JPH09512796A - 治療用の放射性製薬のための二官能性キレート剤の調製に使用するチオエーテル化合物 - Google Patents
治療用の放射性製薬のための二官能性キレート剤の調製に使用するチオエーテル化合物Info
- Publication number
- JPH09512796A JPH09512796A JP7528329A JP52832995A JPH09512796A JP H09512796 A JPH09512796 A JP H09512796A JP 7528329 A JP7528329 A JP 7528329A JP 52832995 A JP52832995 A JP 52832995A JP H09512796 A JPH09512796 A JP H09512796A
- Authority
- JP
- Japan
- Prior art keywords
- ligand
- group
- compound according
- complex
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 229940127044 therapeutic radiopharmaceutical Drugs 0.000 title claims description 7
- 150000003568 thioethers Chemical class 0.000 title description 15
- 239000002738 chelating agent Substances 0.000 title description 5
- 230000001588 bifunctional effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000000101 thioether group Chemical group 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims abstract description 10
- 239000003446 ligand Substances 0.000 claims description 78
- 239000013522 chelant Substances 0.000 claims description 31
- 125000004429 atom Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 230000027455 binding Effects 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 238000001727 in vivo Methods 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000008685 targeting Effects 0.000 claims description 6
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 claims description 4
- 102000008394 Immunoglobulin Fragments Human genes 0.000 claims description 3
- 108010021625 Immunoglobulin Fragments Proteins 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 claims description 2
- 102000014187 peptide receptors Human genes 0.000 claims description 2
- 108010011903 peptide receptors Proteins 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000007142 ring opening reaction Methods 0.000 claims 1
- 229940121896 radiopharmaceutical Drugs 0.000 abstract description 6
- 239000012217 radiopharmaceutical Substances 0.000 abstract description 6
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 230000000536 complexating effect Effects 0.000 abstract description 2
- 239000010948 rhodium Substances 0.000 description 51
- 150000002009 diols Chemical class 0.000 description 17
- 239000003814 drug Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000009918 complex formation Effects 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- 230000002285 radioactive effect Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000001962 electrophoresis Methods 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 230000002799 radiopharmaceutical effect Effects 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- 230000003439 radiotherapeutic effect Effects 0.000 description 4
- 230000000975 bioactive effect Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000004807 localization Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229960003330 pentetic acid Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- -1 thioether macrocycles Chemical class 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LIVCAIOLNUODDU-UHFFFAOYSA-N 1,5,9,13-tetrathiacyclohexadecane Chemical compound C1CSCCCSCCCSCCCSC1 LIVCAIOLNUODDU-UHFFFAOYSA-N 0.000 description 1
- UKLHHIPXESCOQU-UHFFFAOYSA-N 1,5,9,13-tetrathiacyclohexadecane-3,11-diol Chemical compound OC1CSCCCSCC(O)CSCCCSC1 UKLHHIPXESCOQU-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 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
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D341/00—Heterocyclic compounds containing rings having three or more sulfur atoms as the only ring hetero 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23635394A | 1994-04-29 | 1994-04-29 | |
| US08/236,353 | 1994-04-29 | ||
| PCT/US1995/005045 WO1995029925A1 (en) | 1994-04-29 | 1995-04-25 | Thioether compounds for use in preparing bifunctional chelating agents for therapeutic radiopharmaceuticals |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09512796A true JPH09512796A (ja) | 1997-12-22 |
Family
ID=22889149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7528329A Pending JPH09512796A (ja) | 1994-04-29 | 1995-04-25 | 治療用の放射性製薬のための二官能性キレート剤の調製に使用するチオエーテル化合物 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0757694A4 (de) |
| JP (1) | JPH09512796A (de) |
| AU (1) | AU2363495A (de) |
| CA (1) | CA2188565A1 (de) |
| WO (1) | WO1995029925A1 (de) |
| ZA (1) | ZA953448B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016518447A (ja) * | 2013-05-13 | 2016-06-23 | ビジョン グローバル ホールディングス リミテッドＶｉｓｉｏｎ Ｇｌｏｂａｌ Ｈｏｌｄｉｎｇｓ Ｌｔｄ． | がん治療および診断イメージングのための修飾ヘモグロビンベース系治療剤を含む医薬組成物 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4480245B2 (ja) * | 2000-03-13 | 2010-06-16 | 株式会社コスモ総合研究所 | 環状アニリン硫化物とその製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175343A (en) * | 1985-01-14 | 1992-12-29 | Neorx Corporation | Metal radionuclide labeled proteins for diagnosis and therapy |
| US4994560A (en) * | 1987-06-24 | 1991-02-19 | The Dow Chemical Company | Functionalized polyamine chelants and radioactive rhodium complexes thereof for conjugation to antibodies |
| US4782013A (en) * | 1987-07-23 | 1988-11-01 | Eastman Kodak Company | Photographic element containing a macrocyclic ether compound |
| GB9007039D0 (en) * | 1990-03-29 | 1990-05-30 | Isis Innovation | Complexes of thioethers |
| FR2662159B1 (fr) * | 1990-05-15 | 1994-03-11 | Matieres Nucleaires Cie Gle | Nouveaux ligands thio-ethers et leur utilisation pour separer le palladium de solutions aqueuses, en particulier de soludtions nitriques de dissolution d'elements combustibles nucleaires irradies. |
-
1995
- 1995-04-25 AU AU23634/95A patent/AU2363495A/en not_active Abandoned
- 1995-04-25 EP EP95917659A patent/EP0757694A4/de not_active Withdrawn
- 1995-04-25 JP JP7528329A patent/JPH09512796A/ja active Pending
- 1995-04-25 WO PCT/US1995/005045 patent/WO1995029925A1/en not_active Application Discontinuation
- 1995-04-25 CA CA002188565A patent/CA2188565A1/en not_active Abandoned
- 1995-04-28 ZA ZA953448A patent/ZA953448B/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016518447A (ja) * | 2013-05-13 | 2016-06-23 | ビジョン グローバル ホールディングス リミテッドＶｉｓｉｏｎ Ｇｌｏｂａｌ Ｈｏｌｄｉｎｇｓ Ｌｔｄ． | がん治療および診断イメージングのための修飾ヘモグロビンベース系治療剤を含む医薬組成物 |
| US10322180B2 (en) | 2013-05-13 | 2019-06-18 | Vision Global Holdings Ltd. | Pharmaceutical composition comprising modified hemoglobin-based therapeutic agent for cancer targeting treatment and diagnostic imaging |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2363495A (en) | 1995-11-29 |
| CA2188565A1 (en) | 1995-11-09 |
| EP0757694A4 (de) | 1998-05-06 |
| EP0757694A1 (de) | 1997-02-12 |
| WO1995029925A1 (en) | 1995-11-09 |
| ZA953448B (en) | 1996-01-12 |
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