CA2718567A1 - C(10) ethyl ester and c(10) cyclopropyl ester substituted taxanes - Google Patents

Info

Publication number

CA2718567A1

CA2718567A1 CA2718567A CA2718567A CA2718567A1 CA 2718567 A1 CA2718567 A1 CA 2718567A1 CA 2718567 A CA2718567 A CA 2718567A CA 2718567 A CA2718567 A CA 2718567A CA 2718567 A1 CA2718567 A1 CA 2718567A1

Authority

CA

Canada

Prior art keywords

pharmaceutical composition

carcinoma

taxane

tumor

compound

Prior art date

2008-03-31

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 229940123237 Taxane Drugs 0.000 title claims abstract description 71
• 125000004494 ethyl ester group Chemical group 0.000 title abstract description 3
• 238000000034 method Methods 0.000 claims abstract description 53
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 48
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 182
• 206010028980 Neoplasm Diseases 0.000 claims description 119
• 239000000203 mixture Substances 0.000 claims description 88
• 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 description 73
• 229960003668 docetaxel Drugs 0.000 claims description 71
• 239000000243 solution Substances 0.000 claims description 69
• 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 description 49
• 230000004614 tumor growth Effects 0.000 claims description 49
• 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 description 35
• 229930012538 Paclitaxel Natural products 0.000 claims description 34
• 229960001592 paclitaxel Drugs 0.000 claims description 34
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 32
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 25
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
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• 125000001544 thienyl group Chemical group 0.000 claims description 13
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
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• SRQMASZDGSTJCU-UHFFFAOYSA-N cyclopentyloxycarbamic acid Chemical group OC(=O)NOC1CCCC1 SRQMASZDGSTJCU-UHFFFAOYSA-N 0.000 abstract description 2
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• -1 cyclopropylcarbonyloxy Chemical group 0.000 description 71
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• YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)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 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 22
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