DE1922578C3 - 4,7,10-Trioxatrldecan-1,13-dioyibis-(3-carboxy-2,4,6-trijod-anilid) und dessen Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Röntgenkontrastmittel - Google Patents
4,7,10-Trioxatrldecan-1,13-dioyibis-(3-carboxy-2,4,6-trijod-anilid) und dessen Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende RöntgenkontrastmittelInfo
- Publication number
- DE1922578C3 DE1922578C3 DE1922578A DE1922578A DE1922578C3 DE 1922578 C3 DE1922578 C3 DE 1922578C3 DE 1922578 A DE1922578 A DE 1922578A DE 1922578 A DE1922578 A DE 1922578A DE 1922578 C3 DE1922578 C3 DE 1922578C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- carboxy
- triiodo
- anilide
- salts
- 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.)
- Expired
Links
- 239000002872 contrast media Substances 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- 150000003839 salts Chemical class 0.000 title description 7
- 229940039231 contrast media Drugs 0.000 title description 5
- -1 amine salts Chemical class 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 6
- 230000003000 nontoxic effect Effects 0.000 claims description 6
- QMQFFHSJUJDRPG-UHFFFAOYSA-N 3-amino-2,4,6-triiodobenzoic acid Chemical compound NC1=C(I)C=C(I)C(C(O)=O)=C1I QMQFFHSJUJDRPG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 210000000941 bile Anatomy 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000012266 salt solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- MLRRHVDUDKSJLP-UHFFFAOYSA-N 4-[2-[2-(3-carboxypropoxy)ethoxy]ethoxy]butanoic acid Chemical compound C(CCOCCOCCOCCCC(=O)O)C(=O)O MLRRHVDUDKSJLP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910003002 lithium salt Inorganic materials 0.000 description 2
- 159000000002 lithium salts Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SUUMETARNLFNCV-UHFFFAOYSA-N 4-[2-[2-(4-chloro-4-oxobutoxy)ethoxy]ethoxy]butanoyl chloride Chemical compound C(CCOCCOCCOCCCC(=O)Cl)C(=O)Cl SUUMETARNLFNCV-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000006229 Nazarov cyclization reaction Methods 0.000 description 1
- JBIDBRZZDIWWHQ-UHFFFAOYSA-N OP(C(CCOCCOCCOCCC(P(O)(O)O)=O)=O)(O)O Chemical compound OP(C(CCOCCOCCOCCC(P(O)(O)O)=O)=O)(O)O JBIDBRZZDIWWHQ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- FFINMCNLQNTKLU-UHFFFAOYSA-N adipiodone Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FFINMCNLQNTKLU-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003445 biliary tract Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009606 cholecystography Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940029355 iodipamide Drugs 0.000 description 1
- FZDZULUFHNDEDJ-UHFFFAOYSA-N ioglycamic acid Chemical compound OC(=O)C1=C(I)C=C(I)C(NC(=O)COCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I FZDZULUFHNDEDJ-UHFFFAOYSA-N 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0452—Solutions, e.g. for injection
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
- C07C59/315—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH662768A CH502105A (de) | 1968-09-04 | 1968-09-04 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1922578A1 DE1922578A1 (de) | 1969-11-13 |
| DE1922578B2 DE1922578B2 (enExample) | 1974-10-24 |
| DE1922578C3 true DE1922578C3 (de) | 1975-06-05 |
Family
ID=4312547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1922578A Expired DE1922578C3 (de) | 1968-09-04 | 1969-05-02 | 4,7,10-Trioxatrldecan-1,13-dioyibis-(3-carboxy-2,4,6-trijod-anilid) und dessen Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Röntgenkontrastmittel |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3654272A (enExample) |
| AT (1) | AT289086B (enExample) |
| BE (1) | BE732413A (enExample) |
| CH (1) | CH502105A (enExample) |
| DE (1) | DE1922578C3 (enExample) |
| ES (1) | ES366459A1 (enExample) |
| FR (1) | FR2007676A1 (enExample) |
| GB (1) | GB1202677A (enExample) |
| NL (2) | NL6906752A (enExample) |
| YU (1) | YU34116B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3044814A1 (de) * | 1980-11-25 | 1982-07-08 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Unsymmetrisch substituierte dicarbonsaeure-bis-(2,4,6-trijod-anilide), deren herstellung und diese enthaltende roentgenkontrastmittel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853424A (en) * | 1952-08-06 | 1958-09-23 | Schering Ag | X-ray contrast agents comprising symmetrical bifunctional analogs of nu-acyl derivatives of 2, 4, 6 triiodo-3-amino benzoic acid |
-
0
- NL NL696906752A patent/NL139667B/xx unknown
-
1968
- 1968-09-04 CH CH662768A patent/CH502105A/de not_active IP Right Cessation
-
1969
- 1969-04-02 GB GB07365/69A patent/GB1202677A/en not_active Expired
- 1969-04-25 ES ES366459A patent/ES366459A1/es not_active Expired
- 1969-04-30 BE BE732413D patent/BE732413A/xx not_active IP Right Cessation
- 1969-04-30 FR FR6913904A patent/FR2007676A1/fr active Granted
- 1969-04-30 AT AT1117269A patent/AT289086B/de active
- 1969-05-02 NL NL6906752A patent/NL6906752A/xx unknown
- 1969-05-02 DE DE1922578A patent/DE1922578C3/de not_active Expired
- 1969-07-28 YU YU1952/69A patent/YU34116B/xx unknown
- 1969-08-13 US US849858A patent/US3654272A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES366459A1 (es) | 1971-02-16 |
| YU34116B (en) | 1978-12-31 |
| FR2007676B1 (enExample) | 1974-03-22 |
| AT289086B (de) | 1971-04-13 |
| CH502105A (de) | 1971-01-31 |
| BE732413A (enExample) | 1969-10-30 |
| DE1922578A1 (de) | 1969-11-13 |
| DE1922578B2 (enExample) | 1974-10-24 |
| NL139667B (nl) | |
| YU195269A (en) | 1978-06-30 |
| US3654272A (en) | 1972-04-04 |
| GB1202677A (en) | 1970-08-19 |
| NL6906752A (enExample) | 1969-11-04 |
| FR2007676A1 (fr) | 1970-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |