FI89170B - Foerfarande foer framstaellning av alifatylfosfinsyraderivat - Google Patents
Foerfarande foer framstaellning av alifatylfosfinsyraderivat Download PDFInfo
- Publication number
- FI89170B FI89170B FI884166A FI884166A FI89170B FI 89170 B FI89170 B FI 89170B FI 884166 A FI884166 A FI 884166A FI 884166 A FI884166 A FI 884166A FI 89170 B FI89170 B FI 89170B
- Authority
- FI
- Finland
- Prior art keywords
- phosphinic acid
- acid
- formula
- starting material
- parts
- Prior art date
Links
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000002905 orthoesters Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 230000002378 acidificating effect Effects 0.000 claims abstract 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 14
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 5
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 4
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 claims description 3
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims description 2
- JDQNNHFSSCEQPM-UHFFFAOYSA-N 1-(1,1-dipropoxyethoxy)propane Chemical compound CCCOC(C)(OCCC)OCCC JDQNNHFSSCEQPM-UHFFFAOYSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- UEVZIKFSVBYKAC-UHFFFAOYSA-N 1-(1,1-dibutoxyethoxy)butane Chemical compound CCCCOC(C)(OCCCC)OCCCC UEVZIKFSVBYKAC-UHFFFAOYSA-N 0.000 claims 1
- RWNXXQFJBALKAX-UHFFFAOYSA-N 1-(dipropoxymethoxy)propane Chemical compound CCCOC(OCCC)OCCC RWNXXQFJBALKAX-UHFFFAOYSA-N 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- ZKNJRUPWSFSOFM-UHFFFAOYSA-N diethoxymethyl-ethoxy-oxophosphanium Chemical compound CCOC(OCC)[P+](=O)OCC ZKNJRUPWSFSOFM-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000003377 acid catalyst Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OGEBQHPVXHLCGQ-UHFFFAOYSA-N 1,1-diethoxyethyl-ethoxy-oxophosphanium Chemical compound CCO[P+](=O)C(C)(OCC)OCC OGEBQHPVXHLCGQ-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- WFSQCDSLKHKXTP-UHFFFAOYSA-N 1-butoxyethane-1,1-diol Chemical compound CCCCOC(C)(O)O WFSQCDSLKHKXTP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OQHXQHWAKWSBKE-UHFFFAOYSA-N CCCCOC(OCCCC)P(=O)OCCCC Chemical compound CCCCOC(OCCCC)P(=O)OCCCC OQHXQHWAKWSBKE-UHFFFAOYSA-N 0.000 description 1
- WWLJAPIXMAPFDO-UHFFFAOYSA-N COC(OC)P(=O)OC Chemical compound COC(OC)P(=O)OC WWLJAPIXMAPFDO-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- -1 aliphatic phosphinic acid derivatives Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- DGLRDKLJZLEJCY-UHFFFAOYSA-L disodium hydrogenphosphate dodecahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].OP([O-])([O-])=O DGLRDKLJZLEJCY-UHFFFAOYSA-L 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QCLYNERZQRZCKC-UHFFFAOYSA-N propoxymethanediol Chemical compound CCCOC(O)O QCLYNERZQRZCKC-UHFFFAOYSA-N 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical class CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
Claims (9)
1. Nytt förfarande för framställning av alkyl-dialkoxial-kylfosfinater med formeln I (RO) 2^- jj-OR I i vilken R betecknar C,-C4-alkyl och R' betecknar väte eller C,-C4-alkyl, kännetecknat därav att vattenhaltig fosfinsyra omsättes i närvaro av en sur katalysator med en motsvarande trialkylortoester med formeln II (RO)3CR' II i vilken resterna R och R' har ovan anförda betydelser, varvid den använda mängden ortoestern med formeln II är lika stor eller större än den stökiömetriska mängden av vatten och fosfinsyra närvarande i det vattenhaltiga fosfinsyrautgängsmaterialet.
2. Förfarande enligt patentkravet 1, känneteck- : n a t därav, att den använda vattenhaltiga fosfinsyran innehäller 50 - 95 vikt-% fosfinsyra.
3. Förfarande enligt patentkravet 1 eller 2, k ä n n e-tecknat därav, att den använda mängden ortoester-utgängsmaterial med formeln II är 1 - 10 gänger den stökiömetriska mängden av vatten och fosfinsyra närvarande i det vattenhaltiga fosfinsyrautgängsmaterialet.
4. Förfarande enligt patentkravet 1 eller 2, kännetecknat därav, att den använda mängden ortoester-utgängsmaterial med formeln II är 1,0 - 5 gänger den stökiömetriska mängden av vatten och fosfinsyra närvarande i det vattenhaltiga fosfinsyrautgängsmaterialet. 12 891 70
5. Förfarande enligt patentkravet 1 eller 2, kanne-t e c k n a t därav, att den använda mängden ortoester-utgängsmaterial med formeln II är 2,2 - 4,4 gänger den stökiömetriska mängden av vatten och fosfinsyra närvaran-de i det vattenhaltiga fosfinsyrautgängsmaterialet.
6. Förfarande enligt nägot av patentkraven 1-5, k ä n-netecknat därav, att den sura katalysatorn är en mineralsyra, alkan- eller bensensulfonsyra eller en a-halogenerad alkansyra eller bortrifluordieterat.
7. Förfarande enligt nägot av patentkraven 1-5, k ä n-netecknat därav, att den sura katalysatorn är trifluorättiksyra.
8. Förfarande enligt nägot av patentkraven 1-7, k ä n-netecknat därav, att den sura katalysatorn an-vänds i en mängd av 0,01 - 0,4, t.ex. 0,05 - 0,3 syra-ekvivalenter.
9. Förfarande enligt nägot av patentkraven 1 - 8, k ä n-netecknat därav att utgängsmaterialet med formeln II är trimetyl-ortoacetat, trimetyl-ortoformiat, trietyl-ortoacetat, trietyl-ortoformiat, tri-n-propyl-ortoacetat, tri-n-propyl-ortoformiat, tri-n-butyl-orto-acetat och tri-n-butyl-ortoformiat.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878721442A GB8721442D0 (en) | 1987-09-11 | 1987-09-11 | Process |
| GB8721442 | 1987-09-11 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI884166A0 FI884166A0 (fi) | 1988-09-09 |
| FI884166A FI884166A (fi) | 1989-03-12 |
| FI89170B true FI89170B (fi) | 1993-05-14 |
| FI89170C FI89170C (sv) | 1993-08-25 |
Family
ID=10623659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI884166A FI89170C (sv) | 1987-09-11 | 1988-09-09 | Förfarande för framställning av alifatylfosfinsyraderivat |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4933478A (sv) |
| EP (1) | EP0307362B1 (sv) |
| JP (1) | JP2645101B2 (sv) |
| AT (1) | ATE118499T1 (sv) |
| CA (1) | CA1310976C (sv) |
| DE (1) | DE3853030T2 (sv) |
| DK (1) | DK169436B1 (sv) |
| ES (1) | ES2068209T3 (sv) |
| FI (1) | FI89170C (sv) |
| GB (1) | GB8721442D0 (sv) |
| GR (1) | GR3015075T3 (sv) |
| IE (1) | IE64978B1 (sv) |
| PT (1) | PT88445B (sv) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9104050D0 (en) * | 1991-02-27 | 1991-04-17 | Ciba Geigy Ag | Compounds |
| GB9604669D0 (en) | 1996-03-05 | 1996-05-01 | Ciba Geigy Ag | Chemical compounds |
| SE0402199D0 (sv) * | 2004-09-13 | 2004-09-13 | Astrazeneca Ab | New process I |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1174439A1 (ru) * | 1984-06-28 | 1985-08-23 | МГУ им.М.В.Ломоносова | Способ получени @ -алкил- @ -триметилсилил(диалкоксиметил)фосфонитов |
| GB8425872D0 (en) * | 1984-10-12 | 1984-11-21 | Ciba Geigy Ag | Chemical compounds |
-
1987
- 1987-09-11 GB GB878721442A patent/GB8721442D0/en active Pending
-
1988
- 1988-09-01 US US07/239,233 patent/US4933478A/en not_active Expired - Fee Related
- 1988-09-05 ES ES88810606T patent/ES2068209T3/es not_active Expired - Lifetime
- 1988-09-05 DE DE3853030T patent/DE3853030T2/de not_active Expired - Fee Related
- 1988-09-05 AT AT88810606T patent/ATE118499T1/de not_active IP Right Cessation
- 1988-09-05 EP EP88810606A patent/EP0307362B1/en not_active Expired - Lifetime
- 1988-09-07 PT PT88445A patent/PT88445B/pt not_active IP Right Cessation
- 1988-09-09 IE IE274988A patent/IE64978B1/en not_active IP Right Cessation
- 1988-09-09 FI FI884166A patent/FI89170C/sv not_active IP Right Cessation
- 1988-09-09 JP JP63224834A patent/JP2645101B2/ja not_active Expired - Lifetime
- 1988-09-09 CA CA000576887A patent/CA1310976C/en not_active Expired - Lifetime
- 1988-09-09 DK DK501188A patent/DK169436B1/da not_active IP Right Cessation
-
1995
- 1995-02-16 GR GR950400121T patent/GR3015075T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0307362B1 (en) | 1995-02-15 |
| IE882749L (en) | 1989-03-11 |
| GB8721442D0 (en) | 1987-10-21 |
| PT88445B (pt) | 1992-10-30 |
| JP2645101B2 (ja) | 1997-08-25 |
| FI884166A (fi) | 1989-03-12 |
| GR3015075T3 (en) | 1995-05-31 |
| DK501188D0 (da) | 1988-09-09 |
| FI89170C (sv) | 1993-08-25 |
| DE3853030T2 (de) | 1995-06-22 |
| FI884166A0 (fi) | 1988-09-09 |
| DE3853030D1 (de) | 1995-03-23 |
| DK501188A (da) | 1989-03-12 |
| ES2068209T3 (es) | 1995-04-16 |
| JPH01110693A (ja) | 1989-04-27 |
| PT88445A (pt) | 1989-07-31 |
| IE64978B1 (en) | 1995-09-20 |
| DK169436B1 (da) | 1994-10-31 |
| EP0307362A3 (en) | 1990-05-30 |
| ATE118499T1 (de) | 1995-03-15 |
| EP0307362A2 (en) | 1989-03-15 |
| US4933478A (en) | 1990-06-12 |
| CA1310976C (en) | 1992-12-01 |
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