NO310862B1 - Fremgangsmåte for fremstilling av butantrioler - Google Patents

Fremgangsmåte for fremstilling av butantrioler Download PDF

Info

Publication number: NO310862B1
Authority: NO; Norway
Prior art keywords: ether; alcohol; malic acid; sodium borohydride; mixture
Prior art date: 1996-08-30

Application number

NO19990931A

Other languages

English (en)

Norwegian (no)

Other versions

NO990931D0 (no

NO990931L (no

Inventor

Michael John Monteith

David Schofield

Mark Bailey

Original Assignee

Avecia Ltd

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.)

1996-08-30

Filing date

1999-02-26

Publication date

2001-09-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10799151&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO310862(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1999-02-26 Application filed by Avecia Ltd filed Critical Avecia Ltd

1999-02-26 Publication of NO990931D0 publication Critical patent/NO990931D0/no

1999-02-26 Publication of NO990931L publication Critical patent/NO990931L/no

2001-09-10 Publication of NO310862B1 publication Critical patent/NO310862B1/no

Links

238000000034 method Methods 0.000 title claims abstract description 45
GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical class CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 title claims abstract description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 55
229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 32
239000012279 sodium borohydride Substances 0.000 claims abstract description 32
-1 malic acid diester Chemical class 0.000 claims abstract description 27
239000001630 malic acid Substances 0.000 claims abstract description 24
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 23
235000011090 malic acid Nutrition 0.000 claims abstract description 21
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims abstract description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 49
239000000203 mixture Substances 0.000 claims description 32
ARXKVVRQIIOZGF-UHFFFAOYSA-N (2R)-1,2,4-butanetriol Natural products OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 15
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 10
ARXKVVRQIIOZGF-BYPYZUCNSA-N 2-deoxyerythritol Chemical compound OCC[C@H](O)CO ARXKVVRQIIOZGF-BYPYZUCNSA-N 0.000 claims description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
ARXKVVRQIIOZGF-SCSAIBSYSA-N (2r)-butane-1,2,4-triol Chemical compound OCC[C@@H](O)CO ARXKVVRQIIOZGF-SCSAIBSYSA-N 0.000 claims description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
VKNUORWMCINMRB-UHFFFAOYSA-N diethyl malate Chemical group CCOC(=O)CC(O)C(=O)OCC VKNUORWMCINMRB-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
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 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
150000005690 diesters Chemical class 0.000 claims description 2
238000000926 separation method Methods 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 7
150000004702 methyl esters Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 68
YSEKNCXYRGKTBJ-UHFFFAOYSA-N dimethyl 2-hydroxybutanedioate Chemical compound COC(=O)CC(O)C(=O)OC YSEKNCXYRGKTBJ-UHFFFAOYSA-N 0.000 description 18
229940099690 malic acid Drugs 0.000 description 15
239000000706 filtrate Substances 0.000 description 8
239000011928 denatured alcohol Substances 0.000 description 7
239000002002 slurry Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
125000004185 ester group Chemical group 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
DZAIOXUZHHTJKN-UHFFFAOYSA-N 2-Desoxy-D-glycero-tetronsaeure Natural products OCC(O)CC(O)=O DZAIOXUZHHTJKN-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000000470 constituent Substances 0.000 description 1
235000021438 curry Nutrition 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
YSEKNCXYRGKTBJ-BYPYZUCNSA-N dimethyl (2s)-2-hydroxybutanedioate Chemical compound COC(=O)C[C@H](O)C(=O)OC YSEKNCXYRGKTBJ-BYPYZUCNSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
229940116298 l- malic acid Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
CAYPTNNZMBWAKE-UHFFFAOYSA-N propan-1-ol propan-2-ol Chemical compound CCCO.CC(C)O.CC(C)O.CC(C)O CAYPTNNZMBWAKE-UHFFFAOYSA-N 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003491 tear gas Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/22—Trihydroxylic alcohols, e.g. glycerol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)

