CZ284209B6 - 7-Nitro-9-substituovaný amino-6-demethyl-6-deoxytetracykliny a způsoby jejich výroby - Google Patents
7-Nitro-9-substituovaný amino-6-demethyl-6-deoxytetracykliny a způsoby jejich výroby Download PDFInfo
- Publication number
- CZ284209B6 CZ284209B6 CZ973093A CZ309397A CZ284209B6 CZ 284209 B6 CZ284209 B6 CZ 284209B6 CZ 973093 A CZ973093 A CZ 973093A CZ 309397 A CZ309397 A CZ 309397A CZ 284209 B6 CZ284209 B6 CZ 284209B6
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- amino
- alkyl
- carbon atoms
- substituted
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Moulding By Coating Moulds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77157691A | 1991-10-04 | 1991-10-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ284209B6 true CZ284209B6 (cs) | 1998-09-16 |
| CZ309397A3 CZ309397A3 (cs) | 1998-09-16 |
Family
ID=25092264
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ973093A CZ309397A3 (cs) | 1991-10-04 | 1992-09-30 | 7-Nitro-9-substituovaný amino-6-demethyl-6-deoxytetracykliny a způsoby jejich výroby |
| CS922984A CZ284159B6 (cs) | 1991-10-04 | 1992-09-30 | 7-Substituovaný-9-substituovaný amino-6-demethyl-6-deoxytetracykliny, způsoby a meziprodukty pro jejich výrobu s farmaceutické prostředky na jejich bázi |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS922984A CZ284159B6 (cs) | 1991-10-04 | 1992-09-30 | 7-Substituovaný-9-substituovaný amino-6-demethyl-6-deoxytetracykliny, způsoby a meziprodukty pro jejich výrobu s farmaceutické prostředky na jejich bázi |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0536515B1 (enExample) |
| JP (1) | JP3186863B2 (enExample) |
| KR (1) | KR100269072B1 (enExample) |
| CN (1) | CN1048240C (enExample) |
| AT (1) | ATE211128T1 (enExample) |
| AU (1) | AU654049B2 (enExample) |
| BR (1) | BR1100853A (enExample) |
| CA (1) | CA2079692C (enExample) |
| CL (1) | CL2004001623A1 (enExample) |
| CZ (2) | CZ309397A3 (enExample) |
| DE (4) | DE69232302D1 (enExample) |
| DK (1) | DK0536515T3 (enExample) |
| ES (1) | ES2168254T3 (enExample) |
| FI (1) | FI114911B (enExample) |
| HU (2) | HU219973B (enExample) |
| IL (3) | IL103320A (enExample) |
| LU (1) | LU91279I2 (enExample) |
| MX (1) | MX9205532A (enExample) |
| NL (1) | NL300244I1 (enExample) |
| NO (3) | NO301472B1 (enExample) |
| NZ (1) | NZ244585A (enExample) |
| PL (4) | PL176333B1 (enExample) |
| PT (1) | PT536515E (enExample) |
| SG (1) | SG52361A1 (enExample) |
| SK (2) | SK280837B6 (enExample) |
| TW (1) | TW275616B (enExample) |
| ZA (1) | ZA927607B (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328902A (en) * | 1992-08-13 | 1994-07-12 | American Cyanamid Co. | 7-(substituted)-9-[(substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| US5420272A (en) * | 1992-08-13 | 1995-05-30 | American Cyanamid Company | 7-(substituted)-8-(substituted)-9-](substituted glycyl)amido]-6-demethyl-6-deoxytetracyclines |
| US5284963A (en) * | 1992-08-13 | 1994-02-08 | American Cyanamid Company | Method of producing 7-(substituted)-9-[(substituted glycyl)-amidol]-6-demethyl-6-deoxytetra-cyclines |
| AU1279095A (en) * | 1994-02-17 | 1995-09-04 | Pfizer Inc. | 9-(substituted amino)-alpha-6-deoxy-5-oxy tetracycline derivatives, their preparation and their use as antibiotics |
| CZ301835B6 (cs) | 1999-09-14 | 2010-07-07 | Trustees Of Tufts College | Zpusob prípravy 7-, 9- nebo 13- substituované tetracyklinové slouceniny, reaktivní tetracyklinový chemický komplex a tetracyklinová sloucenina substituovaná v poloze 7 nebo 9 |
| US8106225B2 (en) | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
