JP2009538822A5 - - Google Patents
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- JP2009538822A5 JP2009538822A5 JP2008554421A JP2008554421A JP2009538822A5 JP 2009538822 A5 JP2009538822 A5 JP 2009538822A5 JP 2008554421 A JP2008554421 A JP 2008554421A JP 2008554421 A JP2008554421 A JP 2008554421A JP 2009538822 A5 JP2009538822 A5 JP 2009538822A5
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- JP
- Japan
- Prior art keywords
- certain embodiments
- compound
- formula
- virus
- iii
- 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.)
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- 239000000203 mixture Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 description 103
- 150000003839 salts Chemical class 0.000 description 55
- 238000001990 intravenous administration Methods 0.000 description 43
- 241000712461 unidentified influenza virus Species 0.000 description 39
- XRQDFNLINLXZLB-CKIKVBCHSA-N peramivir Chemical compound CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N XRQDFNLINLXZLB-CKIKVBCHSA-N 0.000 description 38
- 229960001084 peramivir Drugs 0.000 description 38
- 241000700605 Viruses Species 0.000 description 37
- 239000003814 drug Substances 0.000 description 33
- 241000282414 Homo sapiens Species 0.000 description 26
- 229940123424 Neuraminidase inhibitor Drugs 0.000 description 25
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- 238000000034 method Methods 0.000 description 21
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- 230000036470 plasma concentration Effects 0.000 description 15
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- VSZGPKBBMSAYNT-RRFJBIMHSA-N oseltamivir Chemical group CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1 VSZGPKBBMSAYNT-RRFJBIMHSA-N 0.000 description 4
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- 0 CCC(CC)C([*+])C(C)([C@@](C[C@]1*)NC(*)=N)[C@@]1OC1**1 Chemical compound CCC(CC)C([*+])C(C)([C@@](C[C@]1*)NC(*)=N)[C@@]1OC1**1 0.000 description 3
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOCBRFMNUQOMCY-PFGBXZAXSA-N (1r,3s,4r)-3-(1-acetamido-2-ethylbutyl)-4-(diaminomethylideneamino)cyclopentane-1-carboxylic acid Chemical compound CCC(CC)C(NC(C)=O)[C@@H]1C[C@@H](C(O)=O)C[C@H]1N=C(N)N FOCBRFMNUQOMCY-PFGBXZAXSA-N 0.000 description 1
- VUROMZOEXLKRSQ-CBNXCZCTSA-N (1r,3s,4r)-3-(1-acetamido-2-propylpentyl)-4-(diaminomethylideneamino)cyclopentane-1-carboxylic acid Chemical compound CCCC(CCC)C(NC(C)=O)[C@@H]1C[C@@H](C(O)=O)C[C@H]1NC(N)=N VUROMZOEXLKRSQ-CBNXCZCTSA-N 0.000 description 1
- XRQDFNLINLXZLB-GKWMMFDUSA-N (1s,2s,3s,4r)-3-(1-acetamido-2-ethylbutyl)-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid Chemical compound CCC(CC)C(NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1N=C(N)N XRQDFNLINLXZLB-GKWMMFDUSA-N 0.000 description 1
- IIZTWIZWLKRAMW-XUPBQHKHSA-N (1s,2s,3s,4r)-3-(1-acetamido-2-propylpentyl)-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid Chemical compound CCCC(CCC)C(NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1NC(N)=N IIZTWIZWLKRAMW-XUPBQHKHSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 101710154606 Hemagglutinin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000002979 Influenza in Birds Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 1
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710176177 Protein A56 Proteins 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000000185 hemagglutinin Substances 0.000 description 1
- 208000037797 influenza A Diseases 0.000 description 1
- 208000037798 influenza B Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000009520 phase I clinical trial Methods 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77274806P | 2006-02-13 | 2006-02-13 | |
| PCT/US2006/013535 WO2007117241A1 (fr) | 2006-04-12 | 2006-04-12 | Traitements antiviraux intramusculaires |
| PCT/US2007/003755 WO2007095218A1 (fr) | 2006-02-13 | 2007-02-12 | Traitements antiviraux intraveineux |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013174479A Division JP6073202B2 (ja) | 2006-02-13 | 2013-08-26 | 静脈におけるウイルスの治療 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009538822A JP2009538822A (ja) | 2009-11-12 |
