PE20130046A1 - Procedimiento de sintesis y forma cristalina hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienen - Google Patents
Procedimiento de sintesis y forma cristalina hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienenInfo
- Publication number
- PE20130046A1 PE20130046A1 PE2012000695A PE2012000695A PE20130046A1 PE 20130046 A1 PE20130046 A1 PE 20130046A1 PE 2012000695 A PE2012000695 A PE 2012000695A PE 2012000695 A PE2012000695 A PE 2012000695A PE 20130046 A1 PE20130046 A1 PE 20130046A1
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- Prior art keywords
- formula
- compound
- synthesis
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- propoxi
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 238000005576 amination reaction Methods 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000001149 cognitive effect Effects 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000003863 metallic catalyst Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
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- 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
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
- C07C235/42—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 six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—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 six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—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 six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C07D209/52—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 condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
SE REFIERE A UN PROCEDIMIENTO DE SINTESIS DEL COMPUESTO DE FORMULA (I) QUE COMPRENDE: A) HACER REACCIONAR EL COMPUESTO DE FORMULA (II) CON AMONIACO A UNA TEMPERATURA SUPERIOR A 100ºC PARA FORMAR EL COMPUESTO DE FORMULA (III); B) REDUCIR EL COMPUESTO ANTERIOR EN PRESENCIA DE H Y DE UN CATALIZADOR METALICO PARA DAR LUGAR A LA AMINA BICICLICA DE FORMULA (IV); C) EL COMPUESTO DE FORMULA (IV) SE SOMETE A: i) UNA REACCION DE ACOPLAMIENTO EN PRESENCIA DE UN CARBONATO, AMINA O UN HIDROXIDO, EN UN MEDIO POLAR CONSTITUIDO POR CETONAS, ETERES, ENTRE OTROS CON UN COMPUESTO DE FORMULA (V), DONDE Y ES -CH2-HAL, HAL ES HALOGENO, ENTRE OTROS; ii) UNA AMINACION REDUCTORA EN MEDIO ACIDO CON UN COMPUESTO DE FORMULA (V´) , DONDE R´Y R´´ SON INDEPENDIENTEMENTE ALQUILO-(C1-C6), ENTRE OTROS; O iii) UNA AMINACION REDUCTORA CON UN COMPUESTO DE FORMULA (V´´), PARA DAR LUGAR A LA BASE LIBRE DEL COMPUESTO DE FORMULA (I) QUE EN PRESENCIA DE ACIDO CLORHIDRICO FORMA EL COMPUESTO DE FORMULA (I). SE REFIERE TAMBIEN A UNA FORMA CRISTALINA CARACTERIZADA POR UN DIAGRAMA DE DIFRACCION X SOBRE POLVO QUE PRESENTA LAS LINEAS DE DIFRACCION (ANGULO DE BRAGG 2 TETHA) SIGUIENTES: 16,97º, 17,84º 18,90º, 20,32º 23,87º, 27,10º, 27,86º Y 30,34º. REFERIDO ADEMAS A UNA COMPOSICION FARMACEUTICA, SIENDO UTIL PARA EL TRATAMIENTO DE TRASTORNOS COGNITIVOS Y PSICOCOMPORTAMENTALES
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1101746A FR2976285B1 (fr) | 2011-06-08 | 2011-06-08 | Procede de synthese et forme cristalline du chlorhydrate de 4-{3-[cis-hexahydrocypenta[c]pyrrol-2(1h)-yl]propoxy}benzamide ainsi que les compositions pharmaceutiques qui la contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20130046A1 true PE20130046A1 (es) | 2013-02-10 |
Family
ID=46172744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2012000695A PE20130046A1 (es) | 2011-06-08 | 2012-05-22 | Procedimiento de sintesis y forma cristalina hidrocloruro de 4-{3-[cis-hexahidrociclopenta[c]pirrol-2(1h)-il]propoxi}benzamida asi como las composiciones farmaceuticas que la contienen |
Country Status (44)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3003466B1 (fr) | 2013-03-22 | 2015-08-07 | Servier Lab | Utilisation du 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide pour le traitement des douleurs neuropathiques |
| CN103601666B (zh) * | 2013-11-28 | 2015-09-02 | 遵义医学院 | 八氢环戊烷[c]吡咯的制备方法 |
| CN104387313B (zh) * | 2014-10-22 | 2015-12-30 | 滨海博大化工有限公司 | 一种1,2-环戊二甲酰亚胺的制备方法 |
| KR101966221B1 (ko) * | 2017-06-14 | 2019-04-12 | 최상근 | 유해가스 처리 장치 |
| CN115232058A (zh) * | 2022-08-01 | 2022-10-25 | 上海巽田科技股份有限公司 | 一种格列齐特中间体1,2-环戊二甲酰胺的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US756120A (en) * | 1902-07-28 | 1904-03-29 | Krupp Gmbh | Recoil-gun with special devices for protecting the slide-tracks from dust. |
| NL132376C (es) * | 1966-02-10 | |||
| US4895840A (en) * | 1987-06-10 | 1990-01-23 | A. H. Robins Company, Incorporated | N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines |
| CN1314340A (zh) * | 2000-03-21 | 2001-09-26 | 山东省医药工业研究所 | 环戊烷酰亚胺的制备方法 |
| FR2866647B1 (fr) * | 2004-02-20 | 2006-10-27 | Servier Lab | Nouveaux derives azabicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN100424077C (zh) * | 2005-06-07 | 2008-10-08 | 台州市四维化工厂 | 一种环戊烷1，2-二酰亚胺的制备方法 |
| FR2937251B1 (fr) * | 2008-10-16 | 2011-03-18 | Servier Lab | Utilisation du 4-{3-°hexahydrocyclopenta°c!pyrrol-2(1h)-yl! propoxy}benzamide pour l'obtention de medicaments destines au traitement des troubles du sommeil |
| PA8850301A1 (es) * | 2008-11-26 | 2010-07-27 | Abbott Lab | Nuevas octahidrociclopenta[c]pirrol-4-aminas sustituidas como bloqueantes de los canales de calcio |
| FR2953515B1 (fr) * | 2009-12-09 | 2011-12-23 | Servier Lab | Nouveaux derives du type hexahydrocyclopenta[b]pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2974729B1 (fr) * | 2011-05-02 | 2013-04-19 | Servier Lab | Nouvelle association entre le 4-{3-[cis-hexahydrocyclopenta[c]pyrrol-2(1h)-yl]propoxy}benzamide et un inhibiteur de l'acetylcholinesterase et les compositions pharmaceutiques qui la contiennent |
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2011
- 2011-06-08 FR FR1101746A patent/FR2976285B1/fr not_active Expired - Fee Related
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2012
- 2012-05-22 IL IL219925A patent/IL219925A0/en unknown
- 2012-05-22 PE PE2012000695A patent/PE20130046A1/es not_active Application Discontinuation
- 2012-05-22 PH PH1/2012/000124A patent/PH12012000124A1/en unknown
- 2012-05-23 CR CR20120274A patent/CR20120274A/es unknown
- 2012-05-24 TN TNP2012000254A patent/TN2012000254A1/fr unknown
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- 2012-05-24 SG SG2012038055A patent/SG186546A1/en unknown
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- 2012-05-30 CA CA2779045A patent/CA2779045C/fr not_active Expired - Fee Related
- 2012-05-31 CU CU2012000087A patent/CU20120087A7/es unknown
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- 2012-06-01 EC ECSP12011941 patent/ECSP12011941A/es unknown
- 2012-06-04 MA MA34937A patent/MA33883B1/fr unknown
- 2012-06-05 KR KR1020120060635A patent/KR20120136296A/ko not_active Abandoned
- 2012-06-05 BR BRBR102012013573-6A patent/BR102012013573A2/pt not_active IP Right Cessation
- 2012-06-05 GE GEAP201212735A patent/GEP20156395B/en unknown
- 2012-06-06 CO CO12095647A patent/CO6580197A1/es unknown
- 2012-06-06 US US13/489,691 patent/US8664408B2/en not_active Expired - Fee Related
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- 2012-06-07 GT GT201200182A patent/GT201200182A/es unknown
- 2012-06-07 HU HUE12171118A patent/HUE028050T2/en unknown
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- 2012-06-07 JP JP2012129440A patent/JP5680022B2/ja not_active Expired - Fee Related
- 2012-06-07 EP EP12171118.8A patent/EP2532651B1/fr active Active
- 2012-06-07 ES ES12171118.8T patent/ES2554933T3/es active Active
- 2012-06-07 CL CL2012001500A patent/CL2012001500A1/es unknown
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- 2012-06-07 WO PCT/FR2012/051272 patent/WO2012168657A1/fr not_active Ceased
- 2012-06-07 ME MEP-2015-148A patent/ME02346B/me unknown
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- 2012-06-07 DK DK12171118.8T patent/DK2532651T3/en active
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- 2012-06-07 RU RU2013158817/04A patent/RU2013158817A/ru not_active Application Discontinuation
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- 2012-06-08 CN CN201210189156XA patent/CN102816102A/zh active Pending
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2013
- 2013-12-11 US US14/103,006 patent/US8952179B2/en not_active Expired - Fee Related
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2014
- 2014-02-06 US US14/174,272 patent/US20140155453A1/en not_active Abandoned
- 2014-05-27 KR KR1020140063712A patent/KR20140079346A/ko not_active Withdrawn
- 2014-10-31 JP JP2014223181A patent/JP2015044840A/ja active Pending
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