HU194188B - Process for preparing hh-1,2,4-triazole derivatives and pharmaceuticals comprising the same - Google Patents
Process for preparing hh-1,2,4-triazole derivatives and pharmaceuticals comprising the same Download PDFInfo
- Publication number
- HU194188B HU194188B HU853577A HU357785A HU194188B HU 194188 B HU194188 B HU 194188B HU 853577 A HU853577 A HU 853577A HU 357785 A HU357785 A HU 357785A HU 194188 B HU194188 B HU 194188B
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- HU
- Hungary
- Prior art keywords
- formula
- compound
- group
- alkyl
- racemic
- Prior art date
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- 239000003814 drug Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 238000002360 preparation method Methods 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 7
- -1 nitro, amino Chemical group 0.000 claims description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 241001136792 Alle Species 0.000 claims 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
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- 238000003756 stirring Methods 0.000 description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- ROFVGYAMRSGUSQ-UHFFFAOYSA-N 1-(2-bromoethyl)piperazine;hydrobromide Chemical compound Br.BrCCN1CCNCC1 ROFVGYAMRSGUSQ-UHFFFAOYSA-N 0.000 description 5
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
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- 239000012074 organic phase Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- QCICYPQPGJJZGW-UHFFFAOYSA-N 2-hydroxypropanehydrazide Chemical compound CC(O)C(=O)NN QCICYPQPGJJZGW-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- COAWCFYTMKBWPF-UHFFFAOYSA-N 3-ethyl-4-(4-methoxyphenyl)-5-(3-nitrophenyl)-1,2,4-triazole Chemical compound C=1C=C(OC)C=CC=1N1C(CC)=NN=C1C1=CC=CC([N+]([O-])=O)=C1 COAWCFYTMKBWPF-UHFFFAOYSA-N 0.000 description 2
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- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- IJLDXKIMXVBWEJ-UHFFFAOYSA-N n-(4-methoxyphenyl)-3-nitrobenzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 IJLDXKIMXVBWEJ-UHFFFAOYSA-N 0.000 description 1
- NARGSXJDVYTGBN-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-nitrobenzamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 NARGSXJDVYTGBN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Packaging Of Special Articles (AREA)
- Signal Processing For Digital Recording And Reproducing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8414598A FR2570699B1 (fr) | 1984-09-24 | 1984-09-24 | Nouveau procede de preparation de derives du 4h-1,2,4-triazole, nouveaux triazoles ainsi obtenus, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT40090A HUT40090A (en) | 1986-11-28 |
| HU194188B true HU194188B (en) | 1988-01-28 |
Family
ID=9307987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU853577A HU194188B (en) | 1984-09-24 | 1985-09-23 | Process for preparing hh-1,2,4-triazole derivatives and pharmaceuticals comprising the same |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0176444B1 (OSRAM) |
| JP (1) | JPS6185370A (OSRAM) |
| AT (1) | ATE40886T1 (OSRAM) |
| AU (1) | AU585895B2 (OSRAM) |
| CA (1) | CA1256113A (OSRAM) |
| DE (1) | DE3568331D1 (OSRAM) |
| DK (1) | DK429085A (OSRAM) |
| ES (1) | ES8704907A1 (OSRAM) |
| FI (1) | FI86178C (OSRAM) |
| FR (1) | FR2570699B1 (OSRAM) |
| GR (1) | GR852310B (OSRAM) |
| HU (1) | HU194188B (OSRAM) |
| IE (1) | IE58497B1 (OSRAM) |
| OA (1) | OA08105A (OSRAM) |
| PT (1) | PT81180B (OSRAM) |
| ZA (1) | ZA857294B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8429307D0 (en) * | 1984-11-20 | 1984-12-27 | Shell Int Research | Heterocyclic herbicides |
| EP0496900B1 (en) * | 1990-08-22 | 1996-05-29 | Central Glass Company, Limited | N-acyl-n-phenyltetrahydrophthalamic acid derivative, production thereof, and herbicide containing the same as active ingredient |
| US5523325A (en) * | 1993-09-09 | 1996-06-04 | Jacobson; Richard M. | Amidrazones and their use as pesticides |
| KR100470076B1 (ko) | 2002-11-27 | 2005-02-05 | 씨제이 주식회사 | 1,2,4-트리아졸 유도체, 그 제조방법 및 약제학적 조성물 |
| JP2011500780A (ja) * | 2007-10-24 | 2011-01-06 | ジェネリクス・（ユーケー）・リミテッド | 新規結晶形 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2884424A (en) * | 1957-11-18 | 1959-04-28 | American Cyanamid Co | Production of triazoles and amidrazones of the anthraquinone series |
| FR2244462A1 (en) * | 1973-09-25 | 1975-04-18 | Delalande Sa | Antihypertensive, 5-hydroxy methyl 1,2,4-triazoles - prepd. from aniline and a hydroxy methyl 1,3,4-oxadiazole |
| FR2269938A2 (en) * | 1974-05-08 | 1975-12-05 | Delalande Sa | 5-Hydroxymethyl-3,4-diphenyl-1,2,4-triazoles - with anticholinergic, bronchodilator, antidepressant, analgesic, vasodilator activity, etc. |
| GB1510647A (en) * | 1975-10-10 | 1978-05-10 | Commw Scient Ind Res Org | Triazoles |
| FR2512022A2 (fr) * | 1980-08-22 | 1983-03-04 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| FR2488891A1 (fr) * | 1980-08-22 | 1982-02-26 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicament |
| FR2539127B1 (fr) * | 1983-01-10 | 1985-08-23 | Roussel Uclaf | Nouveaux derives du 4h-1,2,4-triazole, leur procede de preparation et leur application comme medicaments |
-
1984
- 1984-09-24 FR FR8414598A patent/FR2570699B1/fr not_active Expired
-
1985
- 1985-09-23 ES ES547209A patent/ES8704907A1/es not_active Expired
- 1985-09-23 FI FI853643A patent/FI86178C/fi not_active IP Right Cessation
- 1985-09-23 EP EP85401844A patent/EP0176444B1/fr not_active Expired
- 1985-09-23 CA CA000491319A patent/CA1256113A/fr not_active Expired
- 1985-09-23 ZA ZA857294A patent/ZA857294B/xx unknown
- 1985-09-23 DE DE8585401844T patent/DE3568331D1/de not_active Expired
- 1985-09-23 AT AT85401844T patent/ATE40886T1/de active
- 1985-09-23 GR GR852310A patent/GR852310B/el unknown
- 1985-09-23 IE IE233885A patent/IE58497B1/en not_active IP Right Cessation
- 1985-09-23 DK DK429085A patent/DK429085A/da not_active Application Discontinuation
- 1985-09-23 HU HU853577A patent/HU194188B/hu not_active IP Right Cessation
- 1985-09-24 JP JP60209044A patent/JPS6185370A/ja active Pending
- 1985-09-24 AU AU47840/85A patent/AU585895B2/en not_active Ceased
- 1985-09-24 OA OA58685A patent/OA08105A/xx unknown
- 1985-09-24 PT PT81180A patent/PT81180B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE58497B1 (en) | 1993-10-06 |
| GR852310B (OSRAM) | 1986-01-24 |
| PT81180A (fr) | 1985-10-01 |
| FR2570699B1 (fr) | 1987-08-28 |
| OA08105A (fr) | 1987-03-31 |
| DE3568331D1 (en) | 1989-03-30 |
| JPS6185370A (ja) | 1986-04-30 |
| ES8704907A1 (es) | 1987-04-16 |
| PT81180B (pt) | 1988-01-22 |
| EP0176444A1 (fr) | 1986-04-02 |
| AU4784085A (en) | 1986-04-10 |
| FI853643L (fi) | 1986-03-25 |
| HUT40090A (en) | 1986-11-28 |
| FI86178B (fi) | 1992-04-15 |
| DK429085A (da) | 1986-03-25 |
| ES547209A0 (es) | 1987-04-16 |
| DK429085D0 (da) | 1985-09-23 |
| CA1256113A (fr) | 1989-06-20 |
| ZA857294B (en) | 1986-11-26 |
| AU585895B2 (en) | 1989-06-29 |
| ATE40886T1 (de) | 1989-03-15 |
| FR2570699A1 (fr) | 1986-03-28 |
| EP0176444B1 (fr) | 1989-02-22 |
| FI853643A0 (fi) | 1985-09-23 |
| FI86178C (fi) | 1992-07-27 |
| IE852338L (en) | 1986-03-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |