JP5027208B2 - セロトニントランスポータ阻害剤およびニューロキニン−1受容体アンタゴニストとして有用なピペリジン誘導体 - Google Patents
セロトニントランスポータ阻害剤およびニューロキニン−1受容体アンタゴニストとして有用なピペリジン誘導体 Download PDFInfo
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- JP5027208B2 JP5027208B2 JP2009503526A JP2009503526A JP5027208B2 JP 5027208 B2 JP5027208 B2 JP 5027208B2 JP 2009503526 A JP2009503526 A JP 2009503526A JP 2009503526 A JP2009503526 A JP 2009503526A JP 5027208 B2 JP5027208 B2 JP 5027208B2
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- benzyloxymethyl
- piperidine
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- 0 *c1cc(CO)cc(C(F)(F)F)c1 Chemical compound *c1cc(CO)cc(C(F)(F)F)c1 0.000 description 1
- LQMZSVRCDYSUIJ-UHFFFAOYSA-N CC(C)(C)OC(N(CC1)CC(C(OC)=O)=C1OS(C(F)(F)F)(=O)=O)=O Chemical compound CC(C)(C)OC(N(CC1)CC(C(OC)=O)=C1OS(C(F)(F)F)(=O)=O)=O LQMZSVRCDYSUIJ-UHFFFAOYSA-N 0.000 description 1
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
- A61K31/435—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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4465—Non condensed piperidines, e.g. piperocaine only substituted in position 4
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
R1は、水素、ハロゲンまたは低級アルキルであり;
R2は、水素、低級アルキルまたは−(CH2)nCNであり;
R3は、水素またはCF3であり;
nは、1または2であり;
点線は、結合であってもなくてもよい)
で示されるトランス誘導体、およびその薬学的に許容され得る酸付加塩に関する。
組換えヒトSERTを安定発現するHEK−293細胞を、10%FBS、300μg/ml G418および2mM L−グルタミンを含む高グルコースDMEMで保持し、5%CO2と共に37℃でインキュベートした。PBSを用いて、細胞を1〜2分間、培養フラスコから遊離させた。次に、細胞を1000gで5分間遠心分離し、PBSで再懸濁させた後、膜の調製に用いた。
Semlikiウイルス発現系を用いてヒトNK−1受容体をトランスフェクトし、[3H]サブスタンスP(最終濃度0.6nM)で放射線標識したCHO細胞中のヒトNK−1受容体で、NK−1受容体に対するテスト化合物の親和力を評価した。BSA(0.04%)、ロイペプチン(8μg/ml)、MnCl2(3mM)およびホスホラミドン(2μM)を含むHEPES緩衝液(50mM、pH7.4)中で、結合アッセイを実施した。結合アッセイは、膜懸濁液250μl(1.25×105細胞/アッセイ試験管)、置換剤の緩衝液125μlおよび[3H]サブスタンスP 125μlで構成されていた。少なくとも10の化合物濃度で、置換曲線を決定した。アッセイ試験管を室温で60分間インキュベートし、その後、真空下で、PEI(0.3%)を60分間予浸したGF/Cフィルターで試験管の内容物を迅速にろ過し、HEPES緩衝液(50mM、pH7.4)2mlで2回洗浄した。フィルターに残留した放射能を、シンチレーションカウントにより測定した。アッセイは全て、少なくとも2度の別個の実験で2重測定として実施した。
− Froger, N., Gardier, A. M., Moratalla, R., et al., 5-HT1A autoreceptor adaptive changes in substance P (Neurokinin 1)receptor knock-out mice mimic antidepressant-induced desensitization. J. Neuroscience, 21(20), 8188-8197 (2001).
− Kramer M. S., Cutler, N., Feighner, J. et al., Distinct Mechanism of antidepressant activity by blockade of central substance P receptors. Science 281, 1640-1645 (1998).
− Millan, M. J., Lejeune, F., de Nauteuil, G. and Gobert, A. selective blockade of neurokinin NK1 receptors facilitates the activity of adrenergic pathways projecting to the frontal cortex and dorsal hippocampus in rats. J. Neurochem., 76, 1949-1954 (2001).
− Rupniak, N. M. J. New Insights into the antidepressant actions of substance P (NK1 receptor) antagonists. N. M. J Can. J. Physiol. Pharmacol. 80, 489-494 (2002).
− Rupniak, N. M. J. Elucidating the antidepressant actions of substance P (NK1 receptor) antagonists. Current Opinion in Investigational Drugs, 3(2), 257-261 (2002).
− Ryckmans, T., Balancon, L., Berton, O., et al., First dual NK1 antagonists-serotonin reuptake inhibitors: synthesis and SAR of a new class of potential antidepressants. Bioorg. Med. Chem. Lett. 12(2), 261-264 (2002).
− Ryckmans, T., Berton, O., Grimee, R., et a,. Dual NK1 Antagonists-serotonin reuptake inhibitors as potential antidepressants. Part 2: SAR and activity of benzyloxyphenethyl piperazine derivatives. Bioorg. Med. Chem. Lett. 12(21), 3195-3198 (2002).
− WO98/47514 A1. Use of an NK1 receptor antagonist and an SSRI for treating obesity.
− WO03/015784 A1. 2-Substituted 1-arylpiperazines as tachykinin antagonists and/or serotonin reuptake inhibitors.
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン、
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン、
(−)−[(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン−1−イル]−アセトニトリル、
(−)−(3S,4R)−4−(4−フルオロ−フェニル)−3−(3−トリフルオロメチル−ベンジルオキシメチル)−ピペリジン、
(3SR,4RS)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−フェニル−ピペリジン、または
(−)−(トランス)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−ピペリジン、
である。
5−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−1,2,3,6−テトラヒドロ−ピリジン、
である。
a)式II:
b)式I−1:
c)式I−1:
d)式VII:
所望の場合、得られた化合物を薬学的に許容され得る酸付加塩に変換する工程を含む。
4−(4−フルオロ−フェニル)−5,6−ジヒドロ−2H−ピリジン−1,3−ジカルボン酸1−tert−ブチルエステル
a)4−トリフルオロメタンスルホニルオキシ−5,6−ジヒドロ−2H−ピリジン−1,3−ジカルボン酸1−tert−ブチルエステル3−メチルエステル
MSm/e(%):334(M+H+−C4H8,100)
MSm/e(%):336(M+H+,10)
MSm/e(%):320(M−H+,100)
4−フェニル−5,6−ジヒドロ−2H−ピリジン−1,3−ジカルボン酸1−tert−ブチルエステル
MSm/e(%):302(M−H+,100)
4−o−トリル−5,6−ジヒドロ−2H−ピリジン−1,3−ジカルボン酸1−tert−ブチルエステル
a)4−o−トリル−5,6−ジヒドロ−2H−ピリジン−1,3−ジカルボン酸1−tert−ブチルエステル3−メチルエステル
MSm/e(%):332(M+H+,16)
MSm/e(%):316(M−H+,100)
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン塩酸塩
a)(+)−(3R,4R)−4−(4−フルオロ−フェニル)−ピペリジン−1,3−ジカルボン酸1−tert−ブチルエステル
MSm/e(%):322(M−H+,100)
表題化合物の2mg試料を、室温でジエチルエーテル中のジアゾメタンの約0.5M溶液0.5mlで処理して、メチルエステルに変換した。穏やかなアルゴン気流の下で過剰のジアゾメタンおよびジエチルエーテルを蒸発させた後、残渣を酢酸エチル1mlに溶解した。BGB−175カラム、10m*0.1mm*df0.1μm、水素 230kPa、スプリット比 1:300;温度勾配100−200℃、2℃/分のプログラム;インジェクター温度 200℃、検出器温度 210℃。保持時間:46.59分((+)−酸のメチルエステル)、46.76分((−)−酸のメチルエステル)。
MSm/e(%):338(M+H+,28)
[α]D=+68.69(c=0.310,CHCl3)
[α]578=+71.27(c=0.310,CHCl3)
[α]365=+221.60(c=0.310,CHCl3)
MSm/e(%):322(M−H+,100)
[α]D=−0.650(c=0.154,CHCl3)
Chiralpak-OD-Hカラム、25cm*4.6mm、95% n−ヘプタン+0.1%トリフルオロ酢酸を含む5% 2−プロパノール、流速0.7ml/分、30℃、注入容積0.001ml、210nm、保持時間:(−)−酸で9.5分、(+)−酸で11.5分。
以下の通り、旋光、およびChiralpak-OD-HカラムでのHPLC分析での保持時間を、(−)−(3S,4R)−4−(4−フルオロ−フェニル)−1−メチル−ピペリジン−3−カルボン酸メチルエステル(WO0129031に記載されたとおり製造)から誘導された(−)−(3S,4R)−4−(4−フルオロ−フェニル)−ピペリジン−1,3−ジカルボン酸1−tert−ブチルエステルの試料の値と比較することにより、表題化合物の絶対配置を(3S,4R)として帰属した。
MSm/e(%):322(M−H+,100)
[α]D=−0.867(c=0.462,CHCl3)
MSm/e(%):310(M+H+,32)
MSm/e(%):536(M+H+,13)
[α]D=−5.26(c=0.362,CHCl3)
MSm/e(%):436(M+H+,100)
[α]D=−40.8(c=0.385,CHCl3)
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン
MSm/e(%):450(M+H+,100)
[α]D=−37.8(c=0.558,CHCl3)
(−)−[(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン−1−イル]−アセトニトリル
MSm/e(%):475(M+H+,100)
[α]D=−46.16(c=0.496,CHCl3)
(−)−(3S,4R)−4−(4−フルオロ−フェニル)−3−(3−トリフルオロメチル−ベンジルオキシメチル)−ピペリジン塩酸塩
MSm/e(%):368(M+H+,100)
[α]D=−39.93(c=0.431,CHCl3)
(3SR,4RS)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−フェニル−ピペリジン塩酸塩
MSm/e(%):418(M+H+,100)
(−)−(トランス)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−ピペリジン塩酸塩
a)(+)−(シス)−4−o−トリル−ピペリジン−1,3−ジカルボン酸1−tert−ブチルエステル
MSm/e(%):318(M−H+,100)
[α]D=+78.71(c=0.700,CHCl3)
Chiralpak-ADHカラム、25cm*4.6mm、85% n−ヘプタン+1%トリフルオロ酢酸を含む15%エタノール、流速0.7ml/分、20℃、注入容積0.005ml、215nm、保持時間:(−)−酸で8.1分、(+)−酸で8.8分。
MSm/e(%):432(M+H+,100)
[α]D=−33.36(c=0.408,CHCl3)
5−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−1,2,3,6−テトラヒドロ−ピリジン塩酸塩
a)臭化1−ベンジル−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−ピリジニウム
MSm/e(%):516(M+,100)
MSm/e(%):520(M+H+,100)
MSm/e(%):430(M+H+,100)
Claims (10)
- 式I−Aで示される化合物が、
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン、
(−)−(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン、
(−)−[(3S,4R)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−(4−フルオロ−フェニル)−ピペリジン−1−イル]−アセトニトリル、
(−)−(3S,4R)−4−(4−フルオロ−フェニル)−3−(3−トリフルオロメチル−ベンジルオキシメチル)−ピペリジン、
(3SR,4RS)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−フェニル−ピペリジン、または
(−)−(トランス)−3−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−ピペリジン、
である、請求項1記載の使用。 - 5−(3,5−ビス−トリフルオロメチル−ベンジルオキシメチル)−4−o−トリル−1,2,3,6−テトラヒドロ−ピリジンである、請求項3記載の式I−Bで示される化合物。
- 請求項3に記載の式I−Bで示される化合物および薬学的に許容され得る賦形剤を含む医薬。
- 不安およびうつを処置するための、請求項1記載の式I−Aまたは式I−Bで示される化合物1種以上および薬学的に許容され得る賦形剤を含む医薬。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06112170 | 2006-04-03 | ||
EP06112170.3 | 2006-04-03 | ||
PCT/EP2007/052852 WO2007113153A1 (en) | 2006-04-03 | 2007-03-26 | Piperidine derivatives useful as serotonin transporter inhibitors and neurokinin-1 receptor antagonists |
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JP5027208B2 true JP5027208B2 (ja) | 2012-09-19 |
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US (2) | US7872022B2 (ja) |
EP (1) | EP2004605B1 (ja) |
JP (1) | JP5027208B2 (ja) |
KR (1) | KR101101107B1 (ja) |
CN (1) | CN101460460B (ja) |
AT (1) | ATE514677T1 (ja) |
AU (1) | AU2007233812B2 (ja) |
BR (1) | BRPI0709742A2 (ja) |
CA (1) | CA2648065C (ja) |
ES (1) | ES2367219T3 (ja) |
IL (1) | IL194392A (ja) |
MX (1) | MX2008012634A (ja) |
