JP2010518153A5 - - Google Patents
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- Publication number
- JP2010518153A5 JP2010518153A5 JP2009549445A JP2009549445A JP2010518153A5 JP 2010518153 A5 JP2010518153 A5 JP 2010518153A5 JP 2009549445 A JP2009549445 A JP 2009549445A JP 2009549445 A JP2009549445 A JP 2009549445A JP 2010518153 A5 JP2010518153 A5 JP 2010518153A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrimidin
- pyrrolo
- pyridine
- amino
- 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
- BHLOJNVPFCEQMK-UHFFFAOYSA-N 4-(4-cyclohexyloxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OC4CCCCC4)C=CN=C3NC=2)=N1 BHLOJNVPFCEQMK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 5
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- -1 methoxy, ethoxy, propoxy, butyloxy, isopropoxy, benzyloxy, cyclohexylmethoxy, cyclohexyloxy, 2-propylethynyl Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- SVMZPDAKMVKVTO-UHFFFAOYSA-N 3-[[3-(2-aminopyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]oxymethyl]phenol Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=C(O)C=CC=4)C=CN=C3NC=2)=N1 SVMZPDAKMVKVTO-UHFFFAOYSA-N 0.000 claims 1
- CJJMNECGBUPMAV-UHFFFAOYSA-N 4-(4-ethoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(OCC)=CC=NC=2NC=C1C1=CC=NC(N)=N1 CJJMNECGBUPMAV-UHFFFAOYSA-N 0.000 claims 1
- GGEWEQJWGGJUHO-UHFFFAOYSA-N 4-(4-methoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(OC)=CC=NC=2NC=C1C1=CC=NC(N)=N1 GGEWEQJWGGJUHO-UHFFFAOYSA-N 0.000 claims 1
- PEAOMBUSAQHKLH-UHFFFAOYSA-N 4-(4-pent-1-ynyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(C#CCCC)=CC=NC=2NC=C1C1=CC=NC(N)=N1 PEAOMBUSAQHKLH-UHFFFAOYSA-N 0.000 claims 1
- UKFAZKKKVOLGRD-UHFFFAOYSA-N 4-(4-pentyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(CCCCC)=CC=NC=2NC=C1C1=CC=NC(N)=N1 UKFAZKKKVOLGRD-UHFFFAOYSA-N 0.000 claims 1
- BHSLUMYWKBBOGQ-UHFFFAOYSA-N 4-(4-phenyl-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(C=4C=CC=CC=4)C=CN=C3NC=2)=N1 BHSLUMYWKBBOGQ-UHFFFAOYSA-N 0.000 claims 1
- NUWWZZWYLXOZSM-UHFFFAOYSA-N 4-(4-phenylmethoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=CC=CC=4)C=CN=C3NC=2)=N1 NUWWZZWYLXOZSM-UHFFFAOYSA-N 0.000 claims 1
- YRURITXEWXPMAI-UHFFFAOYSA-N 4-(4-propan-2-yloxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(OC(C)C)=CC=NC=2NC=C1C1=CC=NC(N)=N1 YRURITXEWXPMAI-UHFFFAOYSA-N 0.000 claims 1
- ZHMRPXZRUZLCNL-UHFFFAOYSA-N 4-(4-propoxy-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine Chemical compound C1=2C(OCCC)=CC=NC=2NC=C1C1=CC=NC(N)=N1 ZHMRPXZRUZLCNL-UHFFFAOYSA-N 0.000 claims 1
- LIEPLDVGRVNSDO-UHFFFAOYSA-N 4-[4-(2-phenylethyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(CCC=4C=CC=CC=4)C=CN=C3NC=2)=N1 LIEPLDVGRVNSDO-UHFFFAOYSA-N 0.000 claims 1
- KKPULEBJQJSKFA-UHFFFAOYSA-N 4-[4-(cyclohexylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC4CCCCC4)C=CN=C3NC=2)=N1 KKPULEBJQJSKFA-UHFFFAOYSA-N 0.000 claims 1
- CLKJYJQIRJVYBL-UHFFFAOYSA-N 4-[4-(piperidin-4-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC4CCNCC4)C=CN=C3NC=2)=N1 CLKJYJQIRJVYBL-UHFFFAOYSA-N 0.000 claims 1
- QGHVXQVFYLSNPO-UHFFFAOYSA-N 4-[4-(pyridazin-4-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=NN=CC=4)C=CN=C3NC=2)=N1 QGHVXQVFYLSNPO-UHFFFAOYSA-N 0.000 claims 1
- LMXCTMAUCHBLFV-UHFFFAOYSA-N 4-[4-(pyridin-2-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4N=CC=CC=4)C=CN=C3NC=2)=N1 LMXCTMAUCHBLFV-UHFFFAOYSA-N 0.000 claims 1
- FGYBJWNUACKVGS-UHFFFAOYSA-N 4-[4-(pyridin-3-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=NC=CC=4)C=CN=C3NC=2)=N1 FGYBJWNUACKVGS-UHFFFAOYSA-N 0.000 claims 1
- VZRMWEINDJDWDS-UHFFFAOYSA-N 4-[4-(pyridin-4-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=CN=CC=4)C=CN=C3NC=2)=N1 VZRMWEINDJDWDS-UHFFFAOYSA-N 0.000 claims 1
- HZDLYPCZQPALJH-UHFFFAOYSA-N 4-[4-(pyrimidin-5-ylmethoxy)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=NC=NC=4)C=CN=C3NC=2)=N1 HZDLYPCZQPALJH-UHFFFAOYSA-N 0.000 claims 1
- TZWMNYGBLZZRLB-UHFFFAOYSA-N 4-[4-[(1-methylsulfonylpiperidin-4-yl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCC1COC1=CC=NC2=C1C(C=1N=C(N)N=CC=1)=CN2 TZWMNYGBLZZRLB-UHFFFAOYSA-N 0.000 claims 1
- RQTUYGCORVAJKN-UHFFFAOYSA-N 4-[4-[(2-chlorophenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C(=CC=CC=4)Cl)C=CN=C3NC=2)=N1 RQTUYGCORVAJKN-UHFFFAOYSA-N 0.000 claims 1
- RMJKOCLAWPCAMZ-UHFFFAOYSA-N 4-[4-[(2-methoxyphenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound COC1=CC=CC=C1COC1=CC=NC2=C1C(C=1N=C(N)N=CC=1)=CN2 RMJKOCLAWPCAMZ-UHFFFAOYSA-N 0.000 claims 1
- RCWPVNKOVSTFPC-UHFFFAOYSA-N 4-[4-[(3-chlorophenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=C(Cl)C=CC=4)C=CN=C3NC=2)=N1 RCWPVNKOVSTFPC-UHFFFAOYSA-N 0.000 claims 1
- BZVCHUWRZYBNIH-UHFFFAOYSA-N 4-[4-[(3-fluorophenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=C(F)C=CC=4)C=CN=C3NC=2)=N1 BZVCHUWRZYBNIH-UHFFFAOYSA-N 0.000 claims 1
- VJBULJMRWHOXBY-UHFFFAOYSA-N 4-[4-[(3-methoxyphenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound COC1=CC=CC(COC=2C=3C(C=4N=C(N)N=CC=4)=CNC=3N=CC=2)=C1 VJBULJMRWHOXBY-UHFFFAOYSA-N 0.000 claims 1
- XMFGPQCAUPXJCG-UHFFFAOYSA-N 4-[4-[(4-chlorophenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=CC(Cl)=CC=4)C=CN=C3NC=2)=N1 XMFGPQCAUPXJCG-UHFFFAOYSA-N 0.000 claims 1
- GDAJWDIGHOMXMD-UHFFFAOYSA-N 4-[4-[(4-fluorophenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=CC(F)=CC=4)C=CN=C3NC=2)=N1 GDAJWDIGHOMXMD-UHFFFAOYSA-N 0.000 claims 1
- AGKXBXNGEDYTQQ-UHFFFAOYSA-N 4-[4-[(4-methoxyphenyl)methoxy]-1h-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1COC1=CC=NC2=C1C(C=1N=C(N)N=CC=1)=CN2 AGKXBXNGEDYTQQ-UHFFFAOYSA-N 0.000 claims 1
- VPBBLKWPGLGBPA-UHFFFAOYSA-N 4-[[3-(2-aminopyrimidin-4-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]oxymethyl]phenol Chemical compound NC1=NC=CC(C=2C3=C(OCC=4C=CC(O)=CC=4)C=CN=C3NC=2)=N1 VPBBLKWPGLGBPA-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000030761 polycystic kidney disease Diseases 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0701138A FR2912744B1 (fr) | 2007-02-16 | 2007-02-16 | Composes pyrrolo°2,3-b!pyridine,composes azaindoles utiles dans la synthese de ces composes pyrrolo°2,3-b!pyridine, leurs procedes de fabrication et leurs utilisations. |
| PCT/FR2008/000197 WO2008129152A1 (fr) | 2007-02-16 | 2008-02-14 | Composes pyrrolo[2,3-b]pyridine, composes azaindoles utiles dans la synthese de ces composes pyrrolo[2,3-b]pyridine, leurs procedes de fabrication et leurs utilisations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010518153A JP2010518153A (ja) | 2010-05-27 |
| JP2010518153A5 true JP2010518153A5 (enExample) | 2011-03-31 |
Family
ID=38515529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009549445A Pending JP2010518153A (ja) | 2007-02-16 | 2008-02-14 | ピロロ［２，３−ｂ］ピリジン化合物、該ピロロ［２，３−ｂ］ピリジン化合物を合成するために用いられるアザインドール化合物、それらの製造方法、及びそれらの使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20100184790A1 (enExample) |
| EP (1) | EP2125803B1 (enExample) |
| JP (1) | JP2010518153A (enExample) |
| CA (1) | CA2678007A1 (enExample) |
| FR (1) | FR2912744B1 (enExample) |
| WO (1) | WO2008129152A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110201599A1 (en) * | 2008-07-03 | 2011-08-18 | Exelixis, Inc. | CDK Modulators |
| CN102471339A (zh) * | 2009-07-15 | 2012-05-23 | 雅培制药有限公司 | 激酶的吡咯并吡啶抑制剂 |
| CA2878054C (en) | 2012-06-29 | 2018-09-11 | Pfizer Inc. | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| FR2999575A1 (fr) | 2012-12-18 | 2014-06-20 | Centre Nat Rech Scient | 3,5-diaryl-azaindoles comme inhibiteurs de la proteine dyrk1a pour le traitement des deficiences cognitives liees au syndrome de down et a la maladie d'alzheimer |
| WO2015092592A1 (en) * | 2013-12-17 | 2015-06-25 | Pfizer Inc. | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| TW201613919A (en) | 2014-07-02 | 2016-04-16 | Pharmacyclics Llc | Inhibitors of Bruton's tyrosine kinase |
| AU2016322813B2 (en) | 2015-09-14 | 2021-04-01 | Pfizer Inc. | Novel imidazo (4,5-c) quinoline and imidazo (4,5-c)(1,5) naphthyridine derivatives as LRRK2 inhibitors |
| FR3041640B1 (fr) * | 2015-09-30 | 2019-05-17 | Les Laboratoires Servier | NOUVEAUX DERIVES DE PYRROLO[2,3-d]PYRIMIDINE, LEUR PROCEDE DE PREPRATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
| EP3383875B1 (en) | 2015-11-30 | 2022-02-09 | Council Of Scientific & Industrial Research | 3-pyrimidinyl pyrrolo [2,3-b] pyridine as anticancer agents and the process for the preparation thereof |
| US10703757B2 (en) | 2016-12-23 | 2020-07-07 | Plexxikon Inc. | Compounds and methods for CDK8 modulation and indications therefor |
| CN110662745B (zh) * | 2017-03-23 | 2021-08-03 | 大邱庆北尖端医疗产业振兴财团 | 吡咯并吡啶衍生物、其制备方法、和用于预防或治疗蛋白激酶相关疾病的药物组合物 |
| CN111278840B (zh) * | 2017-08-18 | 2023-11-17 | 癌症研究科技有限公司 | 吡咯并[2，3-b]吡啶化合物及其治疗癌症的用途 |
| CN110759892B (zh) * | 2018-07-26 | 2022-09-13 | 南开大学 | Meridianin类衍生物及其制备和在防治植物病毒病菌病中的应用 |
| CN109096257B (zh) * | 2018-08-09 | 2020-02-21 | 山东博苑医药化学有限公司 | Meridianin类生物碱及其衍生物在防治植物病毒病菌病中的应用 |
| US12240844B2 (en) | 2019-01-18 | 2025-03-04 | Voronoi, Inc. | Pyrrolopyridine derivative and use thereof in prevention and treatment of protein kinase-related disease |
| CN109879874A (zh) * | 2019-03-05 | 2019-06-14 | 常州大学 | 一种Meriolin的合成方法 |
| KR20220081631A (ko) | 2020-12-09 | 2022-06-16 | 보로노이 주식회사 | 염증성 질환의 예방 및/또는 치료를 위한 피롤로-피리딘 유도체 화합물의 신규 용도 |
| US20240261297A1 (en) * | 2021-05-20 | 2024-08-08 | St. John's Cancer Institute | Anti-cdk inhibitors for cancer treatment |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7855205B2 (en) * | 2004-10-29 | 2010-12-21 | Janssen Pharmaceutica Nv | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| KR20080016643A (ko) * | 2005-05-16 | 2008-02-21 | 아이알엠 엘엘씨 | 단백질 키나제 억제제로서의 피롤로피리딘 유도체 |
| AU2006319233B9 (en) * | 2005-11-30 | 2011-09-29 | F. Hoffmann-La Roche Ag | 3-amino-2-arylpropyl azaindoles and uses thereof |
-
2007
- 2007-02-16 FR FR0701138A patent/FR2912744B1/fr not_active Expired - Fee Related
-
2008
- 2008-02-14 US US12/526,446 patent/US20100184790A1/en not_active Abandoned
- 2008-02-14 EP EP08775557.5A patent/EP2125803B1/fr not_active Not-in-force
- 2008-02-14 CA CA002678007A patent/CA2678007A1/fr not_active Abandoned
- 2008-02-14 JP JP2009549445A patent/JP2010518153A/ja active Pending
- 2008-02-14 WO PCT/FR2008/000197 patent/WO2008129152A1/fr not_active Ceased
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