DK168217B1 - Fremgangsmåde til fremstilling af 1-dethia-1-oxacepham- og cephalosporinforbindelser - Google Patents

Fremgangsmåde til fremstilling af 1-dethia-1-oxacepham- og cephalosporinforbindelser Download PDF

Info

Publication number: DK168217B1
Authority: DK; Denmark
Prior art keywords: cob; dethia; mixture; oxacepham; preparation
Prior art date: 1977-02-15

Application number

DK060678A

Other languages

Danish (da)

English (en)

Other versions

DK60678A (da

Inventor

Mitsuru Yoshioka

Shoichiro Uyeo

Yoshio Hamashima

Ikuo Kikkawa

Teruji Tsuji

Wataru Nagata

Original Assignee

Shionogi & Co

Priority date (The priority date 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 date listed.)

1977-02-15

Filing date

1978-02-10

Publication date

1994-02-28

1977-02-15 Priority claimed from JP1581377A external-priority patent/JPS53101391A/ja

1977-06-06 Priority claimed from JP52067025A external-priority patent/JPS6040438B2/ja

1978-02-10 Application filed by Shionogi & Co filed Critical Shionogi & Co

1978-08-16 Publication of DK60678A publication Critical patent/DK60678A/da

1994-02-28 Application granted granted Critical

1994-02-28 Publication of DK168217B1 publication Critical patent/DK168217B1/da

Links

-1 Cephalosporin Compounds Chemical class 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 8
229940124587 cephalosporin Drugs 0.000 title claims description 6
229930186147 Cephalosporin Natural products 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
239000000203 mixture Substances 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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238000006243 chemical reaction Methods 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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239000000047 product Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
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230000015572 biosynthetic process Effects 0.000 description 6
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102100035861 Cytosolic 5'-nucleotidase 1A Human genes 0.000 description 2
101000802744 Homo sapiens Cytosolic 5'-nucleotidase 1A Proteins 0.000 description 2
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 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
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150000001298 alcohols Chemical class 0.000 description 2
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238000007796 conventional method Methods 0.000 description 2
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235000010755 mineral Nutrition 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical group C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
101150083668 tfdD gene Proteins 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)

DK060678A 1977-02-15 1978-02-10 Fremgangsmåde til fremstilling af 1-dethia-1-oxacepham- og cephalosporinforbindelser DK168217B1 (da)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP1581377A JPS53101391A (en)	1977-02-15	1977-02-15	1-oxadithiacephem compounds
JP1581377		1977-02-15
JP6702577		1977-06-06
JP52067025A JPS6040438B2 (ja)	1977-06-06	1977-06-06	１−オキサデチアセフアロスポリンの製法

Publications (2)

Publication Number	Publication Date
DK60678A DK60678A (da)	1978-08-16
DK168217B1 true DK168217B1 (da)	1994-02-28

Family

ID=26352032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK060678A DK168217B1 (da)	1977-02-15	1978-02-10	Fremgangsmåde til fremstilling af 1-dethia-1-oxacepham- og cephalosporinforbindelser

Country Status (26)

Country	Link
US (1)	US4366316A (es)
AR (1)	AR227867A1 (es)
AU (1)	AU514377B2 (es)
BG (4)	BG32854A3 (es)
CA (1)	CA1099715A (es)
CH (1)	CH636618A5 (es)
DE (1)	DE2806457A1 (es)
DK (1)	DK168217B1 (es)
ES (4)	ES466949A1 (es)
FI (1)	FI68401C (es)
FR (1)	FR2380284A1 (es)
GB (1)	GB1557552A (es)
GR (1)	GR69965B (es)
HU (1)	HU177897B (es)
IE (1)	IE47711B1 (es)
IL (1)	IL54044A (es)
MX (1)	MX5479E (es)
NL (1)	NL191891C (es)
NO (1)	NO162343C (es)
NZ (1)	NZ186437A (es)
PH (4)	PH15515A (es)
PL (1)	PL114451B1 (es)
PT (1)	PT67648B (es)
RO (3)	RO78545A (es)
SE (1)	SE443144B (es)
YU (2)	YU41307B (es)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4259485A (en) *	1979-04-24	1981-03-31	Eli Lilly And Company	Crystallization process
US4304774A (en)	1980-09-17	1981-12-08	Eli Lilly And Company	Bis-tetrazolmethyl substituted β-lactam antibiotics
JPS58185588A (ja) *	1982-04-23	1983-10-29	Shionogi & Co Ltd	空気酸化によるハロメチル化合物の酸化方法および酸化生成物
DE3231060A1 (de) *	1982-08-20	1984-02-23	Bayer Ag, 5090 Leverkusen	In 6-stellung unsubstituierte 7-oxo-4-oxa-diazabicyclo-(3.2.0)-hept-2-en derivate, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte zur synthese von ss-lactamantibiotika
US4458071A (en) *	1982-11-16	1984-07-03	Eli Lilly And Company	Process for 1-oxa-β-lactams
US4652651A (en) *	1983-05-31	1987-03-24	Hoffmann-La Roche Inc.	Process for the manufacture of 1-sulpho-2-oxoazetidine carboxylic acid intermediates via catalytic ester cleavage
DE3404906A1 (de) *	1984-02-11	1985-08-14	Bayer Ag, 5090 Leverkusen	1-oxadethiacephalosporinderivate sowie verfahren zu ihrer herstellung
US4645769A (en) *	1985-03-01	1987-02-24	Merck & Co., Inc.	1-oxa-1-dethia-cephalosporin compounds and antibacterial agent comprising the same
CN102286004A (zh) *	2011-09-21	2011-12-21	河北九派制药有限公司	拉氧头孢钠中间体的制备方法
CN103254215B (zh) *	2013-05-24	2015-06-03	浙江东邦药业有限公司	一种烯丙基氯代氧头孢化合物的制备方法
CN106749335B (zh) *	2016-11-29	2019-02-12	浙江新和成股份有限公司	一种卤代氧头孢类中间体的制备方法和应用
CN107118224B (zh) *	2017-06-15	2019-09-17	浙江新和成股份有限公司	一种氧头孢母核中间体的制备方法、其溶剂化合物及其制备方法
CN114315858B (zh) *	2022-01-11	2023-05-09	深圳市立国药物研究有限公司	一种氟氧头孢中间体的合成方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL178005C (nl) *	1972-11-06	1986-01-02	Merck & Co Inc	Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum.
GB1510794A (en) *	1974-08-06	1978-05-17	Univ Kingston	1-oxacephems and intermediates therefor
FR2361114A1 (fr) *	1975-11-12	1978-03-10	Shionogi & Co	Procede de preparation d'analogues de cephalosporine a propriete antibacterienne et nouveaux produits ainsi obtenus
US4150156A (en) *	1975-11-21	1979-04-17	Merck & Co., Inc.	7-(Substituted methyl)-3-(substituted thio)-cephalosporins, derivatives and pharmaceutical compositions containing them
CA1085392A (en) *	1976-03-25	1980-09-09	Masayuki Narisada	Arylmalonamido-1-oxadethiacephalosporins
GR61146B (en) *	1976-03-25	1978-09-27	Shionogi & Co	Preparation process of 1-oxadethiacephalosporins analogues
US4079179A (en) *	1976-03-30	1978-03-14	Merck & Co., Inc.	6-Loweralkoxy or loweralkylthio-3-cephem-4-carboxylic acids
JPS607635B2 (ja) *	1976-04-27	1985-02-26	塩野義製薬株式会社	オキサゾリジン化合物
US4044002A (en) *	1976-06-09	1977-08-23	Eli Lilly And Company	Reduction process for cephalosporin sulfoxides
JPS609514B2 (ja) *	1976-08-05	1985-03-11	塩野義製薬株式会社	７−アミノ−３′−ノルセファロスポラン酸類
CA1090806A (en) *	1977-01-10	1980-12-02	Mitsuru Yoshioka	Oxazolines
JPS5398951A (en) *	1977-02-08	1978-08-29	Shionogi & Co Ltd	Azetidinone derivatives and process for their preparation
US4207782A (en) *	1978-07-31	1980-06-17	Brunswick Corporation	Multi-conductor insulation stripping apparatus

1978
- 1978-02-09 AU AU33164/78A patent/AU514377B2/en not_active Expired
- 1978-02-09 GB GB5339/78A patent/GB1557552A/en not_active Expired
- 1978-02-10 NZ NZ186437A patent/NZ186437A/xx unknown
- 1978-02-10 IE IE298/78A patent/IE47711B1/en not_active IP Right Cessation
- 1978-02-10 DK DK060678A patent/DK168217B1/da not_active IP Right Cessation
- 1978-02-10 CA CA296,776A patent/CA1099715A/en not_active Expired
- 1978-02-13 PT PT67648A patent/PT67648B/pt unknown
- 1978-02-13 IL IL54044A patent/IL54044A/xx unknown
- 1978-02-14 ES ES466949A patent/ES466949A1/es not_active Expired
- 1978-02-14 RO RO78100612A patent/RO78545A/ro unknown
- 1978-02-14 GR GR55452A patent/GR69965B/el unknown
- 1978-02-14 PL PL1978204616A patent/PL114451B1/pl unknown
- 1978-02-14 RO RO78100613A patent/RO79398A/ro unknown
- 1978-02-14 FR FR7804162A patent/FR2380284A1/fr active Granted
- 1978-02-14 YU YU335/78A patent/YU41307B/xx unknown
- 1978-02-14 BG BG040118A patent/BG32854A3/xx unknown
- 1978-02-14 BG BG038671A patent/BG32853A3/xx unknown
- 1978-02-14 MX MX786846U patent/MX5479E/es unknown
- 1978-02-14 RO RO78100614A patent/RO79886A/ro unknown
- 1978-02-14 HU HU78SI1619A patent/HU177897B/hu unknown
- 1978-02-14 FI FI780474A patent/FI68401C/fi not_active IP Right Cessation
- 1978-02-14 NO NO780508A patent/NO162343C/no unknown
- 1978-02-14 SE SE7801697A patent/SE443144B/sv not_active IP Right Cessation
- 1978-02-14 BG BG040119A patent/BG32855A3/bg unknown
- 1978-02-15 PH PH20789A patent/PH15515A/en unknown
- 1978-02-15 NL NL7801708A patent/NL191891C/xx not_active IP Right Cessation
- 1978-02-15 DE DE19782806457 patent/DE2806457A1/de active Granted
- 1978-02-15 CH CH167278A patent/CH636618A5/de not_active IP Right Cessation
- 1978-06-16 BG BG040120A patent/BG32856A3/bg unknown
- 1978-11-16 ES ES78475142A patent/ES475142A1/es not_active Expired
- 1978-11-16 ES ES78475140A patent/ES475140A1/es not_active Expired
- 1978-11-16 ES ES475141A patent/ES475141A1/es not_active Expired
1979
- 1979-12-20 PH PH23440A patent/PH15291A/en unknown
- 1979-12-20 PH PH23438A patent/PH15294A/en unknown
- 1979-12-20 PH PH23439A patent/PH15513A/en unknown
1981
- 1981-11-18 US US06/322,662 patent/US4366316A/en not_active Expired - Lifetime
1982
- 1982-01-01 AR AR22786782D patent/AR227867A1/es active
1983
- 1983-03-07 YU YU548/83A patent/YU42073B/xx unknown

