DE1643494B2 - N,n'-bis- eckige klammer auf 3- carboxy-5-(n''-acetyl-n''-methylamino)- 2,4,6-trijodphenyl eckige klammer zu -hydroxyalkylendiamine bzw. -hydroxy- oxa-alkylendiamine, verfahren zu deren herstellung und diese verbindungen enthaltende roentgenkontrastmittel - Google Patents
N,n'-bis- eckige klammer auf 3- carboxy-5-(n''-acetyl-n''-methylamino)- 2,4,6-trijodphenyl eckige klammer zu -hydroxyalkylendiamine bzw. -hydroxy- oxa-alkylendiamine, verfahren zu deren herstellung und diese verbindungen enthaltende roentgenkontrastmittelInfo
- Publication number
- DE1643494B2 DE1643494B2 DE1967P0043585 DEP0043585A DE1643494B2 DE 1643494 B2 DE1643494 B2 DE 1643494B2 DE 1967P0043585 DE1967P0043585 DE 1967P0043585 DE P0043585 A DEP0043585 A DE P0043585A DE 1643494 B2 DE1643494 B2 DE 1643494B2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- square brackets
- compounds
- choh
- acetyl
- 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
- 150000001875 compounds Chemical class 0.000 title description 31
- 239000002872 contrast media Substances 0.000 title description 15
- 238000002360 preparation method Methods 0.000 title description 9
- 238000000034 method Methods 0.000 title description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 47
- 239000000243 solution Substances 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 26
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 210000004204 blood vessel Anatomy 0.000 description 5
- 229940039231 contrast media Drugs 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- 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 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000003445 biliary tract Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 210000000232 gallbladder Anatomy 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GGGDNPWHMNJRFN-UHFFFAOYSA-N metrizoic acid Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I GGGDNPWHMNJRFN-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 210000001835 viscera Anatomy 0.000 description 2
- 241000272814 Anser sp. Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012800 visualization Methods 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
-
- 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
-
- 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
- A61K49/0495—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 intended for oral administration
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Refinement Of Pig-Iron, Manufacture Of Cast Iron, And Steel Manufacture Other Than In Revolving Furnaces (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE17053/66A SE344166B (enExample) | 1966-12-13 | 1966-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643494A1 DE1643494A1 (de) | 1971-07-15 |
| DE1643494B2 true DE1643494B2 (de) | 1976-10-14 |
Family
ID=20303185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967P0043585 Granted DE1643494B2 (de) | 1966-12-13 | 1967-12-12 | N,n'-bis- eckige klammer auf 3- carboxy-5-(n''-acetyl-n''-methylamino)- 2,4,6-trijodphenyl eckige klammer zu -hydroxyalkylendiamine bzw. -hydroxy- oxa-alkylendiamine, verfahren zu deren herstellung und diese verbindungen enthaltende roentgenkontrastmittel |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3678152A (enExample) |
| AT (1) | AT278237B (enExample) |
| CH (1) | CH473586A (enExample) |
| DE (1) | DE1643494B2 (enExample) |
| DK (1) | DK120954B (enExample) |
| FI (1) | FI47525C (enExample) |
| FR (1) | FR7251M (enExample) |
| GB (1) | GB1210230A (enExample) |
| NO (1) | NO121667B (enExample) |
| SE (1) | SE344166B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IT1207226B (it) * | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| EP0108638B1 (en) * | 1982-11-08 | 1986-07-16 | NYEGAARD & CO. A/S | X-ray contrast agents |
| WO2006074809A2 (en) | 2005-01-13 | 2006-07-20 | Cinvention Ag | Composite materials containing carbon nanoparticles |
| EP2104473A1 (en) * | 2007-01-19 | 2009-09-30 | Cinvention Ag | Porous, non-degradable implant made by powder molding |
| WO2009008734A2 (en) | 2007-07-12 | 2009-01-15 | Ge Healthcare As | Contrast agents |
| WO2009047316A1 (en) | 2007-10-12 | 2009-04-16 | Ge Healthcare As | Contrast agents |
| JP2011500533A (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 |
| ES2389974T3 (es) | 2007-10-12 | 2012-11-05 | Ge Healthcare As | Agentes de contraste |
| EP2200655B1 (en) | 2007-10-12 | 2012-07-18 | GE Healthcare AS | Contrast agents |
| JP6884698B2 (ja) | 2014-11-21 | 2021-06-09 | テクニカル ユニバーシティ オブ デンマークＴｅｃｈｎｉｃａｌ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｄｅｎｍａｒｋ | 局所的薬物放出のためのゲル処方物 |
| CA3023928A1 (en) | 2016-05-20 | 2017-11-23 | Technical University Of Denmark | Palpable marker composition |
| WO2020249801A1 (en) | 2019-06-12 | 2020-12-17 | Technical University Of Denmark | Dissacharide formulations for controlled drug release |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3178473A (en) * | 1962-03-02 | 1965-04-13 | Nyegaard & Co As | Process for the n-alkylation of acyl anilides halogen substituted in the nucleus |
| GB1033776A (en) * | 1963-06-06 | 1966-06-22 | Sterling Drug Inc | Iodinated acid amides and esters and salts thereof |
| US3542861A (en) * | 1967-05-08 | 1970-11-24 | Sterling Drug Inc | 3-amino-5-cycloalkylcarbonylamino-2,4,6-triiodobenzoic acids |
-
1966
- 1966-12-13 SE SE17053/66A patent/SE344166B/xx unknown
-
1967
- 1967-12-06 DK DK610367AA patent/DK120954B/da unknown
- 1967-12-11 FI FI673306A patent/FI47525C/fi active
- 1967-12-12 GB GB56367/67A patent/GB1210230A/en not_active Expired
- 1967-12-12 NO NO170938A patent/NO121667B/no unknown
- 1967-12-12 DE DE1967P0043585 patent/DE1643494B2/de active Granted
- 1967-12-12 FR FR131891A patent/FR7251M/fr not_active Expired
- 1967-12-13 CH CH1747867A patent/CH473586A/fr not_active IP Right Cessation
- 1967-12-13 AT AT11241/67A patent/AT278237B/de not_active IP Right Cessation
-
1969
- 1969-10-06 US US864167A patent/US3678152A/en not_active Expired - Lifetime
-
1970
- 1970-04-10 US US27437A patent/US3692824A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE344166B (enExample) | 1972-04-04 |
| US3678152A (en) | 1972-07-18 |
| DK120954B (da) | 1971-08-09 |
| DE1643494A1 (de) | 1971-07-15 |
| FI47525C (fi) | 1974-01-10 |
| GB1210230A (en) | 1970-10-28 |
| US3692824A (en) | 1972-09-19 |
| NO121667B (enExample) | 1971-03-29 |
| FI47525B (enExample) | 1973-10-01 |
| CH473586A (fr) | 1969-06-15 |
| AT278237B (de) | 1970-01-26 |
| FR7251M (enExample) | 1969-09-08 |
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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 |