JP2011517455A5 - - Google Patents
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- JP2011517455A5 JP2011517455A5 JP2011503034A JP2011503034A JP2011517455A5 JP 2011517455 A5 JP2011517455 A5 JP 2011517455A5 JP 2011503034 A JP2011503034 A JP 2011503034A JP 2011503034 A JP2011503034 A JP 2011503034A JP 2011517455 A5 JP2011517455 A5 JP 2011517455A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- composition according
- taxane
- cancer
- cyclobutyl
- 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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- 239000008194 pharmaceutical composition Substances 0.000 claims 23
- 229940123237 Taxane Drugs 0.000 claims 12
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 206010009944 Colon cancer Diseases 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 206010038389 Renal cancer Diseases 0.000 claims 4
- 208000029742 colonic neoplasm Diseases 0.000 claims 4
- 201000010982 kidney cancer Diseases 0.000 claims 4
- 201000001441 melanoma Diseases 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 108010078791 Carrier Proteins Proteins 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010033128 Ovarian cancer Diseases 0.000 claims 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229940100688 oral solution Drugs 0.000 claims 3
- 238000007911 parenteral administration Methods 0.000 claims 3
- 239000008389 polyethoxylated castor oil Substances 0.000 claims 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims 3
- 229920000053 polysorbate 80 Polymers 0.000 claims 3
- 229940068968 polysorbate 80 Drugs 0.000 claims 3
- 210000004881 tumor cell Anatomy 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 239000002960 lipid emulsion Substances 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 102000043966 ABC-type transporter activity proteins Human genes 0.000 claims 1
- 108010006533 ATP-Binding Cassette Transporters Proteins 0.000 claims 1
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims 1
- 206010052747 Adenocarcinoma pancreas Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 102100022595 Broad substrate specificity ATP-binding cassette transporter ABCG2 Human genes 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 101000823298 Homo sapiens Broad substrate specificity ATP-binding cassette transporter ABCG2 Proteins 0.000 claims 1
- 101000956263 Homo sapiens Uncharacterized protein C19orf48 Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims 1
- 206010027406 Mesothelioma Diseases 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 102100038573 Uncharacterized protein C19orf48 Human genes 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 208000030381 cutaneous melanoma Diseases 0.000 claims 1
- 239000012153 distilled water Substances 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 210000002919 epithelial cell Anatomy 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 230000036457 multidrug resistance Effects 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 201000002094 pancreatic adenocarcinoma Diseases 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 claims 1
- 201000003708 skin melanoma Diseases 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 BC(*C[C@@]1C)(C([C@@](*)[C@](C[C@@](C(C)=C2[C@]3COC(C4CC4)=O)OC([C@@]([C@](c4ccc[s]4)NC(OC4CCC4)=O)O)=O)([C@@]2(CC)C#C)O)[C@@]1(C*)OC(C)=O)C3=O Chemical compound BC(*C[C@@]1C)(C([C@@](*)[C@](C[C@@](C(C)=C2[C@]3COC(C4CC4)=O)OC([C@@]([C@](c4ccc[s]4)NC(OC4CCC4)=O)O)=O)([C@@]2(CC)C#C)O)[C@@]1(C*)OC(C)=O)C3=O 0.000 description 2
Claims (28)
- 式（1）：
で示される構造を持つタキサン。 - R10aがエチルであり、X10がシクロブチルもしくはシクロペンチルであるか、
R 10a がシクロプロピルであり、X 10 がシクロブチルもしくはシクロペンチルであるか、
R 10a がエチルもしくはシクロプロピルであり、X 10 がシクロブチルであるか、または
R 10a がエチルもしくはシクロプロピルであり、X 10 がシクロペンチルであり、
X 3 が2-チエニルである、請求項1に記載のタキサン。 - 式（1aa）、（1bb）、（1ab）、および（1ba）：
- 式（1bb）：
- 式（1A）、（1B）、（1C）、および（1D）：
- 式（1）：
で示される構造を持つタキサンと、少なくとも1つの医薬上許容される担体とを含む医薬組成物。 - R10aがエチルであり、X10がシクロブチルもしくはシクロペンチルであるか、
R 10a がシクロプロピルであり、X 10 がシクロブチルもしくはシクロペンチルであるか、
R 10a がエチルもしくはシクロプロピルであり、X 10 がシクロブチルであるか、または
R 10a がエチルもしくはシクロプロピルであり、X 10 がシクロペンチルであり、
X 3 が2-チエニルである、請求項6に記載の医薬組成物。 - タキサンが、式（1aa）、（1bb）、（1ab）、および（1ba）：
- タキサンが、式（1bb）：
- タキサンが、式（1A）、（1B）、（1C）、および（1D）：
- タキサンの濃度が約0.01mg/mL〜10mg/mLである、請求項6に記載の医薬組成物。
- 組成物が経口投与用の単一投与単位形であり、その投与単位形が患者の体表面積1m2あたり少なくとも20mg、または約25mg〜約400mg、または約50mg〜約200mgのタキサンを含有する、請求項6に記載の医薬組成物。
- 組成物が非経口投与用の単一投与単位形であり、その投与単位形が患者の体表面積1m2あたり少なくとも20mg、または約40mg〜約400mg、または約60mg〜約350mg、または約50mg〜約100mgのタキサンを含有する、請求項6に記載の医薬組成物。
- 約10％までのエタノールを含む、請求項6に記載の医薬組成物。
- 経口投与用、例えば経口溶液の形態である、請求項14に記載の医薬組成物。
- 少なくとも約90％の蒸留水を含む経口溶液の形態である、請求項15に記載の医薬組成物。
- 約10％未満の界面活性剤、例えばポリソルベート80、ポリエトキシル化ヒマシ油、またはそれらの組み合わせを含む経口溶液の形態である、請求項15に記載の医薬組成物。
- 非経口投与用である、請求項14に記載の医薬組成物。
- エマルションの形態である、請求項18に記載の医薬組成物。
- エタノール溶液と脂肪エマルションとを混合することによって製造され、脂肪エマルションが例えば約10〜約20％の脂肪を含有する、請求項19に記載の医薬組成物。
- 溶液、例えば少なくとも約85％の食塩液を含む溶液であり、約10％未満の界面活性剤、例えばポリソルベート80、ポリエトキシル化ヒマシ油、もしくはそれらの組み合わせを含んでもよい、請求項18に記載の医薬組成物。
- 哺乳動物において腫瘍成長を阻害するための、請求項6〜21のいずれかに記載の医薬組成物。
- 腫瘍が多剤耐性を示す腫瘍細胞を含み、多剤耐性腫瘍細胞は例えば薬物排出トランスポーターを過剰発現させる腫瘍細胞であり、薬物排出トランスポーターは例えばATP結合カセットトランスポーターであり、ATP結合カセットトランスポーターは例えばP-糖タンパク質、MDR関連タンパク質、乳がん耐性タンパク質、多剤耐性関連タンパク質、またはそれらの組み合わせである、請求項22に記載の医薬組成物。
- 腫瘍がパクリタキセルまたはドセタキセルに対して耐性である、請求項22または23に記載の医薬組成物。
- 腫瘍が上皮細胞癌である、請求項22〜24のいずれかに記載の医薬組成物。
- 腫瘍が、脳膠芽腫、乳癌、大腸癌、腎臓癌、肝臓癌、肺癌、卵巣癌、膵臓癌、腎臓癌、もしくは皮膚メラノーマ、またはSNB-19脳膠芽腫、HCT116大腸癌、HT-29大腸癌、DLD-1大腸癌、A549肺癌、HOP-18肺癌、MSTO-211H中皮腫、A375メラノーマ、MALME-3メラノーマ、SK-MEL-28メラノーマ、OVCAR4卵巣癌、OVCAR5卵巣癌、PANC-1膵腺癌、BxPC-3膵臓癌、786-0腎臓癌、もしくはTK-10腎臓癌である、請求項22〜25のいずれかに記載の医薬組成物。
- 経口投与または非経口投与される、請求項22〜26のいずれかに記載の医薬組成物。
- 界面活性剤、例えばポリソルベート80、ポリエトキシル化ヒマシ油、またはそれらの組み合わせを含む、請求項22〜27のいずれかに記載の医薬組成物。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4101708P | 2008-03-31 | 2008-03-31 | |
| US61/041,017 | 2008-03-31 | ||
| PCT/US2009/038119 WO2009145981A1 (en) | 2008-03-31 | 2009-03-24 | C(10) ethyl ester and c(10) cyclopropyl ester substituted taxanes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011517455A JP2011517455A (ja) | 2011-06-09 |
| JP2011517455A5 true JP2011517455A5 (ja) | 2012-05-17 |
Family
ID=41377463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503034A Pending JP2011517455A (ja) | 2008-03-31 | 2009-03-24 | Ｃ（１０）エチルエステルおよびｃ（１０）シクロプロピルエステル置換タキサン |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8242166B2 (ja) |
| EP (1) | EP2276755A4 (ja) |
| JP (1) | JP2011517455A (ja) |
| CA (1) | CA2718567A1 (ja) |
| WO (1) | WO2009145981A1 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009002425A2 (en) * | 2007-06-22 | 2008-12-31 | Scidose Llc | Solubilized formulation of docetaxel without tween 80 |
| JP2011514349A (ja) * | 2008-03-07 | 2011-05-06 | サイドース・エルエルシー | フルベストラント配合物 |
| US8541465B2 (en) * | 2009-10-19 | 2013-09-24 | Scidose, Llc | Docetaxel formulations with lipoic acid and/or dihydrolipoic acid |
| US7772274B1 (en) | 2009-10-19 | 2010-08-10 | Scidose, Llc | Docetaxel formulations with lipoic acid |
| US20110092579A1 (en) * | 2009-10-19 | 2011-04-21 | Scidose Llc | Solubilized formulation of docetaxel |
| US8476310B2 (en) | 2009-10-19 | 2013-07-02 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US8912228B2 (en) | 2009-10-19 | 2014-12-16 | Scidose Llc | Docetaxel formulations with lipoic acid |
| US11179468B2 (en) | 2012-04-09 | 2021-11-23 | Eagle Pharmaceuticals, Inc. | Fulvestrant formulations |
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| AU710156B2 (en) | 1996-07-15 | 1999-09-16 | Kabushiki Kaisha Yakult Honsha | Taxane derivatives and drugs containing the same |
| US5811452A (en) | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
| US5912264A (en) | 1997-03-03 | 1999-06-15 | Bristol-Myers Squibb Company | 6-halo-or nitrate-substituted paclitaxels |
| CA2206739C (en) | 1997-06-03 | 2006-10-10 | Ensuiko Sugar Refining Co., Ltd. | Taxoid derivative and method of producing thereof |
| US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| JPH1192468A (ja) | 1997-09-17 | 1999-04-06 | Yakult Honsha Co Ltd | 新規なタキサン誘導体 |
| WO1999032473A1 (en) * | 1997-12-19 | 1999-07-01 | Kabushiki Kaisha Yakult Honsha | Taxane derivatives |
| US6156789A (en) | 1998-03-17 | 2000-12-05 | Rhone-Poulenc Rorer S.A. | Method for treating abnormal cell proliferation in the brain |
| JP2003026673A (ja) | 1999-03-05 | 2003-01-29 | Asahi Kasei Corp | 骨形成促進剤 |
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| HUP0600302A2 (en) * | 2000-02-02 | 2006-07-28 | Univ Florida State Res Found | C10 ester substituted taxanes as antitumor agents |
| TR200102857T1 (tr) | 2000-02-02 | 2002-06-21 | Florida State University Research Foundation Inc. | Antitümör ajanları olarak C7 karbonat ikameli taksanlar |
| CA2367661A1 (en) | 2000-02-02 | 2001-08-09 | Robert A. Holton | Taxane formulations having improved solubility |
| KR20010111580A (ko) | 2000-02-02 | 2001-12-19 | 플로리다 스테이트 유니버시티 리서치 파운데이션, 인크 | 개선된 용해도를 갖는 탁산 제형물 |
| JP2003522171A (ja) | 2000-02-02 | 2003-07-22 | フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド | 抗腫瘍剤としてのｃ１０カーボネート置換タキサン |
| IT1319168B1 (it) | 2000-03-17 | 2003-09-26 | Indena Spa | Derivati di condensazione ad attivita' antitumorale, loro metodo dipreparazione e formulazioni che li contengono. |
| JP2008530122A (ja) | 2005-02-14 | 2008-08-07 | フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド | Ｃ１０シクロプロピルエステル置換タキサン組成物 |
| JP5571380B2 (ja) * | 2006-07-24 | 2014-08-13 | ルミナス バイオサイエンシズ，インコーポレイテッド | オストワルド熟成を減少させた水不溶性の医薬品物質の固体ナノ粒子処方物 |
-
2009
- 2009-03-24 JP JP2011503034A patent/JP2011517455A/ja active Pending
- 2009-03-24 EP EP09755344A patent/EP2276755A4/en not_active Withdrawn
- 2009-03-24 WO PCT/US2009/038119 patent/WO2009145981A1/en not_active Ceased
- 2009-03-24 CA CA2718567A patent/CA2718567A1/en not_active Abandoned
- 2009-03-24 US US12/409,884 patent/US8242166B2/en not_active Expired - Fee Related
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