DE2550121C2 - Verfahren zur Herstellung von Alkalisalzen von 2-Deutero-3-fluor-DL-alanin - Google Patents
Verfahren zur Herstellung von Alkalisalzen von 2-Deutero-3-fluor-DL-alaninInfo
- Publication number
- DE2550121C2 DE2550121C2 DE2550121A DE2550121A DE2550121C2 DE 2550121 C2 DE2550121 C2 DE 2550121C2 DE 2550121 A DE2550121 A DE 2550121A DE 2550121 A DE2550121 A DE 2550121A DE 2550121 C2 DE2550121 C2 DE 2550121C2
- Authority
- DE
- Germany
- Prior art keywords
- deutero
- fluoropropionate
- ammonia
- fluoro
- dihydroxy
- 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
Links
- UYTSRQMXRROFPU-VMNATFBRSA-N 2-amino-2-deuterio-3-fluoropropanoic acid Chemical class FCC(N)([2H])C(O)=O UYTSRQMXRROFPU-VMNATFBRSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 150000001447 alkali salts Chemical class 0.000 title claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 48
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- UORVGPXVDQYIDP-FIBGUPNXSA-N trideuterioborane Chemical compound [2H]B([2H])[2H] UORVGPXVDQYIDP-FIBGUPNXSA-N 0.000 claims description 14
- AQVIWPOYCZKUAH-UHFFFAOYSA-N 2-amino-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)(N)C(O)=O AQVIWPOYCZKUAH-UHFFFAOYSA-N 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- -1 sodium boron deuteride Chemical group 0.000 claims description 5
- CXABZTLXNODUTD-UHFFFAOYSA-N 3-fluoropyruvic acid Chemical compound OC(=O)C(=O)CF CXABZTLXNODUTD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 235000011114 ammonium hydroxide Nutrition 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 229910001868 water Inorganic materials 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- RLRSEGOXKMMOLT-UHFFFAOYSA-N 3-fluoro-2,2-dihydroxypropanoic acid Chemical compound OC(=O)C(O)(O)CF RLRSEGOXKMMOLT-UHFFFAOYSA-N 0.000 description 7
- 150000002466 imines Chemical class 0.000 description 7
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- UYTSRQMXRROFPU-MYSWAXPFSA-N (2r)-2-amino-2-deuterio-3-fluoropropanoic acid Chemical compound FC[C@@](N)([2H])C(O)=O UYTSRQMXRROFPU-MYSWAXPFSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 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
- 150000001412 amines Chemical class 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- AMDBHIRLAIRLGJ-UHFFFAOYSA-M lithium;3-fluoro-2,2-dihydroxypropanoate Chemical compound [Li+].FCC(O)(O)C([O-])=O AMDBHIRLAIRLGJ-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical group [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- UYIAUFVPRSSBGY-VMNATFBRSA-N 2-deuterio-3-fluoro-2-hydroxypropanoic acid Chemical compound FCC(O)([2H])C(O)=O UYIAUFVPRSSBGY-VMNATFBRSA-N 0.000 description 1
- OSYXANRNDYBMOU-UHFFFAOYSA-N 3-fluoro-2-iminopropanoic acid Chemical compound OC(=O)C(=N)CF OSYXANRNDYBMOU-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FQRWQIIGGDXUPV-UHFFFAOYSA-M FCC(=O)C(=O)O[K] Chemical compound FCC(=O)C(=O)O[K] FQRWQIIGGDXUPV-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000010716 Vigna mungo Nutrition 0.000 description 1
- 244000042295 Vigna mungo Species 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- APJSJVCWIQYDRG-UHFFFAOYSA-N diethyl 2-fluoro-3-oxobutanedioate;sodium Chemical compound [Na].CCOC(=O)C(F)C(=O)C(=O)OCC APJSJVCWIQYDRG-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229950010030 dl-alanine Drugs 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- HPKZHKRTMMLVBQ-UHFFFAOYSA-N fluoro propanoate Chemical compound CCC(=O)OF HPKZHKRTMMLVBQ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- RRYOTPCFMILDDZ-UHFFFAOYSA-M lithium;3-fluoro-2-oxopropanoate;hydrate Chemical compound [Li+].O.[O-]C(=O)C(=O)CF RRYOTPCFMILDDZ-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- YEXRRCHQJDSEJI-UHFFFAOYSA-M sodium;3-fluoro-2-oxopropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CF YEXRRCHQJDSEJI-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008673 vomiting Effects 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/522,185 US3972921A (en) | 1974-11-08 | 1974-11-08 | Synthesis of racemic 2-deutero-3-fluoro-alanine and its salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2550121A1 DE2550121A1 (de) | 1976-05-20 |
| DE2550121C2 true DE2550121C2 (de) | 1984-08-16 |
Family
ID=24079796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2550121A Expired DE2550121C2 (de) | 1974-11-08 | 1975-11-07 | Verfahren zur Herstellung von Alkalisalzen von 2-Deutero-3-fluor-DL-alanin |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3972921A (en, 2012) |
| JP (1) | JPS5926614B2 (en, 2012) |
| AR (1) | AR208722A1 (en, 2012) |
| AT (1) | AT344136B (en, 2012) |
| BE (1) | BE835358A (en, 2012) |
| CA (1) | CA1053697A (en, 2012) |
| CH (1) | CH622772A5 (en, 2012) |
| CS (1) | CS199501B2 (en, 2012) |
| DD (1) | DD125839A5 (en, 2012) |
| DE (1) | DE2550121C2 (en, 2012) |
| DK (1) | DK474375A (en, 2012) |
| ES (1) | ES442154A1 (en, 2012) |
| FI (1) | FI752919A7 (en, 2012) |
| FR (1) | FR2290418A1 (en, 2012) |
| GB (1) | GB1480886A (en, 2012) |
| HU (1) | HU172273B (en, 2012) |
| IE (1) | IE42060B1 (en, 2012) |
| IT (1) | IT1048054B (en, 2012) |
| LU (1) | LU73734A1 (en, 2012) |
| NL (1) | NL7512383A (en, 2012) |
| NO (1) | NO147671C (en, 2012) |
| PL (1) | PL102608B1 (en, 2012) |
| SE (1) | SE7511734L (en, 2012) |
| SU (1) | SU626689A3 (en, 2012) |
| YU (1) | YU39750B (en, 2012) |
| ZA (1) | ZA757012B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4028405A (en) * | 1974-10-15 | 1977-06-07 | Merck & Co., Inc. | Fluorinated amino acids |
| US4049708A (en) * | 1976-03-04 | 1977-09-20 | Merck & Co., Inc. | Fluorodesulfurization of alkyl mercaptans or alkyl dithianes |
| NZ194348A (en) * | 1979-07-26 | 1982-09-14 | Merrell Toraude & Co | Fluorinated methyl-beta-alanine derivatives and pharmaceutical compositions |
| JPS56113733A (en) * | 1979-12-29 | 1981-09-07 | Daikin Ind Ltd | 3-substituted-3-fluoropyruvic acid, its ester, salt and preparation thereof |
| US4582931A (en) * | 1984-12-24 | 1986-04-15 | Merck & Co., Inc. | Preparation of 2-Deutero-D-serine |
| US5254730A (en) * | 1992-01-14 | 1993-10-19 | Kilgore James L | Production of amino acids and amino acid derivatives bearing isotopic hydrogen labels |
| FR2707309B1 (fr) * | 1993-07-09 | 1995-08-11 | Trefileurope France Sa | Câble de levage. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610212A (en) * | 1950-04-24 | 1952-09-09 | Gen Mills Inc | Synthesis of amino acids |
| US2839547A (en) * | 1955-07-30 | 1958-06-17 | Inventa Ag | Process for the production of aminocarboxylic acids |
