KR860002553A - 마크로폴리사이클 희토류 복합체의 제조방법 - Google Patents
마크로폴리사이클 희토류 복합체의 제조방법 Download PDFInfo
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- KR860002553A KR860002553A KR1019850007109A KR850007109A KR860002553A KR 860002553 A KR860002553 A KR 860002553A KR 1019850007109 A KR1019850007109 A KR 1019850007109A KR 850007109 A KR850007109 A KR 850007109A KR 860002553 A KR860002553 A KR 860002553A
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- bis
- phenanthroline
- radical
- macropolycycle
- bipyridine
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- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract 9
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000002131 composite material Substances 0.000 title claims 2
- -1 rare earth ions Chemical class 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 238000000034 method Methods 0.000 claims 7
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 6
- 229930195733 hydrocarbon Natural products 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 229910052693 Europium Inorganic materials 0.000 claims 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical group [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229910052771 Terbium Inorganic materials 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 150000002500 ions 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
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims 2
- MVFFFGBENCZRHC-UHFFFAOYSA-N 1,1'-biphenyl;2-pyridin-2-ylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=C1.N1=CC=CC=C1C1=CC=CC=N1 MVFFFGBENCZRHC-UHFFFAOYSA-N 0.000 claims 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- MTTPJFQIRJNLHN-UHFFFAOYSA-N 1-(bromomethyl)-3-[1-(bromomethyl)isoquinolin-3-yl]isoquinoline Chemical compound C1=CC=C2C(CBr)=NC(C=3N=C(C4=CC=CC=C4C=3)CBr)=CC2=C1 MTTPJFQIRJNLHN-UHFFFAOYSA-N 0.000 claims 1
- MVVRNAUFPUDQIB-UHFFFAOYSA-N 1-isoquinolin-1-ylisoquinoline Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CN=3)=NC=CC2=C1 MVVRNAUFPUDQIB-UHFFFAOYSA-N 0.000 claims 1
- 229910052692 Dysprosium Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052772 Samarium Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001217 Terbium Chemical class 0.000 claims 1
- UMVFZJRCHRLAGC-UHFFFAOYSA-N anthracene-1-carboxamide Chemical compound C1=CC=C2C=C3C(C(=O)N)=CC=CC3=CC2=C1 UMVFZJRCHRLAGC-UHFFFAOYSA-N 0.000 claims 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- VJTJVFFICHLTKX-UHFFFAOYSA-N dipyridin-2-yldiazene Chemical compound N1=CC=CC=C1N=NC1=CC=CC=N1 VJTJVFFICHLTKX-UHFFFAOYSA-N 0.000 claims 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/77—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing rare earth metals
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
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- 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
- C07D471/22—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 systems contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2458/00—Labels used in chemical analysis of biological material
- G01N2458/40—Rare earth chelates
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- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 희토류이온의 형광을 향상하는 방법에 있어서, 다음식의 마크로폴리사이클 화합물과 하나 이상의 회토류 이온을 착화하고 그 화합물의 공여단위를 여기시킴을 특징으로 하는 방법:상기식에서, Z는 3가 또는 4가 원자이고, R은 빈항이거나 또는 수소, 히드록실기, 아미노기 또는 탄화수소 라디칼을 나타내며, 2가 라디칼와는 하나 이상의 헤테로 원자를 임의로 함유하는 헤테로 마크로사이클에 의하여 임의로 개입되는 서로 독립적인 탄화수소체인이다. 또한 라디칼또는의 적어도 하나는 하나이상의 분자단위를 함유하거나 또는 기본적으로 한 분자단위로 되어 있음, 분자단위는 착화된 회토류 이온의 발광준위보다 더 큰 삼중항에너지를 보유함.
- 마크로폴리사이클 회토류 복합체의 제조방법에 있어서, 다음 식의 마크로폴리사이클 화합물과 하나 이상의 회토류 염을 반응시킴을 특징으로 하는 방법:상기식에서, Z는 3가 또는 4가 원자이고, R은 빈항이거나 또는 수소, 히드록실기, 아미노기 또는 탄화수소 라디칼을 나타내며, 2가 라디칼와는 하나 이상의 헤테로 원자를 임으로 함유하고 헤테로 마크로사이클에 의하여 임의로 개입되는 서로 독립적인 탄화수소체인이다. 또한 라디칼또는의 적어도 하나는 하나이상의 분자단위를 함유하거나 또는 기본적으로 한 분자단위로 되어 있음. 분자단위는 착화된 회토류 이온의 발광준위보다 더 큰 삼중항에너지를 보유함. 단서로서, 만일 회토류염이 유로퓸 도는 테르븀염이라면 Z는 질소 R은 H또는 NH2. ⓐ는 (CH2)2-O-C6H3R-O-(CH2)2-, ⓑ와 ⓒ는 동시에 같지는 않고 각각 라디칼 -(CH2)2-O-(CH2)2-와 라디칼 -(CH2)2-O-(CH2)2-O-(CH2)2-의 하나이고, R은 H 또는 NH2임.
