ZA200610513B - Pharmaceutical composition containing a stable and clear solution of anti-inflammatory drug in soft gelatin capsule and process for producing the same - Google Patents

Pharmaceutical composition containing a stable and clear solution of anti-inflammatory drug in soft gelatin capsule and process for producing the same Download PDF

Info

Publication number: ZA200610513B
Authority: ZA; South Africa
Prior art keywords: weight; pharmaceutical composition; soft gelatin; composition according; gelatin capsule
Prior art date: 2004-06-07

Application number

ZA200610513A

Other languages

English (en)

Inventor

Iyer Venkat Subramanian

Katageri Shivaraj Basavaraj

Original Assignee

Strides Arcolab Ltd

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.)

2004-06-07

Filing date

2004-06-07

Publication date

2008-06-25

2004-06-07 Application filed by Strides Arcolab Ltd filed Critical Strides Arcolab Ltd

2008-06-25 Publication of ZA200610513B publication Critical patent/ZA200610513B/en

Links

239000007903 gelatin capsule Substances 0.000 title claims description 48
239000008194 pharmaceutical composition Substances 0.000 title claims description 39
238000000034 method Methods 0.000 title claims description 21
230000008569 process Effects 0.000 title claims description 21
239000002260 anti-inflammatory agent Substances 0.000 title claims description 6
229940124599 anti-inflammatory drug Drugs 0.000 title claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 90
239000000203 mixture Substances 0.000 claims description 45
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 29
229960001680 ibuprofen Drugs 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 27
108010010803 Gelatin Proteins 0.000 claims description 25
239000008273 gelatin Substances 0.000 claims description 25
229920000159 gelatin Polymers 0.000 claims description 25
235000019322 gelatine Nutrition 0.000 claims description 25
235000011852 gelatine desserts Nutrition 0.000 claims description 25
VTGPMVCGAVZLQI-UHFFFAOYSA-M sodium;2-[4-(2-methylpropyl)phenyl]propanoate;dihydrate Chemical compound O.O.[Na+].CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 VTGPMVCGAVZLQI-UHFFFAOYSA-M 0.000 claims description 23
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 20
235000011187 glycerol Nutrition 0.000 claims description 20
235000019441 ethanol Nutrition 0.000 claims description 19
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 17
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 17
239000008213 purified water Substances 0.000 claims description 17
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 15
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 13
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 12
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 12
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 11
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 11
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 11
239000005642 Oleic acid Substances 0.000 claims description 11
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 11
229920001223 polyethylene glycol Polymers 0.000 claims description 11
229930003427 Vitamin E Natural products 0.000 claims description 10
238000012377 drug delivery Methods 0.000 claims description 10
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 10
WZWGGYFEOBVNLA-UHFFFAOYSA-N sodium;dihydrate Chemical compound O.O.[Na] WZWGGYFEOBVNLA-UHFFFAOYSA-N 0.000 claims description 10
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239000003963 antioxidant agent Substances 0.000 claims description 6
235000006708 antioxidants Nutrition 0.000 claims description 6
230000003078 antioxidant effect Effects 0.000 claims description 5
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 4
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239000003814 drug Substances 0.000 description 21
239000000243 solution Substances 0.000 description 21
239000002775 capsule Substances 0.000 description 19
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239000003826 tablet Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
238000005538 encapsulation Methods 0.000 description 6
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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 description 4
239000002253 acid Substances 0.000 description 4
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
239000008177 pharmaceutical agent Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000003381 solubilizing effect Effects 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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150000004665 fatty acids Chemical class 0.000 description 3
235000021472 generally recognized as safe Nutrition 0.000 description 3
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230000003000 nontoxic effect Effects 0.000 description 3
PTTPUWGBPLLBKW-UHFFFAOYSA-M sodium;2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound [Na+].CC(C)CC1=CC=C(C(C)C([O-])=O)C=C1 PTTPUWGBPLLBKW-UHFFFAOYSA-M 0.000 description 3
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SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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229920000858 Cyclodextrin Polymers 0.000 description 2
239000001116 FEMA 4028 Substances 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
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230000002378 acidificating effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
235000011175 beta-cyclodextrine Nutrition 0.000 description 2
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239000003086 colorant Substances 0.000 description 2
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150000002148 esters Chemical class 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
239000007909 solid dosage form Substances 0.000 description 2
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URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
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231100000716 Acceptable daily intake Toxicity 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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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 description 1
206010061218 Inflammation Diseases 0.000 description 1
235000019766 L-Lysine Nutrition 0.000 description 1
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229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
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206010037660 Pyrexia Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
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ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
239000007887 hard shell capsule Substances 0.000 description 1
229940051250 hexylene glycol Drugs 0.000 description 1
239000003906 humectant Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
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229960002009 naproxen Drugs 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
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235000021313 oleic acid Nutrition 0.000 description 1
239000003605 opacifier Substances 0.000 description 1
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229960001592 paclitaxel Drugs 0.000 description 1
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NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
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Classifications

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- A61K31/19—Carboxylic acids, e.g. valproic acid
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- 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
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
- 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
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
- 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]

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Inorganic Chemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Medicinal Preparation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

ZA200610513A 2004-06-07 2004-06-07 Pharmaceutical composition containing a stable and clear solution of anti-inflammatory drug in soft gelatin capsule and process for producing the same ZA200610513B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/IN2004/000158 WO2005120459A2 (en)	2004-06-07	2004-06-07	Pharmaceutical composition containing a stable and clear solution of anti-inflammatory drug in soft gelatin capsule and process for producing the same

Publications (1)

Publication Number	Publication Date
ZA200610513B true ZA200610513B (en)	2008-06-25

Family

ID=35503636

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200610513A ZA200610513B (en)	2004-06-07	2004-06-07	Pharmaceutical composition containing a stable and clear solution of anti-inflammatory drug in soft gelatin capsule and process for producing the same

Country Status (10)

Country	Link
US (1)	US20060286164A1 (pl)
AU (1)	AU2004320488A1 (pl)
BR (1)	BRPI0418885A (pl)
CA (1)	CA2570649A1 (pl)
DK (1)	DK200700007A (pl)
GB (1)	GB2429916A (pl)
MX (1)	MXPA06014185A (pl)
PL (1)	PL381799A1 (pl)
WO (1)	WO2005120459A2 (pl)
ZA (1)	ZA200610513B (pl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20080317684A1 (en) *	2006-09-06	2008-12-25	Isw Group, Inc.	Topical Compositions
US9914968B2 (en)	2012-09-26	2018-03-13	Cepheid	Honeycomb tube
FR2997856B1 (fr) *	2012-11-14	2015-04-24	Pf Medicament	Pastille medicamenteuse a base d'ibuprofene sodique dihydrate
US9622970B2 (en) *	2014-05-08	2017-04-18	Yaguang Liu	Pharmaceutical composition containing lutein and antioxidant for treating and preventing human disease
EP3053598A1 (en)	2015-02-06	2016-08-10	Faes Farma, S.A.	Calcifediol soft capsules
GB2595301B (en) *	2020-05-21	2025-01-08	Reckitt Benckiser Health Ltd	Novel Formulation

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3437599C2 (de) *	1984-10-13	1987-04-16	Dolorgiet GmbH & Co KG, 5205 St Augustin	Ibuprofen enthaltende Weichgelatinekapseln
US5071643A (en) *	1986-10-17	1991-12-10	R. P. Scherer Corporation	Solvent system enhancing the solubility of pharmaceuticals for encapsulation
US5519057A (en) *	1986-11-14	1996-05-21	Johnson & Johnson--Merck Pharmaceuticals Co.	Ibuprofen-containing medicament
GB8813682D0 (en) *	1988-06-09	1988-07-13	Reckitt & Colmann Prod Ltd	Pharmaceutical compositions
EP0584108B1 (en) *	1991-05-13	2000-08-16	The Boots Company PLC	Pharmaceutical composition comprising ibuprofen salt
IT1264855B1 (it) *	1993-06-21	1996-10-17	Zambon Spa	Composizioni farmaceutiche contenenti sali dell'acido s(+)-2-(4-isobutilfenil) propionico con amminoacidi basici
US6221391B1 (en) *	1998-11-23	2001-04-24	Accucaps Industries Limited	Self-emulsifying ibuprofen solution and soft gelatin capsule for use therewith
CA2354233A1 (en) *	1998-12-11	2000-06-15	Pharmasolutions, Inc.	Self-emulsifying compositions for drugs poorly soluble in water
US6267985B1 (en) *	1999-06-30	2001-07-31	Lipocine Inc.	Clear oil-containing pharmaceutical compositions
US6294192B1 (en) *	1999-02-26	2001-09-25	Lipocine, Inc.	Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents
US6251426B1 (en) *	1999-09-02	2001-06-26	Banner Pharmacaps, Inc.	Ibuprofen-containing softgels

2004
- 2004-06-07 BR BRPI0418885-3A patent/BRPI0418885A/pt not_active IP Right Cessation
- 2004-06-07 MX MXPA06014185A patent/MXPA06014185A/es not_active Application Discontinuation
- 2004-06-07 US US10/545,601 patent/US20060286164A1/en not_active Abandoned
- 2004-06-07 PL PL381799A patent/PL381799A1/pl not_active Application Discontinuation
- 2004-06-07 GB GB0624498A patent/GB2429916A/en not_active Withdrawn
- 2004-06-07 CA CA002570649A patent/CA2570649A1/en not_active Abandoned
- 2004-06-07 AU AU2004320488A patent/AU2004320488A1/en not_active Abandoned
- 2004-06-07 ZA ZA200610513A patent/ZA200610513B/en unknown
- 2004-06-07 WO PCT/IN2004/000158 patent/WO2005120459A2/en not_active Ceased
2007
- 2007-01-04 DK DK200700007A patent/DK200700007A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2005120459A2 (en)	2005-12-22
PL381799A1 (pl)	2007-07-09
DK200700007A (da)	2007-01-24
MXPA06014185A (es)	2007-04-16
GB2429916A (en)	2007-03-14
BRPI0418885A (pt)	2007-11-27
WO2005120459A3 (en)	2006-03-09
CA2570649A1 (en)	2005-12-22
AU2004320488A1 (en)	2005-12-22
US20060286164A1 (en)	2006-12-21
GB0624498D0 (en)	2007-01-17

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