JP2007523142A5 - - Google Patents
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- Publication number
- JP2007523142A5 JP2007523142A5 JP2006553652A JP2006553652A JP2007523142A5 JP 2007523142 A5 JP2007523142 A5 JP 2007523142A5 JP 2006553652 A JP2006553652 A JP 2006553652A JP 2006553652 A JP2006553652 A JP 2006553652A JP 2007523142 A5 JP2007523142 A5 JP 2007523142A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- oxy
- methylethyl
- benzamide
- methyl
- 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.)
- Pending
Links
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 28
- -1 4-{[(2-methoxyethyl) amino] carbonyl} phenoxy Chemical group 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 16
- 239000000651 prodrug Substances 0.000 claims 15
- 229940002612 prodrug Drugs 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 239000012453 solvate Substances 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- DCUCWQYSNMLTSW-UHFFFAOYSA-N 3-(1-methoxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)-n-(1,3-thiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC=CN=2)=CC(OC(C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 DCUCWQYSNMLTSW-UHFFFAOYSA-N 0.000 claims 1
- NUALTPCPNHRBSF-AWEZNQCLSA-N 3-(4-carbamoylphenoxy)-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1-methylpyrazol-3-yl)benzamide Chemical compound C=1C(C(=O)NC2=NN(C)C=C2)=CC(O[C@@H](C)COC)=CC=1OC1=CC=C(C(N)=O)C=C1 NUALTPCPNHRBSF-AWEZNQCLSA-N 0.000 claims 1
- VCWRVIINXRSQFD-HNNXBMFYSA-N 3-(4-cyanophenoxy)-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1-methylpyrazol-3-yl)benzamide Chemical compound C=1C(C(=O)NC2=NN(C)C=C2)=CC(O[C@@H](C)COC)=CC=1OC1=CC=C(C#N)C=C1 VCWRVIINXRSQFD-HNNXBMFYSA-N 0.000 claims 1
- FPPCRNXDOLCAQE-HNNXBMFYSA-N 3-(4-ethylsulfonylphenoxy)-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1,3-thiazol-2-yl)benzamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=CC(O[C@@H](C)COC)=CC(C(=O)NC=2SC=CN=2)=C1 FPPCRNXDOLCAQE-HNNXBMFYSA-N 0.000 claims 1
- KLVGOLJETLMIKB-AWEZNQCLSA-N 3-[(2s)-1-methoxypropan-2-yl]oxy-5-(4-methylsulfonylphenoxy)-n-(1h-pyrazol-5-yl)benzamide Chemical compound C=1C(C(=O)NC2=NNC=C2)=CC(O[C@@H](C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 KLVGOLJETLMIKB-AWEZNQCLSA-N 0.000 claims 1
- LBTBODJHUUBMJW-HNNXBMFYSA-N 3-[(2s)-1-methoxypropan-2-yl]oxy-n-(5-methyl-1h-pyrazol-3-yl)-5-(4-methylsulfonylphenoxy)benzamide Chemical compound C=1C(C(=O)NC2=NNC(C)=C2)=CC(O[C@@H](C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 LBTBODJHUUBMJW-HNNXBMFYSA-N 0.000 claims 1
- JDYASPCTKTYZOY-INIZCTEOSA-N 3-[3-(1h-imidazol-2-ylmethylcarbamoyl)phenoxy]-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1,3-thiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC=CN=2)=CC(O[C@@H](C)COC)=CC=1OC(C=1)=CC=CC=1C(=O)NCC1=NC=CN1 JDYASPCTKTYZOY-INIZCTEOSA-N 0.000 claims 1
- QEKBHTFYTQARSP-INIZCTEOSA-N 3-[4-(1h-imidazol-2-ylmethylcarbamoyl)phenoxy]-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1,3-thiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC=CN=2)=CC(O[C@@H](C)COC)=CC=1OC(C=C1)=CC=C1C(=O)NCC1=NC=CN1 QEKBHTFYTQARSP-INIZCTEOSA-N 0.000 claims 1
- BZRADHQFAIUNIU-HNNXBMFYSA-N 3-[4-(azetidine-1-carbonyl)-2-fluorophenoxy]-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1h-pyrazol-5-yl)benzamide Chemical compound C=1C(C(=O)NC2=NNC=C2)=CC(O[C@@H](C)COC)=CC=1OC(C(=C1)F)=CC=C1C(=O)N1CCC1 BZRADHQFAIUNIU-HNNXBMFYSA-N 0.000 claims 1
- ZZXIEXAOYBEXJO-INIZCTEOSA-N 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1,3-thiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC=CN=2)=CC(O[C@@H](C)COC)=CC=1OC(C=C1)=CC=C1C(=O)N1CCC1 ZZXIEXAOYBEXJO-INIZCTEOSA-N 0.000 claims 1
- AWRORTBBVHJYIA-INIZCTEOSA-N 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(2s)-1-methoxypropan-2-yl]oxy-n-(1h-pyrazol-5-yl)benzamide Chemical compound C=1C(C(=O)NC2=NNC=C2)=CC(O[C@@H](C)COC)=CC=1OC(C=C1)=CC=C1C(=O)N1CCC1 AWRORTBBVHJYIA-INIZCTEOSA-N 0.000 claims 1
- WZPBRMQZMJWFGY-UHFFFAOYSA-N 5-(1-methoxypropan-2-yloxy)-3-(4-methylsulfonylphenoxy)-2-(1h-pyrazol-5-yl)benzamide Chemical compound C=1C=NNC=1C=1C(C(N)=O)=CC(OC(C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 WZPBRMQZMJWFGY-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- HKXMYFNBGJSFMG-UHFFFAOYSA-N n-(1-methylpyrazol-3-yl)benzamide Chemical compound CN1C=CC(NC(=O)C=2C=CC=CC=2)=N1 HKXMYFNBGJSFMG-UHFFFAOYSA-N 0.000 claims 1
- RUPAHOYIIKNMTN-UHFFFAOYSA-N n-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide Chemical compound CC1=NSC(NC(=O)C=2C=CC=CC=2)=N1 RUPAHOYIIKNMTN-UHFFFAOYSA-N 0.000 claims 1
- KGDDBWOFFAWDJA-UHFFFAOYSA-N n-(5-methyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound S1C(C)=NN=C1NC(=O)C1=CC=CC=C1 KGDDBWOFFAWDJA-UHFFFAOYSA-N 0.000 claims 1
- PZGINHMSGKIADC-UHFFFAOYSA-N n-[3-(hydroxymethyl)-1,2,4-thiadiazol-5-yl]-3-(1-methoxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)benzamide Chemical compound C=1C(C(=O)NC=2SN=C(CO)N=2)=CC(OC(C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 PZGINHMSGKIADC-UHFFFAOYSA-N 0.000 claims 1
- CGCDPBXNTVCGFQ-UHFFFAOYSA-N n-[4-(1-hydroxyethyl)-1,3-thiazol-2-yl]-3-(1-methoxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC=C(N=2)C(C)O)=CC(OC(C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 CGCDPBXNTVCGFQ-UHFFFAOYSA-N 0.000 claims 1
- VRXGXOSFYDXUIW-UHFFFAOYSA-N n-[4-(hydroxymethyl)-1,3-thiazol-2-yl]-3-(1-methoxypropan-2-yloxy)-5-(4-methylsulfonylphenoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC=C(CO)N=2)=CC(OC(C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 VRXGXOSFYDXUIW-UHFFFAOYSA-N 0.000 claims 1
- RMMOJCLYEVNQHZ-HNNXBMFYSA-N n-[4-(methoxymethyl)-1,3-thiazol-2-yl]-3-[(2s)-1-methoxypropan-2-yl]oxy-5-(4-methylsulfonylphenoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC=C(COC)N=2)=CC(O[C@@H](C)COC)=CC=1OC1=CC=C(S(C)(=O)=O)C=C1 RMMOJCLYEVNQHZ-HNNXBMFYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 0 CC(/C=C/*1*CN)(/C=C/C=C1/Oc1cc(*)cc(C(NC2CCCCCCCCC2)=O)c1)N Chemical compound CC(/C=C/*1*CN)(/C=C/C=C1/Oc1cc(*)cc(C(NC2CCCCCCCCC2)=O)c1)N 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0403593A GB0403593D0 (en) | 2004-02-18 | 2004-02-18 | Compounds |
| GB0413386A GB0413386D0 (en) | 2004-06-16 | 2004-06-16 | Compounds |
| GB0423039A GB0423039D0 (en) | 2004-10-16 | 2004-10-16 | Compounds |
| PCT/GB2005/000545 WO2005080359A1 (en) | 2004-02-18 | 2005-02-15 | Benzamide derivatives and their use as glucokinae activating agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007523142A JP2007523142A (ja) | 2007-08-16 |
| JP2007523142A5 true JP2007523142A5 (enExample) | 2008-03-21 |
Family
