JPH0137694B2 - - Google Patents
Info
- Publication number
- JPH0137694B2 JPH0137694B2 JP58122464A JP12246483A JPH0137694B2 JP H0137694 B2 JPH0137694 B2 JP H0137694B2 JP 58122464 A JP58122464 A JP 58122464A JP 12246483 A JP12246483 A JP 12246483A JP H0137694 B2 JPH0137694 B2 JP H0137694B2
- Authority
- JP
- Japan
- Prior art keywords
- biotin
- reaction
- substance
- conjugate
- liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000126 substance Substances 0.000 claims description 113
- 238000006243 chemical reaction Methods 0.000 claims description 95
- 239000007788 liquid Substances 0.000 claims description 88
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 86
- 239000000376 reactant Substances 0.000 claims description 63
- 238000009739 binding Methods 0.000 claims description 54
- 239000011616 biotin Substances 0.000 claims description 43
- 229960002685 biotin Drugs 0.000 claims description 43
- 235000020958 biotin Nutrition 0.000 claims description 43
- 108090001008 Avidin Proteins 0.000 claims description 33
- 238000004458 analytical method Methods 0.000 claims description 31
- 239000000427 antigen Substances 0.000 claims description 29
- 102000036639 antigens Human genes 0.000 claims description 29
- 108091007433 antigens Proteins 0.000 claims description 29
- 239000003153 chemical reaction reagent Substances 0.000 claims description 19
- 238000002372 labelling Methods 0.000 claims description 19
- 238000003018 immunoassay Methods 0.000 claims description 12
- HUDPLKWXRLNSPC-UHFFFAOYSA-N 4-aminophthalhydrazide Chemical compound O=C1NNC(=O)C=2C1=CC(N)=CC=2 HUDPLKWXRLNSPC-UHFFFAOYSA-N 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 3
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical group O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 claims 2
- 230000009870 specific binding Effects 0.000 description 75
- 238000000034 method Methods 0.000 description 68
- 239000013076 target substance Substances 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 239000011541 reaction mixture Substances 0.000 description 45
- 230000000694 effects Effects 0.000 description 39
- 108090000790 Enzymes Proteins 0.000 description 37
- 102000004190 Enzymes Human genes 0.000 description 37
- 229940088598 enzyme Drugs 0.000 description 37
- 238000001514 detection method Methods 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 239000003446 ligand Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 25
- 230000027455 binding Effects 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 22
- 238000012544 monitoring process Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000010992 reflux Methods 0.000 description 15
- XUIIKFGFIJCVMT-GFCCVEGCSA-N D-thyroxine Chemical compound IC1=CC(C[C@@H](N)C(O)=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-GFCCVEGCSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 230000009137 competitive binding Effects 0.000 description 13
- 229940034208 thyroxine Drugs 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 10
- 239000000872 buffer Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- -1 ethyl carbonic anhydride Chemical compound 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920005654 Sephadex Polymers 0.000 description 6
- 239000012507 Sephadex™ Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012491 analyte Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229940109738 hematin Drugs 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 5
- 239000007982 barbital buffer Substances 0.000 description 5
- 239000013060 biological fluid Substances 0.000 description 5
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 5
- 229940008406 diethyl sulfate Drugs 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 5
- 229940057428 lactoperoxidase Drugs 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- YYNPMMANXKYXCN-LBPRGKRZSA-N (2s)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-2-[(2,2,2-trifluoroacetyl)amino]propanoic acid Chemical compound IC1=CC(C[C@@H](C(=O)O)NC(=O)C(F)(F)F)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 YYNPMMANXKYXCN-LBPRGKRZSA-N 0.000 description 4
- KMEBUNSLFRQSEM-UHFFFAOYSA-N 5-amino-2-methylisoindole-1,3-dione Chemical compound C1=C(N)C=C2C(=O)N(C)C(=O)C2=C1 KMEBUNSLFRQSEM-UHFFFAOYSA-N 0.000 description 4
- 108010023244 Lactoperoxidase Proteins 0.000 description 4
- 102000045576 Lactoperoxidases Human genes 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000012300 argon atmosphere Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000002860 competitive effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 108010029942 microperoxidase Proteins 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000000941 radioactive substance Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- BMUDPLZKKRQECS-UHFFFAOYSA-K 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid iron(3+) hydroxide Chemical compound [OH-].[Fe+3].[N-]1C2=C(C)C(CCC(O)=O)=C1C=C([N-]1)C(CCC(O)=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 BMUDPLZKKRQECS-UHFFFAOYSA-K 0.000 description 3
- MQJSMQLGNZNTFD-UHFFFAOYSA-N 4-amino-2-methylisoindole-1,3-dione Chemical compound C1=CC(N)=C2C(=O)N(C)C(=O)C2=C1 MQJSMQLGNZNTFD-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000005415 bioluminescence Methods 0.000 description 3
- 230000029918 bioluminescence Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 229950006238 nadide Drugs 0.000 description 3
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- 229940088594 vitamin Drugs 0.000 description 3
- 229930003231 vitamin Natural products 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 2
- JBCHWGTZAAZJKG-UHFFFAOYSA-N 2-methyl-5-nitroisoindole-1,3-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(C)C(=O)C2=C1 JBCHWGTZAAZJKG-UHFFFAOYSA-N 0.000 description 2
- OMTDIBZSUZNVJK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-oxobutanoic acid Chemical compound COC1=CC=C(C(=O)CCC(O)=O)C=C1 OMTDIBZSUZNVJK-UHFFFAOYSA-N 0.000 description 2
- LZHMNCJMXQKSBY-UHFFFAOYSA-N 4-(4-methoxyphenyl)butanoic acid Chemical compound COC1=CC=C(CCCC(O)=O)C=C1 LZHMNCJMXQKSBY-UHFFFAOYSA-N 0.000 description 2
- GQBONCZDJQXPLV-UHFFFAOYSA-N 4-aminoisoindole-1,3-dione Chemical compound NC1=CC=CC2=C1C(=O)NC2=O GQBONCZDJQXPLV-UHFFFAOYSA-N 0.000 description 2
- FBPXWFAFOYGKTD-UHFFFAOYSA-N 5-(ethylamino)-2-methylisoindole-1,3-dione Chemical compound CCNC1=CC=C2C(=O)N(C)C(=O)C2=C1 FBPXWFAFOYGKTD-UHFFFAOYSA-N 0.000 description 2
- MMVIDXVHQANYAE-UHFFFAOYSA-N 5-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)OC(=O)C2=C1 MMVIDXVHQANYAE-UHFFFAOYSA-N 0.000 description 2
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YTNIXZGTHTVJBW-SCRDCRAPSA-N FMNH2 Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2NC2=C1NC(=O)NC2=O YTNIXZGTHTVJBW-SCRDCRAPSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- WTTHUUZTJLNOPO-UFLZEWODSA-N NC1=C(C(C(=O)O)=CC=C1)C(=O)O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 Chemical compound NC1=C(C(C(=O)O)=CC=C1)C(=O)O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 WTTHUUZTJLNOPO-UFLZEWODSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 229960004424 carbon dioxide Drugs 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- QLAFJLKSTOAENJ-UHFFFAOYSA-N dimethyl 7-aminonaphthalene-1,2-dicarboxylate Chemical compound C1=CC(N)=CC2=C(C(=O)OC)C(C(=O)OC)=CC=C21 QLAFJLKSTOAENJ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 2
- FVTCRASFADXXNN-UHFFFAOYSA-N flavin mononucleotide Natural products OP(=O)(O)OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-UHFFFAOYSA-N 0.000 description 2
- 239000011768 flavin mononucleotide Substances 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- FEZIYDSIDIJXQH-UHFFFAOYSA-N methyl 4-(4-methoxyphenyl)butanoate Chemical compound COC(=O)CCCC1=CC=C(OC)C=C1 FEZIYDSIDIJXQH-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000003127 radioimmunoassay Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 235000019231 riboflavin-5'-phosphate Nutrition 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
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Classifications
-
- 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
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57200875A | 1975-04-28 | 1975-04-28 | |
| US572008 | 1975-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5942454A JPS5942454A (ja) | 1984-03-09 |
| JPH0137694B2 true JPH0137694B2 (sv) | 1989-08-09 |
Family
ID=24285954
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51047347A Expired JPS604939B2 (ja) | 1975-04-28 | 1976-04-27 | 液体中のハプテンヌは抗原を分析するための均一系免疫分析方法及びそれに用いる試薬 |
| JP51047348A Expired JPS6052378B2 (ja) | 1975-04-28 | 1976-04-27 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
| JP58122466A Granted JPS5951354A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
| JP58122464A Granted JPS5942454A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための均一系免疫分析方法及び試薬 |
| JP58122463A Granted JPS5942453A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための均一系免疫分析方法及び試薬 |
| JP58122465A Granted JPS5951353A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51047347A Expired JPS604939B2 (ja) | 1975-04-28 | 1976-04-27 | 液体中のハプテンヌは抗原を分析するための均一系免疫分析方法及びそれに用いる試薬 |
| JP51047348A Expired JPS6052378B2 (ja) | 1975-04-28 | 1976-04-27 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
| JP58122466A Granted JPS5951354A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58122463A Granted JPS5942453A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための均一系免疫分析方法及び試薬 |
| JP58122465A Granted JPS5951353A (ja) | 1975-04-28 | 1983-07-07 | 液体中のハプテン又は抗原を分析するための不均一系免疫分析方法及び試薬 |
Country Status (23)
| Country | Link |
|---|---|
| JP (6) | JPS604939B2 (sv) |
| AT (1) | AT357685B (sv) |
| AU (2) | AU509182B2 (sv) |
| BE (1) | BE841179A (sv) |
| BR (1) | BR7602561A (sv) |
| CA (2) | CA1082577A (sv) |
| CH (1) | CH635438A5 (sv) |
| DD (1) | DD125231A5 (sv) |
| DE (3) | DE2660548C2 (sv) |
| DK (3) | DK149969C (sv) |
| ES (1) | ES447378A1 (sv) |
| FI (1) | FI68324C (sv) |
| FR (1) | FR2332533A1 (sv) |
| GB (2) | GB1552607A (sv) |
| HU (1) | HU179542B (sv) |
| IE (1) | IE42544B1 (sv) |
| IL (1) | IL49354A (sv) |
| IN (1) | IN142734B (sv) |
| IT (1) | IT1064132B (sv) |
| LU (1) | LU74834A1 (sv) |
| NL (1) | NL181281C (sv) |
| SE (3) | SE440280B (sv) |
| ZA (1) | ZA762030B (sv) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51668A (en) | 1977-03-16 | 1981-12-31 | Israel State | Analytical method for the quantitative determination of immunogens and antibodies and a kit therefor |
| SE7811630L (sv) * | 1977-11-17 | 1979-05-18 | Welsh Nat School Med | Metod for uppteckt eller mengdbestemning av substanser med anvendning av merkningsteknik |
| USRE34394E (en) * | 1978-01-23 | 1993-09-28 | Baxter Diagnostics Inc. | Method and composition for double receptor, specific binding assays |
| US4233402A (en) * | 1978-04-05 | 1980-11-11 | Syva Company | Reagents and method employing channeling |
| AU531777B2 (en) * | 1978-04-05 | 1983-09-08 | Syva Co. | Label/solid conjugate immunoassay system |
| FR2422956A1 (fr) * | 1978-04-13 | 1979-11-09 | Pasteur Institut | Procede de detection et de caracterisation d'un acide nucleique ou d'une sequence de celui-ci, et reactif enzymatique pour la mise en oeuvre de ce procede |
| US5605800A (en) * | 1978-04-13 | 1997-02-25 | Institut Pasteur | Method of detecting and characterizing a nucleic acid or a sequence of the latter, and enzymatic reactant for the application of this method |
| IL57571A (en) * | 1978-06-22 | 1983-03-31 | Miles Lab | Flavin adenine dinucleotide-labeled conjugates and their use in a homogeneous immunoassay method for determining haptens |
| IL57570A (en) * | 1978-06-22 | 1982-07-30 | Miles Lab | Method and reagent for specific binding assay with a prosthetic group as a label component |
| US4225485A (en) * | 1978-07-24 | 1980-09-30 | Miles Laboratories, Inc. | Chemiluminescent naphthalene-1,2-dicarboxylic acid hydrazide-labeled polypeptides and proteins |
| US4334069A (en) * | 1978-07-24 | 1982-06-08 | Miles Laboratories, Inc. | Chemiluminescent phthalhydrazide-labeled hapten conjugates |
| US4228237A (en) * | 1978-09-21 | 1980-10-14 | Calbiochem-Behring Corp. | Methods for the detection and determination of ligands |
| US4288538A (en) | 1979-01-31 | 1981-09-08 | Baxter Travenol Laboratories, Inc. | Test method and composition therefor |
| US4273866A (en) * | 1979-02-05 | 1981-06-16 | Abbott Laboratories | Ligand analog-irreversible enzyme inhibitor conjugates and methods for use |
| US4446231A (en) * | 1979-10-03 | 1984-05-01 | Self Colin H | Immunoassay using an amplified cyclic detection system |
| GB2059421A (en) * | 1979-10-03 | 1981-04-23 | Self C H | Assay method and reagents therefor |
| US4259232A (en) * | 1979-10-23 | 1981-03-31 | Miles Laboratories, Inc. | Flavin adenine dinucleotide-labeled protein and polypeptide conjugates |
| AT367796B (de) * | 1979-10-29 | 1982-07-26 | List Hans | Verfahren zur bestimmung einer stoffkonzentration in einer loesung |
| EP0040224A4 (en) * | 1979-11-19 | 1982-09-09 | Prince Charles Hospital Dev Ct | IMPROVED PROCESS FOR IMMUNOLOGICAL ANALYSIS OF NON-HOMOGENOUS ENZYMES. |
| US4299916A (en) * | 1979-12-26 | 1981-11-10 | Syva Company | Preferential signal production on a surface in immunoassays |
| DK256581A (da) * | 1980-06-13 | 1981-12-14 | Nat Res Dev | Bindingsanalyse |
| EP0049606A1 (en) * | 1980-10-02 | 1982-04-14 | Colin Henry Self | Detection method, use and diagnostic aid |
| CA1183450A (en) * | 1980-10-30 | 1985-03-05 | Alfred C. Greenquist | Homogeneous specific binding assay device and method |
| US4404278A (en) * | 1980-11-24 | 1983-09-13 | Syva Company | Methods and compositions for assaying for the production of 1,4-dihydropyridyl |
| US4378458A (en) * | 1981-03-30 | 1983-03-29 | Baker Instruments Corporation | Novel chromogenic and/or fluorogenic substrates for monitoring catalytic or enzymatic activity |
| US4366243A (en) | 1981-04-17 | 1982-12-28 | Miles Laboratories, Inc. | Stabilization of glucose oxidase apoenzyme |
| US4711955A (en) * | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
| CA1219824A (en) * | 1981-04-17 | 1987-03-31 | David C. Ward | Modified nucleotides and methods of preparing and using same |
| ATE48140T1 (de) * | 1981-04-17 | 1989-12-15 | Univ Yale | Modifizierte nukleotide und verfahren zu ihrer herstellung und anwendung. |
| JPS5818167A (ja) * | 1981-07-24 | 1983-02-02 | Fuji Photo Film Co Ltd | 分析フイルム及びこれを用いる分析方法 |
| JPS5877843U (ja) * | 1981-11-20 | 1983-05-26 | 株式会社三協精機製作所 | テ−プレコ−ダ |
| GB2112779B (en) * | 1981-12-11 | 1986-10-15 | Welsh Nat School Med | Aryl acridinium esters as luminescent labelling materials |
| FR2519004B1 (fr) * | 1981-12-29 | 1985-09-27 | Pasteur Institut | Acide adenosine 5'-triphosphorique modifie et procede de dosage de substances biologiques susceptibles de fixer des produits de degradation de l'acide adenosine 5'-triphosphorique |
| FR2519005B1 (fr) * | 1981-12-29 | 1985-10-25 | Pasteur Institut | Fragments d'adn marques a l'une au moins de leurs extremites par des ribonucleotides modifies reconnaissables par des molecules affines et procede pour realiser une analyse de tels fragments d'adn |
| US5650270A (en) * | 1982-02-01 | 1997-07-22 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
| US4709016A (en) * | 1982-02-01 | 1987-11-24 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
| IL67289A (en) * | 1982-03-18 | 1985-12-31 | Miles Lab | Homogeneous immunoassay with labeled monoclonal anti-analyte |
| CA1223831A (en) * | 1982-06-23 | 1987-07-07 | Dean Engelhardt | Modified nucleotides, methods of preparing and utilizing and compositions containing the same |
| US4495281A (en) * | 1982-10-21 | 1985-01-22 | Miles Laboratories, Inc. | Tricyclic antidepressant drug immunogens, antibodies, labeled conjugates, and related derivatives |
| US4994373A (en) | 1983-01-27 | 1991-02-19 | Enzo Biochem, Inc. | Method and structures employing chemically-labelled polynucleotide probes |
| US4828979A (en) * | 1984-11-08 | 1989-05-09 | Life Technologies, Inc. | Nucleotide analogs for nucleic acid labeling and detection |
| EP0201211A1 (en) * | 1985-04-10 | 1986-11-12 | Whittaker Corporation | Method and compositions for visual solid phase immunoassays based on luminescent microspheric particles |
| JPS61271457A (ja) * | 1985-05-28 | 1986-12-01 | Olympus Optical Co Ltd | 免疫学的分析方法 |
| JPH06100599B2 (ja) * | 1985-06-27 | 1994-12-12 | 東亜医用電子株式会社 | 体液成分の測定方法 |
| JPS6321559A (ja) * | 1986-07-16 | 1988-01-29 | Matsushita Electric Ind Co Ltd | ハプテンの酵素免疫測定法 |
| US6002007A (en) * | 1988-02-20 | 1999-12-14 | Dade Behring Marburg Gmbh | Special chemiluminescent acridine derivatives and the use thereof in luminescence immunoassays |
| DE3844954C2 (de) * | 1988-02-20 | 1998-07-16 | Hoechst Ag | Spezielle chemilumineszierende Acridinderivate und ihre Verwendung in Lumineszenzimmunoassays |
| JP2525678B2 (ja) * | 1989-10-03 | 1996-08-21 | 富士写真フイルム株式会社 | 免疫測定装置 |
| US6596490B2 (en) | 2000-07-14 | 2003-07-22 | Applied Gene Technologies, Inc. | Nucleic acid hairpin probes and uses thereof |
| US6380377B1 (en) | 2000-07-14 | 2002-04-30 | Applied Gene Technologies, Inc. | Nucleic acid hairpin probes and uses thereof |
| CN100494399C (zh) | 2003-06-30 | 2009-06-03 | 清华大学 | 一种基于dna芯片的基因分型方法及其应用 |
| US7799534B2 (en) | 2006-05-09 | 2010-09-21 | Beckman Coulter, Inc. | Nonseparation assay methods |
| US7732153B2 (en) | 2006-05-09 | 2010-06-08 | Beckman Coulter, Inc. | Nonseparation assay methods |
| JP6214449B2 (ja) * | 2014-03-31 | 2017-10-18 | シスメックス株式会社 | キナーゼ活性の測定方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL154600B (nl) * | 1971-02-10 | 1977-09-15 | Organon Nv | Werkwijze voor het aantonen en bepalen van specifiek bindende eiwitten en hun corresponderende bindbare stoffen. |
| US3817837A (en) * | 1971-05-14 | 1974-06-18 | Syva Corp | Enzyme amplification assay |
| US3880934A (en) * | 1972-02-10 | 1975-04-29 | Syntex Inc | Nitrophenyloxy-butanediols |
| JPS5147348A (ja) * | 1974-10-21 | 1976-04-22 | Nippon Electric Co | Johoshorisochi |
| JPS5147347A (ja) * | 1974-10-21 | 1976-04-22 | Nippon Electric Co | Johoshorisochi |
-
1975
- 1975-09-30 IN IN1874/CAL/75A patent/IN142734B/en unknown
-
1976
- 1976-04-02 IE IE696/76A patent/IE42544B1/en unknown
- 1976-04-05 ZA ZA762030A patent/ZA762030B/xx unknown
- 1976-04-05 IL IL49354A patent/IL49354A/xx unknown
- 1976-04-07 CA CA249,745A patent/CA1082577A/en not_active Expired
- 1976-04-07 CA CA249,744A patent/CA1078712A/en not_active Expired
- 1976-04-21 CH CH497976A patent/CH635438A5/de not_active IP Right Cessation
- 1976-04-23 GB GB16610/76A patent/GB1552607A/en not_active Expired
- 1976-04-23 GB GB16609/76A patent/GB1548741A/en not_active Expired
- 1976-04-26 FI FI761148A patent/FI68324C/fi not_active IP Right Cessation
- 1976-04-26 IT IT49195/76A patent/IT1064132B/it active
- 1976-04-26 NL NLAANVRAGE7604420,A patent/NL181281C/xx not_active IP Right Cessation
- 1976-04-26 LU LU74834A patent/LU74834A1/xx unknown
- 1976-04-27 DK DK189176A patent/DK149969C/da not_active IP Right Cessation
- 1976-04-27 SE SE7604841A patent/SE440280B/sv not_active IP Right Cessation
- 1976-04-27 DE DE2660548A patent/DE2660548C2/de not_active Expired
- 1976-04-27 JP JP51047347A patent/JPS604939B2/ja not_active Expired
- 1976-04-27 ES ES447378A patent/ES447378A1/es not_active Expired
- 1976-04-27 DE DE2618419A patent/DE2618419C2/de not_active Expired
- 1976-04-27 BR BR2561/76A patent/BR7602561A/pt unknown
- 1976-04-27 BE BE166499A patent/BE841179A/xx not_active IP Right Cessation
- 1976-04-27 HU HU76MI600A patent/HU179542B/hu unknown
- 1976-04-27 AU AU13352/76A patent/AU509182B2/en not_active Expired
- 1976-04-27 JP JP51047348A patent/JPS6052378B2/ja not_active Expired
- 1976-04-27 FR FR7612441A patent/FR2332533A1/fr active Granted
- 1976-04-27 AT AT309376A patent/AT357685B/de not_active IP Right Cessation
- 1976-04-27 DD DD192528A patent/DD125231A5/xx unknown
- 1976-04-27 AU AU13353/76A patent/AU502726B2/en not_active Expired
- 1976-04-27 DE DE2618511A patent/DE2618511C3/de not_active Expired
-
1980
- 1980-10-21 SE SE8007397A patent/SE451895B/sv not_active IP Right Cessation
- 1980-10-21 SE SE8007396A patent/SE447510B/sv not_active IP Right Cessation
-
1981
- 1981-12-23 DK DK576181A patent/DK158366C/da not_active IP Right Cessation
- 1981-12-23 DK DK576281A patent/DK150808C/da not_active IP Right Cessation
-
1983
- 1983-07-07 JP JP58122466A patent/JPS5951354A/ja active Granted
- 1983-07-07 JP JP58122464A patent/JPS5942454A/ja active Granted
- 1983-07-07 JP JP58122463A patent/JPS5942453A/ja active Granted
- 1983-07-07 JP JP58122465A patent/JPS5951353A/ja active Granted
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