WO2000071124A1 - Amorphous form of fexofenadine hydrochloride - Google Patents
Amorphous form of fexofenadine hydrochloride Download PDFInfo
- Publication number
- WO2000071124A1 WO2000071124A1 PCT/IB2000/000708 IB0000708W WO0071124A1 WO 2000071124 A1 WO2000071124 A1 WO 2000071124A1 IB 0000708 W IB0000708 W IB 0000708W WO 0071124 A1 WO0071124 A1 WO 0071124A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fexofenadine hydrochloride
- amorphous form
- solvent
- fexofenadine
- amorphous
- Prior art date
Links
- RRJFVPUCXDGFJB-UHFFFAOYSA-N Fexofenadine hydrochloride Chemical compound Cl.C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RRJFVPUCXDGFJB-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 229960000354 fexofenadine hydrochloride Drugs 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001694 spray drying Methods 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 229960003592 fexofenadine Drugs 0.000 claims description 6
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003138 primary alcohols Chemical class 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 claims 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000002424 x-ray crystallography Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229960000351 terfenadine Drugs 0.000 description 3
- JHBWYQRKOUBPCA-UHFFFAOYSA-N 1-(6-methoxy-1,3-benzothiazol-2-yl)-3-phenylurea Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)NC1=CC=CC=C1 JHBWYQRKOUBPCA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229950008364 frentizole Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 description 1
- KEJCWVGMRLCZQQ-YJBYXUATSA-N Cefuroxime axetil Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(=O)OC(C)OC(C)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 KEJCWVGMRLCZQQ-YJBYXUATSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229960002620 cefuroxime axetil Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- ZEUXAIYYDDCIRX-UHFFFAOYSA-N losartan carboxylic acid Chemical compound CCCCC1=NC(Cl)=C(C(O)=O)N1CC1=CC=C(C=2C(=CC=CC=2)C2=NNN=N2)C=C1 ZEUXAIYYDDCIRX-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 229960003660 sertraline hydrochloride Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- 229960001544 sulfathiazole Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
Definitions
- This invention relates to an amorphous form of fexofenadine hydro- chloride, to a process for the preparation thereof, and to a composition containing it.
- fexofenadine is 4-[4-[4-hdroxydiphenylmethyl)-1-piperidin- yl]-hydroxybutyl]- ⁇ , ⁇ -dimethylbenzene acetic acid also known as terfenadine carboxylic acid metabolite having the Formula I.
- Fexofenadine hydrochloride (Terfenadine carboxylic acid hydrochlor- ide) is an effective antihistamine which avoids adverse effects associated with the administration of terfenadine including abnormal heart rhythms in some patients with liver disease or who also take the antifungal drug ketoconazole or the antibiotic erythromycin.
- polymorphism we mean to include different physical forms, crystal forms, crystalline/liquid crystalline/non- crystalline (amorphous) forms. This has especially become very interesting after observing that many antibiotics, antibacterials tranquiiizers etc, exhibit polymorphism and some/one of the polymorphic forms of a given drug exhibit superior bio-availability and consequently show much higher activity compared to other polymorphs. It has also been disclosed that the amorphous forms in a number of drugs exhibit different dissolution characteristics and in some cases different bioavailability patterns compared to the crystalline form [Konne T., Chem. Pharm.
- EP 490648 and EP 022527 also deal with the subject of polymorphism in drugs.
- PCT patent application WO 95/31437 discloses fexofenadine hydrochloride in various new crystalline forms designated Form I, Form II and Form IV and methods for their preparation.
- the first object of the present invention is to provide fexofenadine hydrochloride in an amorphous form.
- the amorphous form of fexofenadine hydrochloride is prepared by an efficient process which uses conditions which are convenient to operate on a commercial scale and operationally safe.
- the second object of the present invention is to provide a process for the preparation of fexofenadine hydrochloride in an amorphous form which comprises dissolving crystalline fexofenadine hydrochloride in a suitable solvent or dissolving fexofenadine base in a suitable solvent and adding a suitable solvent containing hydrogen chloride and recovering amorphous form of fexofenadine hydrochloride from the solution thereof by spray drying or freeze drying technique.
- a pharmaceutical composition comprising fexofenadine hydrochloride in an amorphous form with one or more pharmaceutical carriers and/or excipients.
- fexofenadine hydrochloride is recovered from the solution in an amorphous form using a freeze drying technique.
- the freeze dryer (Model : Virtis Genesis SQ Freeze - Dryer), which is used, operates on the principle of lyophilization, i.e., a process of stabilizing initially wet materials (aqueous solution or suspensions) by freezing them, then subliming the ice while simultaneously desorbing some of the bound moisture (primary drying). Following disappearance of the ice, desorp- tion may be prolonged (secondary drying). This process is preferably conducted under vacuum.
- fexofenadine hydrochloride is recovered from the solution in an amorphous form using a spray drying technique.
- the Mini-Spray Dryer (Model : Buchi 190, Switzerland) which is used, operates on the principle of nozzle spraying in a parallel - flow, i.e., the sprayed product and the drying gas flow in the same direction.
- the drying gas can be air or inert gases such as nitrogen, argon and carbon dioxide. Nitrogen is preferred in this case.
- suitable solvent means lower alkanol or combination of lower alkanol, ester, ketone, chlorinated solvent and mixture (s) thereof.
- Lower alkanol includes those primary, secondary and tertiary alcohols having from one to six carbon atoms.
- Suitable lower alkanol solvents include methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, amyl alcohol and t-butanol.
- ketone or ester includes solvents having from one to ten carbon atoms such as acetone, methyl ethyl ketone, 2-butanone, 4- methylpentan-2-one, ethyl acetate or n-butylacetate.
- suitable chlorinated solvents include dichloromethane, chloroform or carbon tetrachloride. Mixture of these solvents are also contemplated.
- Amorphous fexofenadine hydrochloride prepared according to the process of the present invention may be characterized by its infra-red spectrum in KBr disc ( Figure 1 ) and by its X-ray powder diffraction pattern
- Fexofenadine hydrochloride crystalline (124g, 0.231 moles) was dissolved in methanol (300ml) at 25-30 s C. The clear solution so obtained was subjected to spray drying in a Mini-Spray Dryer (Buchi Model 190) and fexofenadine hydrochloride in an amorphous form was isolated (114g).
- X-ray powder diffraction pattern ( Figure 2) shows a plain halo thus demonstrating the amorphous nature of the product. Infrared spectrum in KBr ( Figure 1 ) is different than the one obtained for crystalline form of fexofenadine hydrochloride ( Figure 3).
- Example 1 The process of Example 1 was repeated with fexofenadine hydrochloride (10g, 0.0186moles) using ethylacetate (20ml) and methanol
- Example 1 The process of Example 1 was repeated with fexofenadine hydrochloride (10g, 0.0186 moles) using acetone (20ml) and methanol (20ml) instead of methanol to give amorphous fexofenadine hydrochloride (8.9g).
- IR (KBr) spectrum and x-ray crystallography examination confirmed the amorphous nature of the product.
- Fexofenadine (15gm, 0.0299 moles) was suspended in methanol (60 ml) and to it was added isopropanol containing equivalent molar hydrogen chloride to get a clear solution.
- the clear solution was subjected to spray drying in a mini spray dryer (Buchi Model 190) and fexofenadine hydrochloride in an amorphous form was isolated (14.9g).
- IR (KBr) and x-ray crystallography revealed that the product was amorphous.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU46040/00A AU4604000A (en) | 1999-05-25 | 2000-05-25 | Amorphous form of fexofenadine hydrochloride |
| EP00927651A EP1185266A4 (en) | 1999-05-25 | 2000-05-25 | AMORPHOUS FORM OF FEXOFENADINE CHLORYDRATE |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN776DE1999 IN191492B (enrdf_load_stackoverflow) | 1999-05-25 | 1999-05-25 | |
| IN776/DEL/99 | 1999-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000071124A1 true WO2000071124A1 (en) | 2000-11-30 |
Family
ID=11091185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2000/000708 WO2000071124A1 (en) | 1999-05-25 | 2000-05-25 | Amorphous form of fexofenadine hydrochloride |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP1185266A4 (enrdf_load_stackoverflow) |
| AU (1) | AU4604000A (enrdf_load_stackoverflow) |
| IN (1) | IN191492B (enrdf_load_stackoverflow) |
| WO (1) | WO2000071124A1 (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001094313A3 (en) * | 2000-06-06 | 2002-04-04 | Novartis Ag | Crystal modification of fexofenadine |
| WO2002066429A1 (de) | 2001-02-23 | 2002-08-29 | Cilag Ag | Verfahren zur herstellung von nicht hydratisiertem fexofenadin-hydrochlorid und eine so erhaetliche neue kristalline form |
| WO2002080857A3 (en) * | 2001-04-09 | 2003-12-18 | Teva Pharma | Polymorphs of fexofenadine hydrochloride |
| CN100390145C (zh) * | 2001-06-18 | 2008-05-28 | 雷迪实验室有限公司 | 4-[4-[4-(羟基二苯基甲基)-1-哌啶基]-1-羟基丁基]-α,α-二甲基苯乙酸和其盐酸盐的结晶形式 |
| US7589128B2 (en) | 2004-06-01 | 2009-09-15 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparation of amorphous form of a drug |
| EP2105134A1 (en) | 2008-03-24 | 2009-09-30 | Ranbaxy Laboratories Limited | Stable amorphous fexofenadine hydrochloride |
| US7671071B2 (en) | 2002-06-10 | 2010-03-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic Form XVI of fexofenadine hydrochloride |
| KR101014010B1 (ko) * | 2010-12-30 | 2011-02-14 | 주식회사 한국에너지관리 | 기체방울 수중 분산장치 |
| WO2011158262A1 (en) | 2010-06-15 | 2011-12-22 | Chemelectiva S.R.L. | Polymorphic form of fexofenadine hydrochloride, intermediates and process for its preparation |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254129A (en) * | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
| US4285957A (en) * | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof |
| WO1995031437A1 (en) * | 1994-05-18 | 1995-11-23 | Hoechst Marrion Roussel, Inc. | Processes for preparing anhydrous and hydrate forms of antihistaminic piperidine derivatives, polymorphs and pseudormophs thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU44680B (en) * | 1982-07-30 | 1990-12-31 | Glaxo Lab Ltd | Process for obtaining very pure amorphous form of cephuroxim axetile |
| CA1339136C (en) * | 1987-07-01 | 1997-07-29 | Sailesh Amilal Varia | Amorphous form of aztreonam |
| US5631375A (en) * | 1992-04-10 | 1997-05-20 | Merrell Pharmaceuticals, Inc. | Process for piperidine derivatives |
| CA2206592A1 (en) * | 1996-05-30 | 1997-11-30 | Shu-Zhong Wang | Method of producing amorphous paroxetine hydrochloride |
| US5925761A (en) * | 1997-02-04 | 1999-07-20 | Sepracor Inc. | Synthesis of terfenadine and derivatives |
-
1999
- 1999-05-25 IN IN776DE1999 patent/IN191492B/en unknown
-
2000
- 2000-05-25 WO PCT/IB2000/000708 patent/WO2000071124A1/en not_active Application Discontinuation
- 2000-05-25 EP EP00927651A patent/EP1185266A4/en not_active Withdrawn
- 2000-05-25 AU AU46040/00A patent/AU4604000A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254129A (en) * | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
| US4285957A (en) * | 1979-04-10 | 1981-08-25 | Richardson-Merrell Inc. | 1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof |
| WO1995031437A1 (en) * | 1994-05-18 | 1995-11-23 | Hoechst Marrion Roussel, Inc. | Processes for preparing anhydrous and hydrate forms of antihistaminic piperidine derivatives, polymorphs and pseudormophs thereof |
Non-Patent Citations (7)
| Title |
|---|
| DATABASE CAS ON STN (COLUMBUS, OHIO, USA); CORRIGAN ET AL.: "Physicochemical properties of spray dried drugs: phenobarbitone and hydroflumethiazide", XP002931700, Database accession no. ACCESSION NO. 98:166814 * |
| DATABASE CAS ON STN (COLUMBUS, OHIO, USA); NUERNBERG E.: "Colloidal distribution states in pharmaceutical technology. Manufacture and qualities of pharmaceutical preparations by spray drying", XP002931699, Database accession no. ACCESSION NO. 86:8603 * |
| DRUG DEV. IND. PHARM., vol. 9, no. 1-2, 1983, pages 1 - 20 * |
| LIEBERMAN HERBERT A., "Pharmaceutical dosage forms", New York, Marcel Dekker, Inc., 1989, volume 2, page 463, XP002932153. * |
| PROG. COLLOID POLYM. SCI., vol. 59, 1976, pages 55 - 59 * |
| See also references of EP1185266A4 * |
| SUZUKI E. ET AL.: "Studies on methods of particle size reduction of medicinal compounds. VIII.(1) Size reduction by freeze-drying and the influence of pharmaceutical adjuvants on the micromeritic properties of freeze-dried powders", CHEM. PHARM. BULL., vol. 27, no. 5, 1979, pages 1214 - 1222, XP002932152 * |
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| WO2001094313A3 (en) * | 2000-06-06 | 2002-04-04 | Novartis Ag | Crystal modification of fexofenadine |
| US7759364B2 (en) | 2001-02-23 | 2010-07-20 | Cilag Ag | Method for producing non-hydrated fexofenadine hydrochloride and a novel crystalline form obtained thereby |
| WO2002066429A1 (de) | 2001-02-23 | 2002-08-29 | Cilag Ag | Verfahren zur herstellung von nicht hydratisiertem fexofenadin-hydrochlorid und eine so erhaetliche neue kristalline form |
| CH695216A5 (de) * | 2001-02-23 | 2006-01-31 | Cilag Ag | Verfahren zur Herstellung eines nicht hydratisierten Salzes eines Piperidinderivats und eine so erhältliche neue kristalline Form eines solchen Salzes. |
| WO2002080857A3 (en) * | 2001-04-09 | 2003-12-18 | Teva Pharma | Polymorphs of fexofenadine hydrochloride |
| CN100390145C (zh) * | 2001-06-18 | 2008-05-28 | 雷迪实验室有限公司 | 4-[4-[4-(羟基二苯基甲基)-1-哌啶基]-1-羟基丁基]-α,α-二甲基苯乙酸和其盐酸盐的结晶形式 |
| EP2261209A1 (en) | 2001-06-18 | 2010-12-15 | Dr. Reddy's Laboratories Ltd. | Novel crystalline forms of 4-[4-[4- hydroxydiphenylmethyl)-1-piperidinyl]-1-hydroxybutyl]-alpha, alpha-dimethylbenene acetic acid and its hydrochloride |
| US7671071B2 (en) | 2002-06-10 | 2010-03-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic Form XVI of fexofenadine hydrochloride |
| US7589128B2 (en) | 2004-06-01 | 2009-09-15 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparation of amorphous form of a drug |
| EP2105134A1 (en) | 2008-03-24 | 2009-09-30 | Ranbaxy Laboratories Limited | Stable amorphous fexofenadine hydrochloride |
| WO2011158262A1 (en) | 2010-06-15 | 2011-12-22 | Chemelectiva S.R.L. | Polymorphic form of fexofenadine hydrochloride, intermediates and process for its preparation |
| KR101014010B1 (ko) * | 2010-12-30 | 2011-02-14 | 주식회사 한국에너지관리 | 기체방울 수중 분산장치 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1185266A4 (en) | 2002-07-17 |
| EP1185266A1 (en) | 2002-03-13 |
| IN191492B (enrdf_load_stackoverflow) | 2003-12-06 |
| AU4604000A (en) | 2000-12-12 |
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