ZA200108058B - Taxane formulations having improved solubility. - Google Patents

Info

Publication number

ZA200108058B

ZA200108058B ZA200108058A ZA200108058A ZA200108058B ZA 200108058 B ZA200108058 B ZA 200108058B ZA 200108058 A ZA200108058 A ZA 200108058A ZA 200108058 A ZA200108058 A ZA 200108058A ZA 200108058 B ZA200108058 B ZA 200108058B

Authority

ZA

South Africa

Prior art keywords

composition

benzoyl

substituted

heterocyclo

pyridyl

Prior art date

2000-02-02

Links

• Espacenet
• Global Dossier
• Discuss

• 229940123237 Taxane Drugs 0.000 title claims description 122
• 239000000203 mixture Substances 0.000 title claims description 114
• 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 title claims description 80
• 238000009472 formulation Methods 0.000 title description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 153
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 140
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 70
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 67
• 125000001544 thienyl group Chemical group 0.000 claims description 65
• 125000002541 furyl group Chemical group 0.000 claims description 64
• 125000001145 hydrido group Chemical group *[H] 0.000 claims description 64
• 125000003342 alkenyl group Chemical group 0.000 claims description 63
• 229930194542 Keto Natural products 0.000 claims description 54
• 125000000468 ketone group Chemical group 0.000 claims description 54
• 125000004423 acyloxy group Chemical group 0.000 claims description 53
• 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 47
• 229930012538 Paclitaxel Natural products 0.000 claims description 46
• 229960001592 paclitaxel Drugs 0.000 claims description 46
• 125000000304 alkynyl group Chemical group 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 27
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
• 239000002904 solvent Substances 0.000 claims description 19
• 238000007911 parenteral administration Methods 0.000 claims description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
• 239000004359 castor oil Substances 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 5
• 239000011780 sodium chloride Substances 0.000 claims description 5
• 235000019438 castor oil Nutrition 0.000 claims description 4
• 239000008121 dextrose Substances 0.000 claims description 4
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
• 239000008151 electrolyte solution Substances 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 8
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 8
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
• -1 2-ethylhexyl Chemical group 0.000 description 411
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 316
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 109
• 239000000243 solution Substances 0.000 description 69
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 59
• 125000004076 pyridyl group Chemical group 0.000 description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 50
• 125000001424 substituent group Chemical group 0.000 description 46
• 150000001875 compounds Chemical class 0.000 description 44
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• 230000000259 anti-tumor effect Effects 0.000 description 37
• 150000002148 esters Chemical class 0.000 description 33
• 125000004122 cyclic group Chemical group 0.000 description 32
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 31
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• 235000019441 ethanol Nutrition 0.000 description 24
• 125000000753 cycloalkyl group Chemical group 0.000 description 23
• 125000005842 heteroatom Chemical group 0.000 description 23
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
• 239000000839 emulsion Substances 0.000 description 20
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• 125000003545 alkoxy group Chemical group 0.000 description 18
• 239000008389 polyethoxylated castor oil Substances 0.000 description 17
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 16
• 229910052799 carbon Inorganic materials 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 150000001241 acetals Chemical class 0.000 description 14
• 125000003368 amide group Chemical group 0.000 description 14
• 125000004104 aryloxy group Chemical group 0.000 description 14
• 125000001072 heteroaryl group Chemical group 0.000 description 14
• BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 14
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 14
• 150000003573 thiols Chemical class 0.000 description 14
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 13
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 13
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 13
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• 125000005980 hexynyl group Chemical group 0.000 description 12
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 12
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 12
• 125000005981 pentynyl group Chemical group 0.000 description 12
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 12
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 11
• 125000001033 ether group Chemical group 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 238000011282 treatment Methods 0.000 description 11
• 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 10
• 235000014113 dietary fatty acids Nutrition 0.000 description 10
• 239000000194 fatty acid Substances 0.000 description 10
• 229930195729 fatty acid Natural products 0.000 description 10
• 125000006038 hexenyl group Chemical group 0.000 description 10
• URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 150000002431 hydrogen Chemical class 0.000 description 9
• 239000003549 soybean oil Substances 0.000 description 9
• 235000012424 soybean oil Nutrition 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 229920002472 Starch Polymers 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
• 125000005843 halogen group Chemical group 0.000 description 8
• 238000001802 infusion Methods 0.000 description 8
• 238000000034 method Methods 0.000 description 8
• 239000001301 oxygen Substances 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• 229920001223 polyethylene glycol Polymers 0.000 description 8
• 125000006239 protecting group Chemical group 0.000 description 8
• RCINICONZNJXQF-XAZOAEDWSA-N taxol® Chemical compound O([C@@H]1[C@@]2(CC(C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3(C21)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-XAZOAEDWSA-N 0.000 description 8
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
• 230000002411 adverse Effects 0.000 description 7
• 150000001408 amides Chemical class 0.000 description 7
• 229910052796 boron Inorganic materials 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 235000011187 glycerol Nutrition 0.000 description 7
• 150000002430 hydrocarbons Chemical class 0.000 description 7
• 238000001990 intravenous administration Methods 0.000 description 7
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• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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