JPS6313997B2 - - Google Patents

Info

Publication number: JPS6313997B2
Authority: JP; Japan
Prior art keywords: monodtpa; acid; dtpa; diethylenetriamine; hereinafter referred
Prior art date: 1985-10-23
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

Application number

JP25323186A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62174079A (ja

Inventor

Isao Sakata

Susumu Nakajima

Koichi Koshimizu

Natsuki Samejima

Kazumi Inohara

Hiroyuki Takada

Hirohiko Yamauchi

Nobuo Ueda

Masaaki Hatsue

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

TOYO HATSUKA KOGYO KK

Original Assignee

TOYO HATSUKA KOGYO KK

Priority date (The priority date 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 date listed.)

1985-10-23

Filing date

1986-10-23

Publication date

1988-03-29

1986-10-23 Application filed by TOYO HATSUKA KOGYO KK filed Critical TOYO HATSUKA KOGYO KK

1987-07-30 Publication of JPS62174079A publication Critical patent/JPS62174079A/ja

1988-03-29 Publication of JPS6313997B2 publication Critical patent/JPS6313997B2/ja

Status Granted legal-status Critical Current

Links

-1 1-iodoethyl Chemical group 0.000 claims description 48
229910052751 metal Inorganic materials 0.000 claims description 43
239000002184 metal Substances 0.000 claims description 43
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical group N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 45
206010028980 Neoplasm Diseases 0.000 description 40
201000011510 cancer Diseases 0.000 description 36
230000002285 radioactive effect Effects 0.000 description 34
239000004480 active ingredient Substances 0.000 description 32
239000000032 diagnostic agent Substances 0.000 description 29
229940039227 diagnostic agent Drugs 0.000 description 29
239000003795 chemical substances by application Substances 0.000 description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
210000000056 organ Anatomy 0.000 description 22
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 20
VAJVGAQAYOAJQI-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-3,8,13,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical compound N1C(C=C2C(C)=CC(N2)=CC=2C(=C(CCC(O)=O)C(=C3)N=2)C)=CC(C)=C1C=C1C(C)=C(CCC(O)=O)C3=N1 VAJVGAQAYOAJQI-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
150000004032 porphyrins Chemical group 0.000 description 18
229960003330 pentetic acid Drugs 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
238000000034 method Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
150000004696 coordination complex Chemical class 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
239000000203 mixture Substances 0.000 description 12
150000004033 porphyrin derivatives Chemical class 0.000 description 12
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 11
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 11
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 10
239000000243 solution Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
241000699800 Cricetinae Species 0.000 description 9
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 9
108010008488 Glycylglycine Proteins 0.000 description 9
229940079593 drug Drugs 0.000 description 9
239000003814 drug Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
YEEGWNXDUZONAA-RYDPDVNUSA-K Gallium Citrate (67 Ga) Chemical compound [67Ga+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YEEGWNXDUZONAA-RYDPDVNUSA-K 0.000 description 8
206010034972 Photosensitivity reaction Diseases 0.000 description 8
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000002372 labelling Methods 0.000 description 8
208000007578 phototoxic dermatitis Diseases 0.000 description 8
231100000018 phototoxicity Toxicity 0.000 description 8
229910021617 Indium monochloride Inorganic materials 0.000 description 7
239000013078 crystal Substances 0.000 description 7
APHGZSBLRQFRCA-UHFFFAOYSA-M indium(1+);chloride Chemical compound [In]Cl APHGZSBLRQFRCA-UHFFFAOYSA-M 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000012360 testing method Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
229960003569 hematoporphyrin Drugs 0.000 description 5
239000004471 Glycine Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 4
238000009826 distribution Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
239000002905 metal composite material Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000011148 porous material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical compound CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
229940024606 amino acid Drugs 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000007979 citrate buffer Substances 0.000 description 3
238000002224 dissection Methods 0.000 description 3
230000005284 excitation Effects 0.000 description 3
238000002189 fluorescence spectrum Methods 0.000 description 3
235000013922 glutamic acid Nutrition 0.000 description 3
239000004220 glutamic acid Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
FTEDXVNDVHYDQW-UHFFFAOYSA-N BAPTA Chemical compound OC(=O)CN(CC(O)=O)C1=CC=CC=C1OCCOC1=CC=CC=C1N(CC(O)=O)CC(O)=O FTEDXVNDVHYDQW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000003745 diagnosis Methods 0.000 description 2
239000000539 dimer Substances 0.000 description 2
PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 2
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
IFQUWYZCAGRUJN-UHFFFAOYSA-N ethylenediaminediacetic acid Chemical compound OC(=O)CNCCNCC(O)=O IFQUWYZCAGRUJN-UHFFFAOYSA-N 0.000 description 2
229910052733 gallium Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052738 indium Inorganic materials 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
229910001510 metal chloride Inorganic materials 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 2
JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical group N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
229910052710 silicon Inorganic materials 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
229910052718 tin Inorganic materials 0.000 description 2
238000011179 visual inspection Methods 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
XMGQYMWWDOXHJM-SNVBAGLBSA-N (-)-α-limonene Chemical compound CC(=C)[C@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-SNVBAGLBSA-N 0.000 description 1
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
OQSAAKTZXLIZJJ-OKWSDYJOSA-N 2-[1-[3-deuterio-4-[1-(2-hydroxyethoxy)ethyl]-21,23-dihydro-3H-porphyrin-2-yl]ethoxy]ethanol Chemical compound OCCOC(C)C1=C2NC(C1[2H])(C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N1)=C2)C(C)OCCO OQSAAKTZXLIZJJ-OKWSDYJOSA-N 0.000 description 1
XDRZLFPUZXUSTC-VAAKKRCDSA-N 2-[1-[3-deuterio-4-[1-(2-hydroxyethoxy)ethyl]-21-methyl-3,23-dihydroporphyrin-2-yl]ethoxy]ethanol Chemical compound OCCOC(C)C1=C2N(C(C1[2H])(C=C1C=CC(=N1)C=C1C=CC(N1)=CC=1C=CC(N=1)=C2)C(C)OCCO)C XDRZLFPUZXUSTC-VAAKKRCDSA-N 0.000 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 1
CUHRIRXNRTVEOH-UHFFFAOYSA-N 2-aminoacetic acid;chloroethane Chemical compound CCCl.NCC(O)=O CUHRIRXNRTVEOH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
241001481833 Coryphaena hippurus Species 0.000 description 1
FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 1
LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
229910052693 Europium Inorganic materials 0.000 description 1
229910052688 Gadolinium Inorganic materials 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
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Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Investigating Or Analysing Biological Materials (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

JP25323186A 1985-10-23 1986-10-23 ポルフイリン誘導体 Granted JPS62174079A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP23532285		1985-10-23
JP60-235322		1985-10-23

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP6032089A Division JPH0725763B2 (ja)	1985-10-23	1989-03-13	ポルフィリン誘導体

Publications (2)

Publication Number	Publication Date
JPS62174079A JPS62174079A (ja)	1987-07-30
JPS6313997B2 true JPS6313997B2 (de)	1988-03-29

Family

ID=16984388

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP25323186A Granted JPS62174079A (ja)	1985-10-23	1986-10-23	ポルフイリン誘導体
JP6032089A Expired - Fee Related JPH0725763B2 (ja)	1985-10-23	1989-03-13	ポルフィリン誘導体

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP6032089A Expired - Fee Related JPH0725763B2 (ja)	1985-10-23	1989-03-13	ポルフィリン誘導体

Country Status (1)

Country	Link
JP (2)	JPS62174079A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100484206B1 (ko) *	2003-01-16	2005-04-20	주식회사 테크노마트	포르피린 화합물

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0615545B2 (ja) *	1984-10-01	1994-03-02	東洋薄荷工業株式会社	金属フェオホーバイド誘導体および金属ポルフィリン誘導体
JPH0466873A (ja) *	1990-07-06	1992-03-03	Canon Inc	検体処理方法及び検体測定方法及び検体測定装置

1986
- 1986-10-23 JP JP25323186A patent/JPS62174079A/ja active Granted
1989
- 1989-03-13 JP JP6032089A patent/JPH0725763B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPH0725763B2 (ja)	1995-03-22
JPH0276881A (ja)	1990-03-16
JPS62174079A (ja)	1987-07-30

Publication	Publication Date	Title
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US5268371A (en)	1993-12-07	Derivatives of porphyrin and metalloporphyrins optionally coupled to a biologically active molecule and pharmaceutical composition containing them
US5252317A (en)	1993-10-12	Amplifier molecules for diagnosis and therapy derived from 3,5-bis[1-(3-amino-2,2-bis (aminomethyl)-propyl) oxymethyl] benzoic acid
US5135737A (en)	1992-08-04	Amplifier molecules for enhancement of diagnosis and therapy
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HK1006632B (en)	1999-03-05	Carboxamide modified polyamine chelators and radioactive complexes and conjugates
US20030100752A1 (en)	2003-05-29	Substituted porphyrin and azaporphyrin derivatives and their use in photodynamic therapy, radioimaging and MRI diagnosis
JPH08504399A (ja)	1996-05-14	３−，８−置換ジューテロポルフィリン誘導体、これを含用する薬剤及びその製法
JPH02104588A (ja)	1990-04-17	５員‐又は６員‐環を有する巨大環状ポリアザ‐化合物、その製法及びこれを含有するｎｍｒ‐、ｘ線‐、放射線‐診断用及び放射能‐及び照射線‐治療用薬剤及びこの薬剤の製法
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DE69231952T2 (de)	2002-04-04	Komplexbildnermittel und zielimmunoreagenzien
EP0350948B1 (de)	1998-03-18	Porphyrinderivate
US8133473B2 (en)	2012-03-13	Chlorin and bacteriochlorin-based difunctional aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals
JPS6313997B2 (de)	1988-03-29
JPH0424661B2 (de)	1992-04-27
JPH07330773A (ja)	1995-12-19	ポルフィリン誘導体とその用途
JP2520735B2 (ja)	1996-07-31	ポルフィリン誘導体
WO1994003593A1 (en)	1994-02-17	Amplifier molecules for enhancement of diagnosis and therapy
AU2002314857A1 (en)	2002-12-09	Substituted porphyrin and azaporphyrin derivatives and their use in photodynamic therapy, radioimaging and MRI diagnosis