TW200306308A - Photochromic oxazine compounds and methods for their manufacture - Google Patents
Photochromic oxazine compounds and methods for their manufacture Download PDFInfo
- Publication number
- TW200306308A TW200306308A TW091136760A TW91136760A TW200306308A TW 200306308 A TW200306308 A TW 200306308A TW 091136760 A TW091136760 A TW 091136760A TW 91136760 A TW91136760 A TW 91136760A TW 200306308 A TW200306308 A TW 200306308A
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- Prior art keywords
- alkyl
- substituted
- group
- alkoxy
- aryl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000004893 oxazines Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 phenylethenyl Chemical group 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 26
- 239000007789 gas Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000001540 azides Chemical class 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 230000002079 cooperative effect Effects 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910000413 arsenic oxide Inorganic materials 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229940043279 diisopropylamine Drugs 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 229960002594 arsenic trioxide Drugs 0.000 claims description 4
- 125000004069 aziridinyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- IKWTVSLWAPBBKU-UHFFFAOYSA-N a1010_sial Chemical compound O=[As]O[As]=O IKWTVSLWAPBBKU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000005742 alkyl ethenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- NJISCFARZXISLM-UHFFFAOYSA-N 1-benzylphenanthrene Chemical compound C=1C=CC(C2=CC=CC=C2C=C2)=C2C=1CC1=CC=CC=C1 NJISCFARZXISLM-UHFFFAOYSA-N 0.000 claims 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 150000007857 hydrazones Chemical class 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- OSOLELDZBFOFHO-UHFFFAOYSA-N 2-phenylphenanthrene Chemical compound C1=CC=CC=C1C1=CC=C2C3=CC=CC=C3C=CC2=C1 OSOLELDZBFOFHO-UHFFFAOYSA-N 0.000 claims 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 229910052614 beryl Inorganic materials 0.000 claims 1
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims 1
- 125000005266 diarylamine group Chemical group 0.000 claims 1
- UGEHNPWNRKYBRU-UHFFFAOYSA-O diphenylsulfanium azide Chemical group [N-]=[N+]=[N-].C1(=CC=CC=C1)[SH+]C1=CC=CC=C1 UGEHNPWNRKYBRU-UHFFFAOYSA-O 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010304 firing Methods 0.000 claims 1
- 125000003106 haloaryl group Chemical group 0.000 claims 1
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 125000005289 uranyl group Chemical group 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/029,579 US6720420B2 (en) | 2001-12-21 | 2001-12-21 | Photochromic oxazine compounds and methods for their manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200306308A true TW200306308A (en) | 2003-11-16 |
Family
ID=21849773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091136760A TW200306308A (en) | 2001-12-21 | 2002-12-20 | Photochromic oxazine compounds and methods for their manufacture |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6720420B2 (https=) |
| EP (2) | EP1458695B1 (https=) |
| JP (1) | JP4486819B2 (https=) |
| KR (1) | KR100947062B1 (https=) |
| CN (1) | CN1305861C (https=) |
| AU (1) | AU2002362056B2 (https=) |
| BR (1) | BR0215264A (https=) |
| CA (1) | CA2471209C (https=) |
| IL (2) | IL162628A0 (https=) |
| MX (1) | MXPA04006197A (https=) |
| MY (1) | MY130997A (https=) |
| RU (1) | RU2315042C2 (https=) |
| TW (1) | TW200306308A (https=) |
| WO (1) | WO2003057679A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE445672T1 (de) * | 2005-03-14 | 2009-10-15 | Basf Se | Neue polymere |
| JP4445583B2 (ja) * | 2008-03-28 | 2010-04-07 | パナソニック株式会社 | 蓄電デバイス用電極活物質および蓄電デバイスならびに電子機器および輸送機器 |
| US8284385B2 (en) * | 2009-11-13 | 2012-10-09 | Lincoln Global, Inc. | Welding arc apparel with UV activated images |
| CN102702223A (zh) * | 2012-05-28 | 2012-10-03 | 盛世泰科生物医药技术(苏州)有限公司 | 一种2-溴-4-氯噻吩并[3,2-c]吡啶的制备方法 |
| CN110627770A (zh) | 2013-11-18 | 2019-12-31 | 福马疗法公司 | 作为bet溴域抑制剂的四氢喹啉组成物 |
| RU2720237C2 (ru) | 2013-11-18 | 2020-04-28 | Форма Терапеутикс, Инк. | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет |
| WO2019027346A1 (ru) * | 2017-08-02 | 2019-02-07 | Шамсият Абдурахмановна АЛИЛОВА | Многозональная фотохромная цветная контактная линза |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE156372C (https=) * | ||||
| DD153690B1 (de) | 1980-07-31 | 1986-11-05 | Manfred Reichenbaecher | Photochrome mittel |
| DD156372A1 (de) | 1981-02-13 | 1982-08-18 | Manfred Reichenbaecher | Photochrome medien unter verwendung von 1,4-2h-oxazinen und spirophenanthro-1,4-2h-oxazinen |
-
2001
- 2001-12-21 US US10/029,579 patent/US6720420B2/en not_active Expired - Fee Related
-
2002
- 2002-12-04 WO PCT/US2002/038743 patent/WO2003057679A1/en not_active Ceased
- 2002-12-04 AU AU2002362056A patent/AU2002362056B2/en not_active Ceased
- 2002-12-04 CN CNB028279972A patent/CN1305861C/zh not_active Expired - Fee Related
- 2002-12-04 RU RU2004118717/04A patent/RU2315042C2/ru not_active IP Right Cessation
- 2002-12-04 JP JP2003557996A patent/JP4486819B2/ja not_active Expired - Fee Related
- 2002-12-04 KR KR1020047009859A patent/KR100947062B1/ko not_active Expired - Fee Related
- 2002-12-04 IL IL16262802A patent/IL162628A0/xx unknown
- 2002-12-04 EP EP02797185A patent/EP1458695B1/en not_active Expired - Lifetime
- 2002-12-04 EP EP05076549.4A patent/EP1626046B1/en not_active Expired - Lifetime
- 2002-12-04 CA CA2471209A patent/CA2471209C/en not_active Expired - Fee Related
- 2002-12-04 MX MXPA04006197A patent/MXPA04006197A/es active IP Right Grant
- 2002-12-04 BR BR0215264-9A patent/BR0215264A/pt not_active Application Discontinuation
- 2002-12-19 MY MYPI20024796A patent/MY130997A/en unknown
- 2002-12-20 TW TW091136760A patent/TW200306308A/zh unknown
-
2004
- 2004-06-17 IL IL162628A patent/IL162628A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002362056B2 (en) | 2008-05-22 |
| EP1458695A1 (en) | 2004-09-22 |
| MXPA04006197A (es) | 2005-06-20 |
| WO2003057679A1 (en) | 2003-07-17 |
| BR0215264A (pt) | 2004-12-28 |
| EP1458695B1 (en) | 2012-10-03 |
| EP1626046B1 (en) | 2014-11-19 |
| JP2005520804A (ja) | 2005-07-14 |
| CA2471209C (en) | 2011-04-12 |
| CN1617861A (zh) | 2005-05-18 |
| CN1305861C (zh) | 2007-03-21 |
| KR20040068329A (ko) | 2004-07-30 |
| MY130997A (en) | 2007-07-31 |
| IL162628A0 (en) | 2005-11-20 |
| US20030149032A1 (en) | 2003-08-07 |
| KR100947062B1 (ko) | 2010-03-11 |
| RU2004118717A (ru) | 2005-03-27 |
| AU2002362056A1 (en) | 2003-07-24 |
| CA2471209A1 (en) | 2003-07-17 |
| JP4486819B2 (ja) | 2010-06-23 |
| WO2003057679A9 (en) | 2004-02-26 |
| IL162628A (en) | 2010-02-17 |
| US6720420B2 (en) | 2004-04-13 |
| EP1626046A1 (en) | 2006-02-15 |
| RU2315042C2 (ru) | 2008-01-20 |
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