PL96082B1 - Sposob wytwarzania nowych bis-/dwuhydroksypropyloamidow/kwasu 5-hydroksypropionyloamino-2,4,6-trojjodoizoftalowego - Google Patents
Sposob wytwarzania nowych bis-/dwuhydroksypropyloamidow/kwasu 5-hydroksypropionyloamino-2,4,6-trojjodoizoftalowego Download PDFInfo
- Publication number
- PL96082B1 PL96082B1 PL1975185427A PL18542775A PL96082B1 PL 96082 B1 PL96082 B1 PL 96082B1 PL 1975185427 A PL1975185427 A PL 1975185427A PL 18542775 A PL18542775 A PL 18542775A PL 96082 B1 PL96082 B1 PL 96082B1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- compound
- water
- bis
- hydroxypropionylamino
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 17
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- DNWSSZXZTVMPKC-UHFFFAOYSA-N n,n-dihydroxypropan-1-amine Chemical compound CCCN(O)O DNWSSZXZTVMPKC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- VACJHIUSZPBOOF-UHFFFAOYSA-N 3-aminopropane-1,1-diol Chemical class NCCC(O)O VACJHIUSZPBOOF-UHFFFAOYSA-N 0.000 claims description 3
- GMPOMLNJZPYPGR-UHFFFAOYSA-N [1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- AVFLTCSEHPBNBA-UHFFFAOYSA-N 5-(3-hydroxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound OCCC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I AVFLTCSEHPBNBA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000002872 contrast media Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 238000002601 radiography Methods 0.000 description 10
- 230000001988 toxicity Effects 0.000 description 9
- 231100000419 toxicity Toxicity 0.000 description 9
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 229940113088 dimethylacetamide Drugs 0.000 description 7
- 238000001990 intravenous administration Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 6
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 210000004204 blood vessel Anatomy 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- RDFJFVXMRYVOAC-UHFFFAOYSA-N methiodal Chemical compound OS(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-N 0.000 description 5
- 229960003695 methiodal Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 230000002485 urinary effect Effects 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- XSOADYCNAKXIEX-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolan-4-amine Chemical compound CC1(C)OCC(N)O1 XSOADYCNAKXIEX-UHFFFAOYSA-N 0.000 description 2
- DTZMSDADRKLCQE-RFMXWLSYSA-N 3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodo-n-[(2r,3r,4s,5r)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]benzamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO)=C1I DTZMSDADRKLCQE-RFMXWLSYSA-N 0.000 description 2
- KQIGMPWTAHJUMN-VKHMYHEASA-N 3-aminopropane-1,2-diol Chemical compound NC[C@H](O)CO KQIGMPWTAHJUMN-VKHMYHEASA-N 0.000 description 2
- MYWMLEMKOKPNAP-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I MYWMLEMKOKPNAP-UHFFFAOYSA-N 0.000 description 2
- FBJVWRITWDYUAC-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I FBJVWRITWDYUAC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- OJHAHQJRQIOCFK-UHFFFAOYSA-N azane;chloroform;methanol Chemical compound N.OC.ClC(Cl)Cl OJHAHQJRQIOCFK-UHFFFAOYSA-N 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 150000001470 diamides Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229960000554 metrizamide Drugs 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000007487 urography Methods 0.000 description 2
- ALHZEIINTQJLOT-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) acetate Chemical compound ClC(=O)C(C)OC(C)=O ALHZEIINTQJLOT-UHFFFAOYSA-N 0.000 description 1
- VDRNKZIGPGTVPV-UHFFFAOYSA-N (2-acetyloxy-3-chloro-3-oxopropyl) acetate Chemical compound CC(=O)OCC(C(Cl)=O)OC(C)=O VDRNKZIGPGTVPV-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-GSVOUGTGSA-N (2r)-3-aminopropane-1,2-diol Chemical compound NC[C@@H](O)CO KQIGMPWTAHJUMN-GSVOUGTGSA-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
- WXLJJIHGDBUBJM-UHFFFAOYSA-N 1,3,5-triiodobenzene Chemical class IC1=CC(I)=CC(I)=C1 WXLJJIHGDBUBJM-UHFFFAOYSA-N 0.000 description 1
- WMWMTXHVEPHGQU-UHFFFAOYSA-N 1-n,3-n-bis(2,3-dihydroxypropyl)-5-(2-hydroxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(O)C(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I WMWMTXHVEPHGQU-UHFFFAOYSA-N 0.000 description 1
- ADLFBRNPQMLXTQ-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxan-5-amine Chemical compound CC1(C)OCC(N)CO1 ADLFBRNPQMLXTQ-UHFFFAOYSA-N 0.000 description 1
- FQAXLTARZOJBPJ-UHFFFAOYSA-N 2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=C(I)C=C(I)C(C(Cl)=O)=C1I FQAXLTARZOJBPJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- GLIODNATPFPVFB-UHFFFAOYSA-N 5-(2-acetyloxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)OC(C)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GLIODNATPFPVFB-UHFFFAOYSA-N 0.000 description 1
- GOCIYSIBXXQUAW-UHFFFAOYSA-N 5-(2-hydroxypropanoylamino)-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(O)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GOCIYSIBXXQUAW-UHFFFAOYSA-N 0.000 description 1
- GLIODNATPFPVFB-VKHMYHEASA-N 5-[[(2s)-2-acetyloxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GLIODNATPFPVFB-VKHMYHEASA-N 0.000 description 1
- GOCIYSIBXXQUAW-REOHCLBHSA-N 5-[[(2s)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GOCIYSIBXXQUAW-REOHCLBHSA-N 0.000 description 1
- DXWYUSQVAQEXFJ-UHFFFAOYSA-N 5-iodobenzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC(I)=CC(C(Cl)=O)=C1 DXWYUSQVAQEXFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- BOICGADXWRVKJG-UHFFFAOYSA-N azane;ethanol;ethyl acetate Chemical group N.CCO.CCOC(C)=O BOICGADXWRVKJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- OWXDZWFSRKSTTC-UHFFFAOYSA-N butanoic acid chloroform hexane Chemical compound ClC(Cl)Cl.CCCCCC.CCCC(O)=O OWXDZWFSRKSTTC-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000002585 cerebral angiography Methods 0.000 description 1
- 210000004289 cerebral ventricle Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- FDGDRDDFTVNCGU-UHFFFAOYSA-N iodomethanesulfonamide Chemical compound NS(=O)(=O)CI FDGDRDDFTVNCGU-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical class CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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 |
|---|---|---|---|
| CH1658874A CH608189A5 (OSRAM) | 1974-12-13 | 1974-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL96082B1 true PL96082B1 (pl) | 1977-12-31 |
Family
ID=4418593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975185427A PL96082B1 (pl) | 1974-12-13 | 1975-12-10 | Sposob wytwarzania nowych bis-/dwuhydroksypropyloamidow/kwasu 5-hydroksypropionyloamino-2,4,6-trojjodoizoftalowego |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4001323A (OSRAM) |
| JP (1) | JPS5182236A (OSRAM) |
| AR (1) | AR211853A1 (OSRAM) |
| AT (2) | AT340582B (OSRAM) |
| AU (1) | AU475785B2 (OSRAM) |
| BE (1) | BE836355A (OSRAM) |
| BG (1) | BG26512A3 (OSRAM) |
| CA (1) | CA1046082A (OSRAM) |
| CH (1) | CH608189A5 (OSRAM) |
| CS (1) | CS194234B2 (OSRAM) |
| DD (1) | DD122475A5 (OSRAM) |
| DK (1) | DK147336C (OSRAM) |
| ES (1) | ES442651A1 (OSRAM) |
| FR (1) | FR2293919A1 (OSRAM) |
| GB (1) | GB1472050A (OSRAM) |
| HU (1) | HU170216B (OSRAM) |
| IE (1) | IE42620B1 (OSRAM) |
| IL (1) | IL48484A (OSRAM) |
| IN (1) | IN142089B (OSRAM) |
| MX (1) | MX3174E (OSRAM) |
| NL (1) | NL157295B (OSRAM) |
| NO (1) | NO145096C (OSRAM) |
| PH (1) | PH12321A (OSRAM) |
| PL (1) | PL96082B1 (OSRAM) |
| RO (1) | RO69615A (OSRAM) |
| SE (1) | SE409993B (OSRAM) |
| SU (1) | SU628813A3 (OSRAM) |
| YU (2) | YU40448B (OSRAM) |
| ZA (1) | ZA757222B (OSRAM) |
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| JPS52130923A (en) * | 1976-04-27 | 1977-11-02 | Mallinckrodt Chemical Works | Xxray photographic agent |
| GB1548594A (en) * | 1976-06-11 | 1979-07-18 | Nyegaard & Co As | Triiodoisophthalic acid amides |
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| US4256729A (en) * | 1979-03-23 | 1981-03-17 | Mallinckrodt, Inc. | N,N'-Bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-keto-L-gulonamido)isophthalamide and radiological compositions containing same |
| NL8002388A (nl) * | 1979-05-21 | 1980-11-25 | Mallinckrodt Inc | Roentgencontrastmiddel. |
| IT1207226B (it) * | 1979-08-09 | 1989-05-17 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico, metodo per la loro preparazione e mezzi di contrasto che li contengono. |
| 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 |
| DE3038853A1 (de) | 1980-10-10 | 1982-05-27 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue n-hydroxy-alkylierte dicarbonsaeure-bis-(3,5-dicarbamoyl-2,4,6-trijodanilide), deren herstellung und diese enthaltende roentgenkonstrastmittel (ii) |
| DE3150916A1 (de) * | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | N-hydroxyaethylierte 2,4,6-trijodaminoisiophthalsaeure-bis- trihydroxybutylamide, deren herstellung und diese enthaltende roentgenkontrastmittel" |
| DE3150917A1 (de) * | 1981-12-18 | 1983-06-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | "2-amino-1-(1,3-dioxolan-4-yl)-ethanol-verbindungen, deren herstellung und verwendung zur weiterverarbeitung" |
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| DE3937118A1 (de) * | 1989-11-03 | 1991-05-08 | Schering Ag | Nichtionische roentgenkontrastmittel mit hohem jodgehalt |
| US5232685A (en) * | 1989-11-03 | 1993-08-03 | Schering Aktiengesellschaft | Nonionic x-ray contrast medium with high iodine content |
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| US5169864A (en) * | 1991-11-15 | 1992-12-08 | Baxter International Inc. | Unbuffered premixed ranitidine formulation |
| 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 |
| IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1256163B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
| IT1256248B (it) * | 1992-12-24 | 1995-11-29 | Bracco Spa | Formulazioni iniettabili acquose per radiodiagnostica comprendenti miscele di composti aromatici iodurati utili come agenti opacizzanti ai raggi x |
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| IT1275429B (it) * | 1995-05-18 | 1997-08-07 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di composti organici |
| DE69601525T2 (de) * | 1995-05-23 | 1999-06-24 | Fructamine S.P.A., Mozzo | Verfahren zur herstellung von dicarbonsäurechlorid |
| KR100269080B1 (ko) * | 1995-05-23 | 2000-10-16 | 안토니오 칸탈루피 | 디카르복실산디클로라이드의제조방법 |
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| JP4070235B2 (ja) * | 1995-09-08 | 2008-04-02 | ブラッコ・インテルナツィオナル・ベーヴェー | （ｓ）−ｎ，ｎ’−ビス［２−ヒドロキシ−１−（ヒドロキシメチル）エチル］−５−［（２−ヒドロキシ−１−オキソプロピル）アミノ］−２，４，６−トリヨード−１，３−ベンゼンジカルボキサアミドの、水からの結晶化方法 |
| JP4104656B2 (ja) * | 1995-12-19 | 2008-06-18 | ブラッコ・リサーチ・ソシエテ・アノニム | トリヨードベンゼンポリマーからなる胃腸管の画像形成用組成物 |
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| IT1288114B1 (it) * | 1996-06-13 | 1998-09-10 | Fructamine Spa | Processo per la purificazione di un intermedio |
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| US5705692A (en) * | 1996-09-27 | 1998-01-06 | Abbott Laboratories | Process for the preparation of iohexol |
| US5861138A (en) * | 1996-11-20 | 1999-01-19 | Hoechst Celanese Corp. | Ligands for MRI contrast agent |
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| IT1289519B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| IT1289520B1 (it) * | 1996-12-24 | 1998-10-15 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
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| JP4080545B2 (ja) * | 1997-02-11 | 2008-04-23 | ブラッコ・インテルナツイオナル・ベーヴェー | （ｓ）−ｎ，ｎ′−ビス［２−ヒドロキシ−１−（ヒドロキシメチル）エチル］−５−［（２−ヒドロキシ−１−オキソプロピル）アミノ］−２，４，６−トリヨード−１，３−ベンゼンジカルボキシアミドを直鎖状または分岐状の（ｃ５〜ｃ６）アルコールまたはそれらの混合物から結晶化させる方法 |
| IT1292037B1 (it) * | 1997-05-30 | 1999-01-25 | Bracco Spa | Processo per la preparazione di 5-(acetil 62,3-diidrossipropil)- ammino)-n,n'-bis(2,3-diidrossipropil)-2,4,6-triiodo-1,3-benzen- |
| US5820851A (en) * | 1997-08-21 | 1998-10-13 | Hoechst Celanese Corporation | Tripodal pyridine ligands as MRI contrast agents |
| US5858329A (en) * | 1997-08-21 | 1999-01-12 | Hoechst Celanese Corporation | MRI diagnostic procedures using tripodal pyridinyl metal complexes |
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| IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| US6262303B1 (en) | 1998-05-08 | 2001-07-17 | Dibra S.P.A. | Process for the preparation of S-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)-amino]-2,4,6-triiodo-1,3-benzenedicarboxamide |
| IT1302200B1 (it) * | 1998-09-11 | 2000-07-31 | Dibra Spa | PROCESSO PER LA PREPARAZIONE DELLA S-N,N'-BIS°2-IDROSSI-1-(IDROSSIMETIL)ETILé-5-°(2-IDROSSI-1- |
| GB9825095D0 (en) | 1998-11-16 | 1999-01-13 | Nycomed Imaging As | Chemical process |
| US6803485B2 (en) | 1999-02-26 | 2004-10-12 | Bracco Imaging S.P.A. | Process for the preparation of iopamidol |
| SE520688C2 (sv) * | 2000-04-11 | 2003-08-12 | Bone Support Ab | Ett injicerbart ersättningsmaterial för benmineral |
| SE517168C2 (sv) * | 2000-07-17 | 2002-04-23 | Bone Support Ab | En komposition för ett injicerbart ersättningsmaterial för benmineral |
| WO2002051301A2 (en) | 2000-11-10 | 2002-07-04 | Wm. Marsh Rice University | Fullerene (c60)-based x-ray contrast agent for diagnostic imaging |
| IT1319671B1 (it) * | 2000-12-01 | 2003-10-23 | Bracco Spa | Processo per la preparazione di (s)-n,n'-bis(2-idrossi-1-(idrossimetil)etil)-5-((2-idrossi-1-ossopropil)ammino) |
| SE522098C2 (sv) * | 2001-12-20 | 2004-01-13 | Bone Support Ab | Ett nytt benmineralsubstitut |
| SE0300620D0 (sv) * | 2003-03-05 | 2003-03-05 | Bone Support Ab | A new bone substitute composition |
| SE0302983D0 (sv) * | 2003-11-11 | 2003-11-11 | Bone Support Ab | Anordning för att förse spongiöst ben med benersättnings- och/eller benförstärkningsmaterial och förfarande i samband därmed |
| SE527528C2 (sv) * | 2004-06-22 | 2006-04-04 | Bone Support Ab | Anordning för framställning av härdbar massa samt användning av anordningen |
| EP1836239B1 (en) | 2005-01-13 | 2008-10-29 | Cinvention Ag | Composite materials containing carbon nanoparticles |
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| US7955234B1 (en) | 2007-02-28 | 2011-06-07 | Pursley Michael G | Exercise device and method |
| EP2093206A1 (en) | 2008-02-20 | 2009-08-26 | BRACCO IMAGING S.p.A. | Process for the iodination of aromatic compounds |
| BRPI0921464B8 (pt) * | 2008-11-18 | 2021-05-25 | Bracco Imaging Spa | processo para preparação de agente de contraste iodado |
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| EP2230227A1 (en) * | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
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| RU2528402C2 (ru) | 2009-07-07 | 2014-09-20 | Бракко Имэджинг Спа | Способ получения йодирующего агента |
| US9180137B2 (en) | 2010-02-09 | 2015-11-10 | Bone Support Ab | Preparation of bone cement compositions |
| PT105770B (pt) * | 2011-06-24 | 2013-07-08 | Hovione Farmaciencia S A | Novo intermediário e seu uso na preparação de agente de contrate triiodado |
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| EP2958603B1 (en) | 2013-02-20 | 2018-03-28 | Bone Support AB | Improved setting of hardenable bone substitute |
| RU2530159C1 (ru) * | 2013-04-16 | 2014-10-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "САНКТ-ПЕТЕРБУРГСКАЯ ГОСУДАРСТВЕННАЯ АКАДЕМИЯ ВЕТЕРИНАРНОЙ МЕДИЦИНЫ" (ФГБОУ ВПО СПБГАВМ) | Способ изготовления рентгеноконтрастной массы для вазорентгенографии при посмертных исследованиях животных |
| MX380203B (es) * | 2013-11-05 | 2025-03-12 | Bracco Imaging Spa | Procedimiento para la preparación de iopamidol. |
| JP6546609B2 (ja) | 2014-06-10 | 2019-07-17 | ブラッコ・イメージング・ソシエタ・ペル・アチオニＢｒａｃｃｏ Ｉｍａｇｉｎｇ Ｓ．Ｐ．Ａ． | （ｓ）−２−アセチルオキシプロピオン酸およびその誘導体の製造方法 |
| CN104230731B (zh) * | 2014-09-24 | 2016-01-20 | 武汉理工大学 | 造影剂中间体三碘异酞酰氯的制备方法 |
| PT108524B (pt) | 2015-06-02 | 2017-12-15 | Hovione Farmaciência S A | Processo para a preparação de intermediários úteis na preparação de agentes de contraste não-iónicos |
| CN105461581A (zh) * | 2015-11-17 | 2016-04-06 | 浙江海洲制药有限公司 | 碘帕醇杂质a和杂质b的合成方法 |
| CN107778191A (zh) * | 2016-08-26 | 2018-03-09 | 正大天晴药业集团股份有限公司 | 一种碘普罗胺及其中间体的制备方法 |
| US10836710B2 (en) * | 2016-12-05 | 2020-11-17 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
| CA3058852A1 (en) | 2017-06-07 | 2018-12-13 | Bracco Imaging Spa | Process for recovery of iodine from aqueous solutions |
| US20240199530A1 (en) | 2021-03-22 | 2024-06-20 | Bracco Imaging S.P.A. | Industrial synthesis of serinol |
| CN118414325A (zh) | 2021-12-20 | 2024-07-30 | 伯拉考成像股份公司 | 制备2,4,6-三碘间苯二甲酸双酰胺的方法 |
| CN116063195A (zh) * | 2023-01-07 | 2023-05-05 | 安庆朗坤药业有限公司 | 一种碘帕醇中间体碘化物的制备方法 |
| WO2024256322A1 (en) | 2023-06-13 | 2024-12-19 | Bracco Imaging Spa | Synthesis of non-ionic radiographic contrast agents by means of reactive extrusion |
| EP4534526A1 (en) | 2023-10-04 | 2025-04-09 | Bracco Imaging SPA | Optimized process for the preparation of iopamidol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1047908B (it) * | 1969-06-27 | 1980-10-20 | Nyegaard & Co As | Procedimento per preparare agenti di contrasto per raggi x a base di alcanoli |
| DE2124904C3 (de) * | 1971-05-15 | 1980-09-18 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Hydroxy- und Alkoxyacetamido-trijodbenzoesäuren, deren Salze mit physiologisch verträglichen Basen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel |
| BE788054A (fr) * | 1971-08-26 | 1973-02-26 | Bracco Ind Chimica Spa | Nouvel agent de contraste radiographique et procede pour le preparer |
| CH576256A5 (OSRAM) * | 1973-07-17 | 1976-06-15 | Bracco Ind Chimica Spa | |
| CH583562A5 (OSRAM) * | 1973-07-17 | 1977-01-14 | Bracco Ind Chimica Spa |
-
1974
- 1974-12-13 CH CH1658874A patent/CH608189A5/xx active Protection Beyond IP Right Term
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1975
- 1975-10-17 NL NL7512208.A patent/NL157295B/xx not_active IP Right Cessation
- 1975-11-11 BG BG031456A patent/BG26512A3/xx unknown
- 1975-11-14 ES ES442651A patent/ES442651A1/es not_active Expired
- 1975-11-17 IL IL48484A patent/IL48484A/xx unknown
- 1975-11-18 ZA ZA757222A patent/ZA757222B/xx unknown
- 1975-11-24 US US05/634,836 patent/US4001323A/en not_active Expired - Lifetime
- 1975-11-25 IN IN2245/CAL/75A patent/IN142089B/en unknown
- 1975-11-26 CA CA240,580A patent/CA1046082A/en not_active Expired
- 1975-11-26 GB GB4862075A patent/GB1472050A/en not_active Expired
- 1975-12-02 AR AR261439A patent/AR211853A1/es active
- 1975-12-03 MX MX004201U patent/MX3174E/es unknown
- 1975-12-05 AT AT925075A patent/AT340582B/de not_active IP Right Cessation
- 1975-12-05 BE BE162511A patent/BE836355A/xx not_active IP Right Cessation
- 1975-12-10 SU SU752196656A patent/SU628813A3/ru active
- 1975-12-10 HU HUSA2864A patent/HU170216B/hu unknown
- 1975-12-10 PL PL1975185427A patent/PL96082B1/pl unknown
- 1975-12-11 DD DD190060A patent/DD122475A5/xx unknown
- 1975-12-11 FR FR7537934A patent/FR2293919A1/fr active Granted
- 1975-12-11 IE IE2706/75A patent/IE42620B1/en active Protection Beyond IP Right Term
- 1975-12-12 DK DK567475A patent/DK147336C/da not_active IP Right Cessation
- 1975-12-12 YU YU3155/75A patent/YU40448B/xx unknown
- 1975-12-12 AU AU87516/75A patent/AU475785B2/en not_active Expired
- 1975-12-12 NO NO754241A patent/NO145096C/no unknown
- 1975-12-12 JP JP50147492A patent/JPS5182236A/ja active Granted
- 1975-12-12 SE SE7514076A patent/SE409993B/xx not_active IP Right Cessation
- 1975-12-12 RO RO7584187A patent/RO69615A/ro unknown
- 1975-12-12 CS CS758475A patent/CS194234B2/cs unknown
- 1975-12-15 PH PH7517872A patent/PH12321A/en unknown
- 1975-12-22 AT AT925175A patent/AT342579B/de not_active IP Right Cessation
-
1983
- 1983-09-30 YU YU1967/83A patent/YU41540B/xx unknown
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