CA1133935A - Triio dophenyl-aminopropionic acids and x-ray contrast media comprising the same - Google Patents
Triio dophenyl-aminopropionic acids and x-ray contrast media comprising the sameInfo
- Publication number
- CA1133935A CA1133935A CA324,144A CA324144A CA1133935A CA 1133935 A CA1133935 A CA 1133935A CA 324144 A CA324144 A CA 324144A CA 1133935 A CA1133935 A CA 1133935A
- Authority
- CA
- Canada
- Prior art keywords
- acetyl
- triiodophenyl
- compound
- beta
- recovering
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 10
- 239000002872 contrast media Substances 0.000 title abstract description 10
- 150000007513 acids Chemical class 0.000 title abstract description 5
- 229940039231 contrast media Drugs 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 159000000007 calcium salts Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- -1 acids compounds Chemical class 0.000 abstract description 2
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 210000000013 bile duct Anatomy 0.000 description 4
- 210000000232 gallbladder Anatomy 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002601 radiography Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000012800 visualization Methods 0.000 description 2
- GSVQIUGOUKJHRC-YFKPBYRVSA-N (2s)-3-(n-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acid Chemical compound OC(=O)[C@@H](C)CN(C(C)=O)C1=C(I)C=C(I)C(N)=C1I GSVQIUGOUKJHRC-YFKPBYRVSA-N 0.000 description 1
- BSIWIVCJKKGHQY-UHFFFAOYSA-N 2-acetamido-2-methylpropanoic acid Chemical compound CC(=O)NC(C)(C)C(O)=O BSIWIVCJKKGHQY-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical group CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 101100460716 Aspergillus sp. (strain MF297-2) notO gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 241001024304 Mino Species 0.000 description 1
- 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 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical group CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229960001943 iocetamic acid Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/48—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13200/78A GB1583613A (en) | 1978-04-04 | 1978-04-04 | Triiodophenylaminopropionic acids and x-ray contrast media comprising the same |
| GB13200/78 | 1978-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1133935A true CA1133935A (en) | 1982-10-19 |
Family
ID=10018663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA324,144A Expired CA1133935A (en) | 1978-04-04 | 1979-03-26 | Triio dophenyl-aminopropionic acids and x-ray contrast media comprising the same |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS54148733A (sv) |
| AU (1) | AU519875B2 (sv) |
| BE (1) | BE874998A (sv) |
| CA (1) | CA1133935A (sv) |
| DE (1) | DE2913299A1 (sv) |
| DK (1) | DK135979A (sv) |
| FI (1) | FI791082A (sv) |
| FR (1) | FR2421877A1 (sv) |
| GB (1) | GB1583613A (sv) |
| GR (1) | GR71192B (sv) |
| IL (1) | IL56927A (sv) |
| IT (1) | IT1164113B (sv) |
| NL (1) | NL7902104A (sv) |
| PT (1) | PT69400A (sv) |
| SE (1) | SE7902783L (sv) |
| ZA (1) | ZA791500B (sv) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3073814A (en) * | 1960-07-25 | 1963-01-15 | Mallinckrodt Chemical Works | Triiodobenzoic acid derivatives |
-
1978
- 1978-04-04 GB GB13200/78A patent/GB1583613A/en not_active Expired
-
1979
- 1979-03-16 NL NL7902104A patent/NL7902104A/xx not_active Application Discontinuation
- 1979-03-21 BE BE0/194139A patent/BE874998A/xx not_active IP Right Cessation
- 1979-03-22 IL IL56927A patent/IL56927A/xx unknown
- 1979-03-26 CA CA324,144A patent/CA1133935A/en not_active Expired
- 1979-03-27 GR GR58698A patent/GR71192B/el unknown
- 1979-03-28 SE SE7902783A patent/SE7902783L/sv unknown
- 1979-03-28 PT PT69400A patent/PT69400A/pt unknown
- 1979-03-29 ZA ZA791500A patent/ZA791500B/xx unknown
- 1979-03-30 JP JP3713679A patent/JPS54148733A/ja active Pending
- 1979-03-30 AU AU45567/79A patent/AU519875B2/en not_active Ceased
- 1979-04-02 FI FI791082A patent/FI791082A/fi not_active Application Discontinuation
- 1979-04-03 DK DK135979A patent/DK135979A/da not_active Application Discontinuation
- 1979-04-03 IT IT48595/79A patent/IT1164113B/it active
- 1979-04-03 DE DE19792913299 patent/DE2913299A1/de not_active Withdrawn
- 1979-04-03 FR FR7908340A patent/FR2421877A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE7902783L (sv) | 1979-10-05 |
| FR2421877A1 (fr) | 1979-11-02 |
| BE874998A (fr) | 1979-07-16 |
| NL7902104A (nl) | 1979-10-08 |
| IT1164113B (it) | 1987-04-08 |
| JPS54148733A (en) | 1979-11-21 |
| IL56927A (en) | 1982-01-31 |
| AU519875B2 (en) | 1981-12-24 |
| DE2913299A1 (de) | 1979-10-18 |
| PT69400A (en) | 1979-04-01 |
| IT7948595A0 (it) | 1979-04-03 |
| IL56927A0 (en) | 1979-05-31 |
| GR71192B (sv) | 1983-04-11 |
| DK135979A (da) | 1979-10-05 |
| GB1583613A (en) | 1981-01-28 |
| FR2421877B1 (sv) | 1981-11-20 |
| AU4556779A (en) | 1979-10-18 |
| FI791082A (fi) | 1979-10-05 |
| ZA791500B (en) | 1980-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |