DK1755596T3 - Fremgangsmåde til fremstilling af atazanavirbisulfat og hidtil ukendte former - Google Patents
Fremgangsmåde til fremstilling af atazanavirbisulfat og hidtil ukendte former Download PDFInfo
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- DK1755596T3 DK1755596T3 DK05744537.1T DK05744537T DK1755596T3 DK 1755596 T3 DK1755596 T3 DK 1755596T3 DK 05744537 T DK05744537 T DK 05744537T DK 1755596 T3 DK1755596 T3 DK 1755596T3
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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- 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
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- 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
- A61P31/12—Antivirals
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- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
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Claims (27)
- FREMGANGSMÅDE TIL FREMSTILLING AF ATAZANAVIRBISULFAT OG HIDTIL UKENDTE FORMER1. Fremgangsmåde til fremstilling af atazanavirbisulfat i form af Form A-krystaller, hvilken fremgangsmåde omfatter omsætning af en opløsning af atazanavir fri base i et organisk opløsningsmiddel, der er acetone eller en blanding af acetone og N-methylpyrrolidon, med en første del af koncentreret svovlsyre i en mængde til at omsætte med mindre end ca. 15 vægt-% atazanavir fri base, tilsætning afkom af Form A-krystaller af atazanavirbisulfat til reaktionsblandingen, mens krystaller af atazanavirbisulfat dannes, tilsætning af supplerende koncentreret svovlsyre i flere trin ved en tiltagende rytme ifølge følgende ligninghvor Vtid = svovlsyrevolumen tilsat i det forløbne tidsrum Vtotai= totalt syrevolumen, der repræsenterer ladningen på 90 % tid = forløbet krystalliseringstid tidtotal = forløbet krystalliseringstid i alt eller tid i alt for syreladning for at bevirke dannelse af atazanavirbisulfatkrystaller og tørring af atazanavirbisulfatet for at danne Form A-krystaller.
- 2. Fremgangsmåde ifølge krav 1, hvor opløsningen af atazanavir fri base initialt omsættes med fra 5 til 15 vægt-% af den totale mængde anvendt svovlsyre.
- 3. Fremgangsmåde ifølge krav 1, hvor opløsningen af atazanavir fri base initialt omsættes med fra 8 til 12 vægt-% af den totale mængde anvendt svovlsyre.
- 4. Fremgangsmåde ifølge krav 1, hvor atazanavir fri base omsættes med den første svovlsyredel ved en temperatur inden for intervallet fra 35 til 55 °C.
- 5. Fremgangsmåde ifølge krav 1, hvor opløsningen af atazanavir fri base opvarmes til en temperatur inden for intervallet fra 35 til 55 °C, inden den omsættes med svovlsyre.
- 6. Fremgangsmåde ifølge krav 1, hvor reaktionsblandingen af atazanavir fri base og svovlsyre podes med fra 0,1 til 80 vægt-% Form A-krystaller baseret på vægten af atazanavir fri base.
- 7. Fremgangsmåde ifølge krav 1, hvor den podede reaktionsblanding opvarmes til en temperatur inden for intervallet fra 35 til 55 °C.
- 8. Fremgangsmåde ifølge krav 1, hvor det organiske opløsningsmiddel til atazanavir fri base er en blanding af acetone og N-methylpyrro lidon.
- 9. Fremgangsmåde til fremstilling af atazanavirbisulfat Mønster C-materialet, hvilken fremgangsmåde omfatter udsættelse af Form A-krystaller af atazanavirbisulfat for en høj relativ fugtighed på mindst ca. 95 % RH i mindst 24 timer og derefter tørring.
- 10. Fremgangsmåde til fremstilling af atazanavirbisulfat Mønster C-materiale, hvilken fremgangsmåde omfatter (a) omsætning af en opløsning af atazanavir fri base i et organisk opløsningsmiddel, der er acetone eller en blanding af acetone og N-methylpyrrolidon, med en første del af koncentreret svovlsyre i en mængde til at omsætte med mindre end ca. 15 vægt-% atazanavir fri base, tilsætning afkom af Form A-krystaller af atazanavirbisulfat til reaktionsblandingen, mens krystaller af atazanavirbisulfat dannes, tilsætning af supplerende koncentreret svovlsyre i flere trin ved en tiltagende rytme ifølgehvor Vtid = svovlsyrevolumen tilsat i det forløbne tidsrum Vt0tai = totalt syrevolumen, der repræsenterer ladningen på 90 % tid = forløbet krystalliseringstid tidtotai = forløbet krystalliseringstid i alt eller tid i alt for syreladning for at bevirke dannelse af atazanavirbisulfatkrystaller, og tørring af atazanavirbisulfat for at danne Form A-krystaller; (b) suspension af krystallerne af Form A atazanavirbisulfat fra trin (a) i vand og tørring af suspensionen for at danne Mønster C-materiale; eller (c) udsættelse af krystaller af Form A atazanavirbisulfat fra trin (a) for en høj relativ fugtighed på mere end 95 % RH i mindst 24 timer for at danne Mønster C-materiale eller (d) blanding af Form A-krystaller fra trin (a) med en eller flere formuleringsexcipienser og vådgranulering af den resulterende blanding for direkte at danne Mønster C-materiale i blanding med excipienseme.
- 11. Fremgangsmåde ifølge krav 1 til fremstilling af atazanavirbisulfati form af Form A-krystaller, hvilken fremgangsmåde omfatter fremstilling af et triaminsalt med strukturenog uden isolering af triaminsaltet, omsætning af triaminsaltet med en aktiv ester af en syre med strukturenog en base i tilstedeværelse af et organisk opløsningsmiddel for at danne en opløsning af atazanavir fri base med strukturenog omdannelse af den frie base til det tilsvarende bisulfatsalt ved behandling af en opløsning af fri base i methylenchlorid med N-methylpyrrolidon og acetone, opvarmning af ovenstående blanding for at ijeme methylenchlorid og behandling af ovenstående blanding med svovlsyre for at danne bisulfatsaltet af den fri base, hvor svovlsyren tilsættes ved en tiltagende rytme ifølge følgende ligninghvor Vtid = svovlsyrevolumen tilsat i det forløbne tidsrum Vtotai= totalt syrevolumen, der repræsenterer ladningen på 90 % tid = forløbet krystalliseringstid tidtotai = forløbet krystalliseringstid i alt eller tid i alt for syreladning
- 12. Fremgangsmåde ifølge krav 11, hvor triaminsaltet er hydrochloridsaltet
- 13. Fremgangsmåde ifølge krav 11, hvor syrens aktive ester har strukturen
- 14. Fremgangsmåde ifølge krav 11, hvor basen er et alkalimetalhydroxid, et alkalisk jordmetalhydroxid, et alkalimetalcarbonat, et alkalisk jordmetalearbonat, et alkalimetalphosphat, et alkalisk jordmetalphosphat eller en organisk base.
- 15. Fremgangsmåde ifølge krav 14, hvor basen er NaOH, KOH, Mg(OH)2, K2HP04, MgC03, Na2C03, K2C03, triethylamin, diisopropylethylamin eller N-methylmorpholin og det organiske opløsningsmiddel er methylenchlorid, ethylacetat, dichlorethan, tetrahydrofuran, acetonitril eller N,N-dimethylformamid.
- 16. Fremgangsmåde ifølge krav 11, hvor triaminsaltet og den aktive ester omsættes ved en temperatur inden for intervallet fra 30 til 40 °C.
- 17. Fremgangsmåde ifølge krav 16, hvor triaminsaltet og den aktive ester omsættes i tilstedeværelse af K2HP04 som basen og methylenchlorid som opløsningsmidlet.
- 18. Fremgangsmåde ifølge krav 11, hvilken fremgangsmåde indbefatter trinnet med podning af blandingen af fri base, acetone og N-methylpyrrolidon med krystaller af atazanavirbisulfat.
- 19. Fremgangsmåde til fremstilling af atazanavirbisultat,hvilken fremgangsmåde omfatter fremstilling af et triaminhydrogenchloridsalt med strukturenomsætning af triaminhydrogenchloridsaltet med en aktiv ester med strukturenog K2HPO4 i tilstedeværelse af methylenchlorid for at danne en opløsning af den frie base med struktureni methylenchlorid og omdannelse af den frie base til det tilsvarende bisulfatsalt via en kubisk krystalliseringsteknik, hvor svovlsyren tilsættes ved en tiltagende rytme ifølge følgende ligninghvor Vtid = svovlsyrevolumen tilsat i det forløbne tidsrum Vtotai = totalt syrevolumen, der repræsenterer ladningen på 90 % tid = forløbet krystalliseringstid tidtotal = forløbet krystalliseringstid i alt eller tid i alt for syreladning
- 20. Form E3 af atazanavirbisulfat.
- 21. Forbindelse ifølge krav 20 fremstillet som et triethanolatsolvat af atazanavirbisulfat.
- 22. Forbindelse ifølge krav 20 kendetegnet ved et røntgenpulverdiffraktionsmønster i alt væsentligt som det, der vises i figur 9.
- 23. Forbindelse ifølge krav 20 med krystalstrukturen i alt væsentligt, som den der vises i figur 10.
- 24. Forbindelse ifølge krav 20, der er kendetegnet ved fraktionsatomkoordinater i alt væsentligt som de, der er opført i tabel 6.
- 25. Forbindelse ifølge krav 20, der er kendetegnet ved krystallografiske data, der i alt væsentligt svarer til følgende: Celledimensioner: a =10,749(5) Å b = 13,450(4) A c = 9,250(2) Å a = 98,33(2)° β = 95,92(3)° γ= 102,82(3)° Afstandsgruppe PI Molekyler/asymmetrisk enhed 1 hvor den krystallinske form er ved ca. -23 °C.
- 26. Forbindelse ifølge krav 20, der er kendetegnet ved differentiel scanningskalorimetriske termogramdata, der i alt væsentligt stemmer overens med de data, der vises i figur 11.
- 27. Forbindelse ifølge krav 20, der er kendetegnet ved en termogravimetrisk analysekurve, der i alt væsentligt, stemmer overens med den kurve, der vises i figur 11.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US56804304P | 2004-05-04 | 2004-05-04 | |
US60753304P | 2004-09-07 | 2004-09-07 | |
US11/119,558 US7829720B2 (en) | 2004-05-04 | 2005-05-02 | Process for preparing atazanavir bisulfate and novel forms |
PCT/US2005/015333 WO2005108349A2 (en) | 2004-05-04 | 2005-05-03 | Process for preparing atazanavir bisulfate and novel forms |
Publications (2)
Publication Number | Publication Date |
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DK1755596T3 true DK1755596T3 (da) | 2015-11-16 |
DK1755596T5 DK1755596T5 (da) | 2016-05-23 |
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Application Number | Title | Priority Date | Filing Date |
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DK05744537.1T DK1755596T5 (da) | 2004-05-04 | 2005-05-03 | Fremgangsmåde til fremstilling af atazanavirbisulfat og hidtil ukendte former |
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Country | Link |
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US (3) | US7829720B2 (da) |
EP (3) | EP2980074A1 (da) |
JP (1) | JP5086069B2 (da) |
KR (1) | KR101153606B1 (da) |
AU (2) | AU2005240622B2 (da) |
BR (1) | BRPI0509595B8 (da) |
CA (2) | CA2777216A1 (da) |
CY (1) | CY1116919T1 (da) |
DK (1) | DK1755596T5 (da) |
ES (1) | ES2552219T3 (da) |
HR (1) | HRP20150962T2 (da) |
HU (1) | HUE026242T2 (da) |
IL (1) | IL178965A (da) |
MX (1) | MXPA06012612A (da) |
NO (1) | NO341013B1 (da) |
PL (1) | PL1755596T3 (da) |
PT (1) | PT1755596E (da) |
RS (1) | RS54284B1 (da) |
SI (1) | SI1755596T1 (da) |
WO (1) | WO2005108349A2 (da) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200534879A (en) * | 2004-03-25 | 2005-11-01 | Bristol Myers Squibb Co | Coated tablet formulation and method |
US20050256314A1 (en) * | 2004-05-04 | 2005-11-17 | Soojin Kim | Process employing controlled crystallization in forming crystals of a pharmaceutical |
US7829720B2 (en) | 2004-05-04 | 2010-11-09 | Bristol-Myers Squibb Company | Process for preparing atazanavir bisulfate and novel forms |
TWI354569B (en) * | 2004-05-28 | 2011-12-21 | Bristol Myers Squibb Co | Coated tablet formulation and method |
US7642049B2 (en) | 2006-06-30 | 2010-01-05 | Bristol-Myers Squibb Company | Method for identifying HIV-1 protease inhibitors with reduced metabolic affects through detection of human resistin polymorphisms |
MX2009013565A (es) | 2007-06-12 | 2010-06-02 | Concert Pharmaceuticals Inc | Derivados de azapeptidos. |
AU2008268627A1 (en) * | 2007-06-22 | 2008-12-31 | Bristol-Myers Squibb Company | Tableted compositions containing atazanavir |
US20100183715A1 (en) | 2007-06-22 | 2010-07-22 | Bristo-Meyers Squibb Company | Tableted compositions containing atazanavir |
DE602008005896D1 (de) * | 2007-06-22 | 2011-05-12 | Bristol Myers Squibb Co | Tablettierte atazanavirhaltige zusammensetzungen |
AU2008268630A1 (en) * | 2007-06-22 | 2008-12-31 | Bristol-Myers Squibb Company | Tableted compositions containing atazanavir |
WO2010079497A2 (en) * | 2009-01-12 | 2010-07-15 | Hetero Research Foundation | Novel polymorph of atazanavir sulfate |
WO2011027324A1 (en) | 2009-09-03 | 2011-03-10 | Ranbaxy Laboratories Limited | Polymorphic forms of atazanavir sulfate |
HRP20211826T1 (hr) | 2009-10-26 | 2022-03-04 | Merck Sharp & Dohme Corp. | Čvrste farmaceutske kompozicije koje sadrže inhibitor integraze |
US20130203759A1 (en) | 2010-04-09 | 2013-08-08 | Faranak Nikfar | ATAZANAVIR SULFATE FORMULATIONS WITH IMPROVED pH EFFECT |
EA201390464A1 (ru) | 2010-09-28 | 2013-08-30 | Рациофарм Гмбх | Способ сухой обработки атазанавира |
US20140343290A1 (en) | 2011-07-27 | 2014-11-20 | Rakesh Kumar Singh | Process for the preparation of atazanavir or its bisulfate salt |
US8461347B2 (en) | 2011-08-05 | 2013-06-11 | Scinopharm Taiwan, Ltd. | Process for preparing form A of atazanavir sulfate |
US9382207B2 (en) | 2012-08-24 | 2016-07-05 | Laurus Labs Private Limited | Process for the preparation of atazanavir bisulfate |
WO2014036690A1 (zh) * | 2012-09-04 | 2014-03-13 | 上海迪赛诺化学制药有限公司 | 制备阿扎那韦硫酸氢盐a型结晶的方法 |
ZA201401073B (en) | 2013-02-12 | 2015-12-23 | Cipla Ltd | Process for preparing atazanavir sulphate |
CN115215792A (zh) * | 2022-06-27 | 2022-10-21 | 江西富祥药业股份有限公司 | 一种制备阿扎那韦或其硫酸盐的方法 |
Family Cites Families (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US658435A (en) * | 1900-03-22 | 1900-09-25 | William T Ginn | Coal-digger. |
US4022776A (en) | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]ethyl-8-hydroxycarbostyril derivatives |
US3980637A (en) | 1975-03-17 | 1976-09-14 | Bristol-Myers Company | Production of amoxicillin |
DE3403329A1 (de) | 1984-02-01 | 1985-08-01 | Horst Dr. 4019 Monheim Zerbe | Pharmazeutisches produkt in form von pellets mit kontinuierlicher, verzoegerter wirkstoffabgabe |
JPS6186211A (ja) | 1984-10-04 | 1986-05-01 | 日本碍子株式会社 | セラミックス複合構造体及びその製造法 |
FR2623810B2 (fr) | 1987-02-17 | 1992-01-24 | Sanofi Sa | Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant |
US5158777A (en) | 1990-02-16 | 1992-10-27 | E. R. Squibb & Sons, Inc. | Captopril formulation providing increased duration of activity |
CA2068402C (en) | 1991-06-14 | 1998-09-22 | Michael R. Hoy | Taste mask coatings for preparation of chewable pharmaceutical tablets |
US5428048A (en) | 1993-11-08 | 1995-06-27 | American Home Products Corporation | Aryl-N-hydroxyureas as inhibitors of 5-lipoxygenase and anto-arteriosclerotic agents |
GB9407386D0 (en) | 1994-04-14 | 1994-06-08 | Smithkline Beecham Plc | Pharmaceutical formulation |
TW483763B (en) | 1994-09-02 | 2002-04-21 | Astra Ab | Pharmaceutical composition comprising of ramipril and dihydropyridine compound |
US5849911A (en) | 1996-04-22 | 1998-12-15 | Novartis Finance Corporation | Antivirally active heterocyclic azahexane derivatives |
KR100486051B1 (ko) * | 1996-04-22 | 2005-09-09 | 노파르티스 아게 | 항바이러스활성헤테로시클릭아자헥산유도체 |
GB9715896D0 (en) | 1997-07-28 | 1997-10-01 | Sca Packaging Ltd | Containers |
US6087383A (en) * | 1998-01-20 | 2000-07-11 | Bristol-Myers Squibb Company | Bisulfate salt of HIV protease inhibitor |
FR2779726B1 (fr) | 1998-06-15 | 2001-05-18 | Sanofi Sa | Forme polymorphe de l'hydrogenosulfate de clopidogrel |
CN1161341C (zh) | 1999-03-22 | 2004-08-11 | 布里斯托尔-迈尔斯斯奎布公司 | cGMP磷酸二酯酶的稠合吡啶并哒嗪抑制剂 |
US6414002B1 (en) | 1999-09-22 | 2002-07-02 | Bristol-Myers Squibb Company | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
AU1304601A (en) | 1999-11-11 | 2001-06-06 | Kyorin Pharmaceutical Co. Ltd. | Solid preparations for oral use |
JP2003520226A (ja) | 2000-01-21 | 2003-07-02 | ノバルティス アクチエンゲゼルシャフト | ジペプチジルペプチダーゼ−iv阻害剤および抗糖尿病薬剤を含む組合せ物 |
US6254888B1 (en) | 2000-01-28 | 2001-07-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for coating pharmaceutical dosage forms |
US6395767B2 (en) | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
YU34501A (sh) | 2000-05-26 | 2003-10-31 | Pfizer Products Inc. | Postupak reaktivne kristalizacije radi povećanja veličine čestica |
IL145106A0 (en) | 2000-08-30 | 2002-06-30 | Pfizer Prod Inc | Intermittent administration of a geowth hormone secretagogue |
US6670344B2 (en) | 2000-09-14 | 2003-12-30 | Bristol-Myers Squibb Company | Combretastatin A-4 phosphate prodrug mono- and di-organic amine salts, mono- and di- amino acid salts, and mono- and di-amino acid ester salts |
US6867300B2 (en) | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
US6946146B2 (en) | 2001-04-18 | 2005-09-20 | Nostrum Pharmaceuticals Inc. | Coating for a sustained release pharmaceutical composition |
EP1467717A1 (en) | 2002-01-15 | 2004-10-20 | Ranbaxy Laboratories Limited | Stable pharmaceutical compositions comprising ace inhibitor(s) |
KR100456833B1 (ko) | 2002-08-01 | 2004-11-10 | 주식회사 대웅 | 아목시실린 및 클라불라네이트를 함유하는 유핵정 |
TW200534879A (en) | 2004-03-25 | 2005-11-01 | Bristol Myers Squibb Co | Coated tablet formulation and method |
US7829720B2 (en) | 2004-05-04 | 2010-11-09 | Bristol-Myers Squibb Company | Process for preparing atazanavir bisulfate and novel forms |
US20050256314A1 (en) | 2004-05-04 | 2005-11-17 | Soojin Kim | Process employing controlled crystallization in forming crystals of a pharmaceutical |
US20050288343A1 (en) | 2004-05-19 | 2005-12-29 | Andrew Rusowicz | Process of preparing substituted carbamates and intermediates thereof |
TWI354569B (en) | 2004-05-28 | 2011-12-21 | Bristol Myers Squibb Co | Coated tablet formulation and method |
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2005
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- 2005-05-03 WO PCT/US2005/015333 patent/WO2005108349A2/en active Application Filing
- 2005-05-03 DK DK05744537.1T patent/DK1755596T5/da active
- 2005-05-03 SI SI200532001T patent/SI1755596T1/sl unknown
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- 2005-05-03 KR KR1020067025370A patent/KR101153606B1/ko active IP Right Grant
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- 2005-05-03 CA CA2777216A patent/CA2777216A1/en not_active Abandoned
- 2005-05-03 EP EP15180557.9A patent/EP2980074A1/en not_active Ceased
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