IE51495B1 - N-hydroxyalkylated dicarboxylic acid bis-(3,5-dicarbamoyl-2,4,6-triiodoanilides),process for their preparation,and x-ray contrast preparations containing them - Google Patents
N-hydroxyalkylated dicarboxylic acid bis-(3,5-dicarbamoyl-2,4,6-triiodoanilides),process for their preparation,and x-ray contrast preparations containing themInfo
- Publication number
- IE51495B1 IE51495B1 IE1841/81A IE184181A IE51495B1 IE 51495 B1 IE51495 B1 IE 51495B1 IE 1841/81 A IE1841/81 A IE 1841/81A IE 184181 A IE184181 A IE 184181A IE 51495 B1 IE51495 B1 IE 51495B1
- Authority
- IE
- Ireland
- Prior art keywords
- bis
- compound
- acid bis
- triiodo
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 13
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 42
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 235000006408 oxalic acid Nutrition 0.000 claims description 9
- 150000003931 anilides Chemical class 0.000 claims description 7
- CQWXKASOCUAEOW-UHFFFAOYSA-N 2-[2-(carboxymethoxy)ethoxy]acetic acid Chemical compound OC(=O)COCCOCC(O)=O CQWXKASOCUAEOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000003745 diagnosis Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 210000004013 groin Anatomy 0.000 claims 1
- 125000000369 oxido group Chemical group [*]=O 0.000 claims 1
- 239000002872 contrast media Substances 0.000 abstract description 13
- 229940039231 contrast media Drugs 0.000 abstract description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 5
- 239000011630 iodine Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
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- WELYMXBGZUGIPD-UHFFFAOYSA-N 5-[[2-[3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-oxoacetyl]amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound OC(CNC(=O)C=1C(=C(NC(C(=O)NC2=C(C(=C(C(=C2I)C(NCC(CO)O)=O)I)C(NCC(CO)O)=O)I)=O)C(=C(C=1I)C(NCC(CO)O)=O)I)I)CO WELYMXBGZUGIPD-UHFFFAOYSA-N 0.000 description 2
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- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical class OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
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- DQSWHEHCNFKNSQ-UHFFFAOYSA-N 5-[2-hydroxyethyl-[3-[N-(2-hydroxyethyl)-2,4,6-triiodo-3,5-bis(1,3,4-trihydroxybutan-2-ylcarbamoyl)anilino]-3-oxopropanoyl]amino]-2,4,6-triiodo-1-N,3-N-bis(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide Chemical compound OC(C(CO)NC(=O)C=1C(=C(N(C(CC(=O)N(C2=C(C(=C(C(=C2I)C(NC(C(CO)O)CO)=O)I)C(NC(C(CO)O)CO)=O)I)CCO)=O)CCO)C(=C(C=1I)C(NC(C(CO)O)CO)=O)I)I)CO DQSWHEHCNFKNSQ-UHFFFAOYSA-N 0.000 description 1
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- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940037001 sodium edetate Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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)
- Photoreceptors In Electrophotography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803038853 DE3038853A1 (de) | 1980-10-10 | 1980-10-10 | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE811841L IE811841L (en) | 1982-05-10 |
| IE51495B1 true IE51495B1 (en) | 1987-01-07 |
Family
ID=6114382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1841/81A IE51495B1 (en) | 1980-10-10 | 1981-08-12 | N-hydroxyalkylated dicarboxylic acid bis-(3,5-dicarbamoyl-2,4,6-triiodoanilides),process for their preparation,and x-ray contrast preparations containing them |
Country Status (14)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3364536D1 (en) * | 1982-11-08 | 1986-08-21 | Nyegaard & Co As | X-ray contrast agents |
| NL194579C (nl) * | 1983-01-21 | 2002-08-05 | Schering Ag | Diagnostisch middel. |
| FR2541272A1 (fr) * | 1983-02-23 | 1984-08-24 | Guerbet Sa | Composes bromes et produits opacifiants en contenant |
| DE3731542A1 (de) * | 1987-09-17 | 1989-03-30 | Schering Ag | Neue dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6-triiod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
| DE3739098A1 (de) * | 1987-11-16 | 1989-05-24 | Schering Ag | Neue substituierte dicarbonsaeure-bis(3,5-dicarbamoyl-2,4,6- trijod-anilide), verfahren zu deren herstellung sowie diese enthaltende roentgenkontrastmittel |
| GB8906130D0 (en) * | 1989-03-17 | 1989-05-04 | Nycomed As | Compositions |
| US5698739A (en) * | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| US5075502A (en) * | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| US5191120A (en) * | 1989-12-13 | 1993-03-02 | Mallinckrodt Medical, Inc. | Process for preparing nonionic X-ray contrast agents |
| GB9020091D0 (en) * | 1990-09-14 | 1990-10-24 | Nycomed As | Contrast media |
| WO1993010078A1 (es) * | 1991-11-18 | 1993-05-27 | Centro Investigacion Justesa Imagen S.A. | Nuevos agentes yodados no ionicos de contraste a los rayos x, metodo para su preparacion y composiciones galenicas que los contienen |
| WO1993010825A1 (en) * | 1991-12-03 | 1993-06-10 | Mallinckrodt Medical, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| FR2687669B1 (fr) * | 1992-02-24 | 1997-12-19 | Guerbet Sa | Composes utilisables dans des produits de contraste pour la radiographie. |
| AU5093993A (en) * | 1992-09-02 | 1994-03-29 | Mallinckrodt Medical, Inc. | Nonionic X-ray contrast agents compositions and methods |
| WO1995026331A1 (es) * | 1994-03-25 | 1995-10-05 | Centro Investigacion Justesa Imagen, S.A. | Nuevos dimeros iodados no ionicos como agentes de contraste a los rayos x, metodo para su preparacion y composiciones farmaceuticas que los contienen |
| AU2002245169A1 (en) | 2000-11-10 | 2002-07-08 | Wm. Marsh Rice University | Fullerene (c60)-based x-ray contrast agent for diagnostic imaging |
| PL1836239T3 (pl) | 2005-01-13 | 2009-04-30 | Cinvention Ag | Materiał kompozytowy zawierający nanocząstki węgla |
| CN101687051A (zh) | 2007-07-12 | 2010-03-31 | 通用电气医疗集团股份有限公司 | 造影剂 |
| US20100221192A1 (en) | 2007-10-12 | 2010-09-02 | Duncan George Wynn | Contrast agents |
| JP2011500530A (ja) | 2007-10-12 | 2011-01-06 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| WO2009047319A1 (en) | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| WO2009047316A1 (en) | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| US8445725B2 (en) * | 2008-01-14 | 2013-05-21 | Mallinckrodt Llc | Process for the preparation of iosimenol |
| WO2012136813A2 (en) | 2011-04-07 | 2012-10-11 | Universitetet I Oslo | Agents for medical radar diagnosis |
| CN107249570B (zh) | 2014-11-21 | 2022-08-09 | 丹麦技术大学 | 用于局部药物释放的凝胶制剂 |
| SG11201809729XA (en) | 2016-05-20 | 2018-12-28 | Univ Denmark Tech Dtu | Palpable marker composition |
| WO2020249801A1 (en) | 2019-06-12 | 2020-12-17 | Technical University Of Denmark | Dissacharide formulations for controlled drug release |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021481A (en) | 1969-06-27 | 1977-05-03 | Nyegaard & Co. A/S | Amido derivatives of 2,4,6-triiodobenzoic acids containing at least one N-hydroxyalkyl and at least two hydroxyl groups |
| DE2031724C3 (de) | 1969-06-27 | 1979-06-28 | Nyegaard & Co. A/S., Oslo | N-substituierte Trijodbenz- bzw. Jodmethansulfon-am'ide, Verfahren zu deren Herstellung und radiologische Zusammensetzungen |
| DD104193A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-12-22 | 1974-03-05 | ||
| CH608189A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| GB1491129A (en) | 1975-06-04 | 1977-11-09 | Guerbet Sa | Iodo-benzene derivatives and an x-ray contrast medium containing them |
| GB1548594A (en) | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
| DE2628517C2 (de) * | 1976-06-23 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Dicarbonsäure-bis(3,5-dicarbamoyl-2,4,6-trijodanilid)-Verbindungen, Verfahren zu ihrer Herstellung und Röntgenkontrastmittel |
| CH626873A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| US4230845A (en) | 1978-08-31 | 1980-10-28 | Mallinckrodt, Inc. | Polyhydroxy-alkyl-3,5-disubstituted-2,4,6-triiodocarbanilates |
| DE2852094A1 (de) * | 1978-11-30 | 1980-06-12 | Schering Ag | Neue roentgenkontrastmittel |
| DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
| DE2928417A1 (de) | 1979-07-12 | 1981-01-29 | Schering Ag | Trijodierte basen |
| IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
-
1980
- 1980-10-10 DE DE19803038853 patent/DE3038853A1/de not_active Withdrawn
-
1981
- 1981-07-07 DK DK300281A patent/DK158468C/da not_active IP Right Cessation
- 1981-07-31 IL IL63480A patent/IL63480A/xx not_active IP Right Cessation
- 1981-08-07 AT AT81106183T patent/ATE10488T1/de not_active IP Right Cessation
- 1981-08-07 EP EP81106183A patent/EP0049745B1/de not_active Expired
- 1981-08-07 DE DE8181106183T patent/DE3167463D1/de not_active Expired
- 1981-08-11 GR GR65764A patent/GR75308B/el unknown
- 1981-08-11 AU AU73978/81A patent/AU545934B2/en not_active Ceased
- 1981-08-12 IE IE1841/81A patent/IE51495B1/en not_active IP Right Cessation
- 1981-08-12 ES ES504701A patent/ES504701A0/es active Granted
- 1981-08-12 CA CA000383725A patent/CA1186333A/en not_active Expired
- 1981-08-12 US US06/292,115 patent/US4426371A/en not_active Expired - Lifetime
- 1981-08-13 JP JP56126061A patent/JPS57145849A/ja active Granted
- 1981-08-13 NO NO812753A patent/NO154550C/no unknown
- 1981-08-13 PH PH26047A patent/PH18855A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0049745A1 (de) | 1982-04-21 |
| GR75308B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-13 |
| EP0049745B1 (de) | 1984-11-28 |
| US4426371A (en) | 1984-01-17 |
| NO154550C (no) | 1986-10-15 |
| IL63480A0 (en) | 1981-10-30 |
| JPS57145849A (en) | 1982-09-09 |
| DE3038853A1 (de) | 1982-05-27 |
| NO812753L (no) | 1982-04-13 |
| IL63480A (en) | 1984-03-30 |
| AU545934B2 (en) | 1985-08-08 |
| IE811841L (en) | 1982-05-10 |
| DE3167463D1 (en) | 1985-01-10 |
| ES8205757A1 (es) | 1982-08-16 |
| NO154550B (no) | 1986-07-07 |
| DK158468C (da) | 1990-10-08 |
| ATE10488T1 (de) | 1984-12-15 |
| AU7397881A (en) | 1982-04-22 |
| JPH0222066B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-05-17 |
| CA1186333A (en) | 1985-04-30 |
| DK158468B (da) | 1990-05-21 |
| PH18855A (en) | 1985-10-21 |
| ES504701A0 (es) | 1982-08-16 |
| DK300281A (da) | 1982-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |