWCDADCHQ-UHFFFAOYSA-N 1-[3-(1h-indol-3-ylmethyl)-5-methoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC)=CC(CC=2C3=CC=CC=C3NC=2)=CC=1NC(=O)NCCN1CCN(C)CC1 CVGWWSWCDADCHQ-UHFFFAOYSA-N 0.000 claims description 2
- NXJSXLOWXWJKAV-UHFFFAOYSA-N 1-[3-(1h-indol-3-ylmethyl)-5-propan-2-yloxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC(C)C)=CC(CC=2C3=CC=CC=C3NC=2)=CC=1NC(=O)NCCN1CCN(C)CC1 NXJSXLOWXWJKAV-UHFFFAOYSA-N 0.000 claims description 2
- OEWMTCRSEPVHFY-UHFFFAOYSA-N 1-[3-[2-(1h-indol-3-yl)ethyl]-5-propan-2-ylphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]thiourea Chemical compound C=1C(C(C)C)=CC(CCC=2C3=CC=CC=C3NC=2)=CC=1NC(=S)NCCN1CCN(C)CC1 OEWMTCRSEPVHFY-UHFFFAOYSA-N 0.000 claims description 2
- QVPSBZWFQYGAKC-UHFFFAOYSA-N 1-[3-butyl-4-(1h-indol-3-ylmethyl)-5-(trifluoromethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC(F)(F)F)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 QVPSBZWFQYGAKC-UHFFFAOYSA-N 0.000 claims description 2
- GGBQZKQFGCFYRL-UHFFFAOYSA-N 1-[3-butyl-4-(1h-indol-3-ylmethyl)-5-methoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 GGBQZKQFGCFYRL-UHFFFAOYSA-N 0.000 claims description 2
- VAGAPCWJTBONAS-UHFFFAOYSA-N 1-[3-butyl-5-(1h-imidazo[4,5-b]pyrazin-2-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(CCCC)=CC(CC=2NC3=NC=CN=C3N=2)=CC=1NC(=O)NCCN1CCN(C)CC1 VAGAPCWJTBONAS-UHFFFAOYSA-N 0.000 claims description 2
- DRKVIPKWAHSPMY-UHFFFAOYSA-N 1-[3-butyl-5-(1h-indol-3-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OCC=2C3=CC=CC=C3NC=2)=CC(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 DRKVIPKWAHSPMY-UHFFFAOYSA-N 0.000 claims description 2
- QAKMKLOSXMOKPU-UHFFFAOYSA-N 1-[3-butyl-5-(1h-indol-3-ylmethyl)phenyl]-3-(2-piperidin-4-ylethyl)urea Chemical compound C=1C(CCCC)=CC(CC=2C3=CC=CC=C3NC=2)=CC=1NC(=O)NCCC1CCNCC1 QAKMKLOSXMOKPU-UHFFFAOYSA-N 0.000 claims description 2
- UDVLSYLVSYNMHJ-UHFFFAOYSA-N 1-[3-butyl-5-hydroxy-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4,4-dimethylpiperazin-4-ium-1-yl)ethyl]urea;iodide Chemical compound [I-].C=1C(O)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CC[N+](C)(C)CC1 UDVLSYLVSYNMHJ-UHFFFAOYSA-N 0.000 claims description 2
- BUMROPPMYBHLLF-UHFFFAOYSA-N 1-[3-butyl-5-hydroxy-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(O)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 BUMROPPMYBHLLF-UHFFFAOYSA-N 0.000 claims description 2
- ZHPUPZFRXZBEKU-UHFFFAOYSA-N 1-[3-cyclohexyloxy-5-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC(CC=2C3=CC=CC=C3NC=2)=CC(OC2CCCCC2)=C1 ZHPUPZFRXZBEKU-UHFFFAOYSA-N 0.000 claims description 2
- RDXTURUZNDFRCO-UHFFFAOYSA-N 1-[3-cyclopentyloxy-5-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC(CC=2C3=CC=CC=C3NC=2)=CC(OC2CCCC2)=C1 RDXTURUZNDFRCO-UHFFFAOYSA-N 0.000 claims description 2
- LWYSHXBDBGXEDU-UHFFFAOYSA-N 1-[3-cyclopropyloxy-5-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC(CC=2C3=CC=CC=C3NC=2)=CC(OC2CC2)=C1 LWYSHXBDBGXEDU-UHFFFAOYSA-N 0.000 claims description 2
- SRSIGTFBRAKBIH-UHFFFAOYSA-N 1-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]-3-(2-piperazin-1-ylethyl)urea Chemical compound C=1C=C(CC=2C3=CC=CC=C3NC=2)C(CC)=CC=1NC(=O)NCCN1CCNCC1 SRSIGTFBRAKBIH-UHFFFAOYSA-N 0.000 claims description 2
- DLRKIDHQJPSZET-UHFFFAOYSA-N 1-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(1h-imidazol-5-yl)ethyl]urea Chemical compound C=1C=C(CC=2C3=CC=CC=C3NC=2)C(CC)=CC=1NC(=O)NCCC1=CN=CN1 DLRKIDHQJPSZET-UHFFFAOYSA-N 0.000 claims description 2
- FKFSPCZNABVGFH-UHFFFAOYSA-N 1-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C=C(CC=2C3=CC=CC=C3NC=2)C(CC)=CC=1NC(=O)NCCN1CCN(C)CC1 FKFSPCZNABVGFH-UHFFFAOYSA-N 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims description 2
- 201000002832 Lewy body dementia Diseases 0.000 claims description 2
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 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
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000004845 protein aggregation Effects 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- KSZAHOJUYDFQKN-UHFFFAOYSA-N 1-[3-(1h-benzimidazol-2-ylmethyl)-5-butylphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(CCCC)=CC(CC=2NC3=CC=CC=C3N=2)=CC=1NC(=O)NCCN1CCN(C)CC1 KSZAHOJUYDFQKN-UHFFFAOYSA-N 0.000 claims 1
- GJXOQMNHEKHGFM-UHFFFAOYSA-N 1-[3-(1h-indol-2-ylmethoxy)-5-propoxyphenyl]-3-(2-piperazin-1-ylethyl)urea Chemical compound C=1C(OCC=2NC3=CC=CC=C3C=2)=CC(OCCC)=CC=1NC(=O)NCCN1CCNCC1 GJXOQMNHEKHGFM-UHFFFAOYSA-N 0.000 claims 1
- KPKZFNMOWJGMGI-UHFFFAOYSA-N 1-[3-(1h-indol-2-ylmethoxy)-5-propoxyphenyl]-3-(2-piperidin-4-ylethyl)urea Chemical compound C=1C(OCC=2NC3=CC=CC=C3C=2)=CC(OCCC)=CC=1NC(=O)NCCC1CCNCC1 KPKZFNMOWJGMGI-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 3
- DSDXCHSRGHORBB-UHFFFAOYSA-N 1-[3-butyl-5-(2,3-dihydro-1h-benzimidazol-2-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(CCCC)=CC(CC2NC3=CC=CC=C3N2)=CC=1NC(=O)NCCN1CCN(C)CC1 DSDXCHSRGHORBB-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261616771P | 2012-03-28 | 2012-03-28 | |
| US61/616,771 | 2012-03-28 | ||
| PCT/US2013/032552 WO2013148365A1 (en) | 2012-03-28 | 2013-03-15 | Phenyl-urea and phenyl-carbamate derivatives as inhibitors of protein aggregation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015515465A JP2015515465A (ja) | 2015-05-28 |
| JP2015515465A5 true JP2015515465A5 (https=) | 2016-04-28 |
| JP6159388B2 JP6159388B2 (ja) | 2017-07-05 |
Family
ID=49261100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015503346A Active JP6159388B2 (ja) | 2012-03-28 | 2013-03-15 | タンパク質凝集の阻害剤としてのフェニル−尿素及びフェニル−カルバメート誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9527852B2 (https=) |
| EP (1) | EP2830608B8 (https=) |
| JP (1) | JP6159388B2 (https=) |
| KR (1) | KR20150002713A (https=) |
| CN (1) | CN104363903A (https=) |
| AU (1) | AU2013240219A1 (https=) |
| CA (1) | CA2867175A1 (https=) |
| ES (1) | ES2768602T3 (https=) |
| HK (1) | HK1202452A1 (https=) |
| IL (1) | IL234825A0 (https=) |
| IN (1) | IN2014DN08633A (https=) |
| MX (1) | MX2014011615A (https=) |
| NZ (1) | NZ631388A (https=) |
| RU (1) | RU2014143242A (https=) |
| WO (1) | WO2013148365A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA032374B1 (ru) | 2014-01-29 | 2019-05-31 | ЮСиБи БАЙОФАРМА СПРЛ | Гетероарильные амиды в качестве ингибиторов агрегации белков |
| WO2016040780A1 (en) * | 2014-09-11 | 2016-03-17 | Neuropore Therapies, Inc. | Aminomethyl- and methyloxy-linked tricyclic compounds as inhibitors of protein aggregation |
| ES2885049T3 (es) | 2015-07-29 | 2021-12-13 | UCB Biopharma SRL | Derivados de bis-heteroarilo como moduladores de la agregación de proteínas |
| US10913735B2 (en) | 2017-01-26 | 2021-02-09 | UCB Biopharma SRL | Bis-heteroaryl derivatives as modulators of protein aggregation |
| WO2018138085A1 (en) | 2017-01-26 | 2018-08-02 | Ucb Biopharma Sprl | Alkoxy bis-heteroaryl derivatives as modulators of protein aggregation |
| CN110167937B (zh) | 2017-01-26 | 2022-03-29 | Ucb生物制药私人有限公司 | 作为蛋白质聚集调节剂的二环双-杂芳基衍生物 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59712297D1 (de) | 1996-01-26 | 2005-06-09 | Altana Pharma Ag | 3-alkylimidazopyridine |
| US6617351B1 (en) * | 1998-07-31 | 2003-09-09 | Eli Lilly And Company | Amide, carbamate, and urea derivatives |
| WO2001036403A1 (en) * | 1999-11-16 | 2001-05-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Urea derivatives as anti-inflammatory agents |
| PL223343B1 (pl) * | 2000-10-30 | 2016-10-31 | Kudos Pharm Ltd | Zastosowanie związku, kompozycja farmaceutyczna zawierająca związek oraz pochodne ftalazynonowe |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| WO2004080950A1 (en) | 2003-03-14 | 2004-09-23 | H. Lundbeck A/S | Substituted aniline derivatives |
| BRPI0408437A (pt) | 2003-03-21 | 2006-04-04 | Lundbeck & Co As H | derivados de p-diaminobenzeno substituìdos, composição farmacêutica, e, uso da mesma |
| US20050192314A1 (en) * | 2003-11-13 | 2005-09-01 | Ambit Biosciences Corporation | Urea derivatives as C-kit modulators |
| CN102206216B (zh) | 2005-06-22 | 2014-11-12 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| US8097626B2 (en) * | 2006-04-21 | 2012-01-17 | Glaxosmithkline Llc | IL-8 receptor antagonists |
| WO2008044688A1 (en) * | 2006-10-11 | 2008-04-17 | Daiichi Sankyo Company, Limited | Urea derivative |
| WO2010036316A1 (en) | 2008-09-24 | 2010-04-01 | Yangbo Feng | Urea and carbamate compounds and analogs as kinase inhibitors |
| NZ600449A (en) * | 2009-12-16 | 2014-10-31 | Neuropore Therapies Inc | Compound suitable for the treatment of synucleopathies |
-
2013
- 2013-03-15 CA CA2867175A patent/CA2867175A1/en not_active Abandoned
- 2013-03-15 MX MX2014011615A patent/MX2014011615A/es unknown
- 2013-03-15 CN CN201380017441.6A patent/CN104363903A/zh active Pending
- 2013-03-15 AU AU2013240219A patent/AU2013240219A1/en not_active Abandoned
- 2013-03-15 ES ES13768915T patent/ES2768602T3/es active Active
- 2013-03-15 HK HK15103189.8A patent/HK1202452A1/xx unknown
- 2013-03-15 RU RU2014143242A patent/RU2014143242A/ru not_active Application Discontinuation
- 2013-03-15 WO PCT/US2013/032552 patent/WO2013148365A1/en not_active Ceased
- 2013-03-15 NZ NZ631388A patent/NZ631388A/en not_active IP Right Cessation
- 2013-03-15 KR KR1020147030291A patent/KR20150002713A/ko not_active Withdrawn
- 2013-03-15 JP JP2015503346A patent/JP6159388B2/ja active Active
- 2013-03-15 US US14/388,783 patent/US9527852B2/en active Active
- 2013-03-15 EP EP13768915.4A patent/EP2830608B8/en active Active
-
2014
- 2014-09-23 IL IL234825A patent/IL234825A0/en unknown
- 2014-10-15 IN IN8633DEN2014 patent/IN2014DN08633A/en unknown