NZ572481A - Pharmaceutical compositions of ropinirole and methods of use thereof - Google Patents
Pharmaceutical compositions of ropinirole and methods of use thereofInfo
- Publication number
- NZ572481A NZ572481A NZ572481A NZ57248107A NZ572481A NZ 572481 A NZ572481 A NZ 572481A NZ 572481 A NZ572481 A NZ 572481A NZ 57248107 A NZ57248107 A NZ 57248107A NZ 572481 A NZ572481 A NZ 572481A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ropinirole
- skin
- gel composition
- gel
- delivery
- Prior art date
Links
- UHSKFQJFRQCDBE-UHFFFAOYSA-N ropinirole Chemical group CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 UHSKFQJFRQCDBE-UHFFFAOYSA-N 0.000 title claims abstract description 452
- 229960001879 ropinirole Drugs 0.000 title claims abstract description 428
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title description 54
- 239000000203 mixture Substances 0.000 claims abstract description 446
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 98
- 229940079593 drug Drugs 0.000 claims abstract description 95
- 239000003814 drug Substances 0.000 claims abstract description 86
- 239000002552 dosage form Substances 0.000 claims abstract description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 239000006172 buffering agent Substances 0.000 claims abstract description 34
- 239000003961 penetration enhancing agent Substances 0.000 claims abstract description 34
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229940043348 myristyl alcohol Drugs 0.000 claims abstract description 23
- 238000012377 drug delivery Methods 0.000 claims abstract description 22
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 18
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims abstract description 17
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 12
- 201000006517 essential tremor Diseases 0.000 claims abstract description 11
- 208000016285 Movement disease Diseases 0.000 claims abstract description 10
- 208000005793 Restless legs syndrome Diseases 0.000 claims abstract description 8
- 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 8
- 208000016620 Tourette disease Diseases 0.000 claims abstract description 8
- 208000021703 chronic tic disease Diseases 0.000 claims abstract description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 66
- 239000012458 free base Substances 0.000 claims description 61
- 230000004907 flux Effects 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 48
- 239000003963 antioxidant agent Substances 0.000 claims description 46
- 230000036470 plasma concentration Effects 0.000 claims description 42
- 230000003078 antioxidant effect Effects 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 30
- 239000003349 gelling agent Substances 0.000 claims description 28
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 18
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 18
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 18
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 230000010355 oscillation Effects 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000013271 transdermal drug delivery Methods 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 208000013403 hyperactivity Diseases 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- 230000006735 deficit Effects 0.000 claims 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 abstract description 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 abstract description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 abstract description 7
- 238000009472 formulation Methods 0.000 description 281
- 210000003491 skin Anatomy 0.000 description 153
- 239000000499 gel Substances 0.000 description 114
- 239000000243 solution Substances 0.000 description 54
- 235000006708 antioxidants Nutrition 0.000 description 41
- 239000003981 vehicle Substances 0.000 description 39
- 238000000338 in vitro Methods 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 230000037317 transdermal delivery Effects 0.000 description 30
- 241000282414 Homo sapiens Species 0.000 description 28
- 230000000694 effects Effects 0.000 description 26
- 239000003623 enhancer Substances 0.000 description 24
- -1 keratolyses Substances 0.000 description 24
- 239000006184 cosolvent Substances 0.000 description 23
- 238000010521 absorption reaction Methods 0.000 description 21
- 230000001186 cumulative effect Effects 0.000 description 21
- 229960004063 propylene glycol Drugs 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 19
- 108020003175 receptors Proteins 0.000 description 18
- 102000005962 receptors Human genes 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 230000035515 penetration Effects 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 210000000434 stratum corneum Anatomy 0.000 description 14
- 239000013543 active substance Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 230000001225 therapeutic effect Effects 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
- 230000008901 benefit Effects 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 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 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
- 210000002615 epidermis Anatomy 0.000 description 9
