BR112012023296A2 - processos e intermediários para preparar um inibidor macrocíclico de protease de hcv - Google Patents
processos e intermediários para preparar um inibidor macrocíclico de protease de hcvInfo
- Publication number
- BR112012023296A2 BR112012023296A2 BR112012023296A BR112012023296A BR112012023296A2 BR 112012023296 A2 BR112012023296 A2 BR 112012023296A2 BR 112012023296 A BR112012023296 A BR 112012023296A BR 112012023296 A BR112012023296 A BR 112012023296A BR 112012023296 A2 BR112012023296 A2 BR 112012023296A2
- Authority
- BR
- Brazil
- Prior art keywords
- preparing
- bis
- brucine
- oxo
- ephedrine
- Prior art date
Links
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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/20—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated the carbon skeleton being saturated and containing rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/06—Saturated compounds having a carboxyl group bound to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/28—Only halogen atoms, e.g. cyanuric chloride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- 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
- C07D417/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
Abstract
processos e intermediários para preparar um inibidor macrocíclico de protease de hcv. a presente invenção refere-se a um processo para preparar ácido (1r,2r)-4-oxo-1,2-ciclopentanodicarboxílico ii, pela resolução do ácido 4-oxo-1,2-ciclopentanodicarboxílico racêmico (v), sendo que o dito processo compreende: a) reagir ácido 4-oxo-1,2-ciclopentanodicarboxílico (v) com brucina ou (1r,2s)-(-)-efedrina, preparando assim o sal bis-brucina ou bis-(1r,2s)-(-)-efedrina de (v), e b) precipitar seletivamente o sal bis-brucina ou bis-(1r,2s)-(-)-efedrina de ácido (1r,2r)-4-oxo-1,2-ciclopentanodicarboxílico ii, enquanto que o sal bis-brucina ou bis-(1r,2s)-(-)-efedrina do ácido [(1s,2s)-4-oxo-1,2-ciclopentanodicarboxílico permanece em solução; c) liberar o ácido ii pela remoção de brucina ou (1r,2s)-(-)-efedrina do sal precipitado obtido na etapa (b).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10156681 | 2010-03-16 | ||
EP10156681.8 | 2010-03-16 | ||
PCT/EP2011/053957 WO2011113859A1 (en) | 2010-03-16 | 2011-03-16 | Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv |
Publications (2)
Publication Number | Publication Date |
---|---|
BR112012023296A2 true BR112012023296A2 (pt) | 2016-10-18 |
BR112012023296B1 BR112012023296B1 (pt) | 2018-07-03 |
Family
ID=42342793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112012023296-7A BR112012023296B1 (pt) | 2010-03-16 | 2011-03-16 | Processos para a preparação de ácido [(1r,2r)-4- oxo-1,2-ciclopentanodicarboxílico, lactona bicíclica e derivado de ciclopentano, bem como compostos intermediários para a preparação de um inibidor macrocíclico de protease de hcv |
Country Status (12)
Country | Link |
---|---|
US (2) | US9586893B2 (pt) |
EP (2) | EP2547645B1 (pt) |
JP (2) | JP2013522273A (pt) |
KR (1) | KR20130034012A (pt) |
CN (1) | CN103249708A (pt) |
AU (1) | AU2011229164B2 (pt) |
BR (1) | BR112012023296B1 (pt) |
CA (1) | CA2793129A1 (pt) |
IL (1) | IL221242A (pt) |
MX (1) | MX2012010678A (pt) |
RU (1) | RU2628081C2 (pt) |
WO (1) | WO2011113859A1 (pt) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130034012A (ko) * | 2010-03-16 | 2013-04-04 | 얀센 파마슈티칼즈, 인코포레이티드 | Hcv의 마크로사이클릭 프로테아제 저해제를 제조하기 위한 방법 및 중간체 |
AR087993A1 (es) * | 2011-09-22 | 2014-04-30 | Janssen Pharmaceuticals Inc | Procesos e intermediarios para la preparacion de un inhibidor macrociclico de la proteasa del hcv |
BR112017012634B1 (pt) * | 2014-12-22 | 2021-09-28 | Colgate-Palmolive Company | Amaciante de roupas em dose unitária e método de amaciamento de roupas |
MA41812A (fr) * | 2015-03-27 | 2018-01-30 | Janssen Pharmaceuticals Inc | Procédés et intermédiaires pour la préparation d'un inhibiteur de protéase macrocyclique du vhc |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL8300536A (nl) * | 1983-02-14 | 1984-09-03 | Oce Andeno Bv | Optisch actief alfa-azido-p-hydroxyfenylazijnzuur en zijn zouten alsmede de bereiding daarvan. |
JPS6124539A (ja) * | 1984-07-11 | 1986-02-03 | Sagami Chem Res Center | 光学活性(r)−2,5,12−トリヒドロキシ−1,2,3,4−テトラヒドロナフタセン−6,11−ジオン−2−カルボン酸の取得方法 |
JPH06124539A (ja) | 1992-10-08 | 1994-05-06 | Sony Corp | ディジタルvtr |
JPH08231469A (ja) * | 1995-02-23 | 1996-09-10 | Nippon Kayaku Co Ltd | シクロペンタンカルボン酸誘導体及びその製造法 |
JPH11180930A (ja) * | 1997-12-22 | 1999-07-06 | Sumitomo Chem Co Ltd | 光学活性trans−シクロブタンジカルボン酸類の製造方法 |
DE10029139A1 (de) * | 2000-06-14 | 2002-01-03 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von Amiden oder Estern |
US7608590B2 (en) | 2004-01-30 | 2009-10-27 | Medivir Ab | HCV NS-3 serine protease inhibitors |
PE20070211A1 (es) * | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
EP1919899B1 (en) * | 2005-07-29 | 2011-01-19 | Tibotec Pharmaceuticals | Macrocyclic inhibitors of hepatitis c virus |
US20070185346A1 (en) * | 2006-02-03 | 2007-08-09 | Vaidya Niteen A | Kit for automated resolving agent selection and method thereof |
TWI455936B (zh) * | 2007-02-01 | 2014-10-11 | Tibotec Pharm Ltd | 用於製備hcv之大環蛋白酶抑制劑之方法及中間物 |
KR20130034012A (ko) * | 2010-03-16 | 2013-04-04 | 얀센 파마슈티칼즈, 인코포레이티드 | Hcv의 마크로사이클릭 프로테아제 저해제를 제조하기 위한 방법 및 중간체 |
-
2011
- 2011-03-16 KR KR1020127024789A patent/KR20130034012A/ko not_active Application Discontinuation
- 2011-03-16 BR BR112012023296-7A patent/BR112012023296B1/pt not_active IP Right Cessation
- 2011-03-16 JP JP2012557537A patent/JP2013522273A/ja not_active Withdrawn
- 2011-03-16 CA CA2793129A patent/CA2793129A1/en not_active Abandoned
- 2011-03-16 MX MX2012010678A patent/MX2012010678A/es active IP Right Grant
- 2011-03-16 RU RU2012143977A patent/RU2628081C2/ru not_active IP Right Cessation
- 2011-03-16 WO PCT/EP2011/053957 patent/WO2011113859A1/en active Application Filing
- 2011-03-16 US US13/634,996 patent/US9586893B2/en not_active Expired - Fee Related
- 2011-03-16 AU AU2011229164A patent/AU2011229164B2/en not_active Ceased
- 2011-03-16 CN CN2011800140694A patent/CN103249708A/zh active Pending
- 2011-03-16 EP EP11709692.5A patent/EP2547645B1/en active Active
- 2011-03-16 EP EP17166514.4A patent/EP3239129A1/en not_active Withdrawn
-
2012
- 2012-08-01 IL IL221242A patent/IL221242A/en not_active IP Right Cessation
-
2016
- 2016-02-08 JP JP2016021576A patent/JP2016164143A/ja active Pending
-
2017
- 2017-02-10 US US15/429,250 patent/US20170152253A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP2547645B1 (en) | 2018-07-04 |
JP2016164143A (ja) | 2016-09-08 |
AU2011229164B2 (en) | 2015-11-26 |
WO2011113859A1 (en) | 2011-09-22 |
US20130005976A1 (en) | 2013-01-03 |
MX2012010678A (es) | 2012-10-15 |
BR112012023296B1 (pt) | 2018-07-03 |
US20170152253A1 (en) | 2017-06-01 |
US9586893B2 (en) | 2017-03-07 |
RU2012143977A (ru) | 2014-04-27 |
IL221242A (en) | 2016-04-21 |
RU2628081C2 (ru) | 2017-08-14 |
CN103249708A (zh) | 2013-08-14 |
EP3239129A1 (en) | 2017-11-01 |
KR20130034012A (ko) | 2013-04-04 |
CA2793129A1 (en) | 2011-09-22 |
EP2547645A1 (en) | 2013-01-23 |
JP2013522273A (ja) | 2013-06-13 |
AU2011229164A1 (en) | 2012-08-30 |
IL221242A0 (en) | 2012-10-31 |
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