JP2015536954A5 - - Google Patents
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- JP2015536954A5 JP2015536954A5 JP2015540915A JP2015540915A JP2015536954A5 JP 2015536954 A5 JP2015536954 A5 JP 2015536954A5 JP 2015540915 A JP2015540915 A JP 2015540915A JP 2015540915 A JP2015540915 A JP 2015540915A JP 2015536954 A5 JP2015536954 A5 JP 2015536954A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- hydrogen
- optionally substituted
- butyl
- ethyl
- 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.)
- Pending
Links
- -1 chloro, bromo, iodo, methyl Chemical group 0.000 claims description 162
- 229910052739 hydrogen Inorganic materials 0.000 claims description 106
- 239000001257 hydrogen Substances 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 102
- 150000002431 hydrogen Chemical class 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 30
- 150000001356 alkyl thiols Chemical class 0.000 claims description 26
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 26
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 26
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 26
- 150000003573 thiols Chemical class 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 25
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 125000006242 amine protecting group Chemical group 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000002346 iodo group Chemical group I* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 3
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 3
- 201000004101 esophageal cancer Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- GQNZGCARKRHPOH-RQIKCTSVSA-N miocamycin Chemical compound C1[C@](OC(C)=O)(C)[C@@H](OC(=O)CC)[C@H](C)O[C@H]1O[C@H]1[C@H](N(C)C)[C@@H](O)[C@H](O[C@@H]2[C@H]([C@H](OC(=O)CC)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](OC(C)=O)[C@H](C)C[C@@H]2CC=O)OC)O[C@@H]1C GQNZGCARKRHPOH-RQIKCTSVSA-N 0.000 claims description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- 229950010765 pivalate Drugs 0.000 claims description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 2
- 241000701022 Cytomegalovirus Species 0.000 claims description 2
- 241000725619 Dengue virus Species 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 208000009889 Herpes Simplex Diseases 0.000 claims description 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000005252 hepatitis A Diseases 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 claims description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims 1
- JJWSNOOGIUMOEE-UHFFFAOYSA-N Monomethylmercury Chemical compound [Hg]C JJWSNOOGIUMOEE-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 241000710772 Yellow fever virus Species 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 201000005621 esophagus lymphoma Diseases 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229940051021 yellow-fever virus Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 46
- 208000035269 cancer or benign tumor Diseases 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical group COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 0 OC[C@]([C@](C1(F)F)O)O*1N(C=CC(NC(c1cc(Cl)cc(Cl)c1)=O)=N1)C1=O Chemical compound OC[C@]([C@](C1(F)F)O)O*1N(C=CC(NC(c1cc(Cl)cc(Cl)c1)=O)=N1)C1=O 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 2
- 229960004562 carboplatin Drugs 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- KKMXRZRAIUFWOH-VEWSYLICSA-N CC[C@H]([C@H]1O)O[C@@](C)(CN2C=CC(NC(c(c(OC)ccc3)c3OC)=O)=NC2O)C1(F)F Chemical compound CC[C@H]([C@H]1O)O[C@@](C)(CN2C=CC(NC(c(c(OC)ccc3)c3OC)=O)=NC2O)C1(F)F KKMXRZRAIUFWOH-VEWSYLICSA-N 0.000 description 1
- OSKQLTHIMAVQNG-VQIVBJKUSA-N C[C@](C(COC1CO)N(C=CC(NC(c2cc(OC)cc(OC)c2)=O)=N2)C2=O)([C@@H]1O)F Chemical compound C[C@](C(COC1CO)N(C=CC(NC(c2cc(OC)cc(OC)c2)=O)=N2)C2=O)([C@@H]1O)F OSKQLTHIMAVQNG-VQIVBJKUSA-N 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- 208000003152 Yellow Fever Diseases 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261723708P | 2012-11-07 | 2012-11-07 | |
| US61/723,708 | 2012-11-07 | ||
| PCT/US2013/068965 WO2014074725A1 (en) | 2012-11-07 | 2013-11-07 | Substituted gemcitabine aryl amide analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015536954A JP2015536954A (ja) | 2015-12-24 |
| JP2015536954A5 true JP2015536954A5 (https=) | 2016-12-15 |
Family
ID=50685152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015540915A Pending JP2015536954A (ja) | 2012-11-07 | 2013-11-07 | 置換ゲムシタビンアリールアミド類似体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9447137B2 (https=) |
| EP (1) | EP2916840B1 (https=) |
| JP (1) | JP2015536954A (https=) |
| CN (1) | CN104955458A (https=) |
| CA (1) | CA2890359A1 (https=) |
| WO (1) | WO2014074725A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104955458A (zh) * | 2012-11-07 | 2015-09-30 | Z·索 | 取代的吉西他滨芳基酰胺类似物和使用所述类似物的治疗方法 |
| US10000521B2 (en) | 2013-03-15 | 2018-06-19 | Nucorion Pharmaceuticals, Inc. | Substituted gemcitabine bicyclic amide analogs and treatment methods using same |
| WO2015134334A1 (en) * | 2014-03-03 | 2015-09-11 | Suo Zucai | Gemcitabine analogs |
| JP6855248B2 (ja) * | 2014-06-25 | 2021-04-07 | ヌカナ ピーエルシー | ゲムシタビン−プロドラッグを含む製剤 |
| CA3030408A1 (en) * | 2016-07-11 | 2018-01-18 | Hennepin Life Sciences, Llc | Compositions for sexually transmitted diseases |
| US10435429B2 (en) | 2017-10-03 | 2019-10-08 | Nucorion Pharmaceuticals, Inc. | 5-fluorouridine monophosphate cyclic triester compounds |
| EP3752511A4 (en) | 2018-01-10 | 2021-12-29 | Nucorion Pharmaceuticals, Inc. | Phosphor(n)amidatacetal and phosph(on)atalcetal compounds |
| US11427550B2 (en) | 2018-01-19 | 2022-08-30 | Nucorion Pharmaceuticals, Inc. | 5-fluorouracil compounds |
| PE20210367A1 (es) | 2018-02-02 | 2021-02-26 | Maverix Oncology Inc | Conjugados de farmacos de molecula pequena de monofosfato de gemcitabina |
| CN114206896B (zh) | 2019-07-17 | 2024-12-17 | 纽科利制药公司 | 环状脱氧核糖核苷酸化合物 |
| CN115605492B (zh) | 2020-04-21 | 2025-09-16 | 配体制药股份有限公司 | 核苷酸前药化合物 |
| US12552820B2 (en) | 2020-04-21 | 2026-02-17 | Ligand Pharmaceuticals Incorporated | Benzyloxy phosph(on)ate compounds |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61204193A (ja) * | 1985-03-05 | 1986-09-10 | Takeda Chem Ind Ltd | シトシンヌクレオシド類の製造法 |
| CA1327358C (en) * | 1987-11-17 | 1994-03-01 | Morio Fujiu | Fluoro cytidine derivatives |
| ES2349762T3 (es) * | 2000-08-10 | 2011-01-11 | Pfizer Italia S.R.L. | Biciclo-pirazoles activos como inhibidores de quinasas, procedimientos para su preparación y composiciones farmacéuticas que los comprenden. |
| PL374781A1 (en) * | 2002-06-28 | 2005-10-31 | Idenix (Cayman) Limited | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| KR100874052B1 (ko) | 2004-12-17 | 2008-12-12 | 일라이 릴리 앤드 캄파니 | 젬시타빈의 아미드 전구약, 그의 조성물 및 그의 용도 |
| ES2436404T3 (es) * | 2005-10-03 | 2013-12-30 | University Health Network | Inhibidores ODCasa para el tratamiento de malaria |
| WO2007117760A2 (en) * | 2006-02-06 | 2007-10-18 | Dr. Reddy's Laboratories Ltd. | Preparation of gemcitabine |
| FR2907786B1 (fr) * | 2006-10-27 | 2009-09-18 | Univ Grenoble 1 | Thionucleosides et applications pharmaceutiques |
| WO2008030373A2 (en) | 2006-09-01 | 2008-03-13 | University Of Georgia Research Foundation, Inc. | L- oddc prodrugs for cancer |
| WO2009042064A2 (en) * | 2007-09-21 | 2009-04-02 | Nektar Therapeutics Al, Corporation | Oligomer-nucleoside phosphate conjugates |
| JP2011503084A (ja) * | 2007-11-07 | 2011-01-27 | シェーリング コーポレイション | 新規の細胞周期チェックポイント調節剤およびこれらの調節剤とチェックポイント阻害剤との併用 |
| US8859490B2 (en) * | 2008-09-03 | 2014-10-14 | Nanyang Technological University | Peptide nucleic acid monomers and oligomers |
| WO2010063080A1 (en) * | 2008-12-05 | 2010-06-10 | Commonwealth Scientific And Industrial Research Organisation | Amphiphile prodrugs |
| CN101525361B (zh) * | 2009-04-21 | 2010-11-17 | 济南圣鲁金药物技术开发有限公司 | 基于吉西他滨结构的前药及其合成方法及应用 |
| CN101921303A (zh) * | 2009-06-09 | 2010-12-22 | 曾慧慧 | 苯并异硒唑酮二氟胞苷类化合物及其制备方法和其用途 |
| US20120070411A1 (en) * | 2010-09-22 | 2012-03-22 | Alios Biopharma, Inc. | Substituted nucleotide analogs |
| AU2013235220C1 (en) | 2011-12-22 | 2019-03-28 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| WO2014047199A1 (en) * | 2012-09-19 | 2014-03-27 | The Research Foundation For The State University Of New York | Novel prodrugs for selective anticancer therapy |
| CN104955458A (zh) | 2012-11-07 | 2015-09-30 | Z·索 | 取代的吉西他滨芳基酰胺类似物和使用所述类似物的治疗方法 |
| US10000521B2 (en) * | 2013-03-15 | 2018-06-19 | Nucorion Pharmaceuticals, Inc. | Substituted gemcitabine bicyclic amide analogs and treatment methods using same |
| WO2015134334A1 (en) | 2014-03-03 | 2015-09-11 | Suo Zucai | Gemcitabine analogs |
-
2013
- 2013-11-07 CN CN201380069308.5A patent/CN104955458A/zh active Pending
- 2013-11-07 JP JP2015540915A patent/JP2015536954A/ja active Pending
- 2013-11-07 WO PCT/US2013/068965 patent/WO2014074725A1/en not_active Ceased
- 2013-11-07 CA CA2890359A patent/CA2890359A1/en not_active Abandoned
- 2013-11-07 EP EP13853078.7A patent/EP2916840B1/en not_active Not-in-force
- 2013-11-07 US US14/440,811 patent/US9447137B2/en not_active Expired - Fee Related
-
2016
- 2016-08-08 US US15/231,310 patent/US9744186B2/en not_active Expired - Fee Related
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