ID=34890799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006553652A Pending JP2007523142A (ja) | 2004-02-18 | 2005-02-15 | ベンズアミド誘導体、およびグルコキナーゼ活性化物質としてのそれらの使用 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US20080280872A1 (enExample) |
| EP (2) | EP1718624B1 (enExample) |
| JP (1) | JP2007523142A (enExample) |
| KR (1) | KR20070007103A (enExample) |
| AR (1) | AR047678A1 (enExample) |
| AT (1) | ATE426597T1 (enExample) |
| AU (1) | AU2005214132B9 (enExample) |
| BR (1) | BRPI0507746A (enExample) |
| CA (1) | CA2554310A1 (enExample) |
| DE (1) | DE602005013491D1 (enExample) |
| ES (1) | ES2322709T3 (enExample) |
| IL (1) | IL177216A0 (enExample) |
| NO (1) | NO20063452L (enExample) |
| RU (1) | RU2392275C2 (enExample) |
| TW (1) | TW200602028A (enExample) |
| UY (1) | UY28756A1 (enExample) |
| WO (1) | WO2005080359A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0102299D0 (sv) | 2001-06-26 | 2001-06-26 | Astrazeneca Ab | Compounds |
| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| MXPA05008619A (es) | 2003-02-13 | 2005-11-04 | Banyu Pharma Co Ltd | Derivados novedosos de 2-piridincarboxamida. |
| EP1600442B1 (en) * | 2003-02-26 | 2018-01-17 | Msd K.K. | Heteroarylcarbamoylbenzene derivative |
| EP1718624B1 (en) * | 2004-02-18 | 2009-03-25 | AstraZeneca AB | Benzamide derivatives and their use as glucokinase activating agents |
| TW200600086A (en) * | 2004-06-05 | 2006-01-01 | Astrazeneca Ab | Chemical compound |
| CA2581619A1 (en) * | 2004-10-16 | 2006-04-20 | Astrazeneca Ab | Process for making phenoxy benzamide compounds |
| GB0423043D0 (en) * | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| GB0423042D0 (en) * | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Chemical process |
| GB0423044D0 (en) * | 2004-10-16 | 2004-11-17 | Astrazeneca Ab | Compounds |
| TW200714597A (en) * | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
| NZ564608A (en) * | 2005-07-09 | 2009-09-25 | Astrazeneca Ab | Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes |
| AU2006299091A1 (en) | 2005-09-29 | 2007-04-12 | Sanofi-Aventis | Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| US20070197532A1 (en) * | 2005-11-18 | 2007-08-23 | Cao Sheldon X | Glucokinase activators |
| TW200738621A (en) * | 2005-11-28 | 2007-10-16 | Astrazeneca Ab | Chemical process |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| US7910747B2 (en) | 2006-07-06 | 2011-03-22 | Bristol-Myers Squibb Company | Phosphonate and phosphinate pyrazolylamide glucokinase activators |
| CA2657566A1 (en) | 2006-07-24 | 2008-01-31 | F. Hoffmann-La Roche Ag | Pyrazoles as glucokinase activators |
| SA07280576B1 (ar) * | 2006-10-26 | 2011-06-22 | استرازينيكا ايه بي | مركبات بنزويل أمينو سيكليل غير متجانسة بأعتبارها عوامل منشطة للجلوكوكيناز |
| JP2010513445A (ja) * | 2006-12-21 | 2010-04-30 | アストラゼネカ アクチボラグ | Ｇｌｋアクチベーターとして有用な新規結晶性化合物 |
| JP2010534722A (ja) | 2007-07-27 | 2010-11-11 | ブリストル−マイヤーズ スクイブ カンパニー | 新規グルコキナーゼ活性化薬およびその使用方法 |
| AU2008310115B2 (en) | 2007-10-09 | 2013-06-27 | Merck Patent Gmbh | N- ( pyrazole- 3 -yl) -benzamide derivatives as glucokinase activators |
| BRPI0908124A2 (pt) * | 2008-02-06 | 2015-08-04 | Daiichi Sankyo Co Ltd | Composto, ativador de glucoquinase, composição farmacêutica, uso de um composto ou sal farmacologicamente aceitavél do mesmo, e, métodos de ativação da glucoquinase, e para tratar e/ou prevenir uma doença |
| WO2009106209A1 (en) * | 2008-02-27 | 2009-09-03 | Merck Patent Gmbh | Carboxamide-heteroaryl derivatives for the treatment of diabetes |
| US7741327B2 (en) | 2008-04-16 | 2010-06-22 | Hoffmann-La Roche Inc. | Pyrrolidinone glucokinase activators |
| US8258134B2 (en) | 2008-04-16 | 2012-09-04 | Hoffmann-La Roche Inc. | Pyridazinone glucokinase activators |
| JP2011529955A (ja) | 2008-08-04 | 2011-12-15 | アストラゼネカ アクチボラグ | 治療薬４１４ |
| WO2010082601A1 (ja) * | 2009-01-16 | 2010-07-22 | 第一三共株式会社 | 新規２，５－二置換ピロール誘導体 |
| GB0902434D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Chemical process |
| GB0902406D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Crystalline polymorphic form |
| WO2010116176A1 (en) * | 2009-04-09 | 2010-10-14 | Astrazeneca Ab | Pyrazolo [4, 5-e] pyrimidine derivative and its use to treat diabetes and obesity |
| WO2010116177A1 (en) | 2009-04-09 | 2010-10-14 | Astrazeneca Ab | A pyrazolo [4,5-e] pyrimidine derivative and its use to treat diabetes and obesity |
| JPWO2010128595A1 (ja) * | 2009-05-07 | 2012-11-01 | 富士フイルムＲｉファーマ株式会社 | 放射性ヨウ素標識イミダゾピリジン誘導体の製造法 |
| EP2445908A1 (en) | 2009-06-22 | 2012-05-02 | Cadila Healthcare Limited | Disubstituted benzamide derivatives as glucokinase (gk) activators |
| MX2012001228A (es) | 2009-07-31 | 2012-04-20 | Cadila Healthcare Ltd | Derivados de benzamida sustituidos como activadores de glucocinasa (gk). |
| KR20120120204A (ko) * | 2009-12-11 | 2012-11-01 | 아스텔라스세이야쿠 가부시키가이샤 | 벤즈아미드 화합물 |
| US8222416B2 (en) | 2009-12-14 | 2012-07-17 | Hoffmann-La Roche Inc. | Azaindole glucokinase activators |
| WO2011122458A1 (ja) * | 2010-03-29 | 2011-10-06 | 第一三共株式会社 | 含窒素芳香環化合物 |
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-
2005
- 2005-02-15 EP EP05708360A patent/EP1718624B1/en not_active Expired - Lifetime
- 2005-02-15 WO PCT/GB2005/000545 patent/WO2005080359A1/en not_active Ceased
- 2005-02-15 JP JP2006553652A patent/JP2007523142A/ja active Pending
- 2005-02-15 BR BRPI0507746-0A patent/BRPI0507746A/pt not_active IP Right Cessation
- 2005-02-15 CA CA002554310A patent/CA2554310A1/en not_active Abandoned
- 2005-02-15 KR KR1020067019123A patent/KR20070007103A/ko not_active Ceased
- 2005-02-15 DE DE602005013491T patent/DE602005013491D1/de not_active Expired - Lifetime
- 2005-02-15 US US10/588,334 patent/US20080280872A1/en not_active Abandoned
- 2005-02-15 AT AT05708360T patent/ATE426597T1/de not_active IP Right Cessation
- 2005-02-15 RU RU2006130684/04A patent/RU2392275C2/ru not_active IP Right Cessation
- 2005-02-15 AU AU2005214132A patent/AU2005214132B9/en not_active Ceased
- 2005-02-15 EP EP08158356A patent/EP2048137A1/en not_active Withdrawn
- 2005-02-15 ES ES05708360T patent/ES2322709T3/es not_active Expired - Lifetime
- 2005-02-16 AR ARP050100540A patent/AR047678A1/es not_active Application Discontinuation
- 2005-02-17 UY UY28756A patent/UY28756A1/es unknown
- 2005-02-17 TW TW094104677A patent/TW200602028A/zh unknown
-
2006
- 2006-07-26 NO NO20063452A patent/NO20063452L/no not_active Application Discontinuation
- 2006-08-01 IL IL177216A patent/IL177216A0/en unknown
-
2010
- 2010-03-12 US US12/722,936 patent/US20110034432A1/en not_active Abandoned
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