DD238970A5 - Verfahren zur herstellung von iodierten triaminobenzen-verbindungen - Google Patents
Verfahren zur herstellung von iodierten triaminobenzen-verbindungen Download PDFInfo
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- DD238970A5 DD238970A5 DD85281566A DD28156685A DD238970A5 DD 238970 A5 DD238970 A5 DD 238970A5 DD 85281566 A DD85281566 A DD 85281566A DD 28156685 A DD28156685 A DD 28156685A DD 238970 A5 DD238970 A5 DD 238970A5
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- DD
- German Democratic Republic
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- formula
- compounds
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- temperature
- triiodo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000010933 acylation Effects 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 7
- 150000003936 benzamides Chemical class 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000002872 contrast media Substances 0.000 abstract description 7
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- 229940039231 contrast media Drugs 0.000 abstract description 2
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- 239000000243 solution Substances 0.000 description 49
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 27
- 239000011630 iodine Substances 0.000 description 24
- 229910052740 iodine Inorganic materials 0.000 description 24
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- 239000002244 precipitate Substances 0.000 description 14
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical group NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- 238000004587 chromatography analysis Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 230000026045 iodination Effects 0.000 description 5
- 238000006192 iodination reaction Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BZOWQNVPWVLNKD-UHFFFAOYSA-N 2-methoxy-n-[2,4,6-triiodo-3,5-bis[(2-methoxyacetyl)amino]phenyl]acetamide Chemical compound COCC(=O)NC1=C(I)C(NC(=O)COC)=C(I)C(NC(=O)COC)=C1I BZOWQNVPWVLNKD-UHFFFAOYSA-N 0.000 description 3
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 3
- DFWXYHZQNLIBLY-UHFFFAOYSA-N 5-nitrobenzene-1,3-diamine Chemical compound NC1=CC(N)=CC([N+]([O-])=O)=C1 DFWXYHZQNLIBLY-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VTUDWKBFGHYLQD-UHFFFAOYSA-N N-(3-acetamido-5-amino-2,4,6-triiodophenyl)acetamide Chemical compound C(C)(=O)NC=1C(=C(N)C(=C(C=1I)NC(C)=O)I)I VTUDWKBFGHYLQD-UHFFFAOYSA-N 0.000 description 3
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- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
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- YEUAPBRQESJLLW-UHFFFAOYSA-N 3,5-diacetamido-2,4,6-triiodobenzamide Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(N)=O)=C1I YEUAPBRQESJLLW-UHFFFAOYSA-N 0.000 description 2
- SVZMDJJCFHWLRI-UHFFFAOYSA-N 3,5-diamino-2,4,6-triiodobenzamide Chemical compound NC(=O)C1=C(I)C(N)=C(I)C(N)=C1I SVZMDJJCFHWLRI-UHFFFAOYSA-N 0.000 description 2
- UUKWKUSGGZNXGA-UHFFFAOYSA-N 3,5-dinitrobenzamide Chemical compound NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UUKWKUSGGZNXGA-UHFFFAOYSA-N 0.000 description 2
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 2
- ZCRNIIJXDRYWDU-UHFFFAOYSA-N 3-(methoxycarbonyl)-5-nitrobenzoic acid Chemical compound COC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 ZCRNIIJXDRYWDU-UHFFFAOYSA-N 0.000 description 2
- IBUKQAXCRVJPHF-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarboxamide Chemical compound CC(=O)NC1=C(I)C(C(N)=O)=C(I)C(C(N)=O)=C1I IBUKQAXCRVJPHF-UHFFFAOYSA-N 0.000 description 2
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- NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 2
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- MBVDTIMAKWGWBU-UHFFFAOYSA-N [1-oxo-1-[2,4,6-triiodo-3,5-bis[(2-methoxyacetyl)amino]anilino]propan-2-yl] acetate Chemical compound COCC(=O)NC1=C(I)C(NC(=O)COC)=C(I)C(NC(=O)C(C)OC(C)=O)=C1I MBVDTIMAKWGWBU-UHFFFAOYSA-N 0.000 description 2
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- 235000019341 magnesium sulphate Nutrition 0.000 description 2
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- NTUGHKBFDCJJIQ-UHFFFAOYSA-N IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(COC)=O Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(COC)=O NTUGHKBFDCJJIQ-UHFFFAOYSA-N 0.000 description 1
- UPOCHRGBAYXOLH-UHFFFAOYSA-N IC1=C(C(=C(C(=C1N(C(C)=O)CCOCCO)I)N(C(C)=O)CCOCCO)I)N(C(C)=O)CCOCCO Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CCOCCO)I)N(C(C)=O)CCOCCO)I)N(C(C)=O)CCOCCO UPOCHRGBAYXOLH-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
- 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 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OEZZSLPHYRNCQP-UHFFFAOYSA-N N-[3,5-bis[acetyl(2,3-dihydroxypropyl)amino]-2,4,6-triiodophenyl]-2-hydroxypropanamide Chemical compound IC1=C(C(=C(C(=C1N(C(C)=O)CC(CO)O)I)N(C(C)=O)CC(CO)O)I)NC(C(C)O)=O OEZZSLPHYRNCQP-UHFFFAOYSA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- RAIVLFPWSORAOZ-UHFFFAOYSA-N [1-[3-(2-acetyloxypropanoylamino)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]anilino]-1-oxopropan-2-yl] acetate Chemical compound COCC(=O)NC1=C(I)C(NC(=O)C(C)OC(C)=O)=C(I)C(NC(=O)C(C)OC(C)=O)=C1I RAIVLFPWSORAOZ-UHFFFAOYSA-N 0.000 description 1
- XVDLQYVFRPQSGC-UHFFFAOYSA-N [1-[3-(2-acetyloxypropanoylamino)-5-nitroanilino]-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)C(=O)NC1=CC(NC(=O)C(C)OC(C)=O)=CC([N+]([O-])=O)=C1 XVDLQYVFRPQSGC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- HTLANHFPYJMFEN-UHFFFAOYSA-N n-[3,5-bis[2,3-dihydroxypropyl-(2-methoxyacetyl)amino]-2,4,6-triiodophenyl]-n-(2,3-dihydroxypropyl)-2-methoxyacetamide Chemical compound COCC(=O)N(CC(O)CO)C1=C(I)C(N(CC(O)CO)C(=O)COC)=C(I)C(N(CC(O)CO)C(=O)COC)=C1I HTLANHFPYJMFEN-UHFFFAOYSA-N 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002330 subarachnoid space Anatomy 0.000 description 1
- GRNVJAJGRSXFFZ-UHFFFAOYSA-N sulfurous acid;hydrate Chemical compound O.OS(O)=O GRNVJAJGRSXFFZ-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Led Devices (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8415494A FR2571367B1 (fr) | 1984-10-09 | 1984-10-09 | Composes triaminobenzeniques iodes et/ou bromes, leur procede de preparation et leur application dans des produits de contraste |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD238970A5 true DD238970A5 (de) | 1986-09-10 |
Family
ID=9308495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85281566A DD238970A5 (de) | 1984-10-09 | 1985-10-09 | Verfahren zur herstellung von iodierten triaminobenzen-verbindungen |
Country Status (15)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863714A (en) * | 1987-02-05 | 1989-09-05 | Cook Imaging Corporation | Sterilization of compositions of limited stability |
| ES2021944A6 (es) * | 1990-02-14 | 1991-11-16 | Rhone Poulenc Farma Sa | Procedimiento para preparar nuevos derivados de 1,3,5,-triamino-2,4,6-triyodobenceno. |
| PT1829565E (pt) | 2001-12-20 | 2010-04-26 | Bone Support Ab | Novo substituto mineral de osso |
| CN101190888B (zh) * | 2006-11-24 | 2011-01-19 | 浙江尖峰海洲制药有限公司 | 5-乙酰氨基-2,4,6-三碘-1,3-苯二甲酰胺的制备方法 |
| EP2245003A2 (en) * | 2008-02-27 | 2010-11-03 | GE Healthcare AS | Contrast agents |
| US20110008263A1 (en) * | 2008-02-27 | 2011-01-13 | Hanno Priebe | Contrast agents |
| WO2010060941A2 (en) * | 2008-11-27 | 2010-06-03 | Ge Healthcare As | Contrast agents |
| US10610366B2 (en) | 2015-01-29 | 2020-04-07 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
| US10639157B2 (en) | 2017-03-14 | 2020-05-05 | Theracell, Inc. | Demineralized bone fiber composition for use in minimally invasive surgery |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2313917A1 (fr) * | 1975-06-10 | 1977-01-07 | Cortial | Nouveaux agents de contraste radiographique constitues par les derives de l'acide n-acetyl n-(diamino-3,5 triiodo-2,4,6 phenyl) b-aminopropionique, leurs intermediaires de synthese et leur preparation |
-
1984
- 1984-10-09 FR FR8415494A patent/FR2571367B1/fr not_active Expired
-
1985
- 1985-09-10 IL IL76354A patent/IL76354A0/xx unknown
- 1985-09-10 AU AU47200/85A patent/AU4720085A/en not_active Abandoned
- 1985-09-19 KR KR1019850006871A patent/KR860003202A/ko not_active Abandoned
- 1985-09-23 ZA ZA857277A patent/ZA857277B/xx unknown
- 1985-09-25 EP EP85401878A patent/EP0177414A1/fr not_active Withdrawn
- 1985-09-30 ES ES547411A patent/ES8604858A1/es not_active Expired
- 1985-10-04 FI FI853854A patent/FI853854A7/fi not_active Application Discontinuation
- 1985-10-07 CN CN198585107303A patent/CN85107303A/zh active Pending
- 1985-10-07 GR GR852421A patent/GR852421B/el unknown
- 1985-10-07 NO NO853953A patent/NO853953L/no unknown
- 1985-10-08 JP JP60224613A patent/JPS6191161A/ja active Pending
- 1985-10-08 HU HU853909A patent/HUT39718A/hu unknown
- 1985-10-08 DK DK459585A patent/DK459585A/da not_active Application Discontinuation
- 1985-10-09 DD DD85281566A patent/DD238970A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI853854L (fi) | 1986-04-10 |
| FI853854A7 (fi) | 1986-04-10 |
| GR852421B (enrdf_load_stackoverflow) | 1986-02-10 |
| ES8604858A1 (es) | 1986-03-16 |
| IL76354A0 (en) | 1986-01-31 |
| NO853953L (no) | 1986-04-10 |
| ES547411A0 (es) | 1986-03-16 |
| DK459585D0 (da) | 1985-10-08 |
| CN85107303A (zh) | 1986-03-10 |
| DK459585A (da) | 1986-04-10 |
| FI853854A0 (fi) | 1985-10-04 |
| HUT39718A (en) | 1986-10-29 |
| AU4720085A (en) | 1986-04-17 |
| JPS6191161A (ja) | 1986-05-09 |
| KR860003202A (ko) | 1986-05-21 |
| FR2571367A1 (fr) | 1986-04-11 |
| FR2571367B1 (fr) | 1987-02-13 |
| ZA857277B (en) | 1986-05-28 |
| EP0177414A1 (fr) | 1986-04-09 |
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