JPH10502648A - テクネチウム−スルホンアミド−錯体、これらの利用、これらを含有する医薬、並びに錯体及び薬剤を製造する方法 - Google Patents
テクネチウム−スルホンアミド−錯体、これらの利用、これらを含有する医薬、並びに錯体及び薬剤を製造する方法Info
- Publication number
- JPH10502648A JPH10502648A JP8504625A JP50462596A JPH10502648A JP H10502648 A JPH10502648 A JP H10502648A JP 8504625 A JP8504625 A JP 8504625A JP 50462596 A JP50462596 A JP 50462596A JP H10502648 A JPH10502648 A JP H10502648A
- Authority
- JP
- Japan
- Prior art keywords
- residue
- group
- hydrogen
- nitrogen
- carbon
- 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
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- 239000002184 metal Substances 0.000 claims abstract description 20
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 13
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- 238000001959 radiotherapy Methods 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 254
- 229910052739 hydrogen Inorganic materials 0.000 claims description 254
- 229910052717 sulfur Inorganic materials 0.000 claims description 213
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 211
- 239000011593 sulfur Substances 0.000 claims description 211
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- 239000001301 oxygen Substances 0.000 claims description 68
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- 239000000460 chlorine Substances 0.000 claims description 62
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical group OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 125000002345 steroid group Chemical group 0.000 claims 2
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
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- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 239000002773 nucleotide Substances 0.000 claims 1
- 125000003729 nucleotide group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 18
- 239000002738 chelating agent Substances 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 4
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- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 460
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 254
- 150000002431 hydrogen Chemical class 0.000 description 245
- 229910052799 carbon Inorganic materials 0.000 description 244
- 229910052757 nitrogen Inorganic materials 0.000 description 235
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 231
- 239000000243 solution Substances 0.000 description 158
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 69
- 238000003756 stirring Methods 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000000284 extract Substances 0.000 description 43
- 239000000741 silica gel Substances 0.000 description 42
- 229910002027 silica gel Inorganic materials 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
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- 239000007787 solid Substances 0.000 description 32
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- 238000010992 reflux Methods 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- 150000001408 amides Chemical class 0.000 description 25
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- 238000004587 chromatography analysis Methods 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
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- 229910052763 palladium Inorganic materials 0.000 description 15
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- 238000001035 drying Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
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- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 3
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- 101100208721 Mus musculus Usp5 gene Proteins 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/28—Isothiocyanates having isothiocyanate groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K51/0478—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 complexes from non-cyclic ligands, e.g. EDTA, MAG3
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- A—HUMAN NECESSITIES
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- 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
- A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
- A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
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- 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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2121/00—Preparations for use in therapy
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (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 |
|---|---|---|---|
| DE4425781A DE4425781A1 (de) | 1994-07-14 | 1994-07-14 | Technetium-Sulfonamid-Komplexe, deren Verwendung, diese enthaltende pharmazeutische Mittel, sowie Verfahren zur Herstellung der Komplexe und Mittel |
| DE4425781.3 | 1994-07-14 | ||
| PCT/EP1995/002404 WO1996002500A1 (de) | 1994-07-14 | 1995-06-22 | Technetium-sulfonamid-komplexe, deren verwendung, diese enthaltende pharmazeutische mittel, sowie verfahren zur herstellung der komplexe und mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH10502648A true JPH10502648A (ja) | 1998-03-10 |
Family
ID=6523740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8504625A Pending JPH10502648A (ja) | 1994-07-14 | 1995-06-22 | テクネチウム−スルホンアミド−錯体、これらの利用、これらを含有する医薬、並びに錯体及び薬剤を製造する方法 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0770063A1 (hu) |
| JP (1) | JPH10502648A (hu) |
| KR (1) | KR970704682A (hu) |
| CN (1) | CN1152914A (hu) |
| AU (1) | AU698824B2 (hu) |
| CA (1) | CA2194561A1 (hu) |
| DE (1) | DE4425781A1 (hu) |
| HU (1) | HUT76806A (hu) |
| NO (1) | NO970140L (hu) |
| WO (1) | WO1996002500A1 (hu) |
| ZA (1) | ZA955896B (hu) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006501149A (ja) * | 2002-05-06 | 2006-01-12 | エンドサイト，インコーポレイテッド | ビタミンを標的とした造影剤 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5028422A (en) * | 1986-05-27 | 1991-07-02 | Schering Corporation | Treatment of basal cell carcinoma intralesionally with recombinant human alpha interferon |
| JP2004502754A (ja) * | 2000-07-06 | 2004-01-29 | アレー バイオファーマ インコーポレイテッド | ホスファターゼ阻害剤の調製 |
| KR100445971B1 (ko) * | 2002-04-15 | 2004-08-25 | 한국원자력연구소 | 수소화붕소 교환수지를 이용한 테크네튬 또는 레늄의표지방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4980147A (en) * | 1984-06-25 | 1990-12-25 | University Of Utah Research Foundation | Radiolabeled technetium chelates for use in renal function determinations |
| ES2017088B3 (es) * | 1986-05-28 | 1991-01-01 | Mallinckrodt Inc (A Missouri Corporation) | Quelatos de tecnecio a utilizar para determinar la funcion renal. |
-
1994
- 1994-07-14 DE DE4425781A patent/DE4425781A1/de not_active Withdrawn
-
1995
- 1995-06-22 WO PCT/EP1995/002404 patent/WO1996002500A1/de not_active Application Discontinuation
- 1995-06-22 CN CN95194028A patent/CN1152914A/zh active Pending
- 1995-06-22 CA CA002194561A patent/CA2194561A1/en not_active Abandoned
- 1995-06-22 KR KR1019970700193A patent/KR970704682A/ko not_active Application Discontinuation
- 1995-06-22 JP JP8504625A patent/JPH10502648A/ja active Pending
- 1995-06-22 EP EP95924304A patent/EP0770063A1/de not_active Withdrawn
- 1995-06-22 AU AU28865/95A patent/AU698824B2/en not_active Ceased
- 1995-06-22 HU HU9700101A patent/HUT76806A/hu unknown
- 1995-07-14 ZA ZA955896A patent/ZA955896B/xx unknown
-
1997
- 1997-01-13 NO NO970140A patent/NO970140L/no unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006501149A (ja) * | 2002-05-06 | 2006-01-12 | エンドサイト，インコーポレイテッド | ビタミンを標的とした造影剤 |
| JP2011012066A (ja) * | 2002-05-06 | 2011-01-20 | Endocyte Inc | ビタミンを標的とした造影剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR970704682A (ko) | 1997-09-06 |
| AU698824B2 (en) | 1998-11-05 |
| HUT76806A (en) | 1997-11-28 |
| CN1152914A (zh) | 1997-06-25 |
| ZA955896B (en) | 1996-02-19 |
| AU2886595A (en) | 1996-02-16 |
| DE4425781A1 (de) | 1996-01-18 |
| EP0770063A1 (de) | 1997-05-02 |
| NO970140L (no) | 1997-03-13 |
| NO970140D0 (no) | 1997-01-13 |
| CA2194561A1 (en) | 1996-02-01 |
| WO1996002500A1 (de) | 1996-02-01 |
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