KR850001209A - 피리다지노 [4,3-c] 이소퀴놀린 유도체 제조방법 - Google Patents
피리다지노 [4,3-c] 이소퀴놀린 유도체 제조방법 Download PDFInfo
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- KR850001209A KR850001209A KR1019840004038A KR840004038A KR850001209A KR 850001209 A KR850001209 A KR 850001209A KR 1019840004038 A KR1019840004038 A KR 1019840004038A KR 840004038 A KR840004038 A KR 840004038A KR 850001209 A KR850001209 A KR 850001209A
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- phenyl
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- 238000000034 method Methods 0.000 title claims 2
- AFCCQNLWUCZFJN-UHFFFAOYSA-N pyridazino[4,3-c]isoquinoline Chemical class C1=NN=C2C3=CC=CC=C3C=NC2=C1 AFCCQNLWUCZFJN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 12
- -1 hydroxy, phenyl Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000012320 chlorinating reagent Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- PVKJTSKFPRIRKP-UHFFFAOYSA-N 6-chloropyridazino[4,3-c]isoquinoline Chemical group C1=CC=C2C(Cl)=NC3=CC=NN=C3C2=C1 PVKJTSKFPRIRKP-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 125000005042 acyloxymethyl group Chemical group 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 239000007810 chemical reaction solvent Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 150000002012 dioxanes Chemical class 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- IRTKFUTVVLMDNV-UHFFFAOYSA-N isochromeno[4,3-c]pyridazin-6-one Chemical compound C12=CC=CC=C2C(=O)OC2=C1N=NC=C2 IRTKFUTVVLMDNV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Anesthesiology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
내용없음
Claims (10)
- 다음 일반식(I)의 피리다지노 [4,3-c] 이소퀴놀린 및 약리학적으로 허용되는 이들의 산부가염.식중, R는 메틸, 페닐 또는 치환페닐 [여기서, 페닐고리는(C1-C4) 알킬, (C1-C4) 알콕시, 할로겐, 히드록시, 페닐, 아미노 및 트리플루오로메틸로 된 군중에서 선택된 1-3개의 치환체로 치환됨]이고, R1은 수소, 염소 일반식 -NR4R5의 기[여기서, R4및 R5는 각각 독립적으로 수소, (C1-C4) 알킬, (C2-C4) 알케닐, (C2-C5) 알카노일옥시메틸, (C1-C4) 알콕시카르보닐, 또는 히드록시, (C1-C4) 알콕시, 할로겐, 카르복시, 시아노 및 아미노카르보닐로된 군중에서 선택된 또는 2개의 기로 독립적으로 치환된(C1-C4) 알킬, 페닐-(C1-C4) 알킬 또는 치환된 페닐-(C1-C4) 알킬 {여기서, 알킬부위는 히드록시, (C1-C4) 알콕시, 할로겐, 카르복시, (C1-C4) 알콕시카르보닐 및 (C2-C4) 알카노일옥시메틸로된 군중에서 선택된 1 또는 2개의 기로 치환되며, 페닐부위는 상기한 바와 같이 치환됨} 이거나, 또는 R4및 R5는 인접한 질소원자와 함께 포화된 4,5,6 또는 7-원헤테로사이클릭고리 (이 고리는 질소, 산소 및 항으로 된 군중에서 선택된 1개의 이종원자를 더 함유하며, 경우에 따라서는 (C1-C4) 알킬, 페닐, 히드록시 및 카르보 (C1-C4) 알콕시로된 군중에서 선택된 1 또는 2개의 치환체로 독립적으로 치환됨]이거나, 또는 R1은 일반식-OR6의 알콕시 또는 시클로알콕시기(여기서, R6은 히드록시,아미노-, 모노-또는 디-(C1-C4) 알킬아미노, (C1-C4) 알콕시, 할로겐, 옥소, 카르복시, 아미노카르보닐, 모노-또는 디-(C1-C4) 알킬아미노 카르보닐 및 (C1-C4) 알콕시카르보닐로된 군중에서 독립적으로 선택된 1 또는 2개의 기로/치환된 (C1-C6) 알킬이거나, 또는 R6는 히드록시 및 (C1-C4) 알콕시로된 군중에서 선택된 1 이딘의 치환체로 임의로 치환된 (C5-C8) 시클로알킬기임)이고, R2및 R3는 각각 독립적으로 수소, 할로겐(C1-C4) 알킬 또는 (C1-C4) 알콕시기이다.
- 제1항에 있어서, R가 메틸, 페닐 또는 치환페닐이고, R1은 일반식 -NR4R5(여기서, R4및 R5는 독립적으로 수소, (C1-C4) 알킬와 (C1-C4) 알콕시 및 히드록시로된 군중에서 선택된 1개의 기로 치환된 (C1-C4) 알킬이거나, 또는 R4및 R5는 인접한 질소원자와 함께 아제티디닐, 피롤리디닐, 피페리디닐, 피라졸리디닐, 피라지니딜, 피리미디닐, 피리다지니딜, 모르폴리닐, 이미다졸리디닐 및 피페라지닐로된 군 중에서 선택된 포화 헤테로사이클기임)기이고, R2및 R3는 독립적으로 수소 또는 할로겐 원자인 화합물 및 약리학적으로 허용되는 이들의 산부가염.
- 제1항에 있어서, 화합물이 3-페닐-6-(1-피롤리디닐)피리다지노-[4,3-c] 이소퀴놀린 화합물.
- 일반식(II)의 6H-[2] 벤조피라노-[4,3-c] 피리다진-6-온을 과몰량의 암모니아 또는 동일한 반응조건하에서 암모니아를 용이하게 생성할 수 있는 암모늄염과 반응시켜 일반식(III)의 피리다지노[4,3-c] 이소퀴놀린-6(5H)온을 얻고, 이어서 이 화합물을 일반식 I로 표시되는 화합물로 전환시킴을 특징으로 하는 피리다지노[4,3-c] 이소퀴놀린의 제조방법.식중, R,R2및 R3는 상기한 바와같고, R1은 염소화제의 반응에 의한 염소원자이다 [R1이 염소원자인 일반식(I)의 화합물은 R1이 상기한 바와 같지만 이 화합물을 일반식 HNR4R5의 아민, 알카리금속 알콕시드 또는 일반식 MeOR6의 시클로알콕시드(여기서, R4,R5및 R6는 상기한 바와 같고, Me는 알칼리금속임)와 반응시켜서 얻은 염소 이외의 것인 일반식(I)의 화합물로 전환시킬 수 있다].
- 제4항에서, 염소화제로서 과몰량의 PCl5또는 POCl5를 사용하는 것을 특징으로 하는 방법.
- 제4항에 있어서, 6-클로로-피리다지노[4,3-c] 이소퀴놀린을 일반식 R6OH(식중, R6는 알콕시드를 사용하는 경우와 동일함)의 저급알카놀, 글리코올에테르, 디옥산 및 테트라하이드로푸란으로된 군중에서 선택된 불활성 유기용에 존재하에서 과몰량의 일반식 HNR4R5(식중, R4및 R5는 상기한 바와같음)의 아민(반응용매로서 또한 작용함), 또는 1몰량 이상의 알칼리금속 알콕시드 또는 일반식 MeOR6(식중, Me 및 R6는 상기한 바와 같음)의 시클로알콕시드와 반응시킴을 특징으로 하는 방법.
- 일반식(III)의 3-치환피리다지노 [4,3-c] 피리딘.식중, R1,R2및 R3는 제1항에서 정의한 바와 같음.
- 진정제로 사용되는 제1항의 화합물.
- 유효성분으로서 제1항의 화합물과 약물학적으로 허용가능한 부형제를 혼합시킨 약학물적 조성물.
- 유효성분으로서 제1항의 화합물 25-250㎎과, 약물학적으로 허용가능한 담체를 혼합시킨 약물학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22013A/83 | 1983-07-12 | ||
| IT22013/83A IT1194309B (it) | 1983-07-12 | 1983-07-12 | Derivati 3-fenil-piridazino (4,3-c) isochinolinici |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850001209A true KR850001209A (ko) | 1985-03-16 |
| KR910005849B1 KR910005849B1 (ko) | 1991-08-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004038A KR910005849B1 (ko) | 1983-07-12 | 1984-07-11 | 피리다지노[4,3-c]이소퀴놀린 유도체 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4716159A (ko) |
| EP (1) | EP0134461B1 (ko) |
| JP (1) | JPS6048989A (ko) |
| KR (1) | KR910005849B1 (ko) |
| AT (1) | ATE30157T1 (ko) |
| AU (1) | AU570057B2 (ko) |
| CA (1) | CA1229602A (ko) |
| DE (1) | DE3466690D1 (ko) |
| DK (1) | DK323484A (ko) |
| ES (1) | ES8600289A1 (ko) |
| FI (1) | FI77861C (ko) |
| GR (1) | GR82126B (ko) |
| HU (1) | HU193687B (ko) |
| IL (1) | IL72308A (ko) |
| IT (1) | IT1194309B (ko) |
| NO (1) | NO160613C (ko) |
| NZ (1) | NZ208864A (ko) |
| PH (1) | PH22631A (ko) |
| PT (1) | PT78891B (ko) |
| ZA (1) | ZA844970B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0633277B2 (ja) * | 1986-01-10 | 1994-05-02 | 吉富製薬株式会社 | ベンゾチオピラノ〔４，３−ｃ〕ピリダジン化合物 |
| DE3814552A1 (de) * | 1988-04-29 | 1989-11-09 | Hoechst Ag | 9-oxo-1,9a-10-triaza-9-hydro-anthracen- verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4062958A (en) * | 1976-09-22 | 1977-12-13 | American Cyanamid Company | Method of treating anxiety and compositions therefor |
-
1983
- 1983-07-12 IT IT22013/83A patent/IT1194309B/it active
-
1984
- 1984-06-26 GR GR75128A patent/GR82126B/el unknown
- 1984-06-27 FI FI842586A patent/FI77861C/fi not_active IP Right Cessation
- 1984-06-29 DK DK323484A patent/DK323484A/da not_active Application Discontinuation
- 1984-06-29 ZA ZA844970A patent/ZA844970B/xx unknown
- 1984-06-29 EP EP84107554A patent/EP0134461B1/en not_active Expired
- 1984-06-29 DE DE8484107554T patent/DE3466690D1/de not_active Expired
- 1984-06-29 AT AT84107554T patent/ATE30157T1/de not_active IP Right Cessation
- 1984-07-03 AU AU30221/84A patent/AU570057B2/en not_active Ceased
- 1984-07-05 IL IL72308A patent/IL72308A/xx unknown
- 1984-07-10 JP JP59141572A patent/JPS6048989A/ja active Granted
- 1984-07-11 ES ES534200A patent/ES8600289A1/es not_active Expired
- 1984-07-11 PH PH30962A patent/PH22631A/en unknown
- 1984-07-11 NO NO842825A patent/NO160613C/no unknown
- 1984-07-11 PT PT78891A patent/PT78891B/pt not_active IP Right Cessation
- 1984-07-11 KR KR1019840004038A patent/KR910005849B1/ko not_active IP Right Cessation
- 1984-07-11 HU HU842715A patent/HU193687B/hu unknown
- 1984-07-11 CA CA000458578A patent/CA1229602A/en not_active Expired
- 1984-07-11 NZ NZ208864A patent/NZ208864A/xx unknown
-
1986
- 1986-07-30 US US06/891,815 patent/US4716159A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HU193687B (en) | 1987-11-30 |
| HUT34975A (en) | 1985-05-28 |
| JPH0559915B2 (ko) | 1993-09-01 |
| AU570057B2 (en) | 1988-03-03 |
| NO842825L (no) | 1985-01-14 |
| PT78891A (en) | 1984-08-01 |
| DE3466690D1 (de) | 1987-11-12 |
| FI842586A0 (fi) | 1984-06-27 |
| PH22631A (en) | 1988-10-28 |
| GR82126B (ko) | 1984-12-13 |
| CA1229602A (en) | 1987-11-24 |
| NZ208864A (en) | 1988-06-30 |
| IT1194309B (it) | 1988-09-14 |
| IL72308A (en) | 1987-11-30 |
| EP0134461B1 (en) | 1987-10-07 |
| FI77861C (fi) | 1989-05-10 |
| FI77861B (fi) | 1989-01-31 |
| ATE30157T1 (de) | 1987-10-15 |
| ZA844970B (en) | 1985-03-27 |
| IL72308A0 (en) | 1984-11-30 |
| AU3022184A (en) | 1985-01-17 |
| KR910005849B1 (ko) | 1991-08-05 |
| NO160613C (no) | 1989-05-10 |
| ES534200A0 (es) | 1985-06-01 |
| EP0134461A1 (en) | 1985-03-20 |
| IT8322013A0 (it) | 1983-07-12 |
| DK323484A (da) | 1985-01-13 |
| NO160613B (no) | 1989-01-30 |
| PT78891B (en) | 1986-10-23 |
| FI842586A (fi) | 1985-01-13 |
| US4716159A (en) | 1987-12-29 |
| DK323484D0 (da) | 1984-06-29 |
| JPS6048989A (ja) | 1985-03-16 |
| ES8600289A1 (es) | 1985-06-01 |
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| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |