HRP980105A2 - Pharmaceutical formulations containing poorly soluble drug substances - Google Patents
Pharmaceutical formulations containing poorly soluble drug substancesInfo
- Publication number
- HRP980105A2 HRP980105A2 HR980105A HRP980105A HRP980105A2 HR P980105 A2 HRP980105 A2 HR P980105A2 HR 980105 A HR980105 A HR 980105A HR P980105 A HRP980105 A HR P980105A HR P980105 A2 HRP980105 A2 HR P980105A2
- Authority
- HR
- Croatia
- Prior art keywords
- agents
- pharmaceutical formulation
- medicinal substance
- drug
- solution
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 25
- 229940088679 drug related substance Drugs 0.000 title abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 180
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 66
- 239000003814 drug Substances 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 55
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims abstract description 44
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000811 xylitol Substances 0.000 claims abstract description 44
- 229960002675 xylitol Drugs 0.000 claims abstract description 44
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims abstract description 44
- 235000010447 xylitol Nutrition 0.000 claims abstract description 44
- 238000009472 formulation Methods 0.000 claims abstract description 41
- 239000007903 gelatin capsule Substances 0.000 claims abstract description 35
- 239000000725 suspension Substances 0.000 claims abstract description 22
- 238000011049 filling Methods 0.000 claims abstract description 18
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims abstract description 10
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 claims abstract description 10
- 229940016286 microcrystalline cellulose Drugs 0.000 claims abstract description 10
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims abstract description 10
- 239000008108 microcrystalline cellulose Substances 0.000 claims abstract description 10
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims abstract description 7
- 229960001021 lactose monohydrate Drugs 0.000 claims abstract description 7
- 229940079593 drug Drugs 0.000 claims description 56
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 41
- 229920001223 polyethylene glycol Polymers 0.000 claims description 39
- 239000002202 Polyethylene glycol Substances 0.000 claims description 36
- 239000012907 medicinal substance Substances 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 229910001868 water Inorganic materials 0.000 claims description 28
- 238000004090 dissolution Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 229920002472 Starch Polymers 0.000 claims description 17
- 235000019698 starch Nutrition 0.000 claims description 17
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- 229940032147 starch Drugs 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 9
- 239000003212 astringent agent Substances 0.000 claims description 7
- 239000008177 pharmaceutical agent Substances 0.000 claims description 7
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 5
- 102000055006 Calcitonin Human genes 0.000 claims description 5
- 108060001064 Calcitonin Proteins 0.000 claims description 5
- 239000000150 Sympathomimetic Substances 0.000 claims description 5
- 229940035676 analgesics Drugs 0.000 claims description 5
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- 230000000507 anthelmentic effect Effects 0.000 claims description 5
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- 229940124339 anthelmintic agent Drugs 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 230000003556 anti-epileptic effect Effects 0.000 claims description 5
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 5
- 239000000043 antiallergic agent Substances 0.000 claims description 5
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 5
- 239000003146 anticoagulant agent Substances 0.000 claims description 5
- 229940127219 anticoagulant drug Drugs 0.000 claims description 5
- 239000001961 anticonvulsive agent Substances 0.000 claims description 5
- 239000000935 antidepressant agent Substances 0.000 claims description 5
- 229940005513 antidepressants Drugs 0.000 claims description 5
- 239000003472 antidiabetic agent Substances 0.000 claims description 5
- 229940125708 antidiabetic agent Drugs 0.000 claims description 5
- 229960003965 antiepileptics Drugs 0.000 claims description 5
- 229940030225 antihemorrhagics Drugs 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 5
- 229940125715 antihistaminic agent Drugs 0.000 claims description 5
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- 229940030600 antihypertensive agent Drugs 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 229940034982 antineoplastic agent Drugs 0.000 claims description 5
- 239000003200 antithyroid agent Substances 0.000 claims description 5
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- 239000002249 anxiolytic agent Substances 0.000 claims description 5
- 230000000949 anxiolytic effect Effects 0.000 claims description 5
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 5
- 229960004015 calcitonin Drugs 0.000 claims description 5
- 230000000747 cardiac effect Effects 0.000 claims description 5
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- 206010061428 decreased appetite Diseases 0.000 claims description 5
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- 239000002874 hemostatic agent Substances 0.000 claims description 5
- 239000003018 immunosuppressive agent Substances 0.000 claims description 5
- 239000004041 inotropic agent Substances 0.000 claims description 5
- 239000003149 muscarinic antagonist Substances 0.000 claims description 5
- 229940035363 muscle relaxants Drugs 0.000 claims description 5
- 239000003158 myorelaxant agent Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 239000000734 parasympathomimetic agent Substances 0.000 claims description 5
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- 229940005542 parasympathomimetics Drugs 0.000 claims description 5
- 230000000849 parathyroid Effects 0.000 claims description 5
- 229940125723 sedative agent Drugs 0.000 claims description 5
- 239000000932 sedative agent Substances 0.000 claims description 5
- 239000000021 stimulant Substances 0.000 claims description 5
- 230000001975 sympathomimetic effect Effects 0.000 claims description 5
- 229940064707 sympathomimetics Drugs 0.000 claims description 5
- 229940065721 systemic for obstructive airway disease xanthines Drugs 0.000 claims description 5
- 210000001685 thyroid gland Anatomy 0.000 claims description 5
- 229940124549 vasodilator Drugs 0.000 claims description 5
- 239000003071 vasodilator agent Substances 0.000 claims description 5
- 239000003926 antimycobacterial agent Substances 0.000 claims description 4
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- 229940124584 antitussives Drugs 0.000 claims description 4
- 230000033228 biological regulation Effects 0.000 claims description 4
- 239000002981 blocking agent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 4
- 229940005501 dopaminergic agent Drugs 0.000 claims description 4
- 239000003163 gonadal steroid hormone Substances 0.000 claims description 4
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 230000000578 anorexic effect Effects 0.000 claims description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 3
- 150000003180 prostaglandins Chemical class 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 2
- 230000001539 anorectic effect Effects 0.000 claims description 2
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- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 239000007962 solid dispersion Substances 0.000 abstract description 27
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- 239000000243 solution Substances 0.000 description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 32
- 238000011109 contamination Methods 0.000 description 21
- 239000006185 dispersion Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002775 capsule Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
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- 239000000126 substance Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
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- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000356 contaminant Substances 0.000 description 5
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 229920002785 Croscarmellose sodium Polymers 0.000 description 3
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 3
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- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- 229920002593 Polyethylene Glycol 800 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 2
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
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- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 239000000463 material Substances 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
- 238000000386 microscopy Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000008342 pharmaceutical dispersion Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940071138 stearyl fumarate Drugs 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/813,946 US5837714A (en) | 1997-03-03 | 1997-03-03 | Solid pharmaceutical dispersions |
| US08/810,560 US5776987A (en) | 1997-03-03 | 1997-03-03 | Pharmaceutical suspension formulation |
| US08/808,761 US5760056A (en) | 1997-03-03 | 1997-03-03 | Pharmaceutical formulation |
| US2850498A | 1998-02-24 | 1998-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980105A2 true HRP980105A2 (en) | 1999-02-28 |
Family
ID=27487679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR980105A HRP980105A2 (en) | 1997-03-03 | 1998-03-02 | Pharmaceutical formulations containing poorly soluble drug substances |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0996436B1 (fr) |
| JP (2) | JP4510156B2 (fr) |
| AT (1) | ATE300293T1 (fr) |
| BR (1) | BR9808136A (fr) |
| CA (1) | CA2281946C (fr) |
| DE (1) | DE69830997T2 (fr) |
| ES (1) | ES2242273T3 (fr) |
| HR (1) | HRP980105A2 (fr) |
| NO (1) | NO325726B1 (fr) |
| WO (1) | WO1998038987A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6197787B1 (en) | 1997-03-03 | 2001-03-06 | Sanofi-Synthelabo | Pharmaceutical formulations containing poorly soluble drug substances |
| US6342249B1 (en) | 1998-12-23 | 2002-01-29 | Alza Corporation | Controlled release liquid active agent formulation dosage forms |
| AU1881600A (en) * | 1998-12-23 | 2000-07-31 | Alza Corporation | Dosage forms comprising porous particles |
| US6387400B1 (en) * | 2000-08-29 | 2002-05-14 | R.P. Scherer Technologies, Inc. | Process for preparing pharmaceutical compositions for use with soft gelatin formulations |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075607B1 (fr) * | 1981-09-25 | 1985-03-13 | Lacer, S.A. | 1-Azaxanthone à l'usage thérapeutique, procédés pour sa fabrication et compositions pharmaceutiques |
| US4725427A (en) * | 1984-03-13 | 1988-02-16 | Albion International, Inc. | Effervescent vitamin-mineral granule preparation |
| US5071643A (en) * | 1986-10-17 | 1991-12-10 | R. P. Scherer Corporation | Solvent system enhancing the solubility of pharmaceuticals for encapsulation |
| DD293499A5 (de) * | 1989-06-06 | 1991-09-05 | Arzneimittelwerk Dresden Gmbh,De | Verfahren zur herstellung cyclosporinhaltiger galenischer formulierungen |
| FR2665898B1 (fr) * | 1990-08-20 | 1994-03-11 | Sanofi | Derives d'amido-3 pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| AU661081B2 (en) * | 1991-11-04 | 1995-07-13 | Valeant International (Barbados) Srl | Water-soluble delivery systems for hydrophobic liquids |
| JP3121080B2 (ja) * | 1991-12-19 | 2000-12-25 | アール・ピー・シーラー コーポレイション | カプセル封入用溶液 |
| US5376688A (en) * | 1992-12-18 | 1994-12-27 | R. P. Scherer Corporation | Enhanced solubility pharmaceutical solutions |
| GB9302720D0 (en) * | 1993-02-11 | 1993-03-24 | Scherer Ltd R P | Products in capsule form for use in aqueous solution |
-
1998
- 1998-02-27 DE DE69830997T patent/DE69830997T2/de not_active Expired - Lifetime
- 1998-02-27 ES ES98907701T patent/ES2242273T3/es not_active Expired - Lifetime
- 1998-02-27 JP JP53867398A patent/JP4510156B2/ja not_active Expired - Fee Related
- 1998-02-27 BR BR9808136-5A patent/BR9808136A/pt not_active Application Discontinuation
- 1998-02-27 EP EP98907701A patent/EP0996436B1/fr not_active Expired - Lifetime
- 1998-02-27 WO PCT/US1998/004078 patent/WO1998038987A1/fr active IP Right Grant
- 1998-02-27 AT AT98907701T patent/ATE300293T1/de active
- 1998-02-27 CA CA002281946A patent/CA2281946C/fr not_active Expired - Fee Related
- 1998-03-02 HR HR980105A patent/HRP980105A2/hr not_active Application Discontinuation
-
1999
- 1999-09-02 NO NO19994249A patent/NO325726B1/no not_active IP Right Cessation
-
2009
- 2009-09-07 JP JP2009205861A patent/JP5563260B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69830997D1 (de) | 2005-09-01 |
| JP4510156B2 (ja) | 2010-07-21 |
| JP2002513406A (ja) | 2002-05-08 |
| EP0996436A1 (fr) | 2000-05-03 |
| CA2281946A1 (fr) | 1998-09-11 |
| NO994249D0 (no) | 1999-09-02 |
| ES2242273T3 (es) | 2005-11-01 |
| JP5563260B2 (ja) | 2014-07-30 |
| JP2009286798A (ja) | 2009-12-10 |
| EP0996436B1 (fr) | 2005-07-27 |
| ATE300293T1 (de) | 2005-08-15 |
| NO325726B1 (no) | 2008-07-07 |
| BR9808136A (pt) | 2000-03-28 |
| WO1998038987A1 (fr) | 1998-09-11 |
| EP0996436A4 (fr) | 2001-04-11 |
| DE69830997T2 (de) | 2006-02-09 |
| NO994249L (no) | 1999-11-03 |
| CA2281946C (fr) | 2007-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 19980302 Year of fee payment: 1 |
|
| A1OB | Publication of a patent application | ||
| OBST | Application withdrawn |