CS200160B2 - Method of producing novel derivatives of arylamino imidazoline - Google Patents
Method of producing novel derivatives of arylamino imidazoline Download PDFInfo
- Publication number
- CS200160B2 CS200160B2 CS788521A CS852178A CS200160B2 CS 200160 B2 CS200160 B2 CS 200160B2 CS 788521 A CS788521 A CS 788521A CS 852178 A CS852178 A CS 852178A CS 200160 B2 CS200160 B2 CS 200160B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- apos
- und
- phosphorus oxychloride
- imidazoline
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- -1 derivatives of arylamino imidazoline Chemical compound 0.000 title description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000005457 ice water Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000001077 hypotensive effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 229960002896 clonidine Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WEXMRNBZLGRMRL-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C1=C(Cl)C=CC=C1Cl WEXMRNBZLGRMRL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- YHEMKMZUJKPOCO-UHFFFAOYSA-N [2-(2,6-dichloroanilino)-4,5-dihydroimidazol-1-yl]-phenylmethanone Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1C(=O)C1=CC=CC=C1 YHEMKMZUJKPOCO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HRWOJQYMTPJEBS-UHFFFAOYSA-N cyclohept-4-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CCC=CCC1 HRWOJQYMTPJEBS-UHFFFAOYSA-N 0.000 description 1
- CXWMHIRIXVNVQN-UHFFFAOYSA-N cyclohex-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CCC=CC1 CXWMHIRIXVNVQN-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- PNNPWJAWAATBJZ-UHFFFAOYSA-N cyclopent-3-ene-1-carbonyl chloride Chemical compound ClC(=O)C1CC=CC1 PNNPWJAWAATBJZ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical compound O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- SACAEVOKRBNXPN-UHFFFAOYSA-N n-phenyl-4,5-dihydroimidazol-1-amine Chemical class C1=NCCN1NC1=CC=CC=C1 SACAEVOKRBNXPN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782811847 DE2811847A1 (de) | 1978-03-17 | 1978-03-17 | Neue arylaminoimidazolinderivate, deren herstellung und verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200160B2 true CS200160B2 (en) | 1980-08-29 |
Family
ID=6034806
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788521A CS200160B2 (en) | 1978-03-17 | 1978-12-18 | Method of producing novel derivatives of arylamino imidazoline |
| CS788522A CS203026B2 (en) | 1978-03-17 | 1978-12-18 | Process for preparing new derivatives of arylaminoimidazoline |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788522A CS203026B2 (en) | 1978-03-17 | 1978-12-18 | Process for preparing new derivatives of arylaminoimidazoline |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4142051A (da) |
| EP (1) | EP0004529B1 (da) |
| JP (1) | JPS54128570A (da) |
| AU (1) | AU521523B2 (da) |
| CA (2) | CA1100513A (da) |
| CS (2) | CS200160B2 (da) |
| DD (2) | DD141158A1 (da) |
| DE (2) | DE2811847A1 (da) |
| DK (1) | DK569078A (da) |
| ES (2) | ES476354A1 (da) |
| FI (1) | FI784017A7 (da) |
| GR (2) | GR64428B (da) |
| HU (1) | HU179219B (da) |
| IL (1) | IL56075A (da) |
| NO (1) | NO784423L (da) |
| NZ (1) | NZ189279A (da) |
| PT (2) | PT68989A (da) |
| ZA (1) | ZA787312B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MTP837B (en) * | 1977-11-07 | 1979-10-22 | Hoffman La Roche And Co Aktien | Derivatives 2 finino-imidazolidire |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPS5922715U (ja) * | 1982-08-04 | 1984-02-13 | 藤徳紙器株式会社 | 紙製容器 |
| JPS5922714U (ja) * | 1982-08-04 | 1984-02-13 | 藤徳紙器株式会社 | 紙製容器 |
| JPS5935321U (ja) * | 1982-08-30 | 1984-03-05 | 株式会社岡田 | 紙製容器の側板構造 |
| DE19514579A1 (de) * | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741947A (en) | 1969-11-19 | 1970-05-04 | N-acyl-2-arylamino-imidazoline | |
| DE2041732A1 (de) * | 1970-08-22 | 1972-02-24 | Bayer Ag | Acylierte Arylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide |
| BE787683A (fr) * | 1971-08-20 | 1973-02-19 | Boehringer Sohn Ingelheim | 2-phenylimino-imidazolidines, leurs sels d'addition avec des acides et procedes pour les fabriquer |
| DE2316377C3 (de) * | 1973-04-02 | 1978-11-02 | Lentia Gmbh, Chem. U. Pharm. Erzeugnisse - Industriebedarf, 8000 Muenchen | Verfahren zur Herstellung von 2-Phenyl-amino-2-imidazolin-Derivaten und von deren Salzen |
| AT330769B (de) | 1974-04-05 | 1976-07-26 | Chemie Linz Ag | Verfahren zur herstellung von 2-arylamino- 2-imidazolin-derivaten und ihren salzen |
| AT333749B (de) | 1974-07-03 | 1976-12-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen 2-arylamino-2-imidazolinderivaten |
| DE2542702C2 (de) | 1975-09-25 | 1983-11-10 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur Herstellung von 1-Benzoyl-2-(2,6-dichlorphenylamino)-2-imidazolin |
| AT339897B (de) * | 1975-09-25 | 1977-11-10 | Chemie Linz Ag | Verfahren zur herstellung des neuen 1-benzoyl-2- (2',6'-dichlorphenylamino) -2-imidazolins und von dessen salzen |
-
1978
- 1978-03-17 DE DE19782811847 patent/DE2811847A1/de not_active Withdrawn
- 1978-04-20 US US05/898,543 patent/US4142051A/en not_active Expired - Lifetime
- 1978-11-29 IL IL56075A patent/IL56075A/xx unknown
- 1978-12-05 DE DE7878101569T patent/DE2860796D1/de not_active Expired
- 1978-12-05 EP EP78101569A patent/EP0004529B1/de not_active Expired
- 1978-12-06 CA CA317,502A patent/CA1100513A/en not_active Expired
- 1978-12-06 CA CA317,503A patent/CA1107285A/en not_active Expired
- 1978-12-16 GR GR57905A patent/GR64428B/el unknown
- 1978-12-16 GR GR57906A patent/GR64429B/el unknown
- 1978-12-18 CS CS788521A patent/CS200160B2/cs unknown
- 1978-12-18 CS CS788522A patent/CS203026B2/cs unknown
- 1978-12-19 DK DK569078A patent/DK569078A/da not_active Application Discontinuation
- 1978-12-21 NZ NZ189279A patent/NZ189279A/xx unknown
- 1978-12-26 JP JP15940078A patent/JPS54128570A/ja active Granted
- 1978-12-27 ES ES476354A patent/ES476354A1/es not_active Expired
- 1978-12-27 DD DD78210201A patent/DD141158A1/de unknown
- 1978-12-27 ZA ZA00787312A patent/ZA787312B/xx unknown
- 1978-12-27 PT PT68989A patent/PT68989A/pt unknown
- 1978-12-27 ES ES476355A patent/ES476355A1/es not_active Expired
- 1978-12-27 PT PT68988A patent/PT68988A/pt unknown
- 1978-12-27 DD DD78210199A patent/DD141157A1/de unknown
- 1978-12-28 FI FI784017A patent/FI784017A7/fi unknown
- 1978-12-28 AU AU42945/78A patent/AU521523B2/en not_active Expired
- 1978-12-29 NO NO784423A patent/NO784423L/no unknown
- 1978-12-29 HU HU78LI336A patent/HU179219B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA787312B (en) | 1979-12-27 |
| DD141158A1 (de) | 1980-04-16 |
| AU4294578A (en) | 1979-09-20 |
| NO784423L (no) | 1979-09-18 |
| GR64429B (en) | 1980-03-21 |
| IL56075A (en) | 1982-01-31 |
| DK569078A (da) | 1979-09-18 |
| GR64428B (en) | 1980-03-21 |
| CS203026B2 (en) | 1981-02-27 |
| FI784017A7 (fi) | 1979-09-18 |
| DE2860796D1 (en) | 1981-09-24 |
| CA1100513A (en) | 1981-05-05 |
| DE2811847A1 (de) | 1979-09-20 |
| DD141157A1 (de) | 1980-04-16 |
| ES476355A1 (es) | 1979-07-01 |
| EP0004529A2 (de) | 1979-10-17 |
| ES476354A1 (es) | 1979-05-16 |
| CA1107285A (en) | 1981-08-18 |
| US4142051A (en) | 1979-02-27 |
| JPS5755716B2 (da) | 1982-11-25 |
| JPS54128570A (en) | 1979-10-05 |
| IL56075A0 (en) | 1979-01-31 |
| HU179219B (en) | 1982-09-28 |
| PT68988A (de) | 1979-01-01 |
| PT68989A (de) | 1979-01-01 |
| EP0004529A3 (en) | 1979-11-14 |
| EP0004529B1 (de) | 1981-06-17 |
| AU521523B2 (en) | 1982-04-08 |
| NZ189279A (en) | 1980-08-26 |
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