AU2008313622A1 - Solid dispersion product of N-aryl urea-based drugs - Google Patents

Solid dispersion product of N-aryl urea-based drugs Download PDF

Info

Publication number: AU2008313622A1
Authority: AU; Australia
Prior art keywords: group; phenyl; amino; alkyl; urea
Prior art date: 2007-10-19
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

Application number

AU2008313622A

Other languages

English (en)

Inventor

Tanja Heitermann

Rudolf Schroeder

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott GmbH and Co KG

Original Assignee

Abbott GmbH and Co KG

Priority date (The priority date 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 date listed.)

2007-10-19

Filing date

2008-10-17

Publication date

2009-04-23

2008-10-17 Application filed by Abbott GmbH and Co KG filed Critical Abbott GmbH and Co KG

2009-04-23 Publication of AU2008313622A1 publication Critical patent/AU2008313622A1/en

Status Abandoned legal-status Critical Current

Links

239000007962 solid dispersion Substances 0.000 title claims description 53
239000004202 carbamide Substances 0.000 title description 48
229940079593 drug Drugs 0.000 title description 8
239000003814 drug Substances 0.000 title description 8
239000001257 hydrogen Substances 0.000 claims description 266
229910052739 hydrogen Inorganic materials 0.000 claims description 266
125000000217 alkyl group Chemical group 0.000 claims description 243
125000003545 alkoxy group Chemical group 0.000 claims description 121
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 115
150000001875 compounds Chemical class 0.000 claims description 113
-1 polyol fatty acid esters Chemical class 0.000 claims description 99
125000004438 haloalkoxy group Chemical group 0.000 claims description 91
229910003827 NRaRb Inorganic materials 0.000 claims description 83
125000001188 haloalkyl group Chemical group 0.000 claims description 76
125000004104 aryloxy group Chemical group 0.000 claims description 74
125000000623 heterocyclic group Chemical group 0.000 claims description 67
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 65
125000004093 cyano group Chemical group *C#N 0.000 claims description 62
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 57
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 56
125000003118 aryl group Chemical group 0.000 claims description 51
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 47
239000013543 active substance Substances 0.000 claims description 45
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 45
125000000753 cycloalkyl group Chemical group 0.000 claims description 45
125000003342 alkenyl group Chemical group 0.000 claims description 44
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 38
238000000034 method Methods 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 37
229920000858 Cyclodextrin Polymers 0.000 claims description 36
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 36
239000003795 chemical substances by application Substances 0.000 claims description 35
239000007788 liquid Substances 0.000 claims description 35
125000003710 aryl alkyl group Chemical group 0.000 claims description 34
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 34
239000002904 solvent Substances 0.000 claims description 33
229920000642 polymer Polymers 0.000 claims description 29
125000001424 substituent group Chemical group 0.000 claims description 27
230000008569 process Effects 0.000 claims description 25
239000008180 pharmaceutical surfactant Substances 0.000 claims description 22
239000004094 surface-active agent Substances 0.000 claims description 22
235000014113 dietary fatty acids Nutrition 0.000 claims description 21
239000000194 fatty acid Substances 0.000 claims description 21
229930195729 fatty acid Natural products 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
229920001577 copolymer Polymers 0.000 claims description 18
238000001035 drying Methods 0.000 claims description 14
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 13
MPVGZUGXCQEXTM-UHFFFAOYSA-N linifanib Chemical compound CC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)C=2C=3C(N)=NNC=3C=CC=2)=C1 MPVGZUGXCQEXTM-UHFFFAOYSA-N 0.000 claims description 13
229920005862 polyol Polymers 0.000 claims description 13
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
229910052701 rubidium Inorganic materials 0.000 claims description 12
239000000945 filler Substances 0.000 claims description 11
125000005456 glyceride group Chemical group 0.000 claims description 11
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 9
239000002552 dosage form Substances 0.000 claims description 9
229920001223 polyethylene glycol Polymers 0.000 claims description 9
ZAKOWWREFLAJOT-ADUHFSDSSA-N [2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate Chemical group CC(=O)OC1=C(C)C(C)=C2OC(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-ADUHFSDSSA-N 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
239000002202 Polyethylene glycol Substances 0.000 claims description 7
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 7
229920001519 homopolymer Polymers 0.000 claims description 7
239000011159 matrix material Substances 0.000 claims description 7
238000001694 spray drying Methods 0.000 claims description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 7
125000005243 carbonyl alkyl group Chemical group 0.000 claims description 6
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 6
229920001515 polyalkylene glycol Polymers 0.000 claims description 6
239000000654 additive Substances 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
229920002678 cellulose Polymers 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
239000007884 disintegrant Substances 0.000 claims description 4
239000006185 dispersion Substances 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
125000003827 glycol group Chemical group 0.000 claims description 4
150000002632 lipids Chemical class 0.000 claims description 4
239000000314 lubricant Substances 0.000 claims description 4
239000004067 bulking agent Substances 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 3
229920003086 cellulose ether Polymers 0.000 claims description 3
238000002036 drum drying Methods 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
239000012453 solvate Substances 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims description 2
239000001913 cellulose Substances 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 6
125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
229920002774 Maltodextrin Polymers 0.000 claims 2
229940000425 combination drug Drugs 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229920001281 polyalkylene Polymers 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 190
235000013350 formula milk Nutrition 0.000 description 134
125000005843 halogen group Chemical group 0.000 description 107
125000002887 hydroxy group Chemical group [H]O* 0.000 description 91
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 89
150000002431 hydrogen Chemical class 0.000 description 73
235000013877 carbamide Nutrition 0.000 description 48
239000000047 product Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
229940097362 cyclodextrins Drugs 0.000 description 23
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 23
125000003944 tolyl group Chemical group 0.000 description 17
239000000243 solution Substances 0.000 description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000002950 monocyclic group Chemical group 0.000 description 10
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 10
241000282472 Canis lupus familiaris Species 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
125000004122 cyclic group Chemical group 0.000 description 9
229920000036 polyvinylpyrrolidone Polymers 0.000 description 9
239000001267 polyvinylpyrrolidone Substances 0.000 description 9
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 9
239000010408 film Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
239000002253 acid Substances 0.000 description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
229920000136 polysorbate Polymers 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000000306 component Substances 0.000 description 6
125000000392 cycloalkenyl group Chemical group 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000007789 gas Substances 0.000 description 6
125000004433 nitrogen atom Chemical group N* 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
229960003511 macrogol Drugs 0.000 description 5
239000000463 material Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
229940086735 succinate Drugs 0.000 description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
230000008901 benefit Effects 0.000 description 4
125000000068 chlorophenyl group Chemical group 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000178 monomer Substances 0.000 description 4
125000002757 morpholinyl group Chemical group 0.000 description 4
125000004043 oxo group Chemical group O=* 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
229940002612 prodrug Drugs 0.000 description 4
239000000651 prodrug Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
229940100515 sorbitan Drugs 0.000 description 4
229940035044 sorbitan monolaurate Drugs 0.000 description 4
238000005809 transesterification reaction Methods 0.000 description 4
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 3
ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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239000004480 active ingredient Substances 0.000 description 3
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XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
229940040544 bromides Drugs 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
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125000002541 furyl group Chemical group 0.000 description 3
239000008187 granular material Substances 0.000 description 3
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125000000842 isoxazolyl group Chemical group 0.000 description 3
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239000001593 sorbitan monooleate Substances 0.000 description 3
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239000000126 substance Substances 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
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102000001253 Protein Kinase Human genes 0.000 description 2
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239000004147 Sorbitan trioleate Substances 0.000 description 2
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
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125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
DTHHUAXKOMWYBI-UHFFFAOYSA-N oxadiazolidine Chemical compound C1CONN1 DTHHUAXKOMWYBI-UHFFFAOYSA-N 0.000 description 1
NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011236 particulate material Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
WVTKBKWTSCPRNU-UHFFFAOYSA-N rac-Tetrandrin Natural products O1C(C(=CC=2CCN3C)OC)=CC=2C3CC(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2CC2N(C)CCC3=CC(OC)=C(OC)C1=C23 WVTKBKWTSCPRNU-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229940126586 small molecule drug Drugs 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
239000001570 sorbitan monopalmitate Substances 0.000 description 1
229940031953 sorbitan monopalmitate Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
RLTPJVKHGBFGQA-UHFFFAOYSA-N thiadiazolidine Chemical compound C1CSNN1 RLTPJVKHGBFGQA-UHFFFAOYSA-N 0.000 description 1
GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biophysics (AREA)
Molecular Biology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