| KR20030007489A (ko) * | 2000-03-31 | 2003-01-23 | 트러스티즈 오브 터프츠 칼리지 | 7- 및 9-카르바메이트, 우레아, 티오우레아,티오카르바메이트 및 헤테로아릴-아미노 치환된테트라사이클린 화합물 |
| EP2308863A1 (en) * | 2000-05-15 | 2011-04-13 | Paratek Pharmaceuticals, Inc. | 7-substituted fused ring tetracycline compounds |
| CN1690047B (zh) * | 2000-07-07 | 2010-10-06 | 塔夫茨大学信托人 | 9-取代的二甲胺四环素化合物 |
| US7094806B2 (en) | 2000-07-07 | 2006-08-22 | Trustees Of Tufts College | 7, 8 and 9-substituted tetracycline compounds |
| US7553828B2 (en) | 2001-03-13 | 2009-06-30 | Paratek Pharmaceuticals, Inc. | 9-aminomethyl substituted minocycline compounds |
| EP1241160A1 (en) | 2001-03-13 | 2002-09-18 | Glaxo Group Limited | Tetracycline derivatives and their use as antibiotic agents |
| EA201000388A1 (ru) | 2001-03-13 | 2010-10-29 | Пэрэтек Фамэсьютикэлс, Инк. | Замещенные соединения тетрациклина (варианты), фармацевтическая композиция и способ лечения чувствительного к тетрациклину состояния субъекта |
| WO2002072506A2 (en) | 2001-03-13 | 2002-09-19 | Paratek Pharmaceuticals, Inc. | 7-pyrollyl tetracycline compounds and methods of use thereof |
| EP2186793A1 (en) * | 2001-04-24 | 2010-05-19 | Paratek Pharmaceuticals, Inc. | Substituted Tetracycline Compounds |
| EP2301550A1 (en) | 2001-07-13 | 2011-03-30 | Paratek Pharmaceuticals, Inc. | Tetracycline compounds having target therapeutic activities |
| AU2002365120A1 (en) | 2001-08-02 | 2003-07-15 | Paratek Pharmaceuticals, Inc. | Medicaments |
| EP2311799A1 (en) | 2002-01-08 | 2011-04-20 | Paratek Pharmaceuticals, Inc. | 4-dedimethylamino tetracycline compounds |
| EA201000491A1 (ru) * | 2002-03-08 | 2010-08-30 | Паратек Фармасьютикалс, Инк. | Аминометилзамещенные тетрациклиновые соединения |
| KR101228706B1 (ko) | 2003-07-09 | 2013-02-01 | 파라테크 파마슈티컬스, 인크. | 치환된 테트라시클린 화합물 |
| UA83266C2 (en) * | 2003-12-08 | 2008-06-25 | Уайет | Oxazole derivatives of tetracyclines |
| PL1753713T3 (pl) | 2004-05-21 | 2017-02-28 | President And Fellows Of Harvard College | Synteza tetracyklin oraz ich analogów |
| PA8652001A1 (es) | 2004-11-05 | 2006-10-13 | Wyeth Corp | Metabolitos glucuronidos de tigeciclina y epimeros de los mismos |
| AR057649A1 (es) | 2005-05-27 | 2007-12-12 | Wyeth Corp | Formas solidas cristalinas de tigeciclina y metodos para preparar las mismas |
| EP1919879A1 (en) * | 2005-08-31 | 2008-05-14 | Wyeth a Corporation of the State of Delaware | 9-aminocarbonylsubstituted derivatives of glycylcyclines |
| AU2007249695A1 (en) | 2006-05-15 | 2007-11-22 | Paratek Pharmaceuticals, Inc. | Methods of regulating expression of genes or of gene products using substituted tetracycline compounds |
| EP2225253B1 (en) | 2007-11-29 | 2012-06-27 | Actelion Pharmaceuticals Ltd. | Phosphonic acid derivates and their use as p2y12 receptor antagonists |
| PT2271348T (pt) | 2008-03-28 | 2018-04-16 | Paratek Pharm Innc | Formulação de comprimido oral de composto de tetraciclina |
| ITMI20080807A1 (it) | 2008-05-05 | 2009-11-06 | Antibioticos Spa | Procedimento per la preparazione di tigeciclina in forma amorfa |
| TW202436282A (zh) | 2008-05-19 | 2024-09-16 | 美商Ｐｒｔｋ Ｓｐｖ２公司 | 四環素化合物之甲苯磺酸鹽及同素異形體 |
| CN105367440A (zh) * | 2008-08-08 | 2016-03-02 | 四相制药公司 | C7-氟取代的四环素化合物 |
| US9073829B2 (en) | 2009-04-30 | 2015-07-07 | President And Fellows Of Harvard College | Synthesis of tetracyclines and intermediates thereto |
| CA2761241C (en) | 2009-05-08 | 2018-02-27 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| WO2011025982A2 (en) | 2009-08-28 | 2011-03-03 | Tetraphase Pharmaceuticals, Inc. | Tetracycline compounds |
| ES2715551T3 (es) | 2010-05-12 | 2019-06-04 | The Medicines Company San Diego Llc | Composiciones de tetraciclina |
| WO2013013504A1 (zh) * | 2011-07-26 | 2013-01-31 | 山东亨利医药科技有限责任公司 | 替加环素衍生物 |
| DK2890673T3 (en) | 2012-08-31 | 2019-03-18 | Tetraphase Pharmaceuticals Inc | tetracycline |
| EP3068370A2 (en) | 2013-11-12 | 2016-09-21 | Galenicum Health S.L. | Stable pharmaceutical compositions |
| DK3529236T3 (da) | 2016-10-19 | 2024-05-13 | Tetraphase Pharmaceuticals Inc | Krystalformer af eravacyclin |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338963A (en) * | 1960-10-28 | 1967-08-29 | American Cyanamid Co | Tetracycline compounds |
| US3579579A (en) * | 1968-04-18 | 1971-05-18 | American Cyanamid Co | Substituted 7- and/or 9-amino-6-demethyl-6-deoxytetracyclines |
-
1992
- 1992-08-21 SG SG1996003437A patent/SG52361A1/en unknown
- 1992-08-21 AT AT92114281T patent/ATE211128T1/de active
- 1992-08-21 ES ES92114281T patent/ES2168254T3/es not_active Expired - Lifetime
- 1992-08-21 PT PT92114281T patent/PT536515E/pt unknown
- 1992-08-21 DE DE69232302A patent/DE69232302D1/de not_active Expired - Lifetime
- 1992-08-21 DE DE69232302T patent/DE69232302T4/de not_active Expired - Lifetime
- 1992-08-21 DK DK92114281T patent/DK0536515T3/da active
- 1992-08-21 EP EP92114281A patent/EP0536515B1/en not_active Expired - Lifetime
- 1992-08-21 DE DE200612000058 patent/DE122006000058I2/de active Active
- 1992-08-21 DE DE1992632302 patent/DE122006000058I1/de active Pending
- 1992-08-27 TW TW081106768A patent/TW275616B/zh not_active IP Right Cessation
- 1992-09-29 MX MX9205532A patent/MX9205532A/es unknown
- 1992-09-30 CZ CZ973093A patent/CZ309397A3/cs not_active IP Right Cessation
- 1992-09-30 SK SK2984-92A patent/SK280837B6/sk not_active IP Right Cessation
- 1992-09-30 CZ CS922984A patent/CZ284159B6/cs not_active IP Right Cessation
- 1992-09-30 HU HU9203110A patent/HU219973B/hu unknown
- 1992-09-30 SK SK1149-99A patent/SK284826B6/sk not_active IP Right Cessation
- 1992-10-01 IL IL10332092A patent/IL103320A/en not_active IP Right Cessation
- 1992-10-01 NZ NZ244585A patent/NZ244585A/en not_active IP Right Cessation
- 1992-10-01 IL IL11959092A patent/IL119590A/xx not_active IP Right Cessation
- 1992-10-02 FI FI924454A patent/FI114911B/fi active Protection Beyond IP Right Term
- 1992-10-02 KR KR1019920018122A patent/KR100269072B1/ko not_active Expired - Lifetime
- 1992-10-02 ZA ZA927607A patent/ZA927607B/xx unknown
- 1992-10-02 CA CA002079692A patent/CA2079692C/en not_active Expired - Lifetime
- 1992-10-02 NO NO923857A patent/NO301472B1/no not_active IP Right Cessation
- 1992-10-02 PL PL92310719A patent/PL176333B1/pl unknown
- 1992-10-02 AU AU26183/92A patent/AU654049B2/en not_active Expired
- 1992-10-02 PL PL92310718A patent/PL175957B1/pl unknown
- 1992-10-02 PL PL92310717A patent/PL172282B1/pl unknown
- 1992-10-02 PL PL92296143A patent/PL173311B1/pl unknown
- 1992-10-03 CN CN92112130A patent/CN1048240C/zh not_active Expired - Lifetime
- 1992-10-05 JP JP28811492A patent/JP3186863B2/ja not_active Expired - Lifetime
-
1995
- 1995-04-28 HU HU95P/P00116P patent/HU211172A9/hu active Protection Beyond IP Right Term
-
1996
- 1996-11-10 IL IL11959096A patent/IL119590A0/xx unknown
-
1997
- 1997-05-12 BR BR1100853-9A patent/BR1100853A/pt active IP Right Grant
-
2004
- 2004-06-25 CL CL200401623A patent/CL2004001623A1/es unknown
-
2006
- 2006-10-11 LU LU91279C patent/LU91279I2/fr unknown
- 2006-10-23 NL NL300244C patent/NL300244I1/nl unknown
- 2006-11-15 NO NO2006015C patent/NO2006015I2/no unknown
-
2017
- 2017-08-01 NO NO2017037C patent/NO2017037I2/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20120930 |