JP5010279B2 - ジメトキシドセタキセル・アセトン溶媒和物およびその製造方法 - Google Patents
ジメトキシドセタキセル・アセトン溶媒和物およびその製造方法 Download PDFInfo
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims description 77
- 238000000034 method Methods 0.000 title claims description 13
- 239000012453 solvate Substances 0.000 title claims description 11
- -1 Dimethoxy docetaxel Chemical compound 0.000 title claims description 3
- 229960003668 docetaxel Drugs 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 9
- ZVAFCKLQJCZGAP-WDEREUQCSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-WDEREUQCSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000010899 nucleation Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 3
- VOXXWSYKYCBWHO-UHFFFAOYSA-N 3-phenyllactic acid Chemical compound OC(=O)C(O)CC1=CC=CC=C1 VOXXWSYKYCBWHO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 2
- ZHWDQYCJDJUYPP-UHFFFAOYSA-N 2-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)C1OC(C(=O)OCCCC)(C=2C=CC(OC)=CC=2)NC1C1=CC=CC=C1 ZHWDQYCJDJUYPP-UHFFFAOYSA-N 0.000 claims 1
- ZVAFCKLQJCZGAP-UHFFFAOYSA-N 2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000008213 purified water Substances 0.000 description 3
- BQGQGFJBNHUYLS-UHFFFAOYSA-N 2-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)NC(O)(C(O)=O)CC1=CC=CC=C1 BQGQGFJBNHUYLS-UHFFFAOYSA-N 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZHXYSICWKISVCX-VZXYPILPSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid;propan-2-one Chemical compound CC(C)=O.CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=CC=CC=C1 ZHXYSICWKISVCX-VZXYPILPSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- GOTMYRUZLYVSPC-UHFFFAOYSA-N 2-hydroxy-2-isocyanato-3-phenylpropanoic acid Chemical compound C(=O)=NC(C(=O)O)(CC1=CC=CC=C1)O GOTMYRUZLYVSPC-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Oncology (AREA)
- Hematology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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Description
− 4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートを、アセトン中に溶解させる、
− この溶液を水で処理する、
− この溶液に、該化合物のアセトン/水混合液中の懸濁液を用いて結晶種付け(seed)を行い、そして再び水で処理する、
− 得られた結晶を単離する、そして
− それらを減圧下で乾燥する。
アセトン約2L中に約92質量%の4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル207gを溶解させた溶液に精製水の940mLを、20±5℃の周囲温度で加え、そして次に、アセトン/水から単離した、2gの4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートを20mLおよびアセトン20mLの混合液中に懸濁した懸濁液を用いて、結晶種付け(seeding)を行った。混合液を攪拌しながら約10〜22時間放置し、そして精製水の1.5Lを4〜5時間かけて加えた。混合液を攪拌しながら約60〜90分間放置し、そして懸濁液を減圧下で濾過した。固形物(cake)をフィルター上で、アセトン450mLおよび精製水550mLから調製された溶液で洗浄し、そして、減圧下(0.7kPa)で4時間、55℃で、オーブン中で乾燥した。水を0.1%およびアセトンを7.2%含む(化学量論的な溶媒和物について、理論的には6.5%)4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネート・アセトンが得られた。
生成物を再度オーブン上に置き、連続して、0.7kPaの減圧下で60℃で18時間、相対湿度約80%(160mmHgの減圧下)の下で60℃で3時間、そして相対湿度約80%(200mmHgの減圧下)の下で70℃で18時間、乾燥させた。この段階で、水含量は0.2%であり、そしてアセトン含量は4.7%(194g)であった。この同じ段階で、このバッチの一部分を1g、5mmHgの減圧下で連続して80℃で18時間(残留アセトン含量は0.5%)、次いで、100℃で21時間(残留アセトン含量は0.02%)乾燥させた。残余物は5mmHgの減圧下で、80℃で31時間乾燥させた(アセトン1.7%、水0.3%、アッセイは96.5%のものに関して、純度は99%を超える)。
分析は、アントン・パール(Anton Paar)TTK温度室を装備したブルーカー(Bruker)D5000回析計により実施した。反射の設定はブラッグ・ブレンターノ(Bragg-Brentano)型(θ−θ)の集束配置(focusing geometry)を有していた。中空のアルミニウム試料ホルダー上に粉末を置いた。コバルト対陰極管(40kV/30mA)から鉄フィルターを通した入射光を供給した。放射線はCo Kα1(λ=1.7890Å)およびCo Kα2(λ=1.7929Å)の2つの波長で放射された。鉄による濾過は完全にはKβ放射(コバルトでλ=1.6208Å)を除去しなかったが、その一方で、まだKαダブレット(doublet)の強度の1%(製造者のデータ)のレベルで入射光に関与していた。
1H NMR スペクトル (400 MHz, CDC13, ppmでδ) : 1.20 (s, 3H), 1.22 (s, 3H), 1.37
(s, 9H), 1.67 (s, 1H), 1.72 (s, 3H), 1.80 (mt, 1H), 1.88 (s, 3H), 2.17 (s, 6H),
2.20〜2.40 (mt, 2H), 2.36 (s, 3H), 2.70 (mt, 1H), 3.30 (s, 3H), 3.46 (s, 3H), 3.47 (mt, 1H), 3.82 (d, J = 7.5 Hz, 1H), 3.86 (dd, J= 11 および 6.5 Hz, 1H), 4.17 (d,J = 8.5 Hz, 1H), 4.30 (d, J = 8.5 Hz, 1H), 4.63 (mt, 1H), 4.80 (s, 1H), 4.97 (ブロードd, J = 10 Hz, 1H), 5.27 (ブロードd, J = 10 Hz, 1H), 5.44 (d, J = 10 Hz, 1H), 5.64 (d, J = 7.5 Hz, 1H), 6.21 (t, J = 9 Hz, 1H), 7.25〜7.45 (mt, 5H), 7.49 (t, J = 7.5 Hz, 2H), 7,60 (ブロードt, J =7.5 Hz, 1H), 8.09 (d, J = 7.5 Hz, 2H)。
Claims (11)
- 4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートのアセトン溶媒和物の結晶。
- アセトンを5〜7質量%含んでいる、4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートのアセトン溶媒和物の結晶。
- 4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートをアセトンと水の混合液から結晶化することを含み、この溶液に該化合物のアセトン/水混合液中の懸濁液を用いて結晶種付けを行い、続いて水で処理することを含み、そして、得られた生成物を減圧下で乾燥することを含む、4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートのアセトン溶媒和物の結晶の製造方法。
- 結晶種付けは、アセトン/水の容量比が65/35から75/25の間の混合液中で1L当り60〜80gの濃度で行われる、請求項3に記載の方法。
- 結晶種付けは、アセトン/水の容量比が68/32の混合液中で行われる、請求項4に記載の方法。
- 沈殿の終了時のアセトン/水混合液が容量比で、最小で70/30から最大で30/70の間である、請求項3に記載の方法。
- 沈殿の終了時のアセトン/水混合液が容量比で45/55である、請求項6に記載の方法。
- 結晶化工程が20±5℃で行われる、請求項3〜7のいずれかに記載の方法。
- 乾燥は、30〜60℃の温度で、0.7kPaの領域の減圧下で、行われる、請求項3に記載の方法。
- 乾燥は、40℃の領域で行われる、請求項9に記載の方法。
- 製造は、4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,4S,5R)−3−tert−ブトキシカルボニル−2−(4−メトキシフェニル)−4−フェニルオキサゾリジン−5−カルボン酸エステルの酸媒体中での脱保護化によって得られた4−アセトキシ−2α−ベンゾイルオキシ−5β,20−エポキシ−1−ヒドロキシ−7β,10β−ジメトキシ−9−オキソタキサ−11−エン−13α−イル(2R,3S)−3−tert−ブトキシカルボニルアミノ−2−ヒドロキシ−3−フェニルプロピオネートのアセトン溶液から出発して直接に行われる、請求項3に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0311016A FR2859996B1 (fr) | 2003-09-19 | 2003-09-19 | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
FR0311016 | 2003-09-19 | ||
PCT/FR2004/002344 WO2005028462A1 (fr) | 2003-09-19 | 2004-09-16 | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
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JP2007505866A JP2007505866A (ja) | 2007-03-15 |
JP5010279B2 true JP5010279B2 (ja) | 2012-08-29 |
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JP2009533330A (ja) * | 2006-03-21 | 2009-09-17 | ドクター レディズ ラボラトリーズ リミテッド | ドセタキセルの多形体およびプロセス |
US7855591B2 (en) * | 2006-06-07 | 2010-12-21 | Atmel Corporation | Method and system for providing a charge pump very low voltage applications |
US7652522B2 (en) * | 2006-09-05 | 2010-01-26 | Atmel Corporation | High efficiency low cost bi-directional charge pump circuit for very low voltage applications |
JP2010516625A (ja) | 2007-01-24 | 2010-05-20 | インサート セラピューティクス, インコーポレイテッド | 制御された薬物送達のためのテザー基を有するポリマー−薬物コンジュゲート |
FR2926551A1 (fr) | 2008-01-17 | 2009-07-24 | Aventis Pharma Sa | Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation |
AU2013205442B2 (en) * | 2008-01-17 | 2016-05-12 | Aventis Pharma S.A. | Crystalline forms of dimethoxy docetaxel and methods for preparing same |
KR101671537B1 (ko) | 2008-08-11 | 2016-11-01 | 넥타르 테라퓨틱스 | 다분지형 중합체 알카노에이트 컨쥬게이트 |
FR2945211A1 (fr) * | 2009-05-06 | 2010-11-12 | Sanofi Aventis | Combinaison antitumorale comprenant la cabazitaxel et la capecitabine |
AU2015200149B2 (en) * | 2009-10-29 | 2016-12-01 | Aventis Pharma S.A. | Novel antitumoral use of cabazitaxel |
PT2493466T (pt) * | 2009-10-29 | 2021-03-29 | Sanofi Mature Ip | Nova utilização antifúngica do cabazitaxel |
CA2708489A1 (en) * | 2009-10-29 | 2011-04-29 | Aventis Pharma S.A. | Use of cabazitaxel and a prednisone or a prednisolone in the treatment of prostate cancer |
US10894087B2 (en) | 2010-12-22 | 2021-01-19 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
US20130331443A1 (en) | 2010-12-22 | 2013-12-12 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
ES2621800T3 (es) | 2011-04-12 | 2017-07-05 | Teva Pharmaceuticals International Gmbh | Formas de estado sólido de cabazitaxel y procesos de preparación de las mismas |
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