RU2015138488A - Способ получения бензоксазепиновых соединений - Google Patents
Способ получения бензоксазепиновых соединений Download PDFInfo
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- RU2015138488A RU2015138488A RU2015138488A RU2015138488A RU2015138488A RU 2015138488 A RU2015138488 A RU 2015138488A RU 2015138488 A RU2015138488 A RU 2015138488A RU 2015138488 A RU2015138488 A RU 2015138488A RU 2015138488 A RU2015138488 A RU 2015138488A
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- Prior art keywords
- reacting
- reagent
- iii
- pph
- palladium
- Prior art date
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- ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical class O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 28
- 239000003153 chemical reaction reagent Substances 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 5
- 101150003085 Pdcl gene Proteins 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 claims 1
- BEUQXVWXFDOSAQ-UHFFFAOYSA-N 2-methyl-2-[4-[2-(5-methyl-2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]pyrazol-1-yl]propanamide Chemical compound CC(C)N1N=C(C)N=C1C1=CN(CCOC=2C3=CC=C(C=2)C2=CN(N=C2)C(C)(C)C(N)=O)C3=N1 BEUQXVWXFDOSAQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000012445 acidic reagent Substances 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims 1
- 239000011521 glass Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- KMZGTOZTSHNTTM-UHFFFAOYSA-N n'-(propan-2-ylamino)ethanimidamide Chemical compound CC(C)NN=C(C)N KMZGTOZTSHNTTM-UHFFFAOYSA-N 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (47)
1. Способ получения (2-(4-(2-(1-изопропил-3-метил-1Н-1,2,4-триазол-5-ил)-5,6-дигидробензо[f]имидазо[1,2-d][1,4]оксазепин-9-ил)-1Н-пиразол-1-ил)-2-метилпропанамида I, имеющего структуру:
и его стереоизомеров, геометрических изомеров, таутомеров и фармацевтически приемлемых солей, согласно которому:
(a) подвергают взаимодействию IV и 4,4,4',4',5,5,5',5'-октаметил-2,2'-би(1,3,2-диоксаборолан) с образованием 22
(b) подвергают взаимодействию 22, палладиевый катализатор и III с образованием 23
(c) подвергают взаимодействию 23 с водным основным реагентом с образованием II
(d) подвергают взаимодействию II с ацил-активирующим реагентом, затем с аммиаком с образованием I.
2. Способ по п. 1, где IV получают в ходе взаимодействия 17:
с бромирующим реагентом.
3. Способ по п. 1, где палладиевый катализатор выбран из PdCl2(PPh3)2, Pd(t-Bu)3, PdCl2 dppf CH2Cl2, Pd(PPh3)4, Pd(OAc)/PPh3, Cl2Pd[(Pet3)]2, Pd(DIPHOS)2, Cl2Pd(Bipy), [PdCl(Ph2PCH2PPh2)]2, Cl2Pd[P(o-толил)3]2, Pd2(dba)3/P(o-толил)3, Pd2(dba)/P(фурил)3, Cl2Pd[P(фурил)3]2, Cl2Pd(PMePh2)2, Cl2Pd[P(4-F-Ph)3]2, Cl2Pd[P(C6F6)3]2, Cl2Pd[P(2-COOH-Ph)(Ph)2]2, Cl2Pd[P(4-COOH-Ph)(Ph)2]2, и инкапсулированных катализаторов Pd EnCat™ 30, Pd EnCat™ TPP30 и Pd(II)EnCat™ BINAP30.
4. Способ по п. 1, где палладий отделяют от I с помощью твердого адсорбирующего акцептора палладия.
5. Способ по п. 4, где твердый адсорбирующий акцептор палладия выбран из силикагеля, стекла с контролируемым размером пор и слабосшитого полистирола.
6. Способ по любому из п.п. 1-5, где получают III, согласно которому:
(а) подвергают взаимодействию V с 2-гидроксиэтилирующим реагентом с образованием 14
(b) подвергают взаимодействию 14 с водным основным реагентом с образованием V.
7. Способ по любому из п.п. 1-5, где получают III, согласно которому:
(a) подвергают взаимодействию 28 с ацетамидином с образованием 29
(b) подвергают взаимодействию 29 с изопропилгидразином и кислотным реагентом с образованием III.
8. Способ по любому из п.п. 1-5, где получают III, согласно которому подвергают взаимодействию 28 с N'-изопропилацетогидразонамидом 6 с образованием III
9. Способ по п. 7, где получают 28, согласно которому:
(a) подвергают взаимодействию 11 с гидроксиламином с образованием 24
(b) подвергают взаимодействию 24 с этилпропиолатом с образованием 25
(c) нагревают 25 с образованием 26
(d) подвергают взаимодействию 26 с 2-гидроксиэтилирующим реагентом с образованием 27
(e) подвергают взаимодействию 27 с водным основным реагентом с образованием 28.
10. Соединение, выбранное из структур:
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361779619P | 2013-03-13 | 2013-03-13 | |
| US61/779,619 | 2013-03-13 | ||
| PCT/EP2014/054786 WO2014140073A1 (en) | 2013-03-13 | 2014-03-12 | Process for making benzoxazepin compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018109979A Division RU2018109979A (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2015138488A true RU2015138488A (ru) | 2017-04-20 |
| RU2649976C2 RU2649976C2 (ru) | 2018-04-06 |
Family
ID=50241450
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015138488A RU2649976C2 (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
| RU2018109979A RU2018109979A (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2018109979A RU2018109979A (ru) | 2013-03-13 | 2014-03-12 | Способ получения бензоксазепиновых соединений |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US9303043B2 (ru) |
| EP (3) | EP2970329A1 (ru) |
| JP (6) | JP6363120B2 (ru) |
| KR (3) | KR20180070715A (ru) |
| CN (2) | CN105377856B (ru) |
| AR (1) | AR095365A1 (ru) |
| AU (3) | AU2014230812B2 (ru) |
| BR (1) | BR112015020716A2 (ru) |
| CA (6) | CA3005112A1 (ru) |
| HK (1) | HK1215433A1 (ru) |
| IL (1) | IL240793A0 (ru) |
| MX (1) | MX2015011438A (ru) |
| NZ (1) | NZ711192A (ru) |
| RU (2) | RU2649976C2 (ru) |
| SG (2) | SG11201507394RA (ru) |
| WO (1) | WO2014140073A1 (ru) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112016009665A8 (pt) | 2013-12-16 | 2020-04-07 | Hoffmann La Roche | polimorfos, composição farmacêutica, processos para a preparação de um polimorfo e usos dos polimorfos |
| CN112062778B (zh) | 2015-07-02 | 2024-04-19 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂䓬噁唑烷酮化合物及其使用方法 |
| CN111848643A (zh) | 2015-07-02 | 2020-10-30 | 豪夫迈·罗氏有限公司 | 苯并氧氮杂*噁唑烷酮化合物及其使用方法 |
| CN105906635A (zh) * | 2016-06-08 | 2016-08-31 | 上海大学 | 全氟烷基苯并氮杂*并喹喔啉衍生物及其合成方法 |
| CN114716377A (zh) | 2016-07-29 | 2022-07-08 | 日本烟草产业株式会社 | 吡唑-酰胺化合物的制造方法 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| ES2953833T3 (es) | 2016-12-15 | 2023-11-16 | Hoffmann La Roche | La invención se refiere a procedimientos de preparación de compuestos de benzoxacepina oxazolidinona e intermedios útiles |
| CN108752237A (zh) * | 2018-07-05 | 2018-11-06 | 四川青木制药有限公司 | 一种对氨基苯甲脒盐酸盐的新制备方法 |
| US20220040324A1 (en) | 2018-12-21 | 2022-02-10 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and kinase inhibitor |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9208135D0 (en) | 1992-04-13 | 1992-05-27 | Ludwig Inst Cancer Res | Polypeptides having kinase activity,their preparation and use |
| US5846824A (en) | 1994-02-07 | 1998-12-08 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| US6274327B1 (en) | 1992-04-13 | 2001-08-14 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| ES2205944T3 (es) * | 1998-10-23 | 2004-05-01 | Dow Agrosciences Llc | Compuestos de 3-(fenil sustituido)-5-(ciclopropil sustituido)-1,2,4-triazol. |
| EP1409125B1 (en) | 2001-07-12 | 2016-04-20 | Reaxa Limited | Microencapsulated catalyst, methods of preparation and methods of use thereof |
| CA2463441A1 (en) * | 2001-10-12 | 2003-05-08 | Bayer Pharmaceuticals Corporation | Phenyl substituted 5-membered nitrogen containing heterocycles for the treatment of obesity |
| EP1945222B1 (en) | 2005-11-02 | 2012-12-26 | Bayer Pharma Aktiengesellschaft | Pyrrolo[2,1-f] [1,2,4]-triazin-4-ylamines as igf-1r kinase inhibitors for the treatment of cancer and other hyperproliferative diseases |
| PL2081937T3 (pl) | 2006-10-23 | 2013-01-31 | Sgx Pharmaceuticals Inc | Triazolopirydazynowe modulatory kinaz białkowych |
| ES2393130T3 (es) * | 2006-10-23 | 2012-12-18 | Sgx Pharmaceuticals, Inc. | Triazoles bicíclicos como moduladores de proteínas quinasas |
| ES2531002T3 (es) | 2007-01-19 | 2015-03-09 | Xcovery Inc | Compuestos inhibidores de quinasa |
| WO2009055730A1 (en) * | 2007-10-25 | 2009-04-30 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| ES2556353T3 (es) * | 2008-02-21 | 2016-01-15 | Merck Sharp & Dohme Corp. | Compuestos que son inhibidores de las ERK |
| CL2009000780A1 (es) | 2008-03-31 | 2010-01-15 | Genentech Inc | Compuestos derivados de heterociclil-pirano-heterociclilo, heterociclil-oxepina-heterociclilo, benzopirano-heterociclilo y benzoxepina-heterociclilo sustituidos; composicion farmaceutica; procedimiento de preparacion de la composicion; kit farmaceutico; y su uso en el tratamiento del cancer, mediado por la inhibicion de pi3k. |
| GB0810902D0 (en) | 2008-06-13 | 2008-07-23 | Astex Therapeutics Ltd | New compounds |
| PE20121025A1 (es) | 2009-09-28 | 2012-08-06 | Hoffmann La Roche | Compuestos de benzoxazepina como inhibidores de la p13k |
| JP5546636B2 (ja) | 2009-09-28 | 2014-07-09 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ベンゾキセピンｐｉ３ｋ阻害剤化合物及び使用方法 |
| EP2493307B1 (en) * | 2009-10-29 | 2016-04-27 | Merck Sharp & Dohme Corp. | Bridged bicyclic piperidine derivatives and methods of use thereof |
| CN102558167A (zh) * | 2010-12-29 | 2012-07-11 | 中国医学科学院药物研究所 | Gk和ppar双重激动活性的噻唑烷二酮衍生物 |
| CA2825966A1 (en) * | 2011-03-21 | 2012-09-27 | F. Hoffmann-La Roche Ag | Benzoxazepin compounds selective for pi3k p110 delta and methods of use |
| NO3175985T3 (ru) * | 2011-07-01 | 2018-04-28 | ||
| NZ702244A (en) | 2012-06-08 | 2017-06-30 | Hoffmann La Roche | Mutant selectivity and combinations of a phosphoinositide 3 kinase inhibitor compound and chemotherapeutic agents for the treatment of cancer |
-
2014
- 2014-03-12 AU AU2014230812A patent/AU2014230812B2/en not_active Ceased
- 2014-03-12 KR KR1020187016976A patent/KR20180070715A/ko not_active Application Discontinuation
- 2014-03-12 CA CA3005112A patent/CA3005112A1/en not_active Abandoned
- 2014-03-12 CA CA3005118A patent/CA3005118A1/en not_active Abandoned
- 2014-03-12 CA CA2897618A patent/CA2897618A1/en not_active Abandoned
- 2014-03-12 EP EP14709314.0A patent/EP2970329A1/en not_active Withdrawn
- 2014-03-12 JP JP2015562108A patent/JP6363120B2/ja active Active
- 2014-03-12 CN CN201480015055.8A patent/CN105377856B/zh active Active
- 2014-03-12 BR BR112015020716A patent/BR112015020716A2/pt not_active Application Discontinuation
- 2014-03-12 CA CA2948763A patent/CA2948763C/en not_active Expired - Fee Related
- 2014-03-12 CN CN201810489045.8A patent/CN108929333A/zh active Pending
- 2014-03-12 KR KR1020157024484A patent/KR101821468B1/ko active IP Right Grant
- 2014-03-12 EP EP20204345.1A patent/EP3845540A1/en active Pending
- 2014-03-12 AR ARP140100904A patent/AR095365A1/es unknown
- 2014-03-12 SG SG11201507394RA patent/SG11201507394RA/en unknown
- 2014-03-12 SG SG10201706760YA patent/SG10201706760YA/en unknown
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