HU188767B - Process for producing 7-/trimethylsilyloxi-carbonyl/-amino-3-cepheme-4-carboxylic acid derivatives - Google Patents
Process for producing 7-/trimethylsilyloxi-carbonyl/-amino-3-cepheme-4-carboxylic acid derivatives Download PDFInfo
- Publication number
- HU188767B HU188767B HU82205A HU20582A HU188767B HU 188767 B HU188767 B HU 188767B HU 82205 A HU82205 A HU 82205A HU 20582 A HU20582 A HU 20582A HU 188767 B HU188767 B HU 188767B
- Authority
- HU
- Hungary
- Prior art keywords
- carboxylic acid
- amino
- carbonyl
- trimethylsilyloxi
- cepheme
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 4
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 abstract description 2
- 229930186147 Cephalosporin Natural products 0.000 abstract description 2
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 abstract description 2
- 229940106164 cephalexin Drugs 0.000 abstract description 2
- 229940124587 cephalosporin Drugs 0.000 abstract description 2
- 150000001780 cephalosporins Chemical class 0.000 abstract description 2
- 230000010933 acylation Effects 0.000 abstract 2
- XBTKPTHTUQVSBJ-NHSZFOGYSA-N (6r)-8-oxo-7-(trimethylsilyloxycarbonylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC=C(C(O)=O)N2C(=O)C(NC(=O)O[Si](C)(C)C)[C@H]21 XBTKPTHTUQVSBJ-NHSZFOGYSA-N 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 229960004841 cefadroxil Drugs 0.000 abstract 1
- NBFNMSULHIODTC-CYJZLJNKSA-N cefadroxil monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=C(O)C=C1 NBFNMSULHIODTC-CYJZLJNKSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 1
- SBUCDZYLTRYMFG-PBFPGSCMSA-N (6r,7r)-7-[[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](N)C=3C=CC(O)=CC=3)[C@H]2SC1 SBUCDZYLTRYMFG-PBFPGSCMSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- CSGFFYNMTALICU-ZWNOBZJWSA-N adipyl-7-aminodesacetoxycephalosporanic acid Natural products CC1=C(N2[C@H](SC1)[C@H](NC(=O)CCCCC(O)=O)C2=O)C(O)=O CSGFFYNMTALICU-ZWNOBZJWSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 229950000042 cefaparole Drugs 0.000 description 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
- 229960001139 cefazolin Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- -1 heterocyclic thiol Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D501/06—Acylation of 7-aminocephalosporanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
A találmány tárgya eljárás új 7-(trimetilszililoxikarbonil - atnino - 3 - ccl'cm - 4 - karbonsav-származékok előállítására, melyek baktériumellenes vegyületek előállításakor köztes vegyületként használhatók.
A szabadalmi irodalomban nagy számú leírást találunk cefalosporinok előállítására egy szililát nukleusz (mint például a 7-amino-cefalosporánsav vagy a 7-amino-dezacetoxi-cefalosporánsav) és egy oldallánc savat kialakító savklorid reakciójával. Ha ez a sav szabad aminocsoportot tartalmaz, úgy azt például protonálással védjük, majd ezt, például a 2-fenil-glicil-klorid-hidrogén-kloridot felhasználjuk a cefalexin előállítására. A nukleusz 4-karboxilcsoportját szililezéssel vagy észterezéssel védhetjük. Ilyen vegyületeket ismertetnek a 3 671 449,3 694 437, 3 741 959, 3 957 773, 3 965 098, 4 051 131 számú amerikai egyesült államokbeli, az 1 073 530 számú nagy-britanniai szabadalmi leírások. A legtöbb esetben a 7-aniino-cefalosporánsav 3-acetoxicsoportját az acilezési reakció előtt heterociklusos tiollal helyettesítik, például a ceforanide (a 4 100 346 számú amerikai egyesült államokbeli szabadalmi leírás és az ebben levő irodalom), a cefatriziiic (3 867 380 számú amerikai egyesült államokbeli szabadalmi leírás), a cefaparole (3 641 021 számú amerikai egyesült államokbeli szabadalmi leírás), a cefazolin (3 516 997 és a 3 819 623 számú amerikai egyesült államokbeli szabadalmi leírás), a cefazaflur (3 828 037 számú amerikai egyesült államokbeli szabadalmi leírás) és más vagy más típusú tiolok esetén, ahogy az a 3 928 336 számú amerikai egyesült államokbeli szabadalmi leírásban látható.
A találmány tárgya eljárás az I általános képletű vegyületek előállítására, ahol az általános képletben
B 1—4 szénatomos alkilcsoport, és
A trimetil-szilil-csoport.
A fenti I általános képletű vegyületek előállítására a találmány értelmében úgy járunk el, hogy egy II általános képletű vegyület oldatához, ahol A és B a fenti, vízmentes nem rcakcíóképes szerves oldószerben, előnyösen metilén-kloridban, 0 °C és 100 °C közötti, előnyösen 0 °C és 20 °C közötti hőmérsékleten vízmentes szén-dioxidot adunk mindaddig, míg a karbonileződési reakció befejeződik.
A továbbiakban példákkal szemléltetjük az eljárást.
7. példa
A 7-(trimetilsziíil)-amíno-3-inctil-3-cefeηι-4-karbonsav-trimetilszilil észter előállítása
100 ml vízmentes metilén-kloridban 10 g (46,68 mmól) 7-amino-3-metil-3-cefem-4-karbonsavat szuszpendálunk, a szuszpenzióhoz 11,8 g (13,7 ml, 108 mmól) triiiietil-klórsziláiit, majd ezt követően csep10 penkéut 30 perc alalt 10,86 g(14,4 ml, 107 mmól) trietil-amint adunk. Két órán át 25 °C-on keveijük a reakcióelegyet. -Ezután mágneses magrezonancia spektroszkópiával vizsgáljuk a szilileződést. A mágneses magrezonancia spektrum szerint a CO2SiMe3 és a 7-NMSiMe3 belső aránya 468 : 462. így az átalakulás 100 %-os. í
2. példa i
A 7-(trimetilszililoxi-karbonil)-amiiio-3-metil-3ccfein-4-karbonsav-trinictilszilil-észler előállítása
Az 1. példában előállított észtert tartalmazó reakcióelegyet 25 °C-on szén-dioxid gázzal kezeljük 4 órán át keverés közben.
Λ karbonilcződési reakciót mágneses magrezonancia spektroszkópiával vizsgáljuk. Az átalakulás 95 %-os.
Claims (1)
- Szabadalmi igénypont 35Eljárás az I általános kcplctű vegyületek előállítására, ahol az általános képletbenB 1—4 szénatomos alkilcsoport, és A trimetil-szilil-csoport, azzal jellemezve, hogy egy II általános képletű vegyület vízmentes néni reakcióképes szerves oldószerrel készült oldatához 0 °C és 100 °C közötti hőmérsékleten addig adunk vízmentes szén-dioxidot, míg a45 reakció teljessé válik, és ahol az általános képletben A és B a fentiekben megadott jelentésű.1 db rajz
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/021,511 US4223135A (en) | 1979-03-19 | 1979-03-19 | Production of cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188767B true HU188767B (en) | 1986-05-28 |
Family
ID=21804643
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU82205A HU188767B (en) | 1979-03-19 | 1979-11-23 | Process for producing 7-/trimethylsilyloxi-carbonyl/-amino-3-cepheme-4-carboxylic acid derivatives |
| HU79BI597A HU180687B (en) | 1979-03-19 | 1979-11-23 | Process for preparing 7-acyl-amido-ceph-3-eme-4-carboxylic acid derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79BI597A HU180687B (en) | 1979-03-19 | 1979-11-23 | Process for preparing 7-acyl-amido-ceph-3-eme-4-carboxylic acid derivatives |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4223135A (hu) |
| JP (2) | JPS55129290A (hu) |
| AR (1) | AR231143A1 (hu) |
| CA (1) | CA1130278A (hu) |
| CH (1) | CH642969A5 (hu) |
| DE (1) | DE2951477A1 (hu) |
| DK (2) | DK161522C (hu) |
| ES (2) | ES8102577A1 (hu) |
| FI (1) | FI74709C (hu) |
| FR (1) | FR2467213A1 (hu) |
| GB (1) | GB2044248B (hu) |
| GR (1) | GR82675B (hu) |
| HU (2) | HU188767B (hu) |
| IE (1) | IE49212B1 (hu) |
| IL (1) | IL58396A (hu) |
| IT (1) | IT1164907B (hu) |
| NL (1) | NL7907551A (hu) |
| NO (1) | NO158137C (hu) |
| PH (1) | PH15449A (hu) |
| SE (2) | SE445554B (hu) |
| ZA (1) | ZA795132B (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2069482B (en) * | 1980-02-14 | 1984-04-04 | Gist Brocades Nv | Process for the preparation of 3'-bromosubstituted deacetoxycephalosporanic acid sulphoxide derivatives |
| AT381315B (de) * | 1984-11-23 | 1986-09-25 | Biochemie Gmbh | Verfahren zur herstellung von cephalosporinderivaten |
| US4868294A (en) * | 1986-07-11 | 1989-09-19 | Bristol-Myers Company | Process for preparing cephalosporin intermediates |
