FI112657B - Uusi menetelmä 1R,cis-2,2-dimetyyli-3-formyylisyklopropaani-1-karboksyylihapon laktonin valmistamiseksi ja halogenoituja välituotteita - Google Patents
Uusi menetelmä 1R,cis-2,2-dimetyyli-3-formyylisyklopropaani-1-karboksyylihapon laktonin valmistamiseksi ja halogenoituja välituotteita Download PDFInfo
- Publication number
- FI112657B FI112657B FI925051A FI925051A FI112657B FI 112657 B FI112657 B FI 112657B FI 925051 A FI925051 A FI 925051A FI 925051 A FI925051 A FI 925051A FI 112657 B FI112657 B FI 112657B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- acid
- process according
- give
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract description 7
- 150000002596 lactones Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 239000007800 oxidant agent Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 235000011160 magnesium carbonates Nutrition 0.000 claims description 2
- 150000002895 organic esters Chemical class 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 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 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims 1
- 235000012254 magnesium hydroxide Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910001950 potassium oxide Inorganic materials 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000011261 inert gas Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 T acid lactone Chemical class 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WQYHFEJUFAFAAB-UHFFFAOYSA-N 1-(carboxymethyl)-3-hydroxy-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(O)C1(CC(O)=O)C(O)=O WQYHFEJUFAFAAB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical compound [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9113776 | 1991-11-08 | ||
| FR9113776A FR2683526B1 (fr) | 1991-11-08 | 1991-11-08 | Nouveau procede de preparation de la lactone de l'acide 1r, cis 2,2-dimethyl 3-formyl cyclopropane-1-carboxylique et intermediaires halogenes. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI925051A0 FI925051A0 (fi) | 1992-11-06 |
| FI925051L FI925051L (fi) | 1993-05-09 |
| FI112657B true FI112657B (fi) | 2003-12-31 |
Family
ID=9418741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI925051A FI112657B (fi) | 1991-11-08 | 1992-11-06 | Uusi menetelmä 1R,cis-2,2-dimetyyli-3-formyylisyklopropaani-1-karboksyylihapon laktonin valmistamiseksi ja halogenoituja välituotteita |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5276167A (de) |
| EP (1) | EP0541446B1 (de) |
| JP (1) | JP3151074B2 (de) |
| KR (1) | KR100227304B1 (de) |
| CN (1) | CN1050838C (de) |
| AT (1) | ATE134627T1 (de) |
| AU (1) | AU651301B2 (de) |
| BR (1) | BR9204331A (de) |
| CA (1) | CA2082285C (de) |
| DE (1) | DE69208591T2 (de) |
| DK (1) | DK0541446T3 (de) |
| ES (1) | ES2084309T3 (de) |
| FI (1) | FI112657B (de) |
| FR (1) | FR2683526B1 (de) |
| GR (1) | GR3019147T3 (de) |
| HU (1) | HU215577B (de) |
| MX (1) | MX9206358A (de) |
| RU (1) | RU2086546C1 (de) |
| UA (1) | UA44883C2 (de) |
| ZA (1) | ZA928570B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0735281B2 (ja) * | 1988-02-16 | 1995-04-19 | 学校法人松本歯科大学 | 硬化性組成物 |
| US6413773B1 (en) | 1998-06-01 | 2002-07-02 | The Regents Of The University Of California | Phosphatidylinositol 3-kinase inhibitors as stimulators of endocrine differentiation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE371821B (de) * | 1968-07-12 | 1974-12-02 | Roussel Uclaf | |
