NO127445B - - Google Patents
Download PDFInfo
- Publication number
- NO127445B NO127445B NO114668A NO114668A NO127445B NO 127445 B NO127445 B NO 127445B NO 114668 A NO114668 A NO 114668A NO 114668 A NO114668 A NO 114668A NO 127445 B NO127445 B NO 127445B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- triiodo
- water
- acid
- propionic acid
- Prior art date
Links
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 26
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 23
- -1 phenyloxy Chemical group 0.000 claims description 18
- 239000002872 contrast media Substances 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 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 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 55
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 238000009835 boiling Methods 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 19
- 238000004458 analytical method Methods 0.000 description 18
- 159000000000 sodium salts Chemical class 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 210000000941 bile Anatomy 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 229960003424 phenylacetic acid Drugs 0.000 description 13
- 239000003279 phenylacetic acid Substances 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000009606 cholecystography Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- AGBPWBNBTQKNCT-UHFFFAOYSA-N 2-(3-amino-2,4,6-triiodophenoxy)-2-phenylacetic acid Chemical class NC1=C(I)C=C(I)C(OC(C(O)=O)C=2C=CC=CC=2)=C1I AGBPWBNBTQKNCT-UHFFFAOYSA-N 0.000 description 5
- ZSBOXQIYDXCBKN-UHFFFAOYSA-N 2-(3-amino-2,4,6-triiodophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=C(I)C=C(I)C(N)=C1I ZSBOXQIYDXCBKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000020477 pH reduction Effects 0.000 description 5
- 239000008159 sesame oil Substances 0.000 description 5
- 235000011803 sesame oil Nutrition 0.000 description 5
- 239000000052 vinegar Substances 0.000 description 5
- 235000021419 vinegar Nutrition 0.000 description 5
- SHDHSGPFZOKKBX-UHFFFAOYSA-N 2-(3-amino-2,4,6-triiodophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=C(I)C=C(I)C(N)=C1I SHDHSGPFZOKKBX-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- REULTXDITAVBTJ-UHFFFAOYSA-N 2-(3-aminophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC(N)=C1 REULTXDITAVBTJ-UHFFFAOYSA-N 0.000 description 3
- UMVOCNFWVVRKKE-UHFFFAOYSA-N 2-(3-aminophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC(N)=C1 UMVOCNFWVVRKKE-UHFFFAOYSA-N 0.000 description 3
- PCXRKBKTFCWGLA-UHFFFAOYSA-N 2-(3-nitrophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC([N+]([O-])=O)=C1 PCXRKBKTFCWGLA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 210000000232 gallbladder Anatomy 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- INVBOJSWUDDQJX-UHFFFAOYSA-N 2-(3-amino-2,4,6-triiodophenyl)acetic acid Chemical compound NC1=C(I)C=C(I)C(CC(O)=O)=C1I INVBOJSWUDDQJX-UHFFFAOYSA-N 0.000 description 2
- GHRSXULZYXRAAT-UHFFFAOYSA-N 2-(3-nitrophenyl)butanenitrile Chemical compound CCC(C#N)C1=CC=CC([N+]([O-])=O)=C1 GHRSXULZYXRAAT-UHFFFAOYSA-N 0.000 description 2
- MSCZZRXBIBUPKG-UHFFFAOYSA-N 2-(3-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=CC([N+]([O-])=O)=C1 MSCZZRXBIBUPKG-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229940039231 contrast media Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002497 iodine compounds Chemical class 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- IRFPSCXQOFKZAV-UHFFFAOYSA-N 1-(1-bromopropyl)-3-nitrobenzene Chemical compound CCC(Br)C1=CC=CC([N+]([O-])=O)=C1 IRFPSCXQOFKZAV-UHFFFAOYSA-N 0.000 description 1
- RMIWZYGLHJJFRO-UHFFFAOYSA-N 2-(3-nitrophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=CC([N+]([O-])=O)=C1 RMIWZYGLHJJFRO-UHFFFAOYSA-N 0.000 description 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
- OKRUMSWHDWKGHA-UHFFFAOYSA-N 5-bromopentanoyl chloride Chemical compound ClC(=O)CCCCBr OKRUMSWHDWKGHA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 206010053172 Fatal outcomes Diseases 0.000 description 1
- 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 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- OIRFJRBSRORBCM-UHFFFAOYSA-N Iopanoic acid Chemical compound CCC(C(O)=O)CC1=C(I)C=C(I)C(N)=C1I OIRFJRBSRORBCM-UHFFFAOYSA-N 0.000 description 1
- BUPJOLXWQXEJSQ-UHFFFAOYSA-N Lactifloreol Natural products C=C1CCC(C(C)C)=CC2C(O)(C)CCC21 BUPJOLXWQXEJSQ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- WASPIBFUIKHPFF-UHFFFAOYSA-N N-(3-hydroxy-2,4,6-triiodophenyl)formamide Chemical compound C(=O)NC=1C(=C(C(=CC1I)I)O)I WASPIBFUIKHPFF-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- BKTKLDMYHTUESO-UHFFFAOYSA-N ethyl 2-bromo-2-phenylacetate Chemical compound CCOC(=O)C(Br)C1=CC=CC=C1 BKTKLDMYHTUESO-UHFFFAOYSA-N 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- GOIQOQCNFWYSTQ-UHFFFAOYSA-N iophenoic acid Chemical compound CCC(C(O)=O)CC1=C(I)C=C(I)C(O)=C1I GOIQOQCNFWYSTQ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- BYTCDABWEGFPLT-UHFFFAOYSA-L potassium;sodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[K+] BYTCDABWEGFPLT-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000007487 urography Methods 0.000 description 1
- 229930192406 valerol Natural products 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH499167A CH483260A (de) | 1967-04-06 | 1967-04-06 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
| CH861867A CH490857A (de) | 1967-04-06 | 1967-06-16 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127445B true NO127445B (enrdf_load_html_response) | 1973-06-25 |
Family
ID=25696701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO114668A NO127445B (enrdf_load_html_response) | 1967-04-06 | 1968-03-25 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO127445B (enrdf_load_html_response) |
-
1968
- 1968-03-25 NO NO114668A patent/NO127445B/no unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4190671A (en) | Chalcone derivatives | |
| JP2950616B2 (ja) | トリテルペン誘導体 | |
| NO142441B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk virksomme karboksylsyrederivater | |
| US4731470A (en) | [(5,6-dichloro-3-oxo-2,9a-alkano-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]alkanoic acids and alkanimidamides | |
| JPH0150698B2 (enrdf_load_html_response) | ||
| Boyd | The isolation of amino-acids in the form of the corresponding carbamido-acids and hydantoins: The derivatives of the mono-aminomonocarboxylic acids | |
| US3890318A (en) | Derivatives of triiodo aminobenzenecarboxylic acids and the preparation thereof | |
| SU843744A3 (ru) | Способ получени производных бензимидазола или их солей | |
| US3996279A (en) | Novel 2-amino methyl-4,6-dihalogenphenol derivatives and methods for the preparation thereof | |
| NO127445B (enrdf_load_html_response) | ||
| US4176190A (en) | Diuretic and saliuretic sulphamoylbenzoic acids | |
| LaForge et al. | A new constituent isolated from southern prickly-ash bark | |
| NO130549B (enrdf_load_html_response) | ||
| US4473583A (en) | Compositions containing certain derivatives of 4-phenyl-4-oxobuten-2-oic acid and methods of treatment using them | |
| US3139455A (en) | Phenoxyacetamidoximes | |
| US4118504A (en) | Isoindoline derivatives for treating pain | |
| US3644409A (en) | Radiopaque compounds and methods of preparing the same | |
| US3112337A (en) | 4-halo-3-sulfamoylbenzoic acid esters | |
| NO132234B (enrdf_load_html_response) | ||
| SU803859A3 (ru) | Способ получени -тиопропионами-дОВ или иХ КиСлОТНО-АддиТиВНыХСОлЕй | |
| NO121610B (enrdf_load_html_response) | ||
| NO120271B (enrdf_load_html_response) | ||
| NO121611B (enrdf_load_html_response) | ||
| US3925396A (en) | {62 -Pyridyl-carbonamido-alkane-sulfonic acid salts | |
| PL90337B1 (enrdf_load_html_response) |