NO129093B - - Google Patents

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Publication number: NO129093B
Authority: NO; Norway
Prior art keywords: groups; stated; triiodobenzoyl; group; acid
Prior art date: 1969-06-27

Application number

NO02518/70A

Other languages

English (en)

Norwegian (no)

Inventor

T Almen

J Haavaldsen

V Nordal

Original Assignee

Nyegaard & Co As

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1969-06-27

Filing date

1970-06-26

Publication date

1974-02-25

1970-06-26 Application filed by Nyegaard & Co As filed Critical Nyegaard & Co As

1974-02-25 Publication of NO129093B publication Critical patent/NO129093B/no

Links

150000001875 compounds Chemical class 0.000 claims description 54
239000002872 contrast media Substances 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 12
125000001931 aliphatic group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
229960002442 glucosamine Drugs 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000003172 aldehyde group Chemical group 0.000 claims description 8
238000000926 separation method Methods 0.000 claims description 7
230000005484 gravity Effects 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical class OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
229960001413 acetanilide Drugs 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 41
239000002253 acid Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
-1 alkali metal salts Chemical class 0.000 description 21
239000000047 product Substances 0.000 description 21
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
238000000034 method Methods 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
150000004820 halides Chemical class 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000003921 oil Substances 0.000 description 8
230000003204 osmotic effect Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
231100000419 toxicity Toxicity 0.000 description 8
230000001988 toxicity Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
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 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
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 5
150000007513 acids Chemical class 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
230000002526 effect on cardiovascular system Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000012800 visualization Methods 0.000 description 5
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000003957 anion exchange resin Substances 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
125000002768 hydroxyalkyl group Chemical group 0.000 description 4
239000005457 ice water Substances 0.000 description 4
238000006192 iodination reaction Methods 0.000 description 4
150000008040 ionic compounds Chemical class 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003513 alkali Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
210000000748 cardiovascular system Anatomy 0.000 description 3
210000001175 cerebrospinal fluid Anatomy 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
150000004292 cyclic ethers Chemical class 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
230000026045 iodination Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 description 2
SPYXCBRPFJVOTD-XKAARJIMSA-N 2,4,6-triiodo-n-methyl-n-[(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl]benzamide Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CN(C)C(=O)C1=C(I)C=C(I)C=C1I SPYXCBRPFJVOTD-XKAARJIMSA-N 0.000 description 2
HRMQJJGGCUYILB-UHFFFAOYSA-N 2,4,6-triiodobenzoyl chloride Chemical compound ClC(=O)C1=C(I)C=C(I)C=C1I HRMQJJGGCUYILB-UHFFFAOYSA-N 0.000 description 2
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
RSCMSACQRPYYRN-UHFFFAOYSA-N 3,5-diaminobenzamide Chemical compound NC(=O)C1=CC(N)=CC(N)=C1 RSCMSACQRPYYRN-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
230000021736 acetylation Effects 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003729 cation exchange resin Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229960001911 glucosamine hydrochloride Drugs 0.000 description 2
230000002140 halogenating effect Effects 0.000 description 2
238000003384 imaging method Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
150000008146 mannosides Chemical class 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
230000002792 vascular Effects 0.000 description 2
VQSVOQJUFSROBP-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(2-hydroxyethylamino)hexane-1,2,3,4,5-pentol Chemical compound OCCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO VQSVOQJUFSROBP-LXGUWJNJSA-N 0.000 description 1
XDIYNQZUNSSENW-RPQBYJBYSA-N (2s,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O XDIYNQZUNSSENW-RPQBYJBYSA-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
CRVYPNHLIAWRNV-UHFFFAOYSA-N 2,4,6-triiodobenzoic acid Chemical compound OC(=O)C1=C(I)C=C(I)C=C1I CRVYPNHLIAWRNV-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
SEJCXXXEYJMYKT-NCCMUGIUSA-N 3,5-diamino-2,4,6-triiodo-n-methyl-n-[(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl]benzamide Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CN(C)C(=O)C1=C(I)C(N)=C(I)C(N)=C1I SEJCXXXEYJMYKT-NCCMUGIUSA-N 0.000 description 1
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 1
NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 1
GGOPTDHVLCAOSV-UHFFFAOYSA-N 3-(diacetylamino)-2,4,6-triiodobenzoic acid Chemical compound CC(=O)N(C(C)=O)C1=C(I)C=C(I)C(C(O)=O)=C1I GGOPTDHVLCAOSV-UHFFFAOYSA-N 0.000 description 1
CPRGSOYWINBLDR-UHFFFAOYSA-N 3-amino-5-nitrobenzamide Chemical compound NC(=O)C1=CC(N)=CC([N+]([O-])=O)=C1 CPRGSOYWINBLDR-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZSBDPRIWBYHIAF-UHFFFAOYSA-N N-acetyl-acetamide Natural products CC(=O)NC(C)=O ZSBDPRIWBYHIAF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
XWFMOWRKOWOJJN-UHFFFAOYSA-N [Na].ClICl Chemical compound [Na].ClICl XWFMOWRKOWOJJN-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000011149 active material Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229940023913 cation exchange resins Drugs 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000011208 chromatographic data Methods 0.000 description 1
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229940125773 compound 10 Drugs 0.000 description 1
229940127271 compound 49 Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000005188 flotation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
125000003827 glycol group Chemical group 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000002609 medium Substances 0.000 description 1
RDFJFVXMRYVOAC-UHFFFAOYSA-N methiodal Chemical compound OS(=O)(=O)CI RDFJFVXMRYVOAC-UHFFFAOYSA-N 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
238000009608 myelography Methods 0.000 description 1
ZEIPVGFKLCGLRR-UMSGYPCISA-N n-methyl-3,5-dinitro-n-[(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl]benzamide Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CN(C)C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 ZEIPVGFKLCGLRR-UMSGYPCISA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
101150009274 nhr-1 gene Proteins 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000008278 pentosamines Chemical class 0.000 description 1
150000008379 phenol ethers Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000003156 secondary amide group Chemical group 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
210000002330 subarachnoid space Anatomy 0.000 description 1
150000005846 sugar alcohols Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003142 tertiary amide group Chemical group 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002023 wood Substances 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

