HRP20110093T1 - Kristalna baza escitaloprama i orodisperzibilne tablete koje sadrže bazu escitaloprama - Google Patents
Kristalna baza escitaloprama i orodisperzibilne tablete koje sadrže bazu escitaloprama Download PDFInfo
- Publication number
- HRP20110093T1 HRP20110093T1 HR20110093T HRP20110093T HRP20110093T1 HR P20110093 T1 HRP20110093 T1 HR P20110093T1 HR 20110093 T HR20110093 T HR 20110093T HR P20110093 T HRP20110093 T HR P20110093T HR P20110093 T1 HRP20110093 T1 HR P20110093T1
- Authority
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- Prior art keywords
- escitalopram
- free base
- crystalline
- salt
- base
- Prior art date
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- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title claims abstract 32
- 229960004341 escitalopram Drugs 0.000 title claims abstract 28
- 239000012458 free base Substances 0.000 claims abstract 15
- 239000007787 solid Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 16
- 239000012535 impurity Substances 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000002585 base Substances 0.000 claims 5
- WIHMBLDNRMIGDW-BDQAORGHSA-N escitalopram hydrobromide Chemical compound Br.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WIHMBLDNRMIGDW-BDQAORGHSA-N 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 239000002244 precipitate Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- KTGRHKOEFSJQNS-BDQAORGHSA-N (1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;oxalic acid Chemical compound OC(=O)C(O)=O.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 KTGRHKOEFSJQNS-BDQAORGHSA-N 0.000 claims 2
- DIOGFDCEWUUSBQ-FQEVSTJZSA-N 3-[(1s)-5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]-n,n-dimethylpropan-1-amine oxide Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCC[N+](C)([O-])C)=CC=C(F)C=C1 DIOGFDCEWUUSBQ-FQEVSTJZSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 229960005086 escitalopram oxalate Drugs 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Slobodna baza escitaloprama u čvrstom obliku, naznačena time, što sadrži kristalni escitalopram. Patent sadrži još 21 patentni zahtjev.
Claims (22)
1. Slobodna baza escitaloprama u čvrstom obliku, naznačena time, što sadrži kristalni escitalopram.
2. Slobodna baza escitaloprama prema zahtjevu 1, naznačena time, što je bar 90% kristalna, posebno bar 95% kristalna i posebnije, bar 98% kristalna.
3. Slobodna baza escitaloprama prema zahtjevu 1, naznačena time, što je kristalna.
4. Farmaceutska smjesa, naznačena time, što sadrži slobodnu bazu escitaloprama prema zahtjevima 1 do 3.
5. Postupak za proizvodnju slobodne baze escitaloprama ili njene soli, naznačen time, što escitalopram hidrobromid precipitira u kristalnom obliku u otapalu i odvaja se od otapala, opcijski se rekristalizira jednom ili više puta i zatim transformira u slobodnu bazu escitaloprama ili njenu sol, s time da proizvedena sol escitaloprama nije hidrobromid.
6. Postupak prema zahtjevu 5 za proizvodnju slobodne baze escitaloprama ili njene soli, naznačen time, što escitalopram hidrobromid precipitira iz sirovog escitaloprama.
7. Postupak prema zahtjevu 5 ili 6 za proizvodnju slobodne baze escitaloprama ili njene soli, naznačen time, što se jedna ili više nečistoća formula (II) ili (III)
[image]
gdje je Z halogen, cijano ili -CONH2,
R1 i R2 su nezavisno vodik ili metil, s time da ako su R1 i R2 oba metil, onda Z ne može biti cijano,
i veze koje su u formuli (III) prikazane kao cik-cak linije ukazuju da konfiguracija oko dvogube veze može biti E- ili Z-;
uklanjaju ili umanjuju u escitalopramu ovim postupkom.
8. Postupak prema zahtjevu 7, naznačen time, što nečistoće imaju formulu (II), gdje
Z je bromo ili kloro i R1 i R2 su oba metil,
Z je -CONH2 i R1 i R2 su oba metil, ili
Z je cijano, R1 je vodonik i R2 je metil;
ili formulu (III) gde je konfiguracija oko dvogube veze Z.
9. Postupak prema bilo kojem od zahtjeva 6 do 8, naznačen time, što se sirovi escitalopram podvrgava inicijalnom prečišćavanju prije no što escitalopram hidrobromid precipitira u kristalnu formu.
10. Postupak prema bilo kojem od zahtjeva 5 do 9, naznačen time, što se escitalopram hidrobromid transformiara u slobodnu bazu escitaloprama ili escitalopram oksalat.
11. Kristalna baza escitaloprama, naznačena time, što sadrži manje od 0.20% nečistoća različitih od R-citaloprama, posebno manje od 0.10%.
12. Kristalna baza prema zahtjevu 11, naznačena time, što sadrži manje od 0.10% bilo koje posebne nečistoće različite od R-citaloprama.
13. Kristalna baza escitaloprama, naznačena time, što je pripremljena postupkom iz bilo kojeg od zahtjeva 5-10.
14. Baza iz zahtjeva 13, naznačena time, što sadrži manje od 0.20% nečistoća različitih od R-citaloprama, posebno manje od 0.10%.
15. Kristalna baza prema zahtjevu 14, naznačena time, što sadrži manje od 0.10% bilo koje posebne nečistoće različite od R-citaloprama.
16. Postupak za proizvodnju soli escitaloprama, naznačen time, što slobodna baza escitaloprama precipitira u čvrstu formu u otapalu i odvaja se od otapala, opcijski se rekristalizira jednom ili više puta i zatim transformira u sol escitaloprama.
17. Postupak prema zahtjevu 16 za proizvodnju soli escitaloprama, naznačen time, što slobodna baza escitaloprama precipitira iz sirovog escitaloprama.
18. Postupak prema zahtjevu 16 ili 17 za proizvodnju soli escitaloprama, naznačen time, što se nečistoća formule (II)
[image]
gdje je Z cijano, R1 je metil i R2 je vodik, postupkom uklanja ili smanjuje u escitalopramu.
19. Postupak prema zahtjevu 18, naznačen time, što je Z bromo.
20. Postupak prema bilo kojem od zahtjeva 17 do 19, naznačen time, što se sirovi escitalopram podvrgava inicijalnom prečišćavanju prije nego što escitalopram hidrobromid precipitira u kristalnu formu.
21. Postupak prema bilo kojem od zahtjeva 17 do 20, naznačen time, što se slobodna baza escitaloprama transformira u escitalopram oksalat.
22. Postupak smanjenja količine escitalopram N-oksida u slobodnoj bazi escitaloprama ili njenoj soli, naznačen time, što uključuje otapanje slobodne baze escitaloprama u dietil-eteru i uklanjanje escitalopram N-oksida kao čvrstog materijala.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200500912 | 2005-06-22 | ||
| PCT/DK2006/000366 WO2006136169A2 (en) | 2005-06-22 | 2006-06-22 | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
| EP06742481.2A EP1896439B2 (en) | 2005-06-22 | 2006-06-22 | Crystalline base of escitalopram and orodispersible tablets comprising escitalopram base |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20110093T1 true HRP20110093T1 (hr) | 2011-03-31 |
| HRP20110093T4 HRP20110093T4 (hr) | 2015-02-27 |
Family
ID=37546630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20110093TT HRP20110093T4 (hr) | 2005-06-22 | 2011-02-04 | Kristalna baza escitaloprama i orodisperzibilne tablete koje sadrže bazu escitaloprama |
Country Status (39)
| Country | Link |
|---|---|
| EP (3) | EP2385044A1 (hr) |
| JP (5) | JP4906852B2 (hr) |
| KR (5) | KR101340815B1 (hr) |
| CN (2) | CN101189220A (hr) |
| AR (2) | AR055062A1 (hr) |
| AT (3) | AT10983U1 (hr) |
| AU (2) | AU2006261452B2 (hr) |
| BG (1) | BG66086B1 (hr) |
| BR (1) | BRPI0612295A2 (hr) |
| CA (2) | CA2646780A1 (hr) |
| CY (1) | CY1112392T1 (hr) |
| CZ (3) | CZ301286B6 (hr) |
| DE (2) | DE112006001619T5 (hr) |
| DK (3) | DK1896439T4 (hr) |
| EA (2) | EA019239B1 (hr) |
| EE (1) | EE00773U1 (hr) |
| ES (2) | ES2356838T5 (hr) |
| FI (2) | FI20077133A (hr) |
| GB (2) | GB2442160B (hr) |
| HR (1) | HRP20110093T4 (hr) |
| HU (1) | HUP0800135A3 (hr) |
| IL (1) | IL187454A0 (hr) |
| IS (1) | IS8705A (hr) |
| LT (1) | LT5550B (hr) |
| LV (1) | LV13677B (hr) |
| MX (1) | MX2007015328A (hr) |
| MY (2) | MY143239A (hr) |
| NO (2) | NO20080359L (hr) |
| PL (2) | PL1896439T5 (hr) |
| PT (1) | PT1896439E (hr) |
| RS (1) | RS51575B2 (hr) |
| SG (1) | SG169358A1 (hr) |
| SI (1) | SI1896439T2 (hr) |
| SK (1) | SK500402007A3 (hr) |
| TR (2) | TR201000625T1 (hr) |
| TW (2) | TWI347942B (hr) |
| UA (1) | UA86536C2 (hr) |
| WO (1) | WO2006136169A2 (hr) |
| ZA (2) | ZA200711066B (hr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0123400D0 (en) | 2001-09-28 | 2001-11-21 | Novartis Ag | Organic compounds |
| WO2008059514A2 (en) * | 2006-07-31 | 2008-05-22 | Cadila Healthcare Limited | Process for preparing escitalopram |
| WO2008104880A2 (en) * | 2007-03-01 | 2008-09-04 | Aurobindo Pharma Limited | Stable solid dosage forms of an antidepressant |
| PL2595979T3 (pl) | 2010-07-23 | 2016-07-29 | H Lundbeck As | Sposób oczyszczania farmaceutycznie dopuszczalnych soli escitalopramu |
| CN103360353A (zh) * | 2013-08-07 | 2013-10-23 | 中国药科大学 | 草酸艾司西酞普兰杂质的制备方法 |
| JP2018016569A (ja) * | 2016-07-26 | 2018-02-01 | 株式会社トクヤマ | （１ｓ）−１−［３−（ジメチルアミノ）プロピル］−１−（４−フルオロフェニル）−１，３−ジヒドロイソベンゾフラン−５−カルボニトリル蓚酸塩の製造方法 |
| WO2018190294A1 (ja) * | 2017-04-10 | 2018-10-18 | 東和薬品株式会社 | エスシタロプラム医薬組成物 |
| CN110711198B (zh) * | 2018-07-12 | 2022-03-15 | 山东大学 | D-甘露糖在制备抗抑郁药物中的应用 |
| KR102331187B1 (ko) | 2019-04-09 | 2021-11-26 | 주식회사 라이트팜텍 | 에스시탈로프람을 함유하는 안정성이 우수한 경구용 액제 조성물 및 그의 제조방법 |
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| HU227491B1 (en) * | 2003-11-25 | 2011-07-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Tablet containing citalopram hydrogen bromide |
| EP1732514A1 (en) * | 2004-03-05 | 2006-12-20 | H. Lundbeck A/S | Crystalline composition containing escitalopram oxalate |
| WO2006106531A1 (en) * | 2005-04-04 | 2006-10-12 | Jubilant Organosys Ltd | Process for the preparation of escitalopram or its acid addition salts |
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