NO19990931A 1996-08-30 1999-02-26 Fremgangsmåte for fremstilling av butantrioler NO310862B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9618099.7A GB9618099D0 (en)	1996-08-30	1996-08-30	Process
PCT/GB1997/002183 WO1998008793A1 (en)	1996-08-30	1997-08-14	Process for the preparation of butane triols

Publications (3)

Publication Number	Publication Date
NO990931D0 NO990931D0 (no)	1999-02-26
NO990931L NO990931L (no)	1999-02-26
NO310862B1 true NO310862B1 (no)	2001-09-10

Family

ID=10799151

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19990931A NO310862B1 (no)	1996-08-30	1999-02-26	Fremgangsmåte for fremstilling av butantrioler

Country Status (16)

Country	Link
US (1)	US6479714B1 (de)
EP (1)	EP0923516B1 (de)
JP (1)	JP3919128B2 (de)
KR (1)	KR100573952B1 (de)
CN (1)	CN1101368C (de)
AT (1)	ATE208360T1 (de)
AU (1)	AU723940B2 (de)
CA (1)	CA2263147C (de)
CZ (1)	CZ293042B6 (de)
DE (1)	DE69708125T2 (de)
ES (1)	ES2163190T3 (de)
GB (1)	GB9618099D0 (de)
HU (1)	HU223087B1 (de)
IL (1)	IL128682A0 (de)
NO (1)	NO310862B1 (de)
WO (1)	WO1998008793A1 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5808107A (en) †	1997-10-31	1998-09-15	Board Of Trustees Operating Michigan State University	Process for the preparation of hydroxy substituted gamma butyrolactones
US6949684B2 (en)	1998-03-03	2005-09-27	Daiso Co., Ltd.	Process for preparing 1,2,4-butanetriol
CA2322480A1 (en) *	1998-03-03	1999-09-10	Daiso Co., Ltd.	Process for producing 1,2,4-butanetriol
KR100461571B1 (ko) *	2000-05-23	2004-12-14	삼성정밀화학 주식회사	고순도 (ｓ)-1,2,4-부탄트리올의 제조방법
JP4305388B2 (ja) *	2002-06-14	2009-07-29	ダイソー株式会社	１，２，４−ブタントリオールの製造方法
WO2005068642A2 (en)	2003-10-01	2005-07-28	Board Of Trustees Operating Michigan State University	Bacterial synthesis of 1,2,4-butanetriol enantiomers
CN100420664C (zh) *	2005-01-11	2008-09-24	中国科学院大连化学物理研究所	一种1,2,4-丁三醇的合成方法
JP2006257027A (ja) *	2005-03-17	2006-09-28	Tosoh F-Tech Inc	トリフルオロアセトアルデヒドの水和物および／又はヘミアセタールの製造方法
US20110165641A1 (en) *	2006-03-31	2011-07-07	The Board Of Trustees Of Michigan State University	Synthesis of 1,2,4-Butanetriol Enantiomers from Carbohydrates
KR20090039738A (ko) *	2006-07-19	2009-04-22	보드 오브 트러스티즈 오브 미시건 스테이트 유니버시티	Ｄ－１，２，４－부탄트리올의 미생물 합성
US8367877B2 (en) *	2009-11-17	2013-02-05	Alliant Techsystems Inc.	Methods of purifying 1,2,4-butanetriol
CN109999843A (zh) *	2019-04-29	2019-07-12	中国科学院青岛生物能源与过程研究所	一种用于苹果酸酯化的固体超强酸催化剂
CN111116312B (zh) *	2019-12-19	2022-10-28	中国科学院青岛生物能源与过程研究所	一种催化加氢制备1,2,4-丁三醇的方法
CN117295705A (zh)	2021-05-10	2023-12-26	大金工业株式会社	醇类的制造方法和组合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2683721A (en) *	1952-01-17	1954-07-13	Hermann I Schlesinger	Method of reducing and hydrogenating chemical compounds by reacting with alkali metal borohydrides
US4410744A (en) *	1982-08-02	1983-10-18	Thiokol Corporation	Making 1,2,4-butanetriol by hydroformylation of glycidol
DE3803581A1 (de) *	1988-02-06	1989-08-17	Basf Ag	Verfahren zur herstellung von 1,2,4-butantriol
JPH03197434A (ja) *	1989-12-26	1991-08-28	Kao Corp	還元方法
JP3351563B2 (ja) *	1992-12-03	2002-11-25	鐘淵化学工業株式会社	３−ヒドロキシ酪酸誘導体の製造法
US5808107A (en)	1997-10-31	1998-09-15	Board Of Trustees Operating Michigan State University	Process for the preparation of hydroxy substituted gamma butyrolactones

1996
- 1996-08-30 GB GBGB9618099.7A patent/GB9618099D0/en active Pending
1997
- 1997-08-14 AT AT97936784T patent/ATE208360T1/de not_active IP Right Cessation
- 1997-08-14 JP JP51135598A patent/JP3919128B2/ja not_active Expired - Fee Related
- 1997-08-14 US US09/242,899 patent/US6479714B1/en not_active Expired - Fee Related
- 1997-08-14 AU AU39486/97A patent/AU723940B2/en not_active Ceased
- 1997-08-14 EP EP97936784A patent/EP0923516B1/de not_active Expired - Lifetime
- 1997-08-14 ES ES97936784T patent/ES2163190T3/es not_active Expired - Lifetime
- 1997-08-14 HU HU9904643A patent/HU223087B1/hu not_active IP Right Cessation
- 1997-08-14 CZ CZ1999657A patent/CZ293042B6/cs not_active IP Right Cessation
- 1997-08-14 KR KR1019997001633A patent/KR100573952B1/ko not_active Expired - Fee Related
- 1997-08-14 WO PCT/GB1997/002183 patent/WO1998008793A1/en not_active Ceased
- 1997-08-14 DE DE69708125T patent/DE69708125T2/de not_active Expired - Lifetime
- 1997-08-14 CN CN97198976A patent/CN1101368C/zh not_active Expired - Fee Related
- 1997-08-14 CA CA002263147A patent/CA2263147C/en not_active Expired - Fee Related
- 1997-08-14 IL IL12868297A patent/IL128682A0/xx unknown
1999
- 1999-02-26 NO NO19990931A patent/NO310862B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU723940B2 (en)	2000-09-07
EP0923516A1 (de)	1999-06-23
GB9618099D0 (en)	1996-10-09
ATE208360T1 (de)	2001-11-15
CZ293042B6 (cs)	2004-01-14
WO1998008793A1 (en)	1998-03-05
KR100573952B1 (ko)	2006-04-26
KR20000035907A (ko)	2000-06-26
CA2263147A1 (en)	1998-03-05
CZ65799A3 (cs)	1999-06-16
NO990931D0 (no)	1999-02-26
US6479714B1 (en)	2002-11-12
JP3919128B2 (ja)	2007-05-23
HUP9904643A2 (hu)	2000-05-28
IL128682A0 (en)	2000-01-31
HU223087B1 (hu)	2004-03-29
CA2263147C (en)	2006-12-19
CN1234016A (zh)	1999-11-03
NO990931L (no)	1999-02-26
HUP9904643A3 (en)	2001-02-28
ES2163190T3 (es)	2002-01-16
DE69708125D1 (de)	2001-12-13
JP2000516947A (ja)	2000-12-19
CN1101368C (zh)	2003-02-12
DE69708125T2 (de)	2002-06-06
EP0923516B1 (de)	2001-11-07
AU3948697A (en)	1998-03-19

Legal Events

Date	Code	Title	Description
2011-04-04	MM1K	Lapsed by not paying the annual fees

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