JP2007516200A5 - - Google Patents
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- JP2007516200A5 JP2007516200A5 JP2006518343A JP2006518343A JP2007516200A5 JP 2007516200 A5 JP2007516200 A5 JP 2007516200A5 JP 2006518343 A JP2006518343 A JP 2006518343A JP 2006518343 A JP2006518343 A JP 2006518343A JP 2007516200 A5 JP2007516200 A5 JP 2007516200A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- spiro
- octane
- oxazolidine
- thiophen
- 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
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- -1 R 3 Chemical class 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 4
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000006017 1-propenyl group Chemical group 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 230000006735 deficit Effects 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000006038 hexenyl group Chemical group 0.000 claims 3
- 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 3
- 125000002346 iodo group Chemical group I* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 3
- TYAGAVRSOFABFO-UHFFFAOYSA-N spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound O1C(=O)NCC11C(CC2)CCN2C1 TYAGAVRSOFABFO-UHFFFAOYSA-N 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- ONLUCDBUROZPQZ-QGZVFWFLSA-N (5r)-3-(2-pyridin-3-yl-1,3-thiazol-4-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(N=1)=CSC=1C1=CC=CN=C1 ONLUCDBUROZPQZ-QGZVFWFLSA-N 0.000 claims 2
- PLUFRMLMVYJVRA-QGZVFWFLSA-N (5r)-3-(2-pyridin-3-yl-1,3-thiazol-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(S1)=CN=C1C1=CC=CN=C1 PLUFRMLMVYJVRA-QGZVFWFLSA-N 0.000 claims 2
- YGFUQGIYPFXQRL-QGZVFWFLSA-N (5r)-3-(2-pyridin-4-yl-1,3-thiazol-4-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(N=1)=CSC=1C1=CC=NC=C1 YGFUQGIYPFXQRL-QGZVFWFLSA-N 0.000 claims 2
- YZXOXLVSNMAQQD-QGZVFWFLSA-N (5r)-3-(2-pyridin-4-yl-1,3-thiazol-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(S1)=CN=C1C1=CC=NC=C1 YZXOXLVSNMAQQD-QGZVFWFLSA-N 0.000 claims 2
- JUXGDTBXNQMZFI-HXUWFJFHSA-N (5r)-3-[5-(3-methoxyphenyl)thiophen-2-yl]spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound COC1=CC=CC(C=2SC(=CC=2)N2C(O[C@@]3(C4CCN(CC4)C3)C2)=O)=C1 JUXGDTBXNQMZFI-HXUWFJFHSA-N 0.000 claims 2
- NJGIYZOSEBWUOK-LJQANCHMSA-N (5r)-3-[5-[3-(trifluoromethoxy)phenyl]thiophen-2-yl]spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound FC(F)(F)OC1=CC=CC(C=2SC(=CC=2)N2C(O[C@@]3(C4CCN(CC4)C3)C2)=O)=C1 NJGIYZOSEBWUOK-LJQANCHMSA-N 0.000 claims 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims 2
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 230000001713 cholinergic effect Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000006984 memory degeneration Effects 0.000 claims 2
- 208000023060 memory loss Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- IQZSFDJPGKPJOF-UHFFFAOYSA-N spiro[1-azabicyclo[2.2.2]octane-3,5'-4h-1,3-oxazole] Chemical compound C1N=COC11C(CC2)CCN2C1 IQZSFDJPGKPJOF-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- IFLYPJZUNYFMGO-GOSISDBHSA-N (5r)-3-(2-phenyl-1,3-oxazol-4-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(N=1)=COC=1C1=CC=CC=C1 IFLYPJZUNYFMGO-GOSISDBHSA-N 0.000 claims 1
- WUPCJGFKGNIKCY-GOSISDBHSA-N (5r)-3-(2-phenyl-1,3-oxazol-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(O1)=CN=C1C1=CC=CC=C1 WUPCJGFKGNIKCY-GOSISDBHSA-N 0.000 claims 1
- FDIWDKGCJZJCIU-GOSISDBHSA-N (5r)-3-(2-phenyl-1,3-thiazol-4-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(N=1)=CSC=1C1=CC=CC=C1 FDIWDKGCJZJCIU-GOSISDBHSA-N 0.000 claims 1
- APXGUGRSIUKRGK-GOSISDBHSA-N (5r)-3-(2-phenyl-1,3-thiazol-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(S1)=CN=C1C1=CC=CC=C1 APXGUGRSIUKRGK-GOSISDBHSA-N 0.000 claims 1
- WSLDNOHFXKPNIO-QGZVFWFLSA-N (5r)-3-(2-pyridin-2-yl-1,3-oxazol-4-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(N=1)=COC=1C1=CC=CC=N1 WSLDNOHFXKPNIO-QGZVFWFLSA-N 0.000 claims 1
- HOBPHYIQUKCPCO-QGZVFWFLSA-N (5r)-3-(2-pyridin-2-yl-1,3-oxazol-5-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(O1)=CN=C1C1=CC=CC=N1 HOBPHYIQUKCPCO-QGZVFWFLSA-N 0.000 claims 1
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- HOQYAUXAHINJML-QGZVFWFLSA-N (5r)-3-(4-pyridin-3-yl-1,3-thiazol-2-yl)spiro[1,3-oxazolidine-5,3'-1-azabicyclo[2.2.2]octane]-2-one Chemical compound C([C@@]1(OC2=O)C3CCN(CC3)C1)N2C(SC=1)=NC=1C1=CC=CN=C1 HOQYAUXAHINJML-QGZVFWFLSA-N 0.000 claims 1
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- 150000004820 halides Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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| MX2007006743A (es) * | 2004-12-15 | 2007-07-09 | Astrazeneca Ab | Ligandos del receptor de acetilcolina nicotinica. |
| US7652018B2 (en) | 2006-08-15 | 2010-01-26 | Wyeth Llc | Imidazolidin-2-one derivatives useful as PR modulators |
| TW200815428A (en) | 2006-08-15 | 2008-04-01 | Wyeth Corp | Oxazolidone derivatives as PR modulators |
| WO2008021337A1 (en) * | 2006-08-15 | 2008-02-21 | Wyeth | Oxazinan-2-one derivatives useful as pr modulators |
| US7649007B2 (en) | 2006-08-15 | 2010-01-19 | Wyeth Llc | Oxazolidine derivatives as PR modulators |
| US7618989B2 (en) | 2006-08-15 | 2009-11-17 | Wyeth | Tricyclic oxazolidone derivatives useful as PR modulators |
| EP2068903A4 (en) * | 2006-10-03 | 2010-11-03 | Galleon Pharmaceuticals Inc | S-NITROSOTHIOL COMPOUNDS AND RELATED DERIVATIVES |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| US7863291B2 (en) * | 2008-04-23 | 2011-01-04 | Bristol-Myers Squibb Company | Quinuclidine compounds as alpha-7 nicotinic acetylcholine receptor ligands |
| US8309577B2 (en) | 2008-04-23 | 2012-11-13 | Bristol-Myers Squibb Company | Quinuclidine compounds as α-7 nicotinic acetylcholine receptor ligands |
| MX2011000477A (es) * | 2008-07-17 | 2011-03-15 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas. |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| UA107791C2 (en) * | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| JP2013503152A (ja) * | 2009-08-27 | 2013-01-31 | イエダ リサーチ アンド ディベロップメント カンパニー リミテッド | オリゴフラン類、ポリフラン類、それらの作製および使用 |
| US8507516B2 (en) | 2009-10-28 | 2013-08-13 | Bristol-Myers Squibb Company | Azabicyclic compounds as alpha-7 nicotinic acetylcholine receptor ligands |
| US8278320B2 (en) | 2009-10-28 | 2012-10-02 | Bristol-Myers Squibb Company | Azabicyclo[2.2.1]heptane compounds as alpha-7 nicotinic acetylcholine receptor ligands |
| WO2011128304A2 (de) * | 2010-04-16 | 2011-10-20 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| CN103025744A (zh) | 2010-04-30 | 2013-04-03 | 百时美施贵宝公司 | 作为α-7烟碱乙酰胆碱受体配体前药的氮杂二环胺N-氧化物化合物 |
| AU2011281546B2 (en) | 2010-07-22 | 2014-07-10 | Novartis Ag | 2,3,5-trisubstituted thiophene compounds and uses thereof |
| CN103270029B (zh) | 2010-10-22 | 2016-01-20 | 拜耳知识产权有限责任公司 | 作为农药的杂环化合物 |
| MX2014011115A (es) | 2012-03-16 | 2015-03-13 | Axikin Pharmaceuticals Inc | Inhibidores de 3,5-diaminopirazol cinasa. |
| CN104884449A (zh) | 2012-10-31 | 2015-09-02 | 拜尔农作物科学股份公司 | 作为害虫防治剂的新的杂环化合物 |
| NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
| MY191736A (en) | 2014-12-23 | 2022-07-13 | Axikin Pharmaceuticals Inc | 3,5-diaminopyrazole kinase inhibitors |
| CN114539273A (zh) | 2016-06-07 | 2022-05-27 | 北京加科思新药研发有限公司 | 可用作shp2抑制剂的新型杂环衍生物 |
| HRP20241239T1 (hr) | 2017-03-23 | 2024-12-06 | Jacobio Pharmaceuticals Co., Ltd. | Novi heterociklički derivati korisni kao shp2 inhibitori |
| WO2020063760A1 (en) | 2018-09-26 | 2020-04-02 | Jacobio Pharmaceuticals Co., Ltd. | Novel heterocyclic derivatives useful as shp2 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855290A (en) * | 1985-05-10 | 1989-08-08 | State Of Israel, Represented By Prime Minister's Office, Israel Institute For Biological Research | Derivatives of quinuclidine |
| CZ289512B6 (cs) | 1994-08-24 | 2002-02-13 | Astra Aktiebolag | Spiro-azabicyklické sloučeniny pouľitelné při terapii |
| WO2001066546A1 (en) | 2000-03-09 | 2001-09-13 | Mitsubishi Pharma Corporation | Spiro compounds, process for preparing the same and use thereof as drugs |
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2004
- 2004-07-06 BR BRPI0412382-4A patent/BRPI0412382A/pt not_active IP Right Cessation
- 2004-07-06 WO PCT/GB2004/002904 patent/WO2005005435A1/en not_active Ceased
- 2004-07-06 AU AU2004255920A patent/AU2004255920B2/en not_active Ceased
- 2004-07-06 KR KR1020067000400A patent/KR20060057569A/ko not_active Ceased
- 2004-07-06 EP EP04743249A patent/EP1654264A1/en not_active Withdrawn
- 2004-07-06 CN CNA2004800218491A patent/CN1829721A/zh active Pending
- 2004-07-06 CA CA002531510A patent/CA2531510A1/en not_active Abandoned
- 2004-07-06 MX MXPA06000231A patent/MXPA06000231A/es active IP Right Grant
- 2004-07-06 JP JP2006518343A patent/JP2007516200A/ja active Pending
- 2004-07-06 NZ NZ545132A patent/NZ545132A/en unknown
- 2004-07-06 US US10/563,271 patent/US7514567B2/en not_active Expired - Fee Related
- 2004-07-07 AR ARP040102394A patent/AR045040A1/es not_active Application Discontinuation
- 2004-07-08 TW TW093120518A patent/TW200524942A/zh unknown
- 2004-07-11 SA SA04250212A patent/SA04250212B1/ar unknown
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2005
- 2005-12-22 IL IL172762A patent/IL172762A0/en unknown
-
2006
- 2006-01-06 ZA ZA200600154A patent/ZA200600154B/en unknown
- 2006-02-08 NO NO20060612A patent/NO20060612L/no not_active Application Discontinuation
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