HU176251B - Process for producing 2,4,6-triiodo-benzoic acid derivatives substituted with 2,4,6-triiodo-benzoyl-amino-alkyl-acetamido group - Google Patents
Process for producing 2,4,6-triiodo-benzoic acid derivatives substituted with 2,4,6-triiodo-benzoyl-amino-alkyl-acetamido group Download PDFInfo
- Publication number
- HU176251B HU176251B HU75GU331A HUGU000331A HU176251B HU 176251 B HU176251 B HU 176251B HU 75GU331 A HU75GU331 A HU 75GU331A HU GU000331 A HUGU000331 A HU GU000331A HU 176251 B HU176251 B HU 176251B
- Authority
- HU
- Hungary
- Prior art keywords
- triiodo
- formula
- benzoic acid
- mgl
- methylcarbamoyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical group OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 8
- 239000002872 contrast media Substances 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- -1 N-methylcarbamoyl Chemical group 0.000 claims description 306
- 239000005711 Benzoic acid Substances 0.000 claims description 175
- 239000000243 solution Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 18
- 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 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 239000011630 iodine Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000003204 osmotic effect Effects 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 241000699670 Mus sp. Species 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 241000282326 Felis catus Species 0.000 claims description 3
- 125000002252 acyl group Polymers 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 231100000403 acute toxicity Toxicity 0.000 claims description 2
- 230000007059 acute toxicity Effects 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000029142 excretion Effects 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 230000024883 vasodilation Effects 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 4
- 235000011037 adipic acid Nutrition 0.000 claims 2
- WXLJJIHGDBUBJM-UHFFFAOYSA-N 1,3,5-triiodobenzene Chemical compound IC1=CC(I)=CC(I)=C1 WXLJJIHGDBUBJM-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 claims 1
- 238000002583 angiography Methods 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000009608 myelography Methods 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 10
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- 239000003480 eluent Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000004809 thin layer chromatography Methods 0.000 description 29
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 235000010233 benzoic acid Nutrition 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000021736 acetylation Effects 0.000 description 5
- 238000006640 acetylation reaction Methods 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000003749 cleanliness Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 210000002435 tendon Anatomy 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VJEZYZLITKUTFH-UHFFFAOYSA-N 2-(hydrazinecarbonyl)benzoic acid Chemical compound NNC(=O)C1=CC=CC=C1C(O)=O VJEZYZLITKUTFH-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229940105631 nembutal Drugs 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- SAGQGRMEBBBUCA-IXCHPVQKSA-N (2S,3S,4R,5R)-2,3,4,5-tetraacetyl-2,3,4,5,6-pentahydroxy-7-oxooctanoyl chloride Chemical compound C(C)(=O)C([C@]([C@]([C@@]([C@](C(=O)Cl)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)(O)C(C)=O)O SAGQGRMEBBBUCA-IXCHPVQKSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical class OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- ZEQHPUCQCWTFRP-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)propanoyl chloride Chemical compound C1=CC=C2C(=O)N(CCC(=O)Cl)C(=O)C2=C1 ZEQHPUCQCWTFRP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101000878595 Arabidopsis thaliana Squalene synthase 1 Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ZZNTYUTVZBEQIB-UHFFFAOYSA-N [2-(acetyloxymethyl)-3-chloro-2-methyl-3-oxopropyl] acetate Chemical compound CC(=O)OCC(C)(C(Cl)=O)COC(C)=O ZZNTYUTVZBEQIB-UHFFFAOYSA-N 0.000 description 1
- NOSIYYJFMPDDSA-UHFFFAOYSA-N acepromazine Chemical compound C1=C(C(C)=O)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 NOSIYYJFMPDDSA-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 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
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24169/74A GB1488903A (en) | 1974-05-31 | 1974-05-31 | X-ray contrast media |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176251B true HU176251B (en) | 1981-01-28 |
Family
ID=10207490
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU75GU331A HU176251B (en) | 1974-05-31 | 1975-05-28 | Process for producing 2,4,6-triiodo-benzoic acid derivatives substituted with 2,4,6-triiodo-benzoyl-amino-alkyl-acetamido group |
| HU75GU317A HU174153B (hu) | 1974-05-31 | 1975-05-28 | Sposob poluchenija proizvodnykh 2,4,6-triiodo-bis-2,4,6-triiodo-3,5-bis-skobka-karbamoil-skobka zakryta-fenil-karbamoil-metil-amino-acetamido-5-benzojjnojj kisloty |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU75GU317A HU174153B (hu) | 1974-05-31 | 1975-05-28 | Sposob poluchenija proizvodnykh 2,4,6-triiodo-bis-2,4,6-triiodo-3,5-bis-skobka-karbamoil-skobka zakryta-fenil-karbamoil-metil-amino-acetamido-5-benzojjnojj kisloty |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4005188A (en, 2012) |
| JP (2) | JPS585186B2 (en, 2012) |
| AR (1) | AR205196A1 (en, 2012) |
| AT (1) | AT345796B (en, 2012) |
| BE (2) | BE829573A (en, 2012) |
| BR (1) | BR7503406A (en, 2012) |
| CA (1) | CA1071228A (en, 2012) |
| CH (1) | CH597159A5 (en, 2012) |
| CS (1) | CS207562B2 (en, 2012) |
| DE (1) | DE2524059A1 (en, 2012) |
| DK (1) | DK137945B (en, 2012) |
| EG (1) | EG12474A (en, 2012) |
| ES (2) | ES437997A1 (en, 2012) |
| FR (1) | FR2272655B1 (en, 2012) |
| GB (1) | GB1488903A (en, 2012) |
| HU (2) | HU176251B (en, 2012) |
| NL (1) | NL7506400A (en, 2012) |
| NO (1) | NO139918C (en, 2012) |
| SE (1) | SE410849B (en, 2012) |
| SU (4) | SU665797A3 (en, 2012) |
| ZA (1) | ZA753131B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1491129A (en) * | 1975-06-04 | 1977-11-09 | Guerbet Sa | Iodo-benzene derivatives and an x-ray contrast medium containing them |
| CH626873A5 (en, 2012) * | 1977-03-28 | 1981-12-15 | Bracco Ind Chimica Spa | |
| DE2852094A1 (de) * | 1978-11-30 | 1980-06-12 | Schering Ag | Neue roentgenkontrastmittel |
| JPS60183699A (ja) * | 1984-03-01 | 1985-09-19 | 株式会社東芝 | 異常警報装置の制御回路 |
| US4826689A (en) * | 1984-05-21 | 1989-05-02 | University Of Rochester | Method for making uniformly sized particles from water-insoluble organic compounds |
| US4783484A (en) * | 1984-10-05 | 1988-11-08 | University Of Rochester | Particulate composition and use thereof as antimicrobial agent |
| JPH0259997U (en, 2012) * | 1988-10-25 | 1990-05-01 | ||
| US6331640B1 (en) | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| US6265610B1 (en) * | 1999-01-12 | 2001-07-24 | The University Of North Carolina At Chapel Hill | Contrast media for angiography |
| JP2008526282A (ja) * | 2004-12-30 | 2008-07-24 | シンベンション アーゲー | シグナル供給剤、インプラント材料および薬剤を含む組み合わせ |
| CA2591942A1 (en) * | 2005-01-13 | 2006-07-20 | Cinvention Ag | Composite materials containing carbon nanoparticles |
| BRPI0606486A2 (pt) * | 2005-01-24 | 2009-06-30 | Cinv Ag | materiais compósitos contendo metal |
| CA2598840A1 (en) * | 2005-03-18 | 2006-09-21 | Cinvention Ag | Process for the preparation of porous sintered metal materials |
| AU2006265196A1 (en) * | 2005-07-01 | 2007-01-11 | Cinvention Ag | Medical devices comprising a reticulated composite material |
| EA200800196A1 (ru) * | 2005-07-01 | 2008-06-30 | Синвеншен Аг | Способ изготовления пористого композиционного материала |
| EP1937753A1 (en) * | 2005-10-18 | 2008-07-02 | Cinvention Ag | Thermoset particles and methods for production thereof |
| EP2104473A1 (en) * | 2007-01-19 | 2009-09-30 | Cinvention Ag | Porous, non-degradable implant made by powder molding |
| EP2126040A1 (en) * | 2007-02-28 | 2009-12-02 | Cinvention Ag | High surface cultivation system |
| WO2008104599A1 (en) * | 2007-02-28 | 2008-09-04 | Cinvention Ag | High surface cultivation system bag |
| CN101820923A (zh) * | 2007-10-12 | 2010-09-01 | 通用电气医疗集团股份有限公司 | 对比剂 |
| US8737669B2 (en) | 2011-07-28 | 2014-05-27 | Bose Corporation | Earpiece passive noise attenuating |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680133A (en) * | 1951-08-24 | 1954-06-01 | Mallinckrodt Chemical Works | Iodine-containing amino-benzoyl derivatives of amino acids |
| US3541141A (en) * | 1967-06-29 | 1970-11-17 | Squibb & Sons Inc | Bis-triiodoisophthalamic acid compounds |
| US3853866A (en) * | 1967-07-13 | 1974-12-10 | Oesterr Stickstoffwerke Ag | 3-amino-2,4,6-triiodobenzoic acid derivatives |
| US3660469A (en) * | 1969-08-04 | 1972-05-02 | Squibb & Sons Inc | Bis-triiodoisophthalamic acid compounds |
| BE795555A (fr) * | 1972-02-16 | 1973-08-16 | Schering Ag | Amides de triiodo-isophtaloyl-monoamino-acide, leur procede de preparation et leur utilisation |
-
1974
- 1974-05-31 GB GB24169/74A patent/GB1488903A/en not_active Expired
-
1975
- 1975-01-01 AR AR259006A patent/AR205196A1/es active
- 1975-05-15 ZA ZA00753131A patent/ZA753131B/xx unknown
- 1975-05-20 US US05/579,280 patent/US4005188A/en not_active Expired - Lifetime
- 1975-05-20 CH CH644875A patent/CH597159A5/xx not_active IP Right Cessation
- 1975-05-22 FR FR7515954A patent/FR2272655B1/fr not_active Expired
- 1975-05-23 NO NO751825A patent/NO139918C/no unknown
- 1975-05-28 ES ES437997A patent/ES437997A1/es not_active Expired
- 1975-05-28 HU HU75GU331A patent/HU176251B/hu unknown
- 1975-05-28 BE BE156776A patent/BE829573A/xx not_active IP Right Cessation
- 1975-05-28 DK DK239175AA patent/DK137945B/da unknown
- 1975-05-28 HU HU75GU317A patent/HU174153B/hu unknown
- 1975-05-28 BE BE156777A patent/BE829574A/xx not_active IP Right Cessation
- 1975-05-28 AT AT409875A patent/AT345796B/de not_active IP Right Cessation
- 1975-05-28 ES ES437996A patent/ES437996A1/es not_active Expired
- 1975-05-29 SE SE7506127A patent/SE410849B/xx unknown
- 1975-05-29 NL NL7506400A patent/NL7506400A/xx not_active Application Discontinuation
- 1975-05-29 CS CS753782A patent/CS207562B2/cs unknown
- 1975-05-30 BR BR4362/75D patent/BR7503406A/pt unknown
- 1975-05-30 DE DE19752524059 patent/DE2524059A1/de not_active Withdrawn
- 1975-05-30 CA CA228,142A patent/CA1071228A/en not_active Expired
- 1975-05-30 SU SU752144452A patent/SU665797A3/ru active
- 1975-05-30 JP JP50065216A patent/JPS585186B2/ja not_active Expired
- 1975-05-31 EG EG316/75A patent/EG12474A/xx active
-
1976
- 1976-12-14 SU SU762430497A patent/SU652884A3/ru active
-
1978
- 1978-06-13 SU SU782624999A patent/SU805944A3/ru active
- 1978-10-13 SU SU782671704A patent/SU1024006A3/ru active
-
1982
- 1982-06-16 JP JP57103698A patent/JPS584754A/ja active Pending
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |