UA82867C2 - 2-pyridinecarboxamide derivatives - Google Patents
2-pyridinecarboxamide derivatives Download PDFInfo
- Publication number
- UA82867C2 UA82867C2 UAA200508682A UA2005008682A UA82867C2 UA 82867 C2 UA82867 C2 UA 82867C2 UA A200508682 A UAA200508682 A UA A200508682A UA 2005008682 A UA2005008682 A UA 2005008682A UA 82867 C2 UA82867 C2 UA 82867C2
- Authority
- UA
- Ukraine
- Prior art keywords
- ylsulfanyl
- group
- pyridinecarboxamide
- triazol
- thiazol
- Prior art date
Links
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 510
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 101
- 150000003839 salts Chemical class 0.000 claims abstract description 80
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 10
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011593 sulfur Chemical group 0.000 claims abstract description 4
- -1 carbamoyloxy group Chemical group 0.000 claims description 643
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
- 108010021582 Glucokinase Proteins 0.000 claims description 38
- 102000030595 Glucokinase Human genes 0.000 claims description 36
- 125000003277 amino group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 16
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000335 thiazolyl group Chemical group 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 10
- SWHGADZUKYCULK-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1C1=NC=CS1 SWHGADZUKYCULK-UHFFFAOYSA-N 0.000 claims description 9
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 230000003914 insulin secretion Effects 0.000 claims description 6
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
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- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229940125396 insulin Drugs 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- JAGQJCICXSCFAM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-6-(1-methylimidazol-2-yl)sulfanyl-n-(4-methyl-1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound CC1=CSC(NC(=O)C=2C(=CC=C(SC=3N(C=CN=3)C)N=2)SC=2C=CC(F)=CC=2)=N1 JAGQJCICXSCFAM-UHFFFAOYSA-N 0.000 claims description 3
- 102000005157 Somatostatin Human genes 0.000 claims description 3
- 108010056088 Somatostatin Proteins 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 229910052751 metal Chemical group 0.000 claims description 3
- 239000002184 metal Chemical group 0.000 claims description 3
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 3
- 229960000553 somatostatin Drugs 0.000 claims description 3
- KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229940124828 glucokinase activator Drugs 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 108010045994 tricholysine Proteins 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
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- 230000003213 activating effect Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 477
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- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 121
- 238000005160 1H NMR spectroscopy Methods 0.000 description 104
- 239000000243 solution Substances 0.000 description 86
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- 238000005481 NMR spectroscopy Methods 0.000 description 60
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 59
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 53
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- 229920006395 saturated elastomer Polymers 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 35
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003034987 | 2003-02-13 | ||
| JP2003342860 | 2003-10-01 | ||
| JP2004014799 | 2004-01-22 | ||
| PCT/JP2004/001568 WO2004081001A1 (ja) | 2003-02-13 | 2004-02-13 | 新規２－ピリジンカルボキサミド誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA82867C2 true UA82867C2 (en) | 2008-05-26 |
Family
ID=32995582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200508682A UA82867C2 (en) | 2003-02-13 | 2004-02-13 | 2-pyridinecarboxamide derivatives |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US7629362B2 (xx) |
| EP (1) | EP1598349B1 (xx) |
| JP (1) | JP4400563B2 (xx) |
| KR (1) | KR20050101208A (xx) |
| AR (1) | AR045414A1 (xx) |
| AT (1) | ATE517887T1 (xx) |
| AU (2) | AU2004220234C1 (xx) |
| BR (1) | BRPI0407283A (xx) |
| CA (1) | CA2515841C (xx) |
| EC (1) | ECSP056016A (xx) |
| HK (1) | HK1088602A1 (xx) |
| IL (1) | IL169905A0 (xx) |
| MA (1) | MA27626A1 (xx) |
| MX (1) | MXPA05008619A (xx) |
| NO (1) | NO20054224L (xx) |
| NZ (1) | NZ540791A (xx) |
| PE (1) | PE20050194A1 (xx) |
| TW (1) | TWI336329B (xx) |
| UA (1) | UA82867C2 (xx) |
| WO (1) | WO2004081001A1 (xx) |
| ZA (1) | ZA200504852B (xx) |
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| US7879840B2 (en) | 2005-08-25 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US8022058B2 (en) | 2000-05-10 | 2011-09-20 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| PL375021A1 (en) | 2002-10-03 | 2005-11-14 | Novartis Ag | Substituted (thiazol-2-yl) -amide or sulfonamide as glycokinase activators useful in the treatment of type 2 diabetes |
| GB0226930D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| BRPI0407283A (pt) | 2003-02-13 | 2006-01-31 | Banyu Pharma Co Ltd | Composto, composição farmacêutica, e, agente ativador de glucoquinase, agentes terapêuticos e/ou agentes preventivos para diabetes melito e obesidade |
| CA2553160C (en) * | 2003-12-29 | 2010-09-28 | Banyu Pharmaceutical Co., Ltd. | 2-heteroaryl-substituted benzimidazole derivative |
| US8710045B2 (en) | 2004-01-22 | 2014-04-29 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the ryanodine receptors |
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| JP2011513253A (ja) * | 2008-02-27 | 2011-04-28 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 糖尿病を治療するためのカルボキサミド−ヘテロアリール誘導体 |
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| KR20140145624A (ko) | 2012-04-16 | 2014-12-23 | 카네크 파마 인코포레이티드 | Ptp-1b 억제제에 대한 전구체로서의 융합된 방향족 포스포네이트 유도체 |
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| EP3143013B1 (en) | 2014-05-13 | 2019-12-18 | Memorial Sloan Kettering Cancer Center | Hsp70 modulators and methods for making and using the same |
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| CN101068777A (zh) * | 2004-10-08 | 2007-11-07 | 万有制药株式会社 | 硫醚化合物的制备方法 |
| AR063028A1 (es) * | 2006-10-06 | 2008-12-23 | Banyu Pharma Co Ltd | Derivados heterociclicos de piridin-2-carboxamida activadores de glucoquinasas, utiles para el tratamiento de diabetes y obesidad y composiciones farmaceuticas que los contienen. |
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2004
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- 2004-02-13 TW TW093103493A patent/TWI336329B/zh not_active IP Right Cessation
- 2004-02-13 CA CA2515841A patent/CA2515841C/en not_active Expired - Fee Related
- 2004-02-13 UA UAA200508682A patent/UA82867C2/uk unknown
- 2004-02-13 EP EP04711025A patent/EP1598349B1/en not_active Expired - Lifetime
- 2004-02-13 MX MXPA05008619A patent/MXPA05008619A/es active IP Right Grant
- 2004-02-13 NZ NZ540791A patent/NZ540791A/en not_active IP Right Cessation
- 2004-02-13 JP JP2005503465A patent/JP4400563B2/ja not_active Expired - Fee Related
- 2004-02-13 WO PCT/JP2004/001568 patent/WO2004081001A1/ja active Application Filing
- 2004-02-13 AR ARP040100442A patent/AR045414A1/es unknown
- 2004-02-13 AT AT04711025T patent/ATE517887T1/de not_active IP Right Cessation
- 2004-02-13 PE PE2004000159A patent/PE20050194A1/es not_active Application Discontinuation
- 2004-02-13 KR KR1020057014827A patent/KR20050101208A/ko not_active Application Discontinuation
- 2004-02-13 AU AU2004220234A patent/AU2004220234C1/en not_active Ceased
- 2004-02-13 US US10/545,424 patent/US7629362B2/en active Active
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2005
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- 2005-07-26 IL IL169905A patent/IL169905A0/en unknown
- 2005-08-24 MA MA28455A patent/MA27626A1/fr unknown
- 2005-09-12 NO NO20054224A patent/NO20054224L/no not_active Application Discontinuation
- 2005-09-13 EC EC2005006016A patent/ECSP056016A/es unknown
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2006
- 2006-08-11 HK HK06108941A patent/HK1088602A1/xx not_active IP Right Cessation
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2009
- 2009-10-23 US US12/604,835 patent/US8344003B2/en active Active
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2010
- 2010-01-04 AU AU2010200004A patent/AU2010200004B2/en not_active Ceased
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2012
- 2012-11-27 US US13/685,775 patent/US8765789B2/en not_active Expired - Lifetime
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