BE883304A - Complexes d'acide phtalocyanine tetrasulfonique et d'isotopes de metaux emettant des radiations gamma de courte duree de vie et leurs applications comme agents de diagnostic - Google Patents

Complexes d'acide phtalocyanine tetrasulfonique et d'isotopes de metaux emettant des radiations gamma de courte duree de vie et leurs applications comme agents de diagnostic Download PDF

Info

Publication number: BE883304A
Authority: BE; Belgium
Prior art keywords: emi; phthalocyanine; acid; tumor; gallium
Prior art date: 1979-05-18

Application number

BE0/200620A

Other languages

English (en)

French (fr)

Inventor

J Lier

D Autenrieth

J Rousseau

Original Assignee

Univ Sherbrooke

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.)

1979-05-18

Filing date

1980-05-14

Publication date

1980-11-14

1980-05-14 Application filed by Univ Sherbrooke filed Critical Univ Sherbrooke

1980-11-14 Publication of BE883304A publication Critical patent/BE883304A/fr

Links

IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title claims description 17
239000002253 acid Substances 0.000 title claims description 7
229940039227 diagnostic agent Drugs 0.000 title claims 3
239000000032 diagnostic agent Substances 0.000 title claims 3
206010028980 Neoplasm Diseases 0.000 claims description 26
229910052751 metal Inorganic materials 0.000 claims description 21
239000002184 metal Substances 0.000 claims description 21
241001465754 Metazoa Species 0.000 claims description 19
238000000034 method Methods 0.000 claims description 19
NUSQOFAKCBLANB-UHFFFAOYSA-N phthalocyanine tetrasulfonic acid Chemical compound C12=CC(S(=O)(=O)O)=CC=C2C(N=C2NC(C3=CC=C(C=C32)S(O)(=O)=O)=N2)=NC1=NC([C]1C=CC(=CC1=1)S(O)(=O)=O)=NC=1N=C1[C]3C=CC(S(O)(=O)=O)=CC3=C2N1 NUSQOFAKCBLANB-UHFFFAOYSA-N 0.000 claims description 19
230000002285 radioactive effect Effects 0.000 claims description 19
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 16
229910052733 gallium Inorganic materials 0.000 claims description 16
238000001514 detection method Methods 0.000 claims description 10
239000000203 mixture Substances 0.000 claims description 9
229910052738 indium Inorganic materials 0.000 claims description 8
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 8
230000005855 radiation Effects 0.000 claims description 8
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
229910052804 chromium Inorganic materials 0.000 claims description 6
239000011651 chromium Substances 0.000 claims description 6
229910017052 cobalt Inorganic materials 0.000 claims description 6
239000010941 cobalt Substances 0.000 claims description 6
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 6
229910052753 mercury Inorganic materials 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
229910052713 technetium Inorganic materials 0.000 claims description 5
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
230000000694 effects Effects 0.000 description 15
210000000056 organ Anatomy 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
150000002739 metals Chemical class 0.000 description 8
210000003734 kidney Anatomy 0.000 description 7
210000004185 liver Anatomy 0.000 description 6
239000000825 pharmaceutical preparation Substances 0.000 description 6
229940127557 pharmaceutical product Drugs 0.000 description 6
239000008280 blood Substances 0.000 description 5
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201000011510 cancer Diseases 0.000 description 5
238000009826 distribution Methods 0.000 description 5
239000003814 drug Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
230000006870 function Effects 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
210000004072 lung Anatomy 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
210000000952 spleen Anatomy 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000295 emission spectrum Methods 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
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210000003205 muscle Anatomy 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
210000001685 thyroid gland Anatomy 0.000 description 3
210000003462 vein Anatomy 0.000 description 3
238000012800 visualization Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
SDGNNLQZAPXALR-UHFFFAOYSA-N 3-sulfophthalic acid Chemical compound OC(=O)C1=CC=CC(S(O)(=O)=O)=C1C(O)=O SDGNNLQZAPXALR-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
206010027476 Metastases Diseases 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
230000018109 developmental process Effects 0.000 description 2
238000013399 early diagnosis Methods 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
210000000232 gallbladder Anatomy 0.000 description 2
210000002216 heart Anatomy 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000002427 irreversible effect Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
229910021645 metal ion Inorganic materials 0.000 description 2
238000011160 research Methods 0.000 description 2
210000003079 salivary gland Anatomy 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
-1 sulfonated uranyl phthalocyanine Chemical compound 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
210000000689 upper leg Anatomy 0.000 description 2
230000002792 vascular Effects 0.000 description 2
WLXYHLHNIRJAIG-UHFFFAOYSA-N 2h-benzo[e]isoindole Chemical compound C1=CC=C2C3=CNC=C3C=CC2=C1 WLXYHLHNIRJAIG-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
206010003445 Ascites Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
208000003174 Brain Neoplasms Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
210000003484 anatomy Anatomy 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000000211 autoradiogram Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
201000008274 breast adenocarcinoma Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000013626 chemical specie Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
238000002405 diagnostic procedure Methods 0.000 description 1
238000012631 diagnostic technique Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000011790 ferrous sulphate Substances 0.000 description 1
235000003891 ferrous sulphate Nutrition 0.000 description 1
238000001914 filtration Methods 0.000 description 1
UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000004698 iron complex Chemical class 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
230000003907 kidney function Effects 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
210000002414 leg Anatomy 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000003908 liver function Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
210000000865 mononuclear phagocyte system Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
150000004032 porphyrins Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000005258 radioactive decay Effects 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000005748 tumor development Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0485—Porphyrins, texaphyrins wherein the nitrogen atoms forming the central ring system complex the radioactive metal
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Optics & Photonics (AREA)
Pharmacology & Pharmacy (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Physics & Mathematics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Investigating Or Analysing Biological Materials (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

BE0/200620A 1979-05-18 1980-05-14 Complexes d'acide phtalocyanine tetrasulfonique et d'isotopes de metaux emettant des radiations gamma de courte duree de vie et leurs applications comme agents de diagnostic BE883304A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4018179A	1979-05-18	1979-05-18

Publications (1)

Publication Number	Publication Date
BE883304A true BE883304A (fr)	1980-11-14

Family

ID=21909580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/200620A BE883304A (fr)	1979-05-18	1980-05-14	Complexes d'acide phtalocyanine tetrasulfonique et d'isotopes de metaux emettant des radiations gamma de courte duree de vie et leurs applications comme agents de diagnostic

Country Status (2)

Country	Link
JP (1)	JPS565417A (ja)
BE (1)	BE883304A (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6169811A (ja) *	1984-09-12	1986-04-10	Mitsubishi Chem Ind Ltd	安定剤を含有する高分子量３メチルブテン−１重合体
JPS61113631A (ja) *	1984-11-07	1986-05-31	Adeka Argus Chem Co Ltd	ポリオレフイン樹脂組成物
IT1215943B (it) *	1988-02-24	1990-02-22	Enichem Sintesi	Composizione stabilizzante per polimeri organici.

1980
- 1980-05-14 BE BE0/200620A patent/BE883304A/fr unknown
- 1980-05-16 JP JP6414680A patent/JPS565417A/ja active Pending

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Publication number	Publication date
JPS565417A (en)	1981-01-20

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