- 210000004400 mucous membrane 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000011156 evaluation Methods 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
- 230000036556 skin irritation Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 206010040880 Skin irritation Diseases 0.000 description 7
- 230000004888 barrier function Effects 0.000 description 7
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- 210000004207 dermis Anatomy 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 231100000475 skin irritation Toxicity 0.000 description 7
- 238000013268 sustained release Methods 0.000 description 7
- 239000012730 sustained-release form Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 230000007794 irritation Effects 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
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- 208000012902 Nervous system disease Diseases 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229960001484 edetic acid Drugs 0.000 description 5
- 230000002500 effect on skin Effects 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
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- 150000002430 hydrocarbons Chemical group 0.000 description 5
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
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- 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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- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-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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- A—HUMAN NECESSITIES
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- 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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- 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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- 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
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- 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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Landscapes
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- Neurosurgery (AREA)
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- Psychology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81725906P | 2006-06-29 | 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)
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| NZ572481A true NZ572481A (en) | 2011-03-31 |
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|---|---|---|---|
| NZ572481A NZ572481A (en) | 2006-06-29 | 2007-06-26 | Pharmaceutical compositions of ropinirole and methods of use thereof |
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| Country | Link |
|---|---|
| US (1) | US20080004329A1 (https=) |
| EP (1) | EP2032125A2 (https=) |
| JP (1) | JP2009542657A (https=) |
| KR (1) | KR20090031598A (https=) |
| CN (1) | CN101478952A (https=) |
| AR (1) | AR063201A1 (https=) |
| AU (1) | AU2007269896A1 (https=) |
| BR (1) | BRPI0713801A2 (https=) |
| CA (1) | CA2654383A1 (https=) |
| IL (1) | IL195161A0 (https=) |
| MX (1) | MX2008015083A (https=) |
| NO (1) | NO20085158L (https=) |
| NZ (1) | NZ572481A (https=) |
| PE (1) | PE20080374A1 (https=) |
| TW (1) | TW200815045A (https=) |
| UY (1) | UY30442A1 (https=) |
| WO (1) | WO2008005240A2 (https=) |
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| 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 |
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (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 |
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- 2007-06-26 PE PE2007000821A patent/PE20080374A1/es not_active Application Discontinuation
- 2007-06-26 US US11/823,028 patent/US20080004329A1/en not_active Abandoned
- 2007-06-26 WO PCT/US2007/014821 patent/WO2008005240A2/en not_active Ceased
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- 2007-06-26 JP JP2009518225A patent/JP2009542657A/ja not_active Withdrawn
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- 2007-06-26 NZ NZ572481A patent/NZ572481A/en unknown
- 2007-06-26 KR KR1020097001878A patent/KR20090031598A/ko not_active Withdrawn
- 2007-06-26 EP EP07809906A patent/EP2032125A2/en not_active Withdrawn
- 2007-06-26 CN CNA2007800229856A patent/CN101478952A/zh active Pending
- 2007-06-26 CA CA002654383A patent/CA2654383A1/en not_active Abandoned
- 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
- 2008-11-06 IL IL195161A patent/IL195161A0/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| IL195161A0 (en) | 2009-08-03 |
| MX2008015083A (es) | 2008-12-10 |
| KR20090031598A (ko) | 2009-03-26 |
| JP2009542657A (ja) | 2009-12-03 |
| AU2007269896A1 (en) | 2008-01-10 |
| WO2008005240A2 (en) | 2008-01-10 |
| CN101478952A (zh) | 2009-07-08 |
| UY30442A1 (es) | 2008-01-31 |
| BRPI0713801A2 (pt) | 2012-11-06 |
| TW200815045A (en) | 2008-04-01 |
| AR063201A1 (es) | 2009-01-14 |
| PE20080374A1 (es) | 2008-06-11 |
| WO2008005240A3 (en) | 2008-05-08 |
| US20080004329A1 (en) | 2008-01-03 |
| NO20085158L (no) | 2009-01-15 |
| EP2032125A2 (en) | 2009-03-11 |
| CA2654383A1 (en) | 2008-01-10 |
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