KR850004755A - 피리딘-2-에테르 또는 피리딘-2-티오에테르의 제조방법 - Google Patents
피리딘-2-에테르 또는 피리딘-2-티오에테르의 제조방법 Download PDFInfo
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- KR850004755A KR850004755A KR1019840008498A KR840008498A KR850004755A KR 850004755 A KR850004755 A KR 850004755A KR 1019840008498 A KR1019840008498 A KR 1019840008498A KR 840008498 A KR840008498 A KR 840008498A KR 850004755 A KR850004755 A KR 850004755A
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- 238000004519 manufacturing process Methods 0.000 title claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- -1 methylenedioxy group Chemical group 0.000 claims 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur 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
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/54—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 일반식(Ⅱ)의 화합물 또는 그의 피리딘 -N-옥사이드를 일반식(Ⅲ)의 화합물과 반응시키고, 그룹S (S는 통상적인 아미노 보호그룹이다)가 존재하는 경우에는 이를 분리 제거시키고/거나 일반식(Ⅰ)화합물중의 라디칼 R1,R2및 R3를 가능한 다른 치환체로 전환시키고/거나 일반식(Ⅰ)의 화합물을 상응하는 설폰, 설포사이드, 아민-옥사이드 또는 피리딘-N-옥사이드로 전환시켜 일반식(Ⅰ)의 화합물, 그의 피리딘-N-옥사이드 및/또는 그의 아민-옥사이드를 제조하는 방법.상기식에서, 라디칼 R1및 R2는 동일하거나 다르며, 수소, 할로겐원자, 트리플루오로메틸 그룹, 시아노그룹, 니트로그룹, 아미노그룹, 모노-C1-C6-알킬아미노그룹, 디-C1-C6-알킬아미노 그룹; 페닐 라디칼, 모노-또는 디-할로페닐 라디칼 또는 페닐-C1-C4-알킬 라디칼로 치환된 아미노그룹; C1-C6-알카노일아미노그룹, C1-C6-알콕시카보닐아미노그룹; 페닐 라디칼로 임의 치환된 C1-C6-알킬그룹;페닐그룹, 히드록시 그룹, C1-C6-알콕시그룹, 페녹시그룹, 카복시그룹, 카브-C1-C6-알콕시그룹, 또는 1 또는 2개의 C1-C6-알킬 그룹으로 임의 치환된 카바모일 그룹이고, 라디칼 R3는 수소 C1-C6-알킬그룹, C3-C6-알케닐그룹, C3-C6-알키닐그룹, C3-C7-시클로알킬그룹, C5-C7-시클로알케닐그룹, 페닐-C1-C4-알킬그룹, 카브-C1-C6-알콕시그룹; C3-C6-클로알킬라디칼로 치환된 C2-C6-알카노일그룹, 또는 동일한 탄소원자상에 2개의 C1-C6-알콕시그룹 또는 C2-C4-알킬렌 디옥시 그룹을 함유하는 C1-C4-알킬그룹이고, 또는 상기식에서, R3는 C3-C7-시클로알킬그룹, 히드록시그룹, C1-C6-알콕시그룹, 할로겐원자, 설포그룹(-SO3H), 아미노그룹, C1-C6-알킬아미노그룹, 디-C1-C6-알킬아미노그룹, C1-C6-알킬카보닐그룹, C3-C7-시클로알킬카보닐그룹, 카브-C1-C6-알콕시그룹 또는 벤조일 그룹으로 일-또는 이-치환된 C1-C6-알킬 그룹이고, X는 산소, 황, SO 또는 SO2이고, Alk는 탄소수 0 내지 4의 알킬렌이고, n과 m은 동일하거나 다르며 1 내지 3일 수 있으며, Alk가 적어도 1개의 탄소 원자를 갖는 알킬렌일 경우 n은 0일 수 있고, 이때 m은 2내지 6이며 하기 그룹은 퀴누클리딜 또는 트로파닐라디칼일 수 있고,일반식(Ⅲ)에서, R3는 또한 그룹 S(S는 통상적인 아미노 보호그룹이다)일 수 있고, Y는 일반식(Ⅱ)의 Z가 히드록시 그룹 또는 머캅토 그룹일 경우에는, 할로겐 원자, C1-C6-알킬설포닐옥시 그룹 또는 아릴설포닐옥시 그룹이고; 일반식(Ⅱ)의 Z가 할로겐원자인 경우에는 히드록시 그룹 또는 머캅토그룹이다.
- 제1항에 있어서, 생성된 화합물을 그의 염으로 전환시키는 방법.
- 제1항에 있어서, R1은 수소, 아미노그룹 또는 C2-C6-알카노일아미노그룹이고, R2는 염소, 브롬, 불소, C1-C4-알킬 또는 C1-C4-알콕시그룹이고, X는 황이고, Alk는 존재하지 않으며, R2는 수소, C3-C6-알케닐, 또는 할로겐원자, 메틸렌디옥시 그룹 또는 1 또는 2개의 히드록시 그룹이고 치환될 수 있는 C1-C6-알킬이고, 다음 일반식의 염기성 포화환이N-원자에 라디칼 R3로 임의 치환될 수 있는 피롤리딜 잔기, 피레리딜 잔기 또는 호모피페리딜 잔기인 화합물 또는 그의 염을 제조하는 방법.
- 제1항에 있어서, R1은 수소이고, R2는 염소, 브롬 또는 불소이고, X는 황이고, Alk는 존재하지 않으며, R3는 수소 또는 C1-C6-알킬그룹이고, 다음 일반식의 염기성 포화환이N-원자에 라디칼 R3로 임의 치환될 수 있는 피롤리딜 잔기, 피레리딜 잔기 또는 호모피페리딜 잔기인 화합물 또는 그의 염을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3347276 | 1983-12-28 | ||
DEP3347276.9 | 1983-12-28 | ||
DE93347276.9 | 1983-12-28 |
Publications (2)
Publication Number | Publication Date |
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KR850004755A true KR850004755A (ko) | 1985-07-27 |
KR870000354B1 KR870000354B1 (ko) | 1987-03-05 |
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Application Number | Title | Priority Date | Filing Date |
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KR1019840008498A KR870000354B1 (ko) | 1983-12-28 | 1984-12-28 | 피리딘-2-에테르 또는 피리딘-2-티오에테르의 제조방법 |
Country Status (20)
Country | Link |
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US (1) | US4643995A (ko) |
EP (1) | EP0149088B1 (ko) |
JP (1) | JPS60169476A (ko) |
KR (1) | KR870000354B1 (ko) |
CN (1) | CN85101353A (ko) |
AT (1) | ATE40131T1 (ko) |
AU (1) | AU566560B2 (ko) |
DD (1) | DD231354A5 (ko) |
DE (2) | DE3476205D1 (ko) |
DK (1) | DK613384A (ko) |
ES (1) | ES8607014A1 (ko) |
FI (1) | FI84062C (ko) |
GB (1) | GB2152048B (ko) |
GR (1) | GR82596B (ko) |
HU (1) | HU194209B (ko) |
IL (1) | IL73608A (ko) |
NO (1) | NO164237C (ko) |
PT (1) | PT79736B (ko) |
SU (1) | SU1417796A3 (ko) |
ZA (1) | ZA848275B (ko) |
Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
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ZA836994B (en) * | 1982-09-30 | 1984-05-30 | Robins Co Inc A H | Fused aromatic oxazepinones and sulfur analogs thereof |
DK623586A (da) * | 1985-12-27 | 1987-06-28 | Eisai Co Ltd | Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne |
US4853027A (en) * | 1986-09-08 | 1989-08-01 | E. I. Du Pont De Nemours And Company | Phytotoxic 2-alkyl-5-(heterocyclic)-pyrrole-3,4-dicarboxylates |
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-
1984
- 1984-10-23 ZA ZA848275A patent/ZA848275B/xx unknown
- 1984-11-23 IL IL73608A patent/IL73608A/xx unknown
- 1984-12-01 AT AT84114607T patent/ATE40131T1/de not_active IP Right Cessation
- 1984-12-01 DE DE8484114607T patent/DE3476205D1/de not_active Expired
- 1984-12-01 DE DE19843443968 patent/DE3443968A1/de not_active Withdrawn
- 1984-12-01 EP EP84114607A patent/EP0149088B1/de not_active Expired
- 1984-12-17 US US06/682,773 patent/US4643995A/en not_active Expired - Fee Related
- 1984-12-20 AU AU36996/84A patent/AU566560B2/en not_active Ceased
- 1984-12-20 DK DK613384A patent/DK613384A/da not_active Application Discontinuation
- 1984-12-20 GB GB08432162A patent/GB2152048B/en not_active Expired
- 1984-12-21 SU SU843826165A patent/SU1417796A3/ru active
- 1984-12-21 PT PT79736A patent/PT79736B/pt not_active IP Right Cessation
- 1984-12-25 JP JP59272172A patent/JPS60169476A/ja active Pending
- 1984-12-27 FI FI845126A patent/FI84062C/fi not_active IP Right Cessation
- 1984-12-27 GR GR82596A patent/GR82596B/el unknown
- 1984-12-27 DD DD84271863A patent/DD231354A5/de unknown
- 1984-12-27 ES ES539076A patent/ES8607014A1/es not_active Expired
- 1984-12-27 NO NO845250A patent/NO164237C/no unknown
- 1984-12-28 HU HU844869A patent/HU194209B/hu not_active IP Right Cessation
- 1984-12-28 KR KR1019840008498A patent/KR870000354B1/ko not_active IP Right Cessation
-
1985
- 1985-04-01 CN CN198585101353A patent/CN85101353A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
EP0149088B1 (de) | 1989-01-18 |
SU1417796A3 (ru) | 1988-08-15 |
HU194209B (en) | 1988-01-28 |
ES539076A0 (es) | 1986-05-16 |
HUT36115A (en) | 1985-08-28 |
CN85101353A (zh) | 1986-10-15 |
FI84062B (fi) | 1991-06-28 |
AU3699684A (en) | 1985-07-04 |
AU566560B2 (en) | 1987-10-22 |
NO845250L (no) | 1985-07-01 |
ES8607014A1 (es) | 1986-05-16 |
KR870000354B1 (ko) | 1987-03-05 |
FI84062C (fi) | 1991-10-10 |
JPS60169476A (ja) | 1985-09-02 |
FI845126A0 (fi) | 1984-12-27 |
ATE40131T1 (de) | 1989-02-15 |
NO164237C (no) | 1990-09-12 |
GR82596B (en) | 1985-04-29 |
GB2152048A (en) | 1985-07-31 |
IL73608A (en) | 1987-12-31 |
GB8432162D0 (en) | 1985-01-30 |
US4643995A (en) | 1987-02-17 |
ZA848275B (en) | 1985-08-28 |
FI845126L (fi) | 1985-06-29 |
EP0149088A1 (de) | 1985-07-24 |
NO164237B (no) | 1990-06-05 |
GB2152048B (en) | 1987-11-11 |
DD231354A5 (de) | 1985-12-24 |
PT79736A (de) | 1985-01-01 |
DE3476205D1 (en) | 1989-02-23 |
DK613384D0 (da) | 1984-12-20 |
DK613384A (da) | 1985-06-29 |
PT79736B (de) | 1986-12-30 |
DE3443968A1 (de) | 1985-10-31 |
IL73608A0 (en) | 1985-02-28 |
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