CA2515146A1 - Aerosol formulations and aerosol delivery of buspirone, buprenorphine, triazolam, cyclobenzaprine and zolpidem - Google Patents
Aerosol formulations and aerosol delivery of buspirone, buprenorphine, triazolam, cyclobenzaprine and zolpidem Download PDFInfo
- Publication number
- CA2515146A1 CA2515146A1 CA002515146A CA2515146A CA2515146A1 CA 2515146 A1 CA2515146 A1 CA 2515146A1 CA 002515146 A CA002515146 A CA 002515146A CA 2515146 A CA2515146 A CA 2515146A CA 2515146 A1 CA2515146 A1 CA 2515146A1
- Authority
- CA
- Canada
- Prior art keywords
- aerosol
- active ingredient
- formulation
- liquid
- thermally stable
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract 26
- 238000009472 formulation Methods 0.000 title claims abstract 25
- 239000000443 aerosol Substances 0.000 title claims abstract 24
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 title claims abstract 8
- 229960001736 buprenorphine Drugs 0.000 title claims abstract 8
- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 title claims abstract 8
- 229960002495 buspirone Drugs 0.000 title claims abstract 8
- JURKNVYFZMSNLP-UHFFFAOYSA-N cyclobenzaprine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 JURKNVYFZMSNLP-UHFFFAOYSA-N 0.000 title claims abstract 8
- 229960003572 cyclobenzaprine Drugs 0.000 title claims abstract 8
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 title claims abstract 8
- 229960003386 triazolam Drugs 0.000 title claims abstract 8
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 title claims abstract 8
- 229960001475 zolpidem Drugs 0.000 title claims abstract 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract 24
- 239000004480 active ingredient Substances 0.000 claims abstract 21
- 239000008263 liquid aerosol Substances 0.000 claims abstract 20
- 239000003960 organic solvent Substances 0.000 claims abstract 8
- 239000012669 liquid formulation Substances 0.000 claims abstract 5
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- 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 claims 8
- 208000007934 ACTH-independent macronodular adrenal hyperplasia Diseases 0.000 claims 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 8
- 239000002245 particle Substances 0.000 claims 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 235000011187 glycerol Nutrition 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 3
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000000600 sorbitol Substances 0.000 claims 2
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical class CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 1
- 229930195725 Mannitol Chemical class 0.000 claims 1
- 239000002202 Polyethylene glycol Chemical class 0.000 claims 1
- 239000004372 Polyvinyl alcohol Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000001913 cellulose Chemical class 0.000 claims 1
- 229920002678 cellulose Chemical class 0.000 claims 1
- 229940097362 cyclodextrins Drugs 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical class CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 235000013355 food flavoring agent Nutrition 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229940051250 hexylene glycol Drugs 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Chemical class 0.000 claims 1
- 229920003088 hydroxypropyl methyl cellulose Chemical class 0.000 claims 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical class OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 1
- 239000000594 mannitol Chemical class 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Chemical class 0.000 claims 1
- 229920001451 polypropylene glycol Chemical class 0.000 claims 1
- 229920002451 polyvinyl alcohol Chemical class 0.000 claims 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class 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 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Abstract
A liquid aerosol formulation comprising at least one thermally stable active ingredient selected from the group consisting of buspirone, buprenorphine, triazolam, cyclobenzaprine, zolpidem, pharmaceutically acceptable salts and esters thereof and derivatives thereof. The liquid formulation can include an organic solvent such as propylene glycol and one or more optional excipients.
The active ingredient can be present in an amount of 0.01 to 5 wt. % and the formulation can be heated to provide a vapor which forms an aerosol having a mass median acrodynamic diameter of less than 3 um.
The active ingredient can be present in an amount of 0.01 to 5 wt. % and the formulation can be heated to provide a vapor which forms an aerosol having a mass median acrodynamic diameter of less than 3 um.
Claims (30)
1. A liquid aerosol formulation comprising at least one thermally stable active ingredient selected from the group consisting of buspirone, buprenorphine, triazolam, cyclobenzaprine, zolpidem, pharmaceutically acceptable salts and esters thereof and derivatives thereof.
