CA2020142A1 - Derivatized dtpa complexes - Google Patents
Derivatized dtpa complexesInfo
- Publication number
- CA2020142A1 CA2020142A1 CA002020142A CA2020142A CA2020142A1 CA 2020142 A1 CA2020142 A1 CA 2020142A1 CA 002020142 A CA002020142 A CA 002020142A CA 2020142 A CA2020142 A CA 2020142A CA 2020142 A1 CA2020142 A1 CA 2020142A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cooch2c6h5
- independently
- metal ion
- ion equivalent
- 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.)
- Granted
Links
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000003384 imaging method Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
-
- 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
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Radiology & Medical Imaging (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Analysing Materials By The Use Of Radiation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Compounds of the formula (see above formula) wherein:
one of Z1 and Z2 is H, and the other is - (CH2)m-(C6H4)q-(O)k-(CH2)n-(C6H4)l-(O)r-R, wherein m and n, independently, are each 0-20, k, l, q and r are each, independently, 0 or 1, R is H, C1-C6-alkyl, OR1-substituted C1-C6-alkyl or CH2COOR1, where R1 is H, C1-C6-alkyl or benzyl;
and X is, in each case, a hydrogen atom or a metal ion equivalent of an element of atomic number 21-29, 42, 44 or 57-83;
with the provisos that:
at least two of the substituents X represent a metal ion equivalent;
when n and 1 each are 0, then k and r are not simultaneously 1;
at least one of q and l is 1;
-(O)r-R is not OH; and Z1, and Z2 are not -CH2-C6H9-O-CH2-COOCH2C6H5 or -CH2-C6H4-O- (CH2)5-COOCH2C6H5;
as well as their salts with inorganic and/or organic bases, amino acids or amino acid amides, are valuable pharmaceutical agents, e.g., for NMR or X-ray imaging.
one of Z1 and Z2 is H, and the other is - (CH2)m-(C6H4)q-(O)k-(CH2)n-(C6H4)l-(O)r-R, wherein m and n, independently, are each 0-20, k, l, q and r are each, independently, 0 or 1, R is H, C1-C6-alkyl, OR1-substituted C1-C6-alkyl or CH2COOR1, where R1 is H, C1-C6-alkyl or benzyl;
and X is, in each case, a hydrogen atom or a metal ion equivalent of an element of atomic number 21-29, 42, 44 or 57-83;
with the provisos that:
at least two of the substituents X represent a metal ion equivalent;
when n and 1 each are 0, then k and r are not simultaneously 1;
at least one of q and l is 1;
-(O)r-R is not OH; and Z1, and Z2 are not -CH2-C6H9-O-CH2-COOCH2C6H5 or -CH2-C6H4-O- (CH2)5-COOCH2C6H5;
as well as their salts with inorganic and/or organic bases, amino acids or amino acid amides, are valuable pharmaceutical agents, e.g., for NMR or X-ray imaging.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3922005.2 | 1989-06-30 | ||
| DE3922005A DE3922005A1 (en) | 1989-06-30 | 1989-06-30 | DERIVATIVED DTPA COMPLEXES, PHARMACEUTICAL AGENTS CONTAINING THESE COMPOUNDS, THEIR USE AND METHOD FOR THE PRODUCTION THEREOF |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2020142A1 true CA2020142A1 (en) | 1990-12-31 |
| CA2020142C CA2020142C (en) | 2001-04-17 |
Family
ID=6384290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002020142A Expired - Lifetime CA2020142C (en) | 1989-06-30 | 1990-06-29 | Derivatized dtpa complexes |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0405704B1 (en) |
| JP (1) | JP2603357B2 (en) |
| KR (1) | KR100190808B1 (en) |
| AT (1) | ATE115546T1 (en) |
| AU (1) | AU637111B2 (en) |
| CA (1) | CA2020142C (en) |
| CZ (1) | CZ277926B6 (en) |
| DD (1) | DD296276B5 (en) |
| DE (3) | DE3922005A1 (en) |
| DK (1) | DK0405704T3 (en) |
| ES (1) | ES2066113T3 (en) |
| FI (1) | FI102168B1 (en) |
| HK (1) | HK1002810A1 (en) |
| HU (1) | HU210208B (en) |
| IE (1) | IE65676B1 (en) |
| IL (1) | IL94818A (en) |
| NL (1) | NL300182I2 (en) |
| NO (2) | NO179203C (en) |
| NZ (1) | NZ234295A (en) |
| PT (1) | PT94541B (en) |
| RU (1) | RU2086554C1 (en) |
| TW (1) | TW219356B (en) |
| UA (1) | UA27275C2 (en) |
| ZA (1) | ZA905129B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011684A1 (en) | 1990-04-06 | 1991-10-10 | Schering Ag | DTPA MONOAMIDES, PHARMACEUTICAL AGENTS CONTAINING THESE COMPOUNDS, THEIR USE AND METHOD FOR THE PRODUCTION THEREOF |
| DE4302289A1 (en) * | 1993-01-25 | 1994-07-28 | Schering Ag | Process for the preparation of C-substituted diethylenetriamines |
| DE4302287A1 (en) * | 1993-01-25 | 1994-07-28 | Schering Ag | Derivatized DTPA complexes, pharmaceutical compositions containing these compounds, their use and processes for their preparation |
| DE4341724A1 (en) * | 1993-12-03 | 1995-06-08 | Schering Ag | Pharmaceutical compositions containing haloaryl-substituted metal complexes, their use in diagnostics, and methods for producing the complexes and compositions |
| US5582814A (en) * | 1994-04-15 | 1996-12-10 | Metasyn, Inc. | 1-(p-n-butylbenzyl) DTPA for magnetic resonance imaging |
| US5672335A (en) * | 1994-11-30 | 1997-09-30 | Schering Aktiengesellschaft | Use of metal complexes as liver and gallbladder X-ray diagnostic agents |
| AU4173896A (en) * | 1994-11-30 | 1996-06-19 | Schering Aktiengesellschaft | Use of chelate compounds as diagnostic agents in the x-ray examination of liver and bile ducts |
| TW319763B (en) | 1995-02-01 | 1997-11-11 | Epix Medical Inc | |
| CA2212162A1 (en) * | 1995-02-09 | 1996-08-15 | Schering Aktiengesellschaft | Liposomes that contain contrast media for the visualization of intravascular space |
| DE19507820A1 (en) * | 1995-02-21 | 1996-08-22 | Schering Ag | Novel substituted DTPA derivatives, their metal complexes, pharmaceutical compositions containing these complexes, their use in diagnostics, and methods for producing the complexes and compositions |
| JP2759627B2 (en) * | 1995-07-21 | 1998-05-28 | 東北大学長 | Non-ester bondable DTPA derivative and method for producing the same |
| DE19641197C2 (en) * | 1996-09-24 | 1999-02-18 | Schering Ag | Ion pairs and their use as contrast agents |
| DE19646762B4 (en) * | 1996-11-04 | 2004-05-13 | Schering Ag | Use of metal compounds for the production of agents for radiotherapy of tumors |
| DE19712012A1 (en) * | 1997-03-13 | 1998-09-24 | Schering Ag | Ethoxy:benzyl-di:ethylene tri:amine penta:acetic acid preparation |
| US6495118B1 (en) | 1997-09-26 | 2002-12-17 | Schering Aktiengesellschaft | Lipophilic metal complexes for necrosis and infarction imaging |
| DE19744004C1 (en) * | 1997-09-26 | 1999-07-22 | Schering Ag | Lipophilic metal complexes for necrosis and infarct imaging |
| US6534040B2 (en) * | 1999-12-23 | 2003-03-18 | Health Research, Inc. | Chlorin and bacteriochlorin-based aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals |
| FR2867473B1 (en) | 2004-03-12 | 2006-06-23 | Guerbet Sa | PORPHYRINE COMPOUND AND HIGH FIELD USE IN MRI |
| KR100749087B1 (en) * | 2006-06-02 | 2007-08-14 | 경북대학교 산학협력단 | New dtpa-bis-amide ligands and gd-complexes thereof |
| SE533165C2 (en) * | 2008-06-13 | 2010-07-13 | Chemseq Internat Ab | Chemical and process for the complex bonding of metal ions, which are at least divalent |
| EP2338874A1 (en) * | 2009-12-16 | 2011-06-29 | Bracco Imaging S.p.A | Process for the preparation of chelated compounds |
| CN103068790A (en) | 2010-06-11 | 2013-04-24 | 拜耳知识产权有限责任公司 | Process for preparing crystalline 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(4-ethoxybenzyl)undecanedioic acid and use for production of primovist tm |
| DE102010023890A1 (en) | 2010-06-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Preparing crystalline 3,6,9-triaza-3,6,9-tris(carboxymethyl)-4-(ethoxybenzyl)-undecanedioic acid comprises hydrolyzing 3,6,9-triaza-3,6,9-tris(tert-butoxy-carbonylmethyl)-4-(ethoxybenzyl)-undecanedioic acid-ditert-butylester and acidifying |
| CN104761461A (en) * | 2014-09-09 | 2015-07-08 | 山东富创医药科技有限公司 | Preparation method of novel gadoxetate disodium intermediate |
| EP3464237B1 (en) * | 2016-05-30 | 2023-12-20 | Biophore India Pharmaceuticals Pvt. Ltd. | Novel process for the preparation of gadolinium complex of (4s)-4-(4-ethoxybenzyl)-3,6,9-tris(carboxylatomethyl)-3,6,9- triazaundecanedioic acid disodium (gadoxetate disodium) |
| JP6867639B2 (en) * | 2016-10-11 | 2021-05-12 | 学校法人 聖マリアンナ医科大学 | Combined nonionic iodine contrast agent |
| EP4059925A1 (en) | 2021-03-15 | 2022-09-21 | Bayer Aktiengesellschaft | New contrast agent for use in magnetic resonance imaging |
| EP4335840A1 (en) | 2022-09-09 | 2024-03-13 | Bayer Aktiengesellschaft | New contrast agents for use in diagnostic imaging |
| EP4335462A1 (en) | 2022-09-09 | 2024-03-13 | Bayer AG | Contrast agents for use in diagnostic computed tomography imaging |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL194579C (en) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostic. |
| US4672028A (en) * | 1984-05-23 | 1987-06-09 | Icn Micromedic Systems, Inc. | Compositions and method for simultaneous multiple array of analytes using radioisotope chelate labels |
| US4824986A (en) * | 1985-04-26 | 1989-04-25 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Metal chelate protein conjugate |
| IL83966A (en) * | 1986-09-26 | 1992-03-29 | Schering Ag | Amides of aminopolycarboxylic acids and pharmaceutical compositions containing them |
| DE3710730A1 (en) * | 1987-03-31 | 1988-10-20 | Schering Ag | SUBSTITUTED COMPLEX ILLUMINATORS, COMPLEX AND COMPLEX SALTS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THEM |
| AU617338B2 (en) * | 1987-07-16 | 1991-11-28 | Nycomed As | Aminopolycarboxylic acids and derivatives thereof |
| EP0466200B1 (en) * | 1987-07-16 | 1996-04-24 | Nycomed Imaging As | Aminocarboxylic acids and derivatives thereof |
| DE3728525A1 (en) * | 1987-08-24 | 1989-03-16 | Schering Ag | MULTI-CORE SUBSTITUTED COMPLEX ILLUMINATORS, COMPLEX AND COMPLEX SALTS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THEM |
-
1989
- 1989-06-30 DE DE3922005A patent/DE3922005A1/en not_active Withdrawn
-
1990
- 1990-06-21 IL IL9481890A patent/IL94818A/en active IP Right Grant
- 1990-06-26 CZ CS903174A patent/CZ277926B6/en not_active IP Right Cessation
- 1990-06-26 IE IE229990A patent/IE65676B1/en not_active IP Right Cessation
- 1990-06-27 DK DK90250165.9T patent/DK0405704T3/en active
- 1990-06-27 DE DE200412000051 patent/DE122004000051I2/en active Active
- 1990-06-27 KR KR1019900009529A patent/KR100190808B1/en not_active IP Right Cessation
- 1990-06-27 EP EP90250165A patent/EP0405704B1/en not_active Expired - Lifetime
- 1990-06-27 ES ES90250165T patent/ES2066113T3/en not_active Expired - Lifetime
- 1990-06-27 DE DE59007987T patent/DE59007987D1/en not_active Expired - Lifetime
- 1990-06-27 AT AT90250165T patent/ATE115546T1/en active
- 1990-06-28 NZ NZ234295A patent/NZ234295A/en unknown
- 1990-06-29 NO NO902925A patent/NO179203C/en not_active IP Right Cessation
- 1990-06-29 PT PT94541A patent/PT94541B/en not_active IP Right Cessation
- 1990-06-29 AU AU58024/90A patent/AU637111B2/en not_active Expired
- 1990-06-29 JP JP2170372A patent/JP2603357B2/en not_active Expired - Lifetime
- 1990-06-29 ZA ZA905129A patent/ZA905129B/en unknown
- 1990-06-29 CA CA002020142A patent/CA2020142C/en not_active Expired - Lifetime
- 1990-06-29 HU HU904040A patent/HU210208B/en unknown
- 1990-06-29 RU SU904830458A patent/RU2086554C1/en active Protection Beyond IP Right Term
- 1990-06-29 DD DD34235090A patent/DD296276B5/en active IP Right Maintenance
- 1990-06-29 FI FI903295A patent/FI102168B1/en active Protection Beyond IP Right Term
- 1990-06-29 UA UA4830458A patent/UA27275C2/en unknown
- 1990-11-10 TW TW079109532A patent/TW219356B/zh active
-
1998
- 1998-03-10 HK HK98101936A patent/HK1002810A1/en not_active IP Right Cessation
-
2005
- 2005-03-18 NL NL300182C patent/NL300182I2/en unknown
- 2005-05-23 NO NO2005013C patent/NO2005013I2/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |