US20120101234A1 - Process for the preparation of sevelamer - Google Patents
Process for the preparation of sevelamer Download PDFInfo
- Publication number
- US20120101234A1 US20120101234A1 US13/319,821 US201013319821A US2012101234A1 US 20120101234 A1 US20120101234 A1 US 20120101234A1 US 201013319821 A US201013319821 A US 201013319821A US 2012101234 A1 US2012101234 A1 US 2012101234A1
- Authority
- US
- United States
- Prior art keywords
- sevelamer
- process according
- polyallylamine
- epichlorohydrin
- bicarbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 36
- ZNSIZMQNQCNRBW-UHFFFAOYSA-N sevelamer Chemical compound NCC=C.ClCC1CO1 ZNSIZMQNQCNRBW-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229960003693 sevelamer Drugs 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- PADGNZFOVSZIKZ-UHFFFAOYSA-N 2-(chloromethyl)oxirane;hydrogen carbonate;prop-2-enylazanium Chemical compound NCC=C.OC(O)=O.ClCC1CO1 PADGNZFOVSZIKZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229960005441 sevelamer carbonate Drugs 0.000 claims abstract description 9
- 229920000083 poly(allylamine) Polymers 0.000 claims description 26
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical group NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 11
- 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
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- KHNXRSIBRKBJDI-UHFFFAOYSA-N Sevelamer hydrochloride Chemical compound Cl.NCC=C.ClCC1CO1 KHNXRSIBRKBJDI-UHFFFAOYSA-N 0.000 abstract description 7
- 229960003027 sevelamer hydrochloride Drugs 0.000 abstract description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 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 8
- 150000003839 salts Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 238000001728 nano-filtration Methods 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 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
- 239000000463 material Substances 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
- 238000005406 washing Methods 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- AQGXJVKWSPKOHF-UHFFFAOYSA-N CCC(CN)CC(C)CNCC(O)CNCC(C)CC(CC)CN Chemical compound CCC(CN)CC(C)CNCC(O)CNCC(C)CC(CC)CN AQGXJVKWSPKOHF-UHFFFAOYSA-N 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 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
- 239000012530 fluid Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940020428 renagel Drugs 0.000 description 1
- 229940047681 renvela Drugs 0.000 description 1
- 239000000126 substance Substances 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
Definitions
- Sevelamer or poly(allylamine-co-N,N′-diallyl-1,3-diamino-2-hydroxypropane), is a polymer compound having the formula
- Sevelamer is marketed as the hydrochloride salt under the trade name Renagel® for controlling hyperphosphatemia (increase in the level of phosphates in the blood) in adult patients undergoing dialysis or hemodialysis.
- Renagel® the sevelamer carbonate/bicarbonate salt
- Polyallylamine is a polymer compound known in the art with the CAS RN 71550-12-4 and is obtained by allylamine polymerization.
- U.S. Pat. No. 6,180,754 in the name of The Dow Chemical Company describes a process for the synthesis of sevelamer that provides for the use of a LIST reactor to perform the cross-linking step.
- This reactor produced by the company LIST Inc., is a reactor specifically designed for processing high viscosity materials. It is easily understood that this reactor is not commonly used and that its use requires specific and economically important investments, unjustified for the preparation of a single active ingredient.
- the patent application WO01/18072 describes a process for the preparation of sevelamer hydrochloride comprising partial salification of a solution of polyallylamine hydrochloride, removal of salts through ion exchange or electrodeionization and by means of subsequent optional nanofiltration or ultrafiltration of the partially desalified polyallylamine, and then causing it to react with epichlorohydrin.
- WO01/18072 for example pages 4 and 5
- a substantial quantity of salts is produced during desalification of the polyallylamine hydrochloride with metal hydroxides a substantial quantity of salts is produced.
- the aim of the present invention is to provide a process for the preparation of sevelamer which overcomes the drawbacks of the prior art.
- the invention relates to a process for the preparation of sevelamer which comprises partially salifying, preferably with hydrochloric acid, a polyallylamine aqueous solution having a concentration between 10% and 14.5% (w/w) and reacting it with epichlorohydrin, in the absence of any organic solvents.
- the invention relates to a process comprising the steps of:
- the polyallylamine is partially salified with hydrochloric acid and the sevelamer obtained in step (d) is sevelamer hydrochloride.
- the initial polyallylamine aqueous solution is commercially available. This polyallylamine can be suitably diluted with water to the desired concentration.
- the concentration of the polyallylamine aqueous solution is between 11% and 14.5%, preferably between 12.5 and 14.5%, advantageously this concentration is around 13-14%.
- the epichlorohydrin used according to the present invention is also commercially available.
- the polyallylamine aqueous solution is loaded into a common reactor, hydrochloric acid is added to reach the degree of salification required and epichlorohydrin is dosed, preferably controlling the temperature as the reaction is exothermic.
- the temperature of the reaction mixture is maintained around 20-25° C. during the step of acid addition.
- the quantity of acid to add to the polyallylamine depends on the degree of salification required.
- the polyallylamine is salified to 25-40%, for example around 30-35%. Therefore, by way of example, salification can be achieved using a “allylamine unit”/“hydrochloric acid” molar ratio of around 3-3.5/1.
- the hydrochloric acid is preferably added in an aqueous solution.
- the “allylamine unit”/“epichlorohydrin” ratio is advantageously around 8-11/1, preferably around 9/1.
- the mixture is maintained under stirring for some time, for example a few hours, and the reaction mixture is then heated to a temperature between 65 and 85° C., preferably between 75 and 83° C.
- the cross-linking reaction is normally complete in a few hours.
- the sevelamer obtained according to the process of the invention can be directly filtered and dried according to methods known in the art.
- a water miscible solvent advantageously isopropanol
- isopropanol can be added to the reaction mass and maintained under stirring for some time, and the sevelamer thus obtained can then be filtered and dried.
- the sevelamer obtained with the process described above can be converted into sevelamer carbonate/bicarbonate according to known techniques, for example by reaction with gaseous carbon dioxide or other carbonating agents, such as carbonates of alkaline or alkaline-earth metals.
- reaction can be conducted in a basic aqueous solvent, such as in a sodium hydroxide solution or also in solid phase, i.e. without using solvents.
- a basic aqueous solvent such as in a sodium hydroxide solution or also in solid phase, i.e. without using solvents.
- PAA Solution PAA PAA (mol HCl washing 14.0% 100% allylamine epichlorohydrin epichlorohydrin HCl 38.2% isopropanol (g) (g) units) (mol) (g) (mol) (g) (g) 16650 2344 41.1 4.6 426.5 11.9 1137 14630
- a conventional reactor, with blade stirrer, is used.
- HCl is added to the polyallylamine loaded into the reactor in two batches dosed at a distance of 15 minutes.
- dosing of epichlorohydrin begins and continues for around 10 minutes.
- heating to 78° C.-83° C. begins and continues for 3 hours, at the end of which the product, after cooling to room temperature, is washed with isopropanol. Washing is performed by maintaining the product under stirring with isopropanol for 1 hour, then the product is centrifuged and vacuum dried at 60° C. for 3 hours, finally obtaining 2.94 kg of product in the form of a whitish solid.
- the analytical evaluations are performed according to methods known in the art and conventionally used for sevelamer.
- PAA PAA PAA (mol epi- epi- HCl Solution 100% allylamine chlorohydrin chlorohydrin HCl 38.2% 30% (g) (g) units) (mol) (g) (mol) (g) 483.5 145 2.54 0.28 26 0.79 77.5
- example 1 The process of example 1 is repeated. After adding one part of epichlorohydrin a vitreous and intractable gel is obtained, which blocked stirring.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A000816A IT1394299B1 (it) | 2009-05-12 | 2009-05-12 | Procedimento per la preparazione di sevelamer |
| ITMI2009A000816 | 2009-05-12 | ||
| PCT/IB2010/001071 WO2010131092A1 (en) | 2009-05-12 | 2010-05-10 | Process for the preparation of sevelamer |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2010/001071 A-371-Of-International WO2010131092A1 (en) | 2009-05-12 | 2010-05-10 | Process for the preparation of sevelamer |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/173,898 Continuation US9303105B2 (en) | 2009-05-12 | 2014-02-06 | Process for the preparation of sevelamer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20120101234A1 true US20120101234A1 (en) | 2012-04-26 |
Family
ID=41257151
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13/319,821 Abandoned US20120101234A1 (en) | 2009-05-12 | 2010-05-10 | Process for the preparation of sevelamer |
| US14/173,898 Expired - Fee Related US9303105B2 (en) | 2009-05-12 | 2014-02-06 | Process for the preparation of sevelamer |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/173,898 Expired - Fee Related US9303105B2 (en) | 2009-05-12 | 2014-02-06 | Process for the preparation of sevelamer |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20120101234A1 (https=) |
| EP (1) | EP2430078B1 (https=) |
| JP (1) | JP5658744B2 (https=) |
| CY (1) | CY1114915T1 (https=) |
| DK (1) | DK2430078T3 (https=) |
| EA (1) | EA021074B1 (https=) |
| ES (1) | ES2453114T3 (https=) |
| HR (1) | HRP20140241T1 (https=) |
| IT (1) | IT1394299B1 (https=) |
| PL (1) | PL2430078T3 (https=) |
| PT (1) | PT2430078E (https=) |
| SI (1) | SI2430078T1 (https=) |
| WO (1) | WO2010131092A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101853260B1 (ko) * | 2016-11-29 | 2018-06-14 | 주식회사 퍼슨 | 세벨라머 카보네이트의 제조방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180754B1 (en) * | 1999-09-03 | 2001-01-30 | The Dow Chemical Company | Process for producing cross-linked polyallylamine polymer |
| US7220406B2 (en) * | 2002-10-22 | 2007-05-22 | Genzyme Corporation | Method for promoting bone formation |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3541511A1 (de) * | 1985-11-19 | 1987-05-21 | Grace W R Ab | Promoter fuer die papierleimung, verfahren zu dessen herstellung und dessen verwendung |
| US6423754B1 (en) * | 1997-06-18 | 2002-07-23 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with polyallylamine polymers |
| WO2000063259A1 (en) * | 1999-04-16 | 2000-10-26 | Abbott Laboratories | Process for producing cross-linked polyallylamine hydrochloride |
| US6362266B1 (en) * | 1999-09-03 | 2002-03-26 | The Dow Chemical Company | Process for reducing cohesiveness of polyallylamine polymer gels during drying |
| US6600011B2 (en) * | 2001-10-09 | 2003-07-29 | Genzyme Corporation | Process for purification and drying of polymer hydrogels |
| 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 |
| WO2008005217A2 (en) * | 2006-07-05 | 2008-01-10 | Genzyme Corporation | Iron(ii)-containing treatments for hyperphosphatemia |
| CA2749074A1 (en) * | 2006-09-01 | 2008-05-29 | Usv Limited | Process for the preparation of sevelamer hydrochloride and formulation thereof |
-
2009
- 2009-05-12 IT ITMI2009A000816A patent/IT1394299B1/it active
-
2010
- 2010-05-10 SI SI201030544T patent/SI2430078T1/sl unknown
- 2010-05-10 PT PT107278343T patent/PT2430078E/pt unknown
- 2010-05-10 PL PL10727834T patent/PL2430078T3/pl unknown
- 2010-05-10 HR HRP20140241AT patent/HRP20140241T1/hr unknown
- 2010-05-10 EP EP10727834.3A patent/EP2430078B1/en not_active Not-in-force
- 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 WO PCT/IB2010/001071 patent/WO2010131092A1/en not_active Ceased
- 2010-05-10 EA EA201101613A patent/EA021074B1/ru not_active IP Right Cessation
- 2010-05-10 US US13/319,821 patent/US20120101234A1/en not_active Abandoned
- 2010-05-10 ES ES10727834.3T patent/ES2453114T3/es active Active
-
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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6180754B1 (en) * | 1999-09-03 | 2001-01-30 | The Dow Chemical Company | Process for producing cross-linked polyallylamine polymer |
| US7220406B2 (en) * | 2002-10-22 | 2007-05-22 | Genzyme Corporation | Method for promoting bone formation |
Non-Patent Citations (1)
| Title |
|---|
| Chemistry, The Central Science; Brown, LeMay and Bursten; 7th Edition; Page 126 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| PT2430078E (pt) | 2014-02-11 |
| JP2012526887A (ja) | 2012-11-01 |
| EA021074B1 (ru) | 2015-03-31 |
| EA201101613A1 (ru) | 2012-04-30 |
| PL2430078T3 (pl) | 2014-06-30 |
| IT1394299B1 (it) | 2012-06-06 |
| WO2010131092A1 (en) | 2010-11-18 |
| SI2430078T1 (sl) | 2014-04-30 |
| DK2430078T3 (en) | 2014-03-24 |
| US9303105B2 (en) | 2016-04-05 |
| JP5658744B2 (ja) | 2015-01-28 |
| ES2453114T3 (es) | 2014-04-04 |
| HRP20140241T1 (hr) | 2014-04-11 |
| ITMI20090816A1 (it) | 2010-11-13 |
| CY1114915T1 (el) | 2016-12-14 |
| EP2430078A1 (en) | 2012-03-21 |
| US20140213736A1 (en) | 2014-07-31 |
| EP2430078B1 (en) | 2014-01-01 |
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