AR070345A1 - (dihidro ) pirrolo (2,1-a) isoquinolinas - Google Patents
(dihidro ) pirrolo (2,1-a) isoquinolinasInfo
- Publication number
- AR070345A1 AR070345A1 ARP090100410A ARP090100410A AR070345A1 AR 070345 A1 AR070345 A1 AR 070345A1 AR P090100410 A ARP090100410 A AR P090100410A AR P090100410 A ARP090100410 A AR P090100410A AR 070345 A1 AR070345 A1 AR 070345A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- amino
- alkoxy
- halogen
- alkylcarbonyl
- Prior art date
Links
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 20
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical group 0.000 abstract 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 7
- -1 hydroxy, formyl Chemical group 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 3
- 125000006598 aminocarbonylamino group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- LQJLWZPXPQNQQP-UHFFFAOYSA-N 3-acetylpyrrolo[2,1-a]isoquinoline-1-carbonitrile Chemical compound C1=CC=C2C=CN3C(C(=O)C)=CC(C#N)=C3C2=C1 LQJLWZPXPQNQQP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 abstract 1
- 208000035389 Ring chromosome 6 syndrome Diseases 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001540 azides Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 abstract 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 abstract 1
- 125000005553 heteroaryloxy group Chemical group 0.000 abstract 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 abstract 1
- 208000000509 infertility Diseases 0.000 abstract 1
- 230000036512 infertility Effects 0.000 abstract 1
- 231100000535 infertility Toxicity 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/12—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 three hetero rings
- C07D471/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Reproductive Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Los compuestos pueden usarse para el tratamiento de la infertilidad. Reivindicacion 1: Un compuesto caracterizado porque tiene la formula genera (1), o una sal farmacéuticamente aceptable del mismo, donde el enlace C5-C6 puede ser saturado o no saturado; R1 es halogeno, ciano, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-6, cicloalquenilo C5-6, o fenilo o heteroarilo C1-5, estando cada una de dichas especies fenilo y heteroarilo opcionalmente sustituidas independientemente con uno o más sustituyentes seleccionados de R13; R2 es H, ciano, halogeno, alquilo C1-4, alcoxi C1-4-alquilo C1-4, hidroxi C1-4alquilo, formilo, alquilcarbonilo C1-4, C=N-OH o C=N-OCH3; R3 es R15,R16-amino, o R3 es alquilo C1-6, cicloalquilo C3-6, (di)[alquil C1-4]aminoC1 -4alquilo, o R3 es heterocicloalquil C2-6-alquilo C1-4, cuya especie heterocicloalquilo C2-6 puede estar opcionalmente sustituida con alquilcarbonilo C1-4 o cicloalquilcarbonilo C3-6, o R3 es un grupo seleccionado entre las formulas (2); R7 es H, halogeno o metilo; R8 es H, halogeno, alquilo C1-4, alcoxi C1-4, alcoxi C1-4-alquilo C1-4 o hidroxi; R9 es H, formilo, halogeno, hidroxi, amino, ciano, nitro, alquinilo C2-6, cicloalcoxi C3-6, heterocicloalcoxi C2-5, heteroariloxi C2-5, (di)[alquil C1-4]aminocarboxi, alquilcarbonilo C1-6, alcoxicarbonilo C1-4, (di)[alquil C1-4]aminocarbonilo, hetero-cicloalquilcarbonilo C2-6, (di)[alquil C1-4]amino, heterocicloalquilcarbonilamino C2-6, (di)[alquil C1-4]aminocarbonilamino, alcoxicarbonilamino C1-4, (di)[alquil C1-4]aminosulfonil-amino, alquilsulfonilamino C1-4, 1- imidazolidinil-2-ona, 3-oxazolidinil-2-ona o 1-pirrolidinil-2-ona, o R9 es alquilo C1-6, alcoxi C1-6, alquenilo C2-6, alquilcarbonilamino C1-6, heterocicloalquilo C2-6 o heteroarilaminocarbonilo C2-5, estando cada uno de dichos alquilo, alcoxi, alquenilo, heterocicloalquilo y heteroarilo opcionalmente sustituidos independientemente con uno o más sustituyentes seleccionados de R14, o R9 es heteroarilo C1-5, fenilo o fenoxi, todos opcionalmente sustituidos independientemente con uno o más sustituyentes seleccionados de R13; R10 es H, metoxi, halogeno o metilo; R11 es H, alquilo C1-6 o alquenilo C3-4; R12 es alquilcarbonilo C1-4 o cicloalquilcarbonilo C3-6, ambos opcionalmente sustituidos con uno o más sustituyentes seleccionados de R13; R13 es hidroxi, amino, halogeno, nitro, trifluorometilo, ciano, alquilo C1-4, alcoxi C1-4, alquiltio C1-4 o (di)[alquil C1-4]amino; R14 es hidroxi, amino, halogeno, azida, ciano, alquilo C1-4, alcoxi C1-4, alquiltio C1-4, (di)[alquil C1-4]amino, cicloalquilo C3-6, heterocicloalquilo C2-6, alquilcarbonilamino C1-4, (di)[alquil C1-4]aminocarbonilamino, alquilsulfonilamino C1-4, alcoxicarbonilamino C1-4, alquilcarbonilo C1-4, alcoxicarbonilo C1-4, alquilsulfoxi C1-4, heterocicloalcoxi C2-6, (di)[alquil C1-4]aminocarbonilo, alquilsulfonilo C1-4, cicloalquilcarbonilamino C3-6 y [alquil C1-4][alquilcarbonil C1-4]amino; R15 y R16 en R15,R16-amino son seleccionados independientemente entre H o alquilo C1-6, cicloalquilo C3-6, heterocicloalquilo C2-6o (di)[alquil C1-4]amino, todos opcionalmente sustituidos con hidroxi, alquilo C1-4, alcoxi C1-4, alquilcarbonilo C1-4, alcoxicarbonilo C1-4, cicloalquilcarbonilo C3-6, (di)[alquil C1-4]amino, (di)[alquil C1-4]aminocarbonilo o (di)[alcoxi C1-4-alquil C1-4]amino, o R15,R16-amino están unidos en un anillo heterocicloalquilo C3-8, opcionalmente sustituido con R18, o R15,R16-amino están unidos en un anillo heterocicloalquilo C4-8 o un anillo heterocicloalquenilo C4-6, donde ambos contienen un nitrogeno y están opcionalmente sustituidos con uno o más sustituyentes seleccionados de R17; R17 es hidroxi, amino, halogeno, alquilo C1-4, alcoxi C1-4, (di)[alquil C1-4]amino, alquilcarbonilamino C1-4, (di)[alquil C1-4]aminocarbonilamino, alquil-sulfonilamino C1-4, alcoxicarbonilamino C1-4, alquilsulfoxi C1-4, cicloalquilcarbonilamino C3-6, [alquil C1-4][alquilcarbonil C1-4]amino, o R17 es fenilo y heteroarilo C2-5, ambos opcionalmente sustituidos con uno o más sustituyentes seleccionados de R13; y R18 es alquilo C1-4, cicloalquilo C3-6, cicloalquenilcarbonilo C4-6, (di)-[alquil C1-4]aminocarbonilo, alquilsulfonilo C1-4, (di)[alquil C1-4]aminosulfonilo, heterocicloalquilsulfonilo C2-6, heteroarilo C2-5, fenilcarbonilo, alquilcarbonilo C1-4, cicloalquilcarbonilo C3-6, heteroarilcarbonilo C2-5, fenilo, fenilsulfonilo, heteroarilsulfonilo C2-5 y heterocicloalquilcarbonilo C2-6, de los cuales las especies (ciclo)alquilo y (hetero)arilo pueden estar sustituidas con uno o más sustituyentes seleccionados de R13, con la salvedad de que el compuesto no es 3-acetilpirrolo[2,1-a]isoquinolin-1-carbonitrilo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08151199 | 2008-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR070345A1 true AR070345A1 (es) | 2010-03-31 |
Family
ID=39516937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090100410A AR070345A1 (es) | 2008-02-08 | 2009-02-06 | (dihidro ) pirrolo (2,1-a) isoquinolinas |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US8394789B2 (es) |
| EP (1) | EP2252611B1 (es) |
| JP (1) | JP5620823B2 (es) |
| KR (1) | KR101586870B1 (es) |
| CN (1) | CN102216297B (es) |
| AR (1) | AR070345A1 (es) |
| AT (1) | ATE527260T1 (es) |
| AU (1) | AU2009211296B2 (es) |
| BR (1) | BRPI0906937A2 (es) |
| CA (1) | CA2713173C (es) |
| CL (1) | CL2009000281A1 (es) |
| CO (1) | CO6241120A2 (es) |
| DK (1) | DK2252611T3 (es) |
| EC (1) | ECSP10010303A (es) |
| ES (1) | ES2373022T3 (es) |
| HR (1) | HRP20110942T1 (es) |
| IL (1) | IL206378A0 (es) |
| MX (1) | MX2010008717A (es) |
| NZ (1) | NZ587164A (es) |
| PE (1) | PE20091413A1 (es) |
| PL (1) | PL2252611T3 (es) |
| PT (1) | PT2252611E (es) |
| RU (1) | RU2495037C2 (es) |
| SI (1) | SI2252611T1 (es) |
| TW (1) | TW200944523A (es) |
| WO (1) | WO2009098283A1 (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8071587B2 (en) * | 2009-05-27 | 2011-12-06 | N. V. Organon | (Dihydro)imidazoiso[5,1-A]quinolines |
| TWI461426B (zh) * | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| US20120258957A1 (en) | 2009-11-23 | 2012-10-11 | Matilda Jane Bingham | Heterocyclic derivatives |
| US20120174381A1 (en) | 2011-01-10 | 2012-07-12 | David Messick | Apparatus and method for frame crimping |
| WO2012112958A2 (en) * | 2011-02-19 | 2012-08-23 | The Broad Institute, Inc | High-throughput assays to probe leukemia within the stromal niche |
| EP2763986B1 (en) * | 2011-09-22 | 2017-06-07 | Merck Sharp & Dohme B.V. | Fsh receptor antagonists |
| EP2796460B1 (en) * | 2011-12-21 | 2018-07-04 | Jiangsu Hengrui Medicine Co. Ltd. | Pyrrole six-membered heteroaryl ring derivative, preparation method therefor, and medicinal uses thereof |
| CN102718695B (zh) * | 2012-06-25 | 2014-04-02 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| CA2892042C (en) | 2012-11-29 | 2022-06-14 | Chemocentryx, Inc. | Cxcr7 antagonists |
| RU2550366C1 (ru) * | 2014-05-22 | 2015-05-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Российский университет дружбы народов" (РУДН) | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 5,6-ДИГИДРОПИРРОЛО[2,1-a]ИЗОХИНОЛИНОВ |
| EP3893882A4 (en) * | 2018-12-12 | 2022-08-31 | ChemoCentryx, Inc. | CXCR7 INHIBITORS FOR THE TREATMENT OF CANCER |
| CN110540519B (zh) * | 2019-09-05 | 2022-12-02 | 宁波大学 | 一种1,6-烯炔类化合物与酮类化合物的自由基环化反应方法 |
| CN113999103A (zh) * | 2021-11-26 | 2022-02-01 | 八叶草健康产业研究院(厦门)有限公司 | 一种α-羟基-环丁烷甲酸的制备方法 |
| AU2024231935A1 (en) | 2023-03-08 | 2025-07-17 | Ferring B.V. | Small molecule fsh receptor modulators |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8718980D0 (en) * | 1987-08-11 | 1987-09-16 | May & Baker Ltd | Compositions of matter |
| DE4343649A1 (de) * | 1993-12-21 | 1995-06-22 | Boehringer Ingelheim Kg | Neue Pyridazino[4',5':3,4]pyrrolo-[2,1-a]isochinoline und deren Verwendung für die Herstellung von pharmazeutischen Zubereitungen |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE69931975T2 (de) * | 1998-08-07 | 2006-10-05 | Applied Research Systems Ars Holding N.V. | FSH Mimetika zur Behandlung von Infertilität |
| WO2000048144A1 (fr) | 1999-02-15 | 2000-08-17 | Medailles Souvenirs | Dispositif de personnalisation et de distribution de medailles |
| AU2001278006A1 (en) | 2000-07-27 | 2002-02-13 | Smithkline Beecham Corporation | Agonists of follicle stimulating hormone activity |
| CA2431326A1 (en) * | 2000-12-13 | 2002-06-20 | Bayer Aktiengesellschaft | Pyrrolo (2.1-a) dihydroisoquinolines and their use as phosphodiesterase 10a inhibitors |
| HRP20031080A2 (en) | 2001-07-02 | 2004-04-30 | Akzo Nobel Nv | Tetrahydroquinoline derivatives |
| WO2003014115A1 (en) | 2001-08-06 | 2003-02-20 | Bayer Aktiengesellschaft | 3-substituted pyrrolo (2.1-a) isoquinoline derivatives |
| WO2003014116A1 (en) | 2001-08-06 | 2003-02-20 | Bayer Corporation | Pyrrolo[2.1-a]isoquinoline derivatives |
| WO2003051877A1 (en) * | 2001-12-18 | 2003-06-26 | Bayer Corporation | 2-substituted pyrrolo[2.1-a]isoquinolines against cancer |
| EP1542993B1 (en) | 2002-09-20 | 2012-12-19 | Merck Serono SA | Piperazine derivatives and methods of use |
| CN1809565A (zh) | 2003-06-30 | 2006-07-26 | 奥坦纳医药公司 | 用于治疗癌症的吡咯并二氢异喹啉 |
| US20070105840A1 (en) | 2003-06-30 | 2007-05-10 | Altana Pharma Ag | Pyrrolo-dihydroisoquinoline derivatives as pde10 inhibitors |
| WO2005087765A1 (en) | 2004-03-04 | 2005-09-22 | Arena Pharmaceuticals, Inc. | Ligands of follicle stimulating hormone receptor and methods of use thereof |
| AU2006218054A1 (en) | 2005-01-12 | 2006-08-31 | Nycomed Gmbh | Novel pyrrolodihydroisoquinolines as PDE10 inhibitors |
| US20080064714A1 (en) | 2005-01-12 | 2008-03-13 | Nycomed Gmbh | Novel Pyrrolodihydroisoquinolines |
| ES2361674T3 (es) | 2005-05-04 | 2011-06-21 | N.V. Organon | Derivados de dihidropiridina. |
| UA92007C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодности |
| UA92008C2 (en) | 2005-05-04 | 2010-09-27 | Н.В. Органон | 4-PHENYL-5-OXO-l,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES AS MEDICAMENTS FOR THE TREATMENT OF INFERTILITY |
| UA92009C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодия |
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2009
- 2009-01-19 TW TW098101900A patent/TW200944523A/zh unknown
- 2009-02-05 PE PE2009000177A patent/PE20091413A1/es not_active Application Discontinuation
- 2009-02-06 AT AT09708584T patent/ATE527260T1/de active
- 2009-02-06 SI SI200930133T patent/SI2252611T1/sl unknown
- 2009-02-06 CL CL2009000281A patent/CL2009000281A1/es unknown
- 2009-02-06 US US12/866,468 patent/US8394789B2/en active Active
- 2009-02-06 WO PCT/EP2009/051366 patent/WO2009098283A1/en not_active Ceased
- 2009-02-06 CN CN200980103881.7A patent/CN102216297B/zh not_active Expired - Fee Related
- 2009-02-06 NZ NZ587164A patent/NZ587164A/en not_active IP Right Cessation
- 2009-02-06 PT PT09708584T patent/PT2252611E/pt unknown
- 2009-02-06 KR KR1020107020092A patent/KR101586870B1/ko not_active Expired - Fee Related
- 2009-02-06 CA CA2713173A patent/CA2713173C/en not_active Expired - Fee Related
- 2009-02-06 MX MX2010008717A patent/MX2010008717A/es active IP Right Grant
- 2009-02-06 PL PL09708584T patent/PL2252611T3/pl unknown
- 2009-02-06 HR HR20110942T patent/HRP20110942T1/hr unknown
- 2009-02-06 JP JP2010545476A patent/JP5620823B2/ja not_active Expired - Fee Related
- 2009-02-06 DK DK09708584.9T patent/DK2252611T3/da active
- 2009-02-06 RU RU2010136057/04A patent/RU2495037C2/ru not_active IP Right Cessation
- 2009-02-06 AU AU2009211296A patent/AU2009211296B2/en not_active Ceased
- 2009-02-06 ES ES09708584T patent/ES2373022T3/es active Active
- 2009-02-06 BR BRPI0906937A patent/BRPI0906937A2/pt not_active IP Right Cessation
- 2009-02-06 AR ARP090100410A patent/AR070345A1/es unknown
- 2009-02-06 EP EP09708584A patent/EP2252611B1/en active Active
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2010
- 2010-06-15 IL IL206378A patent/IL206378A0/en unknown
- 2010-06-23 EC EC2010010303A patent/ECSP10010303A/es unknown
- 2010-08-06 CO CO10096219A patent/CO6241120A2/es not_active Application Discontinuation
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