AU2008313622A 2007-10-19 2008-10-17 Solid dispersion product of N-aryl urea-based drugs Abandoned AU2008313622A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US99961807P	2007-10-19	2007-10-19
US60/999,618		2007-10-19
PCT/EP2008/064076 WO2009050291A2 (fr)	2007-10-19	2008-10-17	Produit de dispersion solide de médicaments de type n-aryle à base d'urée

Publications (1)

Publication Number	Publication Date
AU2008313622A1 true AU2008313622A1 (en)	2009-04-23

Family

ID=40089463

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2008313622A Abandoned AU2008313622A1 (en)	2007-10-19	2008-10-17	Solid dispersion product of N-aryl urea-based drugs

Country Status (18)

Country	Link
EP (1)	EP2197425A2 (fr)
JP (1)	JP2011500649A (fr)
KR (1)	KR20100087170A (fr)
CN (1)	CN101827584A (fr)
AU (1)	AU2008313622A1 (fr)
BR (1)	BRPI0818340A2 (fr)
CA (1)	CA2699301A1 (fr)
CO (1)	CO6270206A2 (fr)
CR (1)	CR11442A (fr)
DO (1)	DOP2010000117A (fr)
EC (1)	ECSP10010183A (fr)
GT (1)	GT201000102A (fr)
MX (1)	MX2010004291A (fr)
PA (1)	PA8800101A1 (fr)
RU (1)	RU2010119929A (fr)
UA (1)	UA100865C2 (fr)
WO (1)	WO2009050291A2 (fr)
ZA (1)	ZA201002095B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2009100176A2 (fr) *	2008-02-07	2009-08-13	Abbott Laboratories	Forme pharmaceutique pour administration orale d’un inhibiteur de tyrosine kinase
AR077975A1 (es)	2009-08-28	2011-10-05	Irm Llc	Derivados de pirazol pirimidina y composiciones como inhibidores de cinasa de proteina
PH12012502432A1 (en) *	2010-06-09	2013-02-11	Abbvie Inc	Solid dispersions containing kinase inhibitors
BR112014011223A8 (pt)	2011-11-11	2023-01-31	Novartis Ag	Método de tratar uma doença proliferativa
KR102091295B1 (ko) *	2011-11-23	2020-03-19	어레이 바이오파마 인크.	제약 제제
WO2014003678A1 (fr) *	2012-06-28	2014-01-03	Xspray Microparticles Ab	Compositions pharmaceutiques comprenant de l'ambrisentan et des particules de dispersion solide contenant du tadalafil
WO2014003677A1 (fr) *	2012-06-28	2014-01-03	Xspray Microparticles Ab	Compositions pharmaceutiques comprenant des particules de dispersion solide contenant du tadalafil
JP6796083B2 (ja)	2015-06-09	2020-12-02	カプスゲル・ベルギウム・ナムローゼ・フェンノートシャップＣａｐｓｕｇｅｌＢｅｌｇｉｕｍＮＶ	カプセル中の薬剤の噴霧乾燥ディスパーションからの迅速な溶解を達成するための製剤

