FI68809C - Foerfarande foer framstaellning av p-hydroxifenylglycin - Google Patents
Foerfarande foer framstaellning av p-hydroxifenylglycin Download PDFInfo
- Publication number
- FI68809C FI68809C FI782241A FI782241A FI68809C FI 68809 C FI68809 C FI 68809C FI 782241 A FI782241 A FI 782241A FI 782241 A FI782241 A FI 782241A FI 68809 C FI68809 C FI 68809C
- Authority
- FI
- Finland
- Prior art keywords
- water
- hydroxyphenylglycine
- hydroxifenylglycin
- yield
- mixture
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KEKOOFQAJLWTEA-UHFFFAOYSA-N O.[Na].OC(=O)C(O)C1=CC=C(O)C=C1 Chemical compound O.[Na].OC(=O)C(O)C1=CC=C(O)C=C1 KEKOOFQAJLWTEA-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AYKYOOPFBCOXSL-UHFFFAOYSA-N (4-hydroxyphenyl)acetonitrile Chemical compound OC1=CC=C(CC#N)C=C1 AYKYOOPFBCOXSL-UHFFFAOYSA-N 0.000 description 1
- VGXPXHIRRYBSHZ-UHFFFAOYSA-N 2-amino-2-(4-hydroxyphenyl)acetic acid Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1.OC(=O)C(N)C1=CC=C(O)C=C1 VGXPXHIRRYBSHZ-UHFFFAOYSA-N 0.000 description 1
- NTYZULLIPJQEEB-UHFFFAOYSA-N 2-hydroxy-2-(4-hydroxyphenyl)acetic acid;sodium Chemical compound [Na].OC(=O)C(O)C1=CC=C(O)C=C1 NTYZULLIPJQEEB-UHFFFAOYSA-N 0.000 description 1
- YHXHKYRQLYQUIH-UHFFFAOYSA-N 4-hydroxymandelic acid Chemical compound OC(=O)C(O)C1=CC=C(O)C=C1 YHXHKYRQLYQUIH-UHFFFAOYSA-N 0.000 description 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 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
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
- 229960003022 amoxicillin Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- HPQVZCCKGRTPLU-UHFFFAOYSA-M sodium;2-hydroxy-2-(4-hydroxyphenyl)acetate Chemical compound [Na+].[O-]C(=O)C(O)C1=CC=C(O)C=C1 HPQVZCCKGRTPLU-UHFFFAOYSA-M 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8069/76A GB1576334A (en) | 1977-05-26 | 1977-05-26 | N-alkyl and n,n-dialkyl derivatives thereof process for the manufacture of p-hydroxyphenylglycine and |
ZA00782655A ZA782655B (en) | 1977-05-26 | 1978-05-09 | Salt |
AU37924/78A AU520192B2 (en) | 1977-05-26 | 1978-07-11 | A process forthe manufacture ofp-hydroxyphenylglycine |
DK311878A DK158837C (da) | 1977-05-26 | 1978-07-11 | Fremgangsmaade til fremstilling af p-hydroxyphenylglycin. |
ZA00783965A ZA783965B (en) | 1977-05-26 | 1978-07-11 | A process for the manufacture of p-hydroxy-phenylglycine |
SE7807719A SE439482B (sv) | 1977-05-26 | 1978-07-11 | Sett att framstella p-hydroxifenylglycin |
FI782241A FI68809C (fi) | 1977-05-26 | 1978-07-13 | Foerfarande foer framstaellning av p-hydroxifenylglycin |
BE189307A BE869021A (fr) | 1977-05-26 | 1978-07-14 | Procede pour produire la p-hydroxyphenylglycine |
DE19782831118 DE2831118C2 (de) | 1977-05-26 | 1978-07-14 | Verfahren zur herstellung von p-hydroxyphenylglycin und seiner n-alkyl- und n,n-dialkylderivate |
NLAANVRAGE7807630,A NL187745C (nl) | 1977-05-26 | 1978-07-17 | Werkwijze voor de bereiding van p-hydroxyfenylglycine of een n-alkyl- of n.n-dialkylderivaat daarvan. |
FR7821174A FR2431485A1 (fr) | 1977-05-26 | 1978-07-17 | Procede pour produire la p-hydroxyphenylglycine |
LU79985A LU79985A1 (fr) | 1977-05-26 | 1978-07-17 | Procede pour produire la p-hydroxyphenylglycine |
IT2580078A IT1158888B (it) | 1977-05-26 | 1978-07-17 | Procedimento per la fabbricazione di p-idrossifenilglicina e suoi derivati |
JP8684178A JPS5515414A (en) | 1977-05-26 | 1978-07-18 | Manufacture of pphydroxyphenylglycine or its nnalkyl or n*nndialkyl derivative |
CH773278A CH634825A5 (de) | 1977-05-26 | 1978-07-18 | Verfahren zur herstellung von p-hydroxyphenylglycin oder dessen n-alkyl- bzw. n,n-dialkylderivaten. |
PT68324A PT68324A (en) | 1977-05-26 | 1978-07-19 | Process for preparing p-hydroxyphenylglycine or an n-alkyl or n,n-dialkyl derivative thereof |
US06/215,872 US4350826A (en) | 1977-05-26 | 1980-12-12 | Process for preparing p-hydroxy phenylglycine |
Applications Claiming Priority (34)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB806976 | 1977-05-26 | ||
GB8069/76A GB1576334A (en) | 1977-05-26 | 1977-05-26 | N-alkyl and n,n-dialkyl derivatives thereof process for the manufacture of p-hydroxyphenylglycine and |
ZA00782655A ZA782655B (en) | 1977-05-26 | 1978-05-09 | Salt |
ZA7802655 | 1978-05-09 | ||
ZA7803965 | 1978-07-11 | ||
SE7807719 | 1978-07-11 | ||
AU3792478 | 1978-07-11 | ||
AU37924/78A AU520192B2 (en) | 1977-05-26 | 1978-07-11 | A process forthe manufacture ofp-hydroxyphenylglycine |
DK311878 | 1978-07-11 | ||
DK311878A DK158837C (da) | 1977-05-26 | 1978-07-11 | Fremgangsmaade til fremstilling af p-hydroxyphenylglycin. |
SE7807719A SE439482B (sv) | 1977-05-26 | 1978-07-11 | Sett att framstella p-hydroxifenylglycin |
ZA00783965A ZA783965B (en) | 1977-05-26 | 1978-07-11 | A process for the manufacture of p-hydroxy-phenylglycine |
FI782241A FI68809C (fi) | 1977-05-26 | 1978-07-13 | Foerfarande foer framstaellning av p-hydroxifenylglycin |
FI782241 | 1978-07-13 | ||
BE189307A BE869021A (fr) | 1977-05-26 | 1978-07-14 | Procede pour produire la p-hydroxyphenylglycine |
DE19782831118 DE2831118C2 (de) | 1977-05-26 | 1978-07-14 | Verfahren zur herstellung von p-hydroxyphenylglycin und seiner n-alkyl- und n,n-dialkylderivate |
BE189307 | 1978-07-14 | ||
DE2831118 | 1978-07-14 | ||
LU79985 | 1978-07-17 | ||
LU79985A LU79985A1 (fr) | 1977-05-26 | 1978-07-17 | Procede pour produire la p-hydroxyphenylglycine |
IT2580078 | 1978-07-17 | ||
NL7807630 | 1978-07-17 | ||
FR7821174 | 1978-07-17 | ||
FR7821174A FR2431485A1 (fr) | 1977-05-26 | 1978-07-17 | Procede pour produire la p-hydroxyphenylglycine |
NLAANVRAGE7807630,A NL187745C (nl) | 1977-05-26 | 1978-07-17 | Werkwijze voor de bereiding van p-hydroxyfenylglycine of een n-alkyl- of n.n-dialkylderivaat daarvan. |
IT2580078A IT1158888B (it) | 1977-05-26 | 1978-07-17 | Procedimento per la fabbricazione di p-idrossifenilglicina e suoi derivati |
JP8684178 | 1978-07-18 | ||
CH773278A CH634825A5 (de) | 1977-05-26 | 1978-07-18 | Verfahren zur herstellung von p-hydroxyphenylglycin oder dessen n-alkyl- bzw. n,n-dialkylderivaten. |
CH773278 | 1978-07-18 | ||
JP8684178A JPS5515414A (en) | 1977-05-26 | 1978-07-18 | Manufacture of pphydroxyphenylglycine or its nnalkyl or n*nndialkyl derivative |
PT6832478 | 1978-07-19 | ||
PT68324A PT68324A (en) | 1977-05-26 | 1978-07-19 | Process for preparing p-hydroxyphenylglycine or an n-alkyl or n,n-dialkyl derivative thereof |
US21587280 | 1980-12-12 | ||
US06/215,872 US4350826A (en) | 1977-05-26 | 1980-12-12 | Process for preparing p-hydroxy phenylglycine |
Publications (3)
Publication Number | Publication Date |
---|---|
FI782241A FI782241A (fi) | 1980-01-14 |
FI68809B FI68809B (fi) | 1985-07-31 |
FI68809C true FI68809C (fi) | 1985-11-11 |
Family
ID=38922765
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI782241A FI68809C (fi) | 1977-05-26 | 1978-07-13 | Foerfarande foer framstaellning av p-hydroxifenylglycin |
Country Status (16)
Country | Link |
---|---|
US (1) | US4350826A (ru) |
JP (1) | JPS5515414A (ru) |
AU (1) | AU520192B2 (ru) |
BE (1) | BE869021A (ru) |
CH (1) | CH634825A5 (ru) |
DE (1) | DE2831118C2 (ru) |
DK (1) | DK158837C (ru) |
FI (1) | FI68809C (ru) |
FR (1) | FR2431485A1 (ru) |
GB (1) | GB1576334A (ru) |
IT (1) | IT1158888B (ru) |
LU (1) | LU79985A1 (ru) |
NL (1) | NL187745C (ru) |
PT (1) | PT68324A (ru) |
SE (1) | SE439482B (ru) |
ZA (2) | ZA782655B (ru) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2427322A1 (fr) * | 1979-06-15 | 1979-12-28 | Hoechst France | Parahydroxymandelate de sodium racemique cristallise, son procede de preparation et son application a la preparation du paraformylphenolate de sodium cristallise |
FR2518540A1 (fr) * | 1981-12-23 | 1983-06-24 | Hoechst France | Dimethylamino-2 parahydroxyphenyl-2 acetate de sodium, son procede de preparation et son application a la fabrication du cyanure de parahydroxybenzyle |
DE3531067A1 (de) * | 1985-08-30 | 1987-03-05 | Dynamit Nobel Ag | Verfahren zur herstellung von 3-aminoacrylsaeureestern |
JP3762980B2 (ja) * | 2000-11-17 | 2006-04-05 | 独立行政法人産業技術総合研究所 | アミノ基導入法及びアミノ酸の合成方法 |
JP3605635B2 (ja) * | 2000-12-11 | 2004-12-22 | 独立行政法人産業技術総合研究所 | アミノ基導入方法及びアミノ酸化合物合成方法 |
US9512061B2 (en) | 2011-12-19 | 2016-12-06 | Basf Se | Process for the preparation of racemic alpha-amino acids |
CA2856957A1 (en) * | 2011-12-19 | 2013-06-27 | Basf Se | Process for preparing racemic .alpha.-amino acids |
CN104370765A (zh) * | 2013-08-13 | 2015-02-25 | 成都化工股份有限公司 | D-苯甘氨酸和dl-苯甘氨酸的合成方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH369468A (de) * | 1957-10-17 | 1963-05-31 | Hoffmann La Roche | Verfahren zur Herstellung von a-tert.-Aminoessigsäuren |
GB1353612A (en) * | 1970-07-11 | 1974-05-22 | Sterling Winthrop Group Ltd | Process for the preparation of a glycine derivative |
GB1371896A (en) * | 1970-10-15 | 1974-10-30 | Beecham Group Ltd | Hydroxyaryl amino acids |
DE2115551C3 (de) * | 1971-03-31 | 1980-01-10 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verfahren zur Herstellung von aromatischen Hydroxyaldehyden |
FR2205895A5 (en) * | 1972-11-08 | 1974-05-31 | Aries Robert | Alpha-amino-hydroxyphenylacetic acids prepn. - by cheap, three-stage process from hydroxyphenylglyoxylic acids via mandelic acids |
US3860631A (en) * | 1973-12-06 | 1975-01-14 | Smithkline Corp | Process for the preparation of n-acyl-2- and 4-hydroxyphenylglycines |
CH614928A5 (ru) * | 1975-09-12 | 1979-12-28 | Nobel Hoechst Chimie | |
SE441524B (sv) * | 1978-05-19 | 1985-10-14 | Ici Ltd | Fast natrium- eller kalium-p-hydroximandelat-monohydrat och sett for dess framstellning |
-
1977
- 1977-05-26 GB GB8069/76A patent/GB1576334A/en not_active Expired
-
1978
- 1978-05-09 ZA ZA00782655A patent/ZA782655B/xx unknown
- 1978-07-11 DK DK311878A patent/DK158837C/da not_active IP Right Cessation
- 1978-07-11 SE SE7807719A patent/SE439482B/sv not_active IP Right Cessation
- 1978-07-11 ZA ZA00783965A patent/ZA783965B/xx unknown
- 1978-07-11 AU AU37924/78A patent/AU520192B2/en not_active Expired
- 1978-07-13 FI FI782241A patent/FI68809C/fi not_active IP Right Cessation
- 1978-07-14 BE BE189307A patent/BE869021A/xx not_active IP Right Cessation
- 1978-07-14 DE DE19782831118 patent/DE2831118C2/de not_active Expired
- 1978-07-17 LU LU79985A patent/LU79985A1/fr unknown
- 1978-07-17 IT IT2580078A patent/IT1158888B/it active
- 1978-07-17 NL NLAANVRAGE7807630,A patent/NL187745C/xx not_active IP Right Cessation
- 1978-07-17 FR FR7821174A patent/FR2431485A1/fr active Granted
- 1978-07-18 CH CH773278A patent/CH634825A5/de not_active IP Right Cessation
- 1978-07-18 JP JP8684178A patent/JPS5515414A/ja active Granted
- 1978-07-19 PT PT68324A patent/PT68324A/pt unknown
-
1980
- 1980-12-12 US US06/215,872 patent/US4350826A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DK158837B (da) | 1990-07-23 |
PT68324A (en) | 1978-08-01 |
IT1158888B (it) | 1987-02-25 |
DK158837C (da) | 1990-12-24 |
SE439482B (sv) | 1985-06-17 |
DE2831118C2 (de) | 1989-11-02 |
NL7807630A (nl) | 1980-01-21 |
CH634825A5 (de) | 1983-02-28 |
ZA782655B (en) | 1979-05-30 |
ZA783965B (en) | 1979-12-27 |
GB1576334A (en) | 1980-10-08 |
DK311878A (da) | 1980-01-12 |
AU520192B2 (en) | 1982-01-21 |
JPS5515414A (en) | 1980-02-02 |
NL187745B (nl) | 1991-08-01 |
FI68809B (fi) | 1985-07-31 |
JPS6256859B2 (ru) | 1987-11-27 |
SE7807719L (sv) | 1980-01-12 |
FR2431485A1 (fr) | 1980-02-15 |
NL187745C (nl) | 1992-01-02 |
FI782241A (fi) | 1980-01-14 |
LU79985A1 (fr) | 1980-02-14 |
DE2831118A1 (de) | 1980-01-24 |
BE869021A (fr) | 1979-01-15 |
FR2431485B1 (ru) | 1983-11-18 |
IT7825800A0 (it) | 1978-07-17 |
US4350826A (en) | 1982-09-21 |
AU3792478A (en) | 1980-01-17 |
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