CA2654383A1 - Pharmaceutical compositions of ropinirole and methods of use thereof - Google Patents
Pharmaceutical compositions of ropinirole and methods of use thereof Download PDFInfo
- Publication number
- CA2654383A1 CA2654383A1 CA002654383A CA2654383A CA2654383A1 CA 2654383 A1 CA2654383 A1 CA 2654383A1 CA 002654383 A CA002654383 A CA 002654383A CA 2654383 A CA2654383 A CA 2654383A CA 2654383 A1 CA2654383 A1 CA 2654383A1
- Authority
- CA
- Canada
- Prior art keywords
- ropinirole
- gel
- skin
- delivery
- formulation
- 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
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical group CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 title claims abstract description 448
- 229960001879 ropinirole Drugs 0.000 title claims abstract description 422
- 238000000034 method Methods 0.000 title claims description 62
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 415
- 229940079593 drug Drugs 0.000 claims abstract description 97
- 239000002904 solvent Substances 0.000 claims abstract description 49
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 45
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 38
- 239000006172 buffering agent Substances 0.000 claims abstract description 35
- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 30
- 239000003349 gelling agent Substances 0.000 claims abstract description 28
- 238000012377 drug delivery Methods 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 100
- 239000003814 drug Substances 0.000 claims description 86
- 239000012458 free base Substances 0.000 claims description 65
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 63
- 230000004907 flux Effects 0.000 claims description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- 239000002552 dosage form Substances 0.000 claims description 50
- 230000036470 plasma concentration Effects 0.000 claims description 40
- 241000282414 Homo sapiens Species 0.000 claims description 31
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 30
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 21
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 16
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 16
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 16
- 229940001584 sodium metabisulfite Drugs 0.000 claims description 16
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 16
- 229940043348 myristyl alcohol Drugs 0.000 claims description 15
- 239000013543 active substance Substances 0.000 claims description 14
- 230000001225 therapeutic effect Effects 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 12
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 11
- 201000006517 essential tremor Diseases 0.000 claims description 10
- 230000010355 oscillation Effects 0.000 claims description 9
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
- 208000016285 Movement disease Diseases 0.000 claims description 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 7
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 7
- 208000016620 Tourette disease Diseases 0.000 claims description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 7
- 208000021703 chronic tic disease Diseases 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 238000013271 transdermal drug delivery Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 abstract description 25
- -1 ropinirole) Chemical compound 0.000 abstract description 22
- 208000012902 Nervous system disease Diseases 0.000 abstract description 6
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 abstract description 6
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 abstract description 5
- 208000025966 Neurological disease Diseases 0.000 abstract description 3
- 238000009472 formulation Methods 0.000 description 282
- 210000003491 skin Anatomy 0.000 description 152
- 239000000499 gel Substances 0.000 description 102
- 239000000243 solution Substances 0.000 description 55
- 235000006708 antioxidants Nutrition 0.000 description 37
- 238000000338 in vitro Methods 0.000 description 35
- 239000003981 vehicle Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 230000037317 transdermal delivery Effects 0.000 description 30
- 239000003623 enhancer Substances 0.000 description 29
- 230000000694 effects Effects 0.000 description 26
- 238000010521 absorption reaction Methods 0.000 description 22
- 230000001186 cumulative effect Effects 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 230000035515 penetration Effects 0.000 description 20
- 229960004063 propylene glycol Drugs 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 19
- 108020003175 receptors Proteins 0.000 description 19
- 102000005962 receptors Human genes 0.000 description 19
- 210000004027 cell Anatomy 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 12
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 12
- 230000008901 benefit Effects 0.000 description 12
- 238000011161 development Methods 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 11
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- 238000001727 in vivo Methods 0.000 description 10
- 230000033001 locomotion Effects 0.000 description 10
- 230000008520 organization Effects 0.000 description 10
- 239000002953 phosphate buffered saline Substances 0.000 description 10
- 238000005070 sampling Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- 239000010432 diamond Substances 0.000 description 9
- 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 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 210000002615 epidermis Anatomy 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 210000004400 mucous membrane Anatomy 0.000 description 9
- 210000000434 stratum corneum Anatomy 0.000 description 9
- 230000000699 topical effect Effects 0.000 description 9
- 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 8
- 239000004480 active ingredient Substances 0.000 description 8
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 8
- 239000003002 pH adjusting agent Substances 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 229960002349 ropinirole hydrochloride Drugs 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000004888 barrier function Effects 0.000 description 7
- 230000001955 cumulated effect Effects 0.000 description 7
- 210000004207 dermis Anatomy 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000036556 skin irritation Effects 0.000 description 7
- 238000013268 sustained release Methods 0.000 description 7
- 239000012730 sustained-release form Substances 0.000 description 7
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010040880 Skin irritation Diseases 0.000 description 6
- 229920002125 Sokalan® Polymers 0.000 description 6
- 241000282898 Sus scrofa Species 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000006186 oral dosage form Substances 0.000 description 6
- 230000035699 permeability Effects 0.000 description 6
- 235000010388 propyl gallate Nutrition 0.000 description 6
- 239000000473 propyl gallate Substances 0.000 description 6
- 229940075579 propyl gallate Drugs 0.000 description 6
- 229940113775 requip Drugs 0.000 description 6
- 231100000274 skin absorption Toxicity 0.000 description 6
- 230000037384 skin absorption Effects 0.000 description 6
- 231100000475 skin irritation Toxicity 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
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- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 4
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229960002274 atenolol Drugs 0.000 description 4
- 229960001948 caffeine Drugs 0.000 description 4
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 4
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 4
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- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- 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
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- 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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/38—Cellulose; Derivatives thereof
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- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
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- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
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- Epidemiology (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychology (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81725906P | 2006-06-29 | 2006-06-29 | |
| US60/817,259 | 2006-06-29 | ||
| PCT/US2007/014821 WO2008005240A2 (en) | 2006-06-29 | 2007-06-26 | Ropinirole-containing pharmaceutical compositions in the form of a gel, uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2654383A1 true CA2654383A1 (en) | 2008-01-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002654383A Abandoned CA2654383A1 (en) | 2006-06-29 | 2007-06-26 | Pharmaceutical compositions of ropinirole and methods of use thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20080004329A1 (enExample) |
| EP (1) | EP2032125A2 (enExample) |
| JP (1) | JP2009542657A (enExample) |
| KR (1) | KR20090031598A (enExample) |
| CN (1) | CN101478952A (enExample) |
| AR (1) | AR063201A1 (enExample) |
| AU (1) | AU2007269896A1 (enExample) |
| BR (1) | BRPI0713801A2 (enExample) |
| CA (1) | CA2654383A1 (enExample) |
| IL (1) | IL195161A0 (enExample) |
| MX (1) | MX2008015083A (enExample) |
| NO (1) | NO20085158L (enExample) |
| NZ (1) | NZ572481A (enExample) |
| PE (1) | PE20080374A1 (enExample) |
| TW (1) | TW200815045A (enExample) |
| UY (1) | UY30442A1 (enExample) |
| WO (1) | WO2008005240A2 (enExample) |
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| US11400065B2 (en) | 2019-03-01 | 2022-08-02 | Flamel Ireland Limited | Gamma-hydroxybutyrate compositions having improved pharmacokinetics in the fed state |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11839597B2 (en) | 2016-07-22 | 2023-12-12 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
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| US20070212397A1 (en) * | 2005-09-15 | 2007-09-13 | Roth Daniel B | Pharmaceutical delivery device and method for providing ocular treatment |
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| US8623395B2 (en) | 2010-01-29 | 2014-01-07 | Forsight Vision4, Inc. | Implantable therapeutic device |
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| JP5820469B2 (ja) | 2010-04-30 | 2015-11-24 | テイコク ファーマ ユーエスエー インコーポレーテッド | プロピニルアミノインダンの経皮組成物 |
| PT2600812T (pt) | 2010-08-05 | 2021-11-09 | Forsight Vision4 Inc | Aparelho para tratar um olho |
| EP2600876B1 (en) | 2010-08-05 | 2015-04-29 | Forsight Vision4, Inc. | Combined drug delivery methods and apparatus |
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| WO2012068549A2 (en) | 2010-11-19 | 2012-05-24 | Forsight Vision4, Inc. | Therapeutic agent formulations for implanted devices |
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| BR112015000329A2 (pt) | 2012-07-12 | 2017-06-27 | Ferring Bv | formulações de diclofenac |
| JP6050896B2 (ja) | 2012-11-02 | 2016-12-21 | テイコク ファーマ ユーエスエー インコーポレーテッド | プロピニルアミノインダン経皮組成物 |
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- 2007-06-26 KR KR1020097001878A patent/KR20090031598A/ko not_active Withdrawn
- 2007-06-26 BR BRPI0713801-6A patent/BRPI0713801A2/pt not_active IP Right Cessation
- 2007-06-26 JP JP2009518225A patent/JP2009542657A/ja not_active Withdrawn
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- 2007-06-26 WO PCT/US2007/014821 patent/WO2008005240A2/en not_active Ceased
- 2007-06-26 PE PE2007000821A patent/PE20080374A1/es not_active Application Discontinuation
- 2007-06-26 AU AU2007269896A patent/AU2007269896A1/en not_active Abandoned
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- 2007-06-26 CN CNA2007800229856A patent/CN101478952A/zh active Pending
- 2007-06-26 MX MX2008015083A patent/MX2008015083A/es not_active Application Discontinuation
- 2007-06-27 UY UY30442A patent/UY30442A1/es not_active Application Discontinuation
- 2007-06-28 AR ARP070102901A patent/AR063201A1/es unknown
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2008
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Also Published As
| Publication number | Publication date |
|---|---|
| NO20085158L (no) | 2009-01-15 |
| BRPI0713801A2 (pt) | 2012-11-06 |
| TW200815045A (en) | 2008-04-01 |
| WO2008005240A2 (en) | 2008-01-10 |
| WO2008005240A3 (en) | 2008-05-08 |
| US20080004329A1 (en) | 2008-01-03 |
| EP2032125A2 (en) | 2009-03-11 |
| MX2008015083A (es) | 2008-12-10 |
| NZ572481A (en) | 2011-03-31 |
| IL195161A0 (en) | 2009-08-03 |
| AU2007269896A1 (en) | 2008-01-10 |
| JP2009542657A (ja) | 2009-12-03 |
| UY30442A1 (es) | 2008-01-31 |
| PE20080374A1 (es) | 2008-06-11 |
| AR063201A1 (es) | 2009-01-14 |
| KR20090031598A (ko) | 2009-03-26 |
| CN101478952A (zh) | 2009-07-08 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |