HUE032527T2 - Sulphoalkyl ether cyclodextrin and corticosteroid inhalation preparation - Google Patents

Info

Publication number

HUE032527T2

HUE032527T2 HUE05704917A HUE05704917A HUE032527T2 HU E032527 T2 HUE032527 T2 HU E032527T2 HU E05704917 A HUE05704917 A HU E05704917A HU E05704917 A HUE05704917 A HU E05704917A HU E032527 T2 HUE032527 T2 HU E032527T2

Authority

HU

Hungary

Prior art keywords

sae

corticosteroid

iko

formulation

cyclodextrin

Prior art date

2003-12-31

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000203 mixture Substances 0.000 title claims description 303
• 238000009472 formulation Methods 0.000 title description 216
• 239000003246 corticosteroid Substances 0.000 title description 200
• 229920000858 Cyclodextrin Polymers 0.000 title description 182
• 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 title description 132
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 17
• 125000004964 sulfoalkyl group Chemical group 0.000 title description 10
• 239000000725 suspension Substances 0.000 claims description 141
• -1 amino amino amino Chemical group 0.000 claims description 92
• 239000003814 drug Substances 0.000 claims description 91
• 238000000034 method Methods 0.000 claims description 70
• 150000001875 compounds Chemical class 0.000 claims description 46
• 239000003795 chemical substances by application Substances 0.000 claims description 43
• 239000007787 solid Substances 0.000 claims description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
• 238000011282 treatment Methods 0.000 claims description 12
• 229940124597 therapeutic agent Drugs 0.000 claims description 10
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
• 239000000556 agonist Substances 0.000 claims description 4
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 3
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 3
• 235000003599 food sweetener Nutrition 0.000 claims description 3
• 229940039009 isoproterenol Drugs 0.000 claims description 3
• 229960004502 levodopa Drugs 0.000 claims description 3
• 239000003765 sweetening agent Substances 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims 2
• PJISLFCKHOHLLP-UHFFFAOYSA-N 2-diethoxyphosphorylsulfanyl-n,n-diethylethanamine Chemical compound CCOP(=O)(OCC)SCCN(CC)CC PJISLFCKHOHLLP-UHFFFAOYSA-N 0.000 claims 1
• 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 claims 1
• 235000010044 Hernandia moerenhoutiana Nutrition 0.000 claims 1
• 244000084296 Hernandia moerenhoutiana Species 0.000 claims 1
• 241001272567 Hominoidea Species 0.000 claims 1
• KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 0.000 claims 1
• 230000005856 abnormality Effects 0.000 claims 1
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• 239000013256 coordination polymer Substances 0.000 claims 1
• 230000005713 exacerbation Effects 0.000 claims 1
• 239000004816 latex Substances 0.000 claims 1
• 229920000126 latex Polymers 0.000 claims 1
• 239000004571 lime Substances 0.000 claims 1
• 210000001989 nasopharynx Anatomy 0.000 claims 1
• 229910052596 spinel Inorganic materials 0.000 claims 1
• 239000011029 spinel Substances 0.000 claims 1
• 239000007858 starting material Substances 0.000 claims 1
• 239000000243 solution Substances 0.000 description 239
• VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 185
• 229960004436 budesonide Drugs 0.000 description 146
• 239000006199 nebulizer Substances 0.000 description 113
• 238000002663 nebulization Methods 0.000 description 99
• 229940079593 drug Drugs 0.000 description 72
• WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 69
• 229960004853 betadex Drugs 0.000 description 66
• 229940097362 cyclodextrins Drugs 0.000 description 52
• KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 43
• 239000002245 particle Substances 0.000 description 43
• GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 42
• 239000007788 liquid Substances 0.000 description 40
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 36
• 239000013543 active substance Substances 0.000 description 32
• ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 32
• 239000012669 liquid formulation Substances 0.000 description 29
• 210000004072 lung Anatomy 0.000 description 29
• 238000002360 preparation method Methods 0.000 description 28
• 230000002685 pulmonary effect Effects 0.000 description 27
• 235000002639 sodium chloride Nutrition 0.000 description 27
• 238000012384 transportation and delivery Methods 0.000 description 27
• 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 26
• 229940043377 alpha-cyclodextrin Drugs 0.000 description 26
• HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 25
• 229950000210 beclometasone dipropionate Drugs 0.000 description 25
• 230000001965 increasing effect Effects 0.000 description 25
• 239000000843 powder Substances 0.000 description 25
• 239000000443 aerosol Substances 0.000 description 23
• 238000006467 substitution reaction Methods 0.000 description 23
• 102100032341 PCNA-interacting partner Human genes 0.000 description 22
• 101710196737 PCNA-interacting partner Proteins 0.000 description 22
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
• 239000001116 FEMA 4028 Substances 0.000 description 21
• 230000027455 binding Effects 0.000 description 19
• 150000003839 salts Chemical class 0.000 description 18
• NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 17
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
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• 239000002253 acid Substances 0.000 description 16
• 238000003860 storage Methods 0.000 description 16
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
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• 229940092705 beclomethasone Drugs 0.000 description 15
• 230000008901 benefit Effects 0.000 description 15
• 238000010668 complexation reaction Methods 0.000 description 15
• 229960001334 corticosteroids Drugs 0.000 description 15
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
• 239000008365 aqueous carrier Substances 0.000 description 14
• 239000000126 substance Substances 0.000 description 14
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• 208000006673 asthma Diseases 0.000 description 13
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 13
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• 229960002714 fluticasone Drugs 0.000 description 12
• MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 12
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• MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 12
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