CN103370307B - 磺酰胺化合物及其制备方法和使用方法 - Google Patents
磺酰胺化合物及其制备方法和使用方法 Download PDFInfo
- Publication number
- CN103370307B CN103370307B CN201180059472.9A CN201180059472A CN103370307B CN 103370307 B CN103370307 B CN 103370307B CN 201180059472 A CN201180059472 A CN 201180059472A CN 103370307 B CN103370307 B CN 103370307B
- Authority
- CN
- China
- Prior art keywords
- thiophene
- methyl
- formic acid
- ethyl
- carboxylic acid
- 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.)
- Expired - Fee Related
Links
- 0 CC1=C(C(O)=O)C(*)=C(*)*1 Chemical compound CC1=C(C(O)=O)C(*)=C(*)*1 0.000 description 9
- PJUOFONAPPGUGM-UHFFFAOYSA-N CCOC(c1c(NS(c(cccc2)c2OC)(=O)=O)[s]c2c1CCCC2)=O Chemical compound CCOC(c1c(NS(c(cccc2)c2OC)(=O)=O)[s]c2c1CCCC2)=O PJUOFONAPPGUGM-UHFFFAOYSA-N 0.000 description 1
- QMRKXWQCFMNAGX-UHFFFAOYSA-N CCOC(c1c(NS(c2ccccc2)=O)[s]c(Br)c1C)=O Chemical compound CCOC(c1c(NS(c2ccccc2)=O)[s]c(Br)c1C)=O QMRKXWQCFMNAGX-UHFFFAOYSA-N 0.000 description 1
- LUEJHLQTHRSINK-UHFFFAOYSA-O CCOC(c1c(N[S+](c(cc2)ccc2F)(=O)=O)[s]c2c1CCCC2)=[OH+] Chemical compound CCOC(c1c(N[S+](c(cc2)ccc2F)(=O)=O)[s]c2c1CCCC2)=[OH+] LUEJHLQTHRSINK-UHFFFAOYSA-O 0.000 description 1
- JWZIERIVRSHTFF-UHFFFAOYSA-N COC(c1c(NCc2ccccc2)[s]c2c1CCCO2)=O Chemical compound COC(c1c(NCc2ccccc2)[s]c2c1CCCO2)=O JWZIERIVRSHTFF-UHFFFAOYSA-N 0.000 description 1
- FHTVFVGFQKFZLA-UHFFFAOYSA-N COc1cccc(SNc2c(C(O)=O)c(CCCC3)c3[s]2)c1 Chemical compound COc1cccc(SNc2c(C(O)=O)c(CCCC3)c3[s]2)c1 FHTVFVGFQKFZLA-UHFFFAOYSA-N 0.000 description 1
- SAIHZPLWUGMAHZ-UHFFFAOYSA-N Cc1c(C)[s]c2c1C1CC2CC1 Chemical compound Cc1c(C)[s]c2c1C1CC2CC1 SAIHZPLWUGMAHZ-UHFFFAOYSA-N 0.000 description 1
- GXVJTPIDZGSSOY-UHFFFAOYSA-N Cc1c(C)[s]c2c1C1OC2CC1 Chemical compound Cc1c(C)[s]c2c1C1OC2CC1 GXVJTPIDZGSSOY-UHFFFAOYSA-N 0.000 description 1
- AITYRBHXIKFAEE-UHFFFAOYSA-N Cc1c(C)[s]c2c1COCC2 Chemical compound Cc1c(C)[s]c2c1COCC2 AITYRBHXIKFAEE-UHFFFAOYSA-N 0.000 description 1
- DIKASPZKNNUUMB-UHFFFAOYSA-N OC(c1c(NS(c(cccc2)c2Cl)(=O)=O)[s]c2c1CCCC2)=O Chemical compound OC(c1c(NS(c(cccc2)c2Cl)(=O)=O)[s]c2c1CCCC2)=O DIKASPZKNNUUMB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39210810P | 2010-10-12 | 2010-10-12 | |
| US61/392,108 | 2010-10-12 | ||
| US42005010P | 2010-12-06 | 2010-12-06 | |
| US61/420,050 | 2010-12-06 | ||
| PCT/US2011/055987 WO2012051318A1 (en) | 2010-10-12 | 2011-10-12 | Sulphonamide compounds and methods of making and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103370307A CN103370307A (zh) | 2013-10-23 |
| CN103370307B true CN103370307B (zh) | 2016-05-25 |
Family
ID=44903376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180059472.9A Expired - Fee Related CN103370307B (zh) | 2010-10-12 | 2011-10-12 | 磺酰胺化合物及其制备方法和使用方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9221787B2 (https=) |
| EP (1) | EP2627632A1 (https=) |
| JP (1) | JP5913333B2 (https=) |
| KR (1) | KR20140026330A (https=) |
| CN (1) | CN103370307B (https=) |
| AU (1) | AU2011316550A1 (https=) |
| BR (1) | BR112013008856A2 (https=) |
| CA (1) | CA2814413A1 (https=) |
| MX (1) | MX339201B (https=) |
| WO (1) | WO2012051318A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023026121A1 (en) * | 2021-08-23 | 2023-03-02 | Natural Academy S.R.L. | Medical liquid composition for aerial administration |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010065877A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Methods of treating an overweight or obese subject |
| US8642650B2 (en) | 2008-12-04 | 2014-02-04 | Zafgen, Inc. | Methods of treating an overweight or obese subject |
| WO2013055385A2 (en) | 2011-10-03 | 2013-04-18 | Zafgen Corporation | Methods of treating age related disorders |
| CA2777108A1 (en) | 2009-10-09 | 2011-04-14 | Zafgen Corporation | Sulphone compounds and methods of making and using same |
| US8815309B2 (en) | 2010-01-08 | 2014-08-26 | Zafgen, Inc. | Methods of treating a subject with benign prostate hyperplasia |
| BR112012016793A2 (pt) | 2010-01-08 | 2018-07-31 | Zafgen Corp | compostos tipo fumagilol e métodos de fazer e usar os mesmos |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| CN103249735B (zh) | 2010-07-22 | 2016-04-06 | 扎夫根股份有限公司 | 三环化合物及其制备和使用方法 |
| US9173865B2 (en) | 2010-11-29 | 2015-11-03 | Zafgen, Inc. | Treatment of obesity using non-daily administration of 6-O-(4-dimethylaminoethoxy) cinnamoyl fumagillol |
| MX344238B (es) | 2011-01-26 | 2016-12-07 | Zafgen Inc | Compuestos de tetrazol y métodos para preparar y usar los mismos. |
| EP2683706B1 (en) | 2011-03-08 | 2018-02-21 | Zafgen, Inc. | Oxaspiro [2.5]octane derivatives and analogs |
| EP2705036B1 (en) | 2011-05-06 | 2015-08-12 | Zafgen Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
| CN103764641B (zh) | 2011-05-06 | 2016-10-26 | 扎夫根股份有限公司 | 部分饱和的三环化合物及其制备和使用方法 |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| MX2014008706A (es) | 2012-01-18 | 2015-03-05 | Zafgen Inc | Compuestos tricíclicos de sulfonamida y métodos para elaborarlos y usarlos. |
| JP2015509102A (ja) | 2012-01-18 | 2015-03-26 | ザフゲン，インコーポレイテッド | 三環式スルホン化合物並びにその作製および使用方法 |
| MX2014013599A (es) | 2012-05-08 | 2015-05-11 | Zafgen Inc | Tratamiento de la obesidad hipotalamica con inhibidores de metap2. |
| BR112014027981A2 (pt) | 2012-05-09 | 2017-06-27 | Zafgen Inc | compostos do tipo fumagilol e métodos de produção e utilização dos mesmos |
| MX2015005733A (es) | 2012-11-05 | 2016-02-10 | Zafgen Inc | Compuestos triciclicos para usarse en el tratamiento y/o control de obesidad. |
| AU2013337282A1 (en) | 2012-11-05 | 2015-05-21 | Zafgen, Inc. | Tricyclic compounds and methods of making and using same |
| NZ707773A (en) | 2012-11-05 | 2019-05-31 | Zafgen Inc | Methods of treating liver diseases |
| CN105228610A (zh) | 2013-03-14 | 2016-01-06 | 扎夫根股份有限公司 | 治疗肾疾病和其它病症的方法 |
| WO2015184214A1 (en) | 2014-05-30 | 2015-12-03 | Dow Corning Corporation | Process of synthesizing diisopropylaminw-disilanes |
| JPWO2016039403A1 (ja) * | 2014-09-11 | 2017-06-29 | 塩野義製薬株式会社 | 持続性ｈｉｖプロテアーゼ阻害剤 |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| WO2023212095A1 (en) * | 2022-04-27 | 2023-11-02 | The Regents Of The University Of California | Molecules that enhance extracellular vesicle release |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080312231A1 (en) * | 2007-04-30 | 2008-12-18 | Gruenenthal Gmbh | Substituted Sulfonamide Compounds |
| WO2010065879A2 (en) * | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Methods of treating an overweight or obese subject |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6551611B2 (en) * | 1995-09-28 | 2003-04-22 | Schering Aktiengesellschaft | Hormone replacement therapy method |
| US7491718B2 (en) | 2002-10-08 | 2009-02-17 | Abbott Laboratories | Sulfonamides having antiangiogenic and anticancer activity |
| EP2220065A2 (en) * | 2007-07-30 | 2010-08-25 | Encysive Pharmaceuticals, Inc. | Modulators of ccr9 receptor and methods of use thereof |
| EP2227466B1 (de) | 2007-11-30 | 2011-04-20 | Bayer Schering Pharma Aktiengesellschaft | Heteroaryl-substituierte piperidine |
| CA2777108A1 (en) | 2009-10-09 | 2011-04-14 | Zafgen Corporation | Sulphone compounds and methods of making and using same |
| CN103249735B (zh) | 2010-07-22 | 2016-04-06 | 扎夫根股份有限公司 | 三环化合物及其制备和使用方法 |
| MX344238B (es) | 2011-01-26 | 2016-12-07 | Zafgen Inc | Compuestos de tetrazol y métodos para preparar y usar los mismos. |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| CN103764641B (zh) | 2011-05-06 | 2016-10-26 | 扎夫根股份有限公司 | 部分饱和的三环化合物及其制备和使用方法 |
| EP2705036B1 (en) | 2011-05-06 | 2015-08-12 | Zafgen Inc. | Tricyclic sulfonamide compounds and methods of making and using same |
-
2011
- 2011-10-12 US US13/878,958 patent/US9221787B2/en not_active Expired - Fee Related
- 2011-10-12 EP EP11773159.6A patent/EP2627632A1/en not_active Withdrawn
- 2011-10-12 AU AU2011316550A patent/AU2011316550A1/en not_active Abandoned
- 2011-10-12 MX MX2013004079A patent/MX339201B/es active IP Right Grant
- 2011-10-12 KR KR1020137012153A patent/KR20140026330A/ko not_active Withdrawn
- 2011-10-12 CA CA2814413A patent/CA2814413A1/en not_active Abandoned
- 2011-10-12 BR BR112013008856A patent/BR112013008856A2/pt not_active IP Right Cessation
- 2011-10-12 JP JP2013533977A patent/JP5913333B2/ja active Active
- 2011-10-12 CN CN201180059472.9A patent/CN103370307B/zh not_active Expired - Fee Related
- 2011-10-12 WO PCT/US2011/055987 patent/WO2012051318A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080312231A1 (en) * | 2007-04-30 | 2008-12-18 | Gruenenthal Gmbh | Substituted Sulfonamide Compounds |
| WO2010065879A2 (en) * | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Methods of treating an overweight or obese subject |
Non-Patent Citations (16)
| Title |
|---|
| ACS.RN：1094564-42-7、1094433-94-9、1094363-75-3.《STN registry数据库》.2008,1-12. * |
| Discovery and Optimization of Anthranilic Acid Sulfonamides as Inhibitors of Methionine Aminopeptidase-2: A Structural Basis for the Reduction of Albumin Binding;George S.Sheppard等;《J. Med. Chem.》;20060608;第49卷(第13期);第3833、3837页表1-2 * |
| Discovery of thiophene-2-carboxylic acids as potent inhibitors of HCV NS5B polymerase and HCV subgenomic RNA replication. Part 1: Sulfonamides;Laval Chan等;《Bioorganic & Medicinal Chemistry Letters》;20040209;第14卷(第3期);第795页表2化合物13 * |
| Functional dericatives of thipohene;V.I.Shvedov等;《Chemistry of heterocyclic compounds》;19770201;第13卷(第2期);第163页化合物VIII、IX * |
| RN：1094564-42-7、1094433-94-9、1094363-75-3;ACS;《STN registry数据库》;20080824;1-12 * |
| RN：1095612-95-5、1095490-31-5;ACS;《STN registry数据库》;20090123;1-7 * |
| RN：1096270-39-1;ACS;《STN registry数据库》;20090127;1-3 * |
| RN：1097113-05-7、1097090-94-2、1096977-17-1、1096977-16-0、1096977-14-8、1096954-77-6、1096918-10-3、1096918-09-0;ACS;《STN registry数据库》;20090128;1-25 * |
| RN：1152881-48-5;ACS;《STN registry数据库》;20090607;1-4 * |
| RN：1182796-27-5;ACS;《STN registry数据库》;20090911;1-3 * |
| RN：1184405-12-6;ACS;《STN registry数据库》;20090915;1-3 * |
| RN：1216027-71-2;ACS;《STN registry数据库》;20100404;1-4 * |
| RN：331750-29-9;ACS;《STN registry数据库》;20010418;1-6 * |
| RN：777898-41-6、777898-25-6、777898-13-2、777898-01-8、777897-84-4、777897-82-2、777897-80-0、777897-79-7;ACS;《STN registry数据库》;20041110;1-26 * |
| RN：926272-10-8、926263-03-8、926250-15-9、926240-26-8、926231-41-6、926228-24-2、926226-88-2、926221-98-9、926214-20-2、926213-93-6、926206-42-0、926195-98-4、926194-72-1;ACS;《STN registry数据库》;20070313;1-47 * |
| RN：930000-60-5、929984-82-7;ACS;《STN registry数据库》;20070413;1-7 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023026121A1 (en) * | 2021-08-23 | 2023-03-02 | Natural Academy S.R.L. | Medical liquid composition for aerial administration |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2627632A1 (en) | 2013-08-21 |
| JP5913333B2 (ja) | 2016-04-27 |
| JP2013539789A (ja) | 2013-10-28 |
| MX339201B (es) | 2016-05-13 |
| AU2011316550A1 (en) | 2013-05-02 |
| CA2814413A1 (en) | 2012-04-19 |
| US20130217759A1 (en) | 2013-08-22 |
| CN103370307A (zh) | 2013-10-23 |
| BR112013008856A2 (pt) | 2016-06-21 |
| KR20140026330A (ko) | 2014-03-05 |
| WO2012051318A1 (en) | 2012-04-19 |
| MX2013004079A (es) | 2013-10-25 |
| WO2012051318A8 (en) | 2013-05-23 |
| US9221787B2 (en) | 2015-12-29 |
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