CH688147A5 - Processo per la preparazione del composto bis-(1,3-diidrossipropilamide) dell'acido L-5-(2-acetossi-propionilammino)-2,4,6-triiodo-isoftalico. - Google Patents
Processo per la preparazione del composto bis-(1,3-diidrossipropilamide) dell'acido L-5-(2-acetossi-propionilammino)-2,4,6-triiodo-isoftalico. Download PDFInfo
- Publication number
- CH688147A5 CH688147A5 CH02991/93A CH299193A CH688147A5 CH 688147 A5 CH688147 A5 CH 688147A5 CH 02991/93 A CH02991/93 A CH 02991/93A CH 299193 A CH299193 A CH 299193A CH 688147 A5 CH688147 A5 CH 688147A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acetoxy
- reaction
- compound
- isophthalic
- propionylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 title description 9
- -1 2-acetoxy-propionylamino Chemical group 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- 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 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 6
- 229920006063 Lamide® Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 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 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- GLIODNATPFPVFB-VKHMYHEASA-N 5-[[(2s)-2-acetyloxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(O)=O)=C1I GLIODNATPFPVFB-VKHMYHEASA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- DOGCTUGYGZGSFX-UHFFFAOYSA-N 1-aminopropane-1,3-diol Chemical compound NC(O)CCO DOGCTUGYGZGSFX-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- ALHZEIINTQJLOT-VKHMYHEASA-N [(2s)-1-chloro-1-oxopropan-2-yl] acetate Chemical compound ClC(=O)[C@H](C)OC(C)=O ALHZEIINTQJLOT-VKHMYHEASA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RERHJVNYJKZHLJ-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;2-(3,5-diiodo-4-oxopyridin-1-yl)acetate Chemical compound OCCNCCO.OC(=O)CN1C=C(I)C(=O)C(I)=C1 RERHJVNYJKZHLJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI922451A IT1256163B (it) | 1992-10-27 | 1992-10-27 | Processo per la preparazione di un intermedio della sintesi organica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH688147A5 true CH688147A5 (it) | 1997-05-30 |
Family
ID=11364170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH02991/93A CH688147A5 (it) | 1992-10-27 | 1993-10-05 | Processo per la preparazione del composto bis-(1,3-diidrossipropilamide) dell'acido L-5-(2-acetossi-propionilammino)-2,4,6-triiodo-isoftalico. |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH688147A5 (de) |
| DE (1) | DE4336154A1 (de) |
| ES (1) | ES2073370B1 (de) |
| FR (1) | FR2697249B1 (de) |
| GB (1) | GB2272218B (de) |
| IT (1) | IT1256163B (de) |
| NL (1) | NL194271C (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1283319B1 (it) * | 1996-03-29 | 1998-04-16 | Zambon Spa | Processo per la preparazione di un intermedio utile nella sintesi di mezzi di contrasto iodurati |
| IT1299202B1 (it) * | 1998-05-08 | 2000-02-29 | Dibra Spa | Processo per la preparazione della s-n,n'-bis (2-idrossi-1- (idrossimetil)etil) -5-((2-idrossi-1-ossopropil)ammino)-2,4,6-triiodo |
| US6262303B1 (en) | 1998-05-08 | 2001-07-17 | Dibra S.P.A. | Process for the preparation of S-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)-amino]-2,4,6-triiodo-1,3-benzenedicarboxamide |
| IT1302200B1 (it) | 1998-09-11 | 2000-07-31 | Dibra Spa | PROCESSO PER LA PREPARAZIONE DELLA S-N,N'-BIS°2-IDROSSI-1-(IDROSSIMETIL)ETILé-5-°(2-IDROSSI-1- |
| US6803485B2 (en) | 1999-02-26 | 2004-10-12 | Bracco Imaging S.P.A. | Process for the preparation of iopamidol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH608189A5 (de) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| FR2656865B1 (fr) * | 1990-01-05 | 1993-03-26 | Guerbet Sa | Compose non ionique iode, son procede de preparation et produit de contraste le contenant. |
| ES2017277A6 (es) * | 1989-09-20 | 1991-01-16 | Juste Sa | Un procedimiento para la preparacion de nuevos agentes iodados no ionicos de contraste. |
-
1992
- 1992-10-27 IT ITMI922451A patent/IT1256163B/it active IP Right Grant
-
1993
- 1993-10-05 CH CH02991/93A patent/CH688147A5/it not_active IP Right Cessation
- 1993-10-11 GB GB9320888A patent/GB2272218B/en not_active Expired - Fee Related
- 1993-10-20 NL NL9301822A patent/NL194271C/nl not_active IP Right Cessation
- 1993-10-22 FR FR9312614A patent/FR2697249B1/fr not_active Expired - Lifetime
- 1993-10-22 DE DE4336154A patent/DE4336154A1/de not_active Ceased
- 1993-10-26 ES ES09302237A patent/ES2073370B1/es not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB9320888D0 (en) | 1993-12-01 |
| FR2697249A1 (fr) | 1994-04-29 |
| ITMI922451A1 (it) | 1994-04-27 |
| NL194271B (nl) | 2001-07-02 |
| NL9301822A (nl) | 1994-05-16 |
| FR2697249B1 (fr) | 1995-04-14 |
| ITMI922451A0 (it) | 1992-10-27 |
| NL194271C (nl) | 2001-11-05 |
| ES2073370A1 (es) | 1995-08-01 |
| GB2272218B (en) | 1995-11-22 |
| ES2073370B1 (es) | 1996-02-16 |
| DE4336154A1 (de) | 1994-04-28 |
| GB2272218A (en) | 1994-05-11 |
| IT1256163B (it) | 1995-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: ZAMBON GROUP S.P.A. TRANSFER- BRACCO INTERNATIONAL |
|
| PL | Patent ceased |