CA2608952A1 - Pharmaceutical compostions comprising an amorphous form of a vegf-r inhibitor - Google Patents

Info

Publication number

CA2608952A1

CA2608952A1 CA002608952A CA2608952A CA2608952A1 CA 2608952 A1 CA2608952 A1 CA 2608952A1 CA 002608952 A CA002608952 A CA 002608952A CA 2608952 A CA2608952 A CA 2608952A CA 2608952 A1 CA2608952 A1 CA 2608952A1

Authority

CA

Canada

Prior art keywords

compound

composition

cellulose acetate

matrix

methyl cellulose

Prior art date

2005-05-19

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

• 150000001875 compounds Chemical class 0.000 claims abstract description 69
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 239000012453 solvate Substances 0.000 claims abstract description 27
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 11
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 11
• WRSXUNSJGJUKHE-UHFFFAOYSA-N indazole Chemical compound C1=CC=C[C]2C=NN=C21 WRSXUNSJGJUKHE-UHFFFAOYSA-N 0.000 claims abstract 2
• 229940126062 Compound A Drugs 0.000 claims description 269
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 269
• 239000000203 mixture Substances 0.000 claims description 211
• 239000006185 dispersion Substances 0.000 claims description 81
• 239000007787 solid Substances 0.000 claims description 68
• 239000011159 matrix material Substances 0.000 claims description 61
• -1 carboxymethyl ethyl Chemical group 0.000 claims description 60
• 238000000034 method Methods 0.000 claims description 56
• 239000002904 solvent Substances 0.000 claims description 51
• 239000007921 spray Substances 0.000 claims description 28
• 229920002301 cellulose acetate Polymers 0.000 claims description 27
• 238000001727 in vivo Methods 0.000 claims description 25
• 230000008569 process Effects 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 23
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 23
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 21
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 19
• GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 claims description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 17
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 16
• 230000002159 abnormal effect Effects 0.000 claims description 16
• 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 16
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 16
• 229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 15
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
• 230000010261 cell growth Effects 0.000 claims description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 238000000338 in vitro Methods 0.000 claims description 13
• 229920000609 methyl cellulose Polymers 0.000 claims description 13
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• 241000124008 Mammalia Species 0.000 claims description 12
• 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 11
• 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 11
• 229960002900 methylcellulose Drugs 0.000 claims description 11
• 238000001704 evaporation Methods 0.000 claims description 10
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• 210000002966 serum Anatomy 0.000 claims description 9
• 125000005591 trimellitate group Chemical group 0.000 claims description 9
• 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 8
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• 239000001856 Ethyl cellulose Substances 0.000 claims description 7
• 229940081734 cellulose acetate phthalate Drugs 0.000 claims description 7
• 229920001249 ethyl cellulose Polymers 0.000 claims description 7
• 235000019325 ethyl cellulose Nutrition 0.000 claims description 7
• 229920000058 polyacrylate Polymers 0.000 claims description 7
• 229920000193 polymethacrylate Polymers 0.000 claims description 7
• 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 6
• 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 6
• 239000004372 Polyvinyl alcohol Substances 0.000 claims description 6
• ZNPLZHBZUSCANM-UHFFFAOYSA-N acetic acid;benzene-1,3-dicarboxylic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC(C(O)=O)=C1 ZNPLZHBZUSCANM-UHFFFAOYSA-N 0.000 claims description 6
• FMTQGBMMIVVKSN-UHFFFAOYSA-N acetic acid;terephthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 FMTQGBMMIVVKSN-UHFFFAOYSA-N 0.000 claims description 6
• 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 6
• 229920006163 vinyl copolymer Polymers 0.000 claims description 6
• 229960004667 ethyl cellulose Drugs 0.000 claims description 5
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• 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
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• 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 3
• 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
• 239000011118 polyvinyl acetate Substances 0.000 claims description 3
• 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
• 102000004169 proteins and genes Human genes 0.000 claims description 3
• 239000002202 Polyethylene glycol Substances 0.000 claims description 2
• 229920001451 polypropylene glycol Polymers 0.000 claims description 2
• 229920000642 polymer Polymers 0.000 description 125
• 239000000243 solution Substances 0.000 description 52
• 239000003112 inhibitor Substances 0.000 description 39
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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• 239000007789 gas Substances 0.000 description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 150000002148 esters Chemical class 0.000 description 12
• 239000002953 phosphate buffered saline Substances 0.000 description 12
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• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 10
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• MNJVRJDLRVPLFE-UHFFFAOYSA-N etoricoxib Chemical compound C1=NC(C)=CC=C1C1=NC=C(Cl)C=C1C1=CC=C(S(C)(=O)=O)C=C1 MNJVRJDLRVPLFE-UHFFFAOYSA-N 0.000 description 9
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 8
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