Also Published As

Publication number	Publication date
PH15291A (en)	1982-11-09
IE47711B1 (en)	1984-05-30
AU514377B2 (en)	1981-02-05
IL54044A0 (en)	1978-04-30
BG32854A3 (bg)	1982-10-15
CH636618A5 (en)	1983-06-15
DK60678A (da)	1978-08-16
NL191891C (nl)	1996-10-04
RO79886A (ro)	1982-10-11
AU3316478A (en)	1979-08-16
SE7801697L (sv)	1978-08-16
PL204616A1 (pl)	1979-04-23
PT67648A (en)	1978-03-01
BG32856A3 (bg)	1982-10-15
NO162343B (no)	1989-09-04
NL191891B (nl)	1996-06-03
FI68401C (fi)	1985-09-10
YU54883A (en)	1984-02-29
MX5479E (es)	1983-08-19
BG32855A3 (bg)	1982-10-15
NZ186437A (en)	1980-09-12
ES475140A1 (es)	1980-01-01
DE2806457C2 (es)	1993-07-01
FI68401B (fi)	1985-05-31
SE443144B (sv)	1986-02-17
FI780474A7 (fi)	1978-08-16
IE780298L (en)	1978-08-15
HU177897B (en)	1982-01-28
PT67648B (en)	1979-07-18
RO78545A (ro)	1982-03-24
GR69965B (es)	1982-07-22
GB1557552A (en)	1979-12-12
BG32853A3 (bg)	1982-10-15
ES475142A1 (es)	1980-01-01
PL114451B1 (en)	1981-01-31
YU42073B (en)	1988-04-30
ES466949A1 (es)	1979-10-01
ES475141A1 (es)	1979-06-01
CA1099715A (en)	1981-04-21
RO79398A (ro)	1982-06-25
YU41307B (en)	1987-02-28
NO780508L (no)	1978-08-16
AR227867A1 (es)	1982-12-30
US4366316A (en)	1982-12-28
FR2380284A1 (fr)	1978-09-08
FR2380284B1 (es)	1980-05-16
NO162343C (no)	1989-12-13
IL54044A (en)	1981-07-31
YU33578A (en)	1983-06-30
PH15294A (en)	1982-11-09
PH15513A (en)	1983-02-03
PH15515A (en)	1983-02-03
DE2806457A1 (de)	1978-08-17
NL7801708A (nl)	1978-08-17

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DK145044B (da)	1982-08-09	Fremgangsmaade til fremstilling af 7-aminodesacetoxycephalosporanestere og sulfonsyresalte deraf
JPH02178287A (ja)	1990-07-11	光学活性ベンゾオキサジン及びベンゾチアジン及びそれらの立体選択的製造方法
EA002547B1 (ru)	2002-06-27	Способ селективного эпоксидирования для получения лекарственных соединений
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KR970005896B1 (ko)	1997-04-21	신규 세팔로스포린계 항생제 및 그의 제조방법
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JP2004502778A (ja)	2004-01-29	新規なセファロスポリン化合物およびその製造方法
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JPS6123198B2 (es)	1986-06-04
BE897064A (fr)	1983-10-17	Procede de preparation de composes de 3-methylene cepham
HU181761B (en)	1983-11-28	Process for preparing crystalline 3-hydroxy-cefem-carboxylic acid solvates
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Legal Events

Date	Code	Title	Description
1994-02-28	B1	Patent granted (law 1993)
1998-03-16	PUP	Patent expired