CA2036844A1 - Aerosol permettant une liberation reglee de microspheres de procaterol - Google Patents

Aerosol permettant une liberation reglee de microspheres de procaterol

Info

Publication number: CA2036844A1
Authority: CA; Canada
Prior art keywords: microspheres; formulation; albumin; propellant; agent
Prior art date: 1990-02-22
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

CA 2036844

Other languages

English (en)

Inventor

Hua-Pin Huang

Surendra C. Mehta

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.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

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.)

1990-02-22

Filing date

1991-02-21

Publication date

1991-08-23

1991-02-21 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1991-08-23 Publication of CA2036844A1 publication Critical patent/CA2036844A1/fr

Status Abandoned legal-status Critical Current

Links

239000004005 microsphere Substances 0.000 title claims abstract description 59
239000000443 aerosol Substances 0.000 title claims abstract description 37
238000013270 controlled release Methods 0.000 title claims abstract description 21
229960002288 procaterol Drugs 0.000 title abstract description 15
FKNXQNWAXFXVNW-BLLLJJGKSA-N procaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)[C@@H](NC(C)C)CC FKNXQNWAXFXVNW-BLLLJJGKSA-N 0.000 title abstract description 15
239000000203 mixture Substances 0.000 claims abstract description 39
102000009027 Albumins Human genes 0.000 claims abstract description 30
108010088751 Albumins Proteins 0.000 claims abstract description 30
239000013543 active substance Substances 0.000 claims abstract description 25
239000003380 propellant Substances 0.000 claims abstract description 22
239000003795 chemical substances by application Substances 0.000 claims abstract description 15
LZULAZTXJLWELL-UHFFFAOYSA-N methyl hex-5-ynoate Chemical compound COC(=O)CCCC#C LZULAZTXJLWELL-UHFFFAOYSA-N 0.000 claims abstract description 15
229960002789 procaterol hydrochloride Drugs 0.000 claims abstract description 15
239000006185 dispersion Substances 0.000 claims abstract description 10
230000003182 bronchodilatating effect Effects 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 3
238000009472 formulation Methods 0.000 claims description 14
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 13
239000003921 oil Substances 0.000 claims description 11
235000019198 oils Nutrition 0.000 claims description 11
235000012343 cottonseed oil Nutrition 0.000 claims description 8
239000000839 emulsion Substances 0.000 claims description 8
239000002385 cottonseed oil Substances 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
235000010323 ascorbic acid Nutrition 0.000 claims description 6
229960005070 ascorbic acid Drugs 0.000 claims description 6
239000011668 ascorbic acid Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
108091003079 Bovine Serum Albumin Proteins 0.000 claims description 5
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
235000019404 dichlorodifluoromethane Nutrition 0.000 claims description 5
239000003381 stabilizer Substances 0.000 claims description 5
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
239000007900 aqueous suspension Substances 0.000 claims description 4
229940098773 bovine serum albumin Drugs 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
108010071390 Serum Albumin Proteins 0.000 claims description 3
102000007562 Serum Albumin Human genes 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
238000000527 sonication Methods 0.000 claims description 2
229960000984 tocofersolan Drugs 0.000 claims 3
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims 3
150000005827 chlorofluoro hydrocarbons Chemical group 0.000 claims 1
230000001804 emulsifying effect Effects 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
238000002360 preparation method Methods 0.000 description 5
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000000428 dust Substances 0.000 description 4
108091006905 Human Serum Albumin Proteins 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
229940124630 bronchodilator Drugs 0.000 description 3
238000004925 denaturation Methods 0.000 description 3
230000036425 denaturation Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000002502 liposome Substances 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
229920002307 Dextran Polymers 0.000 description 2
102000008100 Human Serum Albumin Human genes 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
206010028980 Neoplasm Diseases 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
229940009456 adriamycin Drugs 0.000 description 2
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
VFPFQHQNJCMNBZ-UHFFFAOYSA-N ethyl gallate Chemical compound CCOC(=O)C1=CC(O)=C(O)C(O)=C1 VFPFQHQNJCMNBZ-UHFFFAOYSA-N 0.000 description 2
238000013265 extended release Methods 0.000 description 2
LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
229960002052 salbutamol Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
230000008685 targeting Effects 0.000 description 2
239000011732 tocopherol Substances 0.000 description 2
231100000167 toxic agent Toxicity 0.000 description 2
239000003440 toxic substance Substances 0.000 description 2
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
DYIOSHGVFJTOAR-JGWLITMVSA-N (2r,3r,4s,5r)-6-sulfanylhexane-1,2,3,4,5-pentol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CS DYIOSHGVFJTOAR-JGWLITMVSA-N 0.000 description 1
RIQXULCAEXVXDY-UHFFFAOYSA-N 2,5-dimethyl-4-(morpholin-4-ylmethyl)phenol Chemical compound C1=C(O)C(C)=CC(CN2CCOCC2)=C1C RIQXULCAEXVXDY-UHFFFAOYSA-N 0.000 description 1
MUFDLGGSOCHQOC-HTKOBJQYSA-N 4-[(1s,2r)-1-hydroxy-2-(propan-2-ylamino)butyl]benzene-1,2-diol;hydrochloride Chemical compound Cl.CC(C)N[C@H](CC)[C@@H](O)C1=CC=C(O)C(O)=C1 MUFDLGGSOCHQOC-HTKOBJQYSA-N 0.000 description 1
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 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
239000004255 Butylated hydroxyanisole Substances 0.000 description 1
239000004322 Butylated hydroxytoluene Substances 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
235000003255 Carthamus tinctorius Nutrition 0.000 description 1
244000020518 Carthamus tinctorius Species 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
239000004262 Ethyl gallate Substances 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000000867 Lipoxygenase Inhibitor Substances 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
235000003434 Sesamum indicum Nutrition 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000004133 Sodium thiosulphate Substances 0.000 description 1
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
108010088160 Staphylococcal Protein A Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
244000247617 Teramnus labialis var. labialis Species 0.000 description 1
BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
FOLJTMYCYXSPFQ-CJKAUBRRSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-(octadecanoyloxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl octadecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCCCCCCCC)O[C@@H]1O[C@@]1(COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@@H](CO)O1 FOLJTMYCYXSPFQ-CJKAUBRRSA-N 0.000 description 1
239000003570 air Substances 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
235000010385 ascorbyl palmitate Nutrition 0.000 description 1
229960002028 atropine sulfate Drugs 0.000 description 1
239000011324 bead Substances 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
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 1
229940043253 butylated hydroxyanisole Drugs 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000010382 chemical cross-linking Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
229960000265 cromoglicic acid Drugs 0.000 description 1
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
229960001305 cysteine hydrochloride Drugs 0.000 description 1
239000000824 cytostatic agent Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
235000010350 erythorbic acid Nutrition 0.000 description 1
235000019277 ethyl gallate Nutrition 0.000 description 1
229940013317 fish oils Drugs 0.000 description 1
235000004515 gallic acid Nutrition 0.000 description 1
229940074391 gallic acid Drugs 0.000 description 1
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229940026239 isoascorbic acid Drugs 0.000 description 1
229940031585 isoetharine hydrochloride Drugs 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
229960002657 orciprenaline Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
235000010388 propyl gallate Nutrition 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010352 sodium erythorbate Nutrition 0.000 description 1
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium erythorbate Chemical compound [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
229960000195 terbutaline Drugs 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 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
229960002675 xylitol Drugs 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1

Landscapes

Medicinal Preparation (AREA)

CA 2036844 1990-02-22 1991-02-21 Aerosol permettant une liberation reglee de microspheres de procaterol Abandoned CA2036844A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US48501390A	1990-02-22	1990-02-22
US485,013		1990-02-22

Publications (1)

Publication Number	Publication Date
CA2036844A1 true CA2036844A1 (fr)	1991-08-23

Family

ID=23926589

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2036844 Abandoned CA2036844A1 (fr)	1990-02-22	1991-02-21	Aerosol permettant une liberation reglee de microspheres de procaterol

Country Status (1)

Country	Link
CA (1)	CA2036844A1 (fr)

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US6433040B1 (en)	1997-09-29	2002-08-13	Inhale Therapeutic Systems, Inc.	Stabilized bioactive preparations and methods of use
US6565885B1 (en)	1997-09-29	2003-05-20	Inhale Therapeutic Systems, Inc.	Methods of spray drying pharmaceutical compositions
US6946117B1 (en)	1997-09-29	2005-09-20	Nektar Therapeutics	Stabilized preparations for use in nebulizers
US7368102B2 (en)	2001-12-19	2008-05-06	Nektar Therapeutics	Pulmonary delivery of aminoglycosides
US7442388B2 (en)	2000-05-10	2008-10-28	Weers Jeffry G	Phospholipid-based powders for drug delivery
US8404217B2 (en)	2000-05-10	2013-03-26	Novartis Ag	Formulation for pulmonary administration of antifungal agents, and associated methods of manufacture and use
US8877162B2 (en)	2000-05-10	2014-11-04	Novartis Ag	Stable metal ion-lipid powdered pharmaceutical compositions for drug delivery
US9554993B2 (en)	1997-09-29	2017-01-31	Novartis Ag	Pulmonary delivery particles comprising an active agent

1991
- 1991-02-21 CA CA 2036844 patent/CA2036844A1/fr not_active Abandoned

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US6565885B1 (en)	1997-09-29	2003-05-20	Inhale Therapeutic Systems, Inc.	Methods of spray drying pharmaceutical compositions
US9554993B2 (en)	1997-09-29	2017-01-31	Novartis Ag	Pulmonary delivery particles comprising an active agent
US6946117B1 (en)	1997-09-29	2005-09-20	Nektar Therapeutics	Stabilized preparations for use in nebulizers
US7205343B2 (en)	1997-09-29	2007-04-17	Dellamary Luis A	Stabilized bioactive preparations and method of use
US7306787B2 (en)	1997-09-29	2007-12-11	Nektar Therapeutics	Engineered particles and methods of use
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US6638495B2 (en)	1997-09-29	2003-10-28	Nektar Therapeutics	Stabilized preparation for use in metered dose inhalers
US8404217B2 (en)	2000-05-10	2013-03-26	Novartis Ag	Formulation for pulmonary administration of antifungal agents, and associated methods of manufacture and use
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Legal Events

Date	Code	Title	Description
1994-08-21	FZDE	Dead

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