IE46246B1 - 3-substituted 1,2,4-triazines and their preparation - Google Patents
3-substituted 1,2,4-triazines and their preparationInfo
- Publication number
- IE46246B1 IE46246B1 IE115/78A IE11578A IE46246B1 IE 46246 B1 IE46246 B1 IE 46246B1 IE 115/78 A IE115/78 A IE 115/78A IE 11578 A IE11578 A IE 11578A IE 46246 B1 IE46246 B1 IE 46246B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- phenyl
- compound
- formula
- methyl
- Prior art date
Links
- -1 3-substituted 1,2,4-triazines Chemical class 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- JHKIHARISAHZAK-UHFFFAOYSA-N 2-hydrazinylethanamine Chemical compound NCCNN JHKIHARISAHZAK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002825 nitriles Chemical class 0.000 claims abstract description 12
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000005864 Sulphur Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- QQZDRBLYFGVUER-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NCCNN1 QQZDRBLYFGVUER-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- DRONDEZXOJEUGU-UHFFFAOYSA-N 2,3-diphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(C#N)CC1=CC=CC=C1 DRONDEZXOJEUGU-UHFFFAOYSA-N 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- 230000001035 methylating effect Effects 0.000 claims description 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000000397 acetylating effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 abstract description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000012634 fragment Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 230000000049 anti-anxiety effect Effects 0.000 description 6
- 230000001430 anti-depressive effect Effects 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000003246 corticosteroid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical class C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical class C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- YQUAOWNIIVZNAK-UHFFFAOYSA-N 3-(1,2-diphenylethyl)-1,2,5,6-tetrahydro-1,2,4-triazine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CC(C=1C=CC=CC=1)C1=NNCCN1 YQUAOWNIIVZNAK-UHFFFAOYSA-N 0.000 description 2
- ACRWYXSKEHUQDB-UHFFFAOYSA-N 3-phenylpropionitrile Chemical compound N#CCCC1=CC=CC=C1 ACRWYXSKEHUQDB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MKVBVTOSWPBSNC-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,2,4-triazine Chemical class C1NNC=CN1 MKVBVTOSWPBSNC-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- GFGDAKKRLNCZIC-UHFFFAOYSA-N 1-[3-(1,2-diphenylethyl)-1-methyl-5,6-dihydro-1,2,4-triazin-4-yl]ethanone;hydrochloride Chemical compound Cl.CN1CCN(C(C)=O)C(C(CC=2C=CC=CC=2)C=2C=CC=CC=2)=N1 GFGDAKKRLNCZIC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- IJSQKWIWHJHNGV-UHFFFAOYSA-N 3-(naphthalen-2-ylmethyl)-1,2,5,6-tetrahydro-1,2,4-triazine;hydrochloride Chemical compound Cl.C=1C=C2C=CC=CC2=CC=1CC1=NNCCN1 IJSQKWIWHJHNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012754 cardiac puncture Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/761,177 US4071684A (en) | 1977-01-21 | 1977-01-21 | Process for producing 3-substituted 1,2,4-triazines |
| US05/803,927 US4263295A (en) | 1977-06-06 | 1977-06-06 | Psychoactive 3-(1-2-diarylethyl)-1,4,5,6-tetrahydro-1,2,4-triazines and their method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780115L IE780115L (en) | 1978-07-21 |
| IE46246B1 true IE46246B1 (en) | 1983-04-06 |
Family
ID=27116938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE115/78A IE46246B1 (en) | 1977-01-21 | 1978-01-18 | 3-substituted 1,2,4-triazines and their preparation |
Country Status (13)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428635A (en) * | 1966-12-05 | 1969-02-18 | Dow Chemical Co | Substituted 1,4,5,6 - tetrahydro - as - triazines and a method for their production |
| US3497509A (en) * | 1966-12-05 | 1970-02-24 | Dow Chemical Co | Imino ester method for producing 1,4,5,6-tetrahydro-as-triazine |
| US3471486A (en) * | 1967-10-23 | 1969-10-07 | Dow Chemical Co | 3-aralkyl-as-triazines |
-
1978
- 1978-01-05 DE DE19782800385 patent/DE2800385A1/de active Granted
- 1978-01-17 NL NL7800535A patent/NL7800535A/xx not_active Application Discontinuation
- 1978-01-17 DK DK023078A patent/DK152755C/da not_active IP Right Cessation
- 1978-01-18 IE IE115/78A patent/IE46246B1/en not_active IP Right Cessation
- 1978-01-19 IT IT19422/78A patent/IT1111157B/it active
- 1978-01-19 NO NO78780201A patent/NO159529C/no unknown
- 1978-01-19 JP JP378478A patent/JPS5395987A/ja active Granted
- 1978-01-20 CH CH65378A patent/CH639080A5/fr not_active IP Right Cessation
- 1978-01-20 FR FR7801672A patent/FR2378019A1/fr active Granted
- 1978-01-20 SE SE7800737A patent/SE447380B/sv not_active IP Right Cessation
- 1978-01-20 ES ES466205A patent/ES466205A1/es not_active Expired
- 1978-01-20 AT AT44378A patent/AT360032B/de not_active IP Right Cessation
- 1978-01-20 GB GB2389/78A patent/GB1576579A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO780201L (no) | 1978-07-24 |
| NL7800535A (nl) | 1978-07-25 |
| FR2378019A1 (fr) | 1978-08-18 |
| DE2800385A1 (de) | 1978-07-27 |
| IT7819422A0 (it) | 1978-01-19 |
| DE2800385C2 (enrdf_load_html_response) | 1989-01-26 |
| SE7800737L (sv) | 1978-07-22 |
| AT360032B (de) | 1980-12-10 |
| NO159529B (no) | 1988-10-03 |
| GB1576579A (en) | 1980-10-08 |
| DK23078A (da) | 1978-07-22 |
| FR2378019B1 (enrdf_load_html_response) | 1980-08-22 |
| IE780115L (en) | 1978-07-21 |
| JPS6241227B2 (enrdf_load_html_response) | 1987-09-02 |
| DK152755B (da) | 1988-05-09 |
| ES466205A1 (es) | 1979-06-01 |
| JPS5395987A (en) | 1978-08-22 |
| DK152755C (da) | 1988-10-03 |
| ATA44378A (de) | 1980-05-15 |
| IT1111157B (it) | 1986-01-13 |
| CH639080A5 (en) | 1983-10-31 |
| SE447380B (sv) | 1986-11-10 |
| NO159529C (no) | 1989-01-11 |
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