NO120271B - - Google Patents
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- Publication number
- NO120271B NO120271B NO1542/68A NO154268A NO120271B NO 120271 B NO120271 B NO 120271B NO 1542/68 A NO1542/68 A NO 1542/68A NO 154268 A NO154268 A NO 154268A NO 120271 B NO120271 B NO 120271B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- triiodo
- acid
- acetylamino
- water
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- -1 amine salts Chemical class 0.000 claims description 5
- 239000002872 contrast media Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- OCJFLSKQLCGZIF-UHFFFAOYSA-N 2-[3-(butanoylamino)-2,4,6-triiodophenyl]butanoic acid Chemical group CCCC(=O)NC1=C(I)C=C(I)C(C(CC)C(O)=O)=C1I OCJFLSKQLCGZIF-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000008018 melting Effects 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229940005605 valeric acid Drugs 0.000 description 9
- 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 7
- 210000000941 bile Anatomy 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000009606 cholecystography Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005245 sintering Methods 0.000 description 5
- DRNUVHPHNAYHHF-UHFFFAOYSA-N 2-(3-acetamido-2,4,6-triiodophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=C(I)C=C(I)C(NC(C)=O)=C1I DRNUVHPHNAYHHF-UHFFFAOYSA-N 0.000 description 4
- NMAGEGBGCORVJO-UHFFFAOYSA-N 2-(3-acetamido-2,4,6-triiodophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=C(I)C=C(I)C(NC(C)=O)=C1I NMAGEGBGCORVJO-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 210000000232 gallbladder Anatomy 0.000 description 3
- 230000026045 iodination Effects 0.000 description 3
- 238000006192 iodination reaction Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- DJFPKDMQDASJED-UHFFFAOYSA-N 2-(3-acetamido-2,4,6-triiodophenyl)pentanoic acid Chemical compound CCCC(C(O)=O)C1=C(I)C=C(I)C(NC(C)=O)=C1I DJFPKDMQDASJED-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 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 2
- IXPFNDDSBURDAF-UHFFFAOYSA-N 2-[3-[acetyl(ethyl)amino]-2,4,6-triiodophenyl]butanoic acid Chemical compound CCC(C(O)=O)C1=C(I)C=C(I)C(N(CC)C(C)=O)=C1I IXPFNDDSBURDAF-UHFFFAOYSA-N 0.000 description 2
- SKDCYRFSNRNKOS-UHFFFAOYSA-N 2-[3-[acetyl(methyl)amino]-2,4,6-triiodophenyl]butanoic acid Chemical compound CCC(C(O)=O)C1=C(I)C=C(I)C(N(C)C(C)=O)=C1I SKDCYRFSNRNKOS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- 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 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940079360 enema for constipation Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- VXVFAPNEGUKSCX-UHFFFAOYSA-N 1-(1-bromobutyl)-3-nitrobenzene Chemical compound CCCC(Br)C1=CC=CC([N+]([O-])=O)=C1 VXVFAPNEGUKSCX-UHFFFAOYSA-N 0.000 description 1
- CBTKUSGOSLITSO-UHFFFAOYSA-N 1-(1-bromoethyl)-3-nitrobenzene Chemical compound CC(Br)C1=CC=CC([N+]([O-])=O)=C1 CBTKUSGOSLITSO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 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
- 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 1
- CJGNNXCKYVIXSY-UHFFFAOYSA-N 2-[3-[acetyl(methyl)amino]-2,4,6-triiodophenyl]propanoic acid Chemical compound OC(=O)C(C)C1=C(I)C=C(I)C(N(C)C(C)=O)=C1I CJGNNXCKYVIXSY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 229960002979 iopanoic acid Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0452—Solutions, e.g. for injection
-
- 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
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0495—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound intended for oral administration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH748067A CH480072A (de) | 1967-05-29 | 1967-05-29 | Neue Röntgenkontrastmittel und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120271B true NO120271B (de) | 1970-09-28 |
Family
ID=4325775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1542/68A NO120271B (de) | 1967-05-29 | 1968-04-23 |
Country Status (8)
| Country | Link |
|---|---|
| AT (2) | AT277450B (de) |
| BE (1) | BE715797A (de) |
| CH (1) | CH480072A (de) |
| ES (1) | ES354411A1 (de) |
| FR (2) | FR7442M (de) |
| GB (1) | GB1228596A (de) |
| NL (1) | NL6805224A (de) |
| NO (1) | NO120271B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2725201B1 (fr) * | 1994-09-29 | 1996-11-15 | Rhone Poulenc Rorer Sa | Procede de preparation de derives du nitrobenzene |
-
1967
- 1967-05-29 CH CH748067A patent/CH480072A/de not_active IP Right Cessation
-
1968
- 1968-04-11 NL NL6805224A patent/NL6805224A/xx unknown
- 1968-04-23 NO NO1542/68A patent/NO120271B/no unknown
- 1968-05-07 GB GB1228596D patent/GB1228596A/en not_active Expired
- 1968-05-27 AT AT506468A patent/AT277450B/de not_active IP Right Cessation
- 1968-05-27 AT AT00608/69A patent/AT284827B/de not_active IP Right Cessation
- 1968-05-28 ES ES354411A patent/ES354411A1/es not_active Expired
- 1968-05-28 BE BE715797D patent/BE715797A/xx unknown
- 1968-05-29 FR FR153223A patent/FR7442M/fr not_active Expired
- 1968-05-29 FR FR1590609D patent/FR1590609A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7442M (de) | 1969-11-17 |
| BE715797A (de) | 1968-11-28 |
| GB1228596A (de) | 1971-04-15 |
| NL6805224A (de) | 1968-12-02 |
| FR1590609A (de) | 1970-04-20 |
| AT277450B (de) | 1969-12-29 |
| AT284827B (de) | 1970-09-25 |
| CH480072A (de) | 1969-10-31 |
| ES354411A1 (es) | 1969-11-01 |
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