- 제2항에 있어서, 탄화수소체인 에톡실화 또는 폴리에톡실화된 체인임을 특징으로 하는 방법.
- 제2 또는 3항에 있어서, 회토류 이온이 유로퓸, 테르븀, 사마륨가 디스프로슘으로 된 기로부터 선택됨을 특징으로 하는 방법.
- 제2항에 있어서, 에너지공여단위가 580nm 미만의 인광파장을 가짐을 특징으로 하는 방법.
- 제2항에 있어서, 분자단위가 펜안트롤린, 안트라센, 벤젠, 나프탈렌, 비페닐과 테르페닐, 아조벤젠, 아조피리딘, 피리딘, 비피리딘류, 그리고 비스퀴놀린류, 그리고 다음 식의 화합물로 되어있는 기로부터 선택됨을 특징으로 하는 방법:-C2H4-X1-C6H4-X2-C2H4- ; -C2H4-X1-CH2-C6H4-CH2-X2-C2H4-;상기식에서 X1과 X2는 동일하거나 다를 수있는데 산소, 질소 또는 황을 나타냄.상기식에서, X는 산소 또는 수소임.
- 제2항에 있어서 회토류 이온이 유로퓸 또는 테르븀이고 다음 마크로폴리사이클 화합물중 하나와 착화됨을 특징으로 하는 방법:(22)안트라센; (22)펜안트롤린; (22)펜안트롤린아미드; 22)안트라센아미드; (22)비이소퀴놀린; (22)비페닐-비피리딘; (22)비피리딘; (22);피리딘아미드, 트리스-비피리딘마크로폴리사이클, 펜안트롤린-비스-비피리딘트리스-펜안트롤린, 비스 이소퀴놀린 비스 비피리딘과 비스 비피리딘-디페닐비피리딘 마크로폴리사이클.
- 다음식을 갖는 마크로폴리사이클 화합물의 제조방법에 있어서:Z는 3가 또는 4가 원자이고, R은 빈항이거나 또는 수소, 히드록실기, 아미노기 또는 탄화수소 라디칼을 나타내며, 2가 라디칼와는 하나 이상의 헤테로 원자를 임으로 함유하는 헤테로 마크로사이클에 의하여 임의로 개입되는 서로 독립적인 탄화수소체인이고, 또한 라디칼또는 ⓒ의 적어도 하나는 하나이상의 분자단위를 함유하거나 또는 기본적으로 한 분자단위로 되어 있고, 분자단위는 착화된 회토류 이온의 발광준위보다 더 큰 삼중항에너지를 보유하고, 펜안트롤린, 안트라센 및 비피리딘류 및 이소퀴놀린류로 되어 있는 기로부터 선택되는데 Z가 질소, ⓐ는 다음 식중의 하나에 해당하고:ⓑ와 ⓒ는 동시에 -(CH2)2-O-(CH2)2-O-(CH2)2-가 아니라는 조건하에서, 라디칼 ⓐ,ⓑ 또는 ⓒ의 하나를 갖고 치환될 수 있는 말단기를 갖거나 또는 쉽게 제거될 수 있는 라디칼을 함유하는 각각의 화합물을 축합함을 특징으로 하는 방법.
- 제8항에 있어서, 식I의 Z가질소이고 ⓐ와 ⓑ가 폴리에톡실화된 체인일때, 1)두개의 폴리에톡실화된 체인으로 되어 있는 질소마크로사이클과 전술한 분자단위를 함유하고, 쪼갤 수 있는 말단기(예를들면 할로게노기)를 갖는 탄화수소체인을 반응시키고, 2)이렇게 얻은 염을 자유마크로폴리사이클 화합물로 임의 변환함을 특징으로 하는 방법.
- 제8또는 9항에 있어서, 질소마크로사이클이 다음 1)의 마크로사이클들 중에서 선택되고 탄화수소 체인이 다음 2)의 화합물들중에서 선택됨을 특징으로 하는 방법:1)C(22), 비스-비피리딘과 비스-펜안트롤린.2)-2,9-디브로모메틸-1,10-펜안트롤린,-2,9-디클로로카르보닐-1,10-펜안트롤린, -6,6′-비스-브로모메틸-2,2′-비피리딘, -2,9-비스-브로모메틸-1,10-펜안트롤린, 1,1′-비스-브로모메틸-3,3-비이소퀴놀린,-6,6′-비스-브로모메틸-4,4′-디페닐-2,2′-비피리딘, -9,10-비스-클로로카르보닐메틸-안트라센.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR8414799A FR2570703B1 (fr) | 1984-09-26 | 1984-09-26 | Complexes macropolycycliques de terres rares et application a titre de marqueurs fluorescents |
FR8414799 | 1984-09-26 |
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KR860002553A true KR860002553A (ko) | 1986-04-26 |
KR930008210B1 KR930008210B1 (ko) | 1993-08-26 |
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KR1019850007109A KR930008210B1 (ko) | 1984-09-26 | 1985-09-26 | 마크로폴리사이클 희토류 복합체의 제조방법 |
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---|---|
US (1) | US4927923A (ko) |
EP (1) | EP0180492B1 (ko) |
JP (3) | JPH0655741B2 (ko) |
KR (1) | KR930008210B1 (ko) |
AT (1) | ATE90084T1 (ko) |
CA (1) | CA1329593C (ko) |
DE (1) | DE3587380T2 (ko) |
ES (3) | ES8706792A1 (ko) |
FR (1) | FR2570703B1 (ko) |
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US4659815A (en) * | 1985-02-04 | 1987-04-21 | The President And Trustees Of The Miami University | Chromogenic aza-12-crown-4 ethers and method of using same for the detection of lithium |
GB8528804D0 (en) * | 1985-11-22 | 1985-12-24 | Amersham Int Plc | Compounds |
-
1984
- 1984-09-26 FR FR8414799A patent/FR2570703B1/fr not_active Expired
-
1985
- 1985-09-20 US US06/778,215 patent/US4927923A/en not_active Expired - Lifetime
- 1985-09-23 CA CA000491360A patent/CA1329593C/en not_active Expired - Lifetime
- 1985-09-23 AT AT85401838T patent/ATE90084T1/de not_active IP Right Cessation
- 1985-09-23 EP EP85401838A patent/EP0180492B1/fr not_active Expired - Lifetime
- 1985-09-23 DE DE85401838T patent/DE3587380T2/de not_active Expired - Lifetime
- 1985-09-25 ES ES547294A patent/ES8706792A1/es not_active Expired
- 1985-09-26 JP JP60213587A patent/JPH0655741B2/ja not_active Expired - Lifetime
- 1985-09-26 KR KR1019850007109A patent/KR930008210B1/ko not_active IP Right Cessation
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1987
- 1987-04-01 ES ES557485A patent/ES8801695A1/es not_active Expired
- 1987-04-01 ES ES557486A patent/ES8801938A1/es not_active Expired
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1993
- 1993-07-02 JP JP16372993A patent/JPH0714935B2/ja not_active Expired - Lifetime
- 1993-07-02 JP JP16373093A patent/JPH0715471B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
KR930008210B1 (ko) | 1993-08-26 |
US4927923A (en) | 1990-05-22 |
ES557485A0 (es) | 1988-02-16 |
JPH06199858A (ja) | 1994-07-19 |
DE3587380D1 (ko) | 1993-07-08 |
FR2570703B1 (fr) | 1988-07-08 |
JPH0714935B2 (ja) | 1995-02-22 |
CA1329593C (en) | 1994-05-17 |
FR2570703A1 (fr) | 1986-03-28 |
JPH0655741B2 (ja) | 1994-07-27 |
ES8801938A1 (es) | 1988-03-01 |
ES557486A0 (es) | 1988-03-01 |
ATE90084T1 (de) | 1993-06-15 |
JPS6187680A (ja) | 1986-05-06 |
JPH0715471B2 (ja) | 1995-02-22 |
ES8706792A1 (es) | 1987-07-01 |
ES8801695A1 (es) | 1988-02-16 |
JPH06184151A (ja) | 1994-07-05 |
EP0180492A1 (fr) | 1986-05-07 |
ES547294A0 (es) | 1987-07-01 |
DE3587380T2 (de) | 1994-01-05 |
EP0180492B1 (fr) | 1993-06-02 |
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