BRPI0619154A2 - inibidores do transportador da serotonina (sert) - Google Patents
inibidores do transportador da serotonina (sert) Download PDFInfo
- Publication number
- BRPI0619154A2 BRPI0619154A2 BRPI0619154-1A BRPI0619154A BRPI0619154A2 BR PI0619154 A2 BRPI0619154 A2 BR PI0619154A2 BR PI0619154 A BRPI0619154 A BR PI0619154A BR PI0619154 A2 BRPI0619154 A2 BR PI0619154A2
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- pyrrolidine
- phenyl
- benzyloxymethyl
- trifluoromethyl
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims abstract description 12
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 title abstract description 15
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 230000036506 anxiety Effects 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- -1 3,5-bis-trifluoromethyl-benzyloxymethyl Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- ZYPKYSZNASIHIU-UHFFFAOYSA-N 3-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1C1C(COCC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CNC1 ZYPKYSZNASIHIU-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
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- DBBOSJMPXXOJAX-UHFFFAOYSA-N 3-[(3,5-dimethylphenyl)methoxymethyl]-4-phenylpyrrolidine Chemical compound CC1=CC(C)=CC(COCC2C(CNC2)C=2C=CC=CC=2)=C1 DBBOSJMPXXOJAX-UHFFFAOYSA-N 0.000 claims description 2
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- JSXVUFAASATSJR-UHFFFAOYSA-N 3-phenyl-4-[[3-(trifluoromethoxy)phenyl]methoxymethyl]pyrrolidine Chemical compound FC(F)(F)OC1=CC=CC(COCC2C(CNC2)C=2C=CC=CC=2)=C1 JSXVUFAASATSJR-UHFFFAOYSA-N 0.000 claims description 2
- BRNLNFLKXNVZNF-UHFFFAOYSA-N 3-phenyl-4-[[3-(trifluoromethyl)phenyl]methoxymethyl]pyrrolidine Chemical compound FC(F)(F)C1=CC=CC(COCC2C(CNC2)C=2C=CC=CC=2)=C1 BRNLNFLKXNVZNF-UHFFFAOYSA-N 0.000 claims description 2
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- RQKVSUQPZSYIGU-GNQKOLAMSA-N n-[[3,5-bis(trifluoromethyl)phenyl]methyl]-n-methyl-1-[(3r,4r)-4-phenylpyrrolidin-3-yl]methanamine;dihydrochloride Chemical compound Cl.Cl.C1([C@@H]2CNC[C@@H]2CN(C)CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=CC=CC=C1 RQKVSUQPZSYIGU-GNQKOLAMSA-N 0.000 claims description 2
- UAYHYZNWYLZOLO-UHFFFAOYSA-N 1-phenyl-3-[[4-(trifluoromethyl)phenyl]methoxymethyl]pyrrolidine Chemical compound C1=CC(C(F)(F)F)=CC=C1COCC1CN(C=2C=CC=CC=2)CC1 UAYHYZNWYLZOLO-UHFFFAOYSA-N 0.000 claims 1
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- OFVPXMATUWVZNH-UHFFFAOYSA-N 3-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-(2-chlorophenyl)pyrrolidine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(COCC2C(CNC2)C=2C(=CC=CC=2)Cl)=C1 OFVPXMATUWVZNH-UHFFFAOYSA-N 0.000 claims 1
- ZTAHMLRECRDNFQ-UHFFFAOYSA-N 3-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-(2-methylphenyl)pyrrolidine Chemical compound CC1=CC=CC=C1C1C(COCC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CNC1 ZTAHMLRECRDNFQ-UHFFFAOYSA-N 0.000 claims 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 108060008037 tachykinin Proteins 0.000 description 1
- 239000002462 tachykinin receptor antagonist Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WTYHFVAWQWTGAC-CABCVRRESA-N tert-butyl (3r,4r)-3-(methylsulfonyloxymethyl)-4-phenylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)C[C@H](COS(C)(=O)=O)[C@@H]1C1=CC=CC=C1 WTYHFVAWQWTGAC-CABCVRRESA-N 0.000 description 1
- SAMWVEVQYLBPDS-UHFFFAOYSA-N tert-butyl 3-(2-chlorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=CC=C1Cl SAMWVEVQYLBPDS-UHFFFAOYSA-N 0.000 description 1
- NGISKLSDDDXXRB-UHFFFAOYSA-N tert-butyl 3-(2-fluorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=CC=C1F NGISKLSDDDXXRB-UHFFFAOYSA-N 0.000 description 1
- YJSLRYAFFXPICK-UHFFFAOYSA-N tert-butyl 3-(3-chlorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=CC(Cl)=C1 YJSLRYAFFXPICK-UHFFFAOYSA-N 0.000 description 1
- PFQATTVCUBACQW-UHFFFAOYSA-N tert-butyl 3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=CC(F)=C1 PFQATTVCUBACQW-UHFFFAOYSA-N 0.000 description 1
- VNZXUJLWKOKVCE-UHFFFAOYSA-N tert-butyl 3-(4-chlorophenyl)-4-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=C(Cl)C=C1 VNZXUJLWKOKVCE-UHFFFAOYSA-N 0.000 description 1
- AKAMJEAPQNBMPI-UHFFFAOYSA-N tert-butyl 3-(hydroxymethyl)-4-phenylpyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(CO)C1C1=CC=CC=C1 AKAMJEAPQNBMPI-UHFFFAOYSA-N 0.000 description 1
- HWNMWQQVLWLDBC-UHFFFAOYSA-N tert-butyl 3-[[3,5-bis(trifluoromethyl)phenyl]methoxymethyl]-4-(4-fluorophenyl)pyrrolidine-1-carboxylate Chemical compound C=1C=C(F)C=CC=1C1CN(C(=O)OC(C)(C)C)CC1COCC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HWNMWQQVLWLDBC-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon 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
- A61K31/40—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05111565.7 | 2005-12-01 | ||
| EP05111565 | 2005-12-01 | ||
| PCT/EP2006/068740 WO2007063009A1 (en) | 2005-12-01 | 2006-11-22 | Serotonin transporter (sert) inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0619154A2 true BRPI0619154A2 (pt) | 2011-09-20 |
Family
ID=37686112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0619154-1A BRPI0619154A2 (pt) | 2005-12-01 | 2006-11-22 | inibidores do transportador da serotonina (sert) |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20070129419A1 (https=) |
| EP (1) | EP1957450B1 (https=) |
| JP (1) | JP5020967B2 (https=) |
| KR (1) | KR101091376B1 (https=) |
| CN (1) | CN101316816B (https=) |
| AT (1) | ATE434605T1 (https=) |
| AU (1) | AU2006319244B2 (https=) |
| BR (1) | BRPI0619154A2 (https=) |
| CA (1) | CA2631221C (https=) |
| DE (1) | DE602006007483D1 (https=) |
| ES (1) | ES2326285T3 (https=) |
| IL (1) | IL191468A (https=) |
| WO (1) | WO2007063009A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8471040B2 (en) * | 2010-10-11 | 2013-06-25 | Theravance, Inc. | Serotonin reuptake inhibitors |
| US20160009694A1 (en) * | 2013-03-15 | 2016-01-14 | Portola Pharmaceuticals, Inc. | Cyclohexanediamine compounds and methods for their preparation |
| CA2949160C (en) | 2014-05-15 | 2023-03-21 | Array Biopharma Inc. | 1-((3s,4r)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(4-methyl-3-(2-methylpyrimidin-5-yl)-1-phenyl-1h-pyrazol-5-yl)urea as a trka kinase inhibitor |
| PT3344248T (pt) | 2015-09-02 | 2022-06-29 | Trevena Inc | Compostos moduladores do recetor opioide delta contendo aza-heterocíclicos de 6 membros, composições compreendendo os mesmos e seus usos |
| US11225487B2 (en) | 2017-02-17 | 2022-01-18 | Trevena, Inc. | 7-membered aza-heterocyclic containing δ-opioid receptor modulating compounds, methods of using and making the same |
| BR112019016827A2 (pt) | 2017-02-17 | 2020-04-07 | Trevena Inc | compostos moduladores de receptor delta-opioide contendo aza-heterocíclico com 5 membros, métodos de uso e produção dos mesmos |
| BR112022016941A2 (pt) * | 2020-02-25 | 2022-10-25 | Tes Pharma S R L | Compostos heterocíclicos para a modulação de nr2f6 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI94339C (fi) * | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| GB0119797D0 (en) * | 2001-08-14 | 2001-10-03 | Glaxo Group Ltd | Chemical compounds |
| ATE374183T1 (de) * | 2001-11-13 | 2007-10-15 | Schering Corp | Nk1-antagonisten |
| US7468437B2 (en) * | 2003-09-30 | 2008-12-23 | Merck & Co., Inc. | Phenyl pyrrolidine ether tachykinin receptor antagonists |
| US7138423B2 (en) * | 2004-07-20 | 2006-11-21 | Bristol-Myers Squibb Company | Arylpyrrolidine derivatives as NK-1 /SSRI antagonists |
-
2006
- 2006-11-22 EP EP06819656A patent/EP1957450B1/en not_active Not-in-force
- 2006-11-22 BR BRPI0619154-1A patent/BRPI0619154A2/pt not_active IP Right Cessation
- 2006-11-22 ES ES06819656T patent/ES2326285T3/es active Active
- 2006-11-22 WO PCT/EP2006/068740 patent/WO2007063009A1/en not_active Ceased
- 2006-11-22 US US11/603,515 patent/US20070129419A1/en not_active Abandoned
- 2006-11-22 CA CA2631221A patent/CA2631221C/en not_active Expired - Fee Related
- 2006-11-22 CN CN2006800444805A patent/CN101316816B/zh not_active Expired - Fee Related
- 2006-11-22 KR KR1020087013216A patent/KR101091376B1/ko not_active Expired - Fee Related
- 2006-11-22 AU AU2006319244A patent/AU2006319244B2/en not_active Ceased
- 2006-11-22 AT AT06819656T patent/ATE434605T1/de active
- 2006-11-22 DE DE602006007483T patent/DE602006007483D1/de active Active
- 2006-11-22 JP JP2008542719A patent/JP5020967B2/ja not_active Expired - Fee Related
-
2008
- 2008-05-15 IL IL191468A patent/IL191468A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN101316816A (zh) | 2008-12-03 |
| JP2009517435A (ja) | 2009-04-30 |
| WO2007063009A1 (en) | 2007-06-07 |
| JP5020967B2 (ja) | 2012-09-05 |
| EP1957450A1 (en) | 2008-08-20 |
| CA2631221C (en) | 2014-06-03 |
| KR101091376B1 (ko) | 2011-12-07 |
| CN101316816B (zh) | 2011-07-27 |
| AU2006319244B2 (en) | 2011-07-07 |
| ATE434605T1 (de) | 2009-07-15 |
| EP1957450B1 (en) | 2009-06-24 |
| IL191468A (en) | 2012-02-29 |
| DE602006007483D1 (https=) | 2009-08-06 |
| US20070129419A1 (en) | 2007-06-07 |
| AU2006319244A1 (en) | 2007-06-07 |
| CA2631221A1 (en) | 2007-06-07 |
| ES2326285T3 (es) | 2009-10-06 |
| KR20080064200A (ko) | 2008-07-08 |
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