JP2008513497A5 - - Google Patents
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- Publication number
- JP2008513497A5 JP2008513497A5 JP2007532624A JP2007532624A JP2008513497A5 JP 2008513497 A5 JP2008513497 A5 JP 2008513497A5 JP 2007532624 A JP2007532624 A JP 2007532624A JP 2007532624 A JP2007532624 A JP 2007532624A JP 2008513497 A5 JP2008513497 A5 JP 2008513497A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- unsubstituted
- substituted
- ylamino
- dimethyl
- 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.)
- Withdrawn
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- -1 R 31 Chemical compound 0.000 claims 38
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000001072 heteroaryl group Chemical group 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000004404 heteroalkyl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 125000002947 alkylene group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000004474 heteroalkylene group Chemical group 0.000 claims 8
- QMHIMXFNBOYPND-UHFFFAOYSA-N 4-methylthiazole Chemical compound CC1=CSC=N1 QMHIMXFNBOYPND-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 4
- 150000004677 hydrates Chemical class 0.000 claims 4
- 230000000155 isotopic effect Effects 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- WCSBMWHZVOVDHL-UHFFFAOYSA-N 2-methoxyethyl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OCCOC)NC(=O)C(C)CC1=NC(C)=CS1 WCSBMWHZVOVDHL-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- TXGZMBWIIVJJJG-UHFFFAOYSA-N methyl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC)NC(=O)C(C)CC1=NC(C)=CS1 TXGZMBWIIVJJJG-UHFFFAOYSA-N 0.000 claims 3
- LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- GSLKZZYLMSKRCG-UHFFFAOYSA-N tert-butyl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[2-[(4-methyl-1,3-thiazol-2-yl)methyl]butanoylamino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC(C)(C)C)NC(=O)C(CC)CC1=NC(C)=CS1 GSLKZZYLMSKRCG-UHFFFAOYSA-N 0.000 claims 3
- QTTSODGETAIHBF-UHFFFAOYSA-N tert-butyl n-[3-[[5-hydroxy-2-methyl-7-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]carbamoyl]nonan-4-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(CC)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC(C)(C)C)NC(=O)C(C)CC1=NC(C)=CS1 QTTSODGETAIHBF-UHFFFAOYSA-N 0.000 claims 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- KBOKLQRBBXZJKB-UHFFFAOYSA-N 5-[[3-acetamido-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]propanoyl]amino]-4-hydroxy-2,7-dimethyl-n-[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]octanamide Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(C)=O)NC(=O)C(C)CC1=NC(C)=CS1 KBOKLQRBBXZJKB-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ODUYCFAKSGVYDT-UHFFFAOYSA-N propan-2-yl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[2-[(4-methyl-1,3-thiazol-2-yl)methyl]butanoylamino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC(C)C)NC(=O)C(CC)CC1=NC(C)=CS1 ODUYCFAKSGVYDT-UHFFFAOYSA-N 0.000 claims 2
- DKFUWPHEVIJKPV-UHFFFAOYSA-N tert-butyl n-[3-[[3-hydroxy-5-methyl-6-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-6-oxo-1-phenylhexan-2-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound N=1C(C)=CSC=1CC(C)C(=O)NC(CNC(=O)OC(C)(C)C)C(=O)NC(C(O)CC(C)C(=O)NC(C(=O)NCC(C)C)C(C)C)CC1=CC=CC=C1 DKFUWPHEVIJKPV-UHFFFAOYSA-N 0.000 claims 2
- GUFJTLQVFGVMAQ-UHFFFAOYSA-N tert-butyl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC(C)(C)C)NC(=O)C(C)CC1=NC(C)=CS1 GUFJTLQVFGVMAQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- VAXPQIBUUIKOQG-UHFFFAOYSA-N 3-[(2,5-dimethyl-1,3-oxazol-4-yl)methoxycarbonylamino]-4-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-4-oxobutanoic acid Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CC(O)=O)NC(=O)OCC=1N=C(C)OC=1C VAXPQIBUUIKOQG-UHFFFAOYSA-N 0.000 claims 1
- RSSVMJSXZOMNBK-UHFFFAOYSA-N 4-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-3-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-4-oxobutanoic acid Chemical compound CC(C)CNC(=O)C(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CC(O)=O)NC(=O)C(C)CC1=NC(C)=CS1 RSSVMJSXZOMNBK-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims 1
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical class CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 claims 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- OGQZKOQUKGNNQZ-UHFFFAOYSA-N benzyl 3-[(2,5-dimethyl-1,3-oxazol-4-yl)methoxycarbonylamino]-4-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylamino)-1-oxobutan-2-yl]amino]-8-oxooctan-4-yl]amino]-4-oxobutanoate Chemical compound N1=C(C)OC(C)=C1COC(=O)NC(C(=O)NC(CC(C)C)C(O)CC(C)C(=O)NC(C(=O)NCC(C)C)C(C)C)CC(=O)OCC1=CC=CC=C1 OGQZKOQUKGNNQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- PHTXYPDLZQECFS-UHFFFAOYSA-N decan-5-ylcarbamic acid Chemical compound CCCCCC(NC(O)=O)CCCC PHTXYPDLZQECFS-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- PUMPRUWEZPVAPW-UHFFFAOYSA-N tert-butyl n-[3-[[5-hydroxy-2,7-dimethyl-8-[[3-methyl-1-(2-methylpropylsulfonyl)butan-2-yl]amino]-8-oxooctan-4-yl]amino]-2-[[2-methyl-3-(4-methyl-1,3-thiazol-2-yl)propanoyl]amino]-3-oxopropyl]carbamate Chemical compound CC(C)CS(=O)(=O)CC(C(C)C)NC(=O)C(C)CC(O)C(CC(C)C)NC(=O)C(CNC(=O)OC(C)(C)C)NC(=O)C(C)CC1=NC(C)=CS1 PUMPRUWEZPVAPW-UHFFFAOYSA-N 0.000 claims 1
- 125000005306 thianaphthenyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61102904P | 2004-09-17 | 2004-09-17 | |
| PCT/US2005/033709 WO2006034296A2 (en) | 2004-09-17 | 2005-09-19 | Amino-containing compounds which inhibit memapsin 2 beta-secretase activity and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008513497A JP2008513497A (ja) | 2008-05-01 |
| JP2008513497A5 true JP2008513497A5 (https=) | 2008-11-06 |
Family
ID=36090629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007532624A Withdrawn JP2008513497A (ja) | 2004-09-17 | 2005-09-19 | メマプシン２βセクレターゼ活性を阻害するアミノ含有化合物およびその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7659289B2 (https=) |
| EP (1) | EP1799660A2 (https=) |
| JP (1) | JP2008513497A (https=) |
| AU (1) | AU2005286774A1 (https=) |
| CA (1) | CA2580265A1 (https=) |
| WO (1) | WO2006034296A2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1799660A2 (en) | 2004-09-17 | 2007-06-27 | Comentis, Inc. | Amino-containing compounds which inhibit memapsin 2 beta-secretase activity and methods of use thereof |
| US8278345B2 (en) | 2006-11-09 | 2012-10-02 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| ATE554085T1 (de) | 2006-11-30 | 2012-05-15 | Probiodrug Ag | Neue inhibitoren von glutaminylcyclase |
| CN101209976B (zh) * | 2006-12-29 | 2012-01-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 取代的酒石酸衍生物及其用于制备β-分泌酶抑制剂的用途 |
| JP5930573B2 (ja) | 2007-03-01 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤の新規使用 |
| EP2142514B1 (en) | 2007-04-18 | 2014-12-24 | Probiodrug AG | Thiourea derivatives as glutaminyl cyclase inhibitors |
| US20100286145A1 (en) * | 2007-07-26 | 2010-11-11 | Comentis, Inc. | Isophthalamide derivatives inhibiting beta-secretase activity |
| JP5055432B2 (ja) * | 2007-09-24 | 2012-10-24 | コメンティス，インコーポレーテッド | 治療のためのβ−セクレターゼ阻害剤としての（３−ヒドロキシ−４−アミノブタン−２−イル）−３−（２−チアゾール−２−イル−ピロリジン−１−カルボニル）ベンズアミド誘導体及び関連する化合物 |
| JP5934645B2 (ja) | 2009-09-11 | 2016-06-15 | プロビオドルグ エージー | グルタミニルシクラーゼ阻害剤としてのヘテロ環式誘導体 |
| JP6026284B2 (ja) | 2010-03-03 | 2016-11-16 | プロビオドルグ エージー | グルタミニルシクラーゼの阻害剤 |
| NZ602312A (en) | 2010-03-10 | 2014-02-28 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| WO2011131748A2 (en) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Novel inhibitors |
| EP2686313B1 (en) | 2011-03-16 | 2016-02-03 | Probiodrug AG | Benzimidazole derivatives as inhibitors of glutaminyl cyclase |
| ES2812698T3 (es) | 2017-09-29 | 2021-03-18 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4911920A (en) | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| FR2588189B1 (fr) | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| US4902505A (en) | 1986-07-30 | 1990-02-20 | Alkermes | Chimeric peptides for neuropeptide delivery through the blood-brain barrier |
| US4801575A (en) | 1986-07-30 | 1989-01-31 | The Regents Of The University Of California | Chimeric peptides for neuropeptide delivery through the blood-brain barrier |
| US6407061B1 (en) | 1989-12-05 | 2002-06-18 | Chiron Corporation | Method for administering insulin-like growth factor to the brain |
| US5624898A (en) | 1989-12-05 | 1997-04-29 | Ramsey Foundation | Method for administering neurologic agents to the brain |
| JP2594486B2 (ja) | 1991-01-15 | 1997-03-26 | アルコン ラボラトリーズ インコーポレイテッド | 局所的眼薬組成物 |
| US5212162A (en) | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| US6287792B1 (en) | 1991-06-17 | 2001-09-11 | The Regents Of The University Of California | Drug delivery of antisense oligonucleotides and peptides to tissues in vivo and to cells using avidin-biotin technology |
| US6309853B1 (en) | 1994-08-17 | 2001-10-30 | The Rockfeller University | Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof |
| ES2298168T3 (es) | 1999-12-16 | 2008-05-16 | Emisphere Technologies, Inc. | Compuestos y composiciones para suministrar agentes activos. |
| EP1272222A2 (en) | 2000-04-12 | 2003-01-08 | Implyx Ltd. | Compositions for drug delivery |
| US6372250B1 (en) | 2000-04-25 | 2002-04-16 | The Regents Of The University Of California | Non-invasive gene targeting to the brain |
| US20040121947A1 (en) * | 2000-12-28 | 2004-06-24 | Oklahoma Medical Research Foundation | Compounds which inhibit beta-secretase activity and methods of use thereof |
| JP4547152B2 (ja) | 2001-10-23 | 2010-09-22 | オクラホマ メディカル リサーチ ファウンデーション | β−セクレターゼ阻害剤および使用方法 |
| WO2003100031A2 (en) | 2002-05-20 | 2003-12-04 | Board Of Regents, The University Of Texas System | Methods and compositions for delivering enzymes and nucleic acid molecules to brain, bone, and other tissues |
| US7388079B2 (en) | 2002-11-27 | 2008-06-17 | The Regents Of The University Of California | Delivery of pharmaceutical agents via the human insulin receptor |
| US20040102369A1 (en) | 2002-11-27 | 2004-05-27 | The Regents Of The University Of California | Transport of basic fibroblast growth factor across the blood brain barrier |
| EP1799660A2 (en) | 2004-09-17 | 2007-06-27 | Comentis, Inc. | Amino-containing compounds which inhibit memapsin 2 beta-secretase activity and methods of use thereof |
-
2005
- 2005-09-19 EP EP05812576A patent/EP1799660A2/en not_active Withdrawn
- 2005-09-19 WO PCT/US2005/033709 patent/WO2006034296A2/en not_active Ceased
- 2005-09-19 CA CA002580265A patent/CA2580265A1/en not_active Abandoned
- 2005-09-19 JP JP2007532624A patent/JP2008513497A/ja not_active Withdrawn
- 2005-09-19 US US11/662,915 patent/US7659289B2/en not_active Expired - Fee Related
- 2005-09-19 AU AU2005286774A patent/AU2005286774A1/en not_active Abandoned
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