DD205892A5 - Verfahren zur herstellung von in kontrastmitteln verwendbaren brom-verbindungen - Google Patents
Verfahren zur herstellung von in kontrastmitteln verwendbaren brom-verbindungen Download PDFInfo
- Publication number
- DD205892A5 DD205892A5 DD82242886A DD24288682A DD205892A5 DD 205892 A5 DD205892 A5 DD 205892A5 DD 82242886 A DD82242886 A DD 82242886A DD 24288682 A DD24288682 A DD 24288682A DD 205892 A5 DD205892 A5 DD 205892A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- formula
- lower alkyl
- compounds
- hydrogen atom
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title description 21
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 59
- 238000002360 preparation method Methods 0.000 claims description 56
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 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 21
- 238000000034 method Methods 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 19
- -1 mono-substituted amino group Chemical group 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 14
- 230000005494 condensation Effects 0.000 claims description 14
- 230000010933 acylation Effects 0.000 claims description 11
- 238000005917 acylation reaction Methods 0.000 claims description 11
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 238000005755 formation reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 115
- 239000000047 product Substances 0.000 description 100
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- 239000000203 mixture Substances 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- 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 32
- 235000019253 formic acid Nutrition 0.000 description 32
- 201000000760 cerebral cavernous malformation Diseases 0.000 description 26
- 239000000725 suspension Substances 0.000 description 23
- 238000001035 drying Methods 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 239000005711 Benzoic acid Substances 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 239000002872 contrast media Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 229960004050 aminobenzoic acid Drugs 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZAENXHXQWSDUOG-UHFFFAOYSA-N benzene;iodine Chemical class [I].C1=CC=CC=C1 ZAENXHXQWSDUOG-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- CPWPJLJWUXOOAB-UHFFFAOYSA-N benzene;bromine Chemical class [Br].C1=CC=CC=C1 CPWPJLJWUXOOAB-UHFFFAOYSA-N 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- HUHDYASLFWQVOL-WZTVWXICSA-N 3-[[2-[[3-[acetyl(methyl)amino]-2,4,6-triiodo-5-(methylcarbamoyl)benzoyl]amino]acetyl]amino]-5-(2-hydroxyethylcarbamoyl)-2,4,6-triiodobenzoic acid;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I HUHDYASLFWQVOL-WZTVWXICSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WXUPOMXKMSVGDH-UHFFFAOYSA-N 3-amino-2,4,6-tribromobenzoic acid Chemical compound NC1=C(Br)C=C(Br)C(C(O)=O)=C1Br WXUPOMXKMSVGDH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 102100040141 Aminopeptidase O Human genes 0.000 description 3
- 108050008333 Aminopeptidase O Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 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 2
- 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
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 description 2
- CYIMWVBOEWSUGR-UHFFFAOYSA-N 2,4,6-tribromo-5-cyanobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=C(Br)C(C#N)=C(Br)C(C(O)=O)=C1Br CYIMWVBOEWSUGR-UHFFFAOYSA-N 0.000 description 2
- WFLIGSNGJSHVOE-UHFFFAOYSA-N 2,4,6-tribromobenzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=C(Br)C(C(Cl)=O)=C(Br)C(C(Cl)=O)=C1Br WFLIGSNGJSHVOE-UHFFFAOYSA-N 0.000 description 2
- KZQVUBUSVAUJCG-UHFFFAOYSA-N 2,4,6-tribromobenzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=C(Br)C(C(O)=O)=C(Br)C(C(O)=O)=C1Br KZQVUBUSVAUJCG-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- QSACCXVHEVWNMX-UHFFFAOYSA-N N-acetylanthranilic acid Chemical compound CC(=O)NC1=CC=CC=C1C(O)=O QSACCXVHEVWNMX-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 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 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000004768 bromobenzenes Chemical class 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229940029355 iodipamide Drugs 0.000 description 2
- 229940029407 ioxaglate Drugs 0.000 description 2
- 229960000554 metrizamide Drugs 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- RIWAPWDHHMWTRA-UHFFFAOYSA-N 1,2,3-triiodobenzene Chemical compound IC1=CC=CC(I)=C1I RIWAPWDHHMWTRA-UHFFFAOYSA-N 0.000 description 1
- ICNJONOMKVOFDD-UHFFFAOYSA-N 1-aminocyclohexa-3,5-diene-1,3-dicarboxylic acid Chemical compound OC(=O)C1(N)CC(C(O)=O)=CC=C1 ICNJONOMKVOFDD-UHFFFAOYSA-N 0.000 description 1
- FEBSOZAVIJECCY-UHFFFAOYSA-N 2,4,6-tribromo-5-carbamoylbenzene-1,3-dicarboxylic acid Chemical compound NC(=O)C1=C(Br)C(C(O)=O)=C(Br)C(C(O)=O)=C1Br FEBSOZAVIJECCY-UHFFFAOYSA-N 0.000 description 1
- LDOMKUVUXZRECL-UHFFFAOYSA-N 2-aminobenzene-1,3-dicarboxylic acid Chemical class NC1=C(C(O)=O)C=CC=C1C(O)=O LDOMKUVUXZRECL-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- UFOBTLFHOPRMLS-UHFFFAOYSA-N 5-amino-2,4,6-tribromobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(Br)C(C(Cl)=O)=C(Br)C(C(Cl)=O)=C1Br UFOBTLFHOPRMLS-UHFFFAOYSA-N 0.000 description 1
- KGKQFJKPOZCZLD-UHFFFAOYSA-N 5-amino-2,4,6-tribromobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(Br)C(C(O)=O)=C(Br)C(C(O)=O)=C1Br KGKQFJKPOZCZLD-UHFFFAOYSA-N 0.000 description 1
- GNOGSFBXBWBTIG-UHFFFAOYSA-N Acetrizoic acid Chemical compound CC(=O)NC1=C(I)C=C(I)C(C(O)=O)=C1I GNOGSFBXBWBTIG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CIUYNYYBYDJYKH-UHFFFAOYSA-N BrC1=C(C(=O)O)C(=CC(=C1N(C(C)=O)C(C)=O)Br)Br Chemical compound BrC1=C(C(=O)O)C(=CC(=C1N(C(C)=O)C(C)=O)Br)Br CIUYNYYBYDJYKH-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229960005216 acetrizoic acid Drugs 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000012631 diagnostic technique Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000008424 iodobenzenes Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 229960001707 ioxaglic acid Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UCPVOMHRDXMAIZ-UHFFFAOYSA-M sodium acetrizoate Chemical compound [Na+].CC(=O)NC1=C(I)C=C(I)C(C([O-])=O)=C1I UCPVOMHRDXMAIZ-UHFFFAOYSA-M 0.000 description 1
- 229950011473 sodium acetrizoate Drugs 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8116477A FR2512014A1 (fr) | 1981-08-28 | 1981-08-28 | Composes bromes utilisables dans des produits opacifiants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD205892A5 true DD205892A5 (de) | 1984-01-11 |
Family
ID=9261752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82242886A DD205892A5 (de) | 1981-08-28 | 1982-08-30 | Verfahren zur herstellung von in kontrastmitteln verwendbaren brom-verbindungen |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0073715A1 (enExample) |
| JP (1) | JPS5852244A (enExample) |
| AU (1) | AU8747382A (enExample) |
| DD (1) | DD205892A5 (enExample) |
| FR (1) | FR2512014A1 (enExample) |
| YU (1) | YU191382A (enExample) |
| ZA (1) | ZA826034B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2541272A1 (fr) * | 1983-02-23 | 1984-08-24 | Guerbet Sa | Composes bromes et produits opacifiants en contenant |
| US6472528B1 (en) | 1999-08-10 | 2002-10-29 | Neurocrine Biosciences, Inc. | Synthesis of substituted pyrazolopyrimidines |
| EP1344768B1 (en) * | 1999-08-10 | 2005-04-06 | Neurocrine Biosciences, Inc. | Synthesis of substituted pyrazolopyrimidines |
| EP1186305A1 (en) * | 2000-09-07 | 2002-03-13 | Schering Aktiengesellschaft | New brominated compounds as contrast media for X-ray mammography |
| WO2006100731A1 (ja) * | 2005-03-18 | 2006-09-28 | Manac Inc. | ５−アミノ−２，４，６−トリヨードイソフタル酸誘導体のアセチル化方法 |
| MX2014001623A (es) | 2011-08-10 | 2015-03-09 | Digna Biotech Sl | Uso de la cardiotofina-1 para el tratamiento de enfermedades renales. |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT129942B (de) * | 1929-09-25 | 1932-10-10 | Schering Kahlbaum Ag | Kontrastmittel für Röntgendurchleuchtungen. |
| NL74787C (enExample) * | 1950-11-13 | |||
| FR1088590A (fr) * | 1952-08-16 | 1955-03-08 | Schering Ag | Agents de contraste pour rayons x et leur préparation |
| DE1003743B (de) * | 1953-10-09 | 1957-03-07 | Frankfurter Arzneimittelfabrik | Verfahren zur Herstellung von 2,4,6-Tribrom-3-acetylamino-benzoesaeure |
| BE555768A (enExample) * | 1956-03-13 | |||
| BR6024559D0 (pt) * | 1959-12-08 | 1973-05-31 | Nyegaard & Co As | Processo para preparacao de novos derivados de acido 3 5-diamino-2 4 6-triiodo benzoico ou semi sais nao toxicos bem como de agentes ou meios de contraste para raios x baseados nos mesmos |
| DE1151811B (de) * | 1960-02-09 | 1963-07-25 | Bayer Ag | Verfahren zur Herstellung von im Kern bromierten Phenolen |
| FR2162M (fr) * | 1961-02-28 | 1963-11-25 | Nyegaard & Co As | Dérivés de n-alkylacylanilides, utiles, notamment comme agents de contraste pour rayons x. |
| US3290366A (en) * | 1963-03-06 | 1966-12-06 | Mallinckrodt Chemical Works | 5-amino-nu-alkyl-2, 4, 6-triiodoisophthalamic acid derivatives |
| FR2074734A1 (en) * | 1970-01-22 | 1971-10-08 | Guerbet Lab Andre | 3-(n-2-hydroxyethylcarbamyl)-5-(n-methylacetamido)2,4,6-triiodo- benz - acid - radiographic contrast agent |
| FR2085636B1 (enExample) * | 1970-04-15 | 1973-06-08 | Guerbet Lab Andre | |
| US3778190A (en) * | 1971-10-01 | 1973-12-11 | Gen Electric | Bucket cover attachment |
| GB1436357A (en) * | 1973-12-07 | 1976-05-19 | Laboraoires Andre Guerbet | Tri-iodo benzene derivatives and their use as x-ray contrast |
| AR207465A1 (es) * | 1974-05-31 | 1976-10-08 | Guerbet Lab Andre | Procedimiento de preparacion de derivados de acido triiodoi2,4,6-(triiodo-2,4,6-benzoil)-amino-alcanoilaminobenzoico de acido triiodo-2,4,6-(triiodo-2,4,6-(triiodo-2,4,6-benzoil)-aminoalcanoilaminobenzoil)-amino-alcanoil-aminobenzoico y de acido triiodo-2,4,6-bis((triiodo-2,4,6-fenil)-carbamoil-metil)-aminoalcanoil-aminobenzoico |
| DE3001292A1 (de) * | 1980-01-11 | 1981-07-16 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Nichtionische 5-c-substituierte 2,4,6-trijod-isophthalsaeure-derivate |
-
1981
- 1981-08-28 FR FR8116477A patent/FR2512014A1/fr active Granted
-
1982
- 1982-08-19 ZA ZA826034A patent/ZA826034B/xx unknown
- 1982-08-20 AU AU87473/82A patent/AU8747382A/en not_active Abandoned
- 1982-08-25 EP EP82401578A patent/EP0073715A1/fr not_active Withdrawn
- 1982-08-25 YU YU01913/82A patent/YU191382A/xx unknown
- 1982-08-28 JP JP57149832A patent/JPS5852244A/ja active Pending
- 1982-08-30 DD DD82242886A patent/DD205892A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU191382A (en) | 1985-06-30 |
| FR2512014A1 (fr) | 1983-03-04 |
| EP0073715A1 (fr) | 1983-03-09 |
| JPS5852244A (ja) | 1983-03-28 |
| AU8747382A (en) | 1983-03-03 |
| FR2512014B1 (enExample) | 1985-03-08 |
| ZA826034B (en) | 1984-03-28 |
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