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20070104780A1 (en) *	2005-10-25	2007-05-10	Lipari John M	Formulation comprising a drug of low water solubility and method of use thereof
WO2007066189A2 (fr) *	2005-12-09	2007-06-14	Pfizer Products Inc.	Sels, promedicaments et formulations de 1-[5-(4-amino-7-isopropyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-2-methoxy-phenyl]-3-(2,4-dichloro-phenyl)-uree
EP2089003A1 (fr) *	2006-11-09	2009-08-19	Abbott GmbH & Co. KG	Forme de dosage pharmaceutique pour l'administration orale d'un inhibiteur de la tyrosine kinase

2008
- 2008-10-17 AU AU2008313622A patent/AU2008313622A1/en not_active Abandoned
- 2008-10-17 WO PCT/EP2008/064076 patent/WO2009050291A2/fr not_active Ceased
- 2008-10-17 CN CN200880112150A patent/CN101827584A/zh active Pending
- 2008-10-17 MX MX2010004291A patent/MX2010004291A/es not_active Application Discontinuation
- 2008-10-17 PA PA20088800101A patent/PA8800101A1/es unknown
- 2008-10-17 RU RU2010119929/15A patent/RU2010119929A/ru not_active Application Discontinuation
- 2008-10-17 JP JP2010529408A patent/JP2011500649A/ja active Pending
- 2008-10-17 UA UAA201006029A patent/UA100865C2/ru unknown
- 2008-10-17 CA CA2699301A patent/CA2699301A1/fr not_active Abandoned
- 2008-10-17 BR BRPI0818340 patent/BRPI0818340A2/pt not_active IP Right Cessation
- 2008-10-17 KR KR1020107010979A patent/KR20100087170A/ko not_active Withdrawn
- 2008-10-17 EP EP08839333A patent/EP2197425A2/fr not_active Withdrawn
2010
- 2010-03-24 ZA ZA2010/02095A patent/ZA201002095B/en unknown
- 2010-04-16 GT GT201000102A patent/GT201000102A/es unknown
- 2010-04-16 DO DO2010000117A patent/DOP2010000117A/es unknown
- 2010-04-27 CO CO10049271A patent/CO6270206A2/es not_active Application Discontinuation
- 2010-05-17 EC EC2010010183A patent/ECSP10010183A/es unknown
- 2010-05-19 CR CR11442A patent/CR11442A/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
MX2010004291A (es)	2010-08-02
RU2010119929A (ru)	2011-11-27
JP2011500649A (ja)	2011-01-06
CN101827584A (zh)	2010-09-08
CO6270206A2 (es)	2011-04-20
UA100865C2 (ru)	2013-02-11
ECSP10010183A (es)	2010-06-29
WO2009050291A2 (fr)	2009-04-23
PA8800101A1 (es)	2009-05-15
ZA201002095B (en)	2011-11-30
CR11442A (es)	2010-09-06
DOP2010000117A (es)	2010-05-15
GT201000102A (es)	2012-03-12
CA2699301A1 (fr)	2009-04-23
KR20100087170A (ko)	2010-08-03
WO2009050291A3 (fr)	2010-04-08
EP2197425A2 (fr)	2010-06-23
BRPI0818340A2 (pt)	2015-04-22

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AU2008313622A1 (en)	2009-04-23	Solid dispersion product of N-aryl urea-based drugs
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US10493161B2 (en)	2019-12-03	Solution for spray drying comprising hypromellose acetate succinate and method for producing solid dispersion
RS56382B1 (sr)	2017-12-29	Farmaceutski preparati koji sadrže sigma receptorske ligande
JP2003503380A (ja)	2003-01-28	無定形硝酸エステルおよびその製剤組成物
WO2002040054A1 (fr)	2002-05-23	Preparation pharmaceutique contenant de la copolyvidone
TW202216117A (zh)	2022-05-01	經口用醫藥組成物及其製造方法
JP2001511796A (ja)	2001-08-14	環状四級アンモニウム化合物を経口投与するための乾燥形態の薬学的調合剤
JP2003527424A (ja)	2003-09-16	オキサゾリジノン錠剤製剤
KR100912196B1 (ko)	2009-08-14	Ｌｔｂ4 길항제를 함유하는 약제학적 제형
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