HUP9901631A2 - Eljárás iopamidol gyártásánál használt köztitermékek előállítására - Google Patents
Eljárás iopamidol gyártásánál használt köztitermékek előállításáraInfo
- Publication number
- HUP9901631A2 HUP9901631A2 HU9901631A HUP9901631A HUP9901631A2 HU P9901631 A2 HUP9901631 A2 HU P9901631A2 HU 9901631 A HU9901631 A HU 9901631A HU P9901631 A HUP9901631 A HU P9901631A HU P9901631 A2 HUP9901631 A2 HU P9901631A2
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- iii
- triiodo
- oxy
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 title 1
- 229960004647 iopamidol Drugs 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 239000011347 resin Substances 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000129 anionic group Chemical group 0.000 abstract 2
- 125000002091 cationic group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 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 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000004575 stone Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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)
- Removal Of Specific Substances (AREA)
- Carbon And Carbon Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A találmány tárgya eljárás a (III) képletű (S)-N,N'-bisz[2-hidrőxi-1-(hidrőxi-metil)-etil]-5-[(2-hidrőxi-1-őxő-prőpil)-aminő]-2,4,6,trijód-1,3-fenilén-dikarbőxamid előállítására. Az eljárást az jellemzi, hőgy(i) az (I) képletű 5-aminő-2,4,6-trijód-1,3-fenilén-dikarbőnsav-diklőridőt S-(-)-[2-(acetil-őxi)]-prőpiőnsav-klőriddal reagáltatjákdimetil-acetamidban, (ii) a (II) képletű (S)-5-[[2-(acetil-őxi)-1-őxő-prőpil]-aminő]-2,4,6-trijód-1,3-fenilén-dikarbőnsav-diklőrid (i)lépésben kapőtt dimetil-acetamidős őldatát pórűsős és/vagymakrőpórűsős térhálósítőtt aniőnős és katiőnős gyantákőn - az aniőnősgyantákat szabad bázisős főrmában és a katiőnős gyantákat nátriűmsófőrmájában használva - elűálják, azzal a megkötéssel, hőgy az említettőldatból és gyantákból álló rendszer annyi vizet tartalmaz, hőgy azképes legyen az S-(-)-[2-(acetil-őxi)]-prőpiőnsav-klőrid fölöslegéthidrőlizálni, de ne legyen képes a (II) képletű diklőridőthidrőlizálni, (iii) a (ii) lépésben kapőtt őldatból a vizet adőttesetben eltávőlítják, 0-2% víztartalmat beállítva, (iv) szerinnelreagáltatást végeznek 0 řC és 10 řC közötti hőmérsékleten 5 óra és 20óra közötti reakcióidővel, és (v) a (III) képletű vegyületetelkülönítik. A találmány szerinti eljárással lehetővé válik előzeteselkülönítés nélkül, közvetlenül a (III) képletű vegyület előállítása. ŕ
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT96MI001204A IT1288114B1 (it) | 1996-06-13 | 1996-06-13 | Processo per la purificazione di un intermedio |
| PCT/EP1997/003021 WO1997047590A2 (en) | 1996-06-13 | 1997-06-11 | Process for the purification of an intermediate in the preparation of iopamidol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9901631A2 true HUP9901631A2 (hu) | 1999-08-30 |
| HUP9901631A3 HUP9901631A3 (en) | 2001-02-28 |
| HU227980B1 HU227980B1 (en) | 2012-07-30 |
Family
ID=11374420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9901631A HU227980B1 (en) | 1996-06-13 | 1997-06-11 | Process for the purification of an intermediate in the preparation of iopamidol |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5849953A (hu) |
| EP (1) | EP0851854B1 (hu) |
| JP (1) | JP4018751B2 (hu) |
| CN (1) | CN1089335C (hu) |
| AT (1) | ATE210630T1 (hu) |
| AU (1) | AU3094597A (hu) |
| CZ (1) | CZ293956B6 (hu) |
| DE (1) | DE69709044T2 (hu) |
| ES (1) | ES2165610T3 (hu) |
| HU (1) | HU227980B1 (hu) |
| IL (1) | IL123259A (hu) |
| IN (1) | IN182809B (hu) |
| IT (1) | IT1288114B1 (hu) |
| NO (1) | NO324342B1 (hu) |
| PT (1) | PT851854E (hu) |
| WO (1) | WO1997047590A2 (hu) |
| ZA (1) | ZA975203B (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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- |
| DE102007053531B4 (de) * | 2007-11-09 | 2010-10-21 | Hs Genion Gmbh | Rolloeinrichtung |
| EP2230227A1 (en) | 2009-03-20 | 2010-09-22 | Bracco Imaging S.p.A | Process for the preparation of triiodinated carboxylic aromatic derivatives |
| EP2243767A1 (en) | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
| IT1403988B1 (it) * | 2010-07-15 | 2013-11-08 | Bracco Imaging Spa | Processo per la preparazione di agenti di contrasto. |
| PL2931696T3 (pl) | 2012-12-11 | 2019-01-31 | Bracco Imaging S.P.A | Ciągły sposób otrzymywania kwasu (S)-2-acetyloksypropionowego |
| CA2927706C (en) | 2013-11-05 | 2018-05-29 | Bracco Imaging Spa | Process for the preparation of iopamidol |
| CA2949433C (en) | 2014-06-10 | 2022-05-03 | Bracco Imaging Spa | Method for the preparation of (s)-2-acetyloxypropionic acid and derivatives thereof |
| PT108524B (pt) * | 2015-06-02 | 2017-12-15 | Hovione Farmaciência S A | Processo para a preparação de intermediários úteis na preparação de agentes de contraste não-iónicos |
| WO2018104228A1 (en) | 2016-12-05 | 2018-06-14 | Bracco Imaging Spa | Mechanochemical synthesis of radiographic agents intermediates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3324107A (en) * | 1964-03-27 | 1967-06-06 | Du Pont | Dialkylamide purification |
| US3576870A (en) * | 1967-07-05 | 1971-04-27 | Du Pont | Process for purifying n,n-dimethylacetamide |
| CH608189A5 (hu) * | 1974-12-13 | 1978-12-29 | Savac Ag | |
| CH616403A5 (en) * | 1975-10-29 | 1980-03-31 | Bracco Ind Chimica Spa | Process for the preparation of 2,4,6-triodoisophthalamides which are readily soluble in water. |
| IT1193211B (it) * | 1979-08-09 | 1988-06-15 | Bracco Ind Chimica Spa | Derivati dell'acido 2,4,6-triiodo-isoftalico,metodo per la loro preparazione e mezzi di contrasto che li contengono |
| GB2088850B (en) * | 1980-12-09 | 1983-09-28 | Coal Industry Patents Ltd | Treatment of n-methyl pyrrolidone |
| IT1256162B (it) * | 1992-10-27 | 1995-11-29 | Zambon Spa | Processo per la preparazione di un intermedio della sintesi organica |
-
1996
- 1996-06-13 IT IT96MI001204A patent/IT1288114B1/it active IP Right Grant
-
1997
- 1997-06-11 EP EP97925993A patent/EP0851854B1/en not_active Expired - Lifetime
- 1997-06-11 PT PT97925993T patent/PT851854E/pt unknown
- 1997-06-11 ES ES97925993T patent/ES2165610T3/es not_active Expired - Lifetime
- 1997-06-11 HU HU9901631A patent/HU227980B1/hu unknown
- 1997-06-11 JP JP50119798A patent/JP4018751B2/ja not_active Expired - Lifetime
- 1997-06-11 AT AT97925993T patent/ATE210630T1/de not_active IP Right Cessation
- 1997-06-11 DE DE69709044T patent/DE69709044T2/de not_active Expired - Lifetime
- 1997-06-11 CZ CZ1998399A patent/CZ293956B6/cs not_active IP Right Cessation
- 1997-06-11 WO PCT/EP1997/003021 patent/WO1997047590A2/en active IP Right Grant
- 1997-06-11 AU AU30945/97A patent/AU3094597A/en not_active Abandoned
- 1997-06-11 IL IL12325997A patent/IL123259A/xx not_active IP Right Cessation
- 1997-06-11 CN CN97190690A patent/CN1089335C/zh not_active Expired - Lifetime
- 1997-06-12 ZA ZA9705203A patent/ZA975203B/xx unknown
- 1997-06-12 US US08/873,771 patent/US5849953A/en not_active Expired - Lifetime
- 1997-06-13 IN IN1291MA1997 patent/IN182809B/en unknown
-
1998
- 1998-02-11 NO NO19980594A patent/NO324342B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO324342B1 (no) | 2007-09-24 |
| EP0851854A2 (en) | 1998-07-08 |
| JP4018751B2 (ja) | 2007-12-05 |
| US5849953A (en) | 1998-12-15 |
| CN1195338A (zh) | 1998-10-07 |
| HUP9901631A3 (en) | 2001-02-28 |
| IT1288114B1 (it) | 1998-09-10 |
| NO980594L (no) | 1998-04-07 |
| WO1997047590A2 (en) | 1997-12-18 |
| ITMI961204A0 (hu) | 1996-06-13 |
| DE69709044D1 (de) | 2002-01-24 |
| JPH11510827A (ja) | 1999-09-21 |
| CZ39998A3 (cs) | 1998-07-15 |
| ITMI961204A1 (it) | 1997-12-13 |
| ATE210630T1 (de) | 2001-12-15 |
| HU227980B1 (en) | 2012-07-30 |
| PT851854E (pt) | 2002-06-28 |
| ZA975203B (en) | 1998-01-20 |
| DE69709044T2 (de) | 2002-08-22 |
| IL123259A0 (en) | 1998-09-24 |
| ES2165610T3 (es) | 2002-03-16 |
| CZ293956B6 (cs) | 2004-08-18 |
| CN1089335C (zh) | 2002-08-21 |
| NO980594D0 (no) | 1998-02-11 |
| AU3094597A (en) | 1998-01-07 |
| IN182809B (hu) | 1999-07-24 |
| EP0851854B1 (en) | 2001-12-12 |
| IL123259A (en) | 2000-07-16 |
| WO1997047590A3 (en) | 1998-04-02 |
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