WO (1) | WO2007113153A1 (ja) |
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US7872022B2 (en) * | 2006-04-03 | 2011-01-18 | Hoffmann-La Roche Inc. | Serotonin transporter (SERT) inhibitors for the treatment of depression and anxiety |
TW202246215A (zh) * | 2015-12-18 | 2022-12-01 | 美商亞德利克斯公司 | 作為非全身tgr5促效劑之經取代之4-苯基吡啶化合物 |
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IL98757A (en) | 1990-07-18 | 1997-01-10 | Novo Nordisk As | Piperidine derivatives their preparation and pharmaceutical compositions containing them |
JP2001523245A (ja) | 1997-04-24 | 2001-11-20 | メルク シヤープ エンド ドーム リミテツド | 肥満を治療するためのnk−1受容体拮抗薬およびssriの使用 |
GB9904786D0 (en) * | 1999-03-02 | 1999-04-28 | Merck Sharp & Dohme | Therapeutic agents |
EP1035115B1 (en) | 1999-02-24 | 2004-09-29 | F. Hoffmann-La Roche Ag | 4-Phenylpyridine derivatives and their use as NK-1 receptor antagonists |
GB9924855D0 (en) | 1999-10-20 | 1999-12-22 | Smithkline Beecham Plc | Novel processes |
JP3860445B2 (ja) * | 2001-04-19 | 2006-12-20 | 独立行政法人科学技術振興機構 | Cu−Be基非晶質合金 |
GB0119797D0 (en) | 2001-08-14 | 2001-10-03 | Glaxo Group Ltd | Chemical compounds |
KR100866220B1 (ko) * | 2001-09-06 | 2008-10-30 | 가부시키가이샤 노리타케 캄파니 리미티드 | 도체 조성물 및 그 제조방법 |
GB0203020D0 (en) * | 2002-02-08 | 2002-03-27 | Glaxo Group Ltd | Chemical compounds |
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WO2008001518A1 (fr) * | 2006-06-30 | 2008-01-03 | Mitsubishi Materials Corporation | Composition de fabrication d'une électrode dans une cellule solaire, procédé de fabrication de l'électrode, et cellule solaire utilisant une électrode obtenue par le procédé de fabrication |
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2007
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- 2007-03-26 WO PCT/EP2007/052852 patent/WO2007113153A1/en active Application Filing
- 2007-03-26 BR BRPI0709742-5A patent/BRPI0709742A2/pt not_active Application Discontinuation
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AU2007233812A1 (en) | 2007-10-11 |
BRPI0709742A2 (pt) | 2011-07-26 |
CN101460460B (zh) | 2011-07-27 |
AU2007233812B2 (en) | 2013-03-21 |
IL194392A (en) | 2013-10-31 |
ATE514677T1 (de) | 2011-07-15 |
US20110105561A1 (en) | 2011-05-05 |
EP2004605B1 (en) | 2011-06-29 |
CA2648065C (en) | 2015-06-02 |
CA2648065A1 (en) | 2007-10-11 |
ES2367219T3 (es) | 2011-10-31 |
US8580821B2 (en) | 2013-11-12 |
KR101101107B1 (ko) | 2012-01-03 |
KR20080100383A (ko) | 2008-11-17 |
IL194392A0 (en) | 2009-08-03 |
MX2008012634A (es) | 2008-10-13 |
CN101460460A (zh) | 2009-06-17 |
EP2004605A1 (en) | 2008-12-24 |
US7872022B2 (en) | 2011-01-18 |
US20070232652A1 (en) | 2007-10-04 |
WO2007113153A1 (en) | 2007-10-11 |
JP2009532409A (ja) | 2009-09-10 |
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