IE47709B1 - A process for the production of 4-aminobutyric acid or its derivatives - Google Patents
A process for the production of 4-aminobutyric acid or its derivativesInfo
- Publication number
- IE47709B1 IE47709B1 IE19/79A IE1979A IE47709B1 IE 47709 B1 IE47709 B1 IE 47709B1 IE 19/79 A IE19/79 A IE 19/79A IE 1979 A IE1979 A IE 1979A IE 47709 B1 IE47709 B1 IE 47709B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- compound
- acid
- nitrile
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229960003692 gamma aminobutyric acid Drugs 0.000 title abstract description 5
- -1 propionic acid compound Chemical class 0.000 claims abstract description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 32
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 14
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 150000002825 nitriles Chemical class 0.000 claims abstract description 5
- IVUOMFWNDGNLBJ-UHFFFAOYSA-N 4-azaniumyl-2-hydroxybutanoate Chemical compound NCCC(O)C(O)=O IVUOMFWNDGNLBJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 7
- 239000012346 acetyl chloride Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- LBHSPGVVTCCSOH-REOHCLBHSA-N (3s)-4-amino-3-hydroxy-4-oxobutanoic acid Chemical compound NC(=O)[C@@H](O)CC(O)=O LBHSPGVVTCCSOH-REOHCLBHSA-N 0.000 claims description 4
- 229960001230 asparagine Drugs 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 5
- 150000008065 acid anhydrides Chemical class 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000006188 syrup Substances 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IVUOMFWNDGNLBJ-VKHMYHEASA-N (2s)-4-amino-2-hydroxybutanoic acid Chemical compound NCC[C@H](O)C(O)=O IVUOMFWNDGNLBJ-VKHMYHEASA-N 0.000 description 5
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 4
- 229910003446 platinum oxide Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OGNSCSPNOLGXSM-VKHMYHEASA-N L-2,4-diaminobutyric acid Chemical compound NCC[C@H](N)C(O)=O OGNSCSPNOLGXSM-VKHMYHEASA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 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 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FUCKRCGERFLLHP-VIFPVBQESA-N (2s)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound NC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 FUCKRCGERFLLHP-VIFPVBQESA-N 0.000 description 1
- QVPLPSZGHFSYEQ-UHFFFAOYSA-N 2-amino-2-hydroxybutanoic acid Chemical compound CCC(N)(O)C(O)=O QVPLPSZGHFSYEQ-UHFFFAOYSA-N 0.000 description 1
- XKMGQNNRTFSLJU-UHFFFAOYSA-N 3-cyano-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)CC#N XKMGQNNRTFSLJU-UHFFFAOYSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- VZUHQRBBQSLSHS-SSZFMOIBSA-N Isoimide Chemical group C1=CC(Br)=CC=C1\N=C/1C(CCCC2)=C2C(=O)O\1 VZUHQRBBQSLSHS-SSZFMOIBSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229960003767 alanine Drugs 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- VCJIGSOOIYBSFA-UHFFFAOYSA-N azido formate Chemical compound [N-]=[N+]=NOC=O VCJIGSOOIYBSFA-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229930190553 ribostamycin Natural products 0.000 description 1
- 229960003485 ribostamycin Drugs 0.000 description 1
- NSKGQURZWSPSBC-NLZFXWNVSA-N ribostamycin Chemical compound N[C@H]1[C@H](O)[C@@H](O)[C@H](CN)O[C@@H]1O[C@@H]1[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](CO)O2)O)[C@H](O)[C@@H](N)C[C@H]1N NSKGQURZWSPSBC-NLZFXWNVSA-N 0.000 description 1
- NSKGQURZWSPSBC-UHFFFAOYSA-N ribostamycin A Natural products NC1C(O)C(O)C(CN)OC1OC1C(OC2C(C(O)C(CO)O2)O)C(O)C(N)CC1N NSKGQURZWSPSBC-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 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
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP614278A JPS54100316A (en) | 1978-01-25 | 1978-01-25 | Preparation of derivative of aminobutyric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE790019L IE790019L (en) | 1979-07-25 |
| IE47709B1 true IE47709B1 (en) | 1984-05-30 |
Family
ID=11630256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE19/79A IE47709B1 (en) | 1978-01-25 | 1979-01-04 | A process for the production of 4-aminobutyric acid or its derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4290972A (en, 2012) |
| JP (1) | JPS54100316A (en, 2012) |
| BE (1) | BE873659A (en, 2012) |
