CA2867121C - Pharmaceutical compositions comprising fatty acid esters - Google Patents
Pharmaceutical compositions comprising fatty acid esters Download PDFInfo
- Publication number
- CA2867121C CA2867121C CA2867121A CA2867121A CA2867121C CA 2867121 C CA2867121 C CA 2867121C CA 2867121 A CA2867121 A CA 2867121A CA 2867121 A CA2867121 A CA 2867121A CA 2867121 C CA2867121 C CA 2867121C
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- composition
- compound
- weight ratio
- polysorbate
- disorder
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 110
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 55
- 239000000194 fatty acid Substances 0.000 title claims abstract description 55
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 55
- -1 fatty acid esters Chemical class 0.000 title claims description 99
- 239000000203 mixture Substances 0.000 claims abstract description 100
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 claims abstract description 68
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims abstract description 40
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims abstract description 40
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims abstract description 40
- 229940093471 ethyl oleate Drugs 0.000 claims abstract description 40
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 claims abstract description 34
- 239000000164 antipsychotic agent Substances 0.000 claims abstract description 33
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 127
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 70
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 64
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 64
- 229940068977 polysorbate 20 Drugs 0.000 claims description 64
- 125000005907 alkyl ester group Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 38
- 150000004677 hydrates Chemical class 0.000 claims description 35
- 239000012453 solvate Substances 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 239000008365 aqueous carrier Substances 0.000 claims description 32
- 239000007924 injection Substances 0.000 claims description 26
- 238000002347 injection Methods 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 24
- 208000028017 Psychotic disease Diseases 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 201000000980 schizophrenia Diseases 0.000 claims description 16
- 208000020925 Bipolar disease Diseases 0.000 claims description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- 239000013049 sediment Substances 0.000 claims description 11
- 206010026749 Mania Diseases 0.000 claims description 10
- 239000000872 buffer Substances 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 230000036506 anxiety Effects 0.000 claims description 9
- 206010003805 Autism Diseases 0.000 claims description 7
- 208000020706 Autistic disease Diseases 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 7
- 206010022998 Irritability Diseases 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 208000020186 Schizophreniform disease Diseases 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- 239000008135 aqueous vehicle Substances 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 229940095064 tartrate Drugs 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000008351 acetate buffer Substances 0.000 claims description 3
- 229940102213 injectable suspension Drugs 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000012384 transportation and delivery Methods 0.000 abstract description 4
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 description 71
- 229960004372 aripiprazole Drugs 0.000 description 67
- 239000000306 component Substances 0.000 description 48
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 40
- 229960005017 olanzapine Drugs 0.000 description 38
- 235000002639 sodium chloride Nutrition 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 229940079593 drug Drugs 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- 125000001931 aliphatic group Chemical group 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- PQXKDMSYBGKCJA-CVTJIBDQSA-N lurasidone Chemical group C1=CC=C2C(N3CCN(CC3)C[C@@H]3CCCC[C@H]3CN3C(=O)[C@@H]4[C@H]5CC[C@H](C5)[C@@H]4C3=O)=NSC2=C1 PQXKDMSYBGKCJA-CVTJIBDQSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 229960001432 lurasidone Drugs 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000007972 injectable composition Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 101150041968 CDC13 gene Proteins 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000000561 anti-psychotic effect Effects 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 238000013265 extended release Methods 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 229940126534 drug product Drugs 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 102100038968 WAP four-disulfide core domain protein 1 Human genes 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 6
- 229940088679 drug related substance Drugs 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229940049964 oleate Drugs 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229940005529 antipsychotics Drugs 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000007918 intramuscular administration Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229940105132 myristate Drugs 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 4
- 150000003904 phospholipids Chemical class 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 3
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 206010022095 Injection Site reaction Diseases 0.000 description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 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 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002953 phosphate buffered saline Substances 0.000 description 3
- 150000008105 phosphatidylcholines Chemical class 0.000 description 3
- DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 230000003442 weekly effect Effects 0.000 description 3
- OQQOAWVKVDAJOI-UHFFFAOYSA-N (2-dodecanoyloxy-3-hydroxypropyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCC OQQOAWVKVDAJOI-UHFFFAOYSA-N 0.000 description 2
- DRAWQKGUORNASA-UHFFFAOYSA-N (2-hydroxy-3-octadec-9-enoyloxypropyl) octadec-9-enoate Chemical compound CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCC=CCCCCCCCC DRAWQKGUORNASA-UHFFFAOYSA-N 0.000 description 2
- ZQBULZYTDGUSSK-UHFFFAOYSA-N (3-hydroxy-2-octanoyloxypropyl) octanoate Chemical compound CCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCC ZQBULZYTDGUSSK-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 2
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229940056213 abilify Drugs 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003693 atypical antipsychotic agent Substances 0.000 description 2
- 239000008228 bacteriostatic water for injection Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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| US201261612734P | 2012-03-19 | 2012-03-19 | |
| US61/612,734 | 2012-03-19 | ||
| PCT/US2013/030916 WO2013142198A1 (en) | 2012-03-19 | 2013-03-13 | Pharmaaceutical compositions comprising fatty acid esters |
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| CA2867121A1 CA2867121A1 (en) | 2013-09-26 |
| CA2867121C true CA2867121C (en) | 2021-05-25 |
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| PL2445502T5 (pl) | 2009-06-25 | 2023-03-13 | Alkermes Pharma Ireland Limited | Związki heterocykliczne do leczenia zaburzeń neurologicznych i psychologicznych |
| PT2685979T (pt) | 2011-03-18 | 2016-12-02 | Alkermes Pharma Ireland Ltd | Composições farmacêuticas injetáveis compreendendo um antipsicótico solúvel em água, laurato de sorbitano e polissorbato 20 |
| AU2013235526B2 (en) | 2012-03-19 | 2017-11-30 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| JP6219918B2 (ja) | 2012-03-19 | 2017-10-25 | アルカームス ファーマ アイルランド リミテッド | グリセロールエステルを含む医薬組成物 |
| CA2867121C (en) | 2012-03-19 | 2021-05-25 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising fatty acid esters |
| US9193685B2 (en) | 2012-09-19 | 2015-11-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| WO2015143145A1 (en) * | 2014-03-20 | 2015-09-24 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| WO2016026822A1 (en) * | 2014-08-18 | 2016-02-25 | Alkermes Pharma Ireland Limited | Aripiprazole prodrug compositions |
| US10016415B2 (en) | 2014-08-18 | 2018-07-10 | Alkermes Pharma Ireland Limited | Aripiprazole prodrug compositions |
| DK3185867T3 (da) * | 2014-08-25 | 2021-03-15 | Alkermes Pharma Ireland Ltd | Krystalliseringsfremgangsmåde af aripiprazolderivater i forlængede frigivelsesformuleringer til behandling af skizofreni |
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2013
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- 2013-03-13 WO PCT/US2013/030916 patent/WO2013142198A1/en not_active Ceased
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| AU2013235519A1 (en) | 2014-09-25 |
| EP2827868B1 (en) | 2019-11-13 |
| AU2013235519B9 (en) | 2017-10-05 |
| NZ630643A (en) | 2017-08-25 |
| WO2013142198A1 (en) | 2013-09-26 |
| JP6471089B2 (ja) | 2019-02-13 |
| AU2013235519B2 (en) | 2017-09-07 |
| US10004807B2 (en) | 2018-06-26 |
| HK1206596A1 (en) | 2016-01-15 |
| EP2827868A1 (en) | 2015-01-28 |
| JP2015510929A (ja) | 2015-04-13 |
| ES2765036T3 (es) | 2020-06-05 |
| CA2867121A1 (en) | 2013-09-26 |
| JP2018009031A (ja) | 2018-01-18 |
| EP2827868A4 (en) | 2015-11-11 |
| AU2013235519C1 (en) | 2018-04-26 |
| US20130267503A1 (en) | 2013-10-10 |
| EP2827868B8 (en) | 2019-12-18 |
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