SK281095B6 - Hydroxynaftoát-4-hydroxy-alfa1-[[[6-(4- -fenylbutoxy)hexyl]amino]metyl]-1,3-benzéndimetanolu vhodný na mikronizáciu, spôsob jeho výroby, farmaceutická dávkovacia forma s jeho obsahom a jeho použitie - Google Patents
Hydroxynaftoát-4-hydroxy-alfa1-[[[6-(4- -fenylbutoxy)hexyl]amino]metyl]-1,3-benzéndimetanolu vhodný na mikronizáciu, spôsob jeho výroby, farmaceutická dávkovacia forma s jeho obsahom a jeho použitie Download PDFInfo
- Publication number
- SK281095B6 SK281095B6 SK545-93A SK54593A SK281095B6 SK 281095 B6 SK281095 B6 SK 281095B6 SK 54593 A SK54593 A SK 54593A SK 281095 B6 SK281095 B6 SK 281095B6
- Authority
- SK
- Slovakia
- Prior art keywords
- organic solvent
- hydroxynaphthoate
- microcrystals
- mixture
- water
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims abstract 4
- 238000000034 method Methods 0.000 title claims description 26
- 239000002552 dosage form Substances 0.000 title claims description 5
- 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 title abstract 2
- 239000003960 organic solvent Substances 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000002245 particle Substances 0.000 claims abstract description 24
- 239000013081 microcrystal Substances 0.000 claims abstract description 17
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 claims description 55
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims description 7
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000005215 alkyl ethers Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000003836 4-phenylbutoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- FWLBHDDQPNMYJD-UHFFFAOYSA-N OC1=C(C2=CC=CC=C2C=C1)C(=O)O.C1(=CC=CC=C1)CCCCOCCCCCCNCC1(CC(=CC=C1)CO)CO Chemical compound OC1=C(C2=CC=CC=C2C=C1)C(=O)O.C1(=CC=CC=C1)CCCCOCCCCCCNCC1(CC(=CC=C1)CO)CO FWLBHDDQPNMYJD-UHFFFAOYSA-N 0.000 claims 1
- 229960004217 benzyl alcohol Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- -1 isopropanyl Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 13
- 150000003839 salts Chemical class 0.000 abstract description 3
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 abstract 1
- SWPCURCTHNTSKL-UHFFFAOYSA-N C1=CC=CC2=C(O)C(C(=O)O)=CC=C21.C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21.C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 SWPCURCTHNTSKL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002152 aqueous-organic solution Substances 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 description 43
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 43
- 239000002904 solvent Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 208000023504 respiratory system disease Diseases 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 102100039705 Beta-2 adrenergic receptor Human genes 0.000 description 1
- 101710152983 Beta-2 adrenergic receptor Proteins 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- 238000007780 powder milling Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
- C07C217/10—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909026005A GB9026005D0 (en) | 1990-11-29 | 1990-11-29 | Drug material suitable for micronisation |
| PCT/GB1991/002108 WO1992009557A1 (en) | 1990-11-29 | 1991-11-28 | Benzenedimethanol suitable for micronisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK54593A3 SK54593A3 (en) | 1993-10-06 |
| SK281095B6 true SK281095B6 (sk) | 2000-11-07 |
Family
ID=10686212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK545-93A SK281095B6 (sk) | 1990-11-29 | 1991-11-28 | Hydroxynaftoát-4-hydroxy-alfa1-[[[6-(4- -fenylbutoxy)hexyl]amino]metyl]-1,3-benzéndimetanolu vhodný na mikronizáciu, spôsob jeho výroby, farmaceutická dávkovacia forma s jeho obsahom a jeho použitie |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5380922A (cs) |
| EP (2) | EP0639176B1 (cs) |
| JP (1) | JP3375626B2 (cs) |
| KR (1) | KR100192196B1 (cs) |
| AT (1) | ATE144244T1 (cs) |
| AU (1) | AU644505B2 (cs) |
| BG (1) | BG61340B1 (cs) |
| CA (1) | CA2099586C (cs) |
| CY (1) | CY2009A (cs) |
| CZ (1) | CZ282996B6 (cs) |
| DE (1) | DE69122780T2 (cs) |
| DK (1) | DK0639176T3 (cs) |
| ES (1) | ES2093812T3 (cs) |
| FI (2) | FI118155B (cs) |
| GB (1) | GB9026005D0 (cs) |
| GR (1) | GR3022088T3 (cs) |
| HK (1) | HK78997A (cs) |
| HU (1) | HU218205B (cs) |
| IE (1) | IE914146A1 (cs) |
| OA (2) | OA09861A (cs) |
| PL (2) | PL169722B1 (cs) |
| RU (2) | RU2197475C2 (cs) |
| SG (1) | SG49741A1 (cs) |
| SK (1) | SK281095B6 (cs) |
| TW (1) | TW309425B (cs) |
| WO (1) | WO1992009557A1 (cs) |
| ZA (1) | ZA919401B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9026005D0 (en) * | 1990-11-29 | 1991-01-16 | Glaxo Group Ltd | Drug material suitable for micronisation |
| WO1993016031A1 (en) * | 1992-02-11 | 1993-08-19 | Glaxo Group Limited | Benzenedimethanol derivative suitable for micronisation |
| US6254882B1 (en) | 1997-09-16 | 2001-07-03 | Sepracor Inc. | Methods and compositions for treating pulmonary disorders using optically pure (S)—salmeterol |
| EP1169019B1 (en) | 1999-04-14 | 2003-02-26 | Glaxo Group Limited | Pharmaceutical aerosol formulation |
| WO2002026239A1 (en) | 2000-09-26 | 2002-04-04 | Temple University Of The Commonwealth System Of Higher Education | Analgesic and glucosamine compositions |
| EP2127641A1 (en) | 2008-05-26 | 2009-12-02 | Inke, S.A. | Micronisable form of salmeterol xinafoate |
| KR101100614B1 (ko) | 2010-09-20 | 2011-12-29 | 한국수력원자력 주식회사 | 농축폐액 건조물의 펠렛화 장치 및 방법과 이를 이용한 유리조성개발 방법 |
| WO2016142582A1 (en) | 2015-03-11 | 2016-09-15 | Fermion Oy | Process for the preparation of crystalline salmeterol and its xinafoate salt |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| GB9026005D0 (en) * | 1990-11-29 | 1991-01-16 | Glaxo Group Ltd | Drug material suitable for micronisation |
-
1990
- 1990-11-29 GB GB909026005A patent/GB9026005D0/en active Pending
-
1991
- 1991-11-28 PL PL91308211A patent/PL169722B1/pl unknown
- 1991-11-28 SG SG1996004594A patent/SG49741A1/en unknown
- 1991-11-28 SK SK545-93A patent/SK281095B6/sk not_active IP Right Cessation
- 1991-11-28 RU RU97121416/04A patent/RU2197475C2/ru active
- 1991-11-28 DE DE69122780T patent/DE69122780T2/de not_active Expired - Lifetime
- 1991-11-28 JP JP50047092A patent/JP3375626B2/ja not_active Expired - Lifetime
- 1991-11-28 EP EP92900167A patent/EP0639176B1/en not_active Expired - Lifetime
- 1991-11-28 CA CA002099586A patent/CA2099586C/en not_active Expired - Lifetime
- 1991-11-28 PL PL91299352A patent/PL167976B1/pl unknown
- 1991-11-28 RU RU93040704A patent/RU2116293C1/ru active
- 1991-11-28 CZ CS931019A patent/CZ282996B6/cs not_active IP Right Cessation
- 1991-11-28 WO PCT/GB1991/002108 patent/WO1992009557A1/en active Application Filing
- 1991-11-28 ES ES92900167T patent/ES2093812T3/es not_active Expired - Lifetime
- 1991-11-28 AU AU90402/91A patent/AU644505B2/en not_active Ceased
- 1991-11-28 ZA ZA919401A patent/ZA919401B/xx unknown
- 1991-11-28 HU HU9301568A patent/HU218205B/hu unknown
- 1991-11-28 DK DK92900167.5T patent/DK0639176T3/da active
- 1991-11-28 AT AT92900167T patent/ATE144244T1/de not_active IP Right Cessation
- 1991-11-28 IE IE414691A patent/IE914146A1/en not_active IP Right Cessation
-
1992
- 1992-05-21 EP EP92304635A patent/EP0571669B1/en not_active Expired - Lifetime
- 1992-05-29 TW TW081104199A patent/TW309425B/zh active
-
1993
- 1993-05-14 OA OA60370A patent/OA09861A/en unknown
- 1993-05-14 US US08/050,298 patent/US5380922A/en not_active Expired - Lifetime
- 1993-05-25 BG BG97767A patent/BG61340B1/bg unknown
- 1993-05-27 FI FI932422A patent/FI118155B/fi not_active IP Right Cessation
- 1993-05-27 KR KR1019930701589A patent/KR100192196B1/ko not_active Expired - Lifetime
- 1993-09-24 OA OA60416A patent/OA10024A/en unknown
-
1996
- 1996-12-18 GR GR960403534T patent/GR3022088T3/el unknown
-
1997
- 1997-06-12 HK HK78997A patent/HK78997A/en not_active IP Right Cessation
-
1998
- 1998-02-20 CY CY200998A patent/CY2009A/xx unknown
- 1998-09-28 FI FI982081A patent/FI118203B/fi not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20111128 |