NO330794B1 - Fremgangsmate for fremstilling av aminobenzopyranforbindelse - Google Patents
Fremgangsmate for fremstilling av aminobenzopyranforbindelse Download PDFInfo
- Publication number
- NO330794B1 NO330794B1 NO20051556A NO20051556A NO330794B1 NO 330794 B1 NO330794 B1 NO 330794B1 NO 20051556 A NO20051556 A NO 20051556A NO 20051556 A NO20051556 A NO 20051556A NO 330794 B1 NO330794 B1 NO 330794B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- dimethyl
- benzopyran
- product
- hydrazine
- Prior art date
Links
- -1 Aminobenzopyran Compound Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 27
- 239000002184 metal Substances 0.000 claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- SAXKWTPDZMBKSQ-UHFFFAOYSA-N 2,2'-dimethylchromene Natural products C1=CC=C2C=CC(C)(C)OC2=C1 SAXKWTPDZMBKSQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- MJVCBDKNZRGZDF-UHFFFAOYSA-N 2,2-dimethyl-6-nitrochromene Chemical compound C1=C([N+]([O-])=O)C=C2C=CC(C)(C)OC2=C1 MJVCBDKNZRGZDF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- RRJNLKVSQVLBFJ-UHFFFAOYSA-N 2,2-dimethylchromen-6-amine Chemical compound C1=C(N)C=C2C=CC(C)(C)OC2=C1 RRJNLKVSQVLBFJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002699 waste material Substances 0.000 abstract description 4
- 238000010626 work up procedure Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 17
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZGKVRYOUJKEBAL-UHFFFAOYSA-N 2h-chromen-2-amine Chemical class C1=CC=C2C=CC(N)OC2=C1 ZGKVRYOUJKEBAL-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000003440 anti-fibrillation Effects 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ACUOAQKUXNEDQR-UHFFFAOYSA-N 2,2-dimethyl-7-nitrochromene Chemical compound [O-][N+](=O)C1=CC=C2C=CC(C)(C)OC2=C1 ACUOAQKUXNEDQR-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- LEDMRZGFZIAGGB-UHFFFAOYSA-L strontium carbonate Chemical compound [Sr+2].[O-]C([O-])=O LEDMRZGFZIAGGB-UHFFFAOYSA-L 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002250112 | 2002-08-29 | ||
| PCT/JP2003/009987 WO2004020428A1 (ja) | 2002-08-29 | 2003-08-06 | アミノベンゾピラン化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20051556L NO20051556L (no) | 2005-03-23 |
| NO20051556D0 NO20051556D0 (no) | 2005-03-23 |
| NO330794B1 true NO330794B1 (no) | 2011-07-18 |
Family
ID=31972610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20051556A NO330794B1 (no) | 2002-08-29 | 2005-03-23 | Fremgangsmate for fremstilling av aminobenzopyranforbindelse |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7683189B2 (ja) |
| EP (1) | EP1535918B1 (ja) |
| JP (1) | JP4569755B2 (ja) |
| KR (1) | KR101078357B1 (ja) |
| CN (1) | CN100363358C (ja) |
| AT (1) | ATE486861T1 (ja) |
| AU (1) | AU2003252414B2 (ja) |
| CA (1) | CA2496847C (ja) |
| DE (1) | DE60334808D1 (ja) |
| DK (1) | DK1535918T3 (ja) |
| ES (1) | ES2353383T3 (ja) |
| HK (1) | HK1078874A1 (ja) |
| IL (1) | IL166886A (ja) |
| NO (1) | NO330794B1 (ja) |
| NZ (1) | NZ538745A (ja) |
| PT (1) | PT1535918E (ja) |
| RU (1) | RU2314302C2 (ja) |
| SI (1) | SI1535918T1 (ja) |
| TW (1) | TW200407318A (ja) |
| UA (1) | UA86000C2 (ja) |
| WO (1) | WO2004020428A1 (ja) |
| ZA (1) | ZA200501510B (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3026047A4 (en) | 2013-07-25 | 2017-05-17 | Nissan Chemical Industries, Ltd. | Method for producing heterocyclic compound |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121307A (en) | 1964-08-07 | 1968-07-24 | Wellcome Found | New chromans and chromenes |
| CH624395A5 (ja) * | 1976-01-08 | 1981-07-31 | Ciba Geigy Ag | |
| US5164509A (en) | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| JPH0578289A (ja) * | 1991-09-18 | 1993-03-30 | Mitsui Toatsu Chem Inc | ２，７−ビス（４−アミノフエノキシ）ナフタレンおよびその製造方法 |
| JP2896268B2 (ja) * | 1992-05-22 | 1999-05-31 | 三菱電機株式会社 | 半導体基板の表面処理装置及びその制御方法 |
| ATE311378T1 (de) | 1999-09-17 | 2005-12-15 | Nissan Chemical Ind Ltd | Benzopyran derivate |
| JP2001151767A (ja) | 1999-09-17 | 2001-06-05 | Nissan Chem Ind Ltd | ベンゾピラン誘導体 |
| DE10023484A1 (de) * | 2000-05-09 | 2001-11-22 | Schering Ag | Anthranylamide und deren Verwendung als Arzneimittel |
-
2003
- 2003-08-06 DK DK03791193.0T patent/DK1535918T3/da active
- 2003-08-06 CN CNB038200821A patent/CN100363358C/zh not_active Expired - Fee Related
- 2003-08-06 KR KR1020057003161A patent/KR101078357B1/ko not_active IP Right Cessation
- 2003-08-06 RU RU2005108665/04A patent/RU2314302C2/ru not_active IP Right Cessation
- 2003-08-06 EP EP03791193A patent/EP1535918B1/en not_active Expired - Lifetime
- 2003-08-06 CA CA2496847A patent/CA2496847C/en not_active Expired - Fee Related
- 2003-08-06 AU AU2003252414A patent/AU2003252414B2/en not_active Ceased
- 2003-08-06 US US10/524,686 patent/US7683189B2/en not_active Expired - Fee Related
- 2003-08-06 JP JP2004532686A patent/JP4569755B2/ja not_active Expired - Fee Related
- 2003-08-06 UA UAA200502758A patent/UA86000C2/ru unknown
- 2003-08-06 ZA ZA200501510A patent/ZA200501510B/xx unknown
- 2003-08-06 NZ NZ538745A patent/NZ538745A/en not_active IP Right Cessation
- 2003-08-06 AT AT03791193T patent/ATE486861T1/de active
- 2003-08-06 WO PCT/JP2003/009987 patent/WO2004020428A1/ja active Application Filing
- 2003-08-06 SI SI200331910T patent/SI1535918T1/sl unknown
- 2003-08-06 DE DE60334808T patent/DE60334808D1/de not_active Expired - Lifetime
- 2003-08-06 ES ES03791193T patent/ES2353383T3/es not_active Expired - Lifetime
- 2003-08-06 PT PT03791193T patent/PT1535918E/pt unknown
- 2003-08-11 TW TW092122022A patent/TW200407318A/zh not_active IP Right Cessation
-
2005
- 2005-02-14 IL IL166886A patent/IL166886A/en not_active IP Right Cessation
- 2005-03-23 NO NO20051556A patent/NO330794B1/no not_active IP Right Cessation
- 2005-12-01 HK HK05110983.3A patent/HK1078874A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1535918A1 (en) | 2005-06-01 |
| AU2003252414A1 (en) | 2004-03-19 |
| ZA200501510B (en) | 2006-10-25 |
| EP1535918B1 (en) | 2010-11-03 |
| EP1535918A4 (en) | 2007-04-18 |
| JP4569755B2 (ja) | 2010-10-27 |
| CA2496847C (en) | 2011-06-07 |
| KR20050036980A (ko) | 2005-04-20 |
| RU2005108665A (ru) | 2005-08-10 |
| DK1535918T3 (da) | 2011-01-10 |
| CN100363358C (zh) | 2008-01-23 |
| NZ538745A (en) | 2007-06-29 |
| NO20051556L (no) | 2005-03-23 |
| JPWO2004020428A1 (ja) | 2005-12-15 |
| TWI335324B (ja) | 2011-01-01 |
| ES2353383T3 (es) | 2011-03-01 |
| IL166886A (en) | 2008-08-07 |
| NO20051556D0 (no) | 2005-03-23 |
| PT1535918E (pt) | 2010-12-28 |
| HK1078874A1 (en) | 2006-03-24 |
| RU2314302C2 (ru) | 2008-01-10 |
| WO2004020428A1 (ja) | 2004-03-11 |
| ATE486861T1 (de) | 2010-11-15 |
| US20050192444A1 (en) | 2005-09-01 |
| SI1535918T1 (sl) | 2011-01-31 |
| US7683189B2 (en) | 2010-03-23 |
| DE60334808D1 (de) | 2010-12-16 |
| TW200407318A (en) | 2004-05-16 |
| KR101078357B1 (ko) | 2011-10-31 |
| AU2003252414B2 (en) | 2009-08-27 |
| UA86000C2 (ru) | 2009-03-25 |
| CN1678603A (zh) | 2005-10-05 |
| CA2496847A1 (en) | 2004-03-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |