JP2003533541A5 - - Google Patents
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- Publication number
- JP2003533541A5 JP2003533541A5 JP2001585538A JP2001585538A JP2003533541A5 JP 2003533541 A5 JP2003533541 A5 JP 2003533541A5 JP 2001585538 A JP2001585538 A JP 2001585538A JP 2001585538 A JP2001585538 A JP 2001585538A JP 2003533541 A5 JP2003533541 A5 JP 2003533541A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- lower alkyl
- alkyl
- carbamoyl
- hydroxy
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 description 89
- -1 aromatic-aliphatic Chemical group 0.000 description 55
- 229910052739 hydrogen Inorganic materials 0.000 description 46
- 239000001257 hydrogen Substances 0.000 description 46
- 125000004432 carbon atom Chemical group C* 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 41
- 229910052757 nitrogen Inorganic materials 0.000 description 40
- 125000001931 aliphatic group Chemical group 0.000 description 27
- 150000003839 salts Chemical class 0.000 description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 26
- 229910052760 oxygen Inorganic materials 0.000 description 26
- 239000001301 oxygen Chemical group 0.000 description 26
- 125000004414 alkyl thio group Chemical group 0.000 description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- 125000001589 carboacyl group Chemical group 0.000 description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 20
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 18
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 18
- 125000002950 monocyclic group Chemical group 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 14
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 13
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Chemical group 0.000 description 12
- 239000011593 sulfur Chemical group 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 230000002062 proliferating effect Effects 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000001041 indolyl group Chemical group 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- YFCDKSCUZCBUJQ-LBPRGKRZSA-N (2s)-2-amino-n-[(2-hydroxy-4-methoxyphenyl)methyl]-3-methylbutanamide Chemical compound COC1=CC=C(CNC(=O)[C@@H](N)C(C)C)C(O)=C1 YFCDKSCUZCBUJQ-LBPRGKRZSA-N 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- 125000005936 piperidyl group Chemical group 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007929 subcutaneous injection Substances 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 241000699660 Mus musculus Species 0.000 description 3
- 102000004245 Proteasome Endopeptidase Complex Human genes 0.000 description 3
- 108090000708 Proteasome Endopeptidase Complex Proteins 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 239000012510 hollow fiber Substances 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000011580 nude mouse model Methods 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 208000037841 lung tumor Diseases 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 208000023958 prostate neoplasm Diseases 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000003104 tissue culture media Substances 0.000 description 2
- PTVBXXOOKHBSMR-OOJKEJCUSA-N (2r,3r,4s)-4-[[(2s)-3,3-dimethyl-2-[(2-naphthalen-1-ylacetyl)amino]butanoyl]amino]-3-hydroxy-2-(naphthalen-1-ylmethylamino)-5-phenylpentanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)CC=1C2=CC=CC=C2C=CC=1)C(C)(C)C)[C@@H](O)[C@@H](NCC=1C2=CC=CC=C2C=CC=1)C(O)=O)C1=CC=CC=C1 PTVBXXOOKHBSMR-OOJKEJCUSA-N 0.000 description 1
- QDKMUWAUVPMBMF-KHQRGBKLSA-N (2r,3r,4s)-4-[[(2s)-3,3-dimethyl-2-[(2-naphthalen-1-ylacetyl)amino]butanoyl]amino]-3-hydroxy-5-phenyl-2-[(2,3,4-trimethoxyphenyl)methylamino]pentanoic acid Chemical compound COC1=C(OC)C(OC)=CC=C1CN[C@@H](C(O)=O)[C@H](O)[C@@H](NC(=O)[C@@H](NC(=O)CC=1C2=CC=CC=C2C=CC=1)C(C)(C)C)CC1=CC=CC=C1 QDKMUWAUVPMBMF-KHQRGBKLSA-N 0.000 description 1
- DTMIVCFTZKWUCT-RHHFKYMDSA-N (2r,3r,4s)-4-[[(2s)-3,3-dimethyl-2-[(2-naphthalen-1-ylacetyl)amino]butanoyl]amino]-3-hydroxy-5-phenyl-2-[(2,4,5-trimethoxyphenyl)methylamino]pentanoic acid Chemical compound COC1=CC(OC)=C(OC)C=C1CN[C@@H](C(O)=O)[C@H](O)[C@@H](NC(=O)[C@@H](NC(=O)CC=1C2=CC=CC=C2C=CC=1)C(C)(C)C)CC1=CC=CC=C1 DTMIVCFTZKWUCT-RHHFKYMDSA-N 0.000 description 1
- QGTBFDVWPPMKSZ-NQQZCUSYSA-N (2r,3r,4s)-4-[[(2s)-3,3-dimethyl-2-[(2-naphthalen-1-ylacetyl)amino]butanoyl]amino]-3-hydroxy-5-phenyl-2-[(3,4,5-trimethoxyphenyl)methylamino]pentanoic acid Chemical compound COC1=C(OC)C(OC)=CC(CN[C@H]([C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](NC(=O)CC=2C3=CC=CC=C3C=CC=2)C(C)(C)C)C(O)=O)=C1 QGTBFDVWPPMKSZ-NQQZCUSYSA-N 0.000 description 1
- VOXZDWNPVJITMN-UHFFFAOYSA-N 13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2C3CCC(C)(C(CC4)O)C4C3CCC2=C1 VOXZDWNPVJITMN-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 102000016736 Cyclin Human genes 0.000 description 1
- 108050006400 Cyclin Proteins 0.000 description 1
- 208000005016 Intestinal Neoplasms Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- CGXQNAZMWWXOPP-BCJPODAPSA-N [(2S)-1-[[(2S,3R,4R)-5-[[(2S)-1-[(5-bromo-2-hydroxyphenyl)methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-hydroxy-4-[(4-methoxyphenyl)methylamino]-5-oxo-1-phenylpentan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]carbamic acid Chemical compound C(C1=CC=CC=C1)[C@@H]([C@H]([C@@H](NCC1=CC=C(C=C1)OC)C(N[C@@H](C(C)C)C(NCC1=C(C=CC(=C1)Br)O)=O)=O)O)NC(=O)[C@H](C(C)(C)C)NC(O)=O CGXQNAZMWWXOPP-BCJPODAPSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 201000009019 intestinal benign neoplasm Diseases 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0012795.1 | 2000-05-25 | ||
| GBGB0012795.1A GB0012795D0 (en) | 2000-05-25 | 2000-05-25 | Organic compounds |
| PCT/EP2001/005952 WO2001089282A2 (en) | 2000-05-25 | 2001-05-23 | 2-amino-3-hydroxy-4-tert-leucyl-amino-5-phenyl-pentanoic acid amide derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003533541A JP2003533541A (ja) | 2003-11-11 |
| JP2003533541A5 true JP2003533541A5 (enExample) | 2008-06-19 |
Family
ID=9892401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001585538A Pending JP2003533541A (ja) | 2000-05-25 | 2001-05-23 | ２−アミノ−３−ヒドロキシ−４−ｔｅｒｔ−ロイシル−アミノ−５−フェニル−ペンタン酸アミド誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20030166572A1 (enExample) |
| EP (1) | EP1290012B1 (enExample) |
| JP (1) | JP2003533541A (enExample) |
| AT (1) | ATE325809T1 (enExample) |
| AU (1) | AU2001266019A1 (enExample) |
| CA (1) | CA2405871A1 (enExample) |
| DE (1) | DE60119514T2 (enExample) |
| ES (1) | ES2261422T3 (enExample) |
| GB (1) | GB0012795D0 (enExample) |
| PT (1) | PT1290012E (enExample) |
| WO (1) | WO2001089282A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006508166A (ja) * | 2002-11-27 | 2006-03-09 | イーラン ファーマスーティカルズ、インコーポレイテッド | 置換尿素及びカルバメート |
| GB0504950D0 (en) * | 2005-03-10 | 2005-04-20 | Novartis Ag | Organic compositions |
| CA2604133C (en) | 2005-04-07 | 2015-12-01 | Centre National De La Recherche Scientifique | Compounds useful as modulators of the proteasome activity |
| EP2257281A2 (en) * | 2008-02-28 | 2010-12-08 | Novartis AG | Combination comprising a cannabinoid receptor binding compound and an opioid |
| WO2010096574A1 (en) | 2009-02-20 | 2010-08-26 | Lisanti Michael P | A method of diagnosis or prognosis of a neoplasm comprising determining the level of expression of a protein in stromal cells adjacent to the neoplasm |
| US10085987B2 (en) | 2012-01-27 | 2018-10-02 | Thomas Jefferson University | MCT protein inhibitor-related prognostic and therapeutic methods |
| EP2986290A4 (en) | 2013-04-19 | 2017-01-04 | Thomas Jefferson University | Caveolin-1 related methods for treating glioblastoma with temozolomide |
| CN118373875A (zh) * | 2018-05-29 | 2024-07-23 | 奥默罗斯公司 | Masp-2抑制剂和使用方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5538997A (en) * | 1993-03-12 | 1996-07-23 | Sandoz Ltd. | 2,4-diamino-3-hydroxycarboxylic acid derivatives |
| EP0982317A1 (en) * | 1998-08-26 | 2000-03-01 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Bivalent inhibitors of the proteasome |
| EP1173413B1 (en) * | 1999-04-27 | 2004-06-30 | Novartis AG | Use of 2,4-diamino-3-hydroxycarboxylic acid derivatives as proteasome inhibitors |
-
2000
- 2000-05-25 GB GBGB0012795.1A patent/GB0012795D0/en not_active Ceased
-
2001
- 2001-05-23 PT PT01943442T patent/PT1290012E/pt unknown
- 2001-05-23 AT AT01943442T patent/ATE325809T1/de not_active IP Right Cessation
- 2001-05-23 AU AU2001266019A patent/AU2001266019A1/en not_active Abandoned
- 2001-05-23 JP JP2001585538A patent/JP2003533541A/ja active Pending
- 2001-05-23 US US10/258,901 patent/US20030166572A1/en not_active Abandoned
- 2001-05-23 EP EP01943442A patent/EP1290012B1/en not_active Expired - Lifetime
- 2001-05-23 WO PCT/EP2001/005952 patent/WO2001089282A2/en not_active Ceased
- 2001-05-23 DE DE60119514T patent/DE60119514T2/de not_active Expired - Fee Related
- 2001-05-23 CA CA002405871A patent/CA2405871A1/en not_active Abandoned
- 2001-05-23 ES ES01943442T patent/ES2261422T3/es not_active Expired - Lifetime
-
2006
- 2006-05-15 US US11/434,398 patent/US20060205673A1/en not_active Abandoned
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