| CA (1) | CA1119614A (en, 2012) |
| CH (1) | CH644095A5 (en, 2012) |
| DE (1) | DE2902292C2 (en, 2012) |
| DK (1) | DK149607C (en, 2012) |
| ES (1) | ES477120A1 (en, 2012) |
| FR (1) | FR2415623A1 (en, 2012) |
| GR (1) | GR64399B (en, 2012) |
| HU (1) | HU180506B (en, 2012) |
| IE (1) | IE47709B1 (en, 2012) |
| IT (1) | IT1120732B (en, 2012) |
| NL (1) | NL7900336A (en, 2012) |
| PT (1) | PT69122A (en, 2012) |
| SE (1) | SE451326B (en, 2012) |
| SU (1) | SU902662A3 (en, 2012) |
| YU (1) | YU41142B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892961A (en) * | 1985-07-31 | 1990-01-09 | Sumitomo Pharmaceuticals Company, Limited | Amino acid derivatives, and their production |
| US5132451A (en) * | 1989-08-25 | 1992-07-21 | Warner-Lambert Company | Process for cyclic amino acid anticonvulsant compounds |
| US5637767A (en) * | 1995-06-07 | 1997-06-10 | Warner-Lambert Company | Method of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| KR100491748B1 (ko) * | 1996-09-13 | 2005-05-27 | 니폰 가야꾸 가부시끼가이샤 | 광학활성 에리스로-3-아미노-2-히드록시부티르산에스테르류및 해당 부티르산류의 제조방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417749A (en) * | 1943-12-23 | 1947-03-18 | Eastman Kodak Co | Preparation of olefinic nitriles by dehydration with acetic anhydride |
| US2839547A (en) * | 1955-07-30 | 1958-06-17 | Inventa Ag | Process for the production of aminocarboxylic acids |
| US3031490A (en) * | 1958-02-28 | 1962-04-24 | Fmc Corp | Process for the preparation of alpha-amino acids |
| US3062869A (en) * | 1958-11-07 | 1962-11-06 | Fmc Corp | Reduction of nitriles |
| DE1085165B (de) * | 1959-03-18 | 1960-07-14 | Basf Ag | Verfahren zum Hydrieren von Nitro-, Nitroso-, Isonitroso-, Cyan- und/oder aromatischgebundene Aminogruppen enthaltenden Kohlenstoffverbindungen |
| US3217027A (en) * | 1961-11-02 | 1965-11-09 | Dow Chemical Co | Purification of cyanoaliphatic acids |
| US3354203A (en) * | 1963-11-04 | 1967-11-21 | Dow Chemical Co | Preparation of omega-amino acids |
| US3928445A (en) * | 1973-12-26 | 1975-12-23 | Allied Chem | Synthesis of 2-halo-5-cyano alkyl valerate |
-
1978
- 1978-01-25 JP JP614278A patent/JPS54100316A/ja active Granted
-
1979
- 1979-01-04 IE IE19/79A patent/IE47709B1/en not_active IP Right Cessation
- 1979-01-15 GR GR58092A patent/GR64399B/el unknown
- 1979-01-16 NL NL7900336A patent/NL7900336A/xx not_active Application Discontinuation
- 1979-01-19 SE SE7900518A patent/SE451326B/sv not_active IP Right Cessation
- 1979-01-22 IT IT09322/79A patent/IT1120732B/it active
- 1979-01-22 DE DE2902292A patent/DE2902292C2/de not_active Expired
- 1979-01-23 BE BE193043A patent/BE873659A/xx not_active IP Right Cessation
- 1979-01-24 PT PT7969122A patent/PT69122A/pt unknown
- 1979-01-24 ES ES477120A patent/ES477120A1/es not_active Expired
- 1979-01-24 CH CH71479A patent/CH644095A5/de not_active IP Right Cessation
- 1979-01-24 DK DK30679A patent/DK149607C/da not_active IP Right Cessation
- 1979-01-24 SU SU792714801A patent/SU902662A3/ru active
- 1979-01-24 FR FR7902579A patent/FR2415623A1/fr active Granted
- 1979-01-24 CA CA000320226A patent/CA1119614A/en not_active Expired
- 1979-01-25 YU YU168/79A patent/YU41142B/xx unknown
- 1979-01-25 HU HU79ME2243A patent/HU180506B/hu not_active IP Right Cessation
- 1979-11-09 US US06/092,940 patent/US4290972A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1119614A (en) | 1982-03-09 |
| SU902662A3 (ru) | 1982-01-30 |
| FR2415623B1 (en, 2012) | 1982-09-17 |
| NL7900336A (nl) | 1979-07-27 |
| US4290972A (en) | 1981-09-22 |
| JPS54100316A (en) | 1979-08-08 |
| HU180506B (en) | 1983-03-28 |
| IT7909322A0 (it) | 1979-01-22 |
| YU16879A (en) | 1982-10-31 |
| CH644095A5 (de) | 1984-07-13 |
| BE873659A (fr) | 1979-05-16 |
| SE451326B (sv) | 1987-09-28 |
| GR64399B (en) | 1980-03-21 |
| JPS6146469B2 (en, 2012) | 1986-10-14 |
| IE790019L (en) | 1979-07-25 |
| DK30679A (da) | 1979-07-26 |
| YU41142B (en) | 1986-12-31 |
| SE7900518L (sv) | 1979-07-26 |
| DK149607C (da) | 1987-03-16 |
| FR2415623A1 (fr) | 1979-08-24 |
| PT69122A (en) | 1979-02-01 |
| DK149607B (da) | 1986-08-11 |
| DE2902292A1 (de) | 1979-07-26 |
| DE2902292C2 (de) | 1982-08-05 |
| ES477120A1 (es) | 1979-10-16 |
| IT1120732B (it) | 1986-03-26 |
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