CA1085829A - N-triiodo-benzoylaminoacyl polyhydroxic amines - Google Patents
N-triiodo-benzoylaminoacyl polyhydroxic aminesInfo
- Publication number
- CA1085829A CA1085829A CA273,213A CA273213A CA1085829A CA 1085829 A CA1085829 A CA 1085829A CA 273213 A CA273213 A CA 273213A CA 1085829 A CA1085829 A CA 1085829A
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- carbamyl
- set forth
- formula
- choh
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001412 amines Chemical class 0.000 title claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 81
- -1 N-methylacetamido Chemical group 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 78
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 36
- 125000004442 acylamino group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 9
- 150000008277 ketosamines Chemical class 0.000 claims description 9
- 150000008279 aldosamines Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims 10
- 239000000126 substance Substances 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 239000002872 contrast media Substances 0.000 abstract description 23
- 125000000266 alpha-aminoacyl group Chemical group 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 50
- 239000000203 mixture Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
- 229960000443 hydrochloric acid Drugs 0.000 description 13
- 235000011167 hydrochloric acid Nutrition 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 229960002920 sorbitol Drugs 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 239000003610 charcoal Substances 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229960001701 chloroform Drugs 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229940039231 contrast media Drugs 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000012800 visualization Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 231100000053 low toxicity Toxicity 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- FQORWEQXRQVPBZ-SLPGGIOYSA-N (2r,3s,4r,5s)-5-aminohexane-1,2,3,4,6-pentol Chemical compound OC[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO FQORWEQXRQVPBZ-SLPGGIOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 108010008488 Glycylglycine Proteins 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000002583 angiography Methods 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- JYQQWQJCEUMXQZ-UHFFFAOYSA-N methyl cyanate Chemical compound COC#N JYQQWQJCEUMXQZ-UHFFFAOYSA-N 0.000 description 3
- 238000009608 myelography Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- 231100000041 toxicology testing Toxicity 0.000 description 3
- JMZXMSIXXUDQPV-UHFFFAOYSA-N 2-[(3-acetamido-5-amino-2,4,6-triiodobenzoyl)amino]acetic acid Chemical compound CC(=O)NC1=C(I)C(N)=C(I)C(C(=O)NCC(O)=O)=C1I JMZXMSIXXUDQPV-UHFFFAOYSA-N 0.000 description 2
- 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 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- FZHXIRIBWMQPQF-UHFFFAOYSA-N Glc-NH2 Natural products O=CC(N)C(O)C(O)C(O)CO FZHXIRIBWMQPQF-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
- DWAICOVNOFPYLS-LXGUWJNJSA-N N-acetyl-D-glucosaminitol Chemical compound CC(=O)N[C@@H](CO)[C@@H](O)[C@H](O)[C@H](O)CO DWAICOVNOFPYLS-LXGUWJNJSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- FZHXIRIBWMQPQF-KCDKBNATSA-N aldehydo-D-galactosamine Chemical compound O=C[C@H](N)[C@@H](O)[C@@H](O)[C@H](O)CO FZHXIRIBWMQPQF-KCDKBNATSA-N 0.000 description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- VXINKGICMVWJPA-CTHBEMJXSA-N benzyl n-[2-oxo-2-[[(2s,3r,4s,5r)-1,3,4,5,6-pentahydroxyhexan-2-yl]amino]ethyl]carbamate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)NC(=O)CNC(=O)OCC1=CC=CC=C1 VXINKGICMVWJPA-CTHBEMJXSA-N 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 210000003703 cisterna magna Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012156 elution solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 239000012336 iodinating agent Substances 0.000 description 2
- 230000026045 iodination Effects 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000012360 testing method Methods 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
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- JKGYBHQSGPBXDX-KVQBGUIXSA-N (2r,3s,4s)-2,4,5-trihydroxy-3-(methylamino)pentanal Chemical compound OC[C@@H](O)[C@H](NC)[C@@H](O)C=O JKGYBHQSGPBXDX-KVQBGUIXSA-N 0.000 description 1