| JPS4936389B1 (en, 2012) * | 1969-03-03 | 1974-09-30 | ||
| US3585361A (en) * | 1969-06-18 | 1971-06-15 | Nordson Corp | Supply system for heating and dispensing molten thermoplastic material |
| JPS4841007B1 (en, 2012) * | 1970-10-22 | 1973-12-04 | ||
| JPS5225415B2 (en, 2012) * | 1972-01-17 | 1977-07-07 | ||
| JPS4935435A (en, 2012) * | 1972-08-09 | 1974-04-02 |
-
1974
- 1974-11-08 US US05/522,185 patent/US3972921A/en not_active Expired - Lifetime
-
1975
- 1975-10-20 SE SE7511734A patent/SE7511734L/xx unknown
- 1975-10-20 FI FI752919A patent/FI752919A7/fi not_active Application Discontinuation
- 1975-10-22 NL NL7512383A patent/NL7512383A/xx not_active Application Discontinuation
- 1975-10-22 DK DK474375A patent/DK474375A/da not_active Application Discontinuation
- 1975-10-23 NO NO753561A patent/NO147671C/no unknown
- 1975-10-27 YU YU2722/75A patent/YU39750B/xx unknown
- 1975-10-27 CA CA238,618A patent/CA1053697A/en not_active Expired
- 1975-10-27 GB GB44182/75A patent/GB1480886A/en not_active Expired
- 1975-10-28 ES ES442154A patent/ES442154A1/es not_active Expired
- 1975-10-28 AR AR260981A patent/AR208722A1/es active
- 1975-10-31 IT IT52036/75A patent/IT1048054B/it active
- 1975-10-31 SU SU752185056A patent/SU626689A3/ru active
- 1975-10-31 HU HU75ME00001914A patent/HU172273B/hu unknown
- 1975-11-04 CS CS757421A patent/CS199501B2/cs unknown
- 1975-11-04 AT AT838775A patent/AT344136B/de not_active IP Right Cessation
- 1975-11-05 FR FR7533779A patent/FR2290418A1/fr active Granted
- 1975-11-05 IE IE2407/75A patent/IE42060B1/en unknown
- 1975-11-05 DD DD189260A patent/DD125839A5/xx unknown
- 1975-11-06 PL PL1975184521A patent/PL102608B1/pl unknown
- 1975-11-06 LU LU73734A patent/LU73734A1/xx unknown
- 1975-11-06 CH CH1435875A patent/CH622772A5/de not_active IP Right Cessation
- 1975-11-07 DE DE2550121A patent/DE2550121C2/de not_active Expired
- 1975-11-07 JP JP50133150A patent/JPS5926614B2/ja not_active Expired
- 1975-11-07 BE BE161682A patent/BE835358A/xx not_active IP Right Cessation
- 1975-11-07 ZA ZA757012A patent/ZA757012B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7512383A (nl) | 1976-05-11 |
| CH622772A5 (en, 2012) | 1981-04-30 |
| IE42060L (en) | 1976-05-08 |
| AT344136B (de) | 1978-07-10 |
| FI752919A7 (en, 2012) | 1976-05-09 |
| FR2290418B1 (en, 2012) | 1979-01-05 |
| DD125839A5 (en, 2012) | 1977-05-25 |
| YU39750B (en) | 1985-04-30 |
| NO753561L (en, 2012) | 1976-05-11 |
| SU626689A3 (ru) | 1978-09-30 |
| NO147671B (no) | 1983-02-14 |
| DK474375A (da) | 1976-05-09 |
| BE835358A (fr) | 1976-05-07 |
| GB1480886A (en) | 1977-07-27 |
| CA1053697A (en) | 1979-05-01 |
| IT1048054B (it) | 1980-11-20 |
| FR2290418A1 (fr) | 1976-06-04 |
| CS199501B2 (en) | 1980-07-31 |
| ATA838775A (de) | 1977-11-15 |
| JPS5170722A (en) | 1976-06-18 |
| DE2550121A1 (de) | 1976-05-20 |
| LU73734A1 (en, 2012) | 1976-09-06 |
| US3972921A (en) | 1976-08-03 |
| PL102608B1 (pl) | 1979-04-30 |
| JPS5926614B2 (ja) | 1984-06-29 |
| AR208722A1 (es) | 1977-02-28 |
| IE42060B1 (en) | 1980-05-21 |
| HU172273B (hu) | 1978-07-28 |
| ES442154A1 (es) | 1977-07-01 |
| ZA757012B (en) | 1977-06-29 |
| NO147671C (no) | 1983-05-25 |
| AU8605675A (en) | 1977-05-05 |
| SE7511734L (sv) | 1976-05-10 |
| YU272275A (en) | 1982-02-28 |
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