CA2635680A1 - Boron-containing small molecules - Google Patents
Boron-containing small molecules Download PDFInfo
- Publication number
- CA2635680A1 CA2635680A1 CA002635680A CA2635680A CA2635680A1 CA 2635680 A1 CA2635680 A1 CA 2635680A1 CA 002635680 A CA002635680 A CA 002635680A CA 2635680 A CA2635680 A CA 2635680A CA 2635680 A1 CA2635680 A1 CA 2635680A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- unsubstituted
- compound
- member selected
- trna synthetase
- 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.)
- Abandoned
Links
- 229910052796 boron Inorganic materials 0.000 title claims description 37
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims description 32
- 150000003384 small molecules Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 483
- 210000000282 nail Anatomy 0.000 claims abstract description 128
- 241000233866 Fungi Species 0.000 claims abstract description 39
- 210000004209 hair Anatomy 0.000 claims abstract description 30
- 210000000003 hoof Anatomy 0.000 claims abstract description 30
- 208000010195 Onychomycosis Diseases 0.000 claims abstract description 25
- 201000005882 tinea unguium Diseases 0.000 claims abstract description 25
- -1 methoxymethoxy Chemical group 0.000 claims description 814
- 238000000034 method Methods 0.000 claims description 177
- 108700028939 Amino Acyl-tRNA Synthetases Proteins 0.000 claims description 145
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 145
- 102000052866 Amino Acyl-tRNA Synthetases Human genes 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 130
- 125000003118 aryl group Chemical group 0.000 claims description 117
- 125000001072 heteroaryl group Chemical group 0.000 claims description 111
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 109
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 104
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 99
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 99
- 125000004429 atom Chemical group 0.000 claims description 97
- 244000005700 microbiome Species 0.000 claims description 79
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 150000002367 halogens Chemical class 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 62
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 61
- 150000002148 esters Chemical class 0.000 claims description 60
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 58
- 241000282414 Homo sapiens Species 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 50
- 238000009472 formulation Methods 0.000 claims description 48
- 150000001413 amino acids Chemical class 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 208000015181 infectious disease Diseases 0.000 claims description 42
- 241001465754 Metazoa Species 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 230000002401 inhibitory effect Effects 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 125000004122 cyclic group Chemical group 0.000 claims description 27
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
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- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 23
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
- 108010076876 Keratins Proteins 0.000 claims description 21
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- 239000002253 acid Substances 0.000 claims description 20
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 20
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 230000012010 growth Effects 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 241001480043 Arthrodermataceae Species 0.000 claims description 17
- 238000003556 assay Methods 0.000 claims description 17
- 230000037304 dermatophytes Effects 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 238000001953 recrystallisation Methods 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910001868 water Inorganic materials 0.000 claims description 17
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 230000005764 inhibitory process Effects 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 244000045947 parasite Species 0.000 claims description 16
- LFQDNHWZDQTITF-UHFFFAOYSA-N tavaborole Chemical compound FC1=CC=C2B(O)OCC2=C1 LFQDNHWZDQTITF-UHFFFAOYSA-N 0.000 claims description 16
- 102000029793 Isoleucine-tRNA ligase Human genes 0.000 claims description 15
- 101710176147 Isoleucine-tRNA ligase, cytoplasmic Proteins 0.000 claims description 15
- 101710149031 Probable isoleucine-tRNA ligase, cytoplasmic Proteins 0.000 claims description 15
- 241000223238 Trichophyton Species 0.000 claims description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 15
- 230000035772 mutation Effects 0.000 claims description 15
- 150000007523 nucleic acids Chemical group 0.000 claims description 15
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 241000223229 Trichophyton rubrum Species 0.000 claims description 14
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 239000002773 nucleotide Substances 0.000 claims description 14
- 125000003729 nucleotide group Chemical group 0.000 claims description 14
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910006069 SO3H Inorganic materials 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 210000004904 fingernail bed Anatomy 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
- MLRBNIXMTWSDJU-UHFFFAOYSA-N 2-benzylfuran Chemical class C=1C=CC=CC=1CC1=CC=CO1 MLRBNIXMTWSDJU-UHFFFAOYSA-N 0.000 claims description 12
- 101000787278 Arabidopsis thaliana Valine-tRNA ligase, chloroplastic/mitochondrial 2 Proteins 0.000 claims description 12
- 101000787296 Arabidopsis thaliana Valine-tRNA ligase, mitochondrial 1 Proteins 0.000 claims description 12
- 101000787280 Dictyostelium discoideum Probable valine-tRNA ligase, mitochondrial Proteins 0.000 claims description 12
- 102000013625 Valine-tRNA Ligase Human genes 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 125000005864 sulfonamidyl group Chemical group 0.000 claims description 12
- 238000012360 testing method Methods 0.000 claims description 12
- 229930024421 Adenine Natural products 0.000 claims description 11
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 11
- 108010092041 Lysine-tRNA Ligase Proteins 0.000 claims description 11
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 11
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 11
- 229960000643 adenine Drugs 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- 108010058060 Alanine-tRNA ligase Proteins 0.000 claims description 10
- 102000006268 Alanine-tRNA ligase Human genes 0.000 claims description 10
- 102100026126 Proline-tRNA ligase Human genes 0.000 claims description 10
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 10
- 102000001618 Threonine-tRNA Ligase Human genes 0.000 claims description 10
- 108010029287 Threonine-tRNA ligase Proteins 0.000 claims description 10
- 230000004071 biological effect Effects 0.000 claims description 10
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 10
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 10
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- 108010042589 prolyl T RNA synthetase Proteins 0.000 claims description 10
- 150000003212 purines Chemical class 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
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- 108010003060 Methionine-tRNA ligase Proteins 0.000 claims description 9
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- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 8
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 8
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Classifications
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- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- C—CHEMISTRY; METALLURGY
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75522705P | 2005-12-30 | 2005-12-30 | |
| US60/755,227 | 2005-12-30 | ||
| US11/357,687 | 2006-02-16 | ||
| US11/357,687 US7582621B2 (en) | 2005-02-16 | 2006-02-16 | Boron-containing small molecules |
| PCT/US2006/005542 WO2006089067A2 (en) | 2005-02-16 | 2006-02-16 | Boron-containing small molecules |
| USPCT/US2006/05542 | 2006-02-16 | ||
| US74636106P | 2006-05-03 | 2006-05-03 | |
| US60/746,361 | 2006-05-03 | ||
| PCT/US2006/032238 WO2007078340A2 (en) | 2005-12-30 | 2006-08-16 | Boron-containing small molecules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2635680A1 true CA2635680A1 (en) | 2007-07-12 |
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ID=38225302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002635680A Abandoned CA2635680A1 (en) | 2005-12-30 | 2006-08-16 | Boron-containing small molecules |
Country Status (11)
| Country | Link |
|---|---|
| US (14) | US7767657B2 (OSRAM) |
| EP (1) | EP1976536A4 (OSRAM) |
| JP (1) | JP2009526751A (OSRAM) |
| KR (1) | KR20080110984A (OSRAM) |
| CN (3) | CN106008583A (OSRAM) |
| AU (1) | AU2006333527B2 (OSRAM) |
| BR (1) | BRPI0621279B1 (OSRAM) |
| CA (1) | CA2635680A1 (OSRAM) |
| IL (1) | IL192402A (OSRAM) |
| RU (1) | RU2008131324A (OSRAM) |
| WO (1) | WO2007078340A2 (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US9426996B2 (en) | 2013-01-30 | 2016-08-30 | Agrofresh Inc. | Use of benzoxaboroles as volatile antimicrobial agents on meats, plants, or plant parts |
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2006
- 2006-08-16 KR KR1020087018808A patent/KR20080110984A/ko not_active Withdrawn
- 2006-08-16 CN CN201610328000.3A patent/CN106008583A/zh active Pending
- 2006-08-16 US US11/505,591 patent/US7767657B2/en active Active
- 2006-08-16 AU AU2006333527A patent/AU2006333527B2/en active Active
- 2006-08-16 JP JP2008548499A patent/JP2009526751A/ja active Pending
- 2006-08-16 WO PCT/US2006/032238 patent/WO2007078340A2/en not_active Ceased
- 2006-08-16 CN CN201610328016.4A patent/CN106008571A/zh active Pending
- 2006-08-16 EP EP06801794A patent/EP1976536A4/en not_active Withdrawn
- 2006-08-16 CA CA002635680A patent/CA2635680A1/en not_active Abandoned
- 2006-08-16 RU RU2008131324/04A patent/RU2008131324A/ru not_active Application Discontinuation
- 2006-08-16 CN CN201610327999.XA patent/CN105949230A/zh active Pending
- 2006-08-16 BR BRPI0621279-4A patent/BRPI0621279B1/pt active IP Right Grant
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2008
- 2008-06-23 IL IL192402A patent/IL192402A/en active IP Right Grant
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2009
- 2009-12-02 US US12/629,753 patent/US8115026B2/en active Active
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2012
- 2012-01-23 US US13/356,488 patent/US8722917B2/en active Active
- 2012-09-07 US US13/607,321 patent/US20130059803A1/en not_active Abandoned
- 2012-09-07 US US13/607,405 patent/US20130064783A1/en not_active Abandoned
- 2012-09-07 US US13/607,250 patent/US20130059802A1/en not_active Abandoned
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2013
- 2013-04-12 US US13/861,846 patent/US20130210770A1/en not_active Abandoned
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2014
- 2014-03-07 US US14/201,459 patent/US9353133B2/en active Active
- 2014-11-10 US US14/537,771 patent/US20150119364A1/en not_active Abandoned
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2016
- 2016-02-17 US US15/046,322 patent/US9566289B2/en not_active Expired - Fee Related
- 2016-03-11 US US15/068,352 patent/US9549938B2/en not_active Expired - Fee Related
- 2016-04-05 US US15/091,394 patent/US9572823B2/en not_active Expired - Fee Related
- 2016-04-20 US US15/134,286 patent/US9566290B2/en not_active Expired - Fee Related
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