CA2591818A1 - Process for the preparation of aminoalcohol derivatives and their further conversion to (1s, 4r)- or (1r, 4s)-1-amino-4-(hydroxymethyl)-2-cyclopentene - Google Patents
Process for the preparation of aminoalcohol derivatives and their further conversion to (1s, 4r)- or (1r, 4s)-1-amino-4-(hydroxymethyl)-2-cyclopentene Download PDFInfo
- Publication number
- CA2591818A1 CA2591818A1 CA002591818A CA2591818A CA2591818A1 CA 2591818 A1 CA2591818 A1 CA 2591818A1 CA 002591818 A CA002591818 A CA 002591818A CA 2591818 A CA2591818 A CA 2591818A CA 2591818 A1 CA2591818 A1 CA 2591818A1
- Authority
- CA
- Canada
- Prior art keywords
- hydroxymethyl
- amino
- formula
- cyclopentene
- preparation
- 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.)
- Granted
Links
- UXKZFJDNFBNQHE-RITPCOANSA-N [(1s,4r)-4-aminocyclopent-2-en-1-yl]methanol Chemical compound N[C@@H]1C[C@H](CO)C=C1 UXKZFJDNFBNQHE-RITPCOANSA-N 0.000 title claims abstract 6
- 238000000034 method Methods 0.000 title claims abstract 6
- 150000001414 amino alcohols Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 102000004157 Hydrolases Human genes 0.000 claims 2
- 108090000604 Hydrolases Proteins 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 102000004882 Lipase Human genes 0.000 claims 1
- 108090001060 Lipase Proteins 0.000 claims 1
- 239000004367 Lipase Substances 0.000 claims 1
- UXKZFJDNFBNQHE-NTSWFWBYSA-N [(1r,4s)-4-aminocyclopent-2-en-1-yl]methanol Chemical class N[C@H]1C[C@@H](CO)C=C1 UXKZFJDNFBNQHE-NTSWFWBYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 235000019421 lipase Nutrition 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Abstract
The invention relates to a novel process for the preparation of A process for the preparation of (1S,4R)- or (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene of formula V or VI, (see figure I) or a salt thereof or of a(1S,4R)- or (1R,4S)-1-amino-4--(hydroxymethyl)-2-cyclopentene derivative of general formula VII or VIII, (see figure II) or a salt thereof, wherein X and Y are identical or different and are an acyl group or H, with the exception of X = Y = H, comprising a racemate resolution of a racemic aminoalcohol of formula I, (see figure III) by biotechnological means using a hydrolase in the presence of an acrylating agent.
Claims (3)
1. A process for the preparation of (1S,4R)- or (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene of formula V or VI, or a salt thereof or of a(1S,4R)- or (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene derivative of general formula VII or VIII, or a salt thereof, wherein X and Y are identical or different and are an acyl group or H, with the exception of X = Y = H, comprising a racemate resolution of a racemic aminoalcohol of formula I, by biotechnological means using a hydrolase in the presence of an acrylating agent.
2. A process according to Claim 1, wherein the racemate resolution is carried out using a lipase.
3. A process for the preparation of an (1R,4S)- or (1S,4R)-1-amino-4-(hydroxymethyl)-2-cyclopentene derivative of general formula IX or X, wherein R is C1-4-alkyl, C1-4-alkoxy, aryl or aryloxy, comprising, in a first stage, reducing (~)-2-azabicyclo[2.2.1]hept-5-en-3-one of formula II, in the form of a racemate or one of its optically active isomers with a metal hydride, to form a racemic aminoalcohol of formula I, which, in a second stage, is converted by biotechnological means using a hydrolase in the presence of an acylating agent, into (1S,4R)- or (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula V or VI, which is acylated to give a product of formula IX or X.
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2739/97 | 1997-11-27 | ||
| CH273997 | 1997-11-27 | ||
| CH2781/97 | 1997-12-03 | ||
| CH278197 | 1997-12-03 | ||
| CH0133/98 | 1998-01-21 | ||
| CH13398 | 1998-01-21 | ||
| CH72398 | 1998-03-27 | ||
| CH0723/98 | 1998-03-27 | ||
| EP98118895 | 1998-10-07 | ||
| EP98118895.6 | 1998-10-07 | ||
| CA002254693A CA2254693C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1r,4s)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino)-2-cyclopentenyl-1-methanol |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002254693A Division CA2254693C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1r,4s)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino)-2-cyclopentenyl-1-methanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2591818A1 true CA2591818A1 (en) | 1999-05-27 |
| CA2591818C CA2591818C (en) | 2010-08-03 |
Family
ID=27508776
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2591818A Expired - Fee Related CA2591818C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of optically active aminoalcohols |
| CA2591566A Expired - Fee Related CA2591566C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of an aminoalcohol |
| CA002591571A Abandoned CA2591571A1 (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1s,4r)- or (1r,4s)-1-amino-4-(hydroxymethyl)-2-cyclopentene |
| CA002254693A Expired - Fee Related CA2254693C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1r,4s)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino)-2-cyclopentenyl-1-methanol |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2591566A Expired - Fee Related CA2591566C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of an aminoalcohol |
| CA002591571A Abandoned CA2591571A1 (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1s,4r)- or (1r,4s)-1-amino-4-(hydroxymethyl)-2-cyclopentene |
| CA002254693A Expired - Fee Related CA2254693C (en) | 1997-11-27 | 1998-11-25 | Process for the preparation of aminoalcohol derivatives and their further conversion to (1r,4s)-4-((2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino)-2-cyclopentenyl-1-methanol |
Country Status (18)
| Country | Link |
|---|---|
| US (5) | US6723868B1 (en) |
| EP (5) | EP1418170B1 (en) |
| JP (4) | JP4372873B2 (en) |
| KR (4) | KR100615370B1 (en) |
| CN (4) | CN1323057C (en) |
| AT (4) | ATE404689T1 (en) |
| CA (4) | CA2591818C (en) |
| CZ (4) | CZ298102B6 (en) |
| DE (4) | DE59814270D1 (en) |
| DK (3) | DK1657243T3 (en) |
| ES (3) | ES2215264T3 (en) |
| HK (2) | HK1070103A1 (en) |
| HU (3) | HU225895B1 (en) |
| IL (5) | IL142623A (en) |
| NO (4) | NO318697B1 (en) |
| PL (2) | PL200436B1 (en) |
| PT (4) | PT1508565E (en) |
| SK (4) | SK284416B6 (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4633934B2 (en) | 1998-12-23 | 2011-02-16 | ロンザ アーゲー | Process for producing optically active 1-amino-4- (hydroxylmethyl) -cyclopent-2-ene derivative |
| US8042740B2 (en) * | 2000-11-24 | 2011-10-25 | Metrologic Instruments, Inc. | Method of reading bar code symbols on objects at a point-of-sale station by passing said objects through a complex of stationary coplanar illumination and imaging planes projected into a 3D imaging volume |
| ES2278061T3 (en) * | 2001-09-25 | 2007-08-01 | F. Hoffmann-La Roche Ag | ENZYMATIC PROCESS FOR PREPARATION OF ACID 2-AMINO-3- (2-AMINO-PHENYL SULFANIL) -PROPIONIC SUBSTITUTED. |
| KR100684772B1 (en) | 2004-12-08 | 2007-02-22 | 주식회사농심 | Food having feel of pudding using glutinous rice and processing method for the same |
| US8805134B1 (en) | 2012-02-17 | 2014-08-12 | Soraa Laser Diode, Inc. | Methods and apparatus for photonic integration in non-polar and semi-polar oriented wave-guided optical devices |
| US9250044B1 (en) | 2009-05-29 | 2016-02-02 | Soraa Laser Diode, Inc. | Gallium and nitrogen containing laser diode dazzling devices and methods of use |
| US8945066B2 (en) | 2009-11-06 | 2015-02-03 | Crisi Medical Systems, Inc. | Medication injection site and data collection system |
| CN102603652A (en) * | 2011-12-27 | 2012-07-25 | 河南师范大学 | 5-formacylpyrimidine carbocyclic nucleoside and preparation method thereof |
| CN102719512B (en) * | 2012-06-21 | 2014-06-11 | 浙江工业大学 | Preparation method for R-2-(4- hydroxyphenoxy) propionate |
| CN104098478B (en) * | 2013-04-08 | 2017-05-17 | 安徽贝克联合制药有限公司 | Aminoalcohol resolution method |
| WO2016067182A2 (en) * | 2014-10-27 | 2016-05-06 | Granules India Limited | Process for the preparation of amino alcohol derivatives or salts thereof |
| CN104974051A (en) * | 2015-06-30 | 2015-10-14 | 苏州开元民生科技股份有限公司 | Synthetic method for (1S,4R)-cis-4-amino-2-cyclopentene-1-methanol hydrochloride |
| CN106220515A (en) * | 2016-08-12 | 2016-12-14 | 郸城巨鑫生物科技有限公司 | A kind of synthetic method of (1R, 4S) 1 amino 4 methylol 2 cyclopentenes hydrochlorate |
| EP3523280A1 (en) * | 2016-10-06 | 2019-08-14 | Janssen Pharmaceutica NV | Processes and intermediates for preparing a btk inhibitor |
| US11421843B2 (en) | 2018-12-21 | 2022-08-23 | Kyocera Sld Laser, Inc. | Fiber-delivered laser-induced dynamic light system |
| US11239637B2 (en) | 2018-12-21 | 2022-02-01 | Kyocera Sld Laser, Inc. | Fiber delivered laser induced white light system |
| CN109735582B (en) * | 2018-12-24 | 2022-06-21 | 浙江工业大学 | Method for synthesizing cyclohexanol beta-amino alcohol derivatives on line by lipase catalysis |
| US11884202B2 (en) | 2019-01-18 | 2024-01-30 | Kyocera Sld Laser, Inc. | Laser-based fiber-coupled white light system |
| CN116730856A (en) * | 2023-06-19 | 2023-09-12 | 浙江竹子制药有限公司 | Synthesis method of tranexamic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2534533A (en) | 1945-11-05 | 1950-12-19 | Hermann I Schlesinger | Methods of preparing alkali metal borohydrides |
| DE947702C (en) | 1954-07-16 | 1956-08-23 | Metallgesellschaft Ag | Process for the production of boron-containing metal hydrides |
| US4138562A (en) | 1977-02-09 | 1979-02-06 | The Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine nucleosides and method of preparation |
| US4268672A (en) * | 1977-02-09 | 1981-05-19 | The Regents Of The University Of Minnesota | Adenosine deaminase resistant antiviral purine nucleosides and method of preparation |
| US4916224A (en) * | 1988-01-20 | 1990-04-10 | Regents Of The University Of Minnesota | Dideoxycarbocyclic nucleosides |
| GB8815265D0 (en) * | 1988-06-27 | 1988-08-03 | Wellcome Found | Therapeutic nucleosides |
| AU626314B2 (en) * | 1988-09-09 | 1992-07-30 | Ferag Ag | Method and means for tabloid further processing |
| MY104575A (en) * | 1989-12-22 | 1994-04-30 | The Wellcome Foundation Ltd | Therapeutic nucleosides. |
| JPH0484896A (en) * | 1990-07-26 | 1992-03-18 | Kyowa Hakko Kogyo Co Ltd | Production of optically active isoindoline-1-one derivative |
| US5200527A (en) | 1991-04-08 | 1993-04-06 | Lonza Ltd. | Process for the production of 2-azabicyclo [2.2.1] hept-5-en-3-one |
| FR2676042B1 (en) | 1991-05-02 | 1993-07-23 | Commissariat Energie Atomique | PROCESS FOR THE PREPARATION OF AN ALKALI METAL BOROHYDRIDE SUCH AS LITHIUM BOROHYDRIDE. |
| GB9204015D0 (en) * | 1992-02-25 | 1992-04-08 | Wellcome Found | Therapeutic nucleosides |
| GB9402161D0 (en) * | 1994-02-04 | 1994-03-30 | Wellcome Found | Chloropyrimidine intermediates |
| GB9417249D0 (en) * | 1994-08-26 | 1994-10-19 | Wellcome Found | A novel salt |
| JPH09124564A (en) * | 1995-11-06 | 1997-05-13 | Nikko Rika Kk | Optically active compound mixture and its production |
| JP3974656B2 (en) * | 1995-11-16 | 2007-09-12 | ジー．ディー．サール アンド カンパニー | N-protected / N-substituted-beta-aminohydroxysulfonate |
| ATE283348T1 (en) * | 1996-05-30 | 2004-12-15 | Lonza Ag | METHOD FOR PRODUCING AMINO ALCOHOLS AND DERIVATIVES THEREOF |
| SK285228B6 (en) * | 1997-05-13 | 2006-09-07 | Lonza Ag | Process for the preparation of a racemic or optically active 4-(hydroxymethyl)-2-cyclopentene derivative and racemic N-butyryl-1-amino-4-(hydroxymethyl)-2-cyclopentene |
| GB9721780D0 (en) * | 1997-10-14 | 1997-12-10 | Glaxo Group Ltd | Process for the synthesis of chloropurine intermediates |
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1998
- 1998-11-23 CZ CZ0381798A patent/CZ298102B6/en not_active IP Right Cessation
- 1998-11-23 SK SK1615-98A patent/SK284416B6/en not_active IP Right Cessation
- 1998-11-23 SK SK402-2004A patent/SK284595B6/en not_active IP Right Cessation
- 1998-11-23 CZ CZ20070123A patent/CZ298144B6/en not_active IP Right Cessation
- 1998-11-23 CZ CZ20070124A patent/CZ299083B6/en not_active IP Right Cessation
- 1998-11-23 SK SK401-2004A patent/SK284594B6/en not_active IP Right Cessation
- 1998-11-23 SK SK403-2004A patent/SK284596B6/en not_active IP Right Cessation
- 1998-11-23 CZ CZ20070122A patent/CZ298913B6/en not_active IP Right Cessation
- 1998-11-24 AT AT04027540T patent/ATE404689T1/en active
- 1998-11-24 PT PT04027540T patent/PT1508565E/en unknown
- 1998-11-24 KR KR1019980050483A patent/KR100615370B1/en not_active IP Right Cessation
- 1998-11-24 DE DE59814270T patent/DE59814270D1/en not_active Expired - Lifetime
- 1998-11-24 DK DK06002571.5T patent/DK1657243T3/en active
- 1998-11-24 ES ES98122293T patent/ES2215264T3/en not_active Expired - Lifetime
- 1998-11-24 AT AT06002571T patent/ATE478073T1/en active
- 1998-11-24 AT AT04002913T patent/ATE328863T1/en active
- 1998-11-24 DE DE59813589T patent/DE59813589D1/en not_active Expired - Lifetime
- 1998-11-24 DK DK04002913T patent/DK1418170T3/en active
- 1998-11-24 AT AT98122293T patent/ATE259345T1/en active
- 1998-11-24 DK DK98122293T patent/DK0926131T3/en active
- 1998-11-24 EP EP04002913A patent/EP1418170B1/en not_active Expired - Lifetime
- 1998-11-24 EP EP08161021A patent/EP1982985A3/en not_active Withdrawn
- 1998-11-24 DE DE59814466T patent/DE59814466D1/en not_active Expired - Lifetime
- 1998-11-24 ES ES04002913T patent/ES2270192T3/en not_active Expired - Lifetime
- 1998-11-24 EP EP04027540A patent/EP1508565B1/en not_active Expired - Lifetime
- 1998-11-24 PT PT04002913T patent/PT1418170E/en unknown
- 1998-11-24 PT PT98122293T patent/PT926131E/en unknown
- 1998-11-24 EP EP06002571A patent/EP1657243B1/en not_active Expired - Lifetime
- 1998-11-24 PT PT06002571T patent/PT1657243E/en unknown
- 1998-11-24 DE DE59810751T patent/DE59810751D1/en not_active Expired - Lifetime
- 1998-11-24 ES ES04027540T patent/ES2312906T3/en not_active Expired - Lifetime
- 1998-11-24 EP EP98122293A patent/EP0926131B1/en not_active Expired - Lifetime
- 1998-11-24 US US09/198,427 patent/US6723868B1/en not_active Expired - Fee Related
- 1998-11-25 CA CA2591818A patent/CA2591818C/en not_active Expired - Fee Related
- 1998-11-25 CA CA2591566A patent/CA2591566C/en not_active Expired - Fee Related
- 1998-11-25 CA CA002591571A patent/CA2591571A1/en not_active Abandoned
- 1998-11-25 CA CA002254693A patent/CA2254693C/en not_active Expired - Fee Related
- 1998-11-26 IL IL14262398A patent/IL142623A/en not_active IP Right Cessation
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