ZA200106750B - Regioselective synthesis of DTPA derivatives. - Google Patents

Regioselective synthesis of DTPA derivatives. Download PDF

Info

Publication number: ZA200106750B
Authority: ZA; South Africa
Prior art keywords: dtpa; tert; derivative; mono; reducing
Prior art date: 1999-03-03

Application number

ZA200106750A

Other languages

English (en)

Inventor

Paul Chinn

Michael J Labarre

Thomas Ryskamp

Albert Gyorkos

Steve Ruhl

Original Assignee

Idec Pharma 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.)

1999-03-03

Filing date

2001-08-15

Publication date

2002-11-15

2001-08-15 Application filed by Idec Pharma Corp filed Critical Idec Pharma Corp

2002-11-15 Publication of ZA200106750B publication Critical patent/ZA200106750B/en

Links

QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical class OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 title claims abstract description 61
230000015572 biosynthetic process Effects 0.000 title claims abstract description 56
238000003786 synthesis reaction Methods 0.000 title claims abstract description 54
238000000034 method Methods 0.000 claims abstract description 107
230000008569 process Effects 0.000 claims abstract description 96
FZDFGHZZPBUTGP-UHFFFAOYSA-N 2-[[2-[bis(carboxymethyl)amino]-3-(4-isothiocyanatophenyl)propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C(C)CN(CC(O)=O)CC(N(CC(O)=O)CC(O)=O)CC1=CC=C(N=C=S)C=C1 FZDFGHZZPBUTGP-UHFFFAOYSA-N 0.000 claims description 62
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
150000004985 diamines Chemical class 0.000 claims description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 30
230000008878 coupling Effects 0.000 claims description 29
238000010168 coupling process Methods 0.000 claims description 29
238000005859 coupling reaction Methods 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 27
150000001412 amines Chemical class 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
230000002194 synthesizing effect Effects 0.000 claims description 18
238000003756 stirring Methods 0.000 claims description 17
239000002904 solvent Substances 0.000 claims description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 15
239000002738 chelating agent Substances 0.000 claims description 14
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
108060003951 Immunoglobulin Proteins 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
-1 boc groups Chemical group 0.000 claims description 12
102000018358 immunoglobulin Human genes 0.000 claims description 12
229940072221 immunoglobulins Drugs 0.000 claims description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 11
239000002184 metal Substances 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
238000005804 alkylation reaction Methods 0.000 claims description 10
125000006242 amine protecting group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000000741 silica gel Substances 0.000 claims description 10
229910002027 silica gel Inorganic materials 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 8
238000004440 column chromatography Methods 0.000 claims description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 7
239000007868 Raney catalyst Substances 0.000 claims description 7
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 7
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RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 claims description 7
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
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229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 claims description 5
WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 claims description 5
TZPDNVGERDIJNX-UHFFFAOYSA-N 1-n-(2-aminopropyl)-3-(4-nitrophenyl)propane-1,2-diamine;trihydrochloride Chemical compound Cl.Cl.Cl.CC(N)CNCC(N)CC1=CC=C([N+]([O-])=O)C=C1 TZPDNVGERDIJNX-UHFFFAOYSA-N 0.000 claims description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
239000000908 ammonium hydroxide Substances 0.000 claims description 4
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 4
ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 4
150000002739 metals Chemical class 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
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HYAYWIFTYXRFCV-LYNSQETBSA-N (2s)-2-amino-n-(2-aminopropyl)-3-(4-nitrophenyl)propanamide Chemical compound CC(N)CNC(=O)[C@@H](N)CC1=CC=C([N+]([O-])=O)C=C1 HYAYWIFTYXRFCV-LYNSQETBSA-N 0.000 claims description 3
SCNVDVQATDSWMY-UHFFFAOYSA-N 2-[[2-[bis(carboxymethyl)amino]-3-(4-nitrophenyl)propyl]-[2-[bis(carboxymethyl)amino]propyl]amino]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)CN(CC(O)=O)C(C)CN(CC(O)=O)CC(N(CC(O)=O)CC(O)=O)CC1=CC=C([N+]([O-])=O)C=C1 SCNVDVQATDSWMY-UHFFFAOYSA-N 0.000 claims description 3
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230000002152 alkylating effect Effects 0.000 claims description 3
239000012455 biphasic mixture Substances 0.000 claims description 3
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims description 3
OCAAXAMLWRDBSJ-UHFFFAOYSA-N bromo 3,3-dimethylbutanoate Chemical compound CC(C)(C)CC(=O)OBr OCAAXAMLWRDBSJ-UHFFFAOYSA-N 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
239000012047 saturated solution Substances 0.000 claims description 3
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ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
JXJRGHAEUQSQAF-UHFFFAOYSA-N tert-butyl 2-[[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-3-(4-nitrophenyl)propyl]-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]propyl]amino]acetate Chemical compound CC(C)(C)OC(=O)CN(CC(=O)OC(C)(C)C)C(C)CN(CC(=O)OC(C)(C)C)CC(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)CC1=CC=C([N+]([O-])=O)C=C1 JXJRGHAEUQSQAF-UHFFFAOYSA-N 0.000 claims description 2
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229960003330 pentetic acid Drugs 0.000 description 17
239000000047 product Substances 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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WJGQCCPNVRCAQI-UHFFFAOYSA-N 1-cyanoethylazanium;chloride Chemical compound Cl.CC(N)C#N WJGQCCPNVRCAQI-UHFFFAOYSA-N 0.000 description 8
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230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
RDIVLNOKDXZMJS-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;trihydrochloride Chemical compound Cl.Cl.Cl.NCCNCCN RDIVLNOKDXZMJS-UHFFFAOYSA-N 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
238000011895 specific detection Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1

Classifications

- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Peptides Or Proteins (AREA)
Catalysts (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)
Detergent Compositions (AREA)
Cosmetics (AREA)

ZA200106750A 1999-03-03 2001-08-15 Regioselective synthesis of DTPA derivatives. ZA200106750B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US09/261,207 US6207858B1 (en)	1999-03-03	1999-03-03	Regioselective synthesis of DTPA derivatives

Publications (1)

Publication Number	Publication Date
ZA200106750B true ZA200106750B (en)	2002-11-15

Family

ID=22992340

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200106750A ZA200106750B (en)	1999-03-03	2001-08-15	Regioselective synthesis of DTPA derivatives.

Country Status (20)

Country	Link
US (1)	US6207858B1 (ja)
EP (1)	EP1157004B1 (ja)
JP (2)	JP5357368B2 (ja)
CN (2)	CN1290830C (ja)
AT (1)	ATE396175T1 (ja)
AU (1)	AU778816B2 (ja)
BR (1)	BR0008693A (ja)
CA (1)	CA2364960C (ja)
CY (1)	CY1108271T1 (ja)
DE (1)	DE60038953D1 (ja)
DK (1)	DK1157004T3 (ja)
ES (1)	ES2304944T3 (ja)
HK (1)	HK1069380A1 (ja)
MX (1)	MXPA01008784A (ja)
NO (1)	NO328049B1 (ja)
PL (1)	PL211510B1 (ja)
PT (1)	PT1157004E (ja)
RU (1)	RU2312852C2 (ja)
WO (1)	WO2000051976A1 (ja)
ZA (1)	ZA200106750B (ja)

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US7563433B2 (en) *	2007-01-11	2009-07-21	Immunomedics, Inc.	Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US7993626B2 (en) *	2007-01-11	2011-08-09	Immunomedics, Inc.	Methods and compositions for F-18 labeling of proteins, peptides and other molecules
DE10305463A1 (de) *	2003-02-04	2004-08-12	Schering Ag	Enantiomerenreines (4S,8S)- und (4R,8R)-4-p-Nitrobenzyl-8-methyl-3,6,9-triza-3N,6N,9N-tricarboxymethyl-1,11-undecandisäure und deren Abkömmlinge, Verfahren zu deren Herstellung und Verwendung zur Herstellung pharmazeutischer Mittel
US20040208828A1 (en) *	2003-02-04	2004-10-21	Lutz Lehmann	Enantiomer-pure (4S,8S)- and (4R,8R)-4-p-nitrobenzyl-8-methyl-3,6,9-triaza-3N,6N,9N-tricarboxymethyl-1,11-undecanedioic acid and derivatives thereof, process for their production and use for the production of pharmaceutical agents
DE10305462A1 (de) *	2003-02-04	2004-08-12	Schering Ag	Konjugate enantiomerenreiner (4S,8S)- und (4R,8R)-4-p-Benzyl-8-methyl-3,6,9-triaza-3N, 6N, 9N-tricarboxymethyl-1,11-undecandisäure mit Biomolekülen, Verfahren zu deren Herstellung und Verwendung zur Herstellung
ES2442386T3 (es) *	2004-04-23	2014-02-11	Bundesrepublik Deutschland Letztvertreten Durch Das Robert Koch-Institut Vertreten Durch Seinen Pr	Método para el tratamiento de condiciones mediadas por células T por la disminución de las células positivas de ICOS in vivo.
JP2009508090A (ja) *	2005-08-31	2009-02-26	イムノメディクス，インコーポレイテッド	予め標的化されたポジトロン放出断層撮影画像化のためのｆ−１８ペプチド
WO2008070384A2 (en) *	2006-11-06	2008-06-12	Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services	Method of preparing macromolecular contrast agents and uses thereof
US8153100B2 (en) *	2007-01-11	2012-04-10	Immunomedics, Inc.	Methods and compositions for F-18 labeling of proteins, peptides and other molecules
US8545809B2 (en)	2007-01-11	2013-10-01	Immunomedics, Inc.	Methods and compositions for improved 18F labeling of proteins, peptides and other molecules
US8398956B2 (en)	2007-01-11	2013-03-19	Immunomedics, Inc.	In vivo copper-free click chemistry for delivery of therapeutic and/or diagnostic agents
US8709382B2 (en)	2007-01-11	2014-04-29	Immunomedics, Inc.	Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US8889100B2 (en)	2007-01-11	2014-11-18	Immunomedics, Inc.	Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules
US10189803B2 (en)	2008-02-22	2019-01-29	Illinois Institute Of Technology	Synthesis of therapeutic and diagnostic drugs centered on regioselective and stereoselective ring opening of aziridinium ions
WO2010011367A2 (en) *	2008-02-22	2010-01-28	Illinois Institute Of Technology	Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
US9446995B2 (en)	2012-05-21	2016-09-20	Illinois Institute Of Technology	Synthesis of therapeutic and diagnostic drugs centered on regioselective and stereoselective ring opening of aziridinium ions
US10556873B2 (en)	2008-02-22	2020-02-11	Illinois Institute Of Technology	Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
IN2012DN03177A (ja)	2009-12-04	2015-09-25	Immunomedics Inc
CN102773078A (zh) *	2012-07-16	2012-11-14	武汉纺织大学	同时吸附阳、阴离子的固体配位萃取剂及其制备和应用
US10441669B2 (en)	2013-10-04	2019-10-15	Illinois Institute Of Technology	Multifunctional chelators, complexes, and compositions thereof, and methods of using same
CN103601648B (zh) *	2013-11-19	2015-03-25	宜兴市丰泽化工有限公司	一种dtpa五钠盐的脱盐提纯方法

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PL174721B1 (pl) *	1992-11-13	1998-09-30	Idec Pharma Corp	Przeciwciało monoklonalne anty-CD20
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US6207858B1 (en) *	1999-03-03	2001-03-27	Idec Pharmaceuticals Corporation	Regioselective synthesis of DTPA derivatives

1999
- 1999-03-03 US US09/261,207 patent/US6207858B1/en not_active Expired - Fee Related
2000
- 2000-03-02 JP JP2000602204A patent/JP5357368B2/ja not_active Expired - Lifetime
- 2000-03-02 WO PCT/US2000/005433 patent/WO2000051976A1/en active IP Right Grant
- 2000-03-02 CN CN200410031255.0A patent/CN1290830C/zh not_active Expired - Lifetime
- 2000-03-02 DE DE60038953T patent/DE60038953D1/de not_active Expired - Lifetime
- 2000-03-02 BR BR0008693-2A patent/BR0008693A/pt not_active Application Discontinuation
- 2000-03-02 PL PL350903A patent/PL211510B1/pl unknown
- 2000-03-02 CA CA2364960A patent/CA2364960C/en not_active Expired - Lifetime
- 2000-03-02 MX MXPA01008784A patent/MXPA01008784A/es active IP Right Grant
- 2000-03-02 EP EP00913703A patent/EP1157004B1/en not_active Expired - Lifetime
- 2000-03-02 ES ES00913703T patent/ES2304944T3/es not_active Expired - Lifetime
- 2000-03-02 AU AU35099/00A patent/AU778816B2/en not_active Expired
- 2000-03-02 AT AT00913703T patent/ATE396175T1/de active
- 2000-03-02 DK DK00913703T patent/DK1157004T3/da active
- 2000-03-02 PT PT00913703T patent/PT1157004E/pt unknown
- 2000-03-02 RU RU2001126722/04A patent/RU2312852C2/ru active
- 2000-03-02 CN CN00804499.6A patent/CN1342141A/zh active Pending
2001
- 2001-08-15 ZA ZA200106750A patent/ZA200106750B/en unknown
- 2001-08-29 NO NO20014194A patent/NO328049B1/no not_active IP Right Cessation
2005
- 2005-03-03 HK HK05101857A patent/HK1069380A1/xx not_active IP Right Cessation
2008
- 2008-08-19 CY CY20081100882T patent/CY1108271T1/el unknown
2013
- 2013-03-27 JP JP2013066359A patent/JP2013144705A/ja active Pending

Also Published As

Publication number	Publication date
ES2304944T3 (es)	2008-11-01
BR0008693A (pt)	2001-12-26
CN1548419A (zh)	2004-11-24
PL350903A1 (en)	2003-02-10
CA2364960C (en)	2010-05-11
EP1157004B1 (en)	2008-05-21
RU2312852C2 (ru)	2007-12-20
AU778816B2 (en)	2004-12-23
NO328049B1 (no)	2009-11-16
WO2000051976A1 (en)	2000-09-08
NO20014194D0 (no)	2001-08-29
NO20014194L (no)	2001-10-26
CA2364960A1 (en)	2000-09-08
US6207858B1 (en)	2001-03-27
AU3509900A (en)	2000-09-21
DE60038953D1 (de)	2008-07-03
PL211510B1 (pl)	2012-05-31
PT1157004E (pt)	2008-08-29
JP2002538137A (ja)	2002-11-12
JP2013144705A (ja)	2013-07-25
CN1290830C (zh)	2006-12-20
JP5357368B2 (ja)	2013-12-04
CY1108271T1 (el)	2014-02-12
ATE396175T1 (de)	2008-06-15
CN1342141A (zh)	2002-03-27
HK1069380A1 (en)	2005-05-20
MXPA01008784A (es)	2002-04-24
EP1157004A1 (en)	2001-11-28
DK1157004T3 (da)	2008-09-15

Publication	Publication Date	Title
EP1157004B1 (en)	2008-05-21	Composition comprising MX-DTPA and its use to produce a radiolabeled MX-DTPA
KR101495924B1 (ko)	2015-02-25	[ｆ-１８]-표지된 ｌ-글루탐산, [ｆ-１８]-표지된 ｌ-글루타민, 이들의 유도체 및 이들의 용도 및 이들의 제조 방법
WO1996011954A1 (en)	1996-04-25	Tc or re radiolabelled somatostatin analogs
US6005083A (en)	1999-12-21	Bridged aromatic substituted amine ligands with donor atoms
KR20110009165A (ko)	2011-01-27	신규한 [ｆ-１８]-표지된 ｌ-글루탐산- 및 ｌ-글루타민 유도체 (ｉ), 그의 용도 및 그의 제조 방법
WO2002024235A2 (en)	2002-03-28	Prochelators of radiometal labeled molecules
AU2001277488A1 (en)	2002-06-20	Prochelators of radiometal labeled molecules
US20130034497A1 (en)	2013-02-07	Iodine-labeled homoglutamic acid and glutamic acid derivatives
US5618513A (en)	1997-04-08	Method for preparing radiolabeled peptides
Hammadi et al.	1991	Asymmetric synthesis of (2S)‐and (2R)‐4‐(3‐t‐butylamino‐2‐hydroxypropoxy)‐benzimidazol‐2‐[11C]‐one ((S)‐and (R)‐[11C]‐CGP 12177) from optically active precursors
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WO1996011918A1 (en)	1996-04-25	NOVEL N3S2 CHELATING LIGANDS OPTIONALLY RADIOLABELLED WITH Tc OR Re, USEFUL FOR DIAGNOSTIC OR THERAPEUTIC APPLICATIONS
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KR101931153B1 (ko)	2018-12-20	아민과 선택적으로 결합하며 티오에테르 결합을 갖는 dtpa 킬레이터 및 이의 제조방법
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