CA2691961C - Catecholamine derivatives and prodrugs thereof - Google Patents

Catecholamine derivatives and prodrugs thereof Download PDF

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Publication number
CA2691961C
CA2691961C CA2691961A CA2691961A CA2691961C CA 2691961 C CA2691961 C CA 2691961C CA 2691961 A CA2691961 A CA 2691961A CA 2691961 A CA2691961 A CA 2691961A CA 2691961 C CA2691961 C CA 2691961C
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CA
Canada
Prior art keywords
mammal
treatment
compound according
pharmaceutically acceptable
acid addition
Prior art date
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Application number
CA2691961A
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English (en)
French (fr)
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CA2691961A1 (en
Inventor
Morten Joergensen
Benny Bang-Andersen
Ask Pueschl
Niels Moerk
Jennifer Larsen
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.)
H Lundbeck AS
Original Assignee
H Lundbeck AS
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Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39877715&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2691961(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by H Lundbeck AS filed Critical H Lundbeck AS
Publication of CA2691961A1 publication Critical patent/CA2691961A1/en
Application granted granted Critical
Publication of CA2691961C publication Critical patent/CA2691961C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • 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
    • C07D491/04—Ortho-condensed systems
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4741—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having oxygen as a ring hetero atom, e.g. tubocuraran derivatives, noscapine, bicuculline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
    • 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
    • A61P25/14—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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/08—Aza-anthracenes
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychiatry (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Epidemiology (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Vascular Medicine (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Portable Nailing Machines And Staplers (AREA)
CA2691961A 2007-08-31 2008-08-28 Catecholamine derivatives and prodrugs thereof Active CA2691961C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DKPA200701250 2007-08-31
DKPA200701250 2007-08-31
PCT/DK2008/050214 WO2009026934A1 (en) 2007-08-31 2008-08-28 Catecholamine derivatives useful for the treatment of parkinson' s disease

Publications (2)

Publication Number Publication Date
CA2691961A1 CA2691961A1 (en) 2009-03-05
CA2691961C true CA2691961C (en) 2013-12-17

Family

ID=39877715

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2691961A Active CA2691961C (en) 2007-08-31 2008-08-28 Catecholamine derivatives and prodrugs thereof
CA2697688A Abandoned CA2697688A1 (en) 2007-08-31 2008-08-28 Catecholamine derivatives and prodrugs thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2697688A Abandoned CA2697688A1 (en) 2007-08-31 2008-08-28 Catecholamine derivatives and prodrugs thereof

Country Status (29)

Country Link
EP (4) EP2662358A1 (enExample)
JP (4) JP5548125B2 (enExample)
KR (3) KR20150115963A (enExample)
CN (3) CN107253956A (enExample)
AR (2) AR068044A1 (enExample)
AU (2) AU2008291426B2 (enExample)
BR (2) BRPI0813456A2 (enExample)
CA (2) CA2691961C (enExample)
CL (2) CL2008002558A1 (enExample)
CO (2) CO6270232A2 (enExample)
CY (1) CY1117326T1 (enExample)
DK (1) DK2197883T3 (enExample)
EA (2) EA018413B1 (enExample)
ES (1) ES2557485T3 (enExample)
HR (1) HRP20151334T1 (enExample)
HU (1) HUE025882T2 (enExample)
IL (1) IL203080A (enExample)
MX (1) MX2010002210A (enExample)
MY (2) MY148948A (enExample)
NZ (2) NZ583551A (enExample)
PL (1) PL2197883T3 (enExample)
PT (1) PT2197883E (enExample)
RS (1) RS54470B1 (enExample)
SG (1) SG184711A1 (enExample)
SI (1) SI2197883T1 (enExample)
TW (2) TWI404702B (enExample)
UA (2) UA97989C2 (enExample)
WO (2) WO2009026934A1 (enExample)
ZA (2) ZA200909191B (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI404702B (zh) * 2007-08-31 2013-08-11 Lundbeck & Co As H 兒茶酚胺衍生物和其前藥
US8067410B2 (en) 2008-06-27 2011-11-29 H. Lundbeck A/S Phenolic and catecholic amines and prodrugs thereof
JP2011525893A (ja) * 2008-06-27 2011-09-29 ハー・ルンドベック・アクチエゼルスカベット 新規のフェノールアミン類およびカテコールアミン類ならびにそのプロドラッグ
TW201035054A (en) * 2009-02-27 2010-10-01 Lundbeck & Co As H Methods of administering (4aR, 10aR)-1-n-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline-6,7-diol and pharmaceutical compositions thereof
TW201036949A (en) * 2009-02-27 2010-10-16 Lundbeck & Co As H Treatment of dyskinesia related disorders
CR20200225A (es) * 2017-11-24 2020-07-25 H Lundbeck As Nuevos fármacos de catecolamina para uso en el tratamiento de la enfermedad de parkinson
WO2020070099A1 (en) 2018-10-02 2020-04-09 H. Lundbeck A/S Administration of catecholamine prodrugs in combination with a 5-ht2b antagonist
US11111263B2 (en) * 2019-05-20 2021-09-07 H. Lundbeck A/S Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
US11130775B2 (en) * 2019-05-20 2021-09-28 H. Lundbeck A/S Solid forms of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4aR,10aR)-7-hydroxy-1-propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
US11104697B2 (en) 2019-05-20 2021-08-31 H. Lundbeck A/S Process for the manufacture of (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((4AR,10AR)-7-hydroxy-1- propyl-1,2,3,4,4A,5,10,10A-octahydrobenzo[g]quinolin-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid
US11168056B2 (en) 2019-05-20 2021-11-09 H. Lundbeck A/S Process for the manufacturing of (6aR,10aR)-7-propyl-6,6a,7,8,9,10,10a,11-octahydro-[1,3]dioxolo[4′,5′:5,6]benzo[1,2-G]quinoline and (4aR,10aR)-1-propyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[G]quinoline-6,7-diol
EP3972600B1 (en) 2019-05-21 2026-02-18 H. Lundbeck A/S Catecholamine carbamate prodrugs for use in the treatment of parkinson s disease
JP7562562B2 (ja) * 2019-05-21 2024-10-07 ハー・ルンドベック・アクチエゼルスカベット パーキンソン病の治療に使用するための新規なカテコールアミンプロドラッグ
EP3972971A1 (en) * 2019-05-21 2022-03-30 H. Lundbeck A/S New catecholamine prodrugs for use in the treatment of parkinson's diseases
JP7641234B2 (ja) 2019-05-21 2025-03-06 ハー・ルンドベック・アクチエゼルスカベット パーキンソン病の治療に使用するための新規なカテコールアミンプロドラッグ
CN114478298B (zh) * 2020-11-12 2024-09-27 成都西岭源药业有限公司 一种造影剂碘佛醇的纯化方法
US20240025857A1 (en) * 2020-11-17 2024-01-25 H. Lundbeck A/S New catecholamine prodrugs for use in the treatment of parkinson's disease
CN113620760A (zh) * 2021-09-07 2021-11-09 张家口思睿凯科技有限公司 一种电子盐反应液和不饱和芳香烃类化合物的还原方法
WO2025078574A1 (en) * 2023-10-12 2025-04-17 Integrative Research Laboratories Sweden Ab NOVEL ESTERS OF 1,2,3,4,4a,5,6,7,8,9,10,10a-DODECAHYDROBENZO[g]QUINOLIN-6-OL COMPOUNDS AND USES THEREOF

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080456A (en) * 1971-10-26 1978-03-21 Schering Aktiengesellschaft Diacylapomorphines
CH648300A5 (en) * 1979-06-22 1985-03-15 Sandoz Ag Phenanthrene derivatives and medicaments containing them
US4543256A (en) * 1982-03-17 1985-09-24 Northeastern University (-)-10,1L Methylenedioxy-N-N-propylnoraporphine and methods employing it for inhibiting the effects of epileptic seizures and for prevention and treatment of duodenal ulcers
WO1990012574A1 (en) * 1989-04-25 1990-11-01 Northeastern University Dopamine agonist compounds
IE903127A1 (en) * 1989-08-30 1991-03-13 Sankyo Co Indolobenzoquinoline derivatives, their preparation and¹their use as anti-arrhythmic drugs
TW357143B (en) * 1995-07-07 1999-05-01 Novartis Ag Benzo[g]quinoline derivatives
JPH11515030A (ja) * 1995-11-10 1999-12-21 ノボ ノルディスク アクティーゼルスカブ シス−ベンズ［ｅ］インドール化合物のエナンチオマー、これらの製造、及びドーパミン−Ｄ３受容体選択的医薬としての利用
CN1241998A (zh) * 1996-10-30 2000-01-19 伊莱利利公司 苯并[f]喹啉酮的合成
SE0102036D0 (sv) 2001-06-08 2001-06-08 Axon Biochemicals Bv Pharmaceutical formulation for the efficient administration of apomorphine, 6aR- (-) -N- Propyl- norapomorphine and their derivatives and pro-drugs thereof
SE0002934D0 (sv) 2000-08-17 2000-08-17 Axon Biochemicals Bv New aporphine esters and in their use in therapy
AR030357A1 (es) * 2000-08-18 2003-08-20 Lundbeck & Co As H Derivados 4 -, 5 -, 6 - y 7-indol
US20050090518A1 (en) * 2003-10-24 2005-04-28 Nastech Pharmaceutical Company Inc. Method for treating parkinson's disease using apomorphine and apomorphine prodrugs
TWI404702B (zh) * 2007-08-31 2013-08-11 Lundbeck & Co As H 兒茶酚胺衍生物和其前藥

Also Published As

Publication number Publication date
CA2691961A1 (en) 2009-03-05
ZA201001422B (en) 2011-06-29
CN101687878A (zh) 2010-03-31
JP2010536889A (ja) 2010-12-02
AU2008291425A1 (en) 2009-03-05
NZ582379A (en) 2011-08-26
AR068045A1 (es) 2009-10-28
MY148948A (en) 2013-06-14
KR20150115963A (ko) 2015-10-14
WO2009026935A1 (en) 2009-03-05
DK2197883T3 (en) 2016-01-11
CY1117326T1 (el) 2017-04-26
EP2197883A1 (en) 2010-06-23
EP2662358A1 (en) 2013-11-13
EA201070327A1 (ru) 2010-08-30
UA98804C2 (ru) 2012-06-25
AU2008291425B2 (en) 2012-12-06
WO2009026934A1 (en) 2009-03-05
CL2008002564A1 (es) 2009-07-17
ES2557485T3 (es) 2016-01-26
ZA200909191B (en) 2011-03-30
KR101597367B1 (ko) 2016-02-24
HRP20151334T1 (hr) 2016-01-01
MX2010002210A (es) 2010-03-17
SI2197883T1 (sl) 2016-01-29
TWI404702B (zh) 2013-08-11
NZ583551A (en) 2012-07-27
TW200911752A (en) 2009-03-16
JP2014148528A (ja) 2014-08-21
CN101842354A (zh) 2010-09-22
BRPI0813456A2 (pt) 2014-12-23
KR20100046111A (ko) 2010-05-06
MY179527A (en) 2020-11-10
BRPI0815894A2 (pt) 2015-02-24
JP2010536890A (ja) 2010-12-02
CA2697688A1 (en) 2009-03-05
JP5548125B2 (ja) 2014-07-16
HUE025882T2 (en) 2016-04-28
IL203080A (en) 2014-11-30
PL2197883T3 (pl) 2016-03-31
CL2008002558A1 (es) 2009-08-07
JP2014111635A (ja) 2014-06-19
KR20100051834A (ko) 2010-05-18
PT2197883E (pt) 2016-02-02
JP5802792B2 (ja) 2015-11-04
EP2197883B1 (en) 2015-11-18
SG184711A1 (en) 2012-10-30
CO6260082A2 (es) 2011-03-22
AU2008291426B2 (en) 2013-01-31
TW200914426A (en) 2009-04-01
UA97989C2 (uk) 2012-04-10
CN107253956A (zh) 2017-10-17
EP3009437A1 (en) 2016-04-20
EP2195291A1 (en) 2010-06-16
EA200971107A1 (ru) 2010-06-30
RS54470B1 (sr) 2016-06-30
AR068044A1 (es) 2009-10-28
AU2008291426A1 (en) 2009-03-05
EA018413B1 (ru) 2013-07-30
EA018011B1 (ru) 2013-04-30
CO6270232A2 (es) 2011-04-20

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