HRP20120517T1 - Postupak priprave derivata halobifenil ilciklopropanekarboksilne kiseline - Google Patents
Postupak priprave derivata halobifenil ilciklopropanekarboksilne kiseline Download PDFInfo
- Publication number
- HRP20120517T1 HRP20120517T1 HRP20120517AT HRP20120517T HRP20120517T1 HR P20120517 T1 HRP20120517 T1 HR P20120517T1 HR P20120517A T HRP20120517A T HR P20120517AT HR P20120517 T HRP20120517 T HR P20120517T HR P20120517 T1 HRP20120517 T1 HR P20120517T1
- Authority
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- Croatia
- Prior art keywords
- compound
- formula
- fluoro
- dichloro
- biphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 13
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 10
- 238000006243 chemical reaction Methods 0.000 claims 6
- 229910052763 palladium Inorganic materials 0.000 claims 5
- VXARNRWZIXSZQV-UHFFFAOYSA-N 1,2-dichloro-4-(2-fluoro-4-methylphenyl)benzene Chemical group FC1=CC(C)=CC=C1C1=CC=C(Cl)C(Cl)=C1 VXARNRWZIXSZQV-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims 2
- VIAGWCCTVXKMIP-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carbonitrile Chemical compound FC1=CC(C2(CC2)C#N)=CC=C1C1=CC=C(Cl)C(Cl)=C1 VIAGWCCTVXKMIP-UHFFFAOYSA-N 0.000 claims 2
- LIYLTQQDABRNRX-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(F)=CC=1C1(C(=O)O)CC1 LIYLTQQDABRNRX-UHFFFAOYSA-N 0.000 claims 2
- CWCQHXOAFSQEDX-UHFFFAOYSA-N 2-[4-(3,4-dichlorophenyl)-3-fluorophenyl]acetonitrile Chemical group FC1=CC(CC#N)=CC=C1C1=CC=C(Cl)C(Cl)=C1 CWCQHXOAFSQEDX-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- 230000031709 bromination Effects 0.000 claims 2
- 238000005893 bromination reaction Methods 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- JKIGHOARKAIPJI-UHFFFAOYSA-N (3,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(Cl)=C1 JKIGHOARKAIPJI-UHFFFAOYSA-N 0.000 claims 1
- SLFNGVGRINFJLK-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methylbenzene Chemical compound CC1=CC=C(Br)C(F)=C1 SLFNGVGRINFJLK-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000004342 Benzoyl peroxide Substances 0.000 claims 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 235000019400 benzoyl peroxide Nutrition 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Toxicology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Postupak priprave spoja opće formule I I u kojojX jest fluor tepredstavlja jedan ili više atoma halogena naznačen time da rečeni postupak obuhvaća sljedeće korake i reakcija spoja formule II II u kojoj je X gore definiran a X je odabran iz sljedeće skupine klor brom jod te triflatna skupina CF SO sa spojem formule III III u kojoj je R kao što je gore definiran i nastaje spoj formule IV IV ii podvrgavanje spoja formule IV radikalskom bromiranju pri čemu nastaje spoj formule V V iii pretvorba spojaformule V u odgovarajući nitrilni derivat spojaformule VI VI iv reakcija spoja formule VI sa dibrometanom čime nastaje spoj formuleVII te VI hidroliza spoja formule VII pri čemu nastaje spoj formule I Patent sadrži još patentnih zahtjeva
Claims (10)
1. Postupak priprave spoja opće formule (I)
[image]
(I)
u kojoj
X jest fluor, te
predstavlja jedan ili više atoma halogena,
naznačen time da rečeni postupak obuhvaća sljedeće korake:
(i) reakcija spoja formule (II),
[image]
(II)
u kojoj je X gore definiran, a X' je odabran iz sljedeće skupine: klor, brom, jod te triflatna skupina (CF3SO3), sa spojem formule (III)
[image]
(III)
u kojoj je R kao što je gore definiran i nastaje spoj formule (IV),
[image]
(IV)
(ii) podvrgavanje spoja formule (IV) radikalskom bromiranju pri čemu nastaje spoj formule (V);
[image]
(V)
(iii) pretvorba spoja formule (V) u odgovarajući nitrilni derivat spoja formule (VI),
[image]
(VI)
(iv) reakcija spoja formule (VI) sa 1,2-dibrometanom čime nastaje spoj formule (VII), te
[image]
(VI)
(v) hidroliza spoja formule (VII) pri čemu nastaje spoj formule (I).
2. Postupak kako je prijavljen u patentnom zahtjevu 1, naznačen time da nadalje obuhvaća korake izolacije i kristalizacije spoja formule (I).
3. Postupak prema patentnom zahtjevu 2, naznačen time da se kristalizacija izvodi korištenjem smjese n-heptana i izopropanola.
4. Postupak kako je prijavljen u patentnim zahtjevima 1 do 3, naznačen time da se korak (i) provodi u prisutnosti paladija kao katalizatora odabranog od sljedećih: tetrakis(trifenilfosfin)paladj, paladij na aktivnom ugljenu ili paladij na aluminijevom oksidu.
5. Postupak kako je prijavljen u patentnom zahtjevu 4, naznačen time da paladij kao katalizator jest paladij na aktivnom ugljenu.
6. Postupak kako je prijavljen u bilo kojem od prethodnih patentnih zahtjeva, naznačen time da se korak (ii) provodi s N-bromsukcinimidom u prisutnosti katalitičke količine benzoil-peroksida u acetonitrilu kao otapalu.
7. Postupak kako je prijavljen u patentnom zahtjevu 1, naznačen time da halogen jest atom klora.
8. Postupak kako je prijavljen u patentnom zahtjevu 7, naznačen time da spoj formule (I) jest 1-(3’,4’-diklor-2-fluor[1,1’-bifenil]-4-il)-ciklopropankarboksilna kiselina.
9. Postupak kako je prijavljen u patentnom zahtjevu 8, naznačen time da obuhvaća sljedeće korake:
(i) reakcija 4-brom-3-fluor-toluena sa 3,4-diklorfenilbornom kiseliom kojom nastaje 3’,4’-diklor-2-fluor-4-metil-bifenil,
(ii) podvrgavanje 3’,4’-diklor-2-fluor-4-metil-bifenila radikalskom bromiranju pri čemu nastaje 3’,4’-diklor-2-fluor-4-metil-bifenil,
(iii) pretvorba 3’,4’-diklor-2-fluor-4-metil-bifenila u odgovarajući 3’,4’-diklor-2-fluor-4-cijanometil-bifenil,
(iv) reakcija 3’,4’-diklor-2-fluor-4-cijanometil-bifenila sa 1,2-dibrometanom pri čemu nastaje 1-(3’,4'-diklor-2-fluor[1,1’-bifenil]-4-il)-ciklopropanonitril, te
(v) hidrolizia 1-(3’,4'-diklor-2-fluor[1,1’-bifenil]-4-il)-ciklopropanonitrila pri čemu nastaje 1-(3’,4’-diklor-2-fluor[1,1’-bifenil]-4-il)-ciklopropankarboksilna kiselina.
10. Postupak priprave farmaceutskog pripravka koji obuhvaća korake (i)-(v) iz patentnog zahtjeva 1, naznačen time da je dodatni korak (iv) obuhvaća smjesu s jednim ili više farmaceutski prihvatljivim ekscipijensima.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08158022A EP2133322A1 (en) | 2008-06-11 | 2008-06-11 | Process of preparing derivatives of 1-(2-halobiphenyl-4-yl)-cyclopropanecarboxylic acid |
| PCT/EP2009/003288 WO2009149797A1 (en) | 2008-06-11 | 2009-05-08 | Process of preparing derivatives of 1-(2-halobiphenyl-4-yl)-cyclopropanecarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120517T1 true HRP20120517T1 (hr) | 2012-07-31 |
Family
ID=40120119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120517AT HRP20120517T1 (hr) | 2008-06-11 | 2012-06-20 | Postupak priprave derivata halobifenil ilciklopropanekarboksilne kiseline |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US8076505B2 (hr) |
| EP (2) | EP2133322A1 (hr) |
| JP (1) | JP5642067B2 (hr) |
| KR (1) | KR101257217B1 (hr) |
| CN (1) | CN102046576B (hr) |
| AT (1) | ATE552230T1 (hr) |
| AU (1) | AU2009256959B2 (hr) |
| BR (1) | BRPI0909560A2 (hr) |
| CA (1) | CA2723878C (hr) |
| CO (1) | CO6331461A2 (hr) |
| DK (1) | DK2285765T3 (hr) |
| ES (1) | ES2384368T3 (hr) |
| GE (1) | GEP20135800B (hr) |
| HK (1) | HK1152292A1 (hr) |
| HR (1) | HRP20120517T1 (hr) |
| IL (1) | IL209209A (hr) |
| MA (1) | MA32297B1 (hr) |
| ME (1) | ME01160B (hr) |
| MX (1) | MX2010012285A (hr) |
| MY (1) | MY150280A (hr) |
| NZ (1) | NZ589087A (hr) |
| PL (1) | PL2285765T3 (hr) |
| PT (1) | PT2285765E (hr) |
| RU (1) | RU2502721C2 (hr) |
| SI (1) | SI2285765T1 (hr) |
| UA (1) | UA101835C2 (hr) |
| WO (1) | WO2009149797A1 (hr) |
| ZA (1) | ZA201007977B (hr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101088272B1 (ko) * | 2003-02-21 | 2011-11-30 | 키에시 파르마슈티시 엣스. 피. 에이. | 신경 퇴행성 질환의 치료를 위한 1-페닐알캔카복실산추출물 |
| PT2462098E (pt) * | 2009-08-04 | 2013-12-04 | Chiesi Farma Spa | Processos para a preparação de derivados de ácido 1-(2- halobifenil-4-il)-ciclopropanocarboxílico |
| CN106431900A (zh) | 2010-04-01 | 2017-02-22 | 奇斯药制品公司 | 新的多晶型物和盐 |
| ES2526522T3 (es) * | 2010-04-21 | 2015-01-13 | Chiesi Farmaceutici S.P.A. | Derivados del ácido 1-(2-fluorobifenil-4-il)alquil carboxílico para la terapia de la amiloidosis transtiretina |
| CA2801449A1 (en) | 2010-06-04 | 2011-12-08 | Chiesi Farmaceutici S.P.A. | 1-(2-fluorobiphenyl-4-yl)-cyclopropanecarboxylic acid derivatives for the therapy of prion diseases |
| US9592210B2 (en) | 2011-12-22 | 2017-03-14 | Chiesi Farmaceutici S.P.A. | 1-phenylalkanecarboxylic acid derivatives for the treatment of cognitive impairment |
| CA2869418A1 (en) | 2012-04-04 | 2013-10-10 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-(2-halo-biphenyl-4-yl)- alkanecarboxylic acids for the treatment of neurodegenerative diseases |
| EP2818460A1 (en) | 2013-06-24 | 2014-12-31 | ZaCh System S.p.A. | Cyclopropanation of substituted phenylacetonitriles or phenyl acetates |
| RU2015153818A (ru) | 2013-06-24 | 2017-06-21 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Усовершенствованный способ получения производных 1-(2-фтор[1, 1-бифенил]-4-ил)-циклопропанкарбоновой кислоты |
| US20150335596A1 (en) | 2014-05-26 | 2015-11-26 | Chiesi Farmaceutici S.P.A. | 1-(2-fluorobiphenyl-4-yl)-cyclopropanecarboxylic acid derivatives for the treatment of down's syndrome |
| CN107698462A (zh) * | 2017-10-10 | 2018-02-16 | 重庆科脉生物化工有限公司 | 一种1‑氨基‑1‑环丙腈盐酸盐的制备方法 |
| AU2022338032A1 (en) | 2021-08-31 | 2024-03-07 | Cerespir Incorporated | Co-crystals |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4507294B2 (ja) * | 1999-05-27 | 2010-07-21 | チッソ株式会社 | ビアリール誘導体の製造方法 |
| JP4502293B2 (ja) * | 1999-06-04 | 2010-07-14 | 長瀬産業株式会社 | 軸不斉を有する光学活性な４級アンモニウム塩、その製法およびα−アミノ酸誘導体の不斉合成への応用 |
| JP2004091342A (ja) * | 2002-08-29 | 2004-03-25 | Matsushita Electric Ind Co Ltd | 芳香族メチリデン化合物、それを製造するための化合物、それらの製造方法、及び芳香族メチリデン化合物を用いた有機電界発光素子 |
| ITMI20030311A1 (it) * | 2003-02-21 | 2004-08-22 | Chiesi Farma Spa | Acidi 2-fenil-2-dialchil-acetici per il trattamento della malattia di alzheimer. |
| KR101088272B1 (ko) | 2003-02-21 | 2011-11-30 | 키에시 파르마슈티시 엣스. 피. 에이. | 신경 퇴행성 질환의 치료를 위한 1-페닐알캔카복실산추출물 |
| EP1650183A1 (en) * | 2004-10-21 | 2006-04-26 | Cellzome Ag | (Benzyloxy-biphenyl) acetic acids and derivatives thereof and their use in therapy |
| US7524870B2 (en) * | 2004-12-03 | 2009-04-28 | Hoffmann-La Roche Inc. | Biaryloxymethylarenecarboxylic acids as glycogen synthase activators |
| JP2008546651A (ja) * | 2005-06-14 | 2008-12-25 | メルク フロスト カナダ リミテツド | モノアミンオキシダーゼａ及びｂの可逆的阻害剤 |
| JP5272345B2 (ja) * | 2006-08-28 | 2013-08-28 | 東ソー株式会社 | ヘテロアセン誘導体、テトラハロターフェニル誘導体及びそれらの製造方法 |
| PT2462098E (pt) * | 2009-08-04 | 2013-12-04 | Chiesi Farma Spa | Processos para a preparação de derivados de ácido 1-(2- halobifenil-4-il)-ciclopropanocarboxílico |
-
2008
- 2008-06-11 EP EP08158022A patent/EP2133322A1/en not_active Withdrawn
-
2009
- 2009-05-08 PL PL09761360T patent/PL2285765T3/pl unknown
- 2009-05-08 RU RU2010146299/04A patent/RU2502721C2/ru not_active IP Right Cessation
- 2009-05-08 CN CN2009801196647A patent/CN102046576B/zh not_active Expired - Fee Related
- 2009-05-08 SI SI200930272T patent/SI2285765T1/sl unknown
- 2009-05-08 UA UAA201013287A patent/UA101835C2/uk unknown
- 2009-05-08 PT PT09761360T patent/PT2285765E/pt unknown
- 2009-05-08 MX MX2010012285A patent/MX2010012285A/es active IP Right Grant
- 2009-05-08 GE GEAP200911997A patent/GEP20135800B/en unknown
- 2009-05-08 DK DK09761360.8T patent/DK2285765T3/da active
- 2009-05-08 AU AU2009256959A patent/AU2009256959B2/en not_active Ceased
- 2009-05-08 KR KR1020107027903A patent/KR101257217B1/ko not_active IP Right Cessation
- 2009-05-08 ES ES09761360T patent/ES2384368T3/es active Active
- 2009-05-08 CA CA2723878A patent/CA2723878C/en active Active
- 2009-05-08 NZ NZ589087A patent/NZ589087A/en not_active IP Right Cessation
- 2009-05-08 MY MYPI2010005220A patent/MY150280A/en unknown
- 2009-05-08 AT AT09761360T patent/ATE552230T1/de active
- 2009-05-08 BR BRPI0909560A patent/BRPI0909560A2/pt not_active IP Right Cessation
- 2009-05-08 WO PCT/EP2009/003288 patent/WO2009149797A1/en active Application Filing
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