WO2000063259A1 - Process for producing cross-linked polyallylamine hydrochloride - Google Patents

Process for producing cross-linked polyallylamine hydrochloride Download PDF

Info

Publication number
WO2000063259A1
WO2000063259A1 PCT/US2000/010167 US0010167W WO0063259A1 WO 2000063259 A1 WO2000063259 A1 WO 2000063259A1 US 0010167 W US0010167 W US 0010167W WO 0063259 A1 WO0063259 A1 WO 0063259A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
cross
polyallylamine
hydroxide
reaction mixture
Prior art date
Application number
PCT/US2000/010167
Other languages
French (fr)
Inventor
Russell C. Klix
Jufang H. Barkalow
William T. Monte
Original Assignee
Abbott Laboratories
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Abbott Laboratories filed Critical Abbott Laboratories
Priority to JP2000612344A priority Critical patent/JP4634618B2/en
Priority to DK00923393T priority patent/DK1175451T3/en
Priority to MXPA01010454A priority patent/MXPA01010454A/en
Priority to EP00923393A priority patent/EP1175451B1/en
Priority to DE60035414T priority patent/DE60035414T2/en
Priority to CA002362410A priority patent/CA2362410A1/en
Publication of WO2000063259A1 publication Critical patent/WO2000063259A1/en

Links

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
    • C08F8/00—Chemical modification by after-treatment

Definitions

  • the present invention relates to a process for preparing a functionalized polymer.
  • the present invention relates to a process for preparing cross-linked
  • Functionalized polymers find many uses in the art such as drugs, ion exchange
  • a functionalized polymer should be one that is capable of containing
  • the polymer will contain electrophilic or
  • nucleophilic functional groups An example of a polymer having an electrophilic
  • nucleophilic functional groups include polyacrylic acid wherein the functional group is -
  • the method involves dispersing a solution of
  • the liquid medium is usually an halogenated or unhalogenated aliphatic or
  • aromatic hydrocarbon such as carbon tetrachloride. trichlorethylene. dichloromethane.
  • hydrocarbons for use as the liquid medium.
  • Such hydrocarbons mav ⁇
  • the 701 patent is that the polymerization process results in a voluminous batch due to the
  • the present invention relates to a solution process for preparing a functionalized
  • the present invention involves a process for preparing cross-
  • the present invention relates to a solution process for producing cross-linked
  • the solution process of the present invention involves adding polyallylamine
  • reaction vessel forms a reaction mixture.
  • polyallylamine hydrochloride preferably has a molecular weight of from about 1000 to
  • hydrochloride is commercially available from Nitto Boseki Company. LTD.. Tokyo. Japan
  • polyallylamine hydrochloride can be synthesized from monoallylamine and concentrated hydrochloric acid as described in
  • the polyallylamine used in the process of the present invention can be in any form
  • Solid forms of polyallylamine may be
  • hydrochloride salt form may be illustrative of the present invention.
  • the polyallylamine hydrochloride is added to the reaction vessel in the form of
  • aqueous is from about 25% to about 75% aqueous, preferably about 50% aqueous.
  • the water added to the reaction vessel is preferably distilled water.
  • ratio of water (kg) to poUyallylamine hydrochloride (kg, dry weight) is from about 1.5: 1.0
  • reaction mixture is mixed for a time period of from about 15 minutes to about
  • hydroxides examples include potassium hydroxide,
  • alkoxides that can be used in the process of the present invention are sodium methoxide.
  • sodium ethoxide sodium tert-butoxide, potassium methoxide. potassium ethoxide.
  • polyallylamine hydrochloride (kg. dry weight) is from about 0.1 : 1.0 to about 10.0: 1.0.
  • reaction mixture preferably from about 0.3: 1.0 to about 5.0: 1.0.
  • reaction mixture is allowed to cool to a temperature of from about 15°C to
  • the solvent displaces the water out of the polallylamine particles to
  • the water-miscible solvent can be an aprotic or a protic
  • Water-miscible aprotic or protic solvents that can be used in this invention are
  • miscible aprotic solvent that can be used in the process of the present invention is
  • Alcohols suitable for the present invention include
  • protic solvent that can be used in the process of the present invention is isopropanol.
  • volume ratio of water-miscible solvent to water in the reaction mixture may be from about
  • aprotic and protic solvents may be used
  • the hydroxide or alkoxide may be added to the reaction vessel first followed by addition of polyallylamine, water, and solvent.
  • polyallylamine for example, the polyallylamine. water, and solvent.
  • hydroxide or alkoxide hydroxide or alkoxide, and solvent or co-solvents must be added prior to the addition of
  • the cross-linking agent can be any compound that contains at least two
  • hydrochloride As used herein, the term "functional group" refers to the center of reactivity
  • the functional groups contained in the cross-linking agent can be halogen
  • cross-linking agent can be epichlorohydrin or l,3-dichloro-2-propanol.
  • linking agent or multiple cross-linking agents can be used in the process of the present
  • linking agent to polyallylamine hydrochloride in the reaction mixture is from about
  • reaction mixture may be stirred and the reaction mixture begins to form a suspension of
  • the suspension of particles may be any suitable poyallylamine particles. After completion of the stirring, the suspension of particles may be any suitable poyallylamine particles. After completion of the stirring, the suspension of particles may be any suitable poyallylamine particles.
  • reaction vessel may then be washed with a water-miscible
  • organic solvent such as acetonitrile or isopropanol. in order to remove any residual solids.
  • the collected solids can then be washed with distilled water and a water-miscible organic
  • Any water-miscible solvent can be used such as acetonitrile or isopropanol.
  • solids can then be dried using any technique known in the art.
  • the solids can be dried under a vacuum. After drying, a cross-linked polyallylamine hydrochloride is
  • cross-linked polyallylamine hydrochlorides of the present invention may be any cross-linked polyallylamine hydrochlorides of the present invention.
  • pharmacuetically acceptable cross-linked polyallylamine may be used to remove

Abstract

The present invention relates to a process for preparing a cross-linked pollyallylamine hydrochloride. The process involves mixing polyallylamine hydrochloride, water, a hydroxide or alkoxide, and a water-miscible organic solvent or co-solvents, to a reaction mixture and adding a cross-linking agent to the reaction mixture to form a cross-linked polyallylamine.

Description

PROCESS FOR PRODUCING CROSS-LINKED
POLYALLYLAMINE HYDROCHLORIDE
Technical Field of the Invention
The present invention relates to a process for preparing a functionalized polymer.
More specifically, the present invention relates to a process for preparing cross-linked
polyallylamine hydrochloride.
Background of the Invention
Functionalized polymers find many uses in the art such as drugs, ion exchange
resins and chelating resins. Functionalized polymers are prepared by introducing various
types of functional groups into insoluble polymers. The polymer to be used as a base for
the production of a functionalized polymer should be one that is capable of containing
several different types of functional groups that are capable of reacting with many
different kinds of compounds. Preferably, the polymer will contain electrophilic or
nucleophilic functional groups. An example of a polymer having an electrophilic
functional group is chloromethylated polystyrene. Examples of polymers having
nucleophilic functional groups include polyacrylic acid wherein the functional group is -
COOH, polyvinyl alcohol wherein the functional group is -OH. polyethyleneimine
wherein the functional group is -NH-. polyvinylamine wherein the functional group is -
NF -, and the like. U.S. Patent 4.605.701 (the 701 patent) describes a process for preparing a cross-
linked monoallylamine polymer. The method involves dispersing a solution of
monoallylamine polymer in an aqueous solvent and then into a liquid medium that is
immiscible with the aqueous solvent. This is followed by subjecting some of the amino
groups present in the polymer to a crosslinking reaction with formaldehyde or a compound
having at least two functional groups reactive with the primary amino group. According to
the 701 patent, the liquid medium is usually an halogenated or unhalogenated aliphatic or
aromatic hydrocarbon such as carbon tetrachloride. trichlorethylene. dichloromethane.
tetrachloroethylene, chlorobenzene. dichlorobenzene, benzene, toluene, xylene and the
like.
One of the difficulties with the process for preparing a cross-linked
monoallylamine polymer as described in the 701 patent is that this process employs
aliphatic or aromatic hydrocarbons for use as the liquid medium. Such hydrocarbons mav¬
be hazardous and expensive to dispose of. Another difficulty with the process described in
the 701 patent is that the polymerization process results in a voluminous batch due to the
swelling of the gel and necessitates the use of a number of reaction vessels making the
process difficult and expensive.
Therefore, there is a need in the art for a solution process of preparing cross-linked
functional polymers, such as polyallylamine hydrochloride. in which the process employs
environmentally friendly materials and the polymerization occurs in a single reaction
vessel in order to facilitate commercial production of the polymer. The present invention relates to a solution process for preparing a functionalized
polymer. More specifically, the present invention involves a process for preparing cross-
linked polyallylamine hydrochlorides using environmentally preferable materials. The
process of the present invention does not employ aliphatic or aromatic hydrocarbons that
may be hazardous and expensive to dispose of. The process of the present invention
controls the swelling of the cross-linked polyallylamine polymer in a single reaction
vessel that facilitates commercial production of the polymer.
Summary of the Invention
The present invention relates to a solution process for producing cross-linked
polyallylamine and its salts. In particular, the process of the present invention involves
mixing polyallylamine hydrochloride, water, a hydroxide or alkoxide, and a water-
miscible organic solvent or co-solvents, in a reaction vessel, and then adding a cross-
linking agent.
Detailed Description of the Invention
The solution process of the present invention involves adding polyallylamine
and/or its salt forms and water to a reaction vessel to form a reaction mixture. The
polyallylamine hydrochloride preferably has a molecular weight of from about 1000 to
about 500.000, more preferably from about 5,000 to about 30.000. Polyallylamine
hydrochloride is commercially available from Nitto Boseki Company. LTD.. Tokyo. Japan
and Salbury Chemical. Inc.. Charles City. Iowa. Also, polyallylamine hydrochloride can be synthesized from monoallylamine and concentrated hydrochloric acid as described in
U.S. Patent 4.605,701. herein incorporated by reference.
The polyallylamine used in the process of the present invention can be in any form
known in the art. such as in solid or aqueous form. Solid forms of polyallylamine may be
reconstituted with water. Various salt forms of polyallylamine may be used as well, and in
particular, the hydrochloride salt form may be illustrative of the present invention.
Preferably, the polyallylamine hydrochloride is added to the reaction vessel in the form of
an aqueous solution. When an aqueous solution of polyallylamine hydrochloride is used, it
is from about 25% to about 75% aqueous, preferably about 50% aqueous.
The water added to the reaction vessel is preferably distilled water. The weight
ratio of water (kg) to poUyallylamine hydrochloride (kg, dry weight) is from about 1.5: 1.0
to about 10.0:1.0, preferably from about 1.5:1 :0 to about 5.0:1.0.
After the poUyallylamine hydrochloride and water are added to the reaction vessel,
the resulting reaction mixture is mixed for a time period of from about 15 minutes to about
90 minutes. After the mixing, a hydroxide or alkoxide is added to reaction mixture.
Examples of hydroxides that can be used in the present invention are potassium hydroxide,
calcium hydroxide, sodium hydroxide, lithium hydroxide, and the like. Examples of
alkoxides that can be used in the process of the present invention are sodium methoxide.
sodium ethoxide. sodium tert-butoxide, potassium methoxide. potassium ethoxide.
potassium tert-butoxide, and the like. The weight ratio of hydroxide or alkoxide (kg) to
polyallylamine hydrochloride (kg. dry weight) is from about 0.1 : 1.0 to about 10.0: 1.0.
preferably from about 0.3: 1.0 to about 5.0: 1.0. After the hydroxide or alkoxide is added to the reaction mixture, the reaction
mixture is stirred for a time period of from about 30 minutes to about 120 minutes. After
stirring, the reaction mixture is allowed to cool to a temperature of from about 15°C to
about 40°C, preferably from about 20°C to about 30°C.
After the reaction mixture has cooled, a water-miscible organic solvent is added to
the reaction mixture. The solvent displaces the water out of the polallylamine particles to
allow for further processing. The water-miscible solvent can be an aprotic or a protic
solvent. Water-miscible aprotic or protic solvents that can be used in this invention are
well known in the art and include, but are not intended to be limited to. alcohols,
dimethylformamide, tetrahydrofuran, dimethyl sulfoxide, acetonitrile. A prefered water-
miscible aprotic solvent that can be used in the process of the present invention is
acetonitrile. A preferred water-miscible protic solvent that can be used in the process of
the present invention is alcohol. Alcohols suitable for the present invention include
isopropanol. methanol. ethanol. butanol, and the like. A more preferred water-miscible
protic solvent that can be used in the process of the present invention is isopropanol. The
volume ratio of water-miscible solvent to water in the reaction mixture may be from about
0.5:1.0 to about 10.0: 1.0. preferably from about 1.5: 1.0 to about 5.0: 1.0.
It is to be understood that co-solvents may be added to the reaction mixture instead
of the use of a single solvent. For example, aprotic and protic solvents may be used
together in the process to achieve the same purpose. Furthermore, the order of adding the
above reactants to the reaction mixture is not critical to the present invention. For
example, the hydroxide or alkoxide may be added to the reaction vessel first followed by addition of polyallylamine, water, and solvent. However, the polyallylamine. water,
hydroxide or alkoxide, and solvent or co-solvents must be added prior to the addition of
the cross-linking agent.
After the addition of the above reactants to the reaction mixture, a cross-linking
agent is added to the reaction mixture to cross-link the amino groups of the polyallylamine
hydrochloride. The cross-linking agent can be any compound that contains at least two
functional groups that are reactive with the amino groups of the polyallylamine
hydrochloride. As used herein, the term "functional group" refers to the center of reactivity
in a molecule. The functional groups contained in the cross-linking agent can be halogen
groups, epoxy groups, carboxyl groups, hydroxy groups and the like. For example, the
cross-linking agent can be epichlorohydrin or l,3-dichloro-2-propanol. A single cross-
linking agent or multiple cross-linking agents can be used in the process of the present
invention to cross-link the poUyallylamine hydrochloride. The weight ratio of cross-
linking agent to polyallylamine hydrochloride in the reaction mixture is from about
0.01 :1.0 to about 10.0:1.0. After the addition of the cross-linking agent, the reaction
mixture may be stirred and the reaction mixture begins to form a suspension of
poyallylamine particles. After completion of the stirring, the suspension of particles may
be recovered by filtering. The reaction vessel may then be washed with a water-miscible
organic solvent, such as acetonitrile or isopropanol. in order to remove any residual solids.
The collected solids can then be washed with distilled water and a water-miscible organic
solvent. Any water-miscible solvent can be used such as acetonitrile or isopropanol. The
solids can then be dried using any technique known in the art. For example, the solids can be dried under a vacuum. After drying, a cross-linked polyallylamine hydrochloride is
recovered.
The cross-linked polyallylamine hydrochlorides of the present invention may be
used to selectively bind phosphates, transition metals, ionic complexes, and the like. For
example, pharmacuetically acceptable cross-linked polyallylamine may be used to remove
phosphates in the lumen in patients suffering from renal failure.
Examplel: Preparation of a Cross-Linked Polyallylamine Hydrochloride
To a 30 gallon glass lined reactor was added 14.8 kg of polyallylamine
hydrochloride solution (50% aqueous) and 22.2 kg of distilled water. The contents were
mixed for about 15 minutes. To this solution was added 2.26 kg of sodium hydroxide and
the mixture was stirred for about 30 minutes until the sodium hydroxide was dissolved.
After the solution was allowed to cool to 20°C-30°C, 36.8 kg of acetonitrile followed by
696 grams of epichlorohydrin were added. The reaction mixture was then stirred for not
less than 21 hours at room temperature. A suspension of particles occurred at around 2
hours. The slurry was then filtered and the reactor was washed with 10 kg of acetonitrile to
remove any residual solids. The collected solid was washed with 109.8 kg of distilled
water and 249 kg of 70% aqueous isopropanol to obtain a final conductivity of 0.09 m
Siemen/cm. The product was then dried under a vacuum with a moist air bleed at 55°C to
afford 5.9 kg of the final product.

Claims

δWHAT IS CLAIMED IS:
1. A solution process for producing a cross-linked polyallylamine or a salt
form thereof, the process comprising the steps of.
a), mixing polyallylamine, water, a hydroxide or alkoxide, and a water-
miscible organic solvent or co-solvent; and
b). adding a cross-linking agent to form a cross-linked polyallylamine.
2. The process of claim 1 wherein the weight ratio of water to polyallylamine
in the reaction mixture is from about 1.5:1.0 to 10.0:1.0.
3. The process of claim 1 wherein the hydroxide is selected from the group
consisting of sodium hydroxide, calcium hydroxide, potassium hydroxide, and lithium
hydroxide.
4. The process of claim 1 wherein the alkoxide is selected from the group
consisting of sodium methoxide, sodium ethoxide, sodium tert-butoxide. potassium
methoxide. potassium ethoxide. and potassium tert-butoxide.
5. The process of claim 1 wherein the weight ratio of hydroxide or alkoxide to
poUyallylamine in the reaction mixture is from about 0.1 : 1.0 to about 10.0: 1.0.
6. The process of claim 1 wherein the water-miscible organic solvent is an
aprotic solvent.
7. The process of claim 1 wherein the cross-linked polyallylamine is
recovered by filtration.
8. The process of claim 6 wherein the water-miscible aprotic solvent is
acetonitrile.
9. The process of claim 1 wherein the water-miscible organic solvent is a
protic solvent.
10. The process of claim 9 wherein the water-miscible protic solvent is
isopropanol.
11. The process of claim 1 wherein the volume ratio of water-miscible organic
solvent to water in the reaction mixture is from about 0.5:1.0 to about 10.0:1.0.
12. The process of claim 1 wherein the cross-linking agent is a compound
which has at least two functional groups which are reactive with the amino groups of the
polyallylamine.
13. The process of claim 12 wherein the functional groups are selected from
halogen group, epoxy group, carboxyl group, or hydroxyl group.
14. The process of claim 12 wherein the cross-linking agent is selected from
the group consisting of epichlorohydrin and 1,3 dichloro-2-propanol.
15. The process of claim 1 wherein the weight ratio of cross-linking agent to
polyallylamine in the reaction mixture is from about 0.01 : 1.0 to about 10.0:1.0.
16. The process of claim 1 wherein the polyallylamine is the hydrochloride salt
form.
PCT/US2000/010167 1999-04-16 2000-04-14 Process for producing cross-linked polyallylamine hydrochloride WO2000063259A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2000612344A JP4634618B2 (en) 1999-04-16 2000-04-14 Method for producing crosslinked polyallylamine hydrochloride
DK00923393T DK1175451T3 (en) 1999-04-16 2000-04-14 Process for the preparation of crosslinked polyallylamine hydrochloride
MXPA01010454A MXPA01010454A (en) 1999-04-16 2000-04-14 Process for producing cross-linked polyallylamine hydrochloride.
EP00923393A EP1175451B1 (en) 1999-04-16 2000-04-14 Process for producing cross-linked polyallylamine hydrochloride
DE60035414T DE60035414T2 (en) 1999-04-16 2000-04-14 METHOD FOR PRODUCING NETWORKED POLYALLYAMINE DERIVATIVES
CA002362410A CA2362410A1 (en) 1999-04-16 2000-04-14 Process for producing cross-linked polyallylamine hydrochloride

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US29355199A 1999-04-16 1999-04-16
US09/293,551 1999-04-16

Publications (1)

Publication Number Publication Date
WO2000063259A1 true WO2000063259A1 (en) 2000-10-26

Family

ID=23129543

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/010167 WO2000063259A1 (en) 1999-04-16 2000-04-14 Process for producing cross-linked polyallylamine hydrochloride

Country Status (12)

Country Link
US (1) US6525113B2 (en)
EP (2) EP1175451B1 (en)
JP (1) JP4634618B2 (en)
AT (1) ATE366264T1 (en)
CA (1) CA2362410A1 (en)
CY (1) CY1109000T1 (en)
DE (1) DE60035414T2 (en)
DK (1) DK1175451T3 (en)
ES (1) ES2288852T3 (en)
MX (1) MXPA01010454A (en)
PT (1) PT1175451E (en)
WO (1) WO2000063259A1 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048209A1 (en) * 2000-12-13 2002-06-20 Dsm Fine Chemicals Austria Nfg Gmbh & Co. Kg Alkylation of cross-linked polymers containing n- or amino- or ammonium groups
US6600011B2 (en) 2001-10-09 2003-07-29 Genzyme Corporation Process for purification and drying of polymer hydrogels
US6710162B2 (en) 2001-02-16 2004-03-23 Genzyme Corporation Method of drying a material having a cohesive phase
WO2006097942A1 (en) * 2005-03-16 2006-09-21 Council Of Scientific And Industrial Research An improved process for the preparation of crosslinked polyallylamine polymer.
WO2010029579A3 (en) * 2008-09-15 2010-05-20 Shasun Chemicals And Drugs Ltd Non-aqueous solution process for the preparation of cross-linked polymers
ITMI20090816A1 (en) * 2009-05-12 2010-11-13 Chimico Internaz Spa Lab PROCEDURE FOR THE PREPARATION OF SEVELAMER
WO2011099038A2 (en) * 2010-02-15 2011-08-18 Sun Pharmaceutical Industries Limited Process for preparing crosslinked allylamine polymer
US11147833B2 (en) 2017-10-16 2021-10-19 Fujifilm Corporation Therapeutic agent for hyperphosphatemia
US11186685B2 (en) 2016-12-28 2021-11-30 Fujifilm Corporation Emulsion of nitrogen atom-containing polymer or salt thereof, production method therefor, and production method for particles

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4547620B2 (en) * 2004-12-02 2010-09-22 日東紡績株式会社 Method for producing crosslinked allylamine polymers
US7964182B2 (en) * 2006-09-01 2011-06-21 USV, Ltd Pharmaceutical compositions comprising phosphate-binding polymer
BRPI0717008A2 (en) * 2006-09-01 2014-01-21 Usv Ltd PROCESS FOR PREPARING SEVELAMER CHLORIDE AND FORMULATING IT
CN101687961B (en) * 2007-07-11 2011-10-05 东丽株式会社 Crosslinked polyallylamine or acid addition salt thereof, and use thereof for medical purposes
US8389640B2 (en) * 2008-04-15 2013-03-05 Lupin Limited Process for the preparation of cross-linked polyallylamine polymer
US8404784B2 (en) * 2008-12-03 2013-03-26 Navinta Llc Manufacturing process of making polymeric amine salts
US20110081413A1 (en) * 2009-01-22 2011-04-07 Ashok Omray Pharmaceutical Compositions Comprising Phosphate-Binding Polymer
AU2010261339A1 (en) 2009-06-16 2012-01-19 Watson Pharma Private Limited Processes for the preparation of sevelamer carbonate
WO2012042542A1 (en) 2010-10-01 2012-04-05 Usv Limited Process for preparation of crosslinked polymer
IT1404163B1 (en) 2011-02-01 2013-11-15 Chemi Spa PROCESS FOR THE PREPARATION OF RETICULATED POLYALLYLAMINS OR THEIR PHARMACEUTICAL ACCEPTABLE SALTS
KR101853260B1 (en) 2016-11-29 2018-06-14 주식회사 퍼슨 Process for preparation of sevelamer carbonate

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992345A (en) * 1973-08-31 1976-11-16 Hercules Incorporated Water-dispersible thermosettable cationic resins and paper sized therewith
EP0143328A2 (en) * 1983-10-25 1985-06-05 Nitto Boseki Co., Ltd. Small-flobular crosslinked monoallylamine polymer and process for producing the same
US4680360A (en) * 1983-11-14 1987-07-14 Nitto Boseki Co., Ltd Process for producing poly(allylamine) derivatives
US4698380A (en) * 1985-09-23 1987-10-06 Ethyl Corporation Fluid loss control in well cement slurries
WO1996039449A1 (en) * 1995-06-06 1996-12-12 Geltex Pharmaceuticals, Inc. Hydrophobic heteroatom-containing sequestrant for cholesterol depletion

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE914179A1 (en) * 1990-12-07 1992-06-17 Ici Plc Nitrogen derivatives
US5607669A (en) 1994-06-10 1997-03-04 Geltex Pharmaceuticals, Inc. Amine polymer sequestrant and method of cholesterol depletion
US5496545A (en) * 1993-08-11 1996-03-05 Geltex Pharmaceuticals, Inc. Phosphate-binding polymers for oral administration
JPH07309766A (en) * 1994-05-20 1995-11-28 Sekisui Chem Co Ltd Cholesterol lowering agent
TW474813B (en) 1994-06-10 2002-02-01 Geltex Pharma Inc Alkylated composition for removing bile salts from a patient
WO1996021454A1 (en) 1995-01-12 1996-07-18 Geltex Pharmaceuticals, Inc. Phosphate-binding polymers for oral administration
US6423754B1 (en) * 1997-06-18 2002-07-23 Geltex Pharmaceuticals, Inc. Method for treating hypercholesterolemia with polyallylamine polymers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992345A (en) * 1973-08-31 1976-11-16 Hercules Incorporated Water-dispersible thermosettable cationic resins and paper sized therewith
EP0143328A2 (en) * 1983-10-25 1985-06-05 Nitto Boseki Co., Ltd. Small-flobular crosslinked monoallylamine polymer and process for producing the same
US4680360A (en) * 1983-11-14 1987-07-14 Nitto Boseki Co., Ltd Process for producing poly(allylamine) derivatives
US4698380A (en) * 1985-09-23 1987-10-06 Ethyl Corporation Fluid loss control in well cement slurries
WO1996039449A1 (en) * 1995-06-06 1996-12-12 Geltex Pharmaceuticals, Inc. Hydrophobic heteroatom-containing sequestrant for cholesterol depletion

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002048209A1 (en) * 2000-12-13 2002-06-20 Dsm Fine Chemicals Austria Nfg Gmbh & Co. Kg Alkylation of cross-linked polymers containing n- or amino- or ammonium groups
US7148319B2 (en) 2000-12-13 2006-12-12 Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg Alkylation of crosslinked polymers containing N or amino or ammonium groups
CZ297744B6 (en) * 2000-12-13 2007-03-21 Dsm Fine Chemicals Austria Nfg Gmbh & Co. Kg Alkylation of cross-linked polymers containing N- or amine or ammonium groups
US6710162B2 (en) 2001-02-16 2004-03-23 Genzyme Corporation Method of drying a material having a cohesive phase
US7271237B2 (en) 2001-02-16 2007-09-18 Genzyme Corporation Method of drying a material having a cohesive phase
US7592417B2 (en) 2001-02-16 2009-09-22 Genzyme Corporation Method of drying a material having a cohesive phase
US6600011B2 (en) 2001-10-09 2003-07-29 Genzyme Corporation Process for purification and drying of polymer hydrogels
WO2006097942A1 (en) * 2005-03-16 2006-09-21 Council Of Scientific And Industrial Research An improved process for the preparation of crosslinked polyallylamine polymer.
WO2010029579A3 (en) * 2008-09-15 2010-05-20 Shasun Chemicals And Drugs Ltd Non-aqueous solution process for the preparation of cross-linked polymers
US20110196107A1 (en) * 2008-09-15 2011-08-11 Shasun Chemicals And Drugs Ltd. Non-Aqueous Solution Process for the Preparation of Cross-Linked Polymers
US8710154B2 (en) * 2008-09-15 2014-04-29 Shasun Pharmaceuticals Limited Non-aqueous solution process for the preparation of cross-linked polymers
ITMI20090816A1 (en) * 2009-05-12 2010-11-13 Chimico Internaz Spa Lab PROCEDURE FOR THE PREPARATION OF SEVELAMER
WO2010131092A1 (en) * 2009-05-12 2010-11-18 Laboratorio Chimico Internazionale S.P.A. Process for the preparation of sevelamer
EA021074B1 (en) * 2009-05-12 2015-03-31 Лабораторио Кимико Интернационале С.П.А. Process for the preparation of sevelamer hydrochloride and sevelamer carbonate/bicarbonate
US9303105B2 (en) 2009-05-12 2016-04-05 Laboratorio Chimico Internazionale S.P.A. Process for the preparation of sevelamer
WO2011099038A2 (en) * 2010-02-15 2011-08-18 Sun Pharmaceutical Industries Limited Process for preparing crosslinked allylamine polymer
WO2011099038A3 (en) * 2010-02-15 2012-09-27 Sun Pharmaceutical Industries Limited Process for preparing crosslinked allylamine polymer
US11186685B2 (en) 2016-12-28 2021-11-30 Fujifilm Corporation Emulsion of nitrogen atom-containing polymer or salt thereof, production method therefor, and production method for particles
US11147833B2 (en) 2017-10-16 2021-10-19 Fujifilm Corporation Therapeutic agent for hyperphosphatemia

Also Published As

Publication number Publication date
ES2288852T3 (en) 2008-02-01
US20010041756A1 (en) 2001-11-15
DK1175451T3 (en) 2007-11-05
CY1109000T1 (en) 2014-07-02
DE60035414T2 (en) 2008-03-13
JP2002542345A (en) 2002-12-10
JP4634618B2 (en) 2011-02-16
EP1881013A1 (en) 2008-01-23
EP1175451A1 (en) 2002-01-30
CA2362410A1 (en) 2000-10-26
DE60035414D1 (en) 2007-08-16
MXPA01010454A (en) 2002-05-06
PT1175451E (en) 2007-09-24
EP1175451B1 (en) 2007-07-04
US6525113B2 (en) 2003-02-25
ATE366264T1 (en) 2007-07-15

Similar Documents

Publication Publication Date Title
US6525113B2 (en) Process for producing cross-linked polyallylamine hydrochloride
EP0143328B1 (en) Small-flobular crosslinked monoallylamine polymer and process for producing the same
CN102639627A (en) A polymer support
US8710154B2 (en) Non-aqueous solution process for the preparation of cross-linked polymers
CA1094550A (en) Ionic pullulan gels and production thereof
N'Guyen et al. Phase-transfer catalysis in the chemical modification of polymers: 1.
US4232125A (en) Aminoalkylation of aromatic polymers using aldehyde, diacylamine and strong acid catalyst
Frechet et al. Polymer-assisted asymmetric reactions. 4. Polymer-bound ephedrine, its use and limitations in supported lithium aluminum hydride reductions
US6300431B1 (en) Phase transfer process with catalyst recovery
JPH051283B2 (en)
WO2011099038A2 (en) Process for preparing crosslinked allylamine polymer
JP3911794B2 (en) Cation exchange resin
JP4547620B2 (en) Method for producing crosslinked allylamine polymers
US6204337B1 (en) Solid-phase synthesis of codeine from morphine
Mitra et al. Polymer-bound benzyltriethylammonium polyhalides: recyclable reagents for the selective iodination of amines and phenols
JP3911801B2 (en) Anion exchange resin
JPH01143646A (en) Halo aromatic modified aromatic ion exchange resin
KR0134558B1 (en) Method for preparing ion exchange resin with high density and pores
JPH05506043A (en) Chelating ion exchange resins and their use for extracting metals
JPS6241224A (en) Chloromethylation of polyphenylene ether
EP0331829A1 (en) Chelation resins and their preparation
JPH11116840A (en) Removal of organic solvent
GB2292943A (en) Metal ion ligating materials
JPS5998105A (en) Preparation of hydrophilic ionomer
JPS5811885B2 (en) Method for manufacturing a polymonovinyl aromatic compound matrix molded product having an acrylic (or methacrylic) amidomethyl group

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA JP MX

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
ENP Entry into the national phase

Ref document number: 2362410

Country of ref document: CA

Ref country code: CA

Ref document number: 2362410

Kind code of ref document: A

Format of ref document f/p: F

ENP Entry into the national phase

Ref country code: JP

Ref document number: 2000 612344

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 2000923393

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: PA/a/2001/010454

Country of ref document: MX

WWP Wipo information: published in national office

Ref document number: 2000923393

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 2000923393

Country of ref document: EP