AU2005209209B2 - Piperidinyl prostaglandin E analogs - Google Patents
Piperidinyl prostaglandin E analogs Download PDFInfo
- Publication number
- AU2005209209B2 AU2005209209B2 AU2005209209A AU2005209209A AU2005209209B2 AU 2005209209 B2 AU2005209209 B2 AU 2005209209B2 AU 2005209209 A AU2005209209 A AU 2005209209A AU 2005209209 A AU2005209209 A AU 2005209209A AU 2005209209 B2 AU2005209209 B2 AU 2005209209B2
- Authority
- AU
- Australia
- Prior art keywords
- oxo
- piperidin
- acetic acid
- phenyl
- enyl
- 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.)
- Ceased
Links
- -1 Piperidinyl prostaglandin E analogs Chemical class 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 27
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 23
- 206010030043 Ocular hypertension Diseases 0.000 claims abstract description 9
- 241001465754 Metazoa Species 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002997 ophthalmic solution Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- XEMXOPBICSGFHY-VVAUDMOXSA-N methyl 2-[(z)-4-[(6r)-2-oxo-6-[(e)-3-oxo-4-phenylbut-1-enyl]piperidin-1-yl]but-2-enoxy]acetate Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)OC)[C@H]1\C=C\C(=O)CC1=CC=CC=C1 XEMXOPBICSGFHY-VVAUDMOXSA-N 0.000 claims description 5
- 229940054534 ophthalmic solution Drugs 0.000 claims description 5
- PDOUDCKFVFFXHP-WNWYLPOESA-N 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C(\[C@@H]1N(C(=O)CCC1)CCCCOCC(O)=O)=C/C(O)CC1=CC=CC(Cl)=C1 PDOUDCKFVFFXHP-WNWYLPOESA-N 0.000 claims description 4
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- FCYFBWNXLWNVRR-IPOCZMARSA-N methyl 2-[(z)-4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]but-2-enoxy]acetate Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)OC)[C@H]1CCC(O)CC1=CC=CC=C1 FCYFBWNXLWNVRR-IPOCZMARSA-N 0.000 claims description 4
- AZAVKDBACSUNJM-SFFCAUCYSA-N methyl 2-[(z)-4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]but-2-enoxy]acetate Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)OC)[C@H]1CCC(=O)CC1=CC=CC=C1 AZAVKDBACSUNJM-SFFCAUCYSA-N 0.000 claims description 4
- WGVLUPHVOIIKAU-GNISGLHKSA-N methyl 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-oxobut-1-enyl]-6-oxopiperidin-1-yl]but-2-ynoxy]acetate Chemical compound C1CCC(=O)N(CC#CCOCC(=O)OC)[C@H]1\C=C\C(=O)CC1=CC=CC(Cl)=C1 WGVLUPHVOIIKAU-GNISGLHKSA-N 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- LPEUSZSVDXCEMU-WNWYLPOESA-N 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]but-2-ynoxy]acetic acid Chemical compound C(\[C@@H]1N(C(=O)CCC1)CC#CCOCC(O)=O)=C/C(O)CC1=CC=CC(Cl)=C1 LPEUSZSVDXCEMU-WNWYLPOESA-N 0.000 claims description 3
- AHYHCKDKOKOYEC-GOSISDBHSA-N 2-[4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]butoxy]acetic acid Chemical compound C1CCC(=O)N(CCCCOCC(=O)O)[C@H]1CCC(=O)CC1=CC=CC=C1 AHYHCKDKOKOYEC-GOSISDBHSA-N 0.000 claims description 3
- 101150047265 COR2 gene Proteins 0.000 claims description 3
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 3
- QUEZFBZMPJZXMY-SMNRKCEYSA-N methyl 2-[(z)-4-[(2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-6-oxopiperidin-1-yl]but-2-enoxy]acetate Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)OC)[C@H]1\C=C\C(O)CC1=CC=CC=C1 QUEZFBZMPJZXMY-SMNRKCEYSA-N 0.000 claims description 3
- UNLLTRAXOAFIER-AFZDNSHWSA-N methyl 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]but-2-ynoxy]acetate Chemical compound C1CCC(=O)N(CC#CCOCC(=O)OC)[C@H]1\C=C\C(O)CC1=CC=CC(Cl)=C1 UNLLTRAXOAFIER-AFZDNSHWSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
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- BQWMDNYVFXHHHA-YJWAVEFUSA-N propan-2-yl 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]but-2-ynoxy]acetate Chemical compound C1CCC(=O)N(CC#CCOCC(=O)OC(C)C)[C@H]1\C=C\C(O)CC1=CC=CC(Cl)=C1 BQWMDNYVFXHHHA-YJWAVEFUSA-N 0.000 claims description 3
- AKVCKIRUIWXCES-YJWAVEFUSA-N propan-2-yl 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-hydroxybut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetate Chemical compound C1CCC(=O)N(CCCCOCC(=O)OC(C)C)[C@H]1\C=C\C(O)CC1=CC=CC(Cl)=C1 AKVCKIRUIWXCES-YJWAVEFUSA-N 0.000 claims description 3
- QEIDWGFEZPFPRO-IENJSVCTSA-N 2-[4-[(6r)-2-oxo-6-[(e)-3-oxo-4-phenylbut-1-enyl]piperidin-1-yl]butoxy]acetic acid Chemical compound C1CCC(=O)N(CCCCOCC(=O)O)[C@H]1\C=C\C(=O)CC1=CC=CC=C1 QEIDWGFEZPFPRO-IENJSVCTSA-N 0.000 claims description 2
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- YWAGVVAYGSRGMN-FIWHBWSRSA-N methyl 2-[4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]butoxy]acetate Chemical compound C1CCC(=O)N(CCCCOCC(=O)OC)[C@H]1CCC(O)CC1=CC=CC=C1 YWAGVVAYGSRGMN-FIWHBWSRSA-N 0.000 claims description 2
- MEFIONCSVXFFDJ-QFJWKLLCSA-N methyl 2-[4-[(2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetate Chemical compound C1CCC(=O)N(CCCCOCC(=O)OC)[C@H]1\C=C\C(O)CC1=CC=CC=C1 MEFIONCSVXFFDJ-QFJWKLLCSA-N 0.000 claims description 2
- WIHHWVHGRTTZLC-LJQANCHMSA-N methyl 2-[4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]butoxy]acetate Chemical compound C1CCC(=O)N(CCCCOCC(=O)OC)[C@H]1CCC(=O)CC1=CC=CC=C1 WIHHWVHGRTTZLC-LJQANCHMSA-N 0.000 claims description 2
- HSIOTZHTJFRMOM-JXOMPUQVSA-N methyl 2-[4-[(6r)-2-oxo-6-[(e)-3-oxo-4-phenylbut-1-enyl]piperidin-1-yl]butoxy]acetate Chemical compound C1CCC(=O)N(CCCCOCC(=O)OC)[C@H]1\C=C\C(=O)CC1=CC=CC=C1 HSIOTZHTJFRMOM-JXOMPUQVSA-N 0.000 claims description 2
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- OHTBRSPZGKGPNX-WBVIWABJSA-N 2-[(z)-4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]but-2-enoxy]acetic acid Chemical compound C=1C=CC=CC=1CC(O)CC[C@H]1CCCC(=O)N1C\C=C/COCC(O)=O OHTBRSPZGKGPNX-WBVIWABJSA-N 0.000 claims 2
- RPKGGMKLCKYHFQ-PYTPGESOSA-N 2-[(z)-4-[(6r)-2-oxo-6-(3-oxo-4-phenylbutyl)piperidin-1-yl]but-2-enoxy]acetic acid Chemical compound C1CCC(=O)N(C\C=C/COCC(=O)O)[C@H]1CCC(=O)CC1=CC=CC=C1 RPKGGMKLCKYHFQ-PYTPGESOSA-N 0.000 claims 2
- PJHOQCPGTGEHBS-MRTLOADZSA-N 2-[4-[(2r)-2-(3-hydroxy-4-phenylbutyl)-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C=1C=CC=CC=1CC(O)CC[C@H]1CCCC(=O)N1CCCCOCC(O)=O PJHOQCPGTGEHBS-MRTLOADZSA-N 0.000 claims 2
- TXBOLWFTFXGCJQ-HRYKLGGKSA-N 2-[4-[(2r)-2-[(e)-3-hydroxy-4-phenylbut-1-enyl]-6-oxopiperidin-1-yl]butoxy]acetic acid Chemical compound C(\[C@@H]1N(C(=O)CCC1)CCCCOCC(O)=O)=C/C(O)CC1=CC=CC=C1 TXBOLWFTFXGCJQ-HRYKLGGKSA-N 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- OOGNHVJHKIAZID-MWTIFVBJSA-N sodium;hydride;methyl 2-[(z)-4-[(6r)-2-oxo-6-[(e)-3-oxo-4-phenylbut-1-enyl]piperidin-1-yl]but-2-enoxy]acetate Chemical compound [H-].[Na+].C1CCC(=O)N(C\C=C/COCC(=O)OC)[C@H]1\C=C\C(=O)CC1=CC=CC=C1 OOGNHVJHKIAZID-MWTIFVBJSA-N 0.000 description 1
- FWCSBLHATZDYIH-VLHGWARXSA-N sodium;hydride;methyl 2-[4-[(2r)-2-[(e)-4-(3-chlorophenyl)-3-oxobut-1-enyl]-6-oxopiperidin-1-yl]but-2-ynoxy]acetate Chemical compound [H-].[Na+].C1CCC(=O)N(CC#CCOCC(=O)OC)[C@H]1\C=C\C(=O)CC1=CC=CC(Cl)=C1 FWCSBLHATZDYIH-VLHGWARXSA-N 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 229940048910 thiosulfate Drugs 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 238000003260 vortexing Methods 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
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/45—Non condensed piperidines, e.g. piperocaine having oxo groups directly attached to the heterocyclic ring, e.g. cycloheximide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/763,702 | 2004-01-22 | ||
| US10/763,702 US6977260B2 (en) | 2004-01-22 | 2004-01-22 | Piperidinyl prostaglandin E analogs |
| PCT/US2005/001461 WO2005072735A1 (en) | 2004-01-22 | 2005-01-14 | Piperidinyl prostaglandin e analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005209209A1 AU2005209209A1 (en) | 2005-08-11 |
| AU2005209209B2 true AU2005209209B2 (en) | 2012-03-08 |
Family
ID=34795110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005209209A Ceased AU2005209209B2 (en) | 2004-01-22 | 2005-01-14 | Piperidinyl prostaglandin E analogs |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6977260B2 (enExample) |
| EP (1) | EP1722795B1 (enExample) |
| JP (1) | JP4740883B2 (enExample) |
| AR (1) | AR047436A1 (enExample) |
| AT (1) | ATE394101T1 (enExample) |
| AU (1) | AU2005209209B2 (enExample) |
| CA (1) | CA2553387C (enExample) |
| DE (1) | DE602005006534D1 (enExample) |
| ES (1) | ES2303672T3 (enExample) |
| TW (1) | TWI348370B (enExample) |
| WO (1) | WO2005072735A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7326716B2 (en) * | 2003-06-06 | 2008-02-05 | Allergan, Inc. | Treatment of inflammatory bowel disease |
| WO2006047466A2 (en) * | 2004-10-21 | 2006-05-04 | Duke University | Ophthamological drugs |
| US20070254920A1 (en) * | 2006-04-26 | 2007-11-01 | Aerie Pharmaceuticals, Inc. | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3220156C2 (de) * | 1982-05-28 | 1990-01-25 | Heida Houston Tex. Thurlow | Mit Metallgriffen, insbesondere Edelstahlgriffen, versehenes Koch- und Bratgeschirr mit Deckel |
| IT1225716B (it) * | 1988-10-26 | 1990-11-22 | Esacontrol Spa | Dispositivo per la protezione dei rele' di binario dai disturbi elettrici |
| CA2021316C (en) | 1989-07-27 | 2000-10-24 | Ming Fai Chan | Intraocular pressure reducing 11-acyl prostaglandins |
| US5034413A (en) | 1989-07-27 | 1991-07-23 | Allergan, Inc. | Intraocular pressure reducing 9,11-diacyl prostaglandins |
| US4994274A (en) | 1989-07-27 | 1991-02-19 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins and method of using |
| US5028624A (en) | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| DE4318713C1 (de) * | 1993-06-07 | 1994-09-15 | Daimler Benz Ag | Zahnräderwechselgetriebe der Vorgelegebauart |
| JP4766875B2 (ja) * | 2002-06-06 | 2011-09-07 | メルク フロスト カナダ リミテツド | Ｅｐ４受容体作動薬、組成物及びその方法 |
| US7053085B2 (en) | 2003-03-26 | 2006-05-30 | Merck & Co. Inc. | EP4 receptor agonist, compositions and methods thereof |
| WO2004063158A1 (en) | 2003-01-10 | 2004-07-29 | F.Hoffmann-La Roche Ag | 2-piperidone derivatives as prostaglandin agonists |
| US6747037B1 (en) * | 2003-06-06 | 2004-06-08 | Allergan, Inc. | Piperidinyl prostaglandin E analogs |
| WO2004108215A1 (en) * | 2003-06-06 | 2004-12-16 | Allergan, Inc. | Piperidinyl prostaglandin e analogs |
-
2004
- 2004-01-22 US US10/763,702 patent/US6977260B2/en not_active Expired - Lifetime
-
2005
- 2005-01-07 TW TW094100542A patent/TWI348370B/zh not_active IP Right Cessation
- 2005-01-14 DE DE602005006534T patent/DE602005006534D1/de not_active Expired - Lifetime
- 2005-01-14 CA CA2553387A patent/CA2553387C/en not_active Expired - Fee Related
- 2005-01-14 ES ES05705822T patent/ES2303672T3/es not_active Expired - Lifetime
- 2005-01-14 EP EP05705822A patent/EP1722795B1/en not_active Expired - Lifetime
- 2005-01-14 AT AT05705822T patent/ATE394101T1/de not_active IP Right Cessation
- 2005-01-14 WO PCT/US2005/001461 patent/WO2005072735A1/en not_active Ceased
- 2005-01-14 AU AU2005209209A patent/AU2005209209B2/en not_active Ceased
- 2005-01-14 JP JP2006551189A patent/JP4740883B2/ja not_active Expired - Fee Related
- 2005-01-20 AR ARP050100195A patent/AR047436A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE394101T1 (de) | 2008-05-15 |
| HK1099203A1 (en) | 2007-08-10 |
| ES2303672T3 (es) | 2008-08-16 |
| EP1722795A1 (en) | 2006-11-22 |
| AU2005209209A1 (en) | 2005-08-11 |
| WO2005072735A1 (en) | 2005-08-11 |
| US6977260B2 (en) | 2005-12-20 |
| TWI348370B (en) | 2011-09-11 |
| CA2553387A1 (en) | 2005-08-11 |
| TW200533350A (en) | 2005-10-16 |
| EP1722795B1 (en) | 2008-05-07 |
| AR047436A1 (es) | 2006-01-18 |
| US20050164990A1 (en) | 2005-07-28 |
| JP2007520489A (ja) | 2007-07-26 |
| JP4740883B2 (ja) | 2011-08-03 |
| DE602005006534D1 (de) | 2008-06-19 |
| CA2553387C (en) | 2013-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |