JPH04502919A - キレート化剤誘導体 - Google Patents

キレート化剤誘導体

Info

Publication number: JPH04502919A
Authority: JP; Japan
Prior art keywords: group; compound; formula; chr1; metal
Prior art date: 1989-01-13
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.): Pending

Application number

JP2502948A

Other languages

English (en)

Japanese (ja)

Inventor

アルメン，トルステン

ベルグ，アルネ

クラーヴエネス，ヨー

ロングヴエード，ポール

Original Assignee

ニユコメド・アクシエセルカペト

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.)

1989-01-13

Filing date

1990-01-15

Publication date

1992-05-28

1990-01-15 Application filed by ニユコメド・アクシエセルカペト filed Critical ニユコメド・アクシエセルカペト

1992-05-28 Publication of JPH04502919A publication Critical patent/JPH04502919A/ja

Status Pending legal-status Critical Current

Links

239000002738 chelating agent Substances 0.000 title claims description 21
150000001875 compounds Chemical class 0.000 claims description 133
229910052751 metal Inorganic materials 0.000 claims description 49
239000002184 metal Substances 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 38
239000013522 chelant Substances 0.000 claims description 36
238000000034 method Methods 0.000 claims description 35
229910052757 nitrogen Inorganic materials 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
239000000032 diagnostic agent Substances 0.000 claims description 13
229940039227 diagnostic agent Drugs 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 10
150000001412 amines Chemical class 0.000 claims description 9
230000005298 paramagnetic effect Effects 0.000 claims description 9
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
229910001385 heavy metal Inorganic materials 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
229940124597 therapeutic agent Drugs 0.000 claims description 8
229910052688 Gadolinium Inorganic materials 0.000 claims description 7
150000001408 amides Chemical class 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
229910021645 metal ion Inorganic materials 0.000 claims description 7
230000002285 radioactive effect Effects 0.000 claims description 7
238000001959 radiotherapy Methods 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 6
150000002500 ions Chemical class 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
241000894007 species Species 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
238000001784 detoxification Methods 0.000 claims description 5
229910052692 Dysprosium Inorganic materials 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000000729 antidote Substances 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
238000003745 diagnosis Methods 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
238000003384 imaging method Methods 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
238000002604 ultrasonography Methods 0.000 claims description 3
229910052693 Europium Inorganic materials 0.000 claims description 2
229910052689 Holmium Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
229910052804 chromium Inorganic materials 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 15
101150113676 chr1 gene Proteins 0.000 claims 15
101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 claims 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
101100407705 Zinnia violacea POD2 gene Proteins 0.000 claims 1
238000002601 radiography Methods 0.000 claims 1
-1 1-(hydroxypropyl) (dimethyl)-2-hydroxy-ethyl Chemical group 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 8
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000002872 contrast media Substances 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
231100000419 toxicity Toxicity 0.000 description 6
230000001988 toxicity Effects 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
238000005903 acid hydrolysis reaction Methods 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
238000006268 reductive amination reaction Methods 0.000 description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
238000005576 amination reaction Methods 0.000 description 3
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
150000001923 cyclic compounds Chemical class 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000007429 general method Methods 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
239000012988 Dithioester Substances 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
101000935117 Homo sapiens Voltage-dependent P/Q-type calcium channel subunit alpha-1A Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
208000036758 Postinfectious cerebellitis Diseases 0.000 description 2
102100025330 Voltage-dependent P/Q-type calcium channel subunit alpha-1A Human genes 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000005881 detosylation reaction Methods 0.000 description 2
239000002612 dispersion medium Substances 0.000 description 2
125000005022 dithioester group Chemical group 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000022244 formylation Effects 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
229910052737 gold Inorganic materials 0.000 description 2
239000010931 gold Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000005291 magnetic effect Effects 0.000 description 2
238000002595 magnetic resonance imaging Methods 0.000 description 2
239000011572 manganese Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
229920000768 polyamine Polymers 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
150000007970 thio esters Chemical class 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
ZGCHLAJIRWDGFE-UHFFFAOYSA-N 1-aminopropane-1,1-diol Chemical compound CCC(N)(O)O ZGCHLAJIRWDGFE-UHFFFAOYSA-N 0.000 description 1
DJQBTYQUUYPCFM-UHFFFAOYSA-N 1-n-(2-amino-3-phenylmethoxypropyl)-3-phenylmethoxypropane-1,2-diamine Chemical compound C=1C=CC=CC=1COCC(N)CNCC(N)COCC1=CC=CC=C1 DJQBTYQUUYPCFM-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
108010039918 Polylysine Proteins 0.000 description 1
201000007902 Primary cutaneous amyloidosis Diseases 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
230000009471 action Effects 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001298 alcohols Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000003190 augmentative effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
238000002089 carbo-reduction Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
235000019994 cava Nutrition 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
239000011651 chromium Substances 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000000039 congener Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
238000002059 diagnostic imaging Methods 0.000 description 1
238000002405 diagnostic procedure Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229910003440 dysprosium oxide Inorganic materials 0.000 description 1
NLQFUUYNQFMIJW-UHFFFAOYSA-N dysprosium(iii) oxide Chemical compound O=[Dy]O[Dy]=O NLQFUUYNQFMIJW-UHFFFAOYSA-N 0.000 description 1
239000002961 echo contrast media Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229940075613 gadolinium oxide Drugs 0.000 description 1
229910001938 gadolinium oxide Inorganic materials 0.000 description 1
MEANOSLIBWSCIT-UHFFFAOYSA-K gadolinium trichloride Chemical compound Cl[Gd](Cl)Cl MEANOSLIBWSCIT-UHFFFAOYSA-K 0.000 description 1
CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
208000014670 posterior cortical atrophy Diseases 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
238000000513 principal component analysis Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229910052713 technetium Inorganic materials 0.000 description 1
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
238000013519 translation Methods 0.000 description 1
238000012285 ultrasound imaging Methods 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Toxicology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP2502948A 1989-01-13 1990-01-15 キレート化剤誘導体 Pending JPH04502919A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8900732,2		1989-01-13
GB898900732A GB8900732D0 (en)	1989-01-13	1989-01-13	Agents

Publications (1)

Publication Number	Publication Date
JPH04502919A true JPH04502919A (ja)	1992-05-28

Family

ID=10649976

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2502948A Pending JPH04502919A (ja)	1989-01-13	1990-01-15	キレート化剤誘導体

Country Status (5)

Country	Link
EP (1)	EP0453507A1 (de)
JP (1)	JPH04502919A (de)
AU (1)	AU5044690A (de)
GB (1)	GB8900732D0 (de)
WO (1)	WO1990008134A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9115375D0 (en) *	1991-07-17	1991-09-04	Salutar Inc	Compounds
US5562894A (en) *	1991-08-09	1996-10-08	Regents Of The University Of California	Amino-acyl-type and catecholamine-type contrast agents for MRI
US5684149A (en) *	1993-01-22	1997-11-04	Research Foundation Of State University Of New York	Metal complexes for promoting catalytic cleavage of RNA by transesterification
DE19507820A1 (de) *	1995-02-21	1996-08-22	Schering Ag	Neuartig substituierte DTPA-Derivate, deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik, sowie Verfahren zur Herstellung der Komplexe und Mittel

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB744926A (en) *	1952-06-11	1956-02-15	Dow Chemical Co	Polyhydroxyamino acid compounds
US3726912A (en) *	1970-07-02	1973-04-10	Dow Chemical Co	Substituted alkanolamine chelating agents
US4187245A (en) *	1975-06-02	1980-02-05	Petrolite Corporation	Hydroxypropylene-amino-phosphonic-sulfonic acids
DE3324235A1 (de) *	1983-07-01	1985-01-10	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue komplexbildner, komplexe und komplexsalze
GB8518300D0 (en) *	1985-07-19	1985-08-29	Amersham Int Plc	Contrast agent
AU608759B2 (en) *	1986-08-04	1991-04-18	Amersham Health Salutar Inc	NMR imaging with paramagnetic polyvalents metal salts of poly-(acid-alkylene-amido)-alkanes
JP2833766B2 (ja) *	1987-07-16	1998-12-09	ニユコメド・アクシエセルカペト	アミノポリカルボン酸およびその誘導体

1989
- 1989-01-13 GB GB898900732A patent/GB8900732D0/en active Pending
1990
- 1990-01-15 EP EP90902777A patent/EP0453507A1/de not_active Withdrawn
- 1990-01-15 WO PCT/EP1990/000078 patent/WO1990008134A1/en not_active Ceased
- 1990-01-15 JP JP2502948A patent/JPH04502919A/ja active Pending
- 1990-01-15 AU AU50446/90A patent/AU5044690A/en not_active Abandoned

Also Published As

Publication number	Publication date
EP0453507A1 (de)	1991-10-30
AU5044690A (en)	1990-08-13
WO1990008134A1 (en)	1990-07-26
GB8900732D0 (en)	1989-03-08

Publication	Publication Date	Title
EP0299795B1 (de)	1992-03-18	Aminopolycarbonsäure und ihre Derivate
JP3131219B2 (ja)	2001-01-31	キレート化合物
EP0452392B1 (de)	1995-04-12	Heterocyclische chelatbildende wirkstoffe
JP2773870B2 (ja)	1998-07-09	マンガンキレート（▲ｉｉ▼）ｎｍｒｉ造影剤
EP0717639B1 (de)	2003-04-02	Phosphonate- und nicht-phosphonate einheiten enthaltende polyamino-paramagnetische-chelate fuer anwendung in mri
US7385041B2 (en)	2008-06-10	Dual functioning excipient for metal chelate contrast agents
CA2039399C (en)	2000-09-05	Dual functioning excipient for metal chelate contrast agents
JPH06504301A (ja)	1994-05-19	キレート化剤
JPH04502919A (ja)	1992-05-28	キレート化剤誘導体
CA2098712A1 (en)	1992-06-22	Chelating agents
CA1230342A (en)	1987-12-15	Tc99m-phenida, radioscintigraphic agent for diagnosis of hepatobiliary disease
WO1991015467A1 (en)	1991-10-17	Aminopolycarboxylic acid chelating agents
AU646795C (en)	1995-03-02	Heterocyclic chelating agents
AU644627B2 (en)	1993-12-16	Chelating compounds
IE911182A1 (en)	1991-10-09	Chelating agents
IE922636L (en)	1988-02-04	Use of chelate complexes
HK1003572B (en)	1998-10-30	Aminocarboxylic acids and derivatives thereof