ES2627221T3 - Compuestos de heterocicloalquiloxibenzamida N-sustituidos y métodos de uso - Google Patents
Compuestos de heterocicloalquiloxibenzamida N-sustituidos y métodos de uso Download PDFInfo
- Publication number
- ES2627221T3 ES2627221T3 ES07855342.7T ES07855342T ES2627221T3 ES 2627221 T3 ES2627221 T3 ES 2627221T3 ES 07855342 T ES07855342 T ES 07855342T ES 2627221 T3 ES2627221 T3 ES 2627221T3
- Authority
- ES
- Spain
- Prior art keywords
- piperidin
- yloxy
- benzamide
- benzylpiperidin
- alkyl
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
- 238000000034 method Methods 0.000 title claims description 28
- -1 -NO Chemical group 0.000 claims abstract description 264
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 41
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000005843 halogen group Chemical group 0.000 claims abstract description 33
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 14
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 13
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 13
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract description 9
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 9
- OPZIJNBWFXUVDG-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-3-chloro-4-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]oxybenzamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)Cl)CC1 OPZIJNBWFXUVDG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 238000006467 substitution reaction Methods 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
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- 101000783681 Homo sapiens 5'-AMP-activated protein kinase catalytic subunit alpha-2 Proteins 0.000 claims description 28
- 230000037361 pathway Effects 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
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- 230000003213 activating effect Effects 0.000 claims description 6
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- 239000003937 drug carrier Substances 0.000 claims description 5
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 229910006067 SO3−M Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 229940095102 methyl benzoate Drugs 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- PYPFAWVKBZFLFU-UHFFFAOYSA-N 4-[[4-[[3-fluoro-4-[1-[4-(trifluoromethyl)phenyl]piperidin-4-yl]oxybenzoyl]amino]piperidin-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(NC(=O)C=2C=C(F)C(OC3CCN(CC3)C=3C=CC(=CC=3)C(F)(F)F)=CC=2)CC1 PYPFAWVKBZFLFU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- AGGMXPHWCFTUOU-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-3-chloro-4-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-yl]oxybenzamide Chemical compound C=1C=C(OC2CCN(CC=3C=C4OCCOC4=CC=3)CC2)C(Cl)=CC=1C(=O)NC(CC1)CCN1CC1=CC=CC=C1 AGGMXPHWCFTUOU-UHFFFAOYSA-N 0.000 claims description 2
- OSEGNJLBTIAZAR-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-(1-benzylpiperidin-4-yl)oxy-3-chlorobenzamide Chemical compound ClC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=CC=C1 OSEGNJLBTIAZAR-UHFFFAOYSA-N 0.000 claims description 2
- SJIZCVQALKMPCJ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-(1-benzylpiperidin-4-yl)oxy-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=CC=C1 SJIZCVQALKMPCJ-UHFFFAOYSA-N 0.000 claims description 2
- FEMJUIILXCLATR-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(C#N)C=C1 FEMJUIILXCLATR-UHFFFAOYSA-N 0.000 claims description 2
- OESUCOSKWSDWGA-UHFFFAOYSA-N n-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]-4-[1-(4-cyanophenyl)piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(=CC=3)C#N)CC2)=CC=C1OC(CC1)CCN1C1=CC=C(C#N)C=C1 OESUCOSKWSDWGA-UHFFFAOYSA-N 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- ZSSQHQZDGFFADT-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 ZSSQHQZDGFFADT-UHFFFAOYSA-N 0.000 claims 1
- VTAPBBBNOFCMJE-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)F)CC1 VTAPBBBNOFCMJE-UHFFFAOYSA-N 0.000 claims 1
- WPVQGPSAFVQBTQ-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C=C1 WPVQGPSAFVQBTQ-UHFFFAOYSA-N 0.000 claims 1
- RSVKHYKCXSKQMH-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-(4-cyanophenyl)piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1C1=CC=C(C#N)C=C1 RSVKHYKCXSKQMH-UHFFFAOYSA-N 0.000 claims 1
- FTQQFCXRUSWUMF-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C(Cl)=C1 FTQQFCXRUSWUMF-UHFFFAOYSA-N 0.000 claims 1
- UIOUEJIAZRRPMS-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound C1=C(F)C(F)=CC=C1CN1CCC(OC=2C(=CC(=CC=2)C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)F)CC1 UIOUEJIAZRRPMS-UHFFFAOYSA-N 0.000 claims 1
- QFKXALBARODOIK-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(Cl)C=C1 QFKXALBARODOIK-UHFFFAOYSA-N 0.000 claims 1
- WHGMTCQFUXQDID-UHFFFAOYSA-N n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-4-[1-[(4-cyanophenyl)methyl]piperidin-4-yl]oxy-3-fluorobenzamide Chemical compound FC1=CC(C(=O)NC2CCN(CC=3C=CC(Cl)=CC=3)CC2)=CC=C1OC(CC1)CCN1CC1=CC=C(C#N)C=C1 WHGMTCQFUXQDID-UHFFFAOYSA-N 0.000 claims 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 1
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- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P3/06—Antihyperlipidemics
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- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
-
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
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| US88231206P | 2006-12-28 | 2006-12-28 | |
| US882312P | 2006-12-28 | ||
| US98871907P | 2007-11-16 | 2007-11-16 | |
| US988719P | 2007-11-16 | ||
| PCT/US2007/088742 WO2008083124A1 (en) | 2006-12-28 | 2007-12-21 | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
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| Publication Number | Publication Date |
|---|---|
| ES2627221T3 true ES2627221T3 (es) | 2017-07-27 |
Family
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| Country | Link |
|---|---|
| US (3) | US8012955B2 (enExample) |
| EP (1) | EP2079694B1 (enExample) |
| JP (1) | JP5650404B2 (enExample) |
| CA (1) | CA2674237C (enExample) |
| ES (1) | ES2627221T3 (enExample) |
| WO (1) | WO2008083124A1 (enExample) |
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| BRPI0911681B8 (pt) * | 2008-04-23 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, composição farmacêutica, e, método para ativar a via de proteína quinase ativada por 5'-amp em uma célula in vitro |
| MX2011007639A (es) | 2009-01-28 | 2011-09-15 | Rigel Pharmaceuticals Inc | Compuestos de carboxamida y metodos para usar los mismos. |
| GB0912975D0 (en) * | 2009-07-24 | 2009-09-02 | Syngenta Ltd | Formulations |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2011123681A1 (en) | 2010-03-31 | 2011-10-06 | Rigel Pharmaceuticals, Inc. | Methods for using carboxamide, sulfonamide and amine compounds |
| JPWO2011142359A1 (ja) * | 2010-05-10 | 2013-07-22 | 日産化学工業株式会社 | スピロ化合物及びアディポネクチン受容体活性化薬 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
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| NZ585298A (en) | 2007-11-16 | 2012-08-31 | Rigel Pharmaceuticals Inc | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| EP2231666B1 (en) | 2007-12-12 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide, sulfonamide and amine compounds for metabolic disorders |
| BRPI0911681B8 (pt) | 2008-04-23 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, composição farmacêutica, e, método para ativar a via de proteína quinase ativada por 5'-amp em uma célula in vitro |
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2007
- 2007-12-21 US US11/963,742 patent/US8012955B2/en active Active
- 2007-12-21 WO PCT/US2007/088742 patent/WO2008083124A1/en not_active Ceased
- 2007-12-21 ES ES07855342.7T patent/ES2627221T3/es active Active
- 2007-12-21 CA CA2674237A patent/CA2674237C/en active Active
- 2007-12-21 JP JP2009544239A patent/JP5650404B2/ja not_active Expired - Fee Related
- 2007-12-21 EP EP07855342.7A patent/EP2079694B1/en not_active Not-in-force
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2011
- 2011-07-18 US US13/185,030 patent/US8697727B2/en active Active
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2014
- 2014-02-25 US US14/189,638 patent/US9181220B2/en active Active
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| Publication number | Publication date |
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| US20140179738A1 (en) | 2014-06-26 |
| CA2674237C (en) | 2015-11-24 |
| US9181220B2 (en) | 2015-11-10 |
| EP2079694B1 (en) | 2017-03-01 |
| WO2008083124A1 (en) | 2008-07-10 |
| JP2010514788A (ja) | 2010-05-06 |
| US8697727B2 (en) | 2014-04-15 |
| CA2674237A1 (en) | 2008-07-10 |
| EP2079694A1 (en) | 2009-07-22 |
| JP5650404B2 (ja) | 2015-01-07 |
| US8012955B2 (en) | 2011-09-06 |
| US20110306767A1 (en) | 2011-12-15 |
| US20090186894A1 (en) | 2009-07-23 |
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