CA2215716C - Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes - Google Patents

Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes Download PDF

Info

Publication number: CA2215716C
Authority: CA; Canada
Prior art keywords: liposome; ciprofloxacin; encapsulated; aerosol; particles
Prior art date: 1997-09-17
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.): Expired - Fee Related

Application number

CA 2215716

Other languages

English (en)

Inventor

Jonathan P.H. Wong

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.)

Minister of National Defence of Canada

Original Assignee

Minister of National Defence of Canada

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.)

1997-09-17

Filing date

1997-09-17

Publication date

1999-12-07

1997-09-17 Application filed by Minister of National Defence of Canada filed Critical Minister of National Defence of Canada

1997-09-17 Priority to CA 2215716 priority Critical patent/CA2215716C/fr

1999-12-07 Application granted granted Critical

1999-12-07 Publication of CA2215716C publication Critical patent/CA2215716C/fr

2017-09-17 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000443 aerosol Substances 0.000 title claims abstract description 60
229940124307 fluoroquinolone Drugs 0.000 title claims abstract description 15
208000015181 infectious disease Diseases 0.000 claims abstract description 25
206010057190 Respiratory tract infections Diseases 0.000 claims abstract description 12
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 116
229960003405 ciprofloxacin Drugs 0.000 claims description 58
239000002245 particle Substances 0.000 claims description 33
239000006199 nebulizer Substances 0.000 claims description 18
241000589602 Francisella tularensis Species 0.000 claims description 17
238000000034 method Methods 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 10
229940118764 francisella tularensis Drugs 0.000 claims description 8
QKDHBVNJCZBTMR-LLVKDONJSA-N (R)-temafloxacin Chemical compound C1CN[C@H](C)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F QKDHBVNJCZBTMR-LLVKDONJSA-N 0.000 claims description 3
RZLHGQLYNZQZQQ-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxo-7-pyrrol-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1C=CC=C1 RZLHGQLYNZQZQQ-UHFFFAOYSA-N 0.000 claims description 3
XBHBWNFJWIASRO-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 XBHBWNFJWIASRO-UHFFFAOYSA-N 0.000 claims description 3
WUWFMDMBOJLQIV-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(N)CCN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F WUWFMDMBOJLQIV-UHFFFAOYSA-N 0.000 claims description 3
GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 3
RUXPNBWPIRDVTH-UHFFFAOYSA-N Amifloxacin Chemical compound C1=C2N(NC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 RUXPNBWPIRDVTH-UHFFFAOYSA-N 0.000 claims description 3
SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 claims description 3
QMLVECGLEOSESV-RYUDHWBXSA-N Danofloxacin Chemical compound C([C@@H]1C[C@H]2CN1C)N2C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1CC1 QMLVECGLEOSESV-RYUDHWBXSA-N 0.000 claims description 3
NJCJBUHJQLFDSW-UHFFFAOYSA-N Rufloxacin Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 NJCJBUHJQLFDSW-UHFFFAOYSA-N 0.000 claims description 3
229950009484 amifloxacin Drugs 0.000 claims description 3
229960004621 cinoxacin Drugs 0.000 claims description 3
VDUWPHTZYNWKRN-UHFFFAOYSA-N cinoxacin Chemical compound C1=C2N(CC)N=C(C(O)=O)C(=O)C2=CC2=C1OCO2 VDUWPHTZYNWKRN-UHFFFAOYSA-N 0.000 claims description 3
229960004385 danofloxacin Drugs 0.000 claims description 3
229950001733 difloxacin Drugs 0.000 claims description 3
NOCJXYPHIIZEHN-UHFFFAOYSA-N difloxacin Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1 NOCJXYPHIIZEHN-UHFFFAOYSA-N 0.000 claims description 3
229960002549 enoxacin Drugs 0.000 claims description 3
IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 claims description 3
229960000740 enrofloxacin Drugs 0.000 claims description 3
229960003306 fleroxacin Drugs 0.000 claims description 3
XBJBPGROQZJDOJ-UHFFFAOYSA-N fleroxacin Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CCF)C2=C1F XBJBPGROQZJDOJ-UHFFFAOYSA-N 0.000 claims description 3
229950003514 irloxacin Drugs 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
229960002422 lomefloxacin Drugs 0.000 claims description 3
ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 claims description 3
229950007835 miloxacin Drugs 0.000 claims description 3
ABQYZRZVRIPTPI-UHFFFAOYSA-N miloxacin Chemical compound C1=C2N(OC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 ABQYZRZVRIPTPI-UHFFFAOYSA-N 0.000 claims description 3
229960001180 norfloxacin Drugs 0.000 claims description 3
OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 claims description 3
229960001699 ofloxacin Drugs 0.000 claims description 3
229960004236 pefloxacin Drugs 0.000 claims description 3
FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 claims description 3
229960003889 rosoxacin Drugs 0.000 claims description 3
XBPZXDSZHPDXQU-UHFFFAOYSA-N rosoxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC=C1C1=CC=NC=C1 XBPZXDSZHPDXQU-UHFFFAOYSA-N 0.000 claims description 3
229960004062 rufloxacin Drugs 0.000 claims description 3
229950007734 sarafloxacin Drugs 0.000 claims description 3
229960004954 sparfloxacin Drugs 0.000 claims description 3
DZZWHBIBMUVIIW-DTORHVGOSA-N sparfloxacin Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=C(F)C(N)=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DZZWHBIBMUVIIW-DTORHVGOSA-N 0.000 claims description 3
229960004576 temafloxacin Drugs 0.000 claims description 3
229950008187 tosufloxacin Drugs 0.000 claims description 3
229940071648 metered dose inhaler Drugs 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 abstract description 17
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238000011282 treatment Methods 0.000 abstract description 11
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230000008685 targeting Effects 0.000 abstract 1
241000699670 Mus sp. Species 0.000 description 36
BLUGYPPOFIHFJS-UUFHNPECSA-N (2s)-n-[(2s)-1-[[(3r,4s,5s)-3-methoxy-1-[(2s)-2-[(1r,2r)-1-methoxy-2-methyl-3-oxo-3-[[(1s)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamid Chemical compound CN[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 BLUGYPPOFIHFJS-UUFHNPECSA-N 0.000 description 10
208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 description 10
210000004072 lung Anatomy 0.000 description 7
210000000056 organ Anatomy 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
238000000151 deposition Methods 0.000 description 6
239000002502 liposome Substances 0.000 description 6
239000002953 phosphate buffered saline Substances 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
230000008021 deposition Effects 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
230000000241 respiratory effect Effects 0.000 description 5
238000005070 sampling Methods 0.000 description 5
210000000952 spleen Anatomy 0.000 description 5
231100000111 LD50 Toxicity 0.000 description 4
208000034784 Tularaemia Diseases 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
230000001965 increasing effect Effects 0.000 description 4
229920000379 polypropylene carbonate Polymers 0.000 description 4
238000002300 pressure perturbation calorimetry Methods 0.000 description 4
230000002265 prevention Effects 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
239000008272 agar Substances 0.000 description 3
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
235000018417 cysteine Nutrition 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
108020004414 DNA Proteins 0.000 description 2
102000053602 DNA Human genes 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
238000009395 breeding Methods 0.000 description 2
230000001488 breeding effect Effects 0.000 description 2
206010006451 bronchitis Diseases 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
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 2
238000012377 drug delivery Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
229940127554 medical product Drugs 0.000 description 2
210000003097 mucus Anatomy 0.000 description 2
244000052769 pathogen Species 0.000 description 2
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 2
230000003389 potentiating effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
208000000884 Airway Obstruction Diseases 0.000 description 1
108020000946 Bacterial DNA Proteins 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
238000009631 Broth culture Methods 0.000 description 1
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206010014561 Emphysema Diseases 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
208000032376 Lung infection Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000545499 Mycobacterium avium-intracellulare Species 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
241000588653 Neisseria Species 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
238000012387 aerosolization Methods 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000004044 bronchoconstricting agent Substances 0.000 description 1
230000003435 bronchoconstrictive effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
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231100000517 death Toxicity 0.000 description 1
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238000003745 diagnosis Methods 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
230000008029 eradication Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003172 expectorant agent Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000000510 mucolytic effect Effects 0.000 description 1
229940066491 mucolytics Drugs 0.000 description 1
238000001503 one-tailed test Methods 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
244000000070 pulmonary pathogen Species 0.000 description 1
150000007660 quinolones Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229960005486 vaccine 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
- 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
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Otolaryngology (AREA)
Pulmonology (AREA)
Dispersion Chemistry (AREA)
Medicinal Preparation (AREA)

CA 2215716 1997-09-17 1997-09-17 Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes Expired - Fee Related CA2215716C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2215716 CA2215716C (fr)	1997-09-17	1997-09-17	Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2215716 CA2215716C (fr)	1997-09-17	1997-09-17	Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes

Publications (1)

Publication Number	Publication Date
CA2215716C true CA2215716C (fr)	1999-12-07

Family

ID=29275020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2215716 Expired - Fee Related CA2215716C (fr)	1997-09-17	1997-09-17	Administration, grace a un aerosol, de fluoroquinolone encapsulee dans des liposomes

Country Status (1)

Country	Link
CA (1)	CA2215716C (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004110493A3 (fr) *	2003-05-30	2005-09-15	Alza Corp	Methode d'administration pulmonaire d'un agent
US7300667B1 (en)	1999-05-27	2007-11-27	Euro-Celtique, S.A.	Preparations for the application of anti-inflammatory, especially antiseptic agents and/or agents promoting the healing of wounds, to the lower respiratory tract
US7364749B1 (en)	1999-05-27	2008-04-29	Euro-Celtique, S.A.	Preparations for the application of anti-infective and/or anti-inflammatory agents
WO2008063341A3 (fr) *	2006-10-24	2008-10-16	Aradigm Corp	Préparations inhalées, à double action permettant d'obtenir un profil de libération immédiate et prolongée
WO2009044141A1 (fr) *	2007-10-05	2009-04-09	E-Therapeutics Plc	Compositions comprenant de la cétirizine et un non-agoniste du bêta-2-adrénorécepteur, un agoniste du bêta-2-adrénorécepteur ou un anti-inflammatoire et leur utilisation pour le traitement de troubles respiratoires
US8071127B2 (en)	2006-10-24	2011-12-06	Aradigm Corporation	Dual action, inhaled formulations providing both an immediate and sustained release profile
US8119156B2 (en)	2006-10-24	2012-02-21	Aradigm Corporation	Dual action, inhaled formulations providing both an immediate and sustained release profile
WO2015156904A1 (fr)	2014-04-08	2015-10-15	Aradigm Corporation	Liposomes formant des nanocristaux de médicament suite à congélation-décongélation
CN105496962A (zh) *	2016-02-26	2016-04-20	临沂大学	一种盐酸沙拉沙星中药提取物脂质体及其制备方法
US9402845B2 (en)	2005-12-08	2016-08-02	Insmed Incorporated	Lipid-based compositions of antiinfectives for treating pulmonary infections and methods of use thereof
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Date	Code	Title	Description
1999-04-07	EEER	Examination request
2017-10-30	MKLA	Lapsed	Effective date: 20170918

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