| JP2009538822A5 true JP2009538822A5 (fr) | 2013-10-24 |
Family
ID=38169715
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008554421A Withdrawn JP2009538822A (ja) | 2006-02-13 | 2007-02-12 | 静脈におけるウイルスの治療 |
| JP2013174479A Active JP6073202B2 (ja) | 2006-02-13 | 2013-08-26 | 静脈におけるウイルスの治療 |
| JP2015137495A Withdrawn JP2015180695A (ja) | 2006-02-13 | 2015-07-09 | 静脈におけるウイルスの治療 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013174479A Active JP6073202B2 (ja) | 2006-02-13 | 2013-08-26 | 静脈におけるウイルスの治療 |
| JP2015137495A Withdrawn JP2015180695A (ja) | 2006-02-13 | 2015-07-09 | 静脈におけるウイルスの治療 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1986626A1 (fr) |
| JP (3) | JP2009538822A (fr) |
| KR (9) | KR20140132778A (fr) |
| AU (2) | AU2007215156A1 (fr) |
| BR (1) | BRPI0707769A2 (fr) |
| CA (1) | CA2642260C (fr) |
| EA (1) | EA025483B1 (fr) |
| HK (1) | HK1212250A1 (fr) |
| MX (2) | MX2008010394A (fr) |
| MY (1) | MY166063A (fr) |
| WO (1) | WO2007095218A1 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2008010394A (es) * | 2006-02-13 | 2009-01-12 | Biocryst Pharm Inc | Tratamientos antivirales intravenosos. |
| CN101367750B (zh) * | 2007-08-14 | 2012-05-23 | 中国人民解放军军事医学科学院毒物药物研究所 | (1s,2s,3s,4r)-3-[(1s)-1-乙酰氨-2-乙基-丁基]-4-胍基-2-羟基-环戊基-1-羧酸水合物及其医药用途 |
| KR20220033561A (ko) | 2020-09-07 | 2022-03-17 | 주식회사 경보제약 | 페라미비르 화합물을 포함하는 프리믹스 제형의 제약학적 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69735634T2 (de) * | 1996-06-14 | 2007-05-03 | Biocryst Pharmaceuticals, Inc., Birmingham | Substituierte cyclopentanderivate die als neuramidase-inhibitoren nuetzlich sind |
| AR016162A1 (es) * | 1997-12-17 | 2001-06-20 | Biocryst Pharm Inc | Compuestos ciclopentano y ciclopenteno sustituidos que son de utilidad como inhibidores de la neuraminidasa y composicion que los contiene. |
| GB0015324D0 (en) * | 2000-06-22 | 2000-08-16 | Biota Scient Management | Medicaments |
| MX2008010394A (es) * | 2006-02-13 | 2009-01-12 | Biocryst Pharm Inc | Tratamientos antivirales intravenosos. |
-
2007
- 2007-02-12 MX MX2008010394A patent/MX2008010394A/es active IP Right Grant
- 2007-02-12 WO PCT/US2007/003755 patent/WO2007095218A1/fr active Application Filing
- 2007-02-12 KR KR20147030611A patent/KR20140132778A/ko not_active Application Discontinuation
- 2007-02-12 BR BRPI0707769-6A patent/BRPI0707769A2/pt not_active Application Discontinuation
- 2007-02-12 KR KR1020207036259A patent/KR102267754B1/ko active IP Right Grant
- 2007-02-12 EP EP07750583A patent/EP1986626A1/fr not_active Ceased
- 2007-02-12 MX MX2020002008A patent/MX2020002008A/es unknown
- 2007-02-12 KR KR1020187005451A patent/KR101992585B1/ko active IP Right Review Request
- 2007-02-12 KR KR1020167030296A patent/KR20160129105A/ko not_active Application Discontinuation
- 2007-02-12 KR KR1020227042429A patent/KR20230003248A/ko not_active Application Discontinuation
- 2007-02-12 CA CA2642260A patent/CA2642260C/fr active Active
- 2007-02-12 JP JP2008554421A patent/JP2009538822A/ja not_active Withdrawn
- 2007-02-12 KR KR1020217018500A patent/KR102323339B1/ko active IP Right Grant
- 2007-02-12 KR KR1020087022406A patent/KR20080096829A/ko active Application Filing
- 2007-02-12 KR KR1020217035812A patent/KR102475176B1/ko active IP Right Grant
- 2007-02-12 AU AU2007215156A patent/AU2007215156A1/en not_active Abandoned
- 2007-02-12 KR KR1020197017311A patent/KR102194015B1/ko active IP Right Grant
- 2007-02-12 EA EA200870263A patent/EA025483B1/ru unknown
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2008
- 2008-08-13 MY MYPI20083086A patent/MY166063A/en unknown
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2013
- 2013-08-14 AU AU2013216632A patent/AU2013216632B2/en active Active
- 2013-08-26 JP JP2013174479A patent/JP6073202B2/ja active Active
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2015
- 2015-07-09 JP JP2015137495A patent/JP2015180695A/ja not_active Withdrawn
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2016
- 2016-01-14 HK HK16100369.5A patent/HK1212250A1/xx unknown
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