AU2014296032A1 - Aerosol tyrosine kinase inhibitor compounds and uses thereof - Google Patents
Aerosol tyrosine kinase inhibitor compounds and uses thereof Download PDFInfo
- Publication number
- AU2014296032A1 AU2014296032A1 AU2014296032A AU2014296032A AU2014296032A1 AU 2014296032 A1 AU2014296032 A1 AU 2014296032A1 AU 2014296032 A AU2014296032 A AU 2014296032A AU 2014296032 A AU2014296032 A AU 2014296032A AU 2014296032 A1 AU2014296032 A1 AU 2014296032A1
- Authority
- AU
- Australia
- Prior art keywords
- salt
- imatinib
- tyrosine kinase
- kinase inhibitor
- phenylaminopyrimidine derivative
- Prior art date
- 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
Links
- -1 tyrosine kinase inhibitor compounds Chemical class 0.000 title claims abstract description 73
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title claims description 504
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title claims description 504
- 239000000443 aerosol Substances 0.000 title abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 1542
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims abstract description 526
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims abstract description 526
- 229960002411 imatinib Drugs 0.000 claims abstract description 526
- 210000004072 lung Anatomy 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 238000011282 treatment Methods 0.000 claims abstract description 9
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical class N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 claims description 510
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims description 479
- 239000007864 aqueous solution Substances 0.000 claims description 295
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 229
- 239000000243 solution Substances 0.000 claims description 195
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 135
- 239000011780 sodium chloride Substances 0.000 claims description 115
- 239000006199 nebulizer Substances 0.000 claims description 99
- 239000008363 phosphate buffer Substances 0.000 claims description 92
- 239000007979 citrate buffer Substances 0.000 claims description 89
- 241000124008 Mammalia Species 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 65
- 239000007788 liquid Substances 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 48
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 17
- 235000003599 food sweetener Nutrition 0.000 claims description 11
- 239000003765 sweetening agent Substances 0.000 claims description 11
- 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 claims description 9
- 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 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 239000008101 lactose Substances 0.000 claims description 9
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 9
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
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- 239000002904 solvent Substances 0.000 claims description 7
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- 239000000080 wetting agent Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
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- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 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 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
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- 238000000634 powder X-ray diffraction Methods 0.000 claims 20
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 229910001622 calcium bromide Inorganic materials 0.000 claims 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000012384 transportation and delivery Methods 0.000 abstract description 54
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- 208000035473 Communicable disease Diseases 0.000 abstract description 2
- 230000003176 fibrotic effect Effects 0.000 abstract description 2
- 230000002265 prevention Effects 0.000 abstract description 2
- 230000003612 virological effect Effects 0.000 abstract description 2
- 238000012387 aerosolization Methods 0.000 abstract 1
- 230000000711 cancerogenic effect Effects 0.000 abstract 1
- 231100000315 carcinogenic Toxicity 0.000 abstract 1
- 230000002792 vascular Effects 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 description 116
- 230000002685 pulmonary effect Effects 0.000 description 51
- 150000004926 Imatinib derivatives Chemical class 0.000 description 35
- 210000001519 tissue Anatomy 0.000 description 23
- 230000003139 buffering effect Effects 0.000 description 22
- 239000006068 taste-masking agent Substances 0.000 description 17
- 239000002246 antineoplastic agent Substances 0.000 description 16
- 230000003510 anti-fibrotic effect Effects 0.000 description 15
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 14
- 230000001093 anti-cancer Effects 0.000 description 14
- 229940121363 anti-inflammatory agent Drugs 0.000 description 14
- 239000002260 anti-inflammatory agent Substances 0.000 description 14
- 229960005475 antiinfective agent Drugs 0.000 description 14
- 239000004599 antimicrobial Substances 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 10
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- 239000003172 expectorant agent Substances 0.000 description 9
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- 235000019204 saccharin Nutrition 0.000 description 9
- 229940081974 saccharin Drugs 0.000 description 9
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- 208000029523 Interstitial Lung disease Diseases 0.000 description 8
- 229960001375 lactose Drugs 0.000 description 8
- 108010011485 Aspartame Proteins 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 7
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- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 7
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- 239000008121 dextrose Substances 0.000 description 7
- 229960001031 glucose Drugs 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- 229960004793 sucrose Drugs 0.000 description 7
- 229940043355 kinase inhibitor Drugs 0.000 description 6
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 6
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 5
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 4
- 101100024019 Mus musculus Mosmo gene Proteins 0.000 description 3
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
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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
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- 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
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2018222878A AU2018222878A1 (en) | 2013-07-31 | 2018-08-27 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
| AU2020201933A AU2020201933A1 (en) | 2013-07-31 | 2020-03-18 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
| AU2022202349A AU2022202349A1 (en) | 2013-07-31 | 2022-04-07 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
| AU2024203957A AU2024203957A1 (en) | 2013-07-31 | 2024-06-11 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361860721P | 2013-07-31 | 2013-07-31 | |
| US61/860,721 | 2013-07-31 | ||
| US201461948461P | 2014-03-05 | 2014-03-05 | |
| US61/948,461 | 2014-03-05 | ||
| PCT/US2014/049294 WO2015017728A1 (en) | 2013-07-31 | 2014-07-31 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018222878A Division AU2018222878A1 (en) | 2013-07-31 | 2018-08-27 | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2014296032A1 true AU2014296032A1 (en) | 2016-03-17 |
Family
ID=52432447
Family Applications (5)
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