ES2312584T3 - Compuestos de espiropirazol. - Google Patents
Compuestos de espiropirazol. Download PDFInfo
- Publication number
- ES2312584T3 ES2312584T3 ES02739163T ES02739163T ES2312584T3 ES 2312584 T3 ES2312584 T3 ES 2312584T3 ES 02739163 T ES02739163 T ES 02739163T ES 02739163 T ES02739163 T ES 02739163T ES 2312584 T3 ES2312584 T3 ES 2312584T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- alkyl
- cycloalkyl
- group
- quad
- 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.)
- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 91
- -1 -CH2OH Chemical group 0.000 claims abstract description 151
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 62
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 39
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
- 150000002367 halogens Chemical group 0.000 claims abstract description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims abstract description 24
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 9
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 8
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005977 Ethylene Substances 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 208000002193 Pain Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 230000036407 pain Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000006623 cyclooctylmethyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 27
- 239000003112 inhibitor Substances 0.000 description 22
- 102000005962 receptors Human genes 0.000 description 22
- 108020003175 receptors Proteins 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 238000000034 method Methods 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000002552 dosage form Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000556 agonist Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 108090000137 Opioid Receptors Proteins 0.000 description 10
- 102000003840 Opioid Receptors Human genes 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 229940083542 sodium Drugs 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 239000001961 anticonvulsive agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
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- 229940124597 therapeutic agent Drugs 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 238000013270 controlled release Methods 0.000 description 4
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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Classifications
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- 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
- C07D471/10—Spiro-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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Dental Preparations (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28467501P | 2001-04-18 | 2001-04-18 | |
| US284675P | 2001-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2312584T3 true ES2312584T3 (es) | 2009-03-01 |
Family
ID=23091099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02739163T Expired - Lifetime ES2312584T3 (es) | 2001-04-18 | 2002-04-18 | Compuestos de espiropirazol. |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US6635653B2 (enExample) |
| EP (1) | EP1385515B1 (enExample) |
| JP (1) | JP4342181B2 (enExample) |
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| EP1551400A2 (en) * | 2002-10-17 | 2005-07-13 | Euro-Celtique S.A. | Preparation of triazospiro compounds |
| US20040242583A1 (en) * | 2003-01-20 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Pyrimido[5,4-e][1,2,4]triazine-5,7-diones, processes for preparing them and their use |
| WO2004103305A2 (en) * | 2003-05-16 | 2004-12-02 | Euroceltique S.A. | Spiropyrazole compound |
| WO2005011665A1 (en) * | 2003-07-22 | 2005-02-10 | Arakis Ltd. | The use of proglumide for the treatment of emesis |
| US20110008327A1 (en) | 2004-03-29 | 2011-01-13 | Cheng Jin Q | Compositions including triciribine and epidermal growth factor receptor inhibitor compounds or salts thereof and methods of use thereof |
| US20100173864A1 (en) | 2004-03-29 | 2010-07-08 | Cheng Jin Q | Compositions including triciribine and one or more platinum compounds and methods of use thereof |
| US20100009928A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and taxanes and methods of use thereof |
| US20100028339A1 (en) | 2004-03-29 | 2010-02-04 | Cheng Jin Q | Compositions including triciribine and trastuzumab and methods of use thereof |
| US20100009929A1 (en) | 2004-03-29 | 2010-01-14 | Cheng Jin Q | Compositions including triciribine and bortezomib and derivatives thereof and methods of use thereof |
| LT2574341T (lt) | 2004-03-29 | 2017-09-11 | University Of South Florida | Navikų ir vėžio efektyvus gydymas triciribino fosfatu |
| CN101137657B (zh) | 2005-03-08 | 2011-02-02 | 詹森药业有限公司 | 作为神经激肽（nk1）拮抗剂的二氮杂-螺-[4.4]-壬烷衍生物 |
| CN1870631B (zh) * | 2005-11-11 | 2010-04-14 | 华为技术有限公司 | 媒体网关的门控方法 |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| AU2007325355A1 (en) | 2006-11-28 | 2008-06-05 | Janssen Pharmaceutica N.V. | Salts of 3-(3-amino-2-(R)-hydroxy-propyl)-1-(4-fluoro-phenyl)-8-(8-methyl-naphthalen-1-ylmethyl) -1,3,8-triaza-spiro[4.5]decan-4-one |
| DE602008002690D1 (de) * | 2007-01-16 | 2010-11-04 | Purdue Pharma Lp | Heterozyklische substituierte piperidine als orl-1-liganden |
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| ES2920605T3 (es) | 2007-08-31 | 2022-08-05 | Purdue Pharma Lp | Intermedios de piperidina |
| NZ590416A (en) | 2008-07-21 | 2012-10-26 | Purdue Pharma Lp | Substituted-quinoxaline-type bridged-piperidine compounds and the uses thereof |
| UA107943C2 (xx) * | 2009-11-16 | 2015-03-10 | Lilly Co Eli | Сполуки спіропіперидину як антагоністи рецептора orl-1 |
| ES2613631T3 (es) | 2010-12-22 | 2017-05-25 | Purdue Pharma L.P. | Compuestos de piperidina de tipo quinoxalina sustituidos con fósforo y usos de los mismos |
| WO2013080036A1 (en) | 2011-12-01 | 2013-06-06 | Purdue Pharma L.P. | Azetidine-substituted quinoxaline-type piperidine compounds and uses thereof |
| US9085561B2 (en) | 2012-07-30 | 2015-07-21 | Purdue Pharma L.P. | Cyclic urea- or lactam-substituted quinoxaline-type piperidines as ORL-1 modulators |
| US9951038B2 (en) | 2012-12-27 | 2018-04-24 | Purdue Pharma L.P. | Quinazolin-4(3H)-one-type piperidine compounds and uses thereof |
| US9963458B2 (en) | 2012-12-27 | 2018-05-08 | Purdue Pharma L.P. | Indole and indoline-type piperidine compounds and uses thereof |
| US9090618B2 (en) | 2012-12-27 | 2015-07-28 | Purdue Pharma L.P. | Substituted benzimidazole-type piperidine compounds and uses thereof |
| WO2014102592A2 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Oxime/substituted quinoxaline-type piperidine compounds and uses thereof |
| WO2014102590A1 (en) | 2012-12-27 | 2014-07-03 | Purdue Pharma L.P. | Substituted piperidin-4-amino-type compounds and uses thereof |
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- 2002-04-18 RU RU2003133455/04A patent/RU2299883C2/ru not_active IP Right Cessation
- 2002-04-18 JP JP2002582928A patent/JP4342181B2/ja not_active Expired - Fee Related
- 2002-04-18 CA CA2444634A patent/CA2444634C/en not_active Expired - Fee Related
- 2002-04-18 AT AT02739163T patent/ATE403429T1/de active
- 2002-04-18 ES ES02739163T patent/ES2312584T3/es not_active Expired - Lifetime
- 2002-04-18 CZ CZ20032849A patent/CZ20032849A3/cs unknown
- 2002-04-18 CN CNA028121767A patent/CN1516584A/zh active Pending
- 2002-04-18 AU AU2002311833A patent/AU2002311833B2/en not_active Ceased
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- 2002-04-18 DK DK02739163T patent/DK1385515T3/da active
- 2002-04-18 UA UA20031110381A patent/UA74439C2/uk unknown
- 2002-04-18 EP EP02739163A patent/EP1385515B1/en not_active Expired - Lifetime
- 2002-04-18 YU YU82403A patent/YU82403A/sh unknown
- 2002-04-18 DE DE60228071T patent/DE60228071D1/de not_active Expired - Lifetime
- 2002-04-18 WO PCT/US2002/012376 patent/WO2002085355A1/en not_active Ceased
- 2002-04-18 SI SI200230748T patent/SI1385515T1/sl unknown
- 2002-04-18 KR KR1020037013821A patent/KR100628292B1/ko not_active Expired - Fee Related
- 2002-04-18 BR BRPI0209127-5A patent/BR0209127A/pt not_active Application Discontinuation
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- 2002-04-18 PL PL02367263A patent/PL367263A1/xx not_active Application Discontinuation
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- 2003-10-17 NO NO20034660A patent/NO20034660L/no not_active Application Discontinuation
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