- SSMWUNLYJMGHJM-VGRMVHKJSA-N (2r,3s,4s,5s)-4-(ethylamino)-2,3,5,6-tetrahydroxyhexanal Chemical compound CCN[C@@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O SSMWUNLYJMGHJM-VGRMVHKJSA-N 0.000 description 1
- ITVPVFAGCLDNRO-IGBDUZKASA-N (3R,4R,5S,6R)-6-(hydroxymethyl)-3-(methylamino)oxane-2,4,5-triol (2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-(methylamino)hexanal Chemical compound CN[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO.CN[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O ITVPVFAGCLDNRO-IGBDUZKASA-N 0.000 description 1
- OBSLWIKITOYASJ-WLDMJGECSA-N (3r,4r,5r,6r)-6-(hydroxymethyl)-3-(methylamino)oxane-2,4,5-triol Chemical compound CN[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OBSLWIKITOYASJ-WLDMJGECSA-N 0.000 description 1
- QZNPNKJXABGCRC-UYFOZJQFSA-N (3s,4r,5r)-1,3,4,5-tetrahydroxyhexan-2-one Chemical compound C[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO QZNPNKJXABGCRC-UYFOZJQFSA-N 0.000 description 1
- UNCPWMREXAOVOD-UHFFFAOYSA-N 1-(methylamino)propan-2-one Chemical compound CNCC(C)=O UNCPWMREXAOVOD-UHFFFAOYSA-N 0.000 description 1
- YMFOWIJFFPALOW-UHFFFAOYSA-N 2-(methylamino)propane-1,3-diol Chemical compound CNC(CO)CO YMFOWIJFFPALOW-UHFFFAOYSA-N 0.000 description 1
- PJZXWXFIUIDMBP-UHFFFAOYSA-N 2-[(3,5-dinitrobenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 PJZXWXFIUIDMBP-UHFFFAOYSA-N 0.000 description 1
- MYJJRPCXWSQNTB-QYUXJGFFSA-N 2-amino-n-[(2s,3r,4s,5r)-1,3,4,5,6-pentahydroxyhexan-2-yl]acetamide;hydrochloride Chemical compound Cl.NCC(=O)N[C@@H](CO)[C@@H](O)[C@H](O)[C@H](O)CO MYJJRPCXWSQNTB-QYUXJGFFSA-N 0.000 description 1
- 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 1
- WOMTYMDHLQTCHY-UHFFFAOYSA-N 3-methylamino-1,2-propanediol Chemical compound CNCC(O)CO WOMTYMDHLQTCHY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HYGGDKPPAGGKNN-UHFFFAOYSA-N 5-acetamido-2,4,6-triiodobenzene-1,3-dicarbonyl chloride Chemical compound CC(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I HYGGDKPPAGGKNN-UHFFFAOYSA-N 0.000 description 1
- JEZJSNULLBSYHV-UHFFFAOYSA-N 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I JEZJSNULLBSYHV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001480079 Corymbia calophylla Species 0.000 description 1
- MSWZFWKMSRAUBD-SVZMEOIVSA-N D-talosamine Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-SVZMEOIVSA-N 0.000 description 1
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Classifications
-
- 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
- C07C233/12—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 halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66638976A | 1976-03-12 | 1976-03-12 | |
| US666,389 | 1976-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085829A true CA1085829A (en) | 1980-09-16 |
Family
ID=24673972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA273,213A Expired CA1085829A (en) | 1976-03-12 | 1977-03-04 | N-triiodo-benzoylaminoacyl polyhydroxic amines |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS52128346A (Direct) |
| AU (1) | AU508186B2 (Direct) |
| BE (1) | BE852418A (Direct) |
| CA (1) | CA1085829A (Direct) |
| DE (1) | DE2710730A1 (Direct) |
| FR (1) | FR2343718A1 (Direct) |
| GB (1) | GB1524493A (Direct) |
| NL (1) | NL7702407A (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR970001000B1 (ko) * | 1987-11-28 | 1997-01-25 | 닛본 신야쿠 가부시기가이샤 | 아미노디옥시만니톨의 제법 |
-
1977
- 1977-02-24 GB GB784577A patent/GB1524493A/en not_active Expired
- 1977-03-04 CA CA273,213A patent/CA1085829A/en not_active Expired
- 1977-03-07 JP JP2398377A patent/JPS52128346A/ja active Pending
- 1977-03-07 NL NL7702407A patent/NL7702407A/xx not_active Application Discontinuation
- 1977-03-08 AU AU23011/77A patent/AU508186B2/en not_active Expired
- 1977-03-11 DE DE19772710730 patent/DE2710730A1/de not_active Withdrawn
- 1977-03-11 FR FR7707365A patent/FR2343718A1/fr active Granted
- 1977-03-14 BE BE175749A patent/BE852418A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU508186B2 (en) | 1980-03-13 |
| FR2343718B1 (Direct) | 1978-12-29 |
| BE852418A (fr) | 1977-07-01 |
| AU2301177A (en) | 1978-09-14 |
| FR2343718A1 (fr) | 1977-10-07 |
| GB1524493A (en) | 1978-09-13 |
| JPS52128346A (en) | 1977-10-27 |
| NL7702407A (nl) | 1977-09-14 |
| DE2710730A1 (de) | 1977-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |