JPH0137693B2 - - Google Patents
Info
- Publication number
- JPH0137693B2 JPH0137693B2 JP58122463A JP12246383A JPH0137693B2 JP H0137693 B2 JPH0137693 B2 JP H0137693B2 JP 58122463 A JP58122463 A JP 58122463A JP 12246383 A JP12246383 A JP 12246383A JP H0137693 B2 JPH0137693 B2 JP H0137693B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- conjugate
- substance
- liquid
- specific binding
- 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 131
- 239000007788 liquid Substances 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 88
- 102000004190 Enzymes Human genes 0.000 claims description 80
- 108090000790 Enzymes Proteins 0.000 claims description 80
- 238000009739 binding Methods 0.000 claims description 67
- 239000000427 antigen Substances 0.000 claims description 35
- 239000003153 chemical reaction reagent Substances 0.000 claims description 34
- 102000036639 antigens Human genes 0.000 claims description 32
- 108091007433 antigens Proteins 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 32
- 238000002372 labelling Methods 0.000 claims description 20
- 238000003018 immunoassay Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000009471 action Effects 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 3
- 239000007850 fluorescent dye Substances 0.000 claims description 2
- UPSFMJHZUCSEHU-JYGUBCOQSA-N n-[(2s,3r,4r,5s,6r)-2-[(2r,3s,4r,5r,6s)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-(4-methyl-2-oxochromen-7-yl)oxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide Chemical compound CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](NC(C)=O)[C@H](OC=2C=C3OC(=O)C=C(C)C3=CC=2)O[C@@H]1CO UPSFMJHZUCSEHU-JYGUBCOQSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 153
- 230000009870 specific binding Effects 0.000 description 100
- 239000011541 reaction mixture Substances 0.000 description 92
- 239000000376 reactant Substances 0.000 description 78
- 239000013076 target substance Substances 0.000 description 71
- 230000000694 effects Effects 0.000 description 65
- 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 description 54
- 238000004458 analytical method Methods 0.000 description 54
- 229960002685 biotin Drugs 0.000 description 39
- 239000011616 biotin Substances 0.000 description 39
- 238000001514 detection method Methods 0.000 description 37
- 239000003446 ligand Substances 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 235000020958 biotin Nutrition 0.000 description 27
- 230000027455 binding Effects 0.000 description 26
- 238000012544 monitoring process Methods 0.000 description 26
- 108090001008 Avidin Proteins 0.000 description 25
- 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 25
- 230000008859 change Effects 0.000 description 25
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- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 25
- 230000003287 optical effect Effects 0.000 description 25
- 229950006238 nadide Drugs 0.000 description 24
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 23
- 239000000872 buffer Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 230000009137 competitive binding Effects 0.000 description 15
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 14
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 14
- 238000006555 catalytic reaction Methods 0.000 description 13
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- 230000002255 enzymatic effect Effects 0.000 description 11
- 108090000371 Esterases Proteins 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 229960005456 sisomicin Drugs 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000002860 competitive effect Effects 0.000 description 9
- 238000006911 enzymatic reaction Methods 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229930182566 Gentamicin Natural products 0.000 description 8
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 8
- 229960002518 gentamicin Drugs 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- ZYUWUKIAUDIXCQ-UHFFFAOYSA-N N-(2,4-dinitrophenyl)aminohexanoic acid Chemical compound OC(=O)CCCCCNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ZYUWUKIAUDIXCQ-UHFFFAOYSA-N 0.000 description 7
- DAYLJWODMCOQEW-TURQNECASA-N NMN zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)([O-])=O)O2)O)=C1 DAYLJWODMCOQEW-TURQNECASA-N 0.000 description 7
- URWAJWIAIPFPJE-UHFFFAOYSA-N Rickamicin Natural products O1CC(O)(C)C(NC)C(O)C1OC1C(O)C(OC2C(CC=C(CN)O2)N)C(N)CC1N URWAJWIAIPFPJE-UHFFFAOYSA-N 0.000 description 7
- 229930192786 Sisomicin Natural products 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229960000890 hydrocortisone Drugs 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- URWAJWIAIPFPJE-YFMIWBNJSA-N sisomycin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC=C(CN)O2)N)[C@@H](N)C[C@H]1N URWAJWIAIPFPJE-YFMIWBNJSA-N 0.000 description 7
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 7
- XSSZEVXYIHNWQO-UHFFFAOYSA-N 3-(2,4-dinitroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O XSSZEVXYIHNWQO-UHFFFAOYSA-N 0.000 description 6
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 6
- 241000283690 Bos taurus Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 102000005936 beta-Galactosidase Human genes 0.000 description 6
- 108010005774 beta-Galactosidase Proteins 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- CEOHLRWDZNGQOD-UHFFFAOYSA-N 2-(ethylamino)-2,2-dihydroxyacetic acid Chemical compound CCNC(O)(O)C(O)=O CEOHLRWDZNGQOD-UHFFFAOYSA-N 0.000 description 5
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013060 biological fluid Substances 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000012921 fluorescence analysis Methods 0.000 description 5
- GKQWYZBANWAFMQ-UHFFFAOYSA-M lithium;2-hydroxypropanoate Chemical compound [Li+].CC(O)C([O-])=O GKQWYZBANWAFMQ-UHFFFAOYSA-M 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 4
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000941 radioactive substance Substances 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
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- 125000005647 linker group Chemical group 0.000 description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
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- 229910052760 oxygen Inorganic materials 0.000 description 3
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
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- 229940088594 vitamin Drugs 0.000 description 3
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- SPEHZVWWLGJQLD-BSLNIGMPSA-N (2r,3r,4s,5r)-5-[[[[(2r,3s,4r,5r)-5-[6-(2-aminoethylamino)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxymethyl]-2-(3-carbamoylpyridin-1-ium-1-yl)-4-hydroxyoxolan-3-olate Chemical compound [N+]1([C@@H]2O[C@@H]([C@H]([C@H]2[O-])O)COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)N2C=3N=CN=C(C=3N=C2)NCCN)=CC=CC(C(N)=O)=C1 SPEHZVWWLGJQLD-BSLNIGMPSA-N 0.000 description 2
- 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
- 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 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-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
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 2
- 108010021809 Alcohol dehydrogenase Proteins 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
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- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
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- 230000003197 catalytic effect Effects 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
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- 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
- LKKVGKXCMYHKSL-LLZRLKDCSA-N gentamycin A Chemical compound O[C@H]1[C@H](NC)[C@@H](O)CO[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](N)C[C@H]1N LKKVGKXCMYHKSL-LLZRLKDCSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 150000003839 salts Chemical class 0.000 description 2
- 239000013077 target material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Physics & Mathematics (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Saccharide Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
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 |
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JPS5942453A JPS5942453A (ja) | 1984-03-09 |
JPH0137693B2 true JPH0137693B2 (de) | 1989-08-09 |
Family
ID=24285954
Family Applications (6)
Application Number | Title | Priority Date | Filing Date |
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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 |
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 |
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 |
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 |
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 |
Family Applications Before (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
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 |
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 |
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 |
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 |
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 |
Country Status (23)
Country | Link |
---|---|
JP (6) | JPS6052378B2 (de) |
AT (1) | AT357685B (de) |
AU (2) | AU502726B2 (de) |
BE (1) | BE841179A (de) |
BR (1) | BR7602561A (de) |
CA (2) | CA1078712A (de) |
CH (1) | CH635438A5 (de) |
DD (1) | DD125231A5 (de) |
DE (3) | DE2660548C2 (de) |
DK (3) | DK149969C (de) |
ES (1) | ES447378A1 (de) |
FI (1) | FI68324C (de) |
FR (1) | FR2332533A1 (de) |
GB (2) | GB1548741A (de) |
HU (1) | HU179542B (de) |
IE (1) | IE42544B1 (de) |
IL (1) | IL49354A (de) |
IN (1) | IN142734B (de) |
IT (1) | IT1064132B (de) |
LU (1) | LU74834A1 (de) |
NL (1) | NL181281C (de) |
SE (3) | SE440280B (de) |
ZA (1) | ZA762030B (de) |
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 |
AU531777B2 (en) * | 1978-04-05 | 1983-09-08 | Syva Co. | Label/solid conjugate immunoassay system |
US4233402A (en) * | 1978-04-05 | 1980-11-11 | Syva Company | Reagents and method employing channeling |
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 |