2. The liquid aerosol formulation of claim 1, further comprising an organic solvent.
3. The liquid aerosol formulation of claim 2, wherein the organic solvent is a short chain (C1 -C6) alcohol.
4. The aerosol formulation of claim 3, wherein the short chain (C1-C6) alcohols are selected from the group consisting of glycerin, ethylene glycol, diethylene glycol, propylene glycol, n-propyl alcohol, isopropyl alcohol, butanol, ethanol, sorbitol, dipropylene glycol, tripropylene glycol, and hexylene glycol.
5. The liquid aerosol formulation of claim 2, further comprising at least one pharmaceutically acceptable excipient.
6. The liquid aerosol formulation of claim 5, wherein the pharmaceutically acceptable excipient is selected from the group consisting of antioxidants, stabilizing agents, flavoring agents, solubilizers, cosolvents, preservatives and combinations thereof.
7. The liquid aerosol formulation of claim 6, wherein the cosolvent is selected from the group consisting of ethanol, water, glycerol and diethyl ether.
8. The liquid aerosol formulation of claim 6, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, butanediols and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, and mixtures thereof.
9. The liquid aerosol formulation of claim 1, wherein the formulation contains 0.01 to 5% by weight of the thermally stable active ingredient.
10. The liquid aerosol formulation of claim 2, wherein the thermally stable active ingredient comprises buspirone and the organic solvent is propylene glycol.
11. The liquid aerosol formulation of claim 2, wherein the thermally stable active ingredient comprises buprenorphine and the organic solvent is propylene glycol.
12. The liquid aerosol formulation of claim 2, wherein the thermally stable active ingredient comprises triazolam and the organic solvent is propylene glycol.
13. The liquid aerosol formulation of claim 2, wherein the thermally stable active ingredient comprises cyclobenzaprine and the organic solvent is propylene glycol.
14. The aerosol formulation of claim 2, wherein the thermally stable active ingredient comprises zolpidem and the organic solvent is propylene glycol.
15. A method of generating an aerosol comprising supplying a liquid aerosol formulation to a flow passage, heating the liquid aerosol formulation in the flow passage so as to volatilize a liquid component thereof and form a vapor which exits from an outlet of the flow passage, and contacting the vapor with a gaseous medium so as to form an aerosol, wherein the liquid aerosol formulation includes at least one thermally stable active ingredient selected from the group consisting of buspirone, buprenorphine, triazolam, cyclobenzaprine, zolpidem, pharmaceutically acceptable salts and esters thereof.
16. The method of claim 15, wherein the gaseous medium comprises air and the aerosol comprises particles of the propylene glycol having an MMAD of less than 3 µm.
17. The method of Claim 15, wherein the liquid aerosol formulation further includes at least one thermally stable active ingredient and the aerosol comprises particles of the thermally stable active ingredient having an MMAD of less than 3 µm.
18. The method of Claim 17, wherein the thermally stable active ingredient comprises buspirone and the aerosol comprises buspirone particles having an MMAD
of less than 3 µm.
of less than 3 µm.
19. The method of claim 17, wherein the thermally stable active ingredient comprises buprenorphine and the aerosol comprises buprenorphine particles having an MMAD of less than 3 µm.
20. The method of claim 17, wherein the thermally stable active ingredient comprises triazolam and the aerosol comprises triazolam particles having an MMAD
of less than 3 µm.
of less than 3 µm.
21. The method of claim 17, wherein the thermally stable active ingredient comprises cyclobenzaprine and the aerosol comprises cyclobenzaprine particles having an MMAD of less than 3 µm.
22. The method of claim 17, wherein the thermally stable active ingredient comprises zolpidem and the aerosol comprises zolpidem particles having an MMAD
of less than 3 µm.
of less than 3 µm.
23. The method of Claim 15, wherein the flow passage is a capillary sized flow passage and the aerosol is formed in a mouthpiece of a handheld inhaler.
24. The method of Claim 15, wherein the liquid aerosol formulation contains at least one thermally stable active ingredient and the aerosol includes particles of the thermally stable active ingredient having an MMAD of 0.1 to 2.5 µm.
