EA021074B1 - Способ получения севеламера гидрохлорида и севеламера карбоната/бикарбоната - Google Patents
Способ получения севеламера гидрохлорида и севеламера карбоната/бикарбоната Download PDFInfo
- Publication number
- EA021074B1 EA021074B1 EA201101613A EA201101613A EA021074B1 EA 021074 B1 EA021074 B1 EA 021074B1 EA 201101613 A EA201101613 A EA 201101613A EA 201101613 A EA201101613 A EA 201101613A EA 021074 B1 EA021074 B1 EA 021074B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- sevelamer
- polyallylamine
- hydrochloride
- epichlorohydrin
- bicarbonate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- KHNXRSIBRKBJDI-UHFFFAOYSA-N Sevelamer hydrochloride Chemical compound Cl.NCC=C.ClCC1CO1 KHNXRSIBRKBJDI-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229960003027 sevelamer hydrochloride Drugs 0.000 title claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 title claims abstract description 9
- PADGNZFOVSZIKZ-UHFFFAOYSA-N 2-(chloromethyl)oxirane;hydrogen carbonate;prop-2-enylazanium Chemical compound NCC=C.OC(O)=O.ClCC1CO1 PADGNZFOVSZIKZ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229960005441 sevelamer carbonate Drugs 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 229960003693 sevelamer Drugs 0.000 claims abstract description 23
- ZNSIZMQNQCNRBW-UHFFFAOYSA-N sevelamer Chemical compound NCC=C.ClCC1CO1 ZNSIZMQNQCNRBW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920000083 poly(allylamine) Polymers 0.000 claims description 24
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 102000006335 Phosphate-Binding Proteins Human genes 0.000 claims description 3
- 108010058514 Phosphate-Binding Proteins Proteins 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims description 3
- 230000008961 swelling Effects 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims 1
- 229920001577 copolymer Chemical compound 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001728 nano-filtration Methods 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011346 highly viscous material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- -1 alkaline earth metal carbonates Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000010000 carbonizing Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000009296 electrodeionization Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 201000005991 hyperphosphatemia Diseases 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A000816A IT1394299B1 (it) | 2009-05-12 | 2009-05-12 | Procedimento per la preparazione di sevelamer |
| PCT/IB2010/001071 WO2010131092A1 (en) | 2009-05-12 | 2010-05-10 | Process for the preparation of sevelamer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201101613A1 EA201101613A1 (ru) | 2012-04-30 |
| EA021074B1 true EA021074B1 (ru) | 2015-03-31 |
Family
ID=41257151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201101613A EA021074B1 (ru) | 2009-05-12 | 2010-05-10 | Способ получения севеламера гидрохлорида и севеламера карбоната/бикарбоната |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20120101234A1 (enExample) |
| EP (1) | EP2430078B1 (enExample) |
| JP (1) | JP5658744B2 (enExample) |
| CY (1) | CY1114915T1 (enExample) |
| DK (1) | DK2430078T3 (enExample) |
| EA (1) | EA021074B1 (enExample) |
| ES (1) | ES2453114T3 (enExample) |
| HR (1) | HRP20140241T1 (enExample) |
| IT (1) | IT1394299B1 (enExample) |
| PL (1) | PL2430078T3 (enExample) |
| PT (1) | PT2430078E (enExample) |
| SI (1) | SI2430078T1 (enExample) |
| WO (1) | WO2010131092A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101853260B1 (ko) * | 2016-11-29 | 2018-06-14 | 주식회사 퍼슨 | 세벨라머 카보네이트의 제조방법 |
| US10479865B2 (en) * | 2017-11-01 | 2019-11-19 | Strides Shasun Limited | Process for the preparation of sevelamer carbonate |
| CN115260355A (zh) * | 2022-05-16 | 2022-11-01 | 江苏中天药业有限公司 | 一种阴离子交换树脂、其制备方法、该树脂与药物的复合物和其掩味制剂 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223222A2 (en) * | 1985-11-19 | 1987-05-27 | W.R. Grace AB | Water soluble thermosetting resin, process for its production, paper sizing composition and paper sizing process |
| WO1998057652A1 (en) * | 1997-06-18 | 1998-12-23 | Geltex Pharmaceuticals, Inc. | Polyallylamine polymers for treating hypercholesterolemia |
| WO2000063259A1 (en) * | 1999-04-16 | 2000-10-26 | Abbott Laboratories | Process for producing cross-linked polyallylamine hydrochloride |
| WO2001018072A1 (en) * | 1999-09-03 | 2001-03-15 | The Dow Chemical Company | Process for producing cross-linked polyallylamine polymer |
| US20030078366A1 (en) * | 2001-10-09 | 2003-04-24 | Genzyme Corporation | Process for purification and drying of polymer hydrogels |
| WO2008062437A2 (en) * | 2006-09-01 | 2008-05-29 | Usv Limited | Process for the preparation of sevelamer hydrochloride and formulation thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6362266B1 (en) * | 1999-09-03 | 2002-03-26 | The Dow Chemical Company | Process for reducing cohesiveness of polyallylamine polymer gels during drying |
| WO2004037274A1 (en) * | 2002-10-22 | 2004-05-06 | Genzyme Corporation | Amine polymers for promoting bone formation |
| US7459502B2 (en) * | 2003-11-03 | 2008-12-02 | Ilypsa, Inc. | Pharmaceutical compositions comprising crosslinked polyamine polymers |
| JP2005138540A (ja) * | 2003-11-10 | 2005-06-02 | Konica Minolta Photo Imaging Inc | インクジェット記録材料 |
| JP2009542653A (ja) * | 2006-07-05 | 2009-12-03 | ジェンザイム コーポレーション | リン酸塩過剰血症のための鉄（ｉｉ）含有治療剤 |
-
2009
- 2009-05-12 IT ITMI2009A000816A patent/IT1394299B1/it active
-
2010
- 2010-05-10 DK DK10727834.3T patent/DK2430078T3/en active
- 2010-05-10 JP JP2012510378A patent/JP5658744B2/ja not_active Expired - Fee Related
- 2010-05-10 PL PL10727834T patent/PL2430078T3/pl unknown
- 2010-05-10 EA EA201101613A patent/EA021074B1/ru not_active IP Right Cessation
- 2010-05-10 SI SI201030544T patent/SI2430078T1/sl unknown
- 2010-05-10 ES ES10727834.3T patent/ES2453114T3/es active Active
- 2010-05-10 HR HRP20140241AT patent/HRP20140241T1/hr unknown
- 2010-05-10 PT PT107278343T patent/PT2430078E/pt unknown
- 2010-05-10 WO PCT/IB2010/001071 patent/WO2010131092A1/en not_active Ceased
- 2010-05-10 EP EP10727834.3A patent/EP2430078B1/en not_active Not-in-force
- 2010-05-10 US US13/319,821 patent/US20120101234A1/en not_active Abandoned
-
2014
- 2014-02-06 US US14/173,898 patent/US9303105B2/en not_active Expired - Fee Related
- 2014-02-27 CY CY20141100161T patent/CY1114915T1/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223222A2 (en) * | 1985-11-19 | 1987-05-27 | W.R. Grace AB | Water soluble thermosetting resin, process for its production, paper sizing composition and paper sizing process |
| WO1998057652A1 (en) * | 1997-06-18 | 1998-12-23 | Geltex Pharmaceuticals, Inc. | Polyallylamine polymers for treating hypercholesterolemia |
| WO2000063259A1 (en) * | 1999-04-16 | 2000-10-26 | Abbott Laboratories | Process for producing cross-linked polyallylamine hydrochloride |
| WO2001018072A1 (en) * | 1999-09-03 | 2001-03-15 | The Dow Chemical Company | Process for producing cross-linked polyallylamine polymer |
| US20030078366A1 (en) * | 2001-10-09 | 2003-04-24 | Genzyme Corporation | Process for purification and drying of polymer hydrogels |
| WO2008062437A2 (en) * | 2006-09-01 | 2008-05-29 | Usv Limited | Process for the preparation of sevelamer hydrochloride and formulation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2430078A1 (en) | 2012-03-21 |
| SI2430078T1 (sl) | 2014-04-30 |
| EP2430078B1 (en) | 2014-01-01 |
| EA201101613A1 (ru) | 2012-04-30 |
| JP2012526887A (ja) | 2012-11-01 |
| ES2453114T3 (es) | 2014-04-04 |
| DK2430078T3 (en) | 2014-03-24 |
| CY1114915T1 (el) | 2016-12-14 |
| IT1394299B1 (it) | 2012-06-06 |
| US20120101234A1 (en) | 2012-04-26 |
| ITMI20090816A1 (it) | 2010-11-13 |
| PT2430078E (pt) | 2014-02-11 |
| WO2010131092A1 (en) | 2010-11-18 |
| PL2430078T3 (pl) | 2014-06-30 |
| JP5658744B2 (ja) | 2015-01-28 |
| US20140213736A1 (en) | 2014-07-31 |
| HRP20140241T1 (hr) | 2014-04-11 |
| US9303105B2 (en) | 2016-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |