WO2008035109A1 - Rifaximin - Google Patents
Rifaximin Download PDFInfo
- Publication number
- WO2008035109A1 WO2008035109A1 PCT/GB2007/003629 GB2007003629W WO2008035109A1 WO 2008035109 A1 WO2008035109 A1 WO 2008035109A1 GB 2007003629 W GB2007003629 W GB 2007003629W WO 2008035109 A1 WO2008035109 A1 WO 2008035109A1
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- WO
- WIPO (PCT)
- Prior art keywords
- rifaximin
- water
- amorphous
- solvent
- mixture
- Prior art date
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention relates to amorphous rifaximin, pharmaceutical compositions containing the same, processes for preparing amorphous rifaximin and to therapeutic uses and therapeutic methods of treatment employing amorphous rifaximin, or such pharmaceutical compositions, medicaments or products.
- Rifaximin is a semi-synthetic, rifamycin-based non-systematic antibiotic. It is chemically termed as (2S,16Z,lSE,20S,21S,22R,23R,24R,25S,26 S,21S, 28E)-5,6,21,23,25-pentahydroxy-27- methoxy-2,4, 11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca- [1,11 ,13]trienimino)benzofuro[4,5-e]pyrido[l ,2-a]-benzimida-zole-l , 15(2H)-dione,25-acetate
- Rifaximin is used for treatment of travelers' diarrhea caused by noninvasive strains of Escherichia coli.
- Rifaximin was first disclosed in US4341785 which also discloses a process for its preparation and a method for crystallization of rifaximin using suitable solvents or mixture of solvents. However, this patent does not mention the polymorphism of rifaximin.
- Canadian patent CAl 215976 discloses a process for the synthesis of imidazo rifamycins which comprises reacting rifamycin S with 2-amino-4-methyl pyridine.
- US4557866 discloses a process for preparation of rifaximin, but does not mention the polymorphs of rifaximin.
- US7045620 discloses crystalline polymorphic forms of rifaximin which are termed as rifaximin ⁇ , rifaximin ⁇ and rifaximin ⁇ . These polymorphic forms are characterized using X-ray powder diffraction. Further this patent mentions that ⁇ form is poorly crystalline with a high content of amorphous component. This patent also discloses processes for preparation of these polymorphs
- rifaximin ⁇ which is characterized by water content lower than 4.5% & powder X-ray diffractogram having significant peaks are at values of diffraction angles 2 ⁇ of 6.6°; 7.4°; 7.9°, 8.8°, 10.5°, 11.1°, 11.8°, 12.9°, 17.6°, 18.5°, 19.7°, 21.0°, 21.4°, 22.1°; rifaximin ⁇ which is characterized by water content higher than 4.5% & powder X-ray diffractogram having significant peaks are at values of diffraction angles 20 of 5.4°; 6.4°; 7.0°, 7.8°, 9.0°,
- US2005/0272754 also discloses polymorphs of rifaximin namely rifaximin ⁇ form, rifaximin ⁇ 30 form & rifaximin ⁇ form characterized by powder X-ray diffractogram, intrinsic dissolution rates and processes of preparation of polymorphic forms of rifaximin.
- rifaximin ⁇ form namely rifaximin ⁇ form, rifaximin ⁇ 30 form & rifaximin ⁇ form characterized by powder X-ray diffractogram, intrinsic dissolution rates and processes of preparation of polymorphic forms of rifaximin.
- none of the above patents disclose a wholly amorphous form of rifaximin.
- amorphous form of a drug may exhibit different dissolution characteristics and in some case different bioavailability patterns compared to crystalline forms.
- amorphous and crystalline forms of a drug may have different handling properties, dissolution rates, solubility, and stability.
- Amorphous materials do not exhibit the three-dimensional long-range orders found in crystalline materials, but are structurally more similar to liquids where the arrangement of molecules is random.
- Amorphous solids do not give a definitive x-ray diffraction pattern (XRD). hi addition, amorphous solids do not give rise to a specific melting point and tend to liquefy at some point beyond the glass transition temperature. Because amorphous solids do not have lattice energy, they usually dissolve in a solvent more rapidly and consequently may provide enhanced bioavailability characteristics such as a higher rate and extent of absorption of the compound from the gastrointestinal tract. Also, amorphous forms of a drug may offer significant advantages over crystalline forms of the same drug in the manufacturing process of solid dosage form such as compressibility.
- Objectives of the invention Therefore, it is an object of the invention to provide amorphous form of rifaximin and a process for preparation thereof. It is also an object of the invention to provide processes for the inter-conversion of amorphous rifaximin to crystalline rifaximin and the inter-conversion of the crystalline forms.
- Another object of the present invention is to provide pharmaceutical compositions comprising an amorphous form of rifaximin.
- Yet another object of the present invention is to provide therapeutic uses and therapeutic methods of treatment employing compositions comprising amorphous rifaximin.
- the invention provides amorphous form of rifaximin. This may be characterized by its powder X-ray diffraction pattern, as shown in Figure 1.
- the amorphous rifaximin may be characterised by its FT-IR spectrum, as shown in Figure 2.
- the invention provides a process for preparation of amorphous form of rifaximin.
- the invention provides processes for inter-conversion of amorphous rifaximin to crystalline rifaximin and inter-conversions of crystalline forms.
- the invention comprises pharmaceutical compositions comprising amorphous form of rifaximin along with pharmaceutically acceptable carrier.
- the present invention provides therapeutic uses and therapeutic methods of treatment employing the compositions comprising amorphous rifaximin.
- the present invention provides amorphous rifaximin in bulk form, unlike the prior art which discloses a mixture of amorphous and crystalline rifaximin, and which provides no disclosure as to how to prepare bulk amorphous rifaximin.
- the amorphous rifaximin is substantially pure with polymorphic purity of 99% or more. Furthermore, it is substantially free of any peaks of crystalline rifaximin.
- room temperature used in present application refers to a temperature range between 25 - 30°C.
- stripping in this application refers to removal of traces of the first solvent from residue by adding second solvent and distilling it to residue.
- the present invention provides amorphous form of rifaximin.
- Amorphous form of rifaximin of the present invention is characterized by its powder X-ray diffraction pattern.
- the XRPD of the amorphous rifaximin was measured on a Rigaku DMAX 2200 Ultima "1" PC series X-ray powder diffractometer using a Cu K 11 radiation source, and is characterized by its XRPD pattern as shown in Figure I.
- the amorphous rifaximin can be characterised by its FT-IR pattern, as shown in Figure 2.
- Amorphous rifaximin according to the present invention is conveniently prepared by a process, which comprises reaction of Rifamycin S with 2-amino-4- picoline in presence of a suitable solvent like dichloromethane, ethyl acetate, dichloroethylene, chloroform, in an inert atmosphere. All these solvents can be used alone or in mixture among them or with water in various ratios.
- iodine dissolved in suitable solvent like dichloromethane, ethyl acetate, dichloroethylene, chloroform
- suitable reducing agent dissolved in water is preferably added to the above reaction mass and stirred at room temperature and then cooled to 10 - 15°C.
- the reducing agent used preferably comprises at least one of ascorbic acid, isoascorbic acid, sulphur dioxide, dihydroxyacetone.
- pH of the reaction mass is adjusted between 1.5-2.5, preferably to 2.0 - 2.2 under stirring.
- the reaction mass is preferably further stirred for 10-15 minutes and organic layer is separated.
- the separated organic layer is preferably washed with water, followed by washing with 10% sodium thiosulphate or 10% sodium metabisulphite and finally washed with water till pH of the organic layer is neutral.
- This separated organic layer is preferably further charcoalised, filtered, dried over sodium sulphate and concentrated under vacuum below 5O 0 C to residue.
- This residue contains rifaximin and can be further treated to obtain crystalline rifaximin (as in the prior art) or amorphous rifaximin (in accordance with the invention).
- the residue In the prior art, to manufacture the form known as the ⁇ form, the residue would be treated with a water miscible solvent, followed by drying in air at 80-110 0 C. To manufacture the ⁇ form in accordance with the prior art, the residue is treated with an organic acid and water, followed by drying in air at 100-110 0 C. I think is is best to maintain the temperatures, if they are the working temperatures, as we cannot add the information after filing.
- amorphous rifaximin is prepared by subjecting a residue containing rifaximin to a stripping step, followed by mixing with a mixture of water immiscible solvents, followed by drying at a temperature below 40°C - the amorphous rifaximin may be recovered after the drying step.
- the drying can be carried out at the temperature somewhat below 4O 0 C, e.g., at room temperature (for example 25°C).
- the residue obtained is preferably stripped out to dryness with suitable water immiscible organic solvent and the material obtained is isolated by stirring with the same solvent used for stripping or a mixture of solvents, preferably at room temperature. Further, the solid is filtered, washed with same solvents and dried below 40°C to get amorphous rifaximin.
- the suitable solvent used for stripping of the product is a water immiscible organic solvent selected from n-heptane, n-hexane, di-isopropyl ether, dichloromethane, dichloroethylene, chloroform and ethyl acetate.
- Amorphous rifaxiniin according to the present invention can be characterized by various parameters like solubility, intrinsic dissolution, bulk density, tapped density.
- Rifaximin is known to exist in 3 polymorphic Forms namely ⁇ Form, ⁇ Form & ⁇ Form of which the ⁇ Form is thermodynamically the most stable. Hence, the amorphous form of rifaximin was studied in comparison with ⁇ Form.
- Dissolution medium 1000 ml of 0. IM Sodium dihydrogen phosphate monohydrate + 4.5g of sodium lauryl sulphate. Temperature : 37 ⁇ 0.5°C Rotation speed : 100 rpm
- Amorphous rifaxiniin exhibits bulk density in the range of 0.3 - 0.4 g/ml and tapped density is in the range of 0.4 - 0.5 g/ml while the ⁇ Form rifaximin exhibits bulk density in the range of 0.2 - 0.3 g/ml & tapped density is in the range of 0.3 - 0.4 g/ml.
- These higher densities of amorphous 5 rifaximin are advantageous in formulation specifically in tablet formulation, for example, it gives better compressibility.
- Another aspect of the present invention is to provide conversion of amorphous rifaximin to crystalline ⁇ form rifaximin which comprises dissolving amorphous rifaximin in an organic
- the organic solvent used for dissolution and washing is organic acid.
- the organic acid preferably can be acetic acid or formic acid.
- Another embodiment of the present invention is to provide process for the conversion of amorphous rifaximin to crystalline ⁇ form rifaximin which comprises dissolving amorphous rifaximin hi an organic solvent, heating preferably to 40 - 60°C and stirring the reaction mixture to get clear solution.
- water may be added gradually at 40 - 60°C and stirred.
- the reaction mass may be cooled gradually to room temperature and stirred.
- the 5 resulting solid may be filtered and washed with mixture of suitable organic solvent and water.
- the solid may be further washed with mixture of organic solvent and water and then with water.
- the washed solid is dried at 80- 110°C to yield rifaximin ⁇ form.
- the organic solvent used for dissolution and washing comprises at least one of water miscible solvents preferably acetone, acetonitrile, C 1-4 alcohols.
- Another embodiment of the present invention is to provide process for inter-conversion of ⁇ form of rifaximin which comprises dissolving crystalline rifaximin in suitable solvent, heating preferably to 40 - 6O 0 C and stirred. Water is added, preferably dropwise, preferably at 40 - 60°C to the above mixture under stirring. The resulting mixture may be cooled gradually to room temperature and stirred. The solid obtained may be filtered, washed with mixture of solvents. Further the above solid may be washed with water, dried at 80 - 110°C to yield ⁇ form of rifaximin.
- Suitable solvent used for dissolving and washing the product is selected from water miscible solvents selected from group comprising of acetone, acetonitrile, lower alcohols or mixtures thereof.
- Yet another embodiment of the present invention is to provide conversion of crystalline form of rifaximin to amorphous rifaximin which comprises dissolving crystalline rifaximin in suitable solvent at room temperature and filtered.
- the filtrate may be washed with suitable solvent mentioned above and the solution may be concentrated, preferably under vacuum, preferably at
- the suitable solvent used for dissolving and stripping the product is selected from dichloromethane, dichloroethylene, chloroform, n-heptane, n-hexane and diisopropyl ether.
- Another aspect of present invention provides pharmaceutical composition comprising amorphous form of rifaximin in combination with a pharmaceutically acceptable carrier.
- the pharmaceutical composition of the present invention may contain one or more pharmaceutically acceptable ingredients.
- composition of the present invention can be formulated into variety of dosage forms, such as tablets, capsules, pills, caplets, lozenges, dispersible granules, dry powder syrup, ready to use suspension; parenteral dosage forms available in the art; various inhalation formulations; transdermal formulations, and the like. These formulations can be prepared using processes known in the art.
- Figure I is an X-ray powder diffractogram (XRD) of amorphous rifaxirnin made in accordance with example 1 as described below;
- Figure 2 is an FT-IR spectrum of amorphous rifaximin, made in accordance with example 1 described below;
- Figure 3 is a graphical representation of intrinsic dissolution of amorphous rifaximin compared with the ⁇ Form of rifaximin
- Amorphous rifaximin (100 g) was dissolved in acetic acid (200 ml) at 50 0 C, stirred for 30 - 45 minutes and demineralized water (200 ml) was added dropwise at 50 0 C in 30 - 45 minutes. Stirring was continued at 50 0 C for 30 - 45 minutes, cooled gradually to room temperature and stirred for 2 hours.
- the solid obtained was filtered and washed at first with acetic acid-water 1 : 1 mixture then with 10 % acetic acid-water mixture and finally washed with water.
- the solid obtained was dried at 100 - 110 0 C for 12 - 15 hours to get 62 - 65 g of rifaximin- ⁇ -form.
- Example 3 Amorphous rifaximin (100 g) was dissolved in formic acid (200 ml) at 50 0 C, stirred for 30 - 45 minutes and demineralized water (200 ml) was added dropwise at 50 0 C in 30 - 45 minutes. Stirring was continued at 50 0 C for 30 - 45 minutes, cooled gradually to room temperature and stirred for 2 hours. The solid obtained was filtered and washed at first with formic acid-water 1: 1 mixture then with 10 % formic acid-water mixture and finally washed with water. The solid obtained was dissolved in Isopropyl alcohol (310 ml) at 5O 0 C and stirred at 5O 0 C for 30 minutes.
- Demineralized water (310 ml) was added dropwise at 50 0 C in 30 - 45 minutes and stirring was continued at the same temperature for 30 - 45 minutes. The mixture was cooled gradually to room temperature and stirred for 2 hours. The solid obtained was filtered, washed with Isopropyl alcohol -water 1:1 mixture and then with demineralized water, dried at 80 - 90 0 C for 10 - 15 hours to get 40 - 45 g of rifaximin- ⁇ - form.
- Example 4 rifaximin ⁇ form (62 g) was dissolved in acetonitrile (310 ml) at 50°C and stirred at 5O 0 C for 30 minutes.
- Demineralized water (310 ml) was added dropwise at 50°C in 30 - 45 minutes and stirring was continued at the same temperature for 30 - 45 minutes. The mixture was cooled gradually to room temperature and stirred for 2 hours. The solid obtained was filtered, washed with acetonitrile-water 1:1 mixture and then with demineralized water, dried at 80 - 90°C for 10 - 15 hours to get 40 - 45 g of rifaximin- ⁇ - form.
- Crystalline rifaximin (40 g) was dissolved in dichloromethane (10 - 15 volumes) at room temperature, filtered through hyflo and washed with dichloromethane (2 volumes). The solution was concentrated under vacuum at 50°C. The solid was stripped out with n-heptane and stirred in n- heptane (50 ml) at room temperature for 30 minutes. Finally the solid was filtered, washed with n-heptane and dried under vacuum below 40 0 C to get 35 - 38 g of amorphous rifaximin.
- Tablet composition containing amorphous rifaximin Tablet composition containing amorphous rifaximin.
- a solid oral pharmaceutical formulation according to the present invention can be manufactured by granulation process known in the art.
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Abstract
Description
Claims
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2007298733A AU2007298733B2 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
EP07804377A EP2069363B1 (en) | 2006-09-22 | 2007-09-24 | Rifaximin in an amorphous form |
JP2009528789A JP2010504314A (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
CA2663776A CA2663776C (en) | 2006-09-22 | 2007-09-24 | Rifaximin in an amorphous form |
US12/441,368 US8633234B2 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
KR1020147026177A KR101667534B1 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
KR1020097008106A KR101480732B1 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
NZ575550A NZ575550A (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
US13/350,623 US20120116071A1 (en) | 2006-09-22 | 2012-01-13 | Rifaximin |
US14/152,713 US20140128419A1 (en) | 2006-09-22 | 2014-01-10 | Rifaximin |
US14/733,786 US9403844B2 (en) | 2006-09-22 | 2015-06-08 | Rifaximin |
US15/223,383 US9877953B2 (en) | 2006-09-22 | 2016-07-29 | Rifaximin |
US15/873,342 US10702505B2 (en) | 2006-09-22 | 2018-01-17 | Rifaximin |
US16/805,056 US20200368212A1 (en) | 2006-09-22 | 2020-02-28 | Rifaximin |
US17/746,038 US20230116935A1 (en) | 2006-09-22 | 2022-05-17 | Rifaximin |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN1520MU2006 | 2006-09-22 | ||
IN1520/MUM/2006 | 2006-09-22 |
Related Child Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/441,368 A-371-Of-International US8633234B2 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
US44136809A Substitution | 2006-09-22 | 2009-08-03 | |
US13/350,623 Continuation US20120116071A1 (en) | 2006-09-22 | 2012-01-13 | Rifaximin |
US14/152,713 Continuation US20140128419A1 (en) | 2006-09-22 | 2014-01-10 | Rifaximin |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008035109A1 true WO2008035109A1 (en) | 2008-03-27 |
Family
ID=38815026
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2007/003629 WO2008035109A1 (en) | 2006-09-22 | 2007-09-24 | Rifaximin |
Country Status (8)
Country | Link |
---|---|
US (8) | US8633234B2 (en) |
EP (1) | EP2069363B1 (en) |
JP (7) | JP2010504314A (en) |
KR (2) | KR101480732B1 (en) |
AU (1) | AU2007298733B2 (en) |
CA (1) | CA2663776C (en) |
NZ (1) | NZ575550A (en) |
WO (1) | WO2008035109A1 (en) |
Cited By (26)
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WO2008155728A1 (en) * | 2007-06-20 | 2008-12-24 | Solmag S.P.A. | Process for preparing amorphous rifaximin and the amorphous rifaximin thus obtained |
US7709634B2 (en) | 2007-09-20 | 2010-05-04 | Apotex Pharmachem Inc. | Amorphous form of rifaximin and processes for its preparation |
WO2010067072A1 (en) | 2008-12-10 | 2010-06-17 | Cipla Limited | Rifaximin complexes |
WO2011080691A1 (en) * | 2009-12-28 | 2011-07-07 | Silvio Massimo Lavagna | Method for the production of amorphous rifaximin |
ITRM20100157A1 (en) * | 2010-04-02 | 2011-10-03 | Silvio Massimo Lavagna | METHOD FOR THE PREPARATION OF RIFAXIMINA IN THE AMORPHOUS STATE. |
US8067429B2 (en) | 2008-02-25 | 2011-11-29 | Salix Pharmaceuticals, Ltd. | Forms of rifaximin and uses thereof |
WO2011107970A3 (en) * | 2010-03-05 | 2012-01-05 | Alfa Wassermann S.P.A. | Rifaximin powder, process for preparing the same and controlled release compositions containing said rifaximin useful for obtaining a long-lasting effect. |
WO2012060675A1 (en) * | 2010-11-05 | 2012-05-10 | Interquim, S.A. De C.V. | Process for the preparation of amorphous rifaximin |
WO2011110930A3 (en) * | 2010-03-10 | 2012-05-18 | Lupin Limited | Rifaximin ready-to-use suspension |
US8227482B1 (en) | 2011-02-11 | 2012-07-24 | Salix Pharmaceuticals, Ltd. | Forms of rifaximin and uses thereof |
WO2012150561A1 (en) | 2011-05-02 | 2012-11-08 | Ranbaxy Laboratories Limited | Rifaximin dimethylformamide solvate |
WO2012155981A1 (en) | 2011-05-19 | 2012-11-22 | Friulchem Spa | New process for the synthesis of rifaximin and a new pseudo-crystalline form of rifaximin obtained thereby |
ITMI20110983A1 (en) * | 2011-05-30 | 2012-12-01 | A M S A Anonima Materie Sint & Affini S P A | RIFAXIMINA AMORPHOUS AND PROCESS FOR ITS PREPARATION |
WO2013027227A1 (en) * | 2011-07-20 | 2013-02-28 | Ind-Swift Laboratories Limited | Novel polymorphic form i of rifaximin |
US8518949B2 (en) | 2005-03-03 | 2013-08-27 | Alfa Wassermann S.P.A. | Polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations |
US8569326B2 (en) | 2008-02-25 | 2013-10-29 | Salix Pharmaceuticals, Ltd. | Forms of rifaximin and uses thereof |
US8633234B2 (en) | 2006-09-22 | 2014-01-21 | Cipla Limited | Rifaximin |
WO2014167533A1 (en) | 2013-04-12 | 2014-10-16 | Alfa Wassermann S.P.A. | Nsaid administration and related compositions, methods and systems. |
EP2927235A1 (en) | 2014-03-31 | 2015-10-07 | Euticals S.P.A. | Polymorphic mixture of rifaximin and its use for the preparation of solid formulations |
WO2015173697A1 (en) | 2014-05-12 | 2015-11-19 | Alfa Wassermann S.P.A. | New solvated crystal form of rifaximin, production, compositions and uses thereof |
US9452157B2 (en) | 2012-07-06 | 2016-09-27 | Alfa Wassermann S.P.A | Pharmaceutical compositions comprising rifaximin and amino acids, preparation methods and use thereof |
US10314828B2 (en) | 2008-10-02 | 2019-06-11 | Salix Pharmaceuticals, Ltd | Methods of treating hepatic encephalopathy |
US10335397B2 (en) | 2008-10-02 | 2019-07-02 | Salix Pharmaceuticals, Ltd | Methods of treating hepatic encephalopathy |
CN111423456A (en) * | 2020-04-03 | 2020-07-17 | 南京昊绿生物科技有限公司 | Synthesis process of rifaximin-D6 |
US20200276170A1 (en) * | 2014-06-30 | 2020-09-03 | Salix Pharmaceuticals, Inc. | Methods for retreating irritable bowel syndrome (ibs) |
WO2021229480A1 (en) * | 2020-05-15 | 2021-11-18 | Atra Pharmaceuticals Limited | Polymorph of rifaximin, process for the preparation thereof and pharmaceutical composition containing rifaximin |
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CA2663776C (en) | 2016-01-26 |
KR20090080048A (en) | 2009-07-23 |
NZ575550A (en) | 2011-12-22 |
US10702505B2 (en) | 2020-07-07 |
JP2010504314A (en) | 2010-02-12 |
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US9877953B2 (en) | 2018-01-30 |
AU2007298733B2 (en) | 2012-11-08 |
JP7346353B2 (en) | 2023-09-19 |
US20150266898A1 (en) | 2015-09-24 |
US20120116071A1 (en) | 2012-05-10 |
JP2022003052A (en) | 2022-01-11 |
US20230116935A1 (en) | 2023-04-20 |
EP2069363A1 (en) | 2009-06-17 |
US20160374999A1 (en) | 2016-12-29 |
AU2007298733A1 (en) | 2008-03-27 |
JP2020128380A (en) | 2020-08-27 |
CA2663776A1 (en) | 2008-03-27 |
JP2016065058A (en) | 2016-04-28 |
US20140128419A1 (en) | 2014-05-08 |
US9403844B2 (en) | 2016-08-02 |
JP2023078160A (en) | 2023-06-06 |
JP2018127470A (en) | 2018-08-16 |
US8633234B2 (en) | 2014-01-21 |
KR20140131543A (en) | 2014-11-13 |
US20090312357A1 (en) | 2009-12-17 |
KR101480732B1 (en) | 2015-01-21 |
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