HRP20110755T1 - Novi derivati diazenij-diolata, postupak za njegovu pripravu i farmaceutski pripravci koji ga sadržavaju - Google Patents
Novi derivati diazenij-diolata, postupak za njegovu pripravu i farmaceutski pripravci koji ga sadržavaju Download PDFInfo
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- HRP20110755T1 HRP20110755T1 HR20110755T HRP20110755T HRP20110755T1 HR P20110755 T1 HRP20110755 T1 HR P20110755T1 HR 20110755 T HR20110755 T HR 20110755T HR P20110755 T HRP20110755 T HR P20110755T HR P20110755 T1 HRP20110755 T1 HR P20110755T1
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- 238000000034 method Methods 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- MUMXDRRTIYLYMY-YJKCNMNRSA-N (Z)-[dodecyl-[6-(dodecylazaniumyl)hexyl]amino]-oxido-oxidoiminoazanium Chemical class CCCCCCCCCCCC[NH2+]CCCCCCN(CCCCCCCCCCCC)[N+](\[O-])=N\[O-] MUMXDRRTIYLYMY-YJKCNMNRSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 15
- 239000002253 acid Substances 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 11
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract 2
- -1 {[(1Z)-2,2-diethyl-1-oxidohydrazono]amino}oxy Chemical group 0.000 claims 10
- 238000009833 condensation Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010003178 Arterial thrombosis Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010030043 Ocular hypertension Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 206010003230 arteritis Diseases 0.000 claims 1
- 230000007214 atherothrombosis Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical group NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000007232 portal hypertension Diseases 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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Abstract
Spojevi formule (I): naznačeni time, da: R1 predstavlja atom vodika ili skupinu -COOR, gdje R predstavlja skupinu ravni ili razgranani (C1-C6)alkil ili skupinu aril-(C1-C6)alkil u kojoj alkilni dio može biti ravan ili razgranan, R2 predstavlja skupinu G ili skupinu ravni ili razgranani (C1-C6)alkil koja je supstituirana skupinom G, gdje G predstavlja skupinu -(CH2)n-A-(CH2)m-B-(CR4R5)p-(CH2)o-R6 u kojoj: - n je0, 1, 2 ili 3, - m je0, 1, 2 ili 3, - p je 0 ili 1, - o je 0, 1 ili 2, - R4 i R5, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil, u kojoj se jedna od skupina -CH2- ili -CR4R5- lanca G na isti način može zamijeniti, prema potrebi, fenilenom, skupinom -PhC(O)- ili -PhC(O)O- (gdje Ph označava fenil), - A i B, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja vezu, atom dušika ili skupinu: gdje R7 predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil, - a R6 predstavlja skupinugdje R8, R9 i R10, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil koja je nesupstituirana ili supstituirana amino skupinom, ili R8 i R9 zajedno tvore ravni ili razgranani (C1-C6)alkilenski lanac, R3 predstavlja atom vodika, skupinu ravni ili razgranani (C1-C6)alkil ili skupinu NO2,njihove enantiomere i dijastereoizomere kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom. Patent sadrži još 14 patentnih zahtjeva.
Claims (15)
1. Spojevi formule (I):
[image]
naznačeni time, da:
R1 predstavlja atom vodika ili skupinu -COOR, gdje R predstavlja skupinu ravni ili razgranani (C1-C6)alkil ili skupinu aril-(C1-C6)alkil u kojoj alkilni dio može biti ravan ili razgranan,
R2 predstavlja skupinu G ili skupinu ravni ili razgranani (C1-C6)alkil koja je supstituirana skupinom G, gdje G predstavlja skupinu -(CH2)n-A-(CH2)m-B-(CR4R5)p-(CH2)o-R6 u kojoj:
- n je0, 1, 2 ili 3,
- m je0, 1, 2 ili 3,
- p je 0 ili 1,
- o je 0, 1 ili 2,
- R4 i R5, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil, u kojoj se jedna od skupina -CH2- ili -CR4R5- lanca G na isti način može zamijeniti, prema potrebi, fenilenom, skupinom -PhC(O)- ili -PhC(O)O- (gdje Ph označava fenil),
- A i B, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja vezu, atom dušika ili skupinu:
[image]
gdje R7 predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil,
- a R6 predstavlja skupinu
[image]
gdje R8, R9 i R10, koji mogu biti jednaki ili različiti, svaki za sebe predstavlja atom vodika ili skupinu ravni ili razgranani (C1-C6)alkil koja je nesupstituirana ili supstituirana amino skupinom, ili R8 i R9 zajedno tvore ravni ili razgranani (C1-C6)alkilenski lanac,
R3 predstavlja atom vodika, skupinu ravni ili razgranani (C1-C6)alkil ili skupinu NO2,
njihove enantiomere i dijastereoizomere kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
2. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R1 predstavlja atom vodika, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
3. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R3 predstavlja atom vodika, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
4. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R3 predstavlja skupinu NO2, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
5. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R2 predstavlja skupinu:
[image]
ili —CH2—R6, gdje je R6 definiran jednako kao u patentnom zahtjevu 1, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
6. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R6 predstavlja skupinu -O-N=N(O)-NR8R9, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
7. Spojevi formule (I) u skladu s patentnim zahtjevom 1, naznačeni time, da R8 i R9 predstavljaju skupinu ravni (C1-C6)alkil, njihovi enantiomeri i dijastereoizomeri kao i njihove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
8. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je to spoj ({[(1Z)-2,2-dietil-1-oksidohidrazono]amino}oksi)metil 3-{[({2-kloro-5-[(2-metil-5-nitro-2,3-dihidro-1H-indol-1-il)karbamoil]fenil}sulfonil)amino]metil}benzoat, njegovi enantiomeri i dijastereoizomeri kao i njegove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
9. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je to spoj ({[(1Z)-2,2-dietil-1-oksido-hidrazono]amino}oksi)metil 4{[({2-kloro-5-[(2-metil-2,3-dihidro-1H-indol-1-il)karbamoil]fenil}sulfonil)amino]metil}benzoat, njegovi enantiomeri i dijastereoizomeri kao i njegove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
10. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je to spoj ({[(1Z)-2,2-dietil-1-oksidohidrazono]amino}oksi)metil 4-({[(2-kloro-5-{[(2R)-2-metil-2,3-dihidro-1H-indol-1-il]karbamoil}fenil)sulfonil]amino}metil)benzoat, kao i njegove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
11. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je to spoj ({[(1Z)-2,2-dietil-1-oksidohidrazono]amino}oksi)metil4{2-[({2-kloro-5-[(2-metil-2,3-dihidro-1H-indol-1-il)karbamoil]fenil}sulfonil)amino]etil}benzoat, njegovi enantiomeri i dijastereoizomeri kao i njegove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
12. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je to spoj ({[(1Z)-2,2-dietil-1-oksidohidrazono]amino}oksi)metil 4{2-[({2-kloro-5-[((2R)-2-metil-2,3-dihidro-1H-indol-1-il)karbamoil]fenil}sulfonil)amino]etil}benzoat, kao i njegove adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
13. Postupak priprave spojevA formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da se kao početna tvar koristi spoj formule (II):
[image]
gdje je R3 definiran jednako kao u formuli (I),
koji se podvrgava kondenzaciji sa spojem formule (III):
[image]
gdje je R definiran jednako kao u formuli (I), čime se dobiva spoj formule (IV):
[image]
gdje su R3 i R definirani jednako kao u prethodnim slučajevima,
koji se podvrgava kondenzaciji, u prisutnosti baze, sa spojem formule (V):
X—R2 (V)
gdje je R2 definiran jednako kao u formuli (I), a X predstavlja atom halogena, čime se dobiva spoj formule (l/a), koji je poseban slučaj spojeva formule (I):
[image]
gdje su R, R2 i R3 definirani jednako kao u formuli (I),
a također je moguće dobiti spojeve formule (I/a) kondenzacijom spoja formule Cl-(CH2)O-R6, gdje su o i R6 definirani jednako kao u formuli (I), s karboksilnom ili fosforamidnom funkcijom prisutnom u skupini G, a ti se spojevi (I/a) po izboru mogu zagrijavati u kiseloj sredini, čime se dobiva spoj formule (I/b), koji je poseban slučaj spojeva formule (I):
[image]
gdje su R2 i R3 definirani jednako kao u formuli (I),
spojevi formula (I/a) i (I/b), koji zajedno čine spojeve formule (I), pročišćavaju se, prema potrebi, konvencionalnim tehnikama pročišćavanja, po izboru se razdvajaju u izomere konvencionalnim tehnikama razdvajanja i prema potrebi se prevode u adicijske soli s farmaceutski prihvatljivom kiselinom ili bazom.
14. Farmaceutski pripravci, naznačeni time, da kao djelatnu tvar sadržavaju spoj u skladu s bilo kojim patentnim zahtjevom od 1 do 12 u kombinaciji s jednim ili više s farmaceutski prihvatljivih, inertnih, netoksičnih ekscipijensa ili nosača.
15. Farmaceutski pripravci u skladu s patentnim zahtjevom 14, naznačeni time, da sadržavaju najmanje jednu djelatnu tvar u skladu s bilo kojim patentnim zahtjevom od 1 do 12 te da se koriste kao lijek za liječenje hipertenzije i kardiovaskularnih patologija i komplikacija, primjerice retinopatije, cerebralnih incidenata, demencije, hipertrofije lijeve klijetke, zatajenja srca, angine pectoris, infarkta miokarda i nefropatije; za liječenje kardiovaskularnih patologija povezanih s aterotrombozom kao što su cerebralni I srčani incidenti, arteritis i vaskulopatije; za liječenje vaskularnih komplikacija mnogobrojnih poremećaja poput dijabetesa, pretilosti, metaboličkog sindroma, karcinoma ili fibroze jetre; te za liječenje pulmonalne, okularne ili portalne hipertenzije.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0708604A FR2924713B1 (fr) | 2007-12-11 | 2007-12-11 | Nouveaux derives diazeniumdiolates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2008/001716 WO2009103875A1 (fr) | 2007-12-11 | 2008-12-10 | Nouveaux derives diazeniumdiolates, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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| Publication Number | Publication Date |
|---|---|
| HRP20110755T1 true HRP20110755T1 (hr) | 2011-11-30 |
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| HR20110755T HRP20110755T1 (hr) | 2007-12-11 | 2011-10-17 | Novi derivati diazenij-diolata, postupak za njegovu pripravu i farmaceutski pripravci koji ga sadržavaju |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8288433B2 (hr) |
| EP (1) | EP2231598B1 (hr) |
| JP (1) | JP5247814B2 (hr) |
| KR (1) | KR20100083195A (hr) |
| CN (1) | CN101910128B (hr) |
| AR (1) | AR069643A1 (hr) |
| AT (1) | ATE520658T1 (hr) |
| AU (1) | AU2008351147B2 (hr) |
| BR (1) | BRPI0822066A2 (hr) |
| CA (1) | CA2707853C (hr) |
| DK (1) | DK2231598T3 (hr) |
| EA (1) | EA201000885A1 (hr) |
| ES (1) | ES2371699T3 (hr) |
| FR (1) | FR2924713B1 (hr) |
| GE (1) | GEP20135733B (hr) |
| HR (1) | HRP20110755T1 (hr) |
| MA (1) | MA31901B1 (hr) |
| MX (1) | MX2010006446A (hr) |
| MY (1) | MY147973A (hr) |
| NZ (1) | NZ586070A (hr) |
| PL (1) | PL2231598T3 (hr) |
| PT (1) | PT2231598E (hr) |
| RS (1) | RS52001B (hr) |
| SI (1) | SI2231598T1 (hr) |
| UA (1) | UA97035C2 (hr) |
| WO (1) | WO2009103875A1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011053519A1 (en) * | 2009-10-29 | 2011-05-05 | Merck Sharp & Dohme Corp. | Diuretics |
| CN102883610A (zh) | 2010-02-12 | 2013-01-16 | 默沙东公司 | 二醇二氮烯*环戊基衍生物 |
| EP2571351B1 (en) * | 2010-05-21 | 2016-09-14 | Merck Sharp & Dohme Corp. | Diazeniumdiolate cyclohexyl derivatives |
| CA2814752A1 (en) | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | Diazeniumdiolate heterocyclic derivatives |
| JO3350B1 (ar) | 2011-03-07 | 2019-03-13 | Merck Sharp & Dohme | مشتقات حلقية غير متجانسة محتوية على مجموعات أمينو أولية ومركبات داي أزينيومديولات |
| US9272987B2 (en) | 2011-05-02 | 2016-03-01 | Merck Sharp & Dohme Corp. | Diazeniumdiolate cyclohexyl derivatives |
| CN109608371B (zh) * | 2019-01-16 | 2020-12-29 | 泰州学院 | O2-4-(3-(4-胺磺酰基苯基)脲)苯基偶氮鎓二醇盐衍生物、制备方法及用途 |
| CN114805183B (zh) * | 2022-05-07 | 2022-12-27 | 武汉科技大学 | 一类no供体型荜茇酰胺衍生物、制备方法及用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1203691A (en) * | 1968-03-06 | 1970-09-03 | Science Union & Cie | New disubstituted n-amino indoline derivatives and process for preparing them |
| JPH0233030B2 (ja) * | 1982-01-18 | 1990-07-25 | Mitsui Toatsu Chemicals | Surufuamoiruansokukosanjudotaioyobisoreojukoseibuntoshitefukumuchiryoyososeibutsu |
| JPH07118231A (ja) * | 1993-10-22 | 1995-05-09 | Nippon Oil & Fats Co Ltd | スルファモイル安息香酸誘導体 |
| US5958427A (en) * | 1996-11-08 | 1999-09-28 | Salzman; Andrew L. | Nitric oxide donor compounds and pharmaceutical compositions for pulmonary hypertension and other indications |
| AUPS236902A0 (en) * | 2002-05-16 | 2002-06-13 | Northern Sydney Area Health Service | Composition and method for treating hypertension |
| CA2574535A1 (en) * | 2004-11-15 | 2006-05-26 | Nitromed, Inc. | Diuretic compounds comprising heterocyclic nitric oxide donor groups, compositions and methods of use |
| WO2006091716A2 (en) * | 2005-02-24 | 2006-08-31 | Nitromed, Inc. | Nitric oxide enhancing diuretic compounds, compositions and methods of use |
| JP2011510082A (ja) * | 2008-01-24 | 2011-03-31 | メルク・シャープ・エンド・ドーム・コーポレイション | アンジオテンシンｉｉ受容体拮抗薬 |
| EP2250168B1 (en) * | 2008-02-08 | 2014-11-19 | Merck Sharp & Dohme Corp. | Angiotensin ii receptor antagonists |
-
2007
- 2007-12-11 FR FR0708604A patent/FR2924713B1/fr not_active Expired - Fee Related
-
2008
- 2008-12-10 AT AT08872697T patent/ATE520658T1/de active
- 2008-12-10 DK DK08872697.1T patent/DK2231598T3/da active
- 2008-12-10 UA UAA201008615A patent/UA97035C2/ru unknown
- 2008-12-10 SI SI200830404T patent/SI2231598T1/sl unknown
- 2008-12-10 AU AU2008351147A patent/AU2008351147B2/en not_active Ceased
- 2008-12-10 GE GEAP200811874A patent/GEP20135733B/en unknown
- 2008-12-10 ES ES08872697T patent/ES2371699T3/es active Active
- 2008-12-10 CN CN2008801229307A patent/CN101910128B/zh not_active Expired - Fee Related
- 2008-12-10 CA CA2707853A patent/CA2707853C/fr not_active Expired - Fee Related
- 2008-12-10 US US12/735,048 patent/US8288433B2/en not_active Expired - Fee Related
- 2008-12-10 MY MYPI2010002633A patent/MY147973A/en unknown
- 2008-12-10 EP EP08872697A patent/EP2231598B1/fr active Active
- 2008-12-10 PT PT08872697T patent/PT2231598E/pt unknown
- 2008-12-10 NZ NZ586070A patent/NZ586070A/en not_active IP Right Cessation
- 2008-12-10 JP JP2010537487A patent/JP5247814B2/ja not_active Expired - Fee Related
- 2008-12-10 KR KR1020107012930A patent/KR20100083195A/ko active IP Right Grant
- 2008-12-10 WO PCT/FR2008/001716 patent/WO2009103875A1/fr active Application Filing
- 2008-12-10 PL PL08872697T patent/PL2231598T3/pl unknown
- 2008-12-10 BR BRPI0822066A patent/BRPI0822066A2/pt not_active IP Right Cessation
- 2008-12-10 MX MX2010006446A patent/MX2010006446A/es active IP Right Grant
- 2008-12-10 RS RS20110438A patent/RS52001B/en unknown
- 2008-12-10 EA EA201000885A patent/EA201000885A1/ru unknown
- 2008-12-11 AR ARP080105371A patent/AR069643A1/es not_active Application Discontinuation
-
2010
- 2010-06-07 MA MA32894A patent/MA31901B1/fr unknown
-
2011
- 2011-10-17 HR HR20110755T patent/HRP20110755T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MA31901B1 (fr) | 2010-12-01 |
| UA97035C2 (ru) | 2011-12-26 |
| AR069643A1 (es) | 2010-02-10 |
| MY147973A (en) | 2013-02-28 |
| PL2231598T3 (pl) | 2011-12-30 |
| JP5247814B2 (ja) | 2013-07-24 |
| CA2707853C (fr) | 2013-02-05 |
| CN101910128B (zh) | 2013-01-16 |
| EA201000885A1 (ru) | 2011-02-28 |
| EP2231598B1 (fr) | 2011-08-17 |
| CN101910128A (zh) | 2010-12-08 |
| CA2707853A1 (fr) | 2009-08-27 |
| PT2231598E (pt) | 2011-10-11 |
| US20100286225A1 (en) | 2010-11-11 |
| MX2010006446A (es) | 2010-07-05 |
| ATE520658T1 (de) | 2011-09-15 |
| EP2231598A1 (fr) | 2010-09-29 |
| DK2231598T3 (da) | 2011-12-05 |
| FR2924713A1 (fr) | 2009-06-12 |
| FR2924713B1 (fr) | 2010-01-29 |
| RS52001B (en) | 2012-04-30 |
| WO2009103875A1 (fr) | 2009-08-27 |
| BRPI0822066A2 (pt) | 2015-09-22 |
| AU2008351147A1 (en) | 2009-08-27 |
| AU2008351147B2 (en) | 2012-04-12 |
| US8288433B2 (en) | 2012-10-16 |
| SI2231598T1 (sl) | 2011-11-30 |
| GEP20135733B (en) | 2013-01-25 |
| KR20100083195A (ko) | 2010-07-21 |
| NZ586070A (en) | 2012-06-29 |
| JP2011506408A (ja) | 2011-03-03 |
| ES2371699T3 (es) | 2012-01-09 |
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