DK169505B1 - Fremgangsmåde til fremstilling af imidazopyridiner og mellemprodukter til brug ved fremgangsmåden - Google Patents

Fremgangsmåde til fremstilling af imidazopyridiner og mellemprodukter til brug ved fremgangsmåden Download PDF

Info

Publication number: DK169505B1
Authority: DK; Denmark
Prior art keywords: hydrogen; alkyl; compound; formula; halogen
Prior art date: 1986-06-27

Application number

DK328187A

Other languages

Danish (da)

English (en)

Other versions

DK328187A (da

DK328187D0 (da

Inventor

Guy Rossey

David Long

Original Assignee

Synthelabo

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.)

1986-06-27

Filing date

1987-06-26

Publication date

1994-11-14

1987-06-26 Application filed by Synthelabo filed Critical Synthelabo

1987-06-26 Publication of DK328187D0 publication Critical patent/DK328187D0/da

1987-12-28 Publication of DK328187A publication Critical patent/DK328187A/da

1994-11-14 Application granted granted Critical

1994-11-14 Publication of DK169505B1 publication Critical patent/DK169505B1/da

Links

238000000034 method Methods 0.000 title claims description 11
239000000543 intermediate Substances 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 5
150000005232 imidazopyridines Chemical class 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 2
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 6
108090000623 proteins and genes Proteins 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
238000003756 stirring Methods 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
XQRILQRMHDAYOF-UHFFFAOYSA-N 2,2-dimethoxy-n,n-dimethylacetamide Chemical compound COC(OC)C(=O)N(C)C XQRILQRMHDAYOF-UHFFFAOYSA-N 0.000 description 2
YASDVDCTWHEHIL-UHFFFAOYSA-N 2,2-dimethoxy-n,n-dipropylacetamide Chemical compound CCCN(CCC)C(=O)C(OC)OC YASDVDCTWHEHIL-UHFFFAOYSA-N 0.000 description 2
UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
-1 NaBH 2 Substances 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
UOMXIKXHYRRODT-UHFFFAOYSA-N 2,2-dichloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)C(Cl)Cl UOMXIKXHYRRODT-UHFFFAOYSA-N 0.000 description 1
FNVDWIPIYNKYDK-UHFFFAOYSA-N 2,2-dichloro-n,n-dipropylacetamide Chemical compound CCCN(CCC)C(=O)C(Cl)Cl FNVDWIPIYNKYDK-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
CFINUJBABHRHDT-UHFFFAOYSA-N 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(Cl)=CC=C1C1=CN(C=C(Cl)C=C2)C2=N1 CFINUJBABHRHDT-UHFFFAOYSA-N 0.000 description 1
AWEWSJJCANQFRB-UHFFFAOYSA-N 6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridine Chemical compound C1=CC(C)=CC=C1C1=CN(C=C(C)C=C2)C2=N1 AWEWSJJCANQFRB-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
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 1
235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000001582 butter acid Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

DK328187A 1986-06-27 1987-06-26 Fremgangsmåde til fremstilling af imidazopyridiner og mellemprodukter til brug ved fremgangsmåden DK169505B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8609330A FR2600650B1 (fr)	1986-06-27	1986-06-27	Procede de preparation d'imidazopyridines et composes intermediaires
FR8609330		1986-06-27

Publications (3)

Publication Number	Publication Date
DK328187D0 DK328187D0 (da)	1987-06-26
DK328187A DK328187A (da)	1987-12-28
DK169505B1 true DK169505B1 (da)	1994-11-14

Family

ID=9336785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK328187A DK169505B1 (da)	1986-06-27	1987-06-26	Fremgangsmåde til fremstilling af imidazopyridiner og mellemprodukter til brug ved fremgangsmåden

Country Status (21)

Country	Link
US (1)	US4794185A (de)
EP (1)	EP0251859B1 (de)
JP (1)	JPH0653740B2 (de)
KR (1)	KR940006594B1 (de)
AR (1)	AR243188A1 (de)
AT (1)	ATE58537T1 (de)
AU (1)	AU7477287A (de)
CA (1)	CA1324138C (de)
DE (1)	DE3766300D1 (de)
DK (1)	DK169505B1 (de)
ES (1)	ES2019646B3 (de)
FI (1)	FI872850A7 (de)
FR (1)	FR2600650B1 (de)
GR (1)	GR3001118T3 (de)
HU (1)	HU204826B (de)
IE (1)	IE60467B1 (de)
IL (1)	IL82982A (de)
NO (1)	NO167392C (de)
NZ (1)	NZ220853A (de)
PT (1)	PT85188B (de)
ZA (1)	ZA874643B (de)

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ES2320758T3 (es)	2002-12-18	2009-05-28	Mallinckrodt Inc.	Sintesis de heteroaril acetamidas.
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GB0311457D0 (en) *	2003-05-19	2003-06-25	Sciencom Ltd	New therapeutic use
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WO2006008636A2 (en) *	2004-07-16	2006-01-26	Ranbaxy Laboratories Limited	Processes for the preparation of zolpidem and its hemitartrate
EP2258359A3 (de)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenese durch Modulation des Muscarinrezeptors mit Sabcomelin
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
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CN103360387B (zh) *	2012-03-28	2016-12-14	江苏豪森药业集团有限公司	一种制备化合物唑吡坦的方法
KR101704589B1 (ko) *	2016-07-12	2017-02-08	주식회사 뉴트라팜텍	후박 추출물 및 신이 추출물의 혼합물을 유효성분으로 함유하는 치주조직 성장 촉진용 및 치주염 예방 또는 치료용 약학적 조성물
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GR68765B (de) *	1979-06-20	1982-02-17	Rohm & Haas
FR2492382A1 (fr) *	1980-10-22	1982-04-23	Synthelabo	Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique

1986
- 1986-06-27 FR FR8609330A patent/FR2600650B1/fr not_active Expired
1987
- 1987-06-17 EP EP87401353A patent/EP0251859B1/de not_active Expired - Lifetime
- 1987-06-17 ES ES87401353T patent/ES2019646B3/es not_active Expired - Lifetime
- 1987-06-17 DE DE8787401353T patent/DE3766300D1/de not_active Expired - Lifetime
- 1987-06-17 AT AT87401353T patent/ATE58537T1/de active
- 1987-06-24 IL IL82982A patent/IL82982A/xx not_active IP Right Cessation
- 1987-06-26 HU HU872909A patent/HU204826B/hu unknown
- 1987-06-26 US US07/066,530 patent/US4794185A/en not_active Expired - Lifetime
- 1987-06-26 ZA ZA874643A patent/ZA874643B/xx unknown
- 1987-06-26 IE IE172387A patent/IE60467B1/en not_active IP Right Cessation
- 1987-06-26 CA CA000540712A patent/CA1324138C/en not_active Expired - Fee Related
- 1987-06-26 NO NO872682A patent/NO167392C/no not_active IP Right Cessation
- 1987-06-26 KR KR1019870006538A patent/KR940006594B1/ko not_active Expired - Lifetime
- 1987-06-26 JP JP62160827A patent/JPH0653740B2/ja not_active Expired - Lifetime
- 1987-06-26 FI FI872850A patent/FI872850A7/fi not_active Application Discontinuation
- 1987-06-26 PT PT85188A patent/PT85188B/pt unknown
- 1987-06-26 DK DK328187A patent/DK169505B1/da not_active IP Right Cessation
- 1987-06-26 NZ NZ220853A patent/NZ220853A/xx unknown
- 1987-06-26 AU AU74772/87A patent/AU7477287A/en not_active Abandoned
- 1987-06-26 AR AR87307995A patent/AR243188A1/es active
1990
- 1990-11-28 GR GR90400982T patent/GR3001118T3/el unknown

Also Published As

Publication number	Publication date
NZ220853A (en)	1989-09-27
GR3001118T3 (en)	1992-05-12
IL82982A0 (en)	1987-12-20
FI872850A7 (fi)	1987-12-28
IL82982A (en)	1992-03-29
IE871723L (en)	1987-12-27
ATE58537T1 (de)	1990-12-15
EP0251859A2 (de)	1988-01-07
HUT44547A (en)	1988-03-28
CA1324138C (en)	1993-11-09
NO167392B (no)	1991-07-22
EP0251859A3 (en)	1989-07-19
DK328187A (da)	1987-12-28
PT85188B (pt)	1990-03-30
KR880000433A (ko)	1988-03-25
US4794185A (en)	1988-12-27
AR243188A1 (es)	1993-07-30
NO872682L (no)	1987-12-28
NO167392C (no)	1991-10-30
ZA874643B (en)	1988-02-24
HU204826B (en)	1992-02-28
DK328187D0 (da)	1987-06-26
FR2600650B1 (fr)	1988-09-09
PT85188A (fr)	1987-07-01
FR2600650A1 (fr)	1987-12-31
DE3766300D1 (de)	1991-01-03
EP0251859B1 (de)	1990-11-22
AU7477287A (en)	1988-01-07
IE60467B1 (en)	1994-07-13
ES2019646B3 (es)	1991-07-01
JPH0653740B2 (ja)	1994-07-20
FI872850A0 (fi)	1987-06-26
JPS638384A (ja)	1988-01-14
KR940006594B1 (ko)	1994-07-23
NO872682D0 (no)	1987-06-26

Legal Events

Date	Code	Title	Description
1994-11-14	B1	Patent granted (law 1993)
2007-07-16	PUP	Patent expired

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