JP2007524670A5 - - Google Patents
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- Publication number
- JP2007524670A5 JP2007524670A5 JP2006551000A JP2006551000A JP2007524670A5 JP 2007524670 A5 JP2007524670 A5 JP 2007524670A5 JP 2006551000 A JP2006551000 A JP 2006551000A JP 2006551000 A JP2006551000 A JP 2006551000A JP 2007524670 A5 JP2007524670 A5 JP 2007524670A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- acceptable salt
- carbocyclyl
- heterocyclyl
- 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 103
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 150000003839 salts Chemical class 0.000 claims description 51
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 229910003827 NRaRb Inorganic materials 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 150000001540 azides Chemical class 0.000 claims description 8
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 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 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000006083 1-bromoethyl group Chemical group 0.000 claims description 2
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- KMGCKSAIIHOKCX-UHFFFAOYSA-N 2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2CC(O)CC2=C1 KMGCKSAIIHOKCX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 241000534944 Thia Species 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 108090000854 Oxidoreductases Proteins 0.000 description 6
- 102000004316 Oxidoreductases Human genes 0.000 description 6
- 101150053185 P450 gene Proteins 0.000 description 6
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 3
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 3
- 102000001708 Protein Isoforms Human genes 0.000 description 3
- 108010029485 Protein Isoforms Proteins 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 206010054261 Flavivirus infection Diseases 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 0 CC(C)c1cc(-c2c[s]c(*)n2)nc2c1cccc2 Chemical compound CC(C)c1cc(-c2c[s]c(*)n2)nc2c1cccc2 0.000 description 1
- 108010074922 Cytochrome P-450 CYP1A2 Proteins 0.000 description 1
- 108010026925 Cytochrome P-450 CYP2C19 Proteins 0.000 description 1
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 description 1
- 102100026533 Cytochrome P450 1A2 Human genes 0.000 description 1
- 102100036194 Cytochrome P450 2A6 Human genes 0.000 description 1
- 102100029363 Cytochrome P450 2C19 Human genes 0.000 description 1
- 102100039205 Cytochrome P450 3A4 Human genes 0.000 description 1
- 241000710831 Flavivirus Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 101000875170 Homo sapiens Cytochrome P450 2A6 Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 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 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000005884 carbocyclylalkyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- 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 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0400199-6 | 2004-01-30 | ||
| SE0400199A SE0400199D0 (sv) | 2004-01-30 | 2004-01-30 | HCV Protease inhbitors |
| SE0401288A SE0401288D0 (sv) | 2004-05-19 | 2004-05-19 | HCV NS-3 Serine Protease Inhbitors |
| SE0401288-6 | 2004-05-19 | ||
| SE0402562A SE0402562D0 (sv) | 2004-10-22 | 2004-10-22 | HCV Protease Inhbitors |
| SE0402562-3 | 2004-10-22 | ||
| PCT/SE2005/000096 WO2005073216A2 (en) | 2004-01-30 | 2005-01-28 | Hcv ns-3 serine protease inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007524670A JP2007524670A (ja) | 2007-08-30 |
| JP2007524670A5 true JP2007524670A5 (enExample) | 2012-04-12 |
| JP5248783B2 JP5248783B2 (ja) | 2013-07-31 |
Family
ID=34831013
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551000A Expired - Fee Related JP5248783B2 (ja) | 2004-01-30 | 2005-01-28 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| JP2006551001A Expired - Fee Related JP4902361B2 (ja) | 2004-01-30 | 2005-01-28 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| JP2010279178A Pending JP2011140488A (ja) | 2004-01-30 | 2010-12-15 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| JP2013234011A Expired - Fee Related JP5795619B2 (ja) | 2004-01-30 | 2013-11-12 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551001A Expired - Fee Related JP4902361B2 (ja) | 2004-01-30 | 2005-01-28 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| JP2010279178A Pending JP2011140488A (ja) | 2004-01-30 | 2010-12-15 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| JP2013234011A Expired - Fee Related JP5795619B2 (ja) | 2004-01-30 | 2013-11-12 | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
Country Status (32)
Families Citing this family (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
| AU2004240704B9 (en) * | 2003-05-21 | 2009-10-22 | Boehringer Ingelheim International Gmbh | Hepatitis C inhibitor compounds |
| US7491794B2 (en) | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| UA84050C2 (en) * | 2004-01-30 | 2008-09-10 | Медивир Аб | Hcv ns-3-serine protease inhibitors |
| EA012389B1 (ru) * | 2004-03-30 | 2009-10-30 | Интермун, Инк. | Макроциклические соединения в качестве ингибиторов вирусной репликации |
| US7323447B2 (en) | 2005-02-08 | 2008-01-29 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7592336B2 (en) | 2005-05-10 | 2009-09-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US7601686B2 (en) | 2005-07-11 | 2009-10-13 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| BRPI0613962A2 (pt) * | 2005-07-25 | 2009-03-24 | Intermune Inc | inibidores macrocìclicos inovadores de replicação de vìrus da hepatite c |
| ES2360417T3 (es) * | 2005-07-29 | 2011-06-03 | Tibotec Pharmaceuticals | Inhibidores macrocíclicos del virus de la hepatitis c. |
| CA2617099C (en) | 2005-07-29 | 2014-03-25 | Tibotec Pharmaceuticals Ltd. | Macrocyclic inhibitors of hepatitis c virus |
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| CN101273042B (zh) * | 2005-07-29 | 2013-11-06 | 泰博特克药品有限公司 | 丙型肝炎病毒的大环抑制剂 |
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| MY144607A (en) * | 2005-07-29 | 2011-10-14 | Tibotec Pharm Ltd | Macrocylic inhibitors of hepatitis c virus |
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| DK1919904T3 (da) | 2005-07-29 | 2014-04-07 | Janssen R & D Ireland | Makrocykliske inhibitorer af hepatitis-c-virus |
| AR055395A1 (es) | 2005-08-26 | 2007-08-22 | Vertex Pharma | Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c |
| DK1999129T3 (da) | 2005-10-11 | 2011-02-07 | Intermune Inc | Forbindelser og fremgangsmåder til inhibering af replikationen af hepatitis C-virus |
| US7772183B2 (en) | 2005-10-12 | 2010-08-10 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| DK1945797T3 (da) * | 2005-10-28 | 2012-08-06 | Boehringer Ingelheim Int | Hepatitis C-virus NS2/3-aktivitetsanalyse |
| US7741281B2 (en) | 2005-11-03 | 2010-06-22 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| KR20090024834A (ko) * | 2006-07-05 | 2009-03-09 | 인터뮨, 인크. | Ｃ형 간염 바이러스 복제의 신규 억제제 |
| WO2008008776A2 (en) | 2006-07-11 | 2008-01-17 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2041156B1 (en) | 2006-07-13 | 2013-11-20 | Achillion Pharmaceuticals, Inc. | 4-amino-4-oxobutanoyl peptides as inhibitors of viral replication |
| EP1881001A1 (en) * | 2006-07-20 | 2008-01-23 | Tibotec Pharmaceuticals Ltd. | HCV NS-3 serine protease inhibitors |
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| CA2660300C (en) * | 2006-08-09 | 2014-12-09 | Sumitomo Bakelite Co., Ltd. | Sugar chain-capturing substance and use thereof |
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| US7763584B2 (en) | 2006-11-16 | 2010-07-27 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US8003604B2 (en) | 2006-11-16 | 2011-08-23 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
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- 2005-01-28 DK DK05704765.6T patent/DK1713823T3/da active
- 2005-01-28 CA CA2552317A patent/CA2552317C/en not_active Expired - Fee Related
- 2005-01-28 MY MYPI20050349 patent/MY153011A/en unknown
- 2005-01-28 DE DE602005019979T patent/DE602005019979D1/de not_active Expired - Lifetime
- 2005-01-28 SI SI200530899T patent/SI1713823T1/sl unknown
-
2006
- 2006-07-13 IL IL176848A patent/IL176848A/en not_active IP Right Cessation
- 2006-07-18 IL IL176921A patent/IL176921A/en active Protection Beyond IP Right Term
- 2006-07-24 EC EC2006006725A patent/ECSP066725A/es unknown
- 2006-07-24 EC EC2006006726A patent/ECSP066726A/es unknown
- 2006-07-28 CR CR8539A patent/CR8539A/es not_active Application Discontinuation
- 2006-07-28 NI NI200600168A patent/NI200600168A/es unknown
- 2006-07-28 CR CR8540A patent/CR8540A/es not_active Application Discontinuation
- 2006-08-23 KR KR1020067016960A patent/KR101217036B1/ko not_active Expired - Fee Related
- 2006-08-29 NO NO20063851A patent/NO341392B1/no not_active IP Right Cessation
- 2006-08-29 ZA ZA2006/07214A patent/ZA200607214B/en unknown
-
2009
- 2009-09-11 US US12/557,638 patent/US20100003216A1/en not_active Abandoned
- 2009-12-21 US US12/642,984 patent/US20100166706A1/en not_active Abandoned
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2010
- 2010-02-10 CY CY20101100134T patent/CY1109779T1/el unknown
- 2010-12-15 JP JP2010279178A patent/JP2011140488A/ja active Pending
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2013
- 2013-11-12 JP JP2013234011A patent/JP5795619B2/ja not_active Expired - Fee Related
-
2014
- 2014-11-11 LU LU92595C patent/LU92595I2/xx unknown
- 2014-11-12 NL NL300703C patent/NL300703I2/nl unknown
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2017
- 2017-03-27 US US15/470,599 patent/US10172846B2/en not_active Expired - Fee Related
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