CA1096399A - Acide iminodiacetique a usage pharcacologique - Google Patents

Acide iminodiacetique a usage pharcacologique

Info

Publication number: CA1096399A
Authority: CA; Canada
Prior art keywords: chelate; iminodiacetic acid; technetium; solution; acid
Prior art date: 1975-09-02
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

CA335,980A

Other languages

English (en)

Inventor

Michael D. Loberg

Patrick S. Callery

Malcolm Cooper

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.)

Research Corp

Original Assignee

Research Corp

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.)

1975-09-02

Filing date

1979-09-20

Publication date

1981-02-24

1975-09-02 Priority claimed from US05/609,545 external-priority patent/US4017596A/en

1975-12-31 Priority claimed from CA242,855A external-priority patent/CA1070695A/fr

1979-09-20 Application filed by Research Corp filed Critical Research Corp

1979-09-20 Priority to CA335,980A priority Critical patent/CA1096399A/fr

1981-02-24 Application granted granted Critical

1981-02-24 Publication of CA1096399A publication Critical patent/CA1096399A/fr

Status Expired legal-status Critical Current

Links

NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 title claims abstract description 9
238000000034 method Methods 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
239000013522 chelant Substances 0.000 abstract description 26
GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 abstract description 18
229940056501 technetium 99m Drugs 0.000 abstract description 18
239000002738 chelating agent Substances 0.000 abstract description 8
230000002799 radiopharmaceutical effect Effects 0.000 abstract description 5
239000005725 8-Hydroxyquinoline Chemical class 0.000 abstract description 4
GYHNNYVSQQEPJS-OIOBTWANSA-N Gallium-67 Chemical compound [67Ga] GYHNNYVSQQEPJS-OIOBTWANSA-N 0.000 abstract description 4
GUTLYIVDDKVIGB-YPZZEJLDSA-N cobalt-57 Chemical compound [57Co] GUTLYIVDDKVIGB-YPZZEJLDSA-N 0.000 abstract description 4
229940006110 gallium-67 Drugs 0.000 abstract description 4
229960003540 oxyquinoline Drugs 0.000 abstract description 4
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract description 4
239000012217 radiopharmaceutical Substances 0.000 abstract description 4
229940121896 radiopharmaceutical Drugs 0.000 abstract description 4
DJQJFMSHHYAZJD-UHFFFAOYSA-N lidofenin Chemical compound CC1=CC=CC(C)=C1NC(=O)CN(CC(O)=O)CC(O)=O DJQJFMSHHYAZJD-UHFFFAOYSA-N 0.000 abstract description 3
238000002360 preparation method Methods 0.000 abstract description 3
GYHNNYVSQQEPJS-YPZZEJLDSA-N Gallium-68 Chemical compound [68Ga] GYHNNYVSQQEPJS-YPZZEJLDSA-N 0.000 abstract description 2
239000012216 imaging agent Substances 0.000 abstract description 2
229940055742 indium-111 Drugs 0.000 abstract 1
APFVFJFRJDLVQX-AHCXROLUSA-N indium-111 Chemical compound [111In] APFVFJFRJDLVQX-AHCXROLUSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 20
239000000047 product Substances 0.000 description 17
210000000056 organ Anatomy 0.000 description 15
238000003384 imaging method Methods 0.000 description 11
210000004185 liver Anatomy 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241000699670 Mus sp. Species 0.000 description 7
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 6
229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
239000001119 stannous chloride Substances 0.000 description 6
235000011150 stannous chloride Nutrition 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000008280 blood Substances 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
230000000694 effects Effects 0.000 description 5
210000000936 intestine Anatomy 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229910008066 SnC12 Inorganic materials 0.000 description 4
239000003124 biologic agent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 description 3
210000000232 gallbladder Anatomy 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
DPAZYVOAYDIQBT-UHFFFAOYSA-N 11-[bis(carboxymethyl)amino]undecanoic acid Chemical compound OC(=O)CCCCCCCCCCN(CC(O)=O)CC(O)=O DPAZYVOAYDIQBT-UHFFFAOYSA-N 0.000 description 2
IYRMVVRWPNKMAY-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC1=CC=CC=C1Br IYRMVVRWPNKMAY-UHFFFAOYSA-N 0.000 description 2
XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 2
150000004325 8-hydroxyquinolines Chemical class 0.000 description 2
FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 2
102100025841 Cholecystokinin Human genes 0.000 description 2
101800001982 Cholecystokinin Proteins 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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 2
ZOKXTWBITQBERF-AKLPVKDBSA-N Molybdenum Mo-99 Chemical compound [99Mo] ZOKXTWBITQBERF-AKLPVKDBSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229940107137 cholecystokinin Drugs 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000005755 formation reaction Methods 0.000 description 2
-1 hydroxy, carboxy, nitro, amino Chemical group 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000002372 labelling Methods 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
229950009740 molybdenum mo-99 Drugs 0.000 description 2
238000012633 nuclear imaging Methods 0.000 description 2
230000005855 radiation Effects 0.000 description 2
IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
210000000813 small intestine Anatomy 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
GEZAUFNYMZVOFV-UHFFFAOYSA-J 2-[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphastannetan-2-yl)oxy]-1,3,2$l^{5},4$l^{2}-dioxaphosphastannetane 2-oxide Chemical compound [Sn+2].[Sn+2].[O-]P([O-])(=O)OP([O-])([O-])=O GEZAUFNYMZVOFV-UHFFFAOYSA-J 0.000 description 1
CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 1
XSIHGZKXMYHVCR-UHFFFAOYSA-N 2-[carboxymethyl-(2-hydroxy-3-naphthalen-1-yloxypropyl)amino]acetic acid Chemical compound C1=CC=C2C(OCC(O)CN(CC(O)=O)CC(O)=O)=CC=CC2=C1 XSIHGZKXMYHVCR-UHFFFAOYSA-N 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N Dipicolinic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
210000003484 anatomy Anatomy 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
208000027119 bilirubin metabolic disease Diseases 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
229940039227 diagnostic agent Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
208000036796 hyperbilirubinemia Diseases 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
PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
UXZFQZANDVDGMM-UHFFFAOYSA-N iodoquinol Chemical compound C1=CN=C2C(O)=C(I)C=C(I)C2=C1 UXZFQZANDVDGMM-UHFFFAOYSA-N 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000004807 localization Effects 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 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
150000002894 organic compounds Chemical class 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

CA335,980A 1975-09-02 1979-09-20 Acide iminodiacetique a usage pharcacologique Expired CA1096399A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA335,980A CA1096399A (fr)	1975-09-02	1979-09-20	Acide iminodiacetique a usage pharcacologique

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US609,545		1975-09-02
US05/609,545 US4017596A (en)	1975-03-03	1975-09-02	Radiopharmaceutical chelates and method of external imaging
CA242,855A CA1070695A (fr)	1975-09-02	1975-12-31	Produit pharmaceutique a base d'acide iminodiacetique
CA335,980A CA1096399A (fr)	1975-09-02	1979-09-20	Acide iminodiacetique a usage pharcacologique

Publications (1)

Publication Number	Publication Date
CA1096399A true CA1096399A (fr)	1981-02-24

Family

ID=27164260

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA335,980A Expired CA1096399A (fr)	1975-09-02	1979-09-20	Acide iminodiacetique a usage pharcacologique

Country Status (1)

Country	Link
CA (1)	CA1096399A (fr)

1979
- 1979-09-20 CA CA335,980A patent/CA1096399A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-02-24	MKEX	Expiry

Publication	Publication Date	Title
US4017596A (en)	1977-04-12	Radiopharmaceutical chelates and method of external imaging
JP7219497B2 (ja)	2023-02-08	Ｐｓｍａ結合剤及びその使用
CA1273950A (fr)	1990-09-11	Acides gras utilises comme agents de radiodiagnostic marques au technetium derives de ligands bisamide-bisthiol
US4673562A (en)	1987-06-16	Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents
DE69317771T2 (de)	1998-07-30	Carboxamid-modifizierte polyamin-chelatoren, radioaktive komplexe und konjugate
DK175089B1 (da)	2004-05-24	Estersubstituerede diamindithioler eller farmaceutisek egnede salte deraf, især i steril, farmaceutisk acceptabel form, samt deres anvendelse i forbindelse med radionuclidkomplekser
US4897254A (en)	1990-01-30	Radioactive compositions for the treatment of calcific tumors
CA1070695A (fr)	1980-01-29	Produit pharmaceutique a base d'acide iminodiacetique
EP0426759B1 (fr)	1993-05-19	NOUVEAUX COMPLEXES Tc-99m
JPH03291260A (ja)	1991-12-20	多官能性金属キレート化合物とその用途
Rousseau et al.	1985	Synthesis, tissue distribution and tumor uptake of 99mTc-and 67Ga-tetrasulfophthalocyanine
KR100745445B1 (ko)	2007-08-03	종양 영상화 화합물
US5955053A (en)	1999-09-21	Metal chelates as pharmaceutical imaging agents, processes of making such and uses thereof
US5986074A (en)	1999-11-16	Metal chelates as pharmaceutical imaging agents, processes of making such and uses thereof
Murugesan et al.	2001	A technetium-99m-labelled cyclam acid porphyrin (CAP) for tumour imaging
USRE31463E (en)	1983-12-13	Radiopharmaceutical chelates and method of external imaging
US4418208A (en)	1983-11-29	N-Substituted iminodiacetic acids
Chervu et al.	1984	Technetium-99m-labeled p-aminohippuric acid analog: a new renal agent: concise communication
CN100475272C (zh)	2009-04-08	放射药物的稳定剂
CA1096399A (fr)	1981-02-24	Acide iminodiacetique a usage pharcacologique
EP0107452B1 (fr)	1987-02-04	Agent de scintigraphie
US4318898A (en)	1982-03-09	Technetium-99m-labelled (2,4,5-trimethylacetanilido)-iminodiacetate for liver function diagnosis, chloroacetric acid (2,4,5-trimethylanilide), (2,4,5-trimethylacetanilido)-iminodiacetate, and process for their preparation
US4193979A (en)	1980-03-18	Sodium 3-[[[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl]-amino]carbonyl]-2-pyridinecarboxylic acid and related compounds labeled with technetium-99m
US4350674A (en)	1982-09-21	Substituted acetanilidoiminodiacetic acid compounds, diagnostic agents containing such compounds labeled with technetium-99m, and methods for making and using such compounds and agents
CA2406852A1 (fr)	2001-11-01	Complexes radiometalliques de 2-pyrrolylthiones et leur utilisation comme agents radiopharmaceutiques d'imagerie et de therapie