NL194271C - Werkwijze voor de bereiding van de verbinding L-5-(2-acetoxy-propionylamino)-2,4,6-trijood-isoftaalzuur-bis-(1,3- -dihydropropylamide). - Google Patents
Werkwijze voor de bereiding van de verbinding L-5-(2-acetoxy-propionylamino)-2,4,6-trijood-isoftaalzuur-bis-(1,3- -dihydropropylamide). Download PDFInfo
- Publication number
- NL194271C NL194271C NL9301822A NL9301822A NL194271C NL 194271 C NL194271 C NL 194271C NL 9301822 A NL9301822 A NL 9301822A NL 9301822 A NL9301822 A NL 9301822A NL 194271 C NL194271 C NL 194271C
- Authority
- NL
- Netherlands
- Prior art keywords
- acetoxy
- propionylamino
- reaction
- under stirring
- kept under
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- 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 title claims description 6
- 150000001875 compounds Chemical class 0.000 title description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 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
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- -1 2-acetoxy-propionylamino Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000004809 thin layer chromatography Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GMPOMLNJZPYPGR-VKHMYHEASA-N [(2s)-1-(3,5-dicarbonochloridoyl-2,4,6-triiodoanilino)-1-oxopropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](C)C(=O)NC1=C(I)C(C(Cl)=O)=C(I)C(C(Cl)=O)=C1I GMPOMLNJZPYPGR-VKHMYHEASA-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
- 239000013078 crystal Substances 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims 2
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229940126062 Compound A Drugs 0.000 description 7
- 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 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 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
- DOGCTUGYGZGSFX-UHFFFAOYSA-N 1-aminopropane-1,3-diol Chemical compound NC(O)CCO DOGCTUGYGZGSFX-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QMADWSQEVHUFFJ-UHFFFAOYSA-N 2,4,5-triiodobenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(I)=C(I)C(C(O)=O)=C1I QMADWSQEVHUFFJ-UHFFFAOYSA-N 0.000 description 1
- WTLNOANVTIKPEE-UHFFFAOYSA-N 2-acetyloxypropanoic acid Chemical compound OC(=O)C(C)OC(C)=O WTLNOANVTIKPEE-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 229940039231 contrast media Drugs 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000012631 diagnostic technique Methods 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
- 239000001630 malic acid Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005292 vacuum distillation 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI922451 | 1992-10-27 | ||
| ITMI922451A IT1256163B (it) | 1992-10-27 | 1992-10-27 | Processo per la preparazione di un intermedio della sintesi organica |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL9301822A NL9301822A (nl) | 1994-05-16 |
| NL194271B NL194271B (nl) | 2001-07-02 |
| NL194271C true NL194271C (nl) | 2001-11-05 |
Family
ID=11364170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL9301822A NL194271C (nl) | 1992-10-27 | 1993-10-20 | Werkwijze voor de bereiding van de verbinding L-5-(2-acetoxy-propionylamino)-2,4,6-trijood-isoftaalzuur-bis-(1,3- -dihydropropylamide). |
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 |
| 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 |
| 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 |
| 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 DE DE4336154A patent/DE4336154A1/de not_active Ceased
- 1993-10-22 FR FR9312614A patent/FR2697249B1/fr not_active Expired - Lifetime
- 1993-10-26 ES ES09302237A patent/ES2073370B1/es not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2272218B (en) | 1995-11-22 |
| GB9320888D0 (en) | 1993-12-01 |
| CH688147A5 (it) | 1997-05-30 |
| IT1256163B (it) | 1995-11-29 |
| FR2697249A1 (fr) | 1994-04-29 |
| ITMI922451A0 (it) | 1992-10-27 |
| FR2697249B1 (fr) | 1995-04-14 |
| NL194271B (nl) | 2001-07-02 |
| NL9301822A (nl) | 1994-05-16 |
| GB2272218A (en) | 1994-05-11 |
| ES2073370B1 (es) | 1996-02-16 |
| ES2073370A1 (es) | 1995-08-01 |
| DE4336154A1 (de) | 1994-04-28 |
| ITMI922451A1 (it) | 1994-04-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6974882B2 (en) | Preparation of iodixanol | |
| JPS6328438B2 (de) | ||
| NL194272C (nl) | Werkwijze voor de kristallisatie van iopamidol. | |
| NL194271C (nl) | Werkwijze voor de bereiding van de verbinding L-5-(2-acetoxy-propionylamino)-2,4,6-trijood-isoftaalzuur-bis-(1,3- -dihydropropylamide). | |
| NL194332C (nl) | Werkwijze ter bereiding van L-5-(2-hydroxypropionylamino)-2,4,6- trijoodisoftaalzuur-bis-(1,3-dihydroxypropylamide). | |
| NL194993C (nl) | Werkwijze voor de bereiding van L-5-(2-acetoxy-propionylamino)-2,4,6-trijodo-isoftaalzuurdichloride. | |
| BG63663B1 (bg) | Метод за получаване на йохексол | |
| JP4450987B2 (ja) | アルコキシフラノンアミン誘導体の製造方法、この方法で得られた化合物及びこれらの化合物の用途 | |
| US5817861A (en) | Process for the preparation of an intermediate useful in the synthesis of iodinated contrast media | |
| US4540817A (en) | Process for the preparation of 5-amino-2,4-dimethylacetanilide | |
| JPH08333319A (ja) | イオパミドールの精製及び晶出方法 | |
| JP3291991B2 (ja) | Ｏ，ｓ−ジメチル ｎ−アセチルホスホルアミドチオエートの精製法 | |
| US4914195A (en) | Process for preparing N-acetylneuraminic acid derivatives | |
| EP0127128A1 (de) | Verfahren zur Umwandlung von 1,2-Diphenyl-1-[4-(2-dimethylamino-ethoxy)-phenyl]-1-buten-E-Isomeren zu Tamoxifen-Hydrochlorid | |
| JP4397990B2 (ja) | ３−アルキルフラバノノール誘導体の精製法 | |
| NL9001459A (nl) | Nieuwe stereoselectieve hydrogeneringswerkwijze. | |
| KR20000070926A (ko) | 선형 또는 분지형 (ｃ5-ｃ6) 알콜 또는 그의 혼합물로부터 (ｓ)-ｎ,ｎ'-비스[2-히드록시-1-(히드록시메틸)에틸]-5-[(2-히드록시-1-옥소프로필)아미노]-2,4,6-트리요오도-1,3-벤젠디카르복스아미드의 결정화 방법 | |
| US4676933A (en) | Method for purification of amido acids | |
| CA2710577C (en) | Crystallization of iodixanol using milling | |
| JP2003095991A (ja) | 光学活性３，３，３−トリフルオロ−２−ヒドロキシ−２−メチルプロピオン酸の製造法 | |
| SK4302002A3 (en) | Method for the preparation of (E)-N-(6,6-dimethylhept-2-en-4- ynyl)-N-methyl-1-naphthalenemethanamine from a geometric isomers mixture | |
| JPH0368571A (ja) | Ｎ―置換２、４、６―トリイミノトリアジン誘導体の製造方法 | |
| PL114673B2 (en) | Process for purification of alpha-pyroglutamic acid from impurities,especially from alpha-glutamic acid and derivatives of alpha-pyroglutamic acid | |
| JPH0794427B2 (ja) | Ｎ，ｎ―ジアルキルアミノチオアセトアミドの製造法 | |
| JPH10147560A (ja) | Ｎ−２−ブロモエチル−アミノ安息香酸誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: BRACCO INTERNATIONAL B.V. |
|
| SNR | Assignments of patents or rights arising from examined patent applications |
Owner name: BRACCO IMAGING S.P.A. |
|
| V4 | Discontinued because of reaching the maximum lifetime of a patent |
Effective date: 20131020 |