DE2924332A1 (de) * | 1978-06-22 | 1980-01-03 | Miles Lab | Flavin-adenin-dinukleotid-markiertes konjugat und dessen verwendung in spezifischen bindungsversuchen |
DE2924249C2 (de) * | 1978-06-22 | 1989-04-27 | Miles, Inc., Elkhart, Ind., Us | Spezifische bindungs-untersuchungsmethode zur bestimmung eines liganden in einem fluessigen medium und reagentien zur durchfuehrung dieser methode |
US4334069A (en) * | 1978-07-24 | 1982-06-08 | Miles Laboratories, Inc. | Chemiluminescent phthalhydrazide-labeled hapten conjugates |
US4225485A (en) * | 1978-07-24 | 1980-09-30 | Miles Laboratories, Inc. | Chemiluminescent naphthalene-1,2-dicarboxylic acid hydrazide-labeled polypeptides and proteins |
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 |
GB2059421A (en) * | 1979-10-03 | 1981-04-23 | Self C H | Assay method and reagents therefor |
US4446231A (en) * | 1979-10-03 | 1984-05-01 | Self Colin H | Immunoassay using an amplified cyclic detection system |
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 |
WO1981001414A1 (en) * | 1979-11-19 | 1981-05-28 | Charles Hospital Dev | An improved method of non homogenous enzyme immunoassay |
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 (de) * | 1980-10-02 | 1982-04-14 | Colin Henry Self | Nachweisverfahren, Anwendung und diagnostisches Hilfsmittel |
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 |
EP0329198B1 (de) * | 1981-04-17 | 1998-06-10 | Yale University | Basenmodifizierte Oligo- und Polynucleotide und Verfahren zu ihrer Herstellung und Verwendung |
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 |
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 |
DE3279029D1 (en) * | 1981-12-11 | 1988-10-20 | Welsh Nat School Med | Luminescent labelling materials and procedures |
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 |
US4709016A (en) * | 1982-02-01 | 1987-11-24 | Northeastern University | Molecular analytical release tags and their use in chemical analysis |
US5650270A (en) * | 1982-02-01 | 1997-07-22 | 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 (de) * | 1985-04-10 | 1986-11-12 | Whittaker Corporation | Methode und Zusammensetzung für visuelle Festphasen-Immunoassays auf der Basis lumineszierender kugelförmiger Mikropartikel |
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 |
DE3844954C2 (de) * | 1988-02-20 | 1998-07-16 | Hoechst Ag | Spezielle chemilumineszierende Acridinderivate und ihre Verwendung in Lumineszenzimmunoassays |
US6002007A (en) * | 1988-02-20 | 1999-12-14 | Dade Behring Marburg Gmbh | Special chemiluminescent acridine derivatives and the use thereof in luminescence immunoassays |
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 |
US6380377B1 (en) | 2000-07-14 | 2002-04-30 | Applied Gene Technologies, Inc. | Nucleic acid hairpin probes and uses thereof |
US6596490B2 (en) | 2000-07-14 | 2003-07-22 | 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 IL IL49354A patent/IL49354A/xx unknown
- 1976-04-05 ZA ZA762030A patent/ZA762030B/xx unknown
- 1976-04-07 CA CA249,744A patent/CA1078712A/en not_active Expired
- 1976-04-07 CA CA249,745A patent/CA1082577A/en not_active Expired
- 1976-04-21 CH CH497976A patent/CH635438A5/de not_active IP Right Cessation
- 1976-04-23 GB GB16609/76A patent/GB1548741A/en not_active Expired
- 1976-04-23 GB GB16610/76A patent/GB1552607A/en not_active Expired
- 1976-04-26 LU LU74834A patent/LU74834A1/xx unknown
- 1976-04-26 IT IT49195/76A patent/IT1064132B/it active
- 1976-04-26 FI FI761148A patent/FI68324C/fi not_active IP Right Cessation
- 1976-04-26 NL NLAANVRAGE7604420,A patent/NL181281C/xx not_active IP Right Cessation
- 1976-04-27 BE BE166499A patent/BE841179A/xx not_active IP Right Cessation
- 1976-04-27 JP JP51047348A patent/JPS6052378B2/ja not_active Expired
- 1976-04-27 DE DE2660548A patent/DE2660548C2/de 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 BR BR2561/76A patent/BR7602561A/pt unknown
- 1976-04-27 DK DK189176A patent/DK149969C/da not_active IP Right Cessation
- 1976-04-27 HU HU76MI600A patent/HU179542B/hu unknown
- 1976-04-27 DE DE2618511A patent/DE2618511C3/de not_active Expired
- 1976-04-27 SE SE7604841A patent/SE440280B/xx not_active IP Right Cessation
- 1976-04-27 JP JP51047347A patent/JPS604939B2/ja not_active Expired
- 1976-04-27 AU AU13353/76A patent/AU502726B2/en not_active Expired
- 1976-04-27 ES ES447378A patent/ES447378A1/es not_active Expired
- 1976-04-27 DD DD192528A patent/DD125231A5/xx unknown
- 1976-04-27 DE DE2618419A patent/DE2618419C2/de not_active Expired
- 1976-04-27 AU AU13352/76A patent/AU509182B2/en 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 DK576281A patent/DK150808C/da not_active IP Right Cessation
- 1981-12-23 DK DK576181A patent/DK158366C/da not_active IP Right Cessation
-
1983
- 1983-07-07 JP JP58122466A patent/JPS5951354A/ja active Granted
- 1983-07-07 JP JP58122465A patent/JPS5951353A/ja active Granted
- 1983-07-07 JP JP58122464A patent/JPS5942454A/ja active Granted
- 1983-07-07 JP JP58122463A patent/JPS5942453A/ja active Granted
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