ES2588835T3 - Compuestos de pirazol como inhibidores de SGLT1 - Google Patents
Compuestos de pirazol como inhibidores de SGLT1Info
- Publication number
- ES2588835T3 ES2588835T3 ES13722231.1T ES13722231T ES2588835T3 ES 2588835 T3 ES2588835 T3 ES 2588835T3 ES 13722231 T ES13722231 T ES 13722231T ES 2588835 T3 ES2588835 T3 ES 2588835T3
- Authority
- ES
- Spain
- Prior art keywords
- mmol
- pyrazol
- propan
- beta
- tetra
- 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.)
- Active
Links
- 108091006277 SLC5A1 Proteins 0.000 title 1
- 102000058090 Sodium-Glucose Transporter 1 Human genes 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- -1 4- (4-Bromo-2-methylbenzyl) -5- (propan-2-yl) -1 H -pyrazol-3-yl Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XHBZKKFNCZNQFW-UHFFFAOYSA-N tert-butyl 2-ethylnonanoate Chemical compound CCCCCCCC(CC)C(=O)OC(C)(C)C XHBZKKFNCZNQFW-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000008505 β-D-glucopyranosides Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/06—Heterocyclic radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biotechnology (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261645101P | 2012-05-10 | 2012-05-10 | |
| US201261645101P | 2012-05-10 | ||
| US201361769221P | 2013-02-26 | 2013-02-26 | |
| US201361769221P | 2013-02-26 | ||
| PCT/US2013/039164 WO2013169546A1 (en) | 2012-05-10 | 2013-05-02 | Pyrazole compounds as sglt1 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2588835T3 true ES2588835T3 (es) | 2016-11-07 |
Family
ID=48428684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13722231.1T Active ES2588835T3 (es) | 2012-05-10 | 2013-05-02 | Compuestos de pirazol como inhibidores de SGLT1 |
Country Status (42)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA113086C2 (xx) * | 2012-05-10 | 2016-12-12 | Піразольні сполуки як інгібітори sglt1 | |
| TW201425326A (zh) | 2012-10-05 | 2014-07-01 | Lilly Co Eli | 新穎脲化合物 |
| TWI633113B (zh) | 2013-10-17 | 2018-08-21 | 美國禮來大藥廠 | 新穎脲化合物 |
| JO3298B1 (ar) | 2013-11-01 | 2018-09-16 | Lilly Co Eli | مشتقات جليكوبيرانوسيل-مستبدل و اندول-يوريا و استعمالاتهم كمثبطات sglt |
| AR098670A1 (es) | 2013-11-08 | 2016-06-08 | Lilly Co Eli | Inhibidor de sglt1 |
| CN110054657B (zh) | 2018-01-18 | 2021-06-29 | 亚宝药业集团股份有限公司 | 吡喃葡萄糖取代的吡唑化合物及其制备方法 |
| TWI805727B (zh) * | 2018-04-04 | 2023-06-21 | 日商日本煙草產業股份有限公司 | 經雜芳基取代之吡唑化合物及其醫藥用途 |
| EP4342466A1 (en) * | 2019-09-04 | 2024-03-27 | Japan Tobacco Inc. | Therapeutic or prophylactic method for diabetes using combination medicine |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60009929T2 (de) | 1999-08-31 | 2005-03-31 | Kissei Pharmaceutical Co., Ltd., Matsumoto | Glucopyranosyloxypyrazol-derivate, diese enthaltende arzneimittel und zwischenprodukte zu deren herstellung |
| JP4141258B2 (ja) | 2001-02-26 | 2008-08-27 | キッセイ薬品工業株式会社 | グルコピラノシルオキシピラゾール誘導体及びその医薬用途 |
| EP1400529A4 (en) | 2001-05-30 | 2007-12-19 | Kissei Pharmaceutical | GLUCOPYRANOSYLOXYPYRAZOLE DERIVATIVE, MEDICINAL COMPOSITION CONTAINING THE SAME, AND MEDICINAL AND INTERMEDIARY USE THEREOF |
| NZ538117A (en) * | 2002-08-08 | 2007-01-26 | Kissei Pharmaceutical | Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof |
| JP2004137245A (ja) | 2002-08-23 | 2004-05-13 | Kissei Pharmaceut Co Ltd | ピラゾール誘導体、それを含有する医薬組成物、その医薬用途及びその製造中間体 |
| DE102004028241B4 (de) * | 2004-06-11 | 2007-09-13 | Sanofi-Aventis Deutschland Gmbh | Neue Fluorglykosidderivate von Pyrazolen, diese Verbindungen enthaltende Arzneimittel und Herstellung dieser Arzneimittel |
| MX2008014512A (es) * | 2006-05-19 | 2008-11-27 | Taisho Pharma Co Ltd | Compuesto de c-fenil glucitol para el tratamiento de diabetes. |
| AU2008344436B2 (en) | 2007-12-27 | 2013-08-29 | Kissei Pharmaceutical Co., Ltd. | Monosebacate of pyrazole derivative |
| CN102414191B (zh) | 2009-02-23 | 2014-04-16 | 大正制药株式会社 | 4-异丙苯基山梨醇化合物作为sglt1抑制剂 |
| BR112012007349A2 (pt) * | 2009-10-02 | 2019-09-24 | Sanofi Sa | uso de composto com atividade inibidora de sglt-1/sglt-2 para produção de medicamentos para tratamento de doenças ósseas. |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| UA113086C2 (xx) * | 2012-05-10 | 2016-12-12 | Піразольні сполуки як інгібітори sglt1 |
-
2013
- 2013-02-05 UA UAA201412088A patent/UA113086C2/uk unknown
- 2013-04-23 AR ARP130101348A patent/AR090806A1/es active IP Right Grant
- 2013-04-23 JO JOP/2013/0117A patent/JO3136B1/ar active
- 2013-04-25 TW TW102114877A patent/TWI579295B/zh active
- 2013-05-02 JP JP2015511518A patent/JP6148725B2/ja active Active
- 2013-05-02 AU AU2013259946A patent/AU2013259946B2/en active Active
- 2013-05-02 AP AP2014008044A patent/AP3593A/xx active
- 2013-05-02 HU HUE13722231A patent/HUE030414T2/en unknown
- 2013-05-02 WO PCT/US2013/039164 patent/WO2013169546A1/en not_active Ceased
- 2013-05-02 US US13/875,314 patent/US8697849B2/en active Active
- 2013-05-02 RS RS20160626A patent/RS55107B1/sr unknown
- 2013-05-02 SI SI201330209A patent/SI2850084T1/sl unknown
- 2013-05-02 ME MEP-2016-121A patent/ME02405B/me unknown
- 2013-05-02 PE PE2014001716A patent/PE20142399A1/es active IP Right Grant
- 2013-05-02 EA EA201491852A patent/EA024207B1/ru not_active IP Right Cessation
- 2013-05-02 HR HRP20160804TT patent/HRP20160804T1/hr unknown
- 2013-05-02 DK DK13722231.1T patent/DK2850084T3/en active
- 2013-05-02 ES ES13722231.1T patent/ES2588835T3/es active Active
- 2013-05-02 NZ NZ700356A patent/NZ700356A/en unknown
- 2013-05-02 LT LTEP13722231.1T patent/LT2850084T/lt unknown
- 2013-05-02 CA CA2869323A patent/CA2869323C/en active Active
- 2013-05-02 EP EP13722231.1A patent/EP2850084B1/en active Active
- 2013-05-02 PT PT137222311T patent/PT2850084T/pt unknown
- 2013-05-02 BR BR112014026198-9A patent/BR112014026198B1/pt active IP Right Grant
- 2013-05-02 SG SG11201407345QA patent/SG11201407345QA/en unknown
- 2013-05-02 KR KR1020147031119A patent/KR101685779B1/ko active Active
- 2013-05-02 MX MX2014013615A patent/MX357058B/es active IP Right Grant
- 2013-05-02 MY MYPI2014703279A patent/MY177326A/en unknown
- 2013-05-02 PL PL13722231T patent/PL2850084T3/pl unknown
- 2013-05-02 IN IN7996DEN2014 patent/IN2014DN07996A/en unknown
-
2014
- 2014-02-18 US US14/182,354 patent/US9296775B2/en active Active
- 2014-09-30 TN TNP2014000410A patent/TN2014000410A1/fr unknown
- 2014-10-10 CR CR20140473A patent/CR20140473A/es unknown
- 2014-10-16 ZA ZA2014/07531A patent/ZA201407531B/en unknown
- 2014-10-22 CL CL2014002845A patent/CL2014002845A1/es unknown
- 2014-10-30 IL IL235427A patent/IL235427A/en active IP Right Grant
- 2014-11-03 DO DO2014000250A patent/DOP2014000250A/es unknown
- 2014-11-05 GT GT201400242A patent/GT201400242A/es unknown
- 2014-11-05 MA MA37501A patent/MA37501B1/fr unknown
- 2014-11-07 PH PH12014502492A patent/PH12014502492B1/en unknown
- 2014-11-07 EC ECIEPI201426088A patent/ECSP14026088A/es unknown
- 2014-11-11 CO CO14249415A patent/CO7141429A2/es unknown
-
2016
- 2016-08-11 CY CY20161100801T patent/CY1117912T1/el unknown
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