CA2655596C - Systeme de delivrance osmotique multiparticulaire - Google Patents

Systeme de delivrance osmotique multiparticulaire Download PDF

Info

Publication number: CA2655596C
Authority: CA; Canada
Prior art keywords: drug; composition; weight; dissolution medium; osmotic
Prior art date: 2006-06-27
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

CA2655596A

Other languages

English (en)

Other versions

CA2655596A1 (fr

Inventor

Graham Jackson

Tien Nghiem

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.)

Valeant International Bermuda

Original Assignee

Valeant International Barbados SRL

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.)

2006-06-27

Filing date

2007-06-26

Publication date

2011-10-25

2006-06-27 Priority claimed from US11/475,252 external-priority patent/US7241805B2/en

2007-06-26 Application filed by Valeant International Barbados SRL filed Critical Valeant International Barbados SRL

2008-01-03 Publication of CA2655596A1 publication Critical patent/CA2655596A1/fr

2011-10-25 Application granted granted Critical

2011-10-25 Publication of CA2655596C publication Critical patent/CA2655596C/fr

Status Expired - Fee Related legal-status Critical Current

2027-06-26 Anticipated expiration legal-status Critical

Links

230000003204 osmotic effect Effects 0.000 title claims abstract description 206
239000003814 drug Substances 0.000 claims abstract description 676
229940079593 drug Drugs 0.000 claims abstract description 674
239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 57
239000002357 osmotic agent Substances 0.000 claims abstract description 47
230000008021 deposition Effects 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 294
239000011859 microparticle Substances 0.000 claims description 143
239000012738 dissolution medium Substances 0.000 claims description 134
-1 metroprolol Chemical compound 0.000 claims description 108
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 80
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 76
239000000194 fatty acid Substances 0.000 claims description 73
239000011159 matrix material Substances 0.000 claims description 72
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235000002639 sodium chloride Nutrition 0.000 claims description 72
235000014113 dietary fatty acids Nutrition 0.000 claims description 70
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239000007864 aqueous solution Substances 0.000 claims description 68
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XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 56
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239000012729 immediate-release (IR) formulation Substances 0.000 claims description 32
FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims description 32
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical class CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 28
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
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RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 7
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 7
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound 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 description 7
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 7
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TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
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 description 6
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 description 6
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
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229910052783 alkali metal Inorganic materials 0.000 claims description 6
239000002246 antineoplastic agent Substances 0.000 claims description 6
239000002249 anxiolytic agent Substances 0.000 claims description 6
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KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Chemical class CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 6
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OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 6
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239000008108 microcrystalline cellulose Substances 0.000 claims description 6
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LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 6
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235000019698 starch Nutrition 0.000 claims description 6
KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 claims description 6
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TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 6
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YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 5
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
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URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims description 5
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PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 5
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CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 4
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GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
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238000011160 research Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
229940066675 ricinoleate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
210000001599 sigmoid colon Anatomy 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000011734 sodium Chemical class 0.000 description 1
229910052708 sodium Chemical class 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 1
229940023144 sodium glycolate Drugs 0.000 description 1
229940079862 sodium lauryl sarcosinate Drugs 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
229940045902 sodium stearyl fumarate Drugs 0.000 description 1
JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
XGRLSUFHELJJAB-JGSYTFBMSA-M sodium;[(2r)-2-hydroxy-3-[(z)-octadec-9-enoyl]oxypropyl] hydrogen phosphate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP(O)([O-])=O XGRLSUFHELJJAB-JGSYTFBMSA-M 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
BHTRKEVKTKCXOH-BJLOMENOSA-N taurochenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-BJLOMENOSA-N 0.000 description 1
BHTRKEVKTKCXOH-LBSADWJPSA-N tauroursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)CC1 BHTRKEVKTKCXOH-LBSADWJPSA-N 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
229940014499 ursodeoxycholate Drugs 0.000 description 1
RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 description 1
229940117958 vinyl acetate Drugs 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
239000011800 void material Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
239000002888 zwitterionic surfactant Substances 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
- A61K9/0002—Galenical forms characterised by the drug release technique; Application systems commanded by energy
- A61K9/0004—Osmotic delivery systems; Sustained release driven by osmosis, thermal energy or gas
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings

Landscapes

Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA2655596A 2006-06-27 2007-06-26 Systeme de delivrance osmotique multiparticulaire Expired - Fee Related CA2655596C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
USPCT/US2006/24832		2006-06-27
US11/475,252 US7241805B2 (en)	2005-06-27	2006-06-27	Modified release formulations of a bupropion salt
US11/475,252		2006-06-27
PCT/US2006/024832 WO2007002597A2 (fr)	2005-06-27	2006-06-27	Formulations a liberation modifiee d'un sel de bupropion
PCT/IE2007/000062 WO2008001341A1 (fr)	2006-06-27	2007-06-26	Système de délivrance osmotique multiparticulaire

Publications (2)

Publication Number	Publication Date
CA2655596A1 CA2655596A1 (fr)	2008-01-03
CA2655596C true CA2655596C (fr)	2011-10-25

Family

ID=38512133

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2655596A Expired - Fee Related CA2655596C (fr)	2006-06-27	2007-06-26	Systeme de delivrance osmotique multiparticulaire

Country Status (3)

Country	Link
EP (1)	EP2032124A1 (fr)
CA (1)	CA2655596C (fr)
WO (1)	WO2008001341A1 (fr)

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US8030297B2 (en)	2008-05-14	2011-10-04	Otonomy, Inc.	Controlled release corticosteroid compositions and methods for the treatment of OTIC disorders
EP2291178A4 (fr) *	2008-06-09	2013-07-24	Supernus Pharmaceuticals Inc	Formulations à libération contrôlée de pramipexole
US8846770B2 (en)	2008-06-18	2014-09-30	Otonomy, Inc.	Controlled release aural pressure modulator compositions and methods for the treatment of OTIC disorders
US8318817B2 (en)	2008-07-21	2012-11-27	Otonomy, Inc.	Controlled release antimicrobial compositions and methods for the treatment of otic disorders
EP2627323A4 (fr)	2010-10-12	2014-03-12	Univ Johns Hopkins	Compositions antitussives comprenant de la mémantine
US9119793B1 (en)	2011-06-28	2015-09-01	Medicis Pharmaceutical Corporation	Gastroretentive dosage forms for doxycycline
US9861585B2 (en)	2012-10-16	2018-01-09	Sun Pharmaceutical Industries Limited	Osmotic floating tablets
EP2724709A1 (fr) *	2012-10-24	2014-04-30	Unilever N.V.	Composition d'écran solaire contenant des sels de L-DOPA-ester
CN102994477B (zh) *	2012-11-26	2014-09-17	河北省微生物研究所	修饰的米曲霉乳糖酶及其制备方法和应用
CN103142491B (zh) *	2013-02-06	2015-07-15	广东先强药业有限公司	一种单磷酸阿糖腺苷微球给药系统及其制备方法
US10842802B2 (en)	2013-03-15	2020-11-24	Medicis Pharmaceutical Corporation	Controlled release pharmaceutical dosage forms
CA3042642A1 (fr)	2013-08-12	2015-02-19	Pharmaceutical Manufacturing Research Services, Inc.	Comprime extrude anti-abus a liberation immediate
JP2016534121A (ja)	2013-08-27	2016-11-04	オトノミ—，インク．	小児の耳の病気の処置
US9492444B2 (en)	2013-12-17	2016-11-15	Pharmaceutical Manufacturing Research Services, Inc.	Extruded extended release abuse deterrent pill
US10172797B2 (en)	2013-12-17	2019-01-08	Pharmaceutical Manufacturing Research Services, Inc.	Extruded extended release abuse deterrent pill
CA2955229C (fr)	2014-07-17	2020-03-10	Pharmaceutical Manufacturing Research Services, Inc.	Forme posologique remplie de liquide anti-abus a liberation immediate
US9132096B1 (en)	2014-09-12	2015-09-15	Alkermes Pharma Ireland Limited	Abuse resistant pharmaceutical compositions
AU2015336065A1 (en)	2014-10-20	2017-05-04	Pharmaceutical Manufacturing Research Services, Inc.	Extended release abuse deterrent liquid fill dosage form
CN105935356B (zh) *	2016-03-28	2018-11-13	赤峰赛林泰药业有限公司	一种重酒石酸卡巴拉汀的固体制剂的制备方法
EP3512513A4 (fr)	2016-09-16	2020-04-15	Otonomy, Inc.	Formulations de gel otique pour le traitement de l'otite externe
EP3960158B1 (fr)	2016-10-07	2025-05-21	Silvergate Pharmaceuticals, Inc.	Formulations d'amlodipine
CN110121342A (zh) *	2016-12-28	2019-08-13	富士胶片富山化学株式会社	医药组合物
WO2019200143A1 (fr)	2018-04-11	2019-10-17	Silvergate Pharmaceuticals, Inc.	Formulations d'amlodipine
CA3142240A1 (fr) *	2019-06-03	2020-12-10	Synthetic Biologics, Inc.	Formulations de phosphatase alcaline et leurs utilisations
CN114469904B (zh) *	2022-02-18	2024-04-05	贵州拜乐锦生物技术有限公司	组合物、制备方法及在制备甲板涂敷产品中的应用
CN115350156B (zh) *	2022-08-26	2023-11-28	丽珠集团丽珠制药厂	一种克拉霉素片及其制备方法
CN116251067B (zh) *	2023-04-23	2024-06-07	淄博市中心医院	一种氟康唑片、制备方法及用途

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US5698224A (en) *	1994-06-27	1997-12-16	Alza Corporation	Tacrine therapy
US20030185882A1 (en) *	2001-11-06	2003-10-02	Vergez Juan A.	Pharmaceutical compositions containing oxybutynin
US8329217B2 (en) *	2001-11-06	2012-12-11	Osmotica Kereskedelmi Es Szolgaltato Kft	Dual controlled release dosage form
TW200414900A (fr) *	2002-06-28	2004-08-16
DE102004062475A1 (de) *	2004-12-24	2006-07-06	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung

2007
- 2007-06-26 CA CA2655596A patent/CA2655596C/fr not_active Expired - Fee Related
- 2007-06-26 WO PCT/IE2007/000062 patent/WO2008001341A1/fr not_active Ceased
- 2007-06-26 EP EP07736118A patent/EP2032124A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
CA2655596A1 (fr)	2008-01-03
EP2032124A1 (fr)	2009-03-11
WO2008001341A1 (fr)	2008-01-03

Legal Events

Date	Code	Title	Description
2008-12-16	EEER	Examination request
2020-10-13	MKLA	Lapsed	Effective date: 20200831

Publication	Publication Date	Title
CA2655596C (fr)	2011-10-25	Systeme de delivrance osmotique multiparticulaire
US20090004281A1 (en)	2009-01-01	Multiparticulate osmotic delivery system
US7241805B2 (en)	2007-07-10	Modified release formulations of a bupropion salt
US7645802B2 (en)	2010-01-12	Bupropion hydrobromide and therapeutic applications
US8354453B2 (en)	2013-01-15	Bupropion hydrobromide and therapeutic applications
US20070184115A1 (en)	2007-08-09	Modified release formulations of tramadol and uses thereof
AU2012216590A1 (en)	2012-09-20	Modified-release formulations of a bupropion salt