AR076516A1 - Derivados de oxa-azaespiro[3.3]heptan-6-ilo, metodo e intermediarios para su preparacion, composiciones farmaceuticas que los comprenden y su uso en el tratamiento de enfermedades mediadas por el receptor mch1. - Google Patents
Derivados de oxa-azaespiro[3.3]heptan-6-ilo, metodo e intermediarios para su preparacion, composiciones farmaceuticas que los comprenden y su uso en el tratamiento de enfermedades mediadas por el receptor mch1.Info
- Publication number
- AR076516A1 AR076516A1 ARP100101476A ARP100101476A AR076516A1 AR 076516 A1 AR076516 A1 AR 076516A1 AR P100101476 A ARP100101476 A AR P100101476A AR P100101476 A ARP100101476 A AR P100101476A AR 076516 A1 AR076516 A1 AR 076516A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- previously defined
- fluorine
- reacting
- Prior art date
Links
Classifications
-
- 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- 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
- A61K31/4245—Oxadiazoles
-
- 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
- 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
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
-
- 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
-
- 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
- A61P3/04—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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Abstract
Su uso en composiciones farmacéuticas y en el tratamiento o profilaxis de una enfermedad o trastorno relacionado con la hormona concentradora de melanina. Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable del mismo, en la cual R1 representa H, fluor, cloro, bromo, ciano, un grupo alquilo C1-3 opcionalmente sustituido con uno o más fluor, o alcoxi C1-2 opcionalmente sustituido con uno o más fluor; A representa O o S; R2 y R3 representan independientemente H, fluor, cloro, bromo, un grupo alquilo C1-4 opcionalmente sustituido con uno o más fluor, o alcoxi C1-4 opcionalmente sustituido con uno o más fluor; con la condicion de que R2 y R3 no estén localizados en posicion meta uno con relacion al otro; R4 y R5 representan independientemente H o un grupo alquilo C1-4; y X y Y representan independientemente O o CH2 con la condicion de que X e Y sean diferentes. Reivindicacion 14: Un procedimiento para la preparacion de un compuesto de acuerdo con la reivindicacion 1, que comprende a) hacer reaccionar un compuesto de formula (2) en la cual A, X, Y, R2, R3, R4 y R5 son tal como se han definido previamente con un compuesto de formula (3) en la cual R1 es tal como se ha definido previamente y L1 representa un grupo saliente opcionalmente en presencia de un solvente a una temperatura en el rango de 0 a 150sC; o b) hacer reaccionar un compuesto de formula (4) en la cual A, X, Y, R2, R3, R4 y R5 son tal como se han definido previamente con un compuesto de formula (5) en la cual R1 es tal como se ha definido previamente y L2 representa un grupo saliente en presencia de una base opcionalmente en presencia de un solvente a una temperatura en el rango de 0 a 150°C; o c) hacer reaccionar un compuesto de formula (6) en la cual X, Y, R4 y R5 son tal como se han definido previamente con un compuesto de formula (7) en la cual R1, R2, R3 y A son tal como se han definido previamente y L3 representa un grupo saliente en presencia de un solvente y opcionalmente en presencia de una base a una temperatura en el rango de 0 a 150°C; o d) hacer reaccionar un compuesto de formula (6) en la cual X, Y, R4 y R5 son tal como se han definido previamente con un compuesto de formula (12) en la cual R1, R2, R3 y A son tal como se han definido previamente en presencia de un agente reductor en un solvente apropiado. Reivindicacion 15: Un compuesto intermediario de formula (2) tal como se describe en la reivindicacion 14. Reivindicacion 16: Un compuesto intermediario de formula (4) tal como se describe en la reivindicacion 14. Reivindicacion 17: Un compuesto intermediario de formula (5) tal como se describe en la reivindicacion 14. Reivindicacion 18: Un compuesto intermediario de formula (7) tal como se describe en la reivindicacion 14. Reivindicacion 19: Un compuesto intermediario de formula (12) tal como se describe en la reivindicacion 14.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17463009P | 2009-05-01 | 2009-05-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR076516A1 true AR076516A1 (es) | 2011-06-15 |
Family
ID=42290768
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP100101476A AR076516A1 (es) | 2009-05-01 | 2010-04-30 | Derivados de oxa-azaespiro[3.3]heptan-6-ilo, metodo e intermediarios para su preparacion, composiciones farmaceuticas que los comprenden y su uso en el tratamiento de enfermedades mediadas por el receptor mch1. |
Country Status (23)
Country | Link |
---|---|
US (1) | US8110566B2 (es) |
EP (1) | EP2424870B1 (es) |
JP (1) | JP5763052B2 (es) |
KR (1) | KR20120023044A (es) |
CN (2) | CN102459279B (es) |
AR (1) | AR076516A1 (es) |
AU (1) | AU2010243341B2 (es) |
BR (1) | BRPI1014387A2 (es) |
CA (1) | CA2759230A1 (es) |
DK (1) | DK2424870T3 (es) |
ES (1) | ES2562831T3 (es) |
HR (1) | HRP20160128T1 (es) |
HU (1) | HUE026856T2 (es) |
MX (1) | MX2011011618A (es) |
PL (1) | PL2424870T3 (es) |
PT (1) | PT2424870E (es) |
RU (1) | RU2526055C2 (es) |
SA (1) | SA110310332B1 (es) |
SI (1) | SI2424870T1 (es) |
SM (1) | SMT201600041B (es) |
TW (1) | TW201100433A (es) |
UY (1) | UY32593A (es) |
WO (1) | WO2010125390A1 (es) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010507619A (ja) * | 2006-10-25 | 2010-03-11 | ノイロサーチ アクティーゼルスカブ | オキサジアゾール及びチアジアゾール化合物並びにニコチン性アセチルコリン受容体調節物質としてのその使用 |
KR20130041177A (ko) * | 2010-07-06 | 2013-04-24 | 아스트라제네카 아베 | 치료제 976 |
UY34194A (es) * | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
HU230880B1 (hu) | 2015-04-15 | 2018-11-29 | Richter Gedeon Nyrt | Indol származékok |
CN115884790A (zh) * | 2020-01-10 | 2023-03-31 | 康圣博施医药有限公司 | 药物的治疗组合以及其使用方法 |
HUP2200222A1 (hu) | 2022-06-17 | 2023-12-28 | Richter Gedeon Nyrt | MCHR1 antagonisták a Prader-Willi szindróma kezelésére |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
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RU2366652C2 (ru) * | 2002-02-01 | 2009-09-10 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Амиды аминоалкилзамещенных азетидинов, пирролидинов, пиперидинов и азепанов |
SE0202134D0 (sv) | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Therapeutic agents |
US7541477B2 (en) | 2002-07-30 | 2009-06-02 | Banyu Pharmaceutical Co., Ltd. | Antagonists to melanin-concentrating hormone receptor comprising benzimidazole derivative as active ingredient |
WO2004072018A1 (ja) | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
US20060293298A1 (en) * | 2003-04-10 | 2006-12-28 | Bamford Mark J | Compounds |
JP2007517868A (ja) | 2004-01-07 | 2007-07-05 | アストラゼネカ アクチボラグ | 治療薬i |
GB0400193D0 (en) | 2004-01-07 | 2004-02-11 | Astrazeneca Ab | Therapeutic agents |
US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
TW200538098A (en) | 2004-03-22 | 2005-12-01 | Astrazeneca Ab | Therapeutic agents |
DE602005014786D1 (de) * | 2004-07-26 | 2009-07-16 | Lilly Co Eli | Oxazolderivate als histamin-h3-rezeptor-wirkstoffe, deren herstellung und therapeutische verwendung |
JP5057982B2 (ja) | 2004-10-18 | 2012-10-24 | イーライ リリー アンド カンパニー | ヒスタミンh3受容体阻害剤、製造及び治療的使用 |
EP1828177B1 (en) | 2004-12-17 | 2008-08-13 | Eli Lilly And Company | Novel mch receptor antagonists |
WO2006068594A1 (en) | 2004-12-21 | 2006-06-29 | Astrazeneca Ab | HETEROCYCLIC MCHr1 ANTAGONISTS AND THEIR USE IN THERAPY |
JP2006176443A (ja) | 2004-12-22 | 2006-07-06 | Shionogi & Co Ltd | メラニン凝集ホルモン受容体アンタゴニスト |
WO2006130075A1 (en) | 2005-05-31 | 2006-12-07 | Astrazeneca Ab | Novel mchr1 antagonists and their use for the treatment of mchr1 mediated conditions and disorders |
US20080221107A1 (en) | 2005-07-15 | 2008-09-11 | Astrazeneca Ab | Therapeutic Agents |
WO2007078251A1 (en) | 2006-01-06 | 2007-07-12 | Astrazeneca Ab | Compounds |
US7666888B2 (en) | 2006-07-20 | 2010-02-23 | Amgen Inc. | Substituted azole aromatic heterocycles as inhibitors of 11β-HSD-1 |
WO2008020799A1 (en) | 2006-08-18 | 2008-02-21 | Astrazeneca Ab | Thienopyrimidin-4-one and thienopyridazin-7-one derivatives as mch rl antagonists |
JP5290192B2 (ja) | 2006-12-05 | 2013-09-18 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Mch−1に媒介される疾患における使用のための新規な置換されたジアザ−スピロ−ピリジノン誘導体 |
EA015559B1 (ru) | 2006-12-14 | 2011-08-30 | Эли Лилли Энд Компани | ПРОИЗВОДНЫЕ 5-[4-(АЗЕТИДИН-3-ИЛОКСИ)ФЕНИЛ]-2-ФЕНИЛ-5H-ТИАЗОЛО[5,4-c]ПИРИДИН-4-ОНА И ИХ ИСПОЛЬЗОВАНИЕ В КАЧЕСТВЕ РЕЦЕПТОРОВ MCH |
WO2008131103A2 (en) | 2007-04-17 | 2008-10-30 | Vertex Pharmaceuticals Incorporated | Drug discovery methods for aurora kinase inhibitors |
ATE519738T1 (de) | 2007-08-22 | 2011-08-15 | Hoffmann La Roche | Pyrrolidinarylether als nk3-rezeptorantagonisten |
MX2010003949A (es) | 2007-10-17 | 2010-04-30 | Sanofi Aventis | N-fenil-bipirrolidina carboxamidas sustituidas y uso terapeutico de las mismas. |
AU2009261248A1 (en) * | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diarylketoxime derivative |
-
2010
- 2010-04-28 SA SA110310332A patent/SA110310332B1/ar unknown
- 2010-04-29 MX MX2011011618A patent/MX2011011618A/es active IP Right Grant
- 2010-04-29 CA CA2759230A patent/CA2759230A1/en not_active Abandoned
- 2010-04-29 JP JP2012507821A patent/JP5763052B2/ja not_active Expired - Fee Related
- 2010-04-29 PT PT107186702T patent/PT2424870E/pt unknown
- 2010-04-29 CN CN201080031068.6A patent/CN102459279B/zh not_active Expired - Fee Related
- 2010-04-29 PL PL10718670T patent/PL2424870T3/pl unknown
- 2010-04-29 DK DK10718670.2T patent/DK2424870T3/en active
- 2010-04-29 HU HUE10718670A patent/HUE026856T2/en unknown
- 2010-04-29 TW TW099113722A patent/TW201100433A/zh unknown
- 2010-04-29 KR KR1020117028655A patent/KR20120023044A/ko not_active Application Discontinuation
- 2010-04-29 CN CN201410183568.1A patent/CN103936751A/zh active Pending
- 2010-04-29 BR BRPI1014387A patent/BRPI1014387A2/pt not_active IP Right Cessation
- 2010-04-29 ES ES10718670.2T patent/ES2562831T3/es active Active
- 2010-04-29 SI SI201031124T patent/SI2424870T1/sl unknown
- 2010-04-29 WO PCT/GB2010/050698 patent/WO2010125390A1/en active Application Filing
- 2010-04-29 EP EP10718670.2A patent/EP2424870B1/en active Active
- 2010-04-29 AU AU2010243341A patent/AU2010243341B2/en not_active Ceased
- 2010-04-29 RU RU2011147751/04A patent/RU2526055C2/ru not_active IP Right Cessation
- 2010-04-30 AR ARP100101476A patent/AR076516A1/es not_active Application Discontinuation
- 2010-04-30 UY UY0001032593A patent/UY32593A/es not_active Application Discontinuation
- 2010-04-30 US US12/771,594 patent/US8110566B2/en not_active Expired - Fee Related
-
2016
- 2016-02-04 HR HRP20160128TT patent/HRP20160128T1/hr unknown
- 2016-02-11 SM SM201600041T patent/SMT201600041B/it unknown
Also Published As
Publication number | Publication date |
---|---|
EP2424870A1 (en) | 2012-03-07 |
CN102459279B (zh) | 2014-06-25 |
PT2424870E (pt) | 2016-03-17 |
DK2424870T3 (en) | 2016-02-15 |
US20100280000A1 (en) | 2010-11-04 |
RU2526055C2 (ru) | 2014-08-20 |
WO2010125390A1 (en) | 2010-11-04 |
HRP20160128T1 (hr) | 2016-02-26 |
ES2562831T3 (es) | 2016-03-08 |
SMT201600041B (it) | 2016-02-25 |
JP5763052B2 (ja) | 2015-08-12 |
CN102459279A (zh) | 2012-05-16 |
SA110310332B1 (ar) | 2013-12-10 |
PL2424870T3 (pl) | 2016-05-31 |
AU2010243341B2 (en) | 2014-02-13 |
SI2424870T1 (sl) | 2016-03-31 |
TW201100433A (en) | 2011-01-01 |
AU2010243341A1 (en) | 2011-11-03 |
US8110566B2 (en) | 2012-02-07 |
HUE026856T2 (en) | 2016-07-28 |
EP2424870B1 (en) | 2015-12-16 |
KR20120023044A (ko) | 2012-03-12 |
CA2759230A1 (en) | 2010-11-04 |
BRPI1014387A2 (pt) | 2017-06-06 |
MX2011011618A (es) | 2011-11-18 |
JP2012525365A (ja) | 2012-10-22 |
CN103936751A (zh) | 2014-07-23 |
UY32593A (es) | 2010-11-30 |
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