AR088043A1 - Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato - Google Patents
Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidratoInfo
- Publication number
- AR088043A1 AR088043A1 ARP120103551A ARP120103551A AR088043A1 AR 088043 A1 AR088043 A1 AR 088043A1 AR P120103551 A ARP120103551 A AR P120103551A AR P120103551 A ARP120103551 A AR P120103551A AR 088043 A1 AR088043 A1 AR 088043A1
- Authority
- AR
- Argentina
- Prior art keywords
- methyl
- aminosulfonyl
- phenyl
- thiazol
- acetamide
- Prior art date
Links
- -1 AMINOSULFONYL Chemical class 0.000 title abstract 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- IVZKZONQVYTCKC-UHFFFAOYSA-N bay 57-1293 Chemical compound N=1C(C)=C(S(N)(=O)=O)SC=1N(C)C(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 IVZKZONQVYTCKC-UHFFFAOYSA-N 0.000 abstract 3
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 3
- 229940126062 Compound A Drugs 0.000 abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 2
- UATOFRZSCHRPBG-UHFFFAOYSA-N acetamide;hydrate Chemical compound O.CC(N)=O UATOFRZSCHRPBG-UHFFFAOYSA-N 0.000 abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- HBXRPXYBMZDIQL-UHFFFAOYSA-N 1$l^{2}-borolane Chemical compound [B]1CCCC1 HBXRPXYBMZDIQL-UHFFFAOYSA-N 0.000 abstract 1
- KPAUORDXNFURBA-UHFFFAOYSA-N 2-(4-pyridin-2-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=N1 KPAUORDXNFURBA-UHFFFAOYSA-N 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Reivindicación 1: Método para sintetizar N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)fenil]acetamida caracterizado porque comprende los siguientes pasos: paso A: hacer reaccionar el compuesto A de la fórmula general (1) donde R¹ representa un grupo saliente y R² representa un residuo alquilo C₁₋₆ o un residuo cicloalquilo C₃₋₆ con un reactivo derivado de ácido borónico, borolano, borinano o ácido diborónico con eliminación de R¹-H o R¹-B(O)₂ y formación de un derivado de ácido borónico intermediario del compuesto A, donde el derivado de ácido borónico intermediario luego se hace reaccionar con el compuesto piridina B de la fórmula general (2) donde R³ representa un grupo saliente bajo condiciones básicas con el fin de obtener directamente ácido (4-piridin-2-ilfenil)acético que luego se purifica, paso B: hacer reaccionar ácido (4-piridin-2-ilfenil)acético obtenido del paso A con 4-metil-2-(metilamino)-1,3-tiazol-5-sulfonamida de la fórmula (3) con el fin de obtener N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il)-N-metil-2-[4-(2-piridinil)fenil]acetamida de la fórmula (4). Reivindicación 10: El compuesto mesilato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il)-N-metil-2-[4-(2-piridinil)-fenil]acetamida monohidrato cristalino de acuerdo con la reivindicación 9, caracterizado porque el mesilato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)-fenil]acetamida monohidrato cristalino es un polimorfo de mesilato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)-fenil]acetamida monohidrato cristalino, y el patrón de difracción de rayos X del polimorfo comprende valores de ángulo 2-q de 6,5, 12,9, 16,8, 18,9, 19,3, 19,5, 20,0, 22,4, 22,5, 23,2, 23,8, 25,5, 25,9, 28,8, 30,5, 32,7, y 35,7 grados.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11007823A EP2573086A1 (en) | 2011-09-26 | 2011-09-26 | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR088043A1 true AR088043A1 (es) | 2014-05-07 |
Family
ID=46889067
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120103551A AR088043A1 (es) | 2011-09-26 | 2012-09-26 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP190102595A AR116394A2 (es) | 2011-09-26 | 2019-09-13 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP200102938A AR120291A2 (es) | 2011-09-26 | 2020-10-23 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-triazol-2-il]n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190102595A AR116394A2 (es) | 2011-09-26 | 2019-09-13 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP200102938A AR120291A2 (es) | 2011-09-26 | 2020-10-23 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-triazol-2-il]n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US9340535B2 (es) |
| EP (3) | EP2573086A1 (es) |
| JP (2) | JP6161614B2 (es) |
| KR (4) | KR20190104249A (es) |
| CN (2) | CN103842359B (es) |
| AR (3) | AR088043A1 (es) |
| AU (2) | AU2012314536B2 (es) |
| BR (1) | BR112014003245B1 (es) |
| CA (1) | CA2791142C (es) |
| CL (1) | CL2014000149A1 (es) |
| DK (2) | DK2598501T3 (es) |
| ES (2) | ES2462492T3 (es) |
| HK (1) | HK1220978A1 (es) |
| HR (1) | HRP20140351T1 (es) |
| IL (2) | IL230152A (es) |
| IN (1) | IN2014DN01993A (es) |
| JO (2) | JO3037B1 (es) |
| MX (2) | MX371088B (es) |
| MY (2) | MY185063A (es) |
| PE (1) | PE20141148A1 (es) |
| PH (1) | PH12015502801A1 (es) |
| PL (2) | PL2602258T3 (es) |
| PT (1) | PT2598501E (es) |
| RU (2) | RU2620604C2 (es) |
| SG (1) | SG10201407430TA (es) |
| TW (2) | TWI567070B (es) |
| UA (2) | UA115317C2 (es) |
| WO (1) | WO2013045479A1 (es) |
| ZA (2) | ZA201401773B (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2573085A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(aminosulfonyl)-4methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl] acetamide mesylate monohydrate having a specific particle size distribution range and a specific surface area range |
| EP2573086A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
| PE20181804A1 (es) * | 2016-04-06 | 2018-11-19 | Innovative Molecules Gmbh | Derivados de aminotiazol utiles como agentes antiviricos |
| CN109996798B (zh) * | 2016-11-28 | 2023-05-05 | 艾库里斯有限及两合公司 | N-[5-(氨基磺酰基)-4-甲基-1,3-噻唑-2-基]-n-甲基-2-[4-(2-吡啶基)-苯基]-乙酰胺游离碱半水合物、其制造方法和用途 |
| JP7316214B2 (ja) | 2016-11-28 | 2023-07-27 | アイクリス ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | Ｎ－［５－（アミノスルホニル）－４－メチル－１，３－チアゾール－２－イル］－ｎ－メチル－２－［４－（２－ピリジニル）－フェニル］－アセトアミドの遊離塩基形のマレイン酸塩、医薬製剤、製造方法およびヘルペスウイルスの処置のためのその使用 |
| TW201825095A (zh) * | 2016-11-28 | 2018-07-16 | 德商艾庫里斯抗感染治療有限公司 | 包含n-[5-(胺基磺醯基)-4-甲基-1,3-噻唑-2-基]-n-甲基-2-[4-(2-吡啶基)-苯基]-乙醯胺之局部醫藥調配物 |
| KR102335327B1 (ko) | 2017-04-28 | 2021-12-03 | 현대자동차 주식회사 | 수냉식 이지알 쿨러 |
| US11213516B2 (en) * | 2017-06-28 | 2022-01-04 | Aicuris Gmbh & Co. Kg | Intravaginally applicable devices comprising antiviral compounds |
| AR113344A1 (es) | 2017-10-05 | 2020-04-22 | Innovative Molecules Gmbh | Enantiómeros de una serie de compuestos antivirales |
| JP7150368B2 (ja) * | 2018-07-06 | 2022-10-11 | フェーノ・セラピューティクス・カンパニー・リミテッド | チアゾール系化合物の結晶形およびその応用 |
| CA3113353A1 (en) * | 2018-09-19 | 2020-03-26 | Modernatx, Inc. | High-purity peg lipids and uses thereof |
| TW202038947A (zh) | 2018-11-28 | 2020-11-01 | 德商創新分子有限責任公司 | 在與溶瘤病毒之組合療法中治療癌症的解旋酶引子酶抑制劑 |
| WO2024047508A1 (en) | 2022-08-29 | 2024-03-07 | Assembly Biosciences, Inc. | Pharmaceutical compositions for herpes virus |
| WO2024047506A1 (en) | 2022-08-29 | 2024-03-07 | Assembly Biosciences, Inc. | A novel crystalline form of pritelivir |
| WO2024047507A1 (en) | 2022-08-29 | 2024-03-07 | Assembly Biosciences, Inc. | A novel crystalline form of pritelivir |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DOP2000000109A (es) | 1999-12-23 | 2002-08-30 | Gerald Kleymann | Derivados de tiazolilamida |
| DE10129717A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10129714A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Topische Anwendung von Thiazolylamiden |
| DE10129716A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10131128A1 (de) * | 2001-06-28 | 2003-01-16 | Bayer Ag | Sekundäre Sulfonamide |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| DE102005014248A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung von N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamid |
| JP2007314516A (ja) * | 2006-04-25 | 2007-12-06 | Daiichi Sankyo Co Ltd | ２以上の置換基を有するベンゼン化合物を含有する医薬 |
| EA200802417A1 (ru) * | 2006-06-09 | 2009-06-30 | Икос Корпорейшн | Замещенные фенилуксусные кислоты как dp-2-антагонисты |
| AR070127A1 (es) * | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
| UA103918C2 (en) * | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| EP2573086A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
| EP2573085A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(aminosulfonyl)-4methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl] acetamide mesylate monohydrate having a specific particle size distribution range and a specific surface area range |
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2011
- 2011-09-26 EP EP11007823A patent/EP2573086A1/en not_active Withdrawn
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2012
- 2012-09-21 TW TW105109173A patent/TWI567070B/zh active
- 2012-09-21 TW TW101134784A patent/TWI532739B/zh active
- 2012-09-23 JO JOP/2012/0276A patent/JO3037B1/ar active
- 2012-09-26 AU AU2012314536A patent/AU2012314536B2/en active Active
- 2012-09-26 IN IN1993DEN2014 patent/IN2014DN01993A/en unknown
- 2012-09-26 PE PE2014000390A patent/PE20141148A1/es active IP Right Grant
- 2012-09-26 UA UAA201404411A patent/UA115317C2/uk unknown
- 2012-09-26 KR KR1020197025387A patent/KR20190104249A/ko not_active Application Discontinuation
- 2012-09-26 EP EP13157396.6A patent/EP2602258B8/en active Active
- 2012-09-26 BR BR112014003245-9A patent/BR112014003245B1/pt active IP Right Grant
- 2012-09-26 DK DK12762300.7T patent/DK2598501T3/da active
- 2012-09-26 PL PL13157396T patent/PL2602258T3/pl unknown
- 2012-09-26 RU RU2014107430A patent/RU2620604C2/ru active
- 2012-09-26 KR KR1020177012548A patent/KR20170055565A/ko active Search and Examination
- 2012-09-26 CN CN201280046744.6A patent/CN103842359B/zh active Active
- 2012-09-26 MX MX2015016192A patent/MX371088B/es unknown
- 2012-09-26 WO PCT/EP2012/068938 patent/WO2013045479A1/en active Application Filing
- 2012-09-26 ES ES12762300.7T patent/ES2462492T3/es active Active
- 2012-09-26 MY MYPI2014000656A patent/MY185063A/en unknown
- 2012-09-26 ES ES13157396.6T patent/ES2466221T3/es active Active
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