CA1297126C - Method for the preparation of anilinofumarate - Google Patents
Method for the preparation of anilinofumarateInfo
- Publication number
- CA1297126C CA1297126C CA000578776A CA578776A CA1297126C CA 1297126 C CA1297126 C CA 1297126C CA 000578776 A CA000578776 A CA 000578776A CA 578776 A CA578776 A CA 578776A CA 1297126 C CA1297126 C CA 1297126C
- Authority
- CA
- Canada
- Prior art keywords
- quinoline
- preparation
- anilinofumarate
- aniline
- tri
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- XQRVITDMGTWTIC-VURMDHGXSA-N (Z)-2-anilinobut-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)/NC1=CC=CC=C1 XQRVITDMGTWTIC-VURMDHGXSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- XSCRWBSKSVOZOK-UHFFFAOYSA-N 2,3-dichlorobutanedioic acid Chemical compound OC(=O)C(Cl)C(Cl)C(O)=O XSCRWBSKSVOZOK-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims 1
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 abstract 1
- YHUVMHKAHWKQBI-UHFFFAOYSA-N quinoline-2,3-dicarboxylic acid Chemical class C1=CC=C2N=C(C(O)=O)C(C(=O)O)=CC2=C1 YHUVMHKAHWKQBI-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- PBGMSGHICSEALQ-UHFFFAOYSA-N diethyl 2,3-dichlorobutanedioate Chemical compound CCOC(=O)C(Cl)C(Cl)C(=O)OCC PBGMSGHICSEALQ-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical class OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 3
- QQVDYSUDFZZPSU-UHFFFAOYSA-M chloromethylidene(dimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)=CCl QQVDYSUDFZZPSU-UHFFFAOYSA-M 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical class [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical class C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- -1 quinoline imida-zolinone compounds Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- QDXJFRHCHWDQSP-UHFFFAOYSA-N 1,4-dihydroimidazol-5-one;quinoline Chemical compound O=C1CNC=N1.N1=CC=CC2=CC=CC=C21 QDXJFRHCHWDQSP-UHFFFAOYSA-N 0.000 description 1
- PBHUSRBVKLAGGU-UHFFFAOYSA-N 2-carbamoylquinoline-3-carboxylic acid Chemical class C1=CC=C2C=C(C(O)=O)C(C(=O)N)=NC2=C1 PBHUSRBVKLAGGU-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- ROMURMXNNUEGCC-BENRWUELSA-N diethyl (z)-2-anilinobut-2-enedioate Chemical compound CCOC(=O)\C=C(C(=O)OCC)/NC1=CC=CC=C1 ROMURMXNNUEGCC-BENRWUELSA-N 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- 229940071094 diethyl oxalacetate Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Control Of Transmission Device (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/101,453 | 1987-10-01 | ||
| US07/101,453 US4814486A (en) | 1987-10-01 | 1987-10-01 | Method for the preparation of anilinofumarate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1297126C true CA1297126C (en) | 1992-03-10 |
Family
ID=22284722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000578776A Expired - Lifetime CA1297126C (en) | 1987-10-01 | 1988-09-29 | Method for the preparation of anilinofumarate |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4814486A (en, 2012) |
| EP (1) | EP0309711B1 (en, 2012) |
| JP (1) | JP2703573B2 (en, 2012) |
| KR (1) | KR970006470B1 (en, 2012) |
| AR (1) | AR244658A1 (en, 2012) |
| AT (1) | ATE85321T1 (en, 2012) |
| AU (1) | AU611952B2 (en, 2012) |
| BG (1) | BG47347A3 (en, 2012) |
| BR (1) | BR8805058A (en, 2012) |
| CA (1) | CA1297126C (en, 2012) |
| CS (1) | CS275946B6 (en, 2012) |
| DD (1) | DD275453A5 (en, 2012) |
| DE (1) | DE3878122T2 (en, 2012) |
| ES (1) | ES2039525T3 (en, 2012) |
| GR (1) | GR3006960T3 (en, 2012) |
| HU (1) | HU200592B (en, 2012) |
| IE (1) | IE63235B1 (en, 2012) |
| IL (1) | IL87546A0 (en, 2012) |
| RO (1) | RO101205B1 (en, 2012) |
| RU (1) | RU1773259C (en, 2012) |
| YU (1) | YU45062B (en, 2012) |
| ZA (1) | ZA887372B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910327A (en) * | 1982-05-25 | 1990-03-20 | American Cyanamid Company | Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid: dialkyl 3-(substituted)phenylaminobut-2-ene-dioates and methods for the preparation thereof |
| US5001254A (en) * | 1986-08-29 | 1991-03-19 | American Cyanamid Co | Novel method for the preparation of quinoline-2,3-dicarboxylic |
| US4904816A (en) * | 1989-06-15 | 1990-02-27 | American Cyanamid Company | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof |
| EP1479667A4 (en) | 2002-02-28 | 2006-05-03 | Sumitomo Chemical Co | PROCESS FOR PRODUCING CHROMIUM COMPOUND |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4638068A (en) * | 1981-04-09 | 1987-01-20 | American Cyanamid Company | 2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| US4459409A (en) * | 1982-05-25 | 1984-07-10 | American Cyanamid Company | Process for the preparation of 2,3-quinolinedicarboxylic acids |
| US4518780A (en) * | 1982-05-25 | 1985-05-21 | American Cyanamid Company | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)nicotinic acids and quinoline-3-carboxylic acids |
| US4656283A (en) * | 1982-05-25 | 1987-04-07 | American Cyanamid Company | Alkyl esters of substituted 2-methyl-3-quinolinecarboxylic acid and quinoline-2,3-dicarboxylic acid |
| US4675432A (en) * | 1986-08-29 | 1987-06-23 | American Cyanamid Company | Method for the preparation of anilinofumarate |
| ES2019335B3 (es) * | 1986-08-29 | 1991-06-16 | American Cyanamid Co | Metodo para la preparacion de anilinofumarato y acido quinolein-2,3-dicarboxilico. |
-
1987
- 1987-10-01 US US07/101,453 patent/US4814486A/en not_active Expired - Lifetime
-
1988
- 1988-08-16 DE DE8888113254T patent/DE3878122T2/de not_active Expired - Fee Related
- 1988-08-16 EP EP88113254A patent/EP0309711B1/en not_active Expired - Lifetime
- 1988-08-16 ES ES198888113254T patent/ES2039525T3/es not_active Expired - Lifetime
- 1988-08-16 AT AT88113254T patent/ATE85321T1/de not_active IP Right Cessation
- 1988-08-24 IL IL87546A patent/IL87546A0/xx not_active IP Right Cessation
- 1988-09-27 RO RO1988135289A patent/RO101205B1/ro unknown
- 1988-09-27 JP JP63239872A patent/JP2703573B2/ja not_active Expired - Lifetime
- 1988-09-29 CA CA000578776A patent/CA1297126C/en not_active Expired - Lifetime
- 1988-09-29 DD DD88320260A patent/DD275453A5/de unknown
- 1988-09-30 BG BG085574A patent/BG47347A3/xx unknown
- 1988-09-30 AU AU23304/88A patent/AU611952B2/en not_active Ceased
- 1988-09-30 ZA ZA887372A patent/ZA887372B/xx unknown
- 1988-09-30 BR BR8805058A patent/BR8805058A/pt not_active IP Right Cessation
- 1988-09-30 CS CS886510A patent/CS275946B6/cs not_active IP Right Cessation
- 1988-09-30 HU HU885099A patent/HU200592B/hu not_active IP Right Cessation
- 1988-09-30 RU SU884356526A patent/RU1773259C/ru active
- 1988-09-30 KR KR1019880012832A patent/KR970006470B1/ko not_active Expired - Fee Related
- 1988-09-30 YU YU1837/88A patent/YU45062B/xx unknown
- 1988-09-30 IE IE296288A patent/IE63235B1/en not_active IP Right Cessation
- 1988-09-30 AR AR88312093A patent/AR244658A1/es active
-
1993
- 1993-02-04 GR GR920402264T patent/GR3006960T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2330488A (en) | 1989-04-06 |
| RO101205B1 (en) | 1992-01-28 |
| AR244658A1 (es) | 1993-11-30 |
| EP0309711B1 (en) | 1993-02-03 |
| JPH01113352A (ja) | 1989-05-02 |
| JP2703573B2 (ja) | 1998-01-26 |
| HU200592B (en) | 1990-07-28 |
| ATE85321T1 (de) | 1993-02-15 |
| HUT48573A (en) | 1989-06-28 |
| EP0309711A1 (en) | 1989-04-05 |
| BR8805058A (pt) | 1989-05-09 |
| DE3878122D1 (de) | 1993-03-18 |
| ES2039525T3 (es) | 1993-10-01 |
| CS8806510A2 (en) | 1991-07-16 |
| IE63235B1 (en) | 1995-04-05 |
| US4814486A (en) | 1989-03-21 |
| ZA887372B (en) | 1989-06-28 |
| KR890006570A (ko) | 1989-06-14 |
| GR3006960T3 (en, 2012) | 1993-06-30 |
| YU45062B (en) | 1991-06-30 |
| YU183788A (en) | 1990-02-28 |
| DD275453A5 (de) | 1990-01-24 |
| IE882962L (en) | 1989-04-01 |
| KR970006470B1 (ko) | 1997-04-28 |
| CS275946B6 (en) | 1992-03-18 |
| RU1773259C (ru) | 1992-10-30 |
| IL87546A0 (en) | 1989-01-31 |
| AU611952B2 (en) | 1991-06-27 |
| DE3878122T2 (de) | 1993-05-27 |
| BG47347A3 (en) | 1990-06-15 |
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