| US5142043A (en) * | 1990-05-10 | 1992-08-25 | Biocraft Laboratories, Inc. | Process for preparing cephalexin monohydrate |
| US20070111980A1 (en) * | 2004-07-16 | 2007-05-17 | Bandi Parthasaradhi Reddy | Process for preparing pure cephalosporine intermediates |
| US7207857B2 (en) * | 2005-09-20 | 2007-04-24 | Patent Category Corp. | Floating assemblies |
| CN102351884B (zh) * | 2006-05-19 | 2015-06-17 | 中化帝斯曼制药有限公司荷兰公司 | 一种用于结晶头孢羟氨苄的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE311519B (hu) | 1962-12-14 | 1969-06-16 | Astra Ab | |
| CH527215A (de) * | 1967-04-15 | 1972-08-31 | Fujisawa Pharmaceutical Co | Verfahren zur Herstellung von 3,7-disubstituierten Cephalosporinderivaten |
| US3819623A (en) * | 1968-04-12 | 1974-06-25 | Fujisawa Pharmaceutical Co | 3,7-disubstituted cephalosporin compounds |
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| GB1332306A (en) * | 1969-12-23 | 1973-10-03 | Glaxo Lab Ltd | Antibiotics |
| US3694437A (en) * | 1970-08-19 | 1972-09-26 | Lilly Co Eli | Process for preparing cephalosporin compounds |
| US3671449A (en) * | 1970-08-19 | 1972-06-20 | Lilly Co Eli | Cephalosporin compositions |
| US3867380A (en) * | 1971-02-18 | 1975-02-18 | Smithkline Corp | 3-Heterocyclic thiomethylcephalosporins |
| US3828037A (en) * | 1972-07-20 | 1974-08-06 | Smithkline Corp | Trifluoromethylmercaptoacetamidocephalosporins |
| US4051131A (en) * | 1972-11-29 | 1977-09-27 | American Home Products Corporation (Del.) | Intermediates for preparing cephalosporins |
| US3965098A (en) * | 1972-11-29 | 1976-06-22 | American Home Products Corporation | Intermediates for preparing cephalosporins and methods of production |
| US3928336A (en) * | 1974-07-29 | 1975-12-23 | Bristol Myers Co | 7-{8 D-({60 -amino{60 -phenyl-, 2-thienyl- and 3-thienyl-acetamido){9 -3-(3-methyl-1,2,5-oxadiazol-4-yl)carbonylthiomethyl-3-cephem-4-carboxylic acids |
| JPS525787A (en) * | 1975-06-27 | 1977-01-17 | Bristol Myers Co | Antiibacterial agent |
-
1979
- 1979-03-19 US US06/021,511 patent/US4223135A/en not_active Expired - Lifetime
- 1979-09-24 SE SE7907902A patent/SE445554B/sv not_active IP Right Cessation
- 1979-09-26 FI FI792995A patent/FI74709C/fi not_active IP Right Cessation
- 1979-09-26 CA CA336,416A patent/CA1130278A/en not_active Expired
- 1979-09-27 NO NO79793103A patent/NO158137C/no unknown
- 1979-09-27 ZA ZA00795132A patent/ZA795132B/xx unknown
- 1979-09-27 DK DK406579A patent/DK161522C/da not_active IP Right Cessation
- 1979-10-03 PH PH23101A patent/PH15449A/en unknown
- 1979-10-04 IL IL7958396A patent/IL58396A/xx unknown
- 1979-10-05 AR AR278381A patent/AR231143A1/es active Active
- 1979-10-10 IT IT50520/79A patent/IT1164907B/it active
- 1979-10-11 NL NL7907551A patent/NL7907551A/nl not_active Application Discontinuation
- 1979-10-12 GB GB7935449A patent/GB2044248B/en not_active Expired
- 1979-10-25 CH CH960579A patent/CH642969A5/de not_active IP Right Cessation
- 1979-11-19 IE IE2211/79A patent/IE49212B1/en not_active IP Right Cessation
- 1979-11-21 JP JP15129379A patent/JPS55129290A/ja active Granted
- 1979-11-23 HU HU82205A patent/HU188767B/hu not_active IP Right Cessation
- 1979-11-23 HU HU79BI597A patent/HU180687B/hu not_active IP Right Cessation
- 1979-11-29 ES ES486463A patent/ES8102577A1/es not_active Expired
- 1979-12-05 GR GR60691A patent/GR82675B/el unknown
- 1979-12-20 DE DE19792951477 patent/DE2951477A1/de active Granted
-
1980
- 1980-03-14 FR FR8005714A patent/FR2467213A1/fr active Granted
- 1980-06-30 ES ES492956A patent/ES492956A0/es active Granted
-
1984
- 1984-09-20 SE SE8404730A patent/SE458608B/sv not_active IP Right Cessation
-
1986
- 1986-11-21 JP JP61278500A patent/JPS62161789A/ja active Granted
-
1991
- 1991-01-18 DK DK008891A patent/DK164365C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |