CA2551867C - Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives - Google Patents

Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives Download PDF

Info

Publication number
CA2551867C
CA2551867C CA2551867A CA2551867A CA2551867C CA 2551867 C CA2551867 C CA 2551867C CA 2551867 A CA2551867 A CA 2551867A CA 2551867 A CA2551867 A CA 2551867A CA 2551867 C CA2551867 C CA 2551867C
Authority
CA
Canada
Prior art keywords
optionally substituted
alkoxy
aryl
compound
imidazo
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
Application number
CA2551867A
Other languages
English (en)
French (fr)
Other versions
CA2551867A1 (en
Inventor
Kevin N. Winzenberg
Craig L. Francis
David G. Sawutz
Ashit Ganguly
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2551867A1 publication Critical patent/CA2551867A1/en
Application granted granted Critical
Publication of CA2551867C publication Critical patent/CA2551867C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Plant Pathology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Agronomy & Crop Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2551867A 2003-12-31 2004-12-22 Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives Expired - Fee Related CA2551867C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US53372903P 2003-12-31 2003-12-31
US60/533,729 2003-12-31
PCT/US2004/043402 WO2005066177A1 (en) 2003-12-31 2004-12-22 Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives

Publications (2)

Publication Number Publication Date
CA2551867A1 CA2551867A1 (en) 2005-07-21
CA2551867C true CA2551867C (en) 2010-08-17

Family

ID=34748949

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2551867A Expired - Fee Related CA2551867C (en) 2003-12-31 2004-12-22 Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives

Country Status (15)