Landscapes

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)

NO02518/70A 1969-06-27 1970-06-26 NO129093B (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3269969		1969-06-27
GB613070		1970-02-09

Publications (1)

Publication Number	Publication Date
NO129093B true NO129093B (fr)	1974-02-25

Family

ID=26240463

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO02518/70A NO129093B (fr)	1969-06-27	1970-06-26

Country Status (19)

Country	Link
US (1)	US3701771A (fr)
JP (1)	JPS5147702B1 (fr)
AT (1)	AT318134B (fr)
BE (1)	BE752574A (fr)
BR (1)	BR7020080D0 (fr)
CA (1)	CA935153A (fr)
CH (1)	CH544551A (fr)
DE (1)	DE2031724C3 (fr)
DK (1)	DK130709B (fr)
ES (1)	ES381202A1 (fr)
FI (1)	FI53066C (fr)
FR (1)	FR2053037B1 (fr)
HK (1)	HK65978A (fr)
IE (1)	IE34927B1 (fr)
IL (1)	IL34803A (fr)
IT (1)	IT1047908B (fr)
NL (1)	NL153083B (fr)
NO (1)	NO129093B (fr)
SE (1)	SE392100B (fr)

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US4125599A (en) *	1976-08-19	1978-11-14	Mallinckrodt, Inc.	X-ray contrast agents
JPS53137793A (en) *	1977-05-07	1978-12-01	Nihon Seikan Kk	Method of attaching container lid indicating plate
JPS54128855U (fr) *	1978-02-16	1979-09-07
DE2909439A1 (de) *	1979-03-08	1980-09-18	Schering Ag	Neue nichtionische roentgenkontrastmittel
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US4284620A (en)	1979-03-23	1981-08-18	Mallinckrodt, Inc.	N-(2-Hydroxyethyl)-2,4,6-triiodo-3,5-bis-(2-keto-L-gulonamido)benzamide and radiological compositions containing same
US4243653A (en) *	1979-04-27	1981-01-06	The Regents Of The University Of California	Non-ionic polyiodo sugar substituted anilines
DE2928417A1 (de) *	1979-07-12	1981-01-29	Schering Ag	Trijodierte basen
IT1193211B (it) *	1979-08-09	1988-06-15	Bracco Ind Chimica Spa	Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono
DE3001293A1 (de) *	1980-01-11	1981-07-16	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Ionische 5-c-substitiuerte 2,4,6-trijod-isophtalsaeure-derivete
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
US4341756A (en) *	1980-01-31	1982-07-27	The Regents Of The University Of California	Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media
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"
ATE20733T1 (de) *	1982-11-08	1986-08-15	Nyegaard & Co As	Roentgenkontrastmittel.
US4584401A (en) *	1983-10-20	1986-04-22	Biophysica Foundation	Methods and compositions involving polyhydroxylated polyiodo non-ionic contrast media
US5191119A (en) *	1983-10-20	1993-03-02	Cook Imaging Corp.	Process for producing non-ionic radiographic contrast media utilizing N-allylation
DE3407473C2 (de) *	1984-02-29	1986-01-30	Dr. Franz Köhler Chemie GmbH, 6146 Alsbach	N,N-[(3,5-Diacetamido-2,4,6-triiodbenzoyl)-aminoacyl]-N-methylglucamide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel
JPH0813794B2 (ja) *	1985-08-09	1996-02-14	クツクイマジング，インコ−ポレイテイド	イオン性コントラスト媒体からの非イオン性ポリオ−ルコントラスト媒体
US4954348A (en) *	1985-08-09	1990-09-04	Cook Imaging Corporation	Non-ionic polyol contrast media from ionic contrast media
US5035877A (en) *	1985-08-09	1991-07-30	Cook Imaging Corporation	Non-ionic contrast media from ionic contrast media
JPS63166908U (fr) *	1987-04-17	1988-10-31
FR2614299B1 (fr) *	1987-04-23	1989-08-18	Guerbet Sa	Composes diamino benzeniques iodes, leur procede de preparation et produits de contraste les contenant.
AU618535B2 (en) *	1987-05-22	1992-01-02	Bracco International B.V.	Preparation of 5-acylamino-2,4,6-triiodo-or tribromo-benzoic acid derivatives
US5043152A (en) *	1988-06-02	1991-08-27	Guerbet S.A.	Novel iodinated non-ionic triiodobenzene compounds and contrast media containing them
US5698739A (en) *	1989-07-05	1997-12-16	Schering Aktiengesellschaft	Carboxamide non-ionic contrast media
FR2649698B1 (fr) *	1989-07-17	1991-10-25	Guerbet Sa	Nouveaux derives non ioniques polyiodes a structure arylsulfonamide et produit de contraste les contenant
GB8919929D0 (en)	1989-09-04	1989-10-18	Nycomed As	Compositions
US5869024A (en) *	1989-11-29	1999-02-09	Bracco International B.V.	Methods and compositions for using non-ionic contrast agents to reduce the risk of clot formation in diagnostic procedures
US5614638A (en) *	1989-11-29	1997-03-25	Bracco International B.V.	Nonionic radiographic contrast agents
US4997983A (en) *	1990-01-31	1991-03-05	Mallinckrodt, Inc.	Process for production of ioversol
US5527926A (en) *	1990-11-26	1996-06-18	Bracco International B.V.	Methods and compositions for using non-ionic contrast agents to reduce the risk of clot formation in diagnostic procedures
US5278311A (en) *	1992-06-05	1994-01-11	E. R. Squibb & Sons, Inc.	Nonionic radiographic contrast agents
US5668196A (en) *	1995-08-10	1997-09-16	Nanosystems Llc	3-amido-triiodophenyl esters as x-ray contrast agents
US5925683A (en) *	1996-10-17	1999-07-20	Target Therapeutics, Inc.	Liquid embolic agents
US6051210A (en)	1997-05-15	2000-04-18	Bracco Research Usa	N,N-dimethyldiatrizoic acid and its conjugates as hepatobiliary agents for X-ray CT imaging
DE19731591C2 (de) *	1997-07-17	1999-09-16	Schering Ag	Pharmazeutische Mittel enthaltend perfluoralkylgruppenhaltige Trijodaromaten und ihre Verwendung in der Tumortherapie und interventionellen Radiologie
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EP1263324B1 (fr)	2000-03-16	2009-12-02	Veritas Pharmaceuticals	Evaluation radiographique de la reponse tissulaire a des composes
US6660248B2 (en)	2000-11-10	2003-12-09	William Marsh Rice University	Fullerene (C60)-based X-ray contrast agent for diagnostic imaging
US20070191964A1 (en) *	2001-04-04	2007-08-16	Arthrocare Corporation	Enhanced visibility materials for implantation in hard tissue
US7341716B2 (en) *	2002-04-12	2008-03-11	Boston Scientific Scimed, Inc.	Occlusive composition
US7632291B2 (en) *	2003-06-13	2009-12-15	Trivascular2, Inc.	Inflatable implant
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CN101098916A (zh)	2005-01-13	2008-01-02	金文申有限公司	含有碳纳米颗粒的复合材料
EP2104473A1 (fr) *	2007-01-19	2009-09-30	Cinvention Ag	Implant poreux non dégradable réalisé à l'aide d'un moulage de poudre
US20080206862A1 (en) *	2007-02-28	2008-08-28	Cinvention Ag	High surface cultivation system bag
CN101646764A (zh) *	2007-02-28	2010-02-10	金文申有限公司	高表面积培养***
CN101854886B (zh)	2007-03-15	2014-12-24	矫正-空位有限公司	假体装置及其使用方法
CN102336681B (zh) *	2011-07-21	2013-11-13	浙江司太立制药股份有限公司	一种三碘苯类化合物造影剂
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FR6777M (fr) *	1967-07-10	1969-03-10

1970
- 1970-06-26 NO NO02518/70A patent/NO129093B/no unknown
- 1970-06-26 DE DE2031724A patent/DE2031724C3/de not_active Expired
- 1970-06-26 AT AT577970A patent/AT318134B/de not_active IP Right Cessation
- 1970-06-26 JP JP45055344A patent/JPS5147702B1/ja active Pending
- 1970-06-26 IL IL34803A patent/IL34803A/xx unknown
- 1970-06-26 FI FI1802/70A patent/FI53066C/fi active
- 1970-06-26 BR BR220080/70A patent/BR7020080D0/pt unknown
- 1970-06-26 ES ES381202A patent/ES381202A1/es not_active Expired
- 1970-06-26 NL NL707009493A patent/NL153083B/xx not_active IP Right Cessation
- 1970-06-26 DK DK332470AA patent/DK130709B/da not_active IP Right Cessation
- 1970-06-26 FR FR7023704A patent/FR2053037B1/fr not_active Expired
- 1970-06-26 IE IE834/70A patent/IE34927B1/xx unknown
- 1970-06-26 CA CA086599A patent/CA935153A/en not_active Expired
- 1970-06-26 IT IT51731/70A patent/IT1047908B/it active
- 1970-06-26 CH CH973270A patent/CH544551A/de not_active IP Right Cessation
- 1970-06-26 SE SE7008921A patent/SE392100B/xx unknown
- 1970-06-26 US US50075A patent/US3701771A/en not_active Expired - Lifetime
- 1970-06-26 BE BE752574D patent/BE752574A/fr not_active IP Right Cessation
1978
- 1978-11-16 HK HK659/78A patent/HK65978A/xx unknown

Also Published As

Publication number	Publication date
NL7009493A (fr)	1970-12-29
FI53066B (fr)	1977-10-31
IE34927L (en)	1970-12-27
US3701771A (en)	1972-10-31
ES381202A1 (es)	1973-04-16
BR7020080D0 (pt)	1973-03-13
AT318134B (de)	1974-09-25
DE2031724A1 (de)	1971-01-07
IL34803A0 (en)	1970-08-19
FI53066C (fr)	1978-02-10
DK130709C (fr)	1975-09-01
SE392100B (sv)	1977-03-14
DE2031724C3 (de)	1979-06-28
IE34927B1 (en)	1975-10-01
BE752574A (fr)	1970-12-28
HK65978A (en)	1978-11-24
JPS5147702B1 (fr)	1976-12-16
NL153083B (nl)	1977-05-16
IL34803A (en)	1975-03-13
FR2053037A1 (fr)	1971-04-16
DK130709B (da)	1975-04-01
CH544551A (de)	1973-11-30
CA935153A (en)	1973-10-09
IT1047908B (it)	1980-10-20
DE2031724B2 (de)	1978-11-02
FR2053037B1 (fr)	1974-08-09

Publication	Publication Date	Title
NO129093B (fr)	1974-02-25
US4021481A (en)	1977-05-03	Amido derivatives of 2,4,6-triiodobenzoic acids containing at least one N-hydroxyalkyl and at least two hydroxyl groups
EP0015867B1 (fr)	1982-05-19	Diamides d'acides triiodo-isophtaliques, leur préparation et agents de contraste radiographiques les contenant
US3702866A (en)	1972-11-14	Novel 3,5 - bis-acylamido - 2,4,6-triiodobenzoic acids and 5-acylamido-2,4,6-triiodoisophthalamic acids
CA1123009A (fr)	1982-05-04	Derives de l'acide 2,4,6-triiodo-isophtalique, methodes pour leur synthese, et produits de contraste pour rayons x a base de ces derives
DK160868B (da)	1991-04-29	Trijodfenylderivater, fremgangsmaader til fremstilling deraf og radiologisk praeparat indeholdende dem
CA1106401A (fr)	1981-08-04	Acide bis(3,5-dicarbamoyl-2,4,6-triiodoanilides) dicarboxylique
DK150504B (da)	1987-03-16	Trijodisoftalsyrederivater til anvendelse som roentgenkontrastmidler samt radiologiske praeparater indeholdende disse
DK147336B (da)	1984-06-25	5-hydroxypropionylamino-2,4,6-triiod-isophthalsyre-bis(dihydroxypropylamider) til anvendelse i roentgenkontrastmidler og roentgenkontrastmidler indeholdende disse forbindelser
AU616203B2 (en)	1991-10-24	New dicarboxylic acid-bis(3,5-dicarbamoyl-2,4,6- triiodoanilides), process for their production as well as x- ray contrast media containing them
PL124023B1 (en)	1982-12-31	Process for manufacturing novel derivatives of glycerin
DE2523567A1 (de)	1975-12-11	Kontrastmittel fuer roentgenaufnahmen
CS221814B2 (en)	1983-04-29	Method of making the triamide of the acid of 2,4,6-triiodebenzen-1,3-5-tricarboxyle
US4005188A (en)	1977-01-25	X-ray contrast media
DE2624153C2 (de)	1981-10-15	N,N'-acylamido-trijod-benzoylierte Alkylendiamine, Verfahren zu ihrer Herstellung und ihre Verwendung als Kontrastmittel für Röntgenaufnahmen
US3076024A (en)	1963-01-29	Acylated 3, 5-diaminopolyhalobenzoic acids
US3467705A (en)	1969-09-16	Neurotropic amides from n-substituted aminomethyl-nor-camphane and a procedure for their preparation
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