TWI299041B - Bi-and tricyclic substituted phenyl methanones - Google Patents
Bi-and tricyclic substituted phenyl methanones Download PDFInfo
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- TWI299041B TWI299041B TW094143890A TW94143890A TWI299041B TW I299041 B TWI299041 B TW I299041B TW 094143890 A TW094143890 A TW 094143890A TW 94143890 A TW94143890 A TW 94143890A TW I299041 B TWI299041 B TW I299041B
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- Prior art keywords
- compound
- alkyl
- formula
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- dihydro
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical class O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 31
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- -1 2-isopropoxy-5-methanesulfonyl-phenyl Chemical group 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- QGIGNHJWEORARI-UHFFFAOYSA-N 1-(2-methylpropoxy)-4-methylsulfonylbenzene Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1 QGIGNHJWEORARI-UHFFFAOYSA-N 0.000 description 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1299041 R，為C「C7烷基、經鹵素取代之CVC7烷基或為_(CH2)n. ^ 環烷基； R” 為(^-(：7烷基； R2 為 N〇2、CN或 S02R"; r5/r6為氫、齒素、C丨-C7烷基、C丨-C：7烷氧基、或為經齒 素取代之C〗-C7貌基或Ci-C7院氧基； R7 為氫或CrC?烷基； η 為0、1或2 ; # 及醫藥活性酸加成鹽。 5_如請求項1之化合物，其具有式id，
其中： • Rl為包含一或兩個選自由〇、N或S組成之群之雜原子 的五員或六員雜環，或為OR，或N(R")2 ; R|為心-匸7烷基、經鹵素取代之Ci_C7烷基或為-⑴仏^ 環烷基； R" 為Ci-C7烷基； R2 為 N〇2、CN或 S〇2r"; r5/r6為氫、自素、Cl_C7烷基、c〗_c7烷氧基、或為經鹵 素取代之Cl_C7烷基或Ci-C?烷氧基； 106827-971127.doc -4- 斗丄 η 為〇、1或2 ; 及醫藥活性酸加成鹽。 如明求項1之化合物’其具有式ΙΕ
其中： R 為包含一或兩個選自由〇、N或S組成之群之雜原子 的五員或六員雜環，或為OR，或N(R")2 ; R 為Cl-C7烷基、經鹵素取代2C,-C7烷基或為·（(：Η2)η_ 環烷基； R"為<^-(：7烷基； r2 為 N〇2、cn或 so2r"; r6為氫、鹵素、Ci-C7烷基、C丨-C：7烷氧基、或為經鹵素 取代之CrC?烷基或(^-(：7烷氧基； η 為〇、1或2 ; 及醫藥活性酸加成鹽。 7.如請求項1之化合物，其具有式IF， 106827-971127.doc 1299041
其中： R1為包含一或雨個選自由Ο、N或S組成之群之雜原子 的五員或六員雜環，或為or·或N(R")2 ;
R 為C1-C7烧基經_素取代之C1-C7烧基或為 環烧基； R" 為匕-仏烷基； R2 為 N〇2、CN或 S〇2R"; R5/R6為氫、鹵素、C丨_C7烷基、CVC7烷氧基、或為經鹵 素取代之C1-C7烷基或CrC7烷氧基； η 為0、1或2 ; 及醫藥活性酸加成鹽。 8.如請求項2之化合物，其中式][八之化合物為 (6-氯 _3,4·二氫-1Η-苯幷[4,5]噻吩幷[2,3_c]吡啶 _2_ 基H2-異丙氧基-5-曱烷磺醯基_苯基）_甲酮、 (6-氣-3,4-二氫_1H-苯幷[4,5]噻吩幷[2，夂比啶-入 基H5-甲烷磺醯基嗎啉基_4_基_苯基）·甲酮、 3_(6-氣-3,4·二氫·1H•苯幷[4,5]噻吩幷[2,3 cp比啶羰 基）-4-異丙氧基-笨幷腈、 (6_氣-3,4-二氫」H_苯幷[4,5]噻吩幷ο叫吡啶j 106827-971127.doc 基H2-環丙基曱氧基_5_甲烷磺醯基-苯基）_曱酮或 (6-氯-3,4-二氫·1H-苯幷[4,5]噻吩幷[2,3 c]吡啶-2· 基H5-曱料醯基_2_((s)_2,2,2·三氟小甲基-乙氧基苯 基]-甲酮。 9.如請求項3之化合物，其中式汨之化合物為 (2-異丁氧基-5-甲烷磺醯基·苯基）_(2_噻吩_2•基_6,7_二 氫-4H-噻唑幷[5,4-c]吡啶-5-基）-甲酮、 (2-異丙氧基-5-甲烷磺醯基-苯基）_(2•噻吩_2_基_6,7_二 氫_ 4H-%唑幷[5,4_c]吡啶基）_甲酮或 (2-異丁氧基-5-甲烷磺醯基·苯基）_[2_(4_三氟曱基·苯 基）-6,7-二氫_411-嗟咱_幷[5,4-〇]°比咬-5-基]_甲酮。 1〇·如請求項4之化合物，其中式1C之化合物為 (7-氣-3,4-二氫-1H-吡嗪幷[l，2-a]吲哚-2-基）·（2-異丙氧 基-5 -甲燒續酿基_苯基）_曱綱或 (2-異丙氧基_5_甲烷磺醯基_苯基）_(8_三氟甲氧基_3,4· 二氫-1Η-吡嗪幷[12-a]吲哚_2-基）_曱醐。 11. 如請求項5之化合物，其中式1〇之化合物為外消旋·〇異 丙氧基-5-甲烷磺醯基-苯基）_(8_三氟甲氧基_3,4，i〇，i〇a_ 四氫-1H-吡嗪幷吲哚_2_基）·甲酮。 12. 如請求項6之化合物，其中式IE之化合物為（2-環戊氧基巧_ 甲烷磺醯基-苯基）_(3,4-二氫·1H_苯幷[4,5]咪唑幷 吡嗪-2-基）_甲酮。 13· —種製備如請求項1之通式I之化合物的方法，該方法包 含： 106827-971127.doc II1299041 a)將選自由
組成之群之式
之化合物與式
之化合物於一諸如TBTU之活化劑存在下反應成式 0 R1
之化合物， 106827-971127.doc 1299041
其中該等取代基如請求項1中之定義，或 b)將式
0 X
之化合物與式
r'h V 之化合物於一諸如三乙胺之驗或一如Cu(I)Br之催化劑存 在下反應成式 106827-971127.doc -9- 1299041
之化合物，其中該等取代基R1、R2及
Λ 如請求項1中 之定義，且X為鹵素，或 c)式
VI 之化合物與式 之化合物反應成式
RX VII
0 OR
II 之化合物， 其中該等取代基R2 X為鹵素，或 R'及
Λ 如請求項1中之定義，且 d)式 106827-971127.doc -10- VI1299041
Q OH
R 之化合物與式
ROH VIII 之化合物於Mitsunobu條件下反應成式
0 OR
之化合物， 其中該等取代基R2、R，及 Λ 如上述之定義，且若需 要’則將該等獲得之化合物轉化為醫藥學上可接受之酸 加成鹽。
14.如凊求項1至12中任一項之化合物，其藉由如請求項13之 方法隨時製備。 15. —種用於治療關於經抑制作用活kNmda受體 之疾病的醫藥組合物，其含有一或多種如請求項丨至12中 任-項之化合物及醫藥學上可接受之職形劑，其中該疾 病係選自由精神病 '己憶及學習中之機能失調、精神分 、注意力不足症 治療阿茲海默氏 裂症、癡呆及認知過程受損之其他疾病 及阿茲海默氏病所組成之群。 16.如請求項15之醫藥組合物，其係用於 106827-971127.doc 1299041 (Alzheimer)病0 1 7. —種如請求項1至1 2中任一項之化合物之用途，其係用於 製造用於治療阿茲海默氏病之藥品。
106827-971127.doc 12·
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04106597 | 2004-12-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200634017A TW200634017A (en) | 2006-10-01 |
| TWI299041B true TWI299041B (en) | 2008-07-21 |
Family
ID=35841863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094143890A TWI299041B (en) | 2004-12-15 | 2005-12-12 | Bi-and tricyclic substituted phenyl methanones |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7375226B2 (zh) |
| EP (1) | EP1828200B1 (zh) |
| JP (1) | JP4709849B2 (zh) |
| KR (1) | KR100883003B1 (zh) |
| CN (1) | CN100586951C (zh) |
| AR (1) | AR052156A1 (zh) |
| AT (1) | ATE457989T1 (zh) |
| AU (1) | AU2005315914B2 (zh) |
| BR (1) | BRPI0519054A2 (zh) |
| CA (1) | CA2590316A1 (zh) |
| DE (1) | DE602005019465D1 (zh) |
| ES (1) | ES2338139T3 (zh) |
| IL (1) | IL183592A0 (zh) |
| MX (1) | MX2007006896A (zh) |
| NO (1) | NO20072833L (zh) |
| NZ (1) | NZ555476A (zh) |
| RU (1) | RU2007121768A (zh) |
| TW (1) | TWI299041B (zh) |
| WO (1) | WO2006063709A1 (zh) |
| ZA (1) | ZA200705044B (zh) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7485637B2 (en) * | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| RU2338537C2 (ru) * | 2006-01-25 | 2008-11-20 | Сергей Олегович Бачурин | СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ ШИЗОФРЕНИИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b)ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| KR102065319B1 (ko) | 2007-03-12 | 2020-01-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| EP2393878B1 (de) | 2009-02-06 | 2012-12-12 | Styrolution GmbH | Thermoplastische formmassen auf basis von styrolcopolymeren und polyamiden mit verbesserter witterungsbeständigkeit |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| TW201038569A (en) * | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
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-
2005
- 2005-12-05 ES ES05823127T patent/ES2338139T3/es not_active Expired - Lifetime
- 2005-12-05 WO PCT/EP2005/012994 patent/WO2006063709A1/en not_active Ceased
- 2005-12-05 EP EP05823127A patent/EP1828200B1/en not_active Expired - Lifetime
- 2005-12-05 AT AT05823127T patent/ATE457989T1/de active
- 2005-12-05 DE DE602005019465T patent/DE602005019465D1/de not_active Expired - Lifetime
- 2005-12-05 RU RU2007121768/04A patent/RU2007121768A/ru not_active Application Discontinuation
- 2005-12-05 CN CN200580042730A patent/CN100586951C/zh not_active Expired - Fee Related
- 2005-12-05 AU AU2005315914A patent/AU2005315914B2/en not_active Ceased
- 2005-12-05 CA CA002590316A patent/CA2590316A1/en not_active Abandoned
- 2005-12-05 KR KR1020077013440A patent/KR100883003B1/ko not_active Expired - Fee Related
- 2005-12-05 BR BRPI0519054-1A patent/BRPI0519054A2/pt not_active IP Right Cessation
- 2005-12-05 JP JP2007545891A patent/JP4709849B2/ja not_active Expired - Fee Related
- 2005-12-05 MX MX2007006896A patent/MX2007006896A/es active IP Right Grant
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- 2005-12-08 US US11/297,597 patent/US7375226B2/en not_active Expired - Fee Related
- 2005-12-12 TW TW094143890A patent/TWI299041B/zh not_active IP Right Cessation
- 2005-12-13 AR ARP050105207A patent/AR052156A1/es not_active Application Discontinuation
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- 2007-05-31 IL IL183592A patent/IL183592A0/en unknown
- 2007-06-04 NO NO20072833A patent/NO20072833L/no not_active Application Discontinuation
- 2007-06-07 ZA ZA200705044A patent/ZA200705044B/xx unknown
Also Published As
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|---|---|
| CN101076532A (zh) | 2007-11-21 |
| NO20072833L (no) | 2007-07-17 |
| WO2006063709A1 (en) | 2006-06-22 |
| IL183592A0 (en) | 2007-09-20 |
| ZA200705044B (en) | 2008-09-25 |
| DE602005019465D1 (de) | 2010-04-01 |
| US20060128713A1 (en) | 2006-06-15 |
| KR20070086196A (ko) | 2007-08-27 |
| ATE457989T1 (de) | 2010-03-15 |
| AR052156A1 (es) | 2007-03-07 |
| MX2007006896A (es) | 2007-06-26 |
| TW200634017A (en) | 2006-10-01 |
| ES2338139T3 (es) | 2010-05-04 |
| CA2590316A1 (en) | 2006-06-22 |
| JP2008523126A (ja) | 2008-07-03 |
| NZ555476A (en) | 2009-09-25 |
| CN100586951C (zh) | 2010-02-03 |
| BRPI0519054A2 (pt) | 2008-12-23 |
| EP1828200B1 (en) | 2010-02-17 |
| US7375226B2 (en) | 2008-05-20 |
| KR100883003B1 (ko) | 2009-02-12 |
| JP4709849B2 (ja) | 2011-06-29 |
| RU2007121768A (ru) | 2009-01-27 |
| AU2005315914A1 (en) | 2006-06-22 |
| EP1828200A1 (en) | 2007-09-05 |
| AU2005315914B2 (en) | 2011-03-03 |
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