Country Link
US (1) US7759349B2 (enExample)
EP (1) EP1699799B1 (enExample)
JP (1) JP4758909B2 (enExample)
KR (1) KR20060110344A (enExample)
CN (1) CN100582108C (enExample)
AT (1) ATE362475T1 (enExample)
AU (1) AU2004312506B2 (enExample)
BR (1) BRPI0418328A (enExample)
CA (1) CA2551867C (enExample)
DE (1) DE602004006536T2 (enExample)
ES (1) ES2285565T3 (enExample)
NZ (1) NZ548098A (enExample)
PL (1) PL380764A1 (enExample)
WO (1) WO2005066177A1 (enExample)
ZA (1) ZA200605299B (enExample)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7943160B2 (en) * 2002-05-09 2011-05-17 Scimetrics Limited Corp. Pest control methods
CN101065352A (zh) 2004-09-23 2007-10-31 先灵-普劳有限公司 使用新的三氟甲磺酰苯胺肟醚衍生物控制动物中的寄生虫
DE602005017419D1 (de) 2004-11-19 2009-12-10 Schering Plough Ltd Kontrolle von parasiten bei tieren mittels verwendung von parasitiziden 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitril-derivaten
WO2006070943A1 (ja) * 2004-12-28 2006-07-06 Takeda Pharmaceutical Company Limited 縮合イミダゾール化合物およびその用途
US20060281695A1 (en) * 2005-06-09 2006-12-14 Schering-Plough Animal Health Corporation Control of parasites in animals by N-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and N-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives
US7750000B2 (en) 2005-09-02 2010-07-06 Bayer Schering Pharma Ag Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments
DE102005042742A1 (de) * 2005-09-02 2007-03-08 Schering Ag Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel
US8119667B2 (en) * 2005-12-29 2012-02-21 Schering-Plough Animal Health Corporation Carbonates of fenicol antibiotics
TW200803903A (en) * 2006-04-28 2008-01-16 Nihon Mediphysics Co Ltd Novel compound having affinity to amyloid
KR20090010987A (ko) 2006-05-19 2009-01-30 니혼 메디피직스 가부시키가이샤 신규 아밀로이드 친화성 화합물
DE102006029447A1 (de) * 2006-06-21 2007-12-27 Bayer Schering Pharma Ag Oxo-substituierte Imidazo[1,2b]pyridazine, deren Herstellung und Verwendung als Arzneimittel
KR20090025282A (ko) * 2006-06-21 2009-03-10 니혼 메디피직스 가부시키가이샤 신규 아밀로이드 친화성 화합물
US8044049B2 (en) * 2006-08-04 2011-10-25 Takeda Pharmaceutical Company Limited Fused heterocyclic derivative and use thereof
EP2098522B1 (en) * 2006-11-30 2011-10-19 Nihon Medi-Physics Co., Ltd. Compounds having affinity for amyloid
US8084643B2 (en) * 2006-12-13 2011-12-27 Intervet Inc. Water-soluble prodrugs of florfenicol and its analogs
EP2102154A1 (en) * 2006-12-13 2009-09-23 Schering-Plough Ltd. Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof
WO2008072682A1 (ja) * 2006-12-15 2008-06-19 Daiichi Sankyo Company, Limited イミダゾ［１，２－ｂ］ピリダジン誘導体
EP2119458B9 (en) 2007-02-13 2013-08-21 Nihon Medi-Physics Co., Ltd. Method for production of radiation diagnostic imaging agent
WO2008133192A1 (ja) * 2007-04-19 2008-11-06 Takeda Pharmaceutical Company Limited 縮合イミダゾール化合物およびその用途
TWI430995B (zh) 2007-06-26 2014-03-21 Du Pont 萘異唑啉無脊椎有害動物控制劑
EP2957284B1 (en) 2007-06-27 2018-01-17 E. I. du Pont de Nemours and Company Animal pest control method
ES2375425T3 (es) * 2007-07-26 2012-02-29 Novartis Ag Compuestos org�?nicos.
TWI556741B (zh) 2007-08-17 2016-11-11 英特威特國際股份有限公司 異唑啉組成物及其作為抗寄生蟲藥上的應用
US20100249418A1 (en) * 2007-10-24 2010-09-30 Nihon Medi-Physics Co., Ltd. Novel compound having affinity for amyloid
WO2009057576A1 (ja) * 2007-10-30 2009-05-07 Nihon Medi-Physics Co., Ltd. 新規アミロイド親和性化合物の使用及び製造方法
CN101909659A (zh) * 2007-10-30 2010-12-08 日本医事物理股份有限公司 对淀粉样蛋白具有亲和性的新化合物的应用及制备方法
US7868001B2 (en) 2007-11-02 2011-01-11 Hutchison Medipharma Enterprises Limited Cytokine inhibitors
TWI491610B (zh) * 2008-10-09 2015-07-11 必治妥美雅史谷比公司 作為激酶抑制劑之咪唑并嗒腈
UA110924C2 (uk) 2009-08-05 2016-03-10 Е. І. Дю Пон Де Немур Енд Компані Мезоіонні пестициди
CN102574815A (zh) 2009-08-05 2012-07-11 杜邦公司 介离子杀虫剂
KR20120050467A (ko) 2009-08-05 2012-05-18 이 아이 듀폰 디 네모아 앤드 캄파니 메소이온성 살충제
US20120295931A1 (en) 2010-02-05 2012-11-22 Lutz Juergen Spiroindoline compounds for use as anthelminthics
ES2624845T3 (es) 2010-09-29 2017-07-17 Intervet International B.V. Compuestos de N-heteroarilo con unidad de puente cíclico para el tratamiento de enfermedades parasitarias
RU2596185C2 (ru) 2010-09-29 2016-08-27 Интервет Интернэшнл Б.В. N-гетероарильные соединения
WO2012087630A1 (en) 2010-12-20 2012-06-28 E.I. Du Pont De Nemours And Company Pyridine and pyrimidine compounds for controlling invertebrate
TWI617559B (zh) * 2010-12-22 2018-03-11 江蘇恆瑞醫藥股份有限公司 ２－芳基咪唑并［１，２－ｂ］嗒．２－苯基咪唑并［１，２－ａ］吡啶，和２－苯基咪唑并［１，２－ａ］吡衍生物
KR20140038527A (ko) 2011-06-20 2014-03-28 이 아이 듀폰 디 네모아 앤드 캄파니 연충 감염을 치료하기 위한 복소환식 화합물
WO2013017678A1 (en) 2011-08-04 2013-02-07 Intervet International B.V. Novel spiroindoline compounds
SG11201402664VA (en) 2011-11-28 2014-06-27 Du Pont N- (4 -quinolinylmethyl) sulfonamide derivatives and their use as anthelmintics
US9260441B2 (en) 2012-03-28 2016-02-16 Intervet Inc. Heteroaryl compounds with cyclic bridging unit
AU2013241853B2 (en) 2012-03-28 2017-11-09 Intervet International B.V. Heteroaryl compounds with A-cyclic bridging unit
WO2013158422A1 (en) 2012-04-17 2013-10-24 E. I. Du Pont De Nemours And Company Heterocyclic compounds for controlling invertebrate pests
WO2014099837A1 (en) 2012-12-18 2014-06-26 E. I. Du Pont De Nemours And Company Sulfonamide anthelmintics
US10188108B2 (en) 2015-04-08 2019-01-29 Bayer Cropscience Aktiengesellschaft Fused bicyclic heterocycle derivatives as pesticides
JP6913076B2 (ja) 2015-08-07 2021-08-04 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 有害生物防除剤としての２−（ヘタ）アリール−置換縮合ヘテロ環誘導体
RU2018119344A (ru) 2015-10-26 2019-11-28 Байер Кропсайенс Акциенгезельшафт Конденсированные бициклические гетероциклические производные в качестве средства для борьбы с вредителями
WO2017093180A1 (de) 2015-12-01 2017-06-08 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2017144341A1 (de) 2016-02-23 2017-08-31 Bayer Cropscience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2017174414A1 (de) 2016-04-05 2017-10-12 Bayer Cropscience Aktiengesellschaft Naphthalin-derivate als schädlingsbekämpfungsmittel
EP3241830A1 (de) 2016-05-04 2017-11-08 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
BR112019001135B1 (pt) * 2016-07-19 2022-11-01 Bayer Cropscience Aktiengesellschaft Derivados de heterociclo bicíclico fundido como pesticidas, seu uso, formulação agroquímica, e método para controlar pragas animais
MA45918A (fr) 2016-08-15 2019-06-19 Bayer Ag Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
CN109963860A (zh) 2016-09-19 2019-07-02 拜耳作物科学股份公司 吡唑并[1,5-a]吡啶衍生物及其作为农药的用途
WO2018065288A1 (de) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz
TW201837026A (zh) 2017-01-10 2018-10-16 德商拜耳廠股份有限公司 作為除害劑之雜環衍生物（二）
UY37556A (es) 2017-01-10 2018-07-31 Bayer Ag Derivados heterocíclicos como pesticidas
GB201700692D0 (en) * 2017-01-16 2017-03-01 Salvensis Novel compounds and their use in the treatment of schistosomiasis
WO2018138050A1 (de) 2017-01-26 2018-08-02 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
CN110582503B (zh) 2017-04-24 2022-05-31 拜耳公司 作为有害物防治剂的稠合双环杂环化合物衍生物
EP3305786A3 (de) 2018-01-22 2018-07-25 Bayer CropScience Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
EP3755700B1 (de) 2018-02-21 2021-11-24 Bayer Aktiengesellschaft Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel
WO2020002593A1 (en) 2018-06-29 2020-01-02 Intervet International B.V. Compound for use against helminthic infection
PE20211275A1 (es) 2018-07-09 2021-07-19 Boehringer Ingelheim Animal Health Usa Inc Compuestos heterociclicos antihelminticos
BR112021010430A2 (pt) 2019-02-26 2021-08-24 Bayer Aktiengesellschaft Derivados de heterociclo bicíclico fundido como pesticidas
MX2021010217A (es) 2019-02-26 2021-09-21 Bayer Ag Derivados heterociclos biciclicos condensados como plaguicida.
KR20220002890A (ko) 2019-03-19 2022-01-07 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물
JP7644121B2 (ja) 2019-12-18 2025-03-11 インターベット インターナショナル ベー． フェー． アザインドール構造を含む駆虫剤化合物
US20230148316A1 (en) 2019-12-18 2023-05-11 Intervet Inc. Anthelmintic compounds comprising a quinoline structure
MX2022015038A (es) * 2020-05-29 2023-01-04 Boehringer Ingelheim Animal Health Usa Inc Compuestos heterociclicos como anthelminticos.
US20240043446A1 (en) 2020-12-11 2024-02-08 Intervet Inc. Anthelmintic compounds comprising a thienopyridine structure
GB202019622D0 (en) * 2020-12-11 2021-01-27 Adorx Therapeutics Ltd Antagonist compounds
WO2025027117A1 (en) 2023-08-02 2025-02-06 Intervet International B.V. Carboxamide-4-quinoline compounds with anthelmintic activity

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725407A (en) * 1971-04-08 1973-04-03 American Cyanamid Co 6-substituted amino-3-nitroimidazo(1,2-b)pyridazines and methods of preparing the same
US3905974A (en) * 1972-09-28 1975-09-16 American Cyanamid Co 6-Substituted oxo and thio-3-nitroimidazo(1,2-b)-pyridazines and methods of preparing same
DD202692A5 (de) 1979-12-04 1983-09-28 Ciba Geigy Verfahren zur herstellung neuer derivate des 2-amino-aethanols

Also Published As

Publication number Publication date
AU2004312506B2 (en) 2011-08-04
KR20060110344A (ko) 2006-10-24
AU2004312506A1 (en) 2005-07-21
EP1699799B1 (en) 2007-05-16
US7759349B2 (en) 2010-07-20
CN100582108C (zh) 2010-01-20
ZA200605299B (en) 2007-03-28
EP1699799A1 (en) 2006-09-13
PL380764A1 (pl) 2007-03-19
WO2005066177A1 (en) 2005-07-21
CN1922181A (zh) 2007-02-28
JP2007517043A (ja) 2007-06-28
DE602004006536T2 (de) 2008-01-31
US20050182059A1 (en) 2005-08-18
HK1091207A1 (en) 2007-01-12
ATE362475T1 (de) 2007-06-15
ES2285565T3 (es) 2007-11-16
DE602004006536D1 (de) 2007-06-28
BRPI0418328A (pt) 2007-05-02
JP4758909B2 (ja) 2011-08-31
CA2551867A1 (en) 2005-07-21
NZ548098A (en) 2010-05-28

Similar Documents

Publication Publication Date Title
CA2551867C (en) Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives
EP0465121B1 (en) Stable salts of 4"-deoxy-4"-epimethylamino avermectin B1a/B1b
JPH11509550A (ja) 駆虫薬マルクホルチンおよびパラヘルクアミド
WO2014039489A1 (en) Spirocyclic derivatives as antiparasitic agents
JPS63119486A (ja) Ｌｌ−ｆ２８２４９化合物の２３−オキソ（ケト）および２３−イミノ誘導体
AU582214B2 (en) Anthelmintic pyridinyl acylhydrazones, method of use and compositions
EP0557732A1 (en) Methods and compositions for protecting animals against attack and infestation by helminth, acarid and anthropod endo- and ectoparasites
JP4624510B2 (ja) ２−（置換チオ）チアゾロ−［４，５−ｂ］ピリジン化合物の有害生物防除および寄生虫防除的使用
HK1091207B (en) Control of parasites in animals by the use of imidazo [1,2-b]pyridazine derivatives
WO1987006127A1 (en) Anthelmintic acylhydrazones, method of use and compositions
JP2703551B2 (ja) Ｌｌ−ｆ２８２４９化合物のモノ−及びジエポキシド誘導体
CA1340104C (en) 23-deoxy derivatives of ll-f28249 compounds
MXPA06007628A (en) Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives
CN118339164A (zh) 驱虫吡咯并哒嗪化合物
SI9011710A (sl) 13-alkil-23-imino in 13-halo-23-imino derivati makrolidnih spojin
JPS63270685A (ja) Ｌｌ−ｆ２８２４９化合物の２７−ハロゲン化誘導体
TW410227B (en) 14-substituted marcfortines and derivatives useful as antiparasitic agents
CA2077131A1 (en) 13beta-o-methoxymethyl-22,23-dihydro avermectin b1a-b1b aglycone as a superior antiparasitic agent
IL85450A (en) 23-Deoxy-27-halo 26-methylene-ll-f28249 derivatives and parasiticidal use
WO1986005982A3 (en) Anthelmintic quinolinyl acylhydrazones, method of use and compositions
US6482962B2 (en) Pesticidal and parasiticidal use of 1-aryl-1-(substituted thio, sulfinyl and sulfonyl)-2-nitroethane compounds
HK40085992A (en) Novel 6-substituted 7-deazapurines and corresponding nucleosides as medicaments
US20160090373A1 (en) Solid forms of anti-viral compounds
EP0370065A1 (en) Anthelmintic acylhydrazones, method of use and compositions
EP0263209A2 (en) Anthelmintic quinolinyl acylhydrazones

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20131224