CS221815B2 - Method of making the diamide of the 2,4,6-triiode -5-carbomoylisoptale acid - Google Patents
Method of making the diamide of the 2,4,6-triiode -5-carbomoylisoptale acid Download PDFInfo
- Publication number
- CS221815B2 CS221815B2 CS819230A CS923081A CS221815B2 CS 221815 B2 CS221815 B2 CS 221815B2 CS 819230 A CS819230 A CS 819230A CS 923081 A CS923081 A CS 923081A CS 221815 B2 CS221815 B2 CS 221815B2
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- Czechoslovakia
- Prior art keywords
- acid
- radical
- compounds
- carbon atoms
- solution
- Prior art date
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- 239000002253 acid Substances 0.000 title description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001470 diamides Chemical class 0.000 claims 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000002872 contrast media Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- -1 alkyl radical Chemical class 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 229940039231 contrast media Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000002583 angiography Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 2
- KHTGTPXXKOLMEH-UHFFFAOYSA-N 5-carbamoyl-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC(=O)C1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I KHTGTPXXKOLMEH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002591 computed tomography Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000009608 myelography Methods 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003204 osmotic effect Effects 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 125000001749 primary amide group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 125000003156 secondary amide group Chemical group 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LCTORNIWLGOBPB-GASJEMHNSA-N (3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical class NC1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LCTORNIWLGOBPB-GASJEMHNSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical compound C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 description 1
- YLJAKJSGUDBOHG-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I YLJAKJSGUDBOHG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- SRBNFMSMBDTDQR-UHFFFAOYSA-N 3,5-dicarbamoyl-2,4,6-triiodobenzoic acid Chemical compound NC(=O)C1=C(I)C(C(N)=O)=C(I)C(C(O)=O)=C1I SRBNFMSMBDTDQR-UHFFFAOYSA-N 0.000 description 1
- DDDYCRWAEFCAGI-UHFFFAOYSA-N 3-(acetamidomethyl)-5-cyano-2,4,6-triiodobenzoic acid Chemical compound CC(=O)NCC1=C(I)C(C#N)=C(I)C(C(O)=O)=C1I DDDYCRWAEFCAGI-UHFFFAOYSA-N 0.000 description 1
- YSWWITLPDXXKGO-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)carbamoyl]-5-cyano-2,4,6-triiodobenzoic acid Chemical compound OCCN(CCO)C(=O)C1=C(I)C(C#N)=C(I)C(C(O)=O)=C1I YSWWITLPDXXKGO-UHFFFAOYSA-N 0.000 description 1
- WRXPJJPJHDCFBH-UHFFFAOYSA-N 3-carbamoyl-5-cyano-2,4,6-triiodobenzoic acid Chemical compound NC(=O)C1=C(I)C(C#N)=C(I)C(C(O)=O)=C1I WRXPJJPJHDCFBH-UHFFFAOYSA-N 0.000 description 1
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 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 1
- YQNFBOJPTAXAKV-OMCISZLKSA-N Iopodic acid Chemical compound CN(C)\C=N\C1=C(I)C=C(I)C(CCC(O)=O)=C1I YQNFBOJPTAXAKV-OMCISZLKSA-N 0.000 description 1
- UXIGWFXRQKWHHA-UHFFFAOYSA-N Iotalamic acid Chemical compound CNC(=O)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I UXIGWFXRQKWHHA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- QATVIDMOOZNPPN-UHFFFAOYSA-N N.[Na+].[Na+].[Na+] Chemical compound N.[Na+].[Na+].[Na+] QATVIDMOOZNPPN-UHFFFAOYSA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- VEUACKUBDLVUAC-UHFFFAOYSA-N [Na].[Ca] Chemical compound [Na].[Ca] VEUACKUBDLVUAC-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 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
