JP2010519265A5 - - Google Patents
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- Publication number
- JP2010519265A5 JP2010519265A5 JP2009550672A JP2009550672A JP2010519265A5 JP 2010519265 A5 JP2010519265 A5 JP 2010519265A5 JP 2009550672 A JP2009550672 A JP 2009550672A JP 2009550672 A JP2009550672 A JP 2009550672A JP 2010519265 A5 JP2010519265 A5 JP 2010519265A5
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- mono
- acid
- cyclohexane
- indole
- 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.)
- Granted
Links
- 229920006395 saturated elastomer Polymers 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- NKOQRTYLFHGXEJ-UHFFFAOYSA-N 1'-phenyl-1'-pyrrolidin-1-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane] Chemical compound C1CCCN1C1(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)CC1 NKOQRTYLFHGXEJ-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- LMUNPDLJHOMEAL-UHFFFAOYSA-N 1'-(azetidin-1-yl)-1'-(3-fluorophenyl)spiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane] Chemical compound FC1=CC=CC(C2(CCC3(CC2)C2=C(C4=CC=CC=C4N2)CCN3)N2CCC2)=C1 LMUNPDLJHOMEAL-UHFFFAOYSA-N 0.000 claims 2
- ALUNJDZLXQIJPO-UHFFFAOYSA-N 1'-(azetidin-1-yl)-6-fluoro-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane] Chemical compound C12=CC(F)=CC=C2NC2=C1CCOC2(CC1)CCC1(C=1C=CC=CC=1)N1CCC1 ALUNJDZLXQIJPO-UHFFFAOYSA-N 0.000 claims 2
- YGWYFBNPSRSUSZ-UHFFFAOYSA-N 1'-(azetidin-1-yl)-6-fluoro-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane];2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C12=CC(F)=CC=C2NC2=C1CCOC2(CC1)CCC1(C=1SC=CC=1)N1CCC1 YGWYFBNPSRSUSZ-UHFFFAOYSA-N 0.000 claims 2
- VTBQKIVRFSODAM-UHFFFAOYSA-N 1'-butyl-6-fluoro-1'-pyrrolidin-1-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane] Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CCC1(CCCC)N1CCCC1 VTBQKIVRFSODAM-UHFFFAOYSA-N 0.000 claims 2
- CEHSUFYIKKLVCO-UHFFFAOYSA-N 6-fluoro-1'-phenyl-1'-pyrrolidin-1-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane] Chemical compound C12=CC(F)=CC=C2NC2=C1CCOC2(CC1)CCC1(C=1C=CC=CC=1)N1CCCC1 CEHSUFYIKKLVCO-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims 1
- GHLNZJNTCTXKGD-UHFFFAOYSA-N 1'-(azetidin-1-yl)-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane] Chemical compound FC1=CC=CC(C2(CCC3(CC2)C2=C(C4=CC=CC=C4N2)CCO3)N2CCC2)=C1 GHLNZJNTCTXKGD-UHFFFAOYSA-N 0.000 claims 1
- OEWXCXVBBXJSIX-UHFFFAOYSA-N 1'-benzyl-6-fluorospiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CCC1(N)CC1=CC=CC=C1 OEWXCXVBBXJSIX-UHFFFAOYSA-N 0.000 claims 1
- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 claims 1
- QACHHWDJMFBSJR-UHFFFAOYSA-N 1-[1'-(azetidin-1-yl)-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,4'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1=CC=CC(C2(CCC3(CC2)C2=C(C4=CC=CC=C4N2)CCN3C(=O)C=CC=2C=CC=CC=2)N2CCC2)=C1 QACHHWDJMFBSJR-UHFFFAOYSA-N 0.000 claims 1
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 claims 1
- VIKBNMWOLLIQPG-UHFFFAOYSA-N 2-methyldecanedioic acid Chemical compound OC(=O)C(C)CCCCCCCC(O)=O VIKBNMWOLLIQPG-UHFFFAOYSA-N 0.000 claims 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 claims 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 235000019136 lipoic acid Nutrition 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960003512 nicotinic acid Drugs 0.000 claims 1
- 235000001968 nicotinic acid Nutrition 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 229960002663 thioctic acid Drugs 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007009319A DE102007009319A1 (de) | 2007-02-22 | 2007-02-22 | Spirocyclische Cyclohexan-Derivate |
| DE102007009319.7 | 2007-02-22 | ||
| PCT/EP2008/001271 WO2008101660A1 (de) | 2007-02-22 | 2008-02-19 | Spirocyclische cyclohexan-derivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010519265A JP2010519265A (ja) | 2010-06-03 |
| JP2010519265A5 true JP2010519265A5 (https=) | 2014-03-20 |
| JP5514556B2 JP5514556B2 (ja) | 2014-06-04 |
Family
ID=39531427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009550672A Expired - Fee Related JP5514556B2 (ja) | 2007-02-22 | 2008-02-19 | スピロ環式シクロヘキサン誘導体 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7960404B2 (https=) |
| EP (1) | EP2121691B1 (https=) |
| JP (1) | JP5514556B2 (https=) |
| KR (1) | KR101517748B1 (https=) |
| CN (1) | CN101622256B (https=) |
| AT (1) | ATE554089T1 (https=) |
| AU (1) | AU2008217277B2 (https=) |
| BR (1) | BRPI0806794A2 (https=) |
| CA (1) | CA2679173C (https=) |
| CO (1) | CO6220948A2 (https=) |
| CY (1) | CY1112725T1 (https=) |
| DE (1) | DE102007009319A1 (https=) |
| DK (1) | DK2121691T3 (https=) |
| EC (1) | ECSP099621A (https=) |
| ES (1) | ES2386387T3 (https=) |
| HR (1) | HRP20120511T1 (https=) |
| IL (1) | IL200496A (https=) |
| MX (1) | MX2009007387A (https=) |
| NZ (1) | NZ578589A (https=) |
| PL (1) | PL2121691T3 (https=) |
| PT (1) | PT2121691E (https=) |
| RU (1) | RU2470933C2 (https=) |
| SI (1) | SI2121691T1 (https=) |
| WO (1) | WO2008101660A1 (https=) |
| ZA (1) | ZA200906584B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006033114A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| CA2719735A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| JP5599774B2 (ja) | 2008-03-27 | 2014-10-01 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ヒドロキシメチルシクロヘキシルアミン類 |
| WO2009118174A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
| ATE537143T1 (de) | 2008-03-27 | 2011-12-15 | Gruenenthal Gmbh | Spiro(5.5)undecan derivate |
| PT2260042E (pt) | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
| US9073925B2 (en) | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003007A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| US8618299B2 (en) | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| EP2649044B1 (en) | 2010-12-08 | 2017-09-20 | Grünenthal GmbH | Method for synthesising substituted aminocyclohexanone derivatives |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| CN104159902B (zh) * | 2011-12-12 | 2016-05-04 | 格吕伦塔尔有限公司 | 制备(1r,4r)-6’-氟-(N,N-二甲基-和N-甲基)-4-苯基-4’,9’-二氢-3’H-螺[环己烷-1,1’-吡喃并[3,4,b]吲哚]-4-胺的方法 |
| BR112015022509A2 (pt) | 2013-03-15 | 2017-07-18 | Gruenenthal Gmbh | forma cristalina de cis-(e)-4-(3-fluorofenil)-2',3',4',9'-tetra-hidro-n,n-dimetil-2'-(1-oxo-3-fenil-2-propenil)-espiro[ciclohexano-1,1'[1h]-pirido[3,4-b]indol]-4-amina cristalina |
| HUE040133T2 (hu) | 2014-07-15 | 2019-02-28 | Gruenenthal Gmbh | Szubsztituált azaspiro(4.5)dekán származékok |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| JP6673924B2 (ja) * | 2015-01-23 | 2020-03-25 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 肝機能障害および／または腎機能障害を有する対象における疼痛を治療するためのセブラノパドール |
| CN107383027A (zh) * | 2017-07-24 | 2017-11-24 | 扬州大学 | 一种四氢螺类化合物的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2265018C2 (ru) * | 2001-04-18 | 2005-11-27 | Эро-Селтик, С.А. | Производные бензимидазола и фармацевтические композиции на их основе |
| DE10252667A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360792A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006046745A1 (de) | 2006-09-29 | 2008-04-03 | Grünenthal GmbH | Gemischte ORL1/µ-Agonisten zur Behandlung von Schmerz |
-
2007
- 2007-02-22 DE DE102007009319A patent/DE102007009319A1/de not_active Withdrawn
-
2008
- 2008-02-19 ES ES08715856T patent/ES2386387T3/es active Active
- 2008-02-19 CA CA2679173A patent/CA2679173C/en not_active Expired - Fee Related
- 2008-02-19 AU AU2008217277A patent/AU2008217277B2/en not_active Ceased
- 2008-02-19 RU RU2009135070/04A patent/RU2470933C2/ru not_active IP Right Cessation
- 2008-02-19 PT PT08715856T patent/PT2121691E/pt unknown
- 2008-02-19 NZ NZ578589A patent/NZ578589A/en not_active IP Right Cessation
- 2008-02-19 CN CN200880006055.6A patent/CN101622256B/zh not_active Expired - Fee Related
- 2008-02-19 EP EP08715856A patent/EP2121691B1/de not_active Not-in-force
- 2008-02-19 DK DK08715856.4T patent/DK2121691T3/da active
- 2008-02-19 BR BRPI0806794-5A patent/BRPI0806794A2/pt not_active IP Right Cessation
- 2008-02-19 KR KR1020097019738A patent/KR101517748B1/ko not_active Expired - Fee Related
- 2008-02-19 AT AT08715856T patent/ATE554089T1/de active
- 2008-02-19 HR HRP20120511AT patent/HRP20120511T1/hr unknown
- 2008-02-19 WO PCT/EP2008/001271 patent/WO2008101660A1/de not_active Ceased
- 2008-02-19 JP JP2009550672A patent/JP5514556B2/ja not_active Expired - Fee Related
- 2008-02-19 PL PL08715856T patent/PL2121691T3/pl unknown
- 2008-02-19 SI SI200830635T patent/SI2121691T1/sl unknown
- 2008-02-19 MX MX2009007387A patent/MX2009007387A/es active IP Right Grant
-
2009
- 2009-08-19 CO CO09086728A patent/CO6220948A2/es active IP Right Grant
- 2009-08-20 IL IL200496A patent/IL200496A/en active IP Right Grant
- 2009-08-21 US US12/545,261 patent/US7960404B2/en not_active Expired - Fee Related
- 2009-09-09 EC EC2009009621A patent/ECSP099621A/es unknown
- 2009-09-21 ZA ZA200906584A patent/ZA200906584B/xx unknown
-
2012
- 2012-05-11 CY CY20121100445T patent/CY1112725T1/el unknown
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