25. The method of Claim 15, wherein the flow passage is heated by a resistance heater located in a handheld inhaler, the inhaler including a power supply and control electronics which controls supply of electrical power to the heater as a function of a resistance target in a range of 0.5 to 1 ohm.
26. An aerosol generator comprising:
a flow passage adapted to receive a liquid aerosol generating formulation from a liquid supply, the liquid aerosol formulation comprising at least one thermally stable active ingredient selected from the group consisting of buspirone, buprenorphine, triazolam, cyclobenzaprine, zolpidem, pharmaceutically acceptable salts and esters thereof and derivatives thereof;
a heater operable to heat the liquid formulation in at least a portion of the flow passage sufficiently to vaporize the liquid formulation and generate an aerosol containing the active ingredient.
a flow passage adapted to receive a liquid aerosol generating formulation from a liquid supply, the liquid aerosol formulation comprising at least one thermally stable active ingredient selected from the group consisting of buspirone, buprenorphine, triazolam, cyclobenzaprine, zolpidem, pharmaceutically acceptable salts and esters thereof and derivatives thereof;
a heater operable to heat the liquid formulation in at least a portion of the flow passage sufficiently to vaporize the liquid formulation and generate an aerosol containing the active ingredient.
27. The aerosol generator of Claim 26, wherein the aerosol generator comprises a hand-held inhaler having a mouthpiece, the flow passage comprising a capillary sized flow passage having an outlet in fluid communication with an interior of the mouthpiece.
28. The aerosol generator of Claim 26, wherein the heater is a resistance heater comprising a section of a metal capillary tube and the flow passage comprises the interior of the metal capillary tube.
29. The aerosol generator of Claim 26, wherein the aerosol generator comprises a hand-held inhaler having a power supply and control electronics which controls supply of electrical power to the heater as a function of a control parameter selected to achieve boiling of the liquid formulation in the flow passage.
30. The aerosol generator of Claim 26, wherein the liquid supply comprises a reservoir containing the liquid formulation under a pressure of no greater than about atmospheric pressure.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44462203P | 2003-02-04 | 2003-02-04 | |
| US60/444,622 | 2003-02-04 | ||
| PCT/US2003/039819 WO2004071491A1 (en) | 2003-02-04 | 2003-12-15 | Aerosol formulations and aerosol delivery of buspirone, buprenorphine, triazolam, cyclobenzaprine and zolpidem |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2515146A1 true CA2515146A1 (en) | 2004-08-26 |
| CA2515146C CA2515146C (en) | 2011-12-06 |
Family
ID=32869294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2515146A Expired - Lifetime CA2515146C (en) | 2003-02-04 | 2003-12-15 | Aerosol formulations and aerosol delivery of buspirone, buprenorphine, triazolam, cyclobenzaprine and zolpidem |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7501113B2 (en) |
| EP (1) | EP1596824A4 (en) |
| JP (1) | JP2006516963A (en) |
| AU (1) | AU2003297087B2 (en) |
| CA (1) | CA2515146C (en) |
| WO (1) | WO2004071491A1 (en) |
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| US7683029B2 (en) * | 2003-05-07 | 2010-03-23 | Philip Morris Usa Inc. | Liquid aerosol formulations containing insulin and aerosol generating devices and methods for generating aerosolized insulin |
| WO2004112799A1 (en) * | 2003-06-13 | 2004-12-29 | Chrysalis Technologies Incorporated | Methods and apparatus for producing nanoscale particles |
| WO2005037949A2 (en) * | 2003-10-07 | 2005-04-28 | Chrysalis Technologies Incorporated | Aerosol formulations of butalbital, lorazepam, ipratropium, baclofen, morphine and scopolamine |
| US20060102175A1 (en) * | 2004-11-18 | 2006-05-18 | Nelson Stephen G | Inhaler |
| US7186958B1 (en) * | 2005-09-01 | 2007-03-06 | Zhao Wei, Llc | Inhaler |
| US8852638B2 (en) | 2005-09-30 | 2014-10-07 | Durect Corporation | Sustained release small molecule drug formulation |
| GB0606124D0 (en) * | 2006-03-28 | 2006-05-03 | Reckitt Benckiser Healthcare | Buprenorphine derivatives and uses thereof |
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| GB0620661D0 (en) * | 2006-10-18 | 2006-11-29 | Pharmasol Ltd | Novel compounds |
| GB2461681A (en) * | 2008-04-17 | 2010-01-13 | Pharmasol Ltd | Buprenorphine liquid spray formulation with solvent and antioxidant |
| NZ581862A (en) | 2007-05-25 | 2012-06-29 | Tolmar Therapeutics Inc | Injectable subcutaneous formulation comprising risperidone capable of forming a solid, microporous implant in a patient |
| US7955782B2 (en) * | 2008-09-22 | 2011-06-07 | Honeywell International Inc. | Bottom antireflective coatings exhibiting enhanced wet strip rates, bottom antireflective coating compositions for forming bottom antireflective coatings, and methods for fabricating the same |
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| GB2481017B (en) * | 2010-06-08 | 2015-01-07 | Rb Pharmaceuticals Ltd | Microparticle buprenorphine suspension |
| ITMI20110558A1 (en) * | 2011-04-06 | 2012-10-07 | Campiglio Consulting Srl | PHARMACEUTICAL COMPOSITION CONTAINING CYCLOBENZAPRINE SUITABLE FOR ENDONASAL ADMINISTRATION |
| AR092330A1 (en) * | 2012-06-15 | 2015-04-15 | Tonix Pharmaceuticals Inc | COMPOSITIONS, METHODS OF TRANSMUCOUS ABSORPTION AND TREATMENT METHOD |
| DK3043777T3 (en) | 2013-09-10 | 2020-07-20 | Fresh Cut Dev Llc | SUBLINGUAL BUPRENORPHINSPRAY |
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| US9839611B2 (en) | 2013-09-10 | 2017-12-12 | Insys Development Company, Inc. | Sublingual buprenorphine spray |
| GB201404139D0 (en) | 2014-03-10 | 2014-04-23 | Rb Pharmaceuticals Ltd | Sustained release buprenorphine solution formulations |
| US10617686B2 (en) | 2014-07-08 | 2020-04-14 | Hikma Pharmaceuticals Usa Inc. | Liquid naloxone spray |
| CA2954370A1 (en) | 2014-07-08 | 2016-01-14 | Insys Pharma, Inc. | Sublingual naloxone spray |
| US10722510B2 (en) | 2014-07-08 | 2020-07-28 | Hikma Pharmaceuticals Usa Inc. | Liquid naloxone spray |
| DK3215223T3 (en) | 2014-11-07 | 2020-08-03 | Indivior Uk Ltd | BUPRENORPHIN DOSAGE SCHEMES |
| US10646484B2 (en) | 2017-06-16 | 2020-05-12 | Indivior Uk Limited | Methods to treat opioid use disorder |
| US11209411B2 (en) * | 2018-01-12 | 2021-12-28 | Purdue Research Foundation | Methods for analyzing stability of an active pharmaceutical ingredient |
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-
2003
- 2003-12-15 JP JP2004568324A patent/JP2006516963A/en active Pending
- 2003-12-15 EP EP03815912A patent/EP1596824A4/en not_active Withdrawn
- 2003-12-15 AU AU2003297087A patent/AU2003297087B2/en not_active Expired
- 2003-12-15 WO PCT/US2003/039819 patent/WO2004071491A1/en active Application Filing
- 2003-12-15 US US10/734,150 patent/US7501113B2/en not_active Expired - Fee Related
- 2003-12-15 CA CA2515146A patent/CA2515146C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1596824A4 (en) | 2011-11-23 |
| CA2515146C (en) | 2011-12-06 |
| EP1596824A1 (en) | 2005-11-23 |
| AU2003297087B2 (en) | 2009-06-11 |
| US7501113B2 (en) | 2009-03-10 |
| WO2004071491A1 (en) | 2004-08-26 |
| JP2006516963A (en) | 2006-07-13 |
| AU2003297087A1 (en) | 2004-09-06 |
| US20040151670A1 (en) | 2004-08-05 |
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