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000002397 epileptogenic effect Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940029355 iodipamide Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000002611 ionic contrast media Substances 0.000 description 1
- 229960000929 iotalamic acid Drugs 0.000 description 1
- 229940029409 ipodate Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005907 ketalization reaction Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000036651 mood Effects 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
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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- 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)
- Polyesters Or Polycarbonates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Absorbent Articles And Supports Therefor (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Physical Deposition Of Substances That Are Components Of Semiconductor Devices (AREA)
- Dental Preparations (AREA)
- Polyurethanes Or Polyureas (AREA)
- Steroid Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803001292 DE3001292A1 (de) | 1980-01-11 | 1980-01-11 | Nichtionische 5-c-substituierte 2,4,6-trijod-isophthalsaeure-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221815B2 true CS221815B2 (en) | 1983-04-29 |
Family
ID=6092104
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS819230A CS221815B2 (en) | 1980-01-11 | 1981-01-09 | Method of making the diamide of the 2,4,6-triiode -5-carbomoylisoptale acid |
| CS81204A CS221814B2 (en) | 1980-01-11 | 1981-01-09 | Method of making the triamide of the acid of 2,4,6-triiodebenzen-1,3-5-tricarboxyle |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS81204A CS221814B2 (en) | 1980-01-11 | 1981-01-09 | Method of making the triamide of the acid of 2,4,6-triiodebenzen-1,3-5-tricarboxyle |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5047228A (enExample) |
| EP (1) | EP0032387B1 (enExample) |
| JP (1) | JPS579741A (enExample) |
| AT (1) | ATE5189T1 (enExample) |
| AU (1) | AU546142B2 (enExample) |
| CA (1) | CA1201126A (enExample) |
| CS (2) | CS221815B2 (enExample) |
| DD (1) | DD156969A5 (enExample) |
| DE (2) | DE3001292A1 (enExample) |
| DK (1) | DK159846C (enExample) |
| EG (1) | EG15038A (enExample) |
| ES (3) | ES498252A0 (enExample) |
| FI (1) | FI75147C (enExample) |
| GR (1) | GR73164B (enExample) |
| HU (1) | HU185234B (enExample) |
| IE (1) | IE50805B1 (enExample) |
| IL (1) | IL61873A (enExample) |
| NO (1) | NO158182C (enExample) |
| PT (1) | PT72326B (enExample) |
| YU (2) | YU326680A (enExample) |
| ZA (1) | ZA81150B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127373A (en) * | 1980-01-31 | 1981-10-06 | Univ California | Novel amino-dioxepane intermediate for synthesizing novel nonionic contrast agent |
| FR2512014A1 (fr) * | 1981-08-28 | 1983-03-04 | Guerbet Sa | Composes bromes utilisables dans des produits opacifiants |
| US4567034A (en) * | 1984-09-07 | 1986-01-28 | E. R. Squibb & Sons, Inc. | Esters of diatrizoic acid as X-ray contrast agents |
| IL94718A (en) * | 1989-07-05 | 1994-10-21 | Schering Ag | Non-ionic carboxamide contrast agent and method of preparation |
| US5698739A (en) * | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| US5463080A (en) * | 1992-08-27 | 1995-10-31 | Bracco International B.V. | 2,4,6-triiodo-1,3-benzenedicarboxylic acid compounds used as radiolabelling reagents |
| US5312616A (en) * | 1993-03-11 | 1994-05-17 | Sterling Winthrop Inc. | Compositions of iodobenzoic acid derivatives in film-forming materials for visualization of the gastrointestinal tract |
| US5344638A (en) * | 1993-03-11 | 1994-09-06 | Sterling Winthrop Inc. | Compositions of iodobenzoic acid derivatives for visualization of the gastrointestinal tract |
| US6310243B1 (en) * | 1994-09-23 | 2001-10-30 | Nycomed Imaging As | Iodinated x-ray contrast media |
| GB9419203D0 (en) * | 1994-09-23 | 1994-11-09 | Nycomed Innovation Ab | Contrast media |
| WO1997000240A1 (en) * | 1995-06-16 | 1997-01-03 | Biophysica Foundation | Formyl derivatives as nonionic contrast media |
| US5742205A (en) * | 1995-07-27 | 1998-04-21 | Scientific-Atlanta, Inc. | Field effect transistor cable television line amplifier |
| JP4582918B2 (ja) * | 1999-04-30 | 2010-11-17 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 造影剤 |
| US6660248B2 (en) | 2000-11-10 | 2003-12-09 | William Marsh Rice University | Fullerene (C60)-based X-ray contrast agent for diagnostic imaging |
| US7166740B2 (en) | 2003-07-14 | 2007-01-23 | Schering Ag | Process for the production of triiodotrimesic acid |
| DE10332574B3 (de) * | 2003-07-14 | 2005-04-14 | Schering Ag | Verfahren zur Herstellung von Triiodtrimesinsäure |
| US7083516B2 (en) * | 2003-07-14 | 2006-08-01 | Schering Ag | Process for the production of triiodotrimesic acid |
| DE10332552B3 (de) * | 2003-07-14 | 2005-03-24 | Schering Ag | Verfahren zur Herstellung von Triiodtrimesinsäure |
| JP2005037464A (ja) * | 2003-07-16 | 2005-02-10 | Matsushita Electric Ind Co Ltd | 光導波路とその製造方法 |
| US20060009694A1 (en) * | 2004-05-17 | 2006-01-12 | Yousefzadeh David K | Methods of attenuating internal radiation exposure |
| WO2006074809A2 (en) | 2005-01-13 | 2006-07-20 | Cinvention Ag | Composite materials containing carbon nanoparticles |
| US20080206862A1 (en) * | 2007-02-28 | 2008-08-28 | Cinvention Ag | High surface cultivation system bag |
| BRPI0807993A2 (pt) * | 2007-02-28 | 2014-06-17 | Cinv Ag | Sistema de cultivo de alta superfície. |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES381202A1 (es) * | 1969-06-27 | 1973-04-16 | Nyegaard & Co As | Un procedimiento para la preparacion de agentes de contras-te de rayos x. |
| 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 |
| JPS5147702A (enExample) * | 1974-10-18 | 1976-04-23 | Toyo Tire & Rubber Co | |
| CH608189A5 (enExample) * | 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 |
| NL7905354A (nl) * | 1978-07-14 | 1980-01-16 | Schering Ag | Als roentgen-contrastmiddelen bruikbare trijoodbenzonitril-derivaten. |
-
1980
- 1980-01-11 DE DE19803001292 patent/DE3001292A1/de not_active Withdrawn
- 1980-12-24 YU YU03266/80A patent/YU326680A/xx unknown
- 1980-12-30 ES ES498252A patent/ES498252A0/es active Granted
-
1981
- 1981-01-07 FI FI810031A patent/FI75147C/fi not_active IP Right Cessation
- 1981-01-07 DD DD81226868A patent/DD156969A5/de unknown
- 1981-01-07 IL IL61873A patent/IL61873A/xx unknown
- 1981-01-08 PT PT72326A patent/PT72326B/pt unknown
- 1981-01-09 EP EP81100106A patent/EP0032387B1/de not_active Expired
- 1981-01-09 DK DK008881A patent/DK159846C/da not_active IP Right Cessation
- 1981-01-09 DE DE8181100106T patent/DE3161294D1/de not_active Expired
- 1981-01-09 AT AT81100106T patent/ATE5189T1/de not_active IP Right Cessation
- 1981-01-09 CS CS819230A patent/CS221815B2/cs unknown
- 1981-01-09 ZA ZA00810150A patent/ZA81150B/xx unknown
- 1981-01-09 CA CA000368163A patent/CA1201126A/en not_active Expired
- 1981-01-09 CS CS81204A patent/CS221814B2/cs unknown
- 1981-01-09 IE IE35/81A patent/IE50805B1/en not_active IP Right Cessation
- 1981-01-09 AU AU66096/81A patent/AU546142B2/en not_active Ceased
- 1981-01-09 NO NO810069A patent/NO158182C/no unknown
- 1981-01-09 GR GR63834A patent/GR73164B/el unknown
- 1981-01-09 HU HU8157A patent/HU185234B/hu unknown
- 1981-01-11 EG EG8107A patent/EG15038A/xx active
- 1981-01-12 JP JP219581A patent/JPS579741A/ja active Granted
- 1981-02-13 ES ES499409A patent/ES499409A0/es active Granted
- 1981-02-13 ES ES499406A patent/ES499406A0/es active Granted
-
1983
- 1983-04-19 YU YU00891/83A patent/YU89183A/xx unknown
-
1989
- 1989-03-02 US US07/318,454 patent/US5047228A/en not_active Expired - Lifetime
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