JP2007536245A5 - - Google Patents
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- JP2007536245A5 JP2007536245A5 JP2007511502A JP2007511502A JP2007536245A5 JP 2007536245 A5 JP2007536245 A5 JP 2007536245A5 JP 2007511502 A JP2007511502 A JP 2007511502A JP 2007511502 A JP2007511502 A JP 2007511502A JP 2007536245 A5 JP2007536245 A5 JP 2007536245A5
- Authority
- JP
- Japan
- Prior art keywords
- atazanavir
- total
- time
- sulfuric acid
- bisulfate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 18
- DQSGVVGOPRWTKI-QVFAWCHISA-M hydrogen sulfate;methyl N-[(2S)-1-[2-[(2S,3S)-2-hydroxy-3-[[(2S)-2-(methoxycarbonylamino)-3,3-dimethylbutanoyl]amino]-4-phenylbutyl]-2-[(4-pyridin-2-ylphenyl)methyl]hydrazinyl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound OS([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-M 0.000 claims 17
- 239000012458 free base Substances 0.000 claims 16
- AXRYRYVKAWYZBR-GASGPIRDSA-N Atazanavir Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 AXRYRYVKAWYZBR-GASGPIRDSA-N 0.000 claims 12
- 229960003277 atazanavir Drugs 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 239000002253 acid Substances 0.000 claims 10
- 238000002425 crystallisation Methods 0.000 claims 9
- 230000005712 crystallization Effects 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 8
- 239000000463 material Substances 0.000 claims 6
- 239000002585 base Substances 0.000 claims 5
- 238000001035 drying Methods 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000011780 sodium chloride Substances 0.000 claims 5
- 238000007792 addition Methods 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N n-methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 2
- CYQYBRMAYUBANC-UHFFFAOYSA-N 1,1-dichloroethane;N,N-dimethylformamide Chemical compound CC(Cl)Cl.CN(C)C=O CYQYBRMAYUBANC-UHFFFAOYSA-N 0.000 claims 1
- FWZUNOYOVVKUNF-UHFFFAOYSA-N Allyl acetate Chemical compound CC(=O)OCC=C FWZUNOYOVVKUNF-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N N,N-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 claims 1
- DSRXQXXHDIAVJT-UHFFFAOYSA-N acetonitrile;N,N-dimethylformamide Chemical compound CC#N.CN(C)C=O DSRXQXXHDIAVJT-UHFFFAOYSA-N 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- -1 alkaline earth metal carbonate Chemical class 0.000 claims 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
- 229910000316 alkaline earth metal phosphate Inorganic materials 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000007493 shaping process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000005550 wet granulation Methods 0.000 claims 1
- YTDMTTYOLYTDMS-LLVKDONJSA-N CC(C)(C)[C@@H](C(O[n]1nnc2ccccc12)=O)NC(OC)=O Chemical compound CC(C)(C)[C@@H](C(O[n]1nnc2ccccc12)=O)NC(OC)=O YTDMTTYOLYTDMS-LLVKDONJSA-N 0.000 description 1
- OKXLMWIFNMTTDR-PSWJWLENSA-N CCC(C)(CC)[C@@H](C(N[C@@H](Cc1ccccc1)[C@H](CN(Cc(cc1)ccc1-c1ccccn1)NC([C@H](C(C)(C)C)NC(OC)=O)=O)O)=O)NC(OC)=O Chemical compound CCC(C)(CC)[C@@H](C(N[C@@H](Cc1ccccc1)[C@H](CN(Cc(cc1)ccc1-c1ccccn1)NC([C@H](C(C)(C)C)NC(OC)=O)=O)O)=O)NC(OC)=O OKXLMWIFNMTTDR-PSWJWLENSA-N 0.000 description 1
Claims (21)
- A型結晶形の重硫酸アタザナビルの製造方法であって、アセトン、アセトンおよびN−メチルピロリドンの混合物、エタノール、またはエタノールおよびアセトンの混合物である有機溶媒中で、アタザナビル遊離塩基の溶液を該アタザナビル遊離塩基の約15重量%未満が反応する量の濃硫酸の一部と最初に反応させ、重硫酸アタザナビルのA型結晶の種晶を該反応混合物に加え、重硫酸アタザナビルの結晶が形成するように、追加の濃硫酸を増加速度で多段階にて加えて重硫酸アタザナビルの結晶形成を行い、該重硫酸アタザナビルを乾燥して、A型結晶を形成することを特徴とする方法。
- 該アタザナビル遊離塩基の溶液を、用いられる硫酸の全重量の5〜15%と最初に反応させる、請求項1の方法。
- 該アタザナビル遊離塩基の溶液を、用いられる硫酸の全重量の8〜12%と最初に反応させる、請求項1の方法。
- 該アタザナビル遊離塩基を35〜55℃の温度範囲で硫酸の一部と最初に反応させる、請求項1の方法。
- 該アタザナビル遊離塩基の溶液を35〜55℃の温度範囲に加熱した後、硫酸と反応させる、請求項1の方法。
- アタザナビル遊離塩基および硫酸の反応混合物に、アタザナビル遊離塩基の重量に基づいて0.1〜80重量%のA型結晶の種晶を加える、請求項1の方法。
- 種晶を加えた反応混合物を35〜55℃の温度範囲で加熱する、請求項1の方法。
- 該アタザナビル遊離塩基のための有機溶媒がアセトンおよびN−メチルピロリドンの混合物である、請求項1の方法。
- 重硫酸アタザナビルのA型結晶を、少なくとも24時間、少なくとも約95%RHの高い相対湿度に付し、次いで乾燥することを特徴とする、該重硫酸アタザナビルのCパターン物質の製造方法。
- (a)アセトン、アセトンおよびN−メチルピロリドンの混合物、エタノール、またはエタノールおよびアセトンの混合物である有機溶媒中で、アタザナビル遊離塩基の溶液を該アタザナビル遊離塩基の約15重量%未満が反応する量の濃硫酸の一部と最初に反応させ、重硫酸アタザナビルのA型結晶の種晶を該反応混合物に加え、重硫酸アタザナビルの結晶が形成するように、追加の濃硫酸を増加速度で多段階にて加えて重硫酸アタザナビルの結晶形成を行い、該重硫酸アタザナビルを乾燥して、A型結晶を形成し;
(b)水中で、段階(a)からの重硫酸アタザナビルのA型結晶を懸濁し、該懸濁液を乾燥して、Cパターン物質を形成するか;または
(c)段階(a)からの重硫酸アタザナビルのA型結晶を、少なくとも24時間、95%RHより高い相対湿度に付し、段階(a)からのCパターン物質を形成するか;または
(d)段階(a)からの重硫酸アタザナビルのA型結晶を湿式造粒し、該湿式造粒物を乾燥し、Cパターン物質を形成するか;または
(e)段階(a)からのA型結晶を1つ以上の製剤用賦形剤と混合し、生じた混合物を湿式造粒し、該賦形剤と混合したCパターン物質を直接的に形成すること
を特徴とする、重硫酸アタザナビルのCパターン物質の製造方法。 - A型結晶形の重硫酸アタザナビル:
Vtime=経過時間内に加えられた硫酸の量
Vtotal=90%添加を表す酸の全量
time=結晶化における経過時間
timetotal=結晶化の全時間または酸を添加するための全時間]
に従う増加速度で加えることを特徴とする方法。 - 該塩基が、アルカリ金属水酸化物、アルカリ土類金属水酸化物、アルカリ金属炭酸塩、アルカリ土類金属炭酸塩、アルカリ金属リン酸塩、アルカリ土類金属リン酸塩または有機塩基である、請求項11の方法。
- 該塩基が、NaOH、KOH、Mg(OH)2、K2HPO4、MgCO3、Na2CO3、K2CO3、トリエチルアミン、ジイソプロピルエチルアミンまたはN−メチルモルホリンであり、該有機溶媒が、塩化メチレン、酢酸エチル、ジクロロエタン、テトラヒドロフラン、アセトニトリルまたはN,N−ジメチルホルムアミドである、請求項14の方法。
- 該トリアミン塩および該活性エステル体を、30〜40℃の温度範囲で反応させる、請求項11の方法。
- 該トリアミン塩および該活性エステル体を、該塩基としてK2HPO4の存在下で、該溶媒として塩化メチレン中で反応させる、請求項16の方法。
- 遊離塩基、アセトンおよびN−メチルピロリドンの混合物に重硫酸アタザナビルの結晶の種晶を加える段階を含むことを特徴とする、請求項11の方法。
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US56804304P | 2004-05-04 | 2004-05-04 | |
US60/568,043 | 2004-05-04 | ||
US60753304P | 2004-09-07 | 2004-09-07 | |
US60/607,533 | 2004-09-07 | ||
US11/119,558 | 2005-05-02 | ||
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 (3)
Publication Number | Publication Date |
---|---|
JP2007536245A JP2007536245A (ja) | 2007-12-13 |
JP2007536245A5 true JP2007536245A5 (ja) | 2009-10-22 |
JP5086069B2 JP5086069B2 (ja) | 2012-11-28 |
Family
ID=35310244
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2007511502A Active JP5086069B2 (ja) | 2004-05-04 | 2005-05-03 | 重硫酸アタザナビルおよび新規形態の製造方法 |
Country Status (20)
Country | Link |
---|---|
US (3) | US7829720B2 (ja) |
EP (3) | EP2980074A1 (ja) |
JP (1) | JP5086069B2 (ja) |
KR (1) | KR101153606B1 (ja) |
AU (2) | AU2005240622B2 (ja) |
BR (1) | BRPI0509595B8 (ja) |
CA (2) | CA2565629C (ja) |
CY (1) | CY1116919T1 (ja) |
DK (1) | DK1755596T5 (ja) |
ES (1) | ES2552219T3 (ja) |
HR (1) | HRP20150962T2 (ja) |
HU (1) | HUE026242T2 (ja) |
IL (1) | IL178965A (ja) |
MX (1) | MXPA06012612A (ja) |
NO (1) | NO341013B1 (ja) |
PL (1) | PL1755596T3 (ja) |
PT (1) | PT1755596E (ja) |
RS (1) | RS54284B1 (ja) |
SI (1) | SI1755596T1 (ja) |
WO (1) | WO2005108349A2 (ja) |
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BR0306928A (pt) | 2002-01-15 | 2004-11-09 | Ranbaxy Lab Ltd | Composições farmacêuticas estáveis compreendendo inibidores de enzimas conversoras de angiotensina (ace) |
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 |
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 |
US20050288343A1 (en) | 2004-05-19 | 2005-12-29 | Andrew Rusowicz | Process of preparing substituted carbamates and intermediates thereof |
TWI415635B (zh) | 2004-05-28 | 2013-11-21 | 必治妥施貴寶公司 | 加衣錠片調製物及製備彼之方法 |
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