| FR1580474A (de) * | 1968-07-12 | 1969-09-05 | ||
| US4014918A (en) * | 1968-07-12 | 1977-03-29 | Roussel-Uclaf | Process for the preparation of cyclopropane derivatives and compounds produced therein |
| FR2396006A1 (fr) * | 1977-06-27 | 1979-01-26 | Roussel Uclaf | Nouveaux composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliques |
| US4132717A (en) * | 1977-08-09 | 1979-01-02 | Shell Oil Company | Enol lactone intermediate for the preparation of (1R,cis)-caronaldehydic acid |
-
1991
- 1991-11-08 FR FR9113776A patent/FR2683526B1/fr not_active Expired - Lifetime
-
1992
- 1992-10-08 RU SU925052809A patent/RU2086546C1/ru not_active IP Right Cessation
- 1992-10-21 US US07/964,500 patent/US5276167A/en not_active Expired - Lifetime
- 1992-11-05 AT AT92402995T patent/ATE134627T1/de not_active IP Right Cessation
- 1992-11-05 MX MX9206358A patent/MX9206358A/es unknown
- 1992-11-05 DK DK92402995.2T patent/DK0541446T3/da active
- 1992-11-05 DE DE69208591T patent/DE69208591T2/de not_active Expired - Lifetime
- 1992-11-05 ES ES92402995T patent/ES2084309T3/es not_active Expired - Lifetime
- 1992-11-05 EP EP92402995A patent/EP0541446B1/de not_active Expired - Lifetime
- 1992-11-06 AU AU28189/92A patent/AU651301B2/en not_active Ceased
- 1992-11-06 HU HU9203490A patent/HU215577B/hu unknown
- 1992-11-06 BR BR929204331A patent/BR9204331A/pt not_active IP Right Cessation
- 1992-11-06 FI FI925051A patent/FI112657B/fi not_active IP Right Cessation
- 1992-11-06 CA CA002082285A patent/CA2082285C/fr not_active Expired - Fee Related
- 1992-11-06 ZA ZA928570A patent/ZA928570B/xx unknown
- 1992-11-06 JP JP32137292A patent/JP3151074B2/ja not_active Expired - Lifetime
- 1992-11-07 CN CN92112855A patent/CN1050838C/zh not_active Expired - Lifetime
- 1992-11-07 KR KR1019920020870A patent/KR100227304B1/ko not_active Expired - Lifetime
-
1993
- 1993-06-18 UA UA93002998A patent/UA44883C2/uk unknown
-
1996
- 1996-02-29 GR GR950403176T patent/GR3019147T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2086546C1 (ru) | 1997-08-10 |
| ES2084309T3 (es) | 1996-05-01 |
| CN1072178A (zh) | 1993-05-19 |
| GR3019147T3 (en) | 1996-05-31 |
| UA44883C2 (uk) | 2002-03-15 |
| HUT63157A (en) | 1993-07-28 |
| FI925051L (fi) | 1993-05-09 |
| HU215577B (hu) | 1999-01-28 |
| CN1050838C (zh) | 2000-03-29 |
| HU9203490D0 (en) | 1993-03-01 |
| FI925051A0 (fi) | 1992-11-06 |
| EP0541446B1 (de) | 1996-02-28 |
| KR930010019A (ko) | 1993-06-21 |
| AU2818992A (en) | 1993-05-13 |
| ZA928570B (en) | 1993-11-08 |
| FR2683526B1 (fr) | 1994-01-21 |
| DE69208591T2 (de) | 1996-09-19 |
| JP3151074B2 (ja) | 2001-04-03 |
| DK0541446T3 (da) | 1996-04-29 |
| DE69208591D1 (de) | 1996-04-04 |
| JPH05222026A (ja) | 1993-08-31 |
| AU651301B2 (en) | 1994-07-14 |
| EP0541446A1 (de) | 1993-05-12 |
| BR9204331A (pt) | 1993-05-18 |
| FR2683526A1 (fr) | 1993-05-14 |
| MX9206358A (es) | 1994-02-28 |
| KR100227304B1 (ko) | 1999-11-01 |
| CA2082285A1 (fr) | 1993-05-09 |
| CA2082285C (fr) | 2001-02-27 |
| US5276167A (en) | 1994-01-04 |
| ATE134627T1 (de) | 1996-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: AVENTIS PHARMA S.A. Free format text: AVENTIS PHARMA S